BACKGROUND OF THE INVENTION Microbes, and especially bacteria, are known to cause diseases and/or infections in humans and other organisms with whom they come in contact. To reduce the likelihood that microbes will come in contact with people, it is known to wash items with soap and water. Such washing may reduce the concentration of microbes on the surface of hands, clothing, and the like. Furthermore, it is known that certain substances having an anti-microbial efficacy (e. g. antibiotics) may actually kill microbes, and therefore may be used to help sterilize items, such as surgical equipment, which need to be free of microbes. However, as anti-microbial substances such as antibiotics have become increasingly common, it has been found that microbes are becoming increasingly resistant to these traditional antibiotics. Recently, bacteria have even developed resistance, and even immunity, to multiple antibiotics.

In addition, consumers are becoming more and more concerned with exposure to microbes which they perceive as"dirty"or which may potentially cause disease. Thus, it is increasingly desirable to provide consumer products which remove or kill microbes from everyday items such as clothing, hard surfaces, and skin. Such consumer products have varying degrees of actual

anti-microbial efficacy. Consumers may especially desire both a short-term and a long-term anti-microbial benefit from a product.

Accordingly, the need exists for a novel and improved compound which has an anti-microbial effect. The need also exists for an improved consumer product containing such a compound.

SUMMARY OF THE INVENTION The present invention relates to a polymer selected from the group of a linear polymer, a branched polymer, and a mixture thereof. The linear polymer has the structure: wherein each R, is independently a C2-C6 alkyl, each R2 is independently a C6-C22 alkyl, and each R3 is independently aC,-C, 2alkyl. In the linear polymer, a is from about 1 to about 20, b is about 1 to about 20, c is about 1 to about 50, and each X~ is an anion. The branched polymer has the structure: wherein each A independently has the structure: wherein each B independently has the structure: wherein each R4 independently has the structure: wherein each R, is independently a C2-C6 alkyl, wherein each Y is independently a nitrogen or an oxygen. If Y is a nitrogen, any substitutions on the nitrogen are selected from the group consisting of H, R3, and R4, wherein each R3 is independently H or Cl-C, 2 alkyl. Each p is independently from about 1 to about 20, and the total of all p in the branched polymer is from about 2 to about 40.

There is at least one nitrogen in A, and at least one nitrogen in B. Furthermore, at least one nitrogen in A is quaternized and at least one nitrogen in B is quaternized. Each X-is an anion, a is from about 1 to about 20, b is about 1 to about 20, c is about 1 to about 50, each d is independently 1 or 2, and e is a number equal to the number of quaternized nitrogens in A and B.

It has now been found that the novel polymer described herein may surprisingly provide one or more benefits such as an anti-microbial effect, a hair conditioning benefit, a fabric softening benefit, a moisturizing benefit, and/or a lubrication benefit when included in a consumer product. Preferably, the polymer herein provides an anti-microbial effect in combination with one or more of the above-mentioned benefits. The polymer herein may be especially useful in a hair care composition, a laundry detergent composition, a hard surface cleaning composition, a deodorizing composition, and/or a sanitizing composition, as the multiple cationically-charged groups provide a strong attraction to negatively- charged surfaces. Furthermore, as such polymers are novel, it is likely that they will be extremely effective against microbes, especially bacteria, as microbes will not have had a chance to develop resistance to these novel polymers.

These and other features, aspects, advantages, and variations of the present invention, and the embodiments described herein, will become evident to those skilled in the art from a reading of the present disclosure with the appended claims, and are covered within the scope of these claims.

DETAILED DESCRIPTION OF THE INVENTION All percentages, ratios and proportions herein are by weight of the final hair care composition, unless otherwise specified. All temperatures are in degrees Celsius (°C) unless otherwise specified. All documents cited are incorporated herein by reference in their entireties. Citation of any reference is not an admission regarding any determination as to its availability as prior art to the claimed invention.

As used herein, the term"alkyl"means a hydrocarbon moiety which is straight, cyclic, or branched, and saturated or unsaturated. Unless otherwise specified, alkyl moieties are preferably saturated or unsaturated with double bonds, preferably with one or two double bonds.

As used herein, the term"anti-microbial"means that the indicated substance decreases the concentration of microbes, either immediately, or over a period of time. This may occur, for example, by killing existing microbes, by reducing microbe numbers below the level required for a sustainable population, and/or by inhibiting microbial growth and/or reproduction.

As used herein, the term"microbe"indicates a bacteria, a fungus, a protozoa and/or other microorganisms, especially bacteria and fungus, and more especially gram negative bacteria and gram positive bacteria.

POLYMER The novel polymer herein is either a linear polymer, a branched polymer, or a mixture thereof. The polymer has a plurality of quaternized nitrogen moieties, wherein at least two nitrogen moieties are separated by at least one alkoxy group. As used herein, the term"linear polymer"means that any side groups attached to the main polymer chain are unsubstituted alkyl groups, such as R2 and R3, which are described below. In addition, The linear polymer useful herein has the formula: wherein each R, is independently a C2-C6 alkyl, preferably a C2-C4 alkyl, and more preferably a C2H4 alkyl, or a straight-chain C3H6 alkyl. Each R2 is independently a C6-C22 alkyl, preferably a Cg-Cis aikyt. Furthermore, each R3 is independently a C1-C12 alkyl, preferably a C1-C12 straight chain alkyl, and more preferably a saturated C1-C4 straight chain alkyl. Thus, a"linear polymers defined herein, may contain unsubstituted alkyl groups such as R2 and R3 which are attached to a quaternized nitrogen moiety.

