(B) Description of the Related Art Cationic surfactants provide their hydrophilic portion as a cation when dissolved in water. Such cationic surfactants show normal surface active effects such as cleaning, emulsification, solubility, etc. and at the same time, they exhibit softening effects or anti-electrostatic effects, they are classified into quaternary ammonium salts and amine derivatives according to their structural characteristics.

In prior arts, DDAC (dimethyl dialkyl ammonium chloride) was widely used as a typical cationic surfactant (JAOCS 61,367 (1984), and 65 (10), 1682 (1988) ), but recently, its usage amounts are being reduced slowly because of its low bio-degradability. Hence, studies on introducing a group having

degradable functional groups such as an ester or amide within an alkyl group into a molecule are in active progress.

As such cationic surfactants, quaternary ammonium salts of amidoamine, quaternary ammonium salts of amidoesteramine, cationic surfactants of imidazoline and imidazoline esters, etc. are conventionally widely used and they are mostly used as a major component of fiber softeners.

For example, Japanese Patent Pyung No. 6-345704 describes an amidoamine compound, a process for preparing cationic surfactants using it, and a method of using it as a softener, and Japanese Patent Pyung No. 6-336466 describes an amidoesteramine compound, a process for preparing cationic surfactants using it, and a method of using it as a softener. Also, Japanese Patent Pyung No. 4-257372 discloses a process for preparing imidazoline ester and a softening composition, and Japanese Patent Pyung No. 2-1479 discloses a process for preparing an imidazoline and a conditioning compound comprising it.

Above imidazoline and imidazoline ester are prepared by reacting a diethyltriamine and aminoethylaminoethanole with two equivalents of fatty acids and quaternalizing the reactant with dimethylsulfate. However, these cationic surfactants show an improved bio-degradability as compared with cationic dialkyldimethylammonium salts, but they are still unsatisfactory.

Recently, it has been reported that when an alkyl group, which is a lipophilic portion of cationic surfactants includes easily-degradable functional groups such as an ester group, their bio-degradability becomes highly excellent as compared with the above-mentioned prior dimethyldialkyl ammonium chloride,

amide type quaternary ammonium salts, and imidazoline type cationic surfactants (Tenside Surfactant Detergent, 1993, 30, 186-191).

Hence, various derivatives of quaternary ammonium salts having an ester group within molecules are being widely studied, and as a commercialized typical example, International Laid-Open Patent No. 94/07928 describes a method of preparing a softener and haircare products using quaternalized cationic surfactants induced from a triethanole amine. International Laid-Open Patent No. 93/23510 discloses a method of preparing a condensed fiber softener and bio-degradable fiber softening composition using cationic surfactants having an ester bond between two hydrophobic groups, and International Laid-Open Patent No. 92/15745 discloses a method of preparing a condensed fiber softening composition using a linear fatty alcohol ethoxylate, polydialkylsiloxane, etc in an imidazoline or imidazoline ester. Also, International Laid-Open Patent No. 94/14935 describes a method of preparing a condensed fiber softening dispersion comprising quaternary ammonium compounds prepared from triethanole amines and fatty acids and International Laid-Open Patent No.

94/13772 describes a method of preparing a highly-condensed fiber softener using a quaternary ammonium compound having an ester group within molecules and a non-ionic dispersion in a small amount.

However, in case of imidazoline type quaternary ammonium salts, their structure is unstable and thus imidazoline ring is broken in water. Also, in case of quaternary ammonium salts containing an ester group within molecules, their solubility to water is quite poor, and thus, in order to maintain product stability for

an extended time period, they have to use compounds such as glycerines, lower alcohols, non-ionic dispersions, etc. in a large amount, which causes the deterioration of the inherent, basic performances of ammonium salts.

Accordingly, in order to increase hydrophilic properties, an oleyl group is introduced into an alkyl group, which is a hydrophobic portion, but this causes severe discoloration and foul odors during process.

Recently, in order to make quaternalization easy, cationic surfactants wherein tertiary amines are neutralized with acids are being studied for example, in Japanese Laid-Open Patent Pyung No. 5-195433, Pyung No. 5-195432, Pyung <BR> <BR> No. 6-57632, Pyung No. 5-132860, Pyung No. 5-230763, etc. , but as several by-products are produced when cured fatty acids are reacted with amines in the above methods, expensive amines that are not generally used for an industrial purpose had to be used and thus they were not desirable.

Also, in Japanese Laid-Open Patent Pyung No. 3-295855, Pyung No.

4-208964, Pyung No. 4-267468, Pyung No. 4-28023, and Pyung No. 4-6984, there are disclosed fiber softeners having amidoester type tertiary amines and quaternary salts with an excellent dispersion in water as a major component, but these fiber softeners have a problem that their storage stability falls down at a high temperature.

SUMMARY OF THE INVENTION The present invention is made in consideration of the problems of the prior art, and it is an object of the invention to provide a process for the preparation of a cationic surfactant having excellent solubility in water by

possessing an amide group or hydroxyl group, which is hydrophilic, within molecules and showing highly excellent softening properties, anti-electrostatic properties and dispersion.

It is an another object of the invention to provide a process for the preparation of a cationic surfactant with a high efficiency by a simple method while minimizing by-products.

It is still another object of the invention to provide a fiber softening composition having uniform adhesion effects onto clothes and thereby having excellent softening properties, anti-electrostatic effects, and absorption.

It is still another object of the invention to provide a fiber softening composition with a remarkably-improved storage stability, dispersion in water and bio-degradable effects.

To achieve the foregoing objects, the present invention provides a process for preparing a cationic surfactant represented by the following formula 1: wherein Ri is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21 ; X is CH3, (CH2) mOH, (CH2) mOCOR2, (CH2) mNH2, or (CH2) mNHCOR2, wherein R2 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21, and m is an integer of 2 to 6; Y is a hydrogen atom, CH2CHOHCH20H, CH2CHOHCH2CI, CH2CH2CN, CH2CH2COOCH3, CH2CH2COOH, or CH2CH20H ;

Z is a hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, glyconic acid, apple acid, tin acid, tartaric acid; and n is an integer of 2 to 6; comprising the steps of: a) reacting an amine and a higher fatty acid; b) tertiarizing the reactant obtained from step a); and c) quaternarizing the tertiary amine obtained from step b) by neutralizing it with an acid.

Further, the invention provides a fiber softening composition comprising the compound represented by the above formula 1.

Also, the present invention provides a process for preparing a cationic surfactant represented by the following formula 2: wherein R3 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21 ; R4 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C1-C21 ; X is CH3, (CH2) mOH, (CH2), OCORS, (CH2) mNH2, or (CH2) mNHCOR5, wherein R5 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21, m is an integer of 2 to 6; Y is a hydrogen atom, CH2CHOHCH20H, CH2CHOHCH2CI, CH2CH2CN, CH2CH2COOCH3, CH2CH2COOH, or CH2CH20H ;

M is a sulfate or halogen atom; and n is an integer of 2 to 6; comprising the steps of: a) reacting a fatty acid of the following formula 6: wherein R3 is as defined above; and an amine of the following formula 7: H2N (CH2) nNH-X wherein n and X are as defined above; to prepare an amido amine of the following formula 5: wherein R3, n and X are as defined above; b) tertiarizing the amido amine of the above formula 5 with a tertiarizing agent (Y) to prepare a compound of the following formula 4: wherein R3, n, X and Y are as defined above; c) quaternarizing the compound of above formula 4 with a compound of the following formula 3: R4-M wherein R4 and M are as defined above.