In the above linear polymer formula, a is from about 1 to about 20, preferably from about 1 to about 10, and more preferably from about 3 to about 7; b is about 1 to about 20, preferably from about 1 to about 10, and more preferably from about 3 to about 7; c is about 1 to about 50, preferably from about 1 to about 25, and more preferably from about 1 to about 20; and each X-is an anion, where the total charge of all C is sufficient to balance the charge of the

molecule. Thus, X-may be one or more anions, which have a single negative charge, or one or more multiply-valent anions. Preferably X~ is a halide, a sulfate, an organosulfate, or a mixture thereof, and more preferably a chloride, a bromide, a methylsulfate, or a mixture thereof. In a highly preferred embodiment, the number quaternized nitrogens in the linear polymer (as represented by a + b) is from about 6 to about 14, as such linear polymers are more easily formed by the processes described herein.

The branched polymer useful herein has the formula : wherein each A independently has the structure: and wherein each B independently has the structure: In the above branched polymer formula, each R4 independently has the structure: -H<BR> , or H.

Each Y is independently a nitrogen or an oxygen. If Y is a nitrogen, it may be a charged or uncharged, substituted and/or quaternized nitrogen. Any substitutions on a Y which is a nitrogen are selected from the group consisting of H, R3, and R4, wherein R3 is defined as above in the linear polymer. Each p is independently from about 1 to about 20, preferably from about 1 to about 10, and more preferably form about 1 to about 8, while the total of all p in the branched polymer is from about 2 to about 40, preferably from about 2 to about 20.

There is at least one nitrogen in A, and at least one nitrogen in B.

Furthermore, at least one nitrogen in A is quaternized and at least one nitrogen in B is quaternized, preferably from about 50% to about 100% of the nitrogens in A are quaternized and from about 50% to about 100% of the nitrogens in B are quaternized, and more preferably from about 100% of the nitrogens in A are quaternized and from about 100% of the nitrogens in B are quaternized. Each Ri, X-, a, b, and c is defined as described above for the linear polymer, while each d is independently 1 or 2. Generally, such a polymer may be described as

a polyamine ether block polymer containing a plurality of quaternized nitrogen groups. Typically, in the branched polymer, at least one R4 group has the structure: and preferably at least one R4 group in A and at least one R4 group in B has the structure: While the branched polymer herein must contain at least one quaternized nitrogen in A and at least one quaternized nitrogen in B, it is recognized that not all nitrogens need to be quaternized. Thus, the branched polymer may comprise a mixture of quaternized nitrogens and unquaternized nitrogens. Specifically, the ratio of quaternized nitrogens to unquaternized nitrogens may be adjusted as desired via, for example, adjusting the amount of quaternizing agent employed in the process described herein. In a highly preferred embodiment, the branched polymer has from about 2 to about 20 quaternized nitrogens therein.

The polymer herein may provide one or more benefits when included in a consumer product, such as, for example, an anti-microbial effect, and/or a fiber (e. g., hair or fabric fibers) conditioning or softening benefit.

Without intending to be limited by theory, it is believed that the present polymer, and especially the preferred embodiments described herein, may provide an especially effective anti-microbial effect against a microbe, such as a gram-positive bacteria, a gram-negative bacteria, a fungus, a protozoa, and/or a mixture thereof, preferably a gram-positive bacteria, a gram-negative bacteria and/or a fungus, and more preferably a gram-positive bacteria, a gram-negative bacteria. It is believed that the linear polymer and the branched polymer herein provide such an anti-microbial effect by one or more mechanisms such as disruption of cell membranes and/or disruption of cell processes by penetrating the cell membrane and/or the cell. This in turn may kill existing microbes, reduce microbe numbers below the level required for a sustainable population, and/or inhibit microbial growth and/or reproduction.

Without intending to be limited by theory, it is believed that a fiber conditioning or softening benefit may result from, for example, a moisturizing or lubricating effect when the polymer is applied to a fiber, such as a fabric and/or

hair. The polymers, by virtue of their quaternized nitrogen groups and/or their ether group (s), have a particularly strong affinity towards such fibers, and especially negatively charged fibers. The polymer may therefore be attracted to, or even penetrate fibers to provide a conditioning or lubricating benefit; i. e., the polymer may provide a lubricating effect by smoothening the surface of the fiber.

In addition to being attracted to the fibers, the polymers, especially those having a plurality of ether groups, also have a strong affinity towards water. Thus, the polymers may serve to bind water to the fiber to provide a noticeable moisturizing benefit. The polymer may also reduce wrinkling by disrupting inter-fiber hydrogen bonds in, for example, a fabric article. The polymer may also reduce or negate the static charge of a fiber to reduce static cling, and/or fly-away hair, which in turn makes the fabric/hair more manageable.

CONSUMER PRODUCT COMPOSITION The polymer may be included in a consumer product composition in an effective amount. As used herein, the term"effective amount"varies according to many factors such as product category, the desired benefit sought, the method for applying the polymer to achieve the desired benefit, etc. Generally, for consumer product compositions, an effective amount of polymer to provide one or more desirable benefits will be at least about 0.001%, preferably from about 0.001% to about 50%, more preferably from about 0.01% to about 30%, and even more preferably from about 0.05% to about 15%, by weight of the final consumer product composition. It is recognized that a consumer product compositions for direct application typically requires a lower amount of the polymer to achieve the desired benefit, while a consumer product composition which is applied indirectly, or in a diluted form typically requires a higher amount of the polymer to achieve the desired benefit.

Without intending to be limited by theory, it is believed that the polymer herein is stable under typical consumer product manufacturing, and storage conditions (e. g., temperature, humidity), and may therefore provide benefits over an extended period of time. Thus, the polymer herein may be especially useful in conditions where other ingredients are inadequate, for example, in a liquid composition. Furthermore, the polymer herein is typically compatible with a wide variety of ingredients typically found in a consumer product composition. Thus, a

non-limiting example of a preferred consumer product composition includes an antiseptic or disinfecting composition, a fabric detergent and/or fabric conditioner, a fabric treatment composition, a hair shampoo and/or hair conditioner, a hand, body, and/or toilet soap, a hard surface cleaner, etc.

Furthermore, such a consumer product composition is not limited by any particular physical form, and thus may be a liquid, a gel, a spray, a foam, a solid, a powder, or even an aerosol, as appropriate. Thus, a carrier is present in the consumer product composition to deliver the polymer to the intended target and/or surface. As used herein, the term"carrier"indicates any substance or composition which is not the polymer herein, and which provides a delivery mechanism to apply the polymer, either directly or indirectly, to the targeted surface and/or item. Thus, the carrier may contain additional active ingredients which provide additional benefits, or may be completely inert, as desired. In addition, the carrier may be in any physical form, as appropriate. The polymer may be included in addition to, and/or in place of, any already-present anti- microbially-effective agent (s) and/or conditioning compounds within the carrier.

The antiseptic or disinfecting composition which may act as a carrier herein is typically either alcohol-or water-based, and typically also contains a surfactant, a dye, a perfume, etc. Preferred examples of the antiseptic or disinfecting composition which may act as a carrier for the polymer herein are described in, for example, U. S. Patent No. 6,048,836 to Romano, et al., issued on April 11, 2000; U. S. Patent No. 5,403,587 to McCue and Smialowicz, issued on April 4,1995; U. S. Patent No. 5,174,990 to Douglas, Issued December 29, 1992; U. S. Patent No. 5,135,623 to Dziabo and Ripley, issued on August 4,1992; U. S. Patent No. 4,941,989 to Kramer and Snow, issued on July 17,1990; U. S.

Patent No. 4,589,994 to Moseman, issued on May 20,1986; and U. S. Patent No.

4,568,517 to Kaspar, et al., issued on February 4,1986.

Preferred examples of the fabric detergent and/or fabric conditioner which may act as a carrier for the polymer herein are typically in a solid, liquid, or gel form. A fabric detergent composition typically contains one or more anionic, nonionic, cationic, or amphoteric surfactants, a builder, a chelant, a perfume, a soil-dispersing aid, an anti-redeposition aid, a dye-transfer inhibitor, and/or other ingredients known in the art. A fabric conditioner may also contain similar ingredients, as well as a fabric softening active, an anti-static active, etc.

Examples of such a fabric detergent and/or a fabric conditioner are described in, for example, PCT Patent Application No. U. S. 00/00839 to Showell, et al., filed on January 13,2000; PCT Patent Application U. S. 99/15056 to Bryant, et al., filed on July 1,1999; U. S. Patent No. 5,916,862 to Morelli, et al., issued on June 29, 1999; WO 99/09126 to Bettiol, et al., published on February 25,1999; U. S.

Patent 5,747,443 to Wahl, et al., issued May 5,1998; U. S. Patent No. 5,565,145 to Watson, et al., issued on October 15,1996; WO 95/33044 to Vinson, et al., published on December 7,1995; U. S. Patent No. 5,470,507 to Fredj, et al., issued on November 28, 1995; U. S. Patent No. 5,466,802 to Panadiker, et al., issued on November 14,1995; U. S. Patent No. 5,460,752 to Fredj, et al., issued on October 24,1995; U. S. Patent No. 5,458,810 to Fredj, et al., issued on October 17,1995; and U. S. Patent No. 5,458,809 to Fredj, et al., issued on October 17,1995; U. S. Patent 4,375,416 to Crisp, et al., issued March 1,1983; U. S. Patent 4,291,071 to Harris, et al., issued September 22,1981; and U. S.

Patent 4,062,647 to Storm and Nirschl, issued December 13,1977.

Preferred examples of the fabric treatment composition which may act as a carrier for the polymer herein include a bleaching composition, a finishing composition, etc. A bleaching composition typically contains either a chlorine bleach and/or an oxygen bleach, and is typically added to a fabric article in diluted form. Highly preferred examples of a bleaching composition useful herein are described in, for example, U. S. Patent. No. 5,559,090 to Scialla and Cardola, issued on September 24,1996; U. S. Patent. No. 5,536,438 to Scialla, et al., issued on July 16,1996; WO 95/21122 to Rapisarda, et al., published on August 10,1995; U. S. Patent No. 6,037,317 to Rapisarda, et al., issued on March 14, 2000; WO 95/34621 to Scialla, et al., published on December 21,1995; U. S.