Further, the invention provides a fiber softening composition comprising the amido ammonium salt represented by the above formula 2.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention is hereafter described in detail.

The present invention is characterized by a process for preparing a cationic surfactant of formula 1 as defined above by reaction of using a fatty acid, an amine and a tertiarizing agent and then quaternarization reaction by neutralizing with an acid, and a fiber softening composition comprising it.

Also, the present invention is characterized by a process for preparing a cationic surfactant of formula 2 as defined above by reacting a fatty acid and an amine, tertiarizing it and quaternarizing it with a dimethylsulfate or alkylhalide, and a fiber softening composition comprising it.

The present invention can improve solubility in water by introducing an amide or hydroxyl group, which is hydrophilic, within molecules and minimize by-products while maintaining softening power, anti-electrostatic power, etc., which are the intrinsic performances of quaternary ammonium salts, to same or high extent as the prior quaternary ammonium salts.

The following description is directed to a process for preparing of the cationic surfactant of formula 1 of the present invention. Preparation of quaternarized ester derivative of formula 1 as defined above is shown in the following scheme 1: [Scheme 1]

In the scheme 1 above, R1 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21 ; X is CH3, (CH2) mOH, (CH2) mOCOR2, (CH2) mNH2, or (CH2) mNHCOR2, wherein R2is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21, and m is an integer of 2 to 6; Y is a hydrogen atom, CH2CHOHCH20H, CH2CHOHCH2CI, CH2CH2CN, CH2CH2COOCH3, CH2CH2COOH, or CH2CH20H ; Z is a hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, glyconic acid, apple acid, tin acid, tartaric acid; and n is an integer of 2 to 6; As shown in scheme 1, the present invention is proceeded by the reactions of three steps.

First, in a first step, a higher fatty acid and an amine are reacted to produce an amido amine.

As the amine used in the first reaction, there can be used quaternary ammonium salts of amidoamine, quaternary ammonium salts of amidoesteramine, imidazolines, imidazoline esters, etc. , and it is preferred to use aminoethylaminoethanole or diethylenetriamine. The amine is used in an amount of 0.5 to 1.0 equivalent with regard to 1 equivalent of the higher fatty acid, and if the amount of the amine is less than 0.5 equivalent, unreacted fatty acids

remain or the amount of amines, which can become quaternary salts, is decreased, thereby causing the deterioration of physicochemical properties, and if it exceeds 1.0 equivalent, the amount of unreacted amines is increased and thus toxicity increases and the productivity is low.

As the higher fatty acid, it is preferable to use a mixture of one or more kinds having a linear or branched alkyl group or alkenyl group of C8-C22 For example, there are stearic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, etc.

In the first reaction, the amine and the higher fatty acid are reacted without solvents, and it is preferred that reaction temperature is 100-180 °C and reaction time is 1-20 hours.

In a second step, a tertiarizing agent is added to the produced amido amine to tertiary it.

It is preferred to use the tertiarizing agent used in the second reaction in an amount of less than 1.0 equivalent with regard to 1 equivalent of the amido amine, which is the reactant prepared from the first reaction. If the amount of the tertiarizing agent exceeds 1 equivalent, unreacted tertizaring agent remains and thus discoloration and foul odor occur and physicochemical properties are deteriorated.

As the tertiarizing agent, there are glycidol, ephichlorohydrine, acrylonitrile, methyl acrylate, acrylic acid, vinyl alcohol, etc.

Also, the above tertiarizing reaction may be carried out with or without

solvents. In case of using the solvents, as reaction solvents, there are used one or more primary, secondary, tertiary or polyvalent alcohols selected from the group consisting of water, methanole, ethanole, propylalcohol, hexyleneglycol, butylalcohol, isopropylalcohol, ethyleneglycol, glycerine, propyleneglycol, polyethyleneglycol and it is preferable to use 1 to 99% by weight of the total weight of the reactants.

It is preferred that the above tertiarizaing reaction is carried out at reaction temperature of 30-100 °C and for reaction time of 0. 1-5 hours.

In a third step, the tertiarized amine compound is neutralized with an acid to quaternarize it, thereby producing a quaternary salt.

Especially, the present invention is characterized in that in the quaternarizing step, the neutralization is performed only by acid to prepare a quaternary salt, instead of quaternarizing by addition of an additional quaternarizing reagent as used before. According to such process, quaternary salts of quaternarized amido amine, quaternary salts of amido ester amine or quaternary salts of diamido amine can be prepared with high efficiency.

As the acid used in the above neutralization in the present invention, it is preferable to use hydrochloric acid, sulfuric acid, phosphoric acid, glyconic acid, apple acid, tin acid or tartaric acid.

As above described, according the present invention, the cationic surfactant represented by formula as defined can be prepared with high efficiency which is excellent in solubility in water by possessing an amide group or hydroxyl group, which is hydrophilic, within molecules and is highly excellent in

physicochemical characteristics such as softening properties, anti-electrostatic properties and dispersion properties.

Further, the present invention provides a fiber softening composition comprising the compound of formula 1 prepared from the methods as described above.

The inventors continued to apply compounds suitable for use of fiber softeners as a major component and as a result, they found that the fiber softening composition comprising the quaternary salt of amidoamine of formula 1 as defined above as a major component is excellent uniform adhesion effects onto clothes and thus has excellent softening properties, anti-electrostatic effects, and absorption at the same time as well as excellent dispersion in water and bio-degradability, thereby completing the present invention.

In the formula 1, R2 is linear or branched alkyl group, alkenyl group or alkylalkenyl group of C7 to C21, and if the number of carbon atoms is less than 7, the adhesion effects onto clothes are not maintained, thereby causing the deterioration of softening effects and anti-electrostatic effects and if the number of carbon atoms exceeds 22, slipping or excessive softening effects occur, thereby causing poor touch.

In the fiber softening composition of the present invention, the fiber softening composition comprises the quaternary salt of amidoamine of formula 1 as defined above as a major component. In addition to the quaternary salt of amidoamine of formula 1, quaternary salts of amidoesteramine, or quaternary salts of diamidoamine may be comprised, and especially, it is preferable to

comprise the quaternary salts of amidoamine. The quaternary salt of amidoamine of formula 1 may be used alone or in a mixture and it is preferred to use the quaternary salt of amidoamine of formula 1 in an amount of 1 to 30 parts by weight in the fiber softening composition. When the quaternary salt of amidoamine of formula 1 is used alone or by mixture in the fiber softening composition, if it is used in an amount of less than 1 part by weight, softening effects or anti-electrostatic effects onto all kinds of clothes are unsatisfactory and if it is used exceeding 30 parts by weight, softening stability and freezing stability may become poor.

The fiber softening composition according to the present invention may use, if necessary, a non-ionic surfactant as a softening agent in addition to the compound of formula 1, which is a cationic softening component.