Patent No. 5,929,012 to Del Duca, et al., issued on July 29,1999; U. S. Patent No. 5,910,473 to Aldano, et al., issued on June 8,1999; U. S. Patent No.

6,001,794 to Del Duca, et al., issued on December 14,1999; WO 97/02332 to Masotti, et al., published on January 23,1997; WO 97/22407 to Bianchetti, et al., published on June 26,1997; U. S. Patent No. 5,968,885 to Del Duca, et al., issued on October 19,1999; U. S. Patent No. 5,641,739 to Kott and Willey, issue don June 24,1997; WO 97/47558 to Del Duca, et al., published on December 18, 1997; U. S. Patent No. 6,019,797 to Del Duca, et al., issued on February 1,2000; WO 98/11191 to Scialla, et al., published on March 19,1998; WO 98/11189 to

Burns, et al., published no March 19,1998; WO 97/32962 to Del Duca, et al., published on September 12,1997; WO 98/11192 to Masotti, et al., published on March 19,1998; WO 98/18893 to Del Duca, et al., published on May 7,1998; WO 98/22560 to Bertacchi, et al., published on May 28,1998; WO 98/33879 to Del Duca, et al., published on August 6,1998; WO 99/18181 to Del Duca, et al., published on April 15,1999; WO 99/18179 to Del Duca, et al., published on April 15,1999; WO 99/18183 to Del Duca, et al., published on April 15,1999; WO 99/24540 to Del Duca, et al., published on May 20,1999; WO 99/63033 to Del Duca, et al., published on December 19,1999; WO 00/12666 to Campestrini, et al., published on March 9,2000; and WO 00/15743 to Briatore, et al., published on March 23,2000.

The finishing composition which may act as a carrier for the polymer herein is typically applied to a fabric article as one of the last steps prior to use (e. g., wearing) and/or in-between uses. The finishing composition provides the fabric article with one or more desirable properties such as crispness, wrinkle reduction, shape maintenance, color enhancement, whiteness enhancement, improved in-wear comfort, malodor reduction/prevention, stain protection, a desirable scent, fiber integrity maintenance, etc. The finishing composition is typically an ironing composition, a fabric styling composition, a wrinkle reduction composition, a stain prevention composition, or a combination thereof. Preferred finishing compositions useful herein include those described in U. S. Patent No.

6,033,679 to Woo, et al., issued on March 7,2000; U. S. Patent No. 6,001,343 to Trinh, et al., issued on December 14,1999; U. S. Patent No. 5,997,759 to Trinh, et al., issued on December 7,1999; and U. S. Patent No. 5,942,217 to Woo, et al., issued on August 24,1999.

In a highly preferred embodiment, the finishing composition acts as a fabric refresher composition and/or a home dry cleaning composition which, respectively, reduces odors, and/or reduces the need for dry cleaning of the fabric article. Highly preferred fabric refresher compositions are include those described in, U. S. Patent No. 5,714,137 to Trinh, et al., issued on February 3, 1998; U. S. Patent No. 5,593,670 to Trinh, et al., issued January 14,1997; and U. S. Patent No. 5,939,060 to Trinh, et al., issued on August 17,1999. The polymer herein may also be included in a home dry cleaning apparatus or kit as described in, for example, U. S. Patent No. 5,789,368 to You, et al., issued on

August 4,1998; and U. S. Patent No. 5,762,648 to Yeazell, issued on June 9, 1998. A polymer having an anti-microbial effect is especially preferred in the above finishing compositions.

A hair shampoo typically contains a surfactant, preferably an anionic and/or nonionic surfactant, a humectant, a perfume, water, a dye, and/or other optional ingredients. A hair conditioner typically contains a silicone and/or cationic hair conditioning compound, in addition to any of the ingredients described for a hair shampoo. A preferred hair shampoo and/or hair conditioner which may act as a carrier for the polymer herein is described in, for example, U. S. Patent No. 5,955,066 to Sako, et al., issued on September 21,1999; and PCT Publication WO 97/31616 A1 to Mitsumatsu and Nakamura, published on September 4,1997.

A hand, body, and/or toilet soap and/or wipe is typically formulated for mild cleaning of the human body, and thus contains a mild surfactant, typically an anionic surfactant, a moisturizing agent, and other typical ingredients. A preferred hand, body, and/or toilet soap and/or wipe which may act as a carrier for the polymer herein is described in, for example, U. S. Patent No. 6,028,043 to Glenn, et al., issued on February 22,2000; WO 99/57238 A1 to Gu, published on November 11,1999; WO 98/55094 A1 to Beers, et al., published on December 10,1998; European Patent Application 556 546 A2 to Widulle, et al., published on August 25,1993; European Patent Application 555 634 A2 to Widulle, et al., published on August 18,1993; U. S. Patent No. 4,939,284 to Degenhardt, issued on July 3,1990; U. S. Patent No. 4,847,072 to Bissett, et al., issued on July 11, 1989; and U. S. Patent No. 4,820,698 to Degenhardt, issued on April 11,1989.

A hard surface cleaner typically contains a surfactant, and may contain an abrasive for cleaning dishes, ceramic, wood, flooring, walls, windows, etc. A preferred hard surface cleaner which may act as a carrier for the polymer herein is described in, for example, U. S. Patent No. 5,562,850 to Woo, et al., issued on October 8,1996; WO 97/44417 A1 to Askew, et al., published on November 27, 1997; and WO 97/25396 to Cardola, et al., published on July 17,1997.

POLYMER SYNTHESIS

The polymers of the present invention may be prepared by a variety of synthetic routes; preferably the polymer is prepared according to one of the two synthetic routes described, below.

In the first synthetic route, an activated ether, preferably an activated polyether, is provided. The activated ether is an ether compound containing a sulfonic ester group, a halogen group, and/or an epoxy group which has been substituted for a hydroxyl group. Preferably, the activated ether is an ether compound having its terminal hydroxyl group, or at least one pendant hydroxyl group, preferably its terminal hydroxyl group, substituted with a sulfonic ester or a halogen, preferably a tosyl or a mesyl sulfonic ester group. Alternatively, the activated ether may be any linear or branched ether compound having a halogen group and/or an epoxy group, wherein any other existing functional groups are non-reactive with the below-mentioned cyclic iminoether. The epoxy group is preferably a glycidyl-type epoxy group or an oxirane-type epoxy group. The activated ether useful herein may be either purchased, or synthesized.

Examples of commercially-available activated ethers include 2-chloroethyl methane sulfonate, available from Aldrich (Milwaukee, Wisconsin, USA; CAS # [3570-58-9] ; Aldrich Catalog No. C4,170-3) and bis-2-chloroethyl ether (Milwaukee, Wisconsin, USA; CAS # [111-44-4]; Aldrich Catalog No. C4, 113-4).

Alternatively, the activated ether may be synthesized by providing an ether compound (either linear or branched), preferably a polyether compound, which contains at least one reactive hydroxyl group, preferably a terminal, reactive hydroxyl group, a halogen group, and/or an epoxy group. However, any other existing functional groups should be non-reactive with the below-mentioned activating agents, and the below-mentioned cyclic iminoethers in the synthesis conditions described. Preferred ether compounds useful herein include commonly available dihydroxy-terminated poly (oxyalkylene) ethers.

An activating agent is also provided which is selected from the group consisting of R-SO3 (hal), R-P (hal) 3, R-P (hal) 5, and R-SO2 (hal) 2 or mixtures thereof, wherein R is an alkyl group, and each hal is a halide independently selected from chloride, bromide, and iodide. Preferable activating agents are tosyl chloride and mesyl chloride.

An anhydrous, inert solvent is also provided. A preferred anhydrous, inert solvent is absolute (hereinafter referred to"abs.") tetrahydrofuran (hereinafter

referred to as"THF"), abs. benzene, abs. toluene, abs. triethylamine, abs. pyridine, and a mixture thereof. Preferably the anhydrous, inert solvent further contains a Lewis base. A highly preferred Lewis base includes abs. triethylamine, abs. pyridine, dimethylamino pyridine, and 1,8-diazabicyclo [5.4.0]- 7-undecene. Absolute triethylamine and abs. pyridine act both as an anhydrous, inert solvent and a liquid Lewis base, and are thus highly preferred. More preferably, the absolute, inert solvent contains a Lewis base at a level at least equal to the stoichiometric amount of the activating agent, as it provides a significantly improved yield. Even more preferably, the anhydrous, inert solvent contains: a volatile solvent such as abs. benzene, abs. toluene, abs. THF and mixtures thereof, and a Lewis base, such as abs. triethylamine, abs. pyridine, and mixtures thereof, at a level at least equal to the stoichiometric amount of the activating agent.

The ether compound is then activated with the activating agent in the anhydrous, inert solvent, with or without the optional Lewis base, to form an activated ether, preferably an activated polyether. The activation reaction is typically carried out at from about 5 °C to about 40 °C, and at atmospheric pressure.

In a preferred embodiment, the activated ether comprises a terminal halogen. In such cases, the activated ether comprising a terminal halogen may be used directly in a ring-opening polymerization reaction, without the need for an activating agent.

Ring-Opening Polymerization The activated ether, preferably the activated polyether, is preferably polymerized through a ring-opening polymerization reaction. This may be accomplished by providing a cyclic iminoether and reacting the activated ether with the cyclic iminoether to form a polyamide ether. The preferred cyclic iminoether useful herein is selected from the group consisting of 2-substituted-2- oxazoline, 2-substituted-5,6-dihydro-1,3-oxazine, and a mixture thereof, more preferably 2-Z'-2-oxazoline, 2-Z'-oxazine, and a mixture thereof, wherein Z'is a hydrogen, alkyl, or fluorocarbon having 1 to 10 carbons, phenyl and benzyl ; even more preferably 2-alkyl-2-oxazoline, and a mixture thereof, wherein the alkyl contains from 1 to 3 carbons.

The tosyl group, mesyl group, and/or halide group of the activated ether is a known leaving group which is dislodged upon attack by various nucleophilic monomers. Thus, the activated ether is used as a macromolecular initiator for the synthesis of a block copolymer through nucleophilic reaction toward the tosylat or mesylate ester group and/or the halide group by the cyclic iminoether which acts as a nucleophilic monomer. The polyamide ether, is thus obtained by a nucleophilic-substitution reaction which concentrates polyamide moieties at the locations on the polymer which were previously occupied by the above- mentioned leaving group (s). Preferably, the polyamide ether is a polyamide polyether.