The examples of the non-ionic surfactant used as a suitable softening agent of the cationic softening component in the present invention include polyoxyethylene (2 to 50 mol) alkyl-alkenylether or polyoxyethylne (2 to 50 mol)-alkyl phenyl ether (2 to 50 mol) of C10-C20 poiyoxyethylene (2 to 50 mol) alkyl-alkenylester or polyoxyethylene (2 to 50 mol) alkyl-hydroxy fatty acid ester of C10-C20 ; sorbitane fatty acid alkyl ester or its ethylene oxide (15 to 40 mol) additives, polyoxyethylene (1 to 30 mol) alkyl-alkenylamide ; polyoxyethylene (1 to 50 mol) alkyl-alkenylamine, glyceryl monoalkyl-alkenyl ester; ethylene oxide additives (2 to 50 mol) of cured castor oil ; alkylamineoxide ; and amidopropylamineoxide, and these surfactants can be used alone or in a mixture of two more kinds. It is preferred to use the non-ionic surfactant in an amount of

0.1 to 30 parts by weight with regard to 100 parts by weight of the compound of formula 1. If the content of the non-ionic surfactant exceeds 30 parts by weight, the stability of products is deteriorated and it prevents the cationic softening component of the quaternary salt of amidoamine represented by formula 1 from being adhered to clothes, thereby causing the deterioration of softening effects.

Also, if necessary, the fiber softening composition of present invention may further comprise a dispersion stabilizer. As the dispersion stabilizer, there can be used lower alcohol or glycols of Ci to C8, higher alcohols of Cis to C20, iodide, magnesium, sodium chloride, calcium chloride, sodium nitrate, or a mixture thereof. More preferably, there can be used ethanole, isopropyl alcohol, ethyleneglycol, propyleneglycol, hexyleneglycol, trimethylpentanediol, setylalcohol, stearylalcohol, magnesium chloride, sodium chloride, calcium chloride, sodium nitrate, a mixture of thereof. It is preferred to use the dispersion stabilizer in an amount of 0.1 to 30 parts by weight with regard to 100 parts by weight of the compound of formula 1. If the content of the dispersion stabilizer exceeds 30 parts by weight, the softening effects of the fiber softening composition may be deteriorated and cause unnecessary increase in cost.

Furthermore, the fiber softening composition of the present invention may further comprise fragrants, antiseptic agents, disinfectants, fluorescent whitening agents, colorants, anti-oxidants, anti-foaming agents, etc. , which are generally used as an additive of fiber softeners, within the range of not affecting product stability, and their content may be 0.1 to 3% by weight.

The following decription is directed to a process for preparing of the

cationic surfactant of formula 2 of the present invention. Preparation of quaternarized ester derivative of formula 2 as defined above is shown in the following scheme 2: [Scheme 2] In the scheme 2 above, R3 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21 ; R4 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of Ci-C21 ; X is CH3, (CH2) mOH, (CH2) mOCOR5, (CH2) mNH2, or (CH2) mNHCOR5 ol, wherein R5 is a linear or branched alkyl group, alkenyl group, or a mixed group comprising one or more kinds of C7-C21, m is an integer of 2 to 6; Y is a hydrogen atom, CH2CHOHCH20H, CH2CHOHCH2CI, CH2CH2CN, CH2CH2COOCH3, CH2CH2COOH, or CH2CH20H ; M is a sulfate or halogen atom; and n is an integer of 2 to 6 As shown in scheme 2, the present invention is proceeded by the

reactions of three steps.

First, in a first step, a fatty acid of formula 6 as defined above and an amine of formula 7 as defined above are reacted to produce an amido amine of formula 5 as defined above.

As the amine used in the first reaction, there can be used quaternary ammonium salts of amidoamine, quaternary ammonium salts of amidoesteramine, <BR> <BR> imidazolines, imidazoline esters, etc. , and it is preferred to use aminoethylaminoethanole or diethylenetriamine. The amine is used in an amount of 0.5 to 1.0 equivalent with regard to 1 equivalent of the higher fatty acid, and if the amount of the amine is less than 0.5 equivalent, unreacted fatty acids remain or the amount of amines, which can become quaternary salts, is decreased, thereby causing the deterioration of physicochemical properties, and if it exceeds 1.0 equivalent, the amount of unreacted amines is increased and thus toxicity increases and the productivity is low.

As the fatty acid, it is preferable to use a higher fatty acid of one or more kinds having a linear or branched alkyl group or alkenyl group of C8-C22. For example, there are stearic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, etc.

In the first reaction, the amine and the higher fatty acid are reacted without solvents, and it is preferred that reaction temperature is 100-180 °C and reaction time is 1-20 hours. If the reaction temperature is less than 100 °C, the reaction is proceeded very slow and thus reaction time becomes very

extended, and if exceeding 180 C, reaction is proceeded fast but in consideration of efficiency and time altogether, much energy is consumed as compared to time to be reduced and the content of tertiary amine is increased.

Also, if the reaction time is less than 1 hour, a reaction yield is very low and if exceeding 20 hours, a yield is not increased any more.

In a second step, a tertiarizing agent (Y) is added to the produced amido amine of formula 5 to tertiary it.

It is preferred to use the tertiarizing agent used in the second reaction in an amount of less than 1.0 equivalent, and more preferably 0.5 to 1.0 equivalent, with regard to 1 equivalent of the amido amine, which is the reactant prepared from the first reaction, If the amount of the tertiarizing agent exceeds 1 equivalent, unreacted tertizaring agent remains and thus discoloration and foul odor occur and physicochemical properties are deteriorated As the tertiarizing agent, there are glycidol, ephichlorohydrine, acrylonitrile, methyl acrylate, acrylic acid, vinyl alcohol, etc.

Also, the above tertiarizing reaction may be carried out with or without solvents. In case of using the solvents, as reaction solvents, there are used one or more primary, secondary, tertiary or polyvalent alcohols selected from the group consisting of water, methanole, ethanole, propylalcohol, hexyleneglycol, butylalcohol, isopropylalcohol, ethyleneglycol, glycerine, propyleneglycol, polyethyleneglycol and it is preferable to use 1 to 99% by weight of the total weight of the reactants.

It is preferred that the above tertiarizaing reaction is carried out at reaction

temperature of 30-100 °C and for reaction time of 0. 1-5 hours. If the reaction temperature is less than 30 °C, a reaction rate is very slow and thus reaction time becomes very extended, and if exceeding 100 oC, undesired by-products may be produced in a large amount. Also, if the reaction time is less than 0.1 hour, reaction is hardly proceeded, and if exceeding 5 hours, a by-reaction occurs and thus the amount of the by-products is increased.

In a third step, the tertiarized amine compound is neutralized with a compound of formula 3 to quaternarize it, thereby producing a quaternary salt of formula 2.

As the compound of formula 3 used as a quaternarizing agent in the present invention, it is preferable to use a dimethylsulfate or an alkylhalide having an alkyl group of Ci-C21, It is preferred to use the compound of formula 3 used as quaternarizing agent within a range of not exceeding the equivalent of the total amine after the tertiarizing reaction is completed. It is preferred that the reaction temperature 30 to 100 °C and the reaction time is 1.0 to 8.0 hours.

Also, in the present invention, after the first reaction, the quaternarizing reaction can be proceeded directly, omitting the tertiarizing reaction, which is the second step.

Further, the present invention provides a fiber softening composition comprising the amidoammonium salt having an amide group and hydroxyl group within molecules represented by formula 2 prepared from the methods as described above.

The inventors continued to apply compounds suitable for use of fiber softeners as a major component and as a result, they found that the fiber softening composition using the amido ammonium salt having an amide group and a hydroxyl group within molecules, which is prepared by reacting a fatty acid and an amine, tertiarizing it, and quaternarizing it with a dimethylsulfate or alkylhalide, is excellent uniform adhesion effects onto clothes and thus has excellent softening properties, anti-electrostatic effects, and absorption at the same time as well as excellent dispersion in water and bio-degradability, thereby completing the present invention.

In the amido ammonium salt represented by formula 2 in the present invention, R2 is a linear or branched alkyl group, alkenyl group or alkylalkenyl group of Ci to C21, and if the number of carbon atoms is less than 1, the adhesion effects onto clothes are not maintained, thereby causing the deterioration of softening effects and anti-electrostatic effects and if the number of carbon atoms exceeds 21, slipping or excessive softening effects occur, thereby causing poor touch.

It is preferred to use the amido ammonium salt represented by formula 2 in an amount of 1 to 30 parts by weight with regard to 100 parts by weight of the fiber softening composition. If the content is less than 1 part by weight, softening effects or anti-electrostatic effects onto all kinds of clothes are unsatisfactory and if it exceeds 30 parts by weight, softening stability and freezing stability may become poor.

The fiber softening composition according to the present invention may

use, if necessary, a non-ionic surfactant as a softening agent in addition to the amido ammonium salt represented by formula 2, which is a cationic softening component.

As the above non-ionic surfactant, there can be used polyoxyethylene (2 to 50 mol) alkyl-alkenylether or polyoxyethyine (2 to 50 mol)-alkyl phenyl ether (2 to 50 mol) of Ci0-C20 ; polyoxyethylene (2 to 50 mol) alkyl-alkenylester or polyoxyethylene (2 to 50 mol) alkyl-hydroxy fatty acid ester of C10-C20 ; sorbitane fatty acid alkyl ester or its ethylene oxide (15 to 40 mol) additives, polyoxyethylene (1 to 30 mol) alkyl-aikenylamide ; polyoxyethylene (1 to 50 mol) alkyl-alkenylamine, glyceryl monoalkyl-alkenyl ester; ethylene oxide additives (2 to 50 mol) of cured castor oil ; alkylamineoxide ; and amidopropylamineoxide.

The non-ionic surfactant can be used alone or in a mixture of two more kinds. It is preferred to use the non-ionic surfactant in an amount of 0.1 to 30 parts by weight with regard to 100 parts by weight of the amido ammonium salt. If the content of the non-ionic surfactant exceeds 30 parts by weight, the stability of products is deteriorated and it prevents the amido ammonium salt, which is a cationic softening component, from being adhered to clothes, thereby causing the deterioration of softening effects.

Also, if necessary, the fiber softening composition of present invention may further comprise a dispersion stabilizer.

As the dispersion stabilizer, there can be used lower alcohol or glycols of Ci to C8, higher alcohols of C12 to C20, iodide, magnesium, sodium chloride, calcium chloride, sodium nitrate, or a mixture thereof. More preferably, there

can be used ethanole, isopropyl alcohol, ethyleneglycol, propyleneglycol, hexyleneglycol, trimethylpentanediol, setylalcohol, stearylalcohol, magnesium chloride, sodium chloride, calcium chloride, sodium nitrate, a mixture of thereof.

It is preferred to use the dispersion stabilizer in an amount of 0.1 to 30 parts by weight with regard to 100 parts by weight of the compound of formula 1.

If the content of the dispersion stabilizer exceeds 30 parts by weight, the softening effects of the fiber softening composition may be deteriorated and cause unnecessary increase in cost.

Furthermore, the fiber softening composition of the present invention may further comprise fragrants, antiseptic agents, disinfectants, fluorescent <BR> <BR> whitening agents, colorants, anti-oxidants, anti-foaming agents, etc. , which are generally used as an additive of fiber softeners, within the range of not affecting product stability, and their content may be 0.1 to 3% by weight.

The present invention will be explained in more detail with reference to the following Examples. However, these are to illustrate the present invention, and the present invention is not limited to them.

[Example 1] 104 g (1.0 mol) of 2-(2-aminoethylamino) ethanol and 408 g (1.5 mol) of stearic acid were amidified in four-sphere flask with a mechanical stirrer, thermometer, condenser and evaporating equipment at a temperature of 120- 130 °C for 2 hours while refluxing water produced during reaction, and then the temperature was raised to 160-170 °C to proceed an esterification reaction for 3 hours while removing water. After the reaction was complete, the total amine

value was 90%, tertiary amine value was 10%, secondary amine value was 80%, and acid value was 2%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S. Analysis (Official Method Te 2a-64, 1987), and 60 g of ethanole was added to the amidoesteramine thus prepared, to which 74 g of ephichlorohydrine was slowed dropped to allow the reaction to proceed for 1 hour, and then the reactant was neutralized with 97 g of hydrochloric acid (35%) to terminate the reaction.

[Example 2] 103 g (1.0 mol) of diethylenetriamine and 544 g (2.0 mol) of stearic acid were amidified in the apparatus identical to that used in Example 1 at a temperature of 120-130 °C for 10 hours while refluxing water produced during reaction. After the reaction was complete, the total amine value was 95%, tertiary amine value was 3%, secondary amine value was 90%, and acid value was 2%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S. Analysis (Official Method Te 2a-64,1987), and 80 g of ethanole was added to the diamidoamine thus prepared, to which 87 g of ephichlorohydrine was slowed dropped to allow the reaction to proceed for 1 hour, and then the reactant was neutralized with 103 g of hydrochloric acid (35%) to terminate the reaction.

[Example 3] 104 g (1.0 mol) of 2- (2-aminoethylamino) ethanole and 408 g (1.5 mol) of stearic acid were amidified in the apparatus identical to that used in Example 1 at a temperature of 120-130 °C for 2 hours while refluxing water produced during

reaction. After the reaction was complete, the primary amine value was 1%, tertiary amine value was 3%, and 1 equivalent of fatty acid was consumed. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S. Analysis (Official Method Te 2a-64,1987). 53 g of acrylonitrile was slowly added to the amidoesteramine thus prepared at a temperature of 70 - 90 °C for 1 hour. After the tertiarizing reaction was complete, the temperature was raised to 160-170 °C to proceed an esterification reaction for 3 hours while removing water. After the reaction was complete, 70 g of ethanole was added, and the reactant was neutralized with 103 g of hydrochloric acid (35%) to terminate the reaction.

[Comparative Example 1] 104 g (1.0 mol) of 2- (2-aminoethylamino) ethanole and 272 g (1.0 mol) of stearic acid were amidified in the apparatus identical to that used in Example 1 at a temperature of 120-130 °C for 15 hours while refluxing water produced during reaction. After the reaction was complete, the total amine value was 95%, tertiary amine value was 4%, and acid value was 4%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S.

Analysis (Official Method Te 2a-64,1987). 50 g of ethanole was added to the amido amine thus prepared, and the reactant was neutralized with 103 g of hydrochloric acid (35%) at a temperature of 50-60 °C to terminate the reaction.

[Example 4] The procedures were carried out in the same manner as Example 1, except changing the kind of alkyl groups as shown in Table 1 below, to prepare cationic surfactants of formula 1 a to formula 1l.