Suitable mediums for carrying out this synthesis include anhydrous, inert solvent described above. Preferably the anhydrous, inert solvent contains a Lewis base therein to facilitate the reaction, and/or to improve yields. More preferably, the medium contains Lewis base at a level at least equal to the stoichiometric amount of the activated ether. It has been found that the presence of this amount of Lewis base significantly raises the conversion yield of the activated ether to the desired polyamide ether. Thus, the number of amide moieties of the present polymers may be controlled with significantly improved precision to provide the targeted polymer in a relatively high yield. Even more preferably, the anhydrous, inert solvent contains: a volatile solvent such as abs. acetonitrile, abs. THF, abs. benzene, abs. toluene and mixtures thereof ; and a Lewis base, such as abs. triethylamine, abs. pyridine, and mixtures thereof, in an amount at least equal to the stoichiometric amount of the activated ether. A highly preferred anhydrous, inert solvent is an acetonitrile containing abs. triethylamine in an amount at least equal to the stoichiometric amount of the activated ether.

Thus, the activated ether is reacted with the cyclic iminoether in the anhydrous, inert solvent to complete the ring-opening polymerization reaction.

This reaction may be carried out at room temperature or elevated temperature, and at around atmospheric pressure.

After the ring-opening polymerization reaction is completed, the obtained material is preferably, but not necessarily, treated with an alkali or alkali salt to stop the reaction and to obtain the polyamide ether. Alkali and alkali salts useful herein include sodium carbonate, sodium bicarbonate, potassium carbonate,

potassium bicarbonate, an amine in an anhydrous, inert solvent, and/or a metal or tetra-alkyl ammonium salts of an organic acid. When the obtained material is treated with aqueous an alkaline solution such as aqueous sodium carbonate, the resulting polyamide ether will contain a hydroxyl terminus. When the obtained material is treated with an amine in an anhydrous, inert solvent, the resulting polyamide ether will have amine terminus or ammonium terminus. When the obtained material is treated with a salt of an organic acid, the obtained polyamide ether will have a carboxylate terminus or an ester terminus.

Reduction or Hydrolysis Either a reducing agent and/or a hydrolyzing agent is optionally provided to react with the polyamide ether to form a polyamine ether. While reducing agents are known in the art, a preferred reducing agent includes LiAI (OR) xH4 wherein R is methyl, ethyl, or isopropyl, and x is an integer from 0 to 3; preferably LiAIH4 (lithium aluminum hydride) in the presence of an anhydrous, inert solvents such as abs. THF and abs. diethylether. Reduction may also be accomplished by reacting the polyamide ether with an agent such as (C2H5) 3O+BF4-, Cl3SiH, Cl3SiOH, Cl3SiOCH3, CI3SiOC2H5, (CH3) 3SiCI or dimethylsulfate in an inert solvent such as n-hexane or CH2CI2, followed by treatment with NaB (CN) H3 or NaBH4 in diethylether, ethanol, or THF.

Alternatively in place of a reducing agent, a hydrolyzing agent may be provided with which to hydrolyze the polyamide ether. A preferred hydrolyzing agent useful herein is an aqueous or an aqueous-alcohol solution of a strong acid or an alkali such as HCI, NaOH, KOH, or NaHCO3. Hydrolysis may be accomplished, for example, by reacting the polyamide ether with the hydrolyzing agent to obtain a polyamine ether.

Alternatively the polyamide ether may be both reduced and hydrolyzed by reducing the polyamide ether with a reducing agent such as (C2H5) 3O+BF4-, Cl3SiH, Cl3SiOH, Cl3SiOCH3, CI3SiOC2H5, (CH3) 3SiCl and/or dimethylsulfate in an inert solvent such as n-hexane or CH2CI2, followed by treatment with a hydrolyzing agent such as a diluted aqueous solution of an acid or an alkali such as HCI, NaOH, KOH, NaHCO3, K2CO3, Na2CO3, KHCO3, and/or an aqueous solution of an inorganic salt such as NaCI, KCI, and/or NH4CI.

In this step, the polyamide ether is preferably a polyamide polyether and the polyamine ether is preferably a polyamine polyether.

Quaternization The polyamine ether, preferably the polyamine polyether, is then typically quaternized to obtain the polymer of the present invention. The quaternizing agent useful herein is selected from the group consisting of monomethylsulfuric acid, dimethylsulfate, diethylsulfate, dimethylcarbonate, alkyl halides such as methylchloride, methyliodide, methylbromide, ethylchloride, ethyliodide, ethylbromide, benzylchloride, benzylbromide, benzyliodide ; sulfuric acid, carboxylic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and a mixture thereof. It is known in the art that, when quaternization is conducted with quaternizing agents which provide positively-charged alkyls such as monomethylsulfuric acid, dimethylsulfate, diethylsulfate, dimethylcarbonate, methylchloride, methyliodide, methylbromide, ethylchloride, ethyliodide, ethylbromide, benzylchloride, benzylbromide, benzyliodide, and other alkyl halides, the quaternized site is stable and pH-independent. On the other hand, when quaternization is conducted with quaternization agents which provide protons to the amine moiety such as sulfuric acid, carboxylic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and mixtures thereof, the quaternized site is pH-dependent. The quaternizing agent may be selected according to the desired characteristic of the polymer having a plurality of cationic moieties.