Table 1 0 x R1CNH (CH2) nNs Z v Formula 1 (wherein Z is HCI) Category R'x y R3 n, m Formula Cured cow fat fatty CH2CHOH (CH2) mOH 2 1a acid residue CH20H Formula Cured cow fat fatty CH2CHOH (CH2) mOH-2 1b acid residue CH2CI Formula Cured cow fat fatty (CH2) mOH H 2 1 c acid residue Formula Cured pam fatty CH2CHOH (CH2) mOH 2 1d acid residue CH2CI Formula Stearin fatty acid CH2CHOH (CH2) mOH 2 1 e residue CH2CI Oleinic acid fatty CH2CHOH Formula 1f (CH2) mOH-2 acid residue CH2CI Formula Cured cow fat fatty (CH2) mOC CH2CHOH Cured cow fat fatty 2 19 acid residue OR2 CH20H acid residue Formula Cured cow fat fatty (CH2) mOC CH2CHOH Cured cow fat fatty 2 1h acid residue OR2 CH2CI acid residue Cured pam fatty (CH2) mOC CH2CHOH Cured pam fatty Formula 1 i 2 acid residue OR2 CH2 CI H acid residue Stearin fatty acid (CH2) mOC CH2CHOH Stearin fatty acid Formula 1j 2 residue OR2 CH2CI residue Formula Oleinic fatty acid (CH2) mOC CH2CHOH Oleinic acid fatty 2 1 k residue OR2 CH2CI acid residue Stearin fatty acid (CH2) mOC CH2CHOH Stearine fatty acid Formula11 3 residue OR2 CH2CI residue

[Example 5] A fiber softening composition comprising 6% by weight of compound of formula 1 a, 0.5% by weight of a mixture of cured castor oil and polyoxyethylene (POE) whose molecular weight is 40,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0.1 % by weight of fragrance was prepared.

[Example 6] A fiber softening composition was prepared in the same manner as Example 5 except comprising 6% by weight of a compound represented by formula 1 b instead of the compound of formula 1 a.

(Example 7] A fiber softening composition was prepared in the same manner as Example 5 except comprising 6% by weight of a compound represented by formula 1 c instead of the compound of formula 1 a.

[Example 8] A fiber softening composition was prepared in the same manner as

Example 5 except comprising 6% by weight of a compound represented by formula 1 d instead of the compound of formula 1 a.

[Example 9] A fiber softening composition was prepared in the same manner as Example 5 except comprising 6% by weight of a compound represented by formula 1 e instead of the compound of formula 1 a.

[Example 10] A fiber softening composition was prepared in the same manner as Example 5 except comprising 6% by weight of a compound represented by formula 1 f instead of the compound of formula 1 a.

[Example 11] A fiber softening composition comprising 4% by weight of a compound represented by formula 1 d, 2% by weight of dialkylester type quaternary ammonium salt, 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0.1% by weight of fragrance was prepared.

[Example 12] A fiber softening composition was prepared in the same manner as Example 11 except comprising 2% by weight of oleylimidazoliniummethylsulfate, instead of dialkylester type quaternary ammonium salt.

[Example 13] A fiber softening composition comprising 6% by weight of a compound

represented by formula 1d and 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40 was prepared.

[Example 14] A fiber softening composition was prepared in the same manner as Example 13 except comprising 12% by weight of the compound represented by formula 1d.

[Example 15] A fiber softening composition comprising 18% by weight of a compound represented by formula 1 d, 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40,0. 2% by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0. 1% by weight of fragrance was prepared.

[Example 16] A fiber softening composition was prepared in the same manner as Example 15 except comprising 0.8% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40 instead of 0.5% by weight, and 0.2% by weight of a mixture of laurinic amide and polyoxyethylene whose molecular weight is 15 instead of 0.2% by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30.

[Example 17] A fiber softening composition comprising 6% by weight of a compound represented by formula 1g, 0. 5% by weight of a mixture of cured castor oil and

polyoxyethylene whose molecular weight is 40,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0. 1% by weight of fragrance was prepared.

[Example 18] A fiber softening composition was prepared in the same manner as Example 17 except comprising 6% by weight of a compound represented by formula 1 h instead of the compound of formula 1 g.

[Example 19] A fiber softening composition was prepared in the same manner as Example 17 except comprising 6% by weight of a compound represented by formula 1 i instead of the compound of formula 1 g.

[Example 20] A fiber softening composition was prepared in the same manner as Example 17 except comprising 6% by weight of a compound represented by formula 1 j instead of the compound of formula 1 g.

[Example 21] A fiber softening composition was prepared in the same manner as Example 17 except comprising 6% by weight of a compound represented by formula 1 k instead of the compound of formula 1 g.

[Example 22] A fiber softening composition was prepared in the same manner as Example 17 except comprising 6% by weight of a compound represented by formula 11 instead of the compound of formula 1 g.

[Example 23] A fiber softening composition comprising 4% by weight of a compound represented by formula 1 d, 2% by weight of dialkylester type quaternary ammonium salt, 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0. 1% by weight of fragrance was prepared.

[Example 24] A fiber softening composition was prepared in the same manner as Example 23 except comprising 2% by weight of oleylimidazoliniumsulfate instead of dialkylester type quaternary ammonium.

[Example 25] A fiber softening composition comprising 6% by weight of a compound represented by formula 1d and 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40 was prepared.

[Example 26] A fiber softening composition was prepared in the same manner as Example 25 except comprising 12% by weight of the compound represented by formula 1d.

[Example 27] A fiber softening composition comprising 18% by weight of a compound represented by formula 1d, 0.5% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40,0. 2% by weight of a mixture of

stearyl alcohol and polyoxyethylene whose molecular weight is 30,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0. 1% by weight of fragrance was prepared.

[Example 28] A fiber softening composition was prepared in the same manner as Example 27 except comprising 0.8% by weight of a mixture of cured castor oil and polyoxyethylene whose molecular weight is 40 instead of 0.5% by weight, and 0.2% by weight of a mixture of laurinic amide and polyoxyethylene whose molecular weight is 15 instead of 0.2% by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30.

[Comparative Example 2] A fiber softening composition comprising 6% by weight of distearyidimethyl quaternary ammonium salt as a cationic surfactant, 0.5% by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30,0. 5% by weight of ethyleneglycol, 0.03% by weight of calcium chloride and 0. 1 % by weight of fragrance was prepared.

[Comparative Examples 3 to 6] Fiber softening compositions of Comparative Examples 3 to 6 were prepared in the same manner as Comparative Example 2 except comprising 6% by weight of esteramide type quaternary salt, amidoesteramine quaternary ammonium salt, dialkylester type quaternary ammonium salt, and olelimidazoliummethylsulfate, respectively as a cationic surfactant.

[Experimental Example 1]

As for the fiber softening compositions of Examples 5 to 28 according to the present invention and Comparative Examples 2 to 6, their performance tests on normal products or condensed products were conducted as shown in Table 2 to 6, while being classified according to the standard content of pure materials, similarly to conventionally available products. In general, in normal products, the standard content of the pure material of fiber softener is 3 to 12% by weight, and in condensed products, it is almost 10 to 30% by weight, but when they are converted into a usage concentration in softening process at the stage of rinsing stage after washing, in both normal products and condensed products, 0.7 mA of pure material of the fiber softener per t of washing water, i. e. , same concentration, is used.

The performance tests of the fiber softeners of the present invention were conducted according to softening effect test, anti-electrostatic property test, dispersion-in-water test, bio-degradability test, and storage stability test and the results are shown in Table 2 to 6 below.

(Softening Effect Test) Towels made of 100% of cotton that are commercially available were washed five times using the standard usage of a normal detergent in washer and spun. The spun cotton towels were subjected to softening process in each rinsing water (bath ratio 1: 30,25 °C) in which the fiber softening compositions prepared from above Examples 5 to 28 are dissolved according to the standard of normal usage (6.7 m4/1 0 t washing water or 2.2 m. 0 t washing water), then spun, and conditioninged for 2 hours under conditions of 20 °C and 65% of

comparative humidity. Next, functional evaluations on the fiber softening composition of Examples 1 to 24 and Comparative Examples 2 to 6 were performed by experienced persons. The degree of touch is designated from minimum 1 point to 5 point as a softening score and the evaluations were repeated more than three times, and then softening effects are determined using their average value. Softening effects were evaluated as follows : highly excellent (a)) if the softening effect score is 4.5 or more, excellent (0) if it is 3.5 to 4.5, average (A) if it is 2.5 to 3.5, and poor (x) if it is less than 2.5.

(Anti-electrostatic Property Test (Half-life Determination) ) As for the samples, which were subjected to softening treatment in the same manner as the above softening effects test, and then conditioninged for 24 hours under conditions of 20 °C, 40% of comparative humidity, their leaking rates were measured by applying KS K-0555A test method using an electrostatic voltage (Satic Voltmeter) which is the product of Swiss Rothschild Company, to time during the period when the voltage falls down the half value after applying initial voltage 150 V, and the same procedures were repeated more than three times. Anti-electrostatic effects are evaluated as follows : highly excellent (O) if the leaking rate is 10 seconds or less, excellent (O) if it is 10 to 104, average if it is 104 to 105, and poor (x) if it is more than 105.

(Diameter of Dispersion Particles) In 0.1% aqueous solution of the fiber, the size of emulsifying particles was measured by diameter analysis device (MALVERN Company, mastersizer) using light scattering to determine dispersion in water.

(Bio-degradability Test) Bio-degradability was measure by OECD 301 D Closed bottle test. This test is to judge bio-degradability within 14 days from the date specimen is degraded, and if degradation values more than 60% come out, the specimen are regarded as being easily biodegradable.

The fiber softeners were tested at a concentration of 2 to 10 mg/e in aerobic aqueous media to measure their bio-degradability. In order to activity, as a comparison material, aniline, sodium acetate or sodium benzoate were used.

The bio-degradability was evaluated as follows : easily degradable (0) if the bio-degradability is 60% or more, average (A) if it is 30% or more, and poor (x) if it is 30% or less.

(Stability Test) The storage stability was evaluated under temperature conditions of 40 °C (A) and-10 C (B). At-10 C, freezing and thawing were conducted two times. The stability was evaluated as follows : excellent (0) if the stability maintenance period is 2 months or longer, average (A) if it is 1 month or longer, and poor (x) if it is 1 month or shorter.

The physicochemical experiment results regarding the fiber softening compositions of Examples 5 to 28 and Comparative Examples 2 to 6 are shown in Table 2 to 6 below.

Table 2 Ex. 5 Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 Softening Property 0 0 Anti-electrostatic O O O O O O ability Diameter of dispersion particle 0. 25 0. 21 0. 1 0. 22 1. 24 0. 1 (, am) Bio-degradability O O O O O O A O O O O O O Stability B O O O O O O B 000000 Table 3 Ex. 11 Ex. 12 Ex. 13 Ex. 14 Ex. 15 Ex. 16 Softening O O t t t O property Anti-electrostatic O O O O t O ability Diameter of dispersion 0. 58 1. 2 0. 33 0. 26 0. 82 1. 2 particle (um) Bio-degradability O O O O O O A O O O O O O Stability B O O O O O O Table 4 Ex. 17 Ex. 18 Ex. 19 Ex. 20 Ex. 21 Ex. 22 Softening O O O O o o property Anti-electrostatic O OO O O O O ability Diameter of dispersion 2. 1 2. 4 2. 6 1. 8 3. 2 2. 8 particle (, am) Bio-degradability O O O O O O A O O O O O O Stability B O O O O O O Table 5 Ex. 23 Ex. 24 Ex. 25 Ex. 26 Ex. 27 Ex. 28 Softening O O O O o o property Anti-electrostatic O O O O O O ability Diameter of dispersion 2. 9 3. 2 2. 2 2. 4 2. 9 3. 0 particle (, um) Bio-degradability O O O O O O A O O O O O O Stability B O O O O O O Table 6 C. Ex. 2 C. Ex. 3 C. Ex. 4 C. Ex. 5 C. Ex. 6 Softening Q o o 0 0 property Anti-electrostatic O O o OO OO ability Diameter of dispersion 5. 88 0. 77 4. 28 3. 64 4. 33 particle (lim) Bio-degradability x O x A A A O x O O O Stability B O O O O

As shown in Table 1 to 6 above, it is seen that the fiber softening compositions of the present invention according to Examples 5 to 28 were excellent in all five evaluation items as compared with the fiber softening composition according to Comparative Examples 2 to 6. Especially, in case of softening properties, as shown in Table 2, they were excellent when two or more non-ionic surfactants were used altogether.

[Example 29] 156 g (1.5 mol) of 2- (2-aminoethylamino) ethanol and 400 g (1.5 mol, average molecular weight 267) of stearic acid were amidified in four-sphere flask with a mechanical stirrer, thermometer, condenser and evaporating equipment at high temperature to a temperature of 165 °C for 5 hours while refluxing water produced during reaction. After the reaction was complete, the total amine

value was 104%, tertiary amine value was 8%, and acid value was 4%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S. Analysis (Official Method Te 2a-64,1987), and 265 g of ethanole was added to the amidoesteramine thus prepared, to which 133 g of ephichlorohydrine was slowed dropped to allow the reaction to proceed for 2 hours. The total amine value was 72%, and then 140 g of dimethylsulfate corresponding to the amount of the total amine value was added to allow the reaction to proceed at a temperature of 65 °C for 3 hours, and then the reaction was terminated by quaternarizing it.

[Example 30] 156 g (1.5 mol) of 2- (2-aminoethylamino) ethanole, 246 g (0.9 mol average molecular weight 267) of stearic acid and 164 g (0.6 mol, average molecular weight 282) of oleic acid were charged into in the apparatus identical to that used in Example 29 and were subjected to amidation at high temperature to a temperature of 165 °C for 5 hours while refluxing water produced during reaction. After the reaction was complete, the total amine value was 105.8%, tertiary amine value was 4.8%, and acid value was 3.4%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S.

Analysis (Official Method Te 2a-64,1987), and 150 g of ethanole was added to the amidoesteramine thus prepared, to which 140 g of ephichlorohydrine was slowed dropped to allow the reaction to proceed at a temperature of 65-70°C for 2 hour. The total amine value was 74.7%, and 150 g of dimethylsulfate corresponding to the amount of the total amine value was added to allow the

reaction to proceed at a temperature of 65 °C for 3 hours, and then the reaction was terminated by quaternarizing it.