Alternatively, the polymer herein may also be prepared by a simplified two- step procedure reacting the activated ether described above directly with a polyamine via nucleophilic substitution, followed by quaternization with a quaternizing agent. Thus, the activated ether described above may also be employed in nucleophilic substitution reactions with polyamines. In these circumstances, the nucleophilic sites are those nitrogen centers of the polyamines which displace the leaving groups of the preferred and previously described halide, tosyl ester, and/or mesyl ester derivatives of the activated ether.

The polyamine useful herein may have repeating C2 C6 alkoxy units, either as straight-chain or branched, cyclic or aromatic moieties. The degree of polymerization for a linear polyamine (to form the linear polymer) may range from

about 2 to about 40, while the degree of polymerization of a branched polyamine (to form the branched polymer) may range from about 4 to about 80. The polyamine may be either linear or branched. As this is a substitution reaction, a preferred leaving group includes a tosyl group and a mesyl group. Thus, the activated ether is used as a macromolecular initiator for the synthesis of a block copolymer through a nucleophilic reaction toward the tosylat ester group, the mesylate ester group, or the halide group at any amine site of the polyamine.

Thus, the resultant polyamine ether (sometimes described as a polyamine ether block copolymer) may be linear or branched, as desired.

The quaternization will typically take place in a polar solvent, preferably in an alcohol, or an alcohol solution, and more preferably in ethanol or an ethanol solution. The quaternization reaction may be carried out at around atmospheric pressure, and at either room temperature or elevated temperature. Once synthesized, the polymer herein may be identified by methods known in the art, such as nuclear magnetic resonance (hereinafter,"NMR").

Examples of the invention are set forth hereinafter by way of illustration and are not intended to be in any way limiting of the invention.

EXAMPLE 1 A polyethylene oxide-block-poly (N, N'-dilauryl ethyleneimine) polymer according to the present invention is prepared according to the following process.

Preparation of Mesyl Polyethylene Oxide In a 1000 mL flask, mesyl chloride (17.2 g; 0.15 mol) is added via an addition funnel to a stirred (magnetic) solution of polyethylene oxide-600 (30g; 0.05 mol) in 150 mL dried THF and triethylamine (15.2g; 0.15 mol) while cooling with ice water. The reaction mixture is stirred while cooling in an ice bath for 2 hours, and then at room temperature for 24 hours. Then mixture is filtered and the precipitate is washed with abs. THF. To this solution, 100 mL NaHCO3 (saturated solution) is added and stirred at room temperature for 2 hours.

The solution is extracted 3 times with 100 mL chloroform. The chloroform phases are combined and dried over Na2SO4 for 24 hours. After removal of the dry agent, chloroform solvent is removed at 35 C in vacuo. The remaining residue is heated at 60 °C in high vacuum for 2 hours. From this, 37 g of mesyl polyethylene oxide, as a yellow, viscous oil, is obtained.

Ring-Opening Polymerization In a 200 mL tube with a magnetic stirrer, the mesyl polyethylene oxide formed above (30.3 g; 0.04 mol), 2-methyl-2-oxazoline (68 g; 0.8 mol), triethylamine (8.1 g; 0.08 mol) and acetonitrile (60 mL) are added in the presence of a N2 atmosphere. The tube was sealed and the mixture stirred under 80 °C for 24 hours. The mixture is then cooled to room temperature and then poured into 20 mi aqueous Na2CO3 (10% wt), and stirred for 2 hours.

After filtration, the mixture is placed under vacuum to remove the acetonitrile and water. The product is purified by dissolving it in chloroform and precipitating it in isopropanol. From this procedure, 83 g (90%) of poly (ethylene oxide)-block-poly (N-acyl ethylene imine) is recovered.

Hydrolysis and Preparation of Polyethylene Oxide-Block-Polyethylene Imine In a 1000 mL flask with a condenser, the poly (ethylene oxide)-block- poly (N-acyl ethylene imine) (69 g; 0.6 mol acyl ethylene imine moieties) is dissolved in 180 mL water. An aqueous solution of NaOH (36 g; 0.9 mol) in water 180 mL is added while stirring. The mixture is stirred at 100 °C for 24 hours. After cooling to room temperature, the insoluble product was isolated by filtration, and extracted with 100% methanol. After the evaporation of methanol, 43.8 g of a white product was obtained, which is as identified as polyethylene oxide-block-polyethylene imine (structure: HO-(C2H4NH) 5-(C2H4O) 12-C2H4- (NHC2H4) 5-OH), giving a yield of 100%.

Quaternization and Preparation of Polyethvlene Oxide-Block-Poly (Dilauril Ethylene imine) Into a 200 mL three-necked-flask, add polyethylene oxide-polyethylene imine (5.3 g, 0.048 mol amine units), ethanol (50 mL), sodium carbonate (5.0 g, 0.047 mol) and lauryl bromide (25.0 g, 0.1 mol). The lauryl bromide is added in 20 times molar excess to drive the reaction, and to promote the formation of the dilauryl species. Mix with a magnetic stirrer and heat to 85 °C for 72 hours. Add dimethyl sulfate (12.1 g, 0.096 mol) into the mixture and stir for 24 hours, to further drive the reaction to completion. After removing the solvent by distilling it away, the product is washed by water and then by hexane to remove all the low molecular weight impurities and excess reactants. The product is then dried in vacuum at 60 °C for 12 hours.

This product is determined by NMR to be a polyethylene oxide-block-poly (N, N'-dilauryl ethyleneimine) polymer, corresponding to the formula:

where each R, = ethyl, R2= lauryl, R3 = lauryl, a = 5, b = 5, and c = 12.