[Example 31] A fiber softener was prepared according to conventional methods using the cationic surfactant prepared from Example 29.

[Experimental Example 2] The physicochemical properties of the fiber softeners (Example 31) prepared by using the cationic surfactant of the present invention and a prior fiber softening product (Comparative Example 7, Comparative Example 8) were compared and the results are shown in Table 7 below.

Table 7 Example 31 C. Example 7 C. Exmaple 8 Softening 8. 04 8. 22 7. 79 Silky 7. 42 7. 10 7. 10 Elastic 8. 41 8. 11 9. 01 Anti-electrostatic ability 24 36 32 Transparency (NTU) 50 150 130

[Example 32] 156 g (1.5 mol) of 2- (2-aminoethylamino) ethanol and 400 g (1.5 mol, average molecular weight 267) of stearic acid were added into four-sphere flask with a mechanical stirrer, thermometer, condenser and evaporating equipment and were subjected to amidation at high temperature to a temperature of 165 °C for 5 hours while refluxing water produced during reaction. After the reaction was complete, the total amine value was 104%, tertiary amine value was 8%, and

acid value was 4%. The analysis of the reactants regarding an amine value and acid value was conducted using A. O. C. S. Analysis (Official Method Te 2a-64, 1987), and 265 g of ethanole was added to the amidoesteramine thus prepared, to which 133 g of ephichlorohydrine was slowed dropped to allow the reaction to proceed for 2 hour. The total amine value was 72%, and 140 g of dimethylsulfate corresponding to the amount of the total amine value was added to allow the reaction to proceed at a temperature of 65 °C for 3 hours, and then the reaction was terminated by quaternarizing it to thereby prepare an amido ammonium salt of formula 2a as shown in Table 8 below. Thereafter, the same procedures were performed except changing alkyl groups, to prepare the compounds of formulae 2b to 2t as shown in Table 8 below.

Table 8 0 X Formula CNH (CH2) nN-W M- Formula 2 Y Y (wherein M is CH3SO4, and R2is CH3) Category R'x y R 3 n, m Formula Cured cow fat fatty (CH2) mOH CH2CHOH 2 Formula Cured cow fat fatty (CH2) mOH CH2CHOH 2 Formula Cured cow fat fatty (CH2) mOH H-2 Formula Cured pam fatty (CH2) mOH CH2CHOH _ 2 Formula Stearine fatty acid (CH2) mOH CH2CHOH 2 Formula 2f Oleinic acid fatty (CH2) mOH CH2CHOH- Formula Cured cow fat fatty (CH2) mOH CH2CHOH 2 Formula Cured cow fat fatty (CH2) mOH CH2CHOH 3 Cured cow fat fatty (CH2) mOC CH2CHOH Cured pam fatty Formula 2i 2 acid residue OR3 CH20H acid residue Formula 2j Cured cow fat fatty (CH2) mOC CH2CHOH Cured cow fat fatty 2 Formula Stearine fatty acid (CH2) mOC CH2CHOH Stearine fatty acid 2 2k residue OR3 CH2CI residue Oleinic acid fatty (CH2) mOC CH2CHOH Oleinic acid fatty Formula 21 2 acid residue OR3 CH2CI acid residue

[Example 33] A fiber softening composition was prepared by mixing 6 parts by weight of amido ammonium salt represented by formula 2a, 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40), 0.5 parts by weight of ethyleneglycol, and 0.5 parts by weight of fragrance.

[Example 34] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2b, instead of the amido ammonium salt represented by formula 2a.

[Example 35] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2c, instead of the amido ammonium salt represented by formula 2a.

[Example 36] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2d, instead of the amido ammonium salt represented by formula 2a.

[Example 37] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2e, instead of the amido ammonium salt represented by formula 2a.

[Example 38] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2f, instead of the amido ammonium salt represented by formula 2a.

[Example 39] A fiber softening composition was prepared by mixing 4 parts by weight of amido ammonium salt represented by formula 2d, 2 parts by weight of dialkylester type quaternary ammonium salt, 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40), 0. 5 parts by weight of ethyleneglycol, and 0.1 parts by weight of fragrance.

[Example 40] A fiber softening composition was prepared in the same manner as Example 39 except using 2 parts by weight of oleylimidazoliniummethylsulfate instead of dialkylester type quaternary ammonium salt used in Example 39.

[Example 41] A fiber softening composition was prepared by mixing 6 parts by weight of the compound represented by formula 2d, and 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40).

[Example 42] A fiber softening composition was prepared in the same manner as Example 41 except comprising 12 parts by weight of the compound represented by formula 2d.

[Example 43] A fiber softening composition was prepared by mixing 18 parts by weight of the compound represented by formula 2d, 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40), 0.2 parts by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30,0. 5 parts by weight of ethylene glycol, and 0.5 parts by weight of fragrance.

[Example 44] A fiber softening composition was prepared in the same manner as Example 43 except comprising 0.8 part by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40) instead of 0.5 parts by weight, and 0.2 parts by weight of a mixture of laurinic acid amide of ethylene oxide additive (additive mol 15) instead of 0.2 parts by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30.

[Example 45] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2g, instead of the amido ammonium salt represented by formula 2a.

[Example 46] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2h, instead of the amido ammonium salt represented by formula 2a.

[Example 47] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2i, instead of the amido ammonium salt represented by formula 2a.

[Example 48] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2j, instead of the amido ammonium salt represented by formula 2a.

[Example 49] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by formula 2k, instead of the amido ammonium salt represented by formula 2a.

[Example 50] A fiber softening composition was prepared in the same manner as Example 33 except comprising 6 parts by weight of compound represented by

formula 2E, instead of the amido ammonium salt represented by formula 2a.

[Example 51] A fiber softening composition was prepared by mixing 4 parts by weight of amido ammonium salt represented by formula 2d, 2 parts by weight of dialkylester type quaternary ammonium salt, 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40), 0.5 parts by weight of ethyleneglycol, and 0.1 parts by weight of fragrance.

[Example 52] A fiber softening composition was prepared in the same manner as Example 51 except using 2 parts by weight of oleylimidazoliniummethylsulfate instead of dialkylester type quaternary ammonium salt used in Example 51.

[Example 53] A fiber softening composition was prepared by mixing 6 parts by weight of the compound represented by formula 2d, and 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40).

[Example 54] A fiber softening composition was prepared in the same manner as Example 53 except comprising 12 parts by weight of the compound represented by formula 2d.

[Example 55] A fiber softening composition was prepared by mixing 18 parts by weight of the compound represented by formula 2d, 0.5 parts by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40), 0.2 parts by

weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30,0. 5 parts by weight of ethylene glycol, and 0.1 parts by weight of fragrance.

[Example 56] A fiber softening composition was prepared in the same manner as Example 55 except comprising 0.8 part by weight of a mixture of cured castor oil and ethylene oxide additive (molecular weight 40) instead of 0.5 parts by weight, and 0.2 parts by weight of a mixture of laurinic acid amide of ethylene oxide additive (additive mol 15) instead of 0.2 parts by weight of a mixture of stearyl alcohol and polyoxyethylene whose molecular weight is 30.

[Comparative Example 9] A fiber softening composition was prepared by mixing 6 parts by weight of distearyldimethyl quaternary ammonium salt, a mixture of stearyl alcohol and ethylene oxide additive (additive mol 30 mol), 0.5 parts by weight of ethylene glycol, and 0.5 parts by weight of fragrance.

[Comparative Example 10] A fiber softening composition was prepared in the same manner as Comparative Example 9 except using esteramide type quaternary salt instead of distearyidimethyl quaternary ammonium salt used in Comparative Example 9.

[Comparative Example 11] A fiber softening composition was prepared in the same manner as Comparative Example 9 except using amidoesteramine quaternary salt instead of distearyidimethyl quaternary ammonium salt used in Comparative Example 9.

[Comparative Example 12] A fiber softening composition was prepared in the same manner as Comparative Example 9 except using dialkylester type quaternary salt instead of distearyldimethyl quaternary ammonium salt used in Comparative Example 9.

[Comparative Example 13] A fiber softening composition was prepared in the same manner as Comparative Example 9 except using oleylimidazoliniummethylsulfate instead of distearyldimethyl quaternary ammonium salt used in Comparative Example 9.

[Experimental Example 3] Softening effects, anti-electrostatic ability, diameter of dispersion particles, bio-degradability, and stability were measured using the fiber softening compositions prepared from Examples 33 to 56 and Comparative Examples 9 to 13 as follows : (Softening Effects) (Softening Effect Test) Towels made of 100% of cotton that are commercially available were washed five times using the standard usage of a normal detergent in washer and spun. The spun cotton towels were subjected to softening process in each rinsing water (bath ratio 1: 30,25 °C) in which the fiber softening compositions prepared from above Examples 33 to 56 and Comparative Examples 9 to 13 are dissolved according to the standard of normal usage (6.7 mE/10 t washing water or 2.2 mE/10 t washing water), then spun, and conditioninged for 2 hours under conditions of 20 °C and 65% of comparative humidity. Next, functional

evaluations on the fiber softening composition of Examples 33 to 56 and Comparative Examples 9 to 13 were performed by experienced persons. The degree of touch is designated from minimum 1 point to 5 point as a softening score and the evaluations were repeated more than three times, and then softening effects are determined using their average value. As the standard of evaluating softening properties, pure towel softening-treated with the fiber softening composition of Comparative Example 9 was used. Softening effects were evaluated according to Table 9 below.

Table 9 Softening Effect Score Evaluation 4. 5 or more highly excellent 3. 5-4. 5 Excellent 2. 5 ~3. 5 Average less than 2. 5 Poor (Anti-electrostatic Property Test (Half-life Determination) ) As for the samples, which were subjected to softening treatment in the same manner as the above softening effects test, and then conditioninged for 24 hours under conditions of 20 °C, 40% of comparative humidity, their leaking rates were measured by applying KS K-0555A test method using an electrostatic voltage (Satic Voltmeter) which is the product of Swiss Rothschild Company, to time during the period when the voltage falls down the half value after applying initial voltage 150 V, and the same procedures were repeated more than three times. Anti-electrostatic effects are evaluated according to Table 10 below.

Table 10 Anti-electrostatic Property Evaluation Leaking rate 10 sec. or less Highly excellent Leaking rate 10~ 104 sec. Excellent Leaking rate 104~105 sec. Average Leaking rate 105 sec. or more Poor

(Diameter of Dispersion Particles) In 0. 1% aqueous solution of the fiber softener of Examples 33 to 56 and Comparative Example 9-13, the size of emulsifying particles was measured by diameter analysis device (MALVERN Company, mastersizer) using light scattering to determine dispersion in water.

(Bio-degradability Test) Bio-degradability was measure by OECD 301 D Closed bottle test. This test is to judge bio-degradability within 14 days from the date specimen is degraded, and if degradation values more than 60% come out, the specimen are regarded as being easily biodegradable.

The fiber softeners of Examples 33 to 56 and Comparative Examples 9-13 were tested at a concentration of 2 to 10 mg/t in aerobic aqueous media to measure their bio-degradability. In order to activity, as a comparison material, aniline, sodium acetate or sodium benzoate were used. The bio-degradability was evaluated according to Table 11 below.

Table 11 Bio-degradability Evaluation Bio-degradable rate 60 % or more Easily degradable Bio-degradable rate 30-60 % Average Bio-degradable rate 30 % or less Poor

(Stability Test) The storage stability was evaluated using the fiber softener of Examples 33 to 56 and Comparative Examples 9-13 under temperature conditions of 40 °C (A) and-10 C (B). At-10 C, freezing and thawing were conducted two times.

The stability was evaluated according to Table 12 below.

Table 12 Stability Evaluation Maintenance period more than 2 months Excellent Maintenance period 1-2 months Average Maintenance period less than 1 month Poor

The physicochemical experiment results regarding the fiber softening compositions of Examples 33 to 56 and Comparative Examples 9 to 13 are shown in Table 13 below.

Table 13 Softeni Stability ng...,.. Diameterof g Anti-electrost iameter of gio-degr Category proper dispersion particle ty 0 (l ty-rr °) All Ex. 33 0 0. 30 O O O Ex. 34 (a 0. 31 O O O Ex. 35 O (Q) 0. 32 O O O Ex. 36 O 0. 23 O O O Ex. 37 0. 25 0 0 0 Ex. 38 0. 42 0 0 0 Ex. 39 O O 0. 22 O O O Ex. 40 (U) @ 0. 18 O O O Ex. 41 0. 33 0 0 0 Ex. 42 0. 25 o o 0 Ex. 43 0. 24 0 0 0 Ex. 44 (a 0. 22 0 0 0 Ex. 45 0. 31 0 0 0 Ex. 46 OO a0 0. 30 O O O Ex. 47 0 1. 84 0 0 0 Ex. 48 @ @1. 22000 Ex. 49 @ @1. 09000 Ex. 50 O (U) 2. 02 O O O Ex. 51 0. 84 0 0 0 Ex. 52 0. 72 0 0 0 Ex. 53 O (g) 0. 58 O O O Ex. 54 0. 82 0 0 0 Ex. 55 0. 98 0 0 0 Ex. 56 O (U) 0. 82 O O O C. Ex. 9 @ @5. 88x Q Q C. Ex. 10 @ @0. 770 x Q C. Ex. 11 O O 4. 28 x O A C. Ex. 12 O O 3. 64 o O O C. Ex. 13 O a 4. 33 o

Through Table 13 above, it is seen that the fiber softening compositions according to Examples 33 to 56 comprising the amido ammonium salt represented by formula 1 having an amide group and a hydroxyl group within

molecules of the present invention have excellent properties in softening properties, anti-electrostatic properties, diameter of dispersion particles, bio-degradability and stability.

As described in the above, the cationic surfactants of formulae 1 and 2 prepared according to the methods of the present invention have excellent solubility in water by possessing an amide group or a hydroxyl group, which is hydrophilic, within molecules, and have very excellent physicochemical characteristics such as softening properties, anti-electrostatic properties and dispersion properties.

Also, the fiber softening composition of the present invention has excellent uniform adhesion effects onto clothes, and thus is excellent in softening properties, anti-electrostatic effects, and absorption as well as excellent in storage stability, dispersion in water, and bio-degradability, at the same time.