EXAMPLE 2 A polyethylene oxide-block-poly (N-lauryl, N'-methyl ethyleneimine) polymer according to the present invention is prepared according to the process of Example 1, except that at the quaternization stage is replaced by the following. into a 200 mL three-necked-flask, add polyethylene oxide-polyethylene imine (10 g, 0.097 mol amine units), ethanol (80 mL), sodium carbonate (12.8 g, 0.12 mol) and lauryl bromide (24.2 g, 0.097 mol). Mix with a magnetic stirrer and heat to 85 °C for 72 hours. Then add dimethyl sulfate (18.3 g, 0.145 mol) dropwise into the mixture and stir for 24 hours. After distilling away the solvent, the product is washed by water and then by hexane to remove all the low molecular impurities.

The product is then dried in vacuum at 60 °C for 12 hours to obtain 19.6 g product.

This product is determined by NMR to be a polyethylene oxide-block-poly (N-lauryl, N'-methyl ethylene imine) polymer, corresponding to the following formula : where each R, = ethyl, R2 = lauryl, R3 = methyl, a = 5, b = 5, and c = 12.

EXAMPLE 3 The following linear polymer of Example 2 is synthesized according to the process herein. This polymer has the structure:

The anti-microbial effects of this linear polymer is tested. It is believed that its many hydrophobic groups provide it with good deposition on negatively- charged fabric surfaces.

The"Minimum Inhibitory Concentration" (MIC) is determined according to a standard test, for the above linear polymer. The linear polymer was diluted employing serial 1: 1 dilutions, and then directly applied to the substrate, at the given concentration (in ppm) to determine the MIC. E. S. S. S. P. E. P. C. Z. coli aureus epider sanguis acnes gergovi granul albican bailii midis ae osum s Polymer 23. 43 7.81 3.90 5.85 0. 97 125 15. 62 46. 87 23.43 As can be seen, the polymer has a significant anti-microbial efficacy across a wide range of microorganisms.

EXAMPLE 4 Two polymers of the present invention (A and B) are tested for anti- microbial efficacy against the following microorganisms to determine the MIC and the"Minimum Biocidal Concentration" (MBC). Polym Type E. S. S. S. P. E. P. C. Z. er of Test coli aureus epider sangui acnes gergov granul albica bailii midis s iae osum ns Microb G (-) G (+) G (+) G (+) G (+) G (-) G (+) yeast fungus etype A* MIC 62.5 31.5 7.8 31.5 3.9 125 7.8 31.5 62.5 A* MBC 1000 31. 5 15.6 ND ND 250 ND 62.5 ND B** MIC 500 31.5 15.62 31. 5 3.9 2000 31.5 31.25 62.5 B** MBC >2000 31.5 15.6 ND ND ND ND 62.5 ND Ct MIC >2000 >2000 62.5 500 <1.9 >2000 500 125 125 Dt MIC >2000 >2000 250 500 7. 81 >2000 250 500 125 All measurements are provided in ppm.

* The polymer of Example 2 ** The polymer of Example 1

Comparative polymer having the structure HO- (C2H4N+ (CH3)2)10 - (C2H4O) 12- C2H4-(N+ (cH3) 2c2H4ho-oH t Comparative polymer having the structure HO- (C2H4N+ (CH3) 2) 5 (C2H4O) 12- C2H4-(N (CH3) 2C2H4) 5-oH As can be seen from the above side-by-side comparison, the polymers A and B are significantly more effective against a wide variety of microbes, than the comparative polymers C and D. While the data of this table that of the table in Example 3 show slight differences, the values are within an acceptable error range (i. e., about a 4-fold difference). Furthermore, the compound of Example 2 (polymer A) still shows significant benefits over the comparative polymers C and D, especially over a broad range of microorganisms.

EXAMPLE 5 A hair conditioning composition is prepared according to the following formulas (all levels are percentages, by weight of the final composition) : Component Ex. A Ex. B Ex. C Ex. D Polymer of Example 2 3 2 0. 5 Cetyl alcohol 3 4. 3 6 Stearyl alcohol 2 2. 8 4 1 Methyl paraben--0. 2 0.2 Propyl paraben 0. 10.1 Ethylene diamine tetraacetic0.1 0. 1-0.1 acid(EDTA) DisodiumEDTA--0. 13- Water, perfume, minors balance balance balance balance EXAMPLE 6 An antimicrobial fabric conditioning composition is prepared according to the following formula (all levels are percentages, by weight of the final composition): Component Example A Triethanol amine ester methyl 28% ammoniummethylsulfate Polymer of Example 1 3% 2-ethyl 1,3 hexane diol 8% Cocoamide 1. 65% Caca20. 1 % Sodium 1,1-hydroxyethane 0.02% diphosphonate Perfume 0. 4% Benzyl Benzoate 1. 5% Water,dye, minors balance

EXAMPLE 7 An antimicrobial hard surface cleaning composition, especially for cleaning toilets, is prepared according to the following formulas (all levels are percentages, by weight of the final composition):

Component Example A Example B Example C Potassiummonopersulfate salt 4 4 6 Polymer of Example 2 0. 1 1 3 Myristyl trimethyl sulfate 1. 8 2. 2 2. 5 Eucalyptol 0. 3 0. 5 0. 3 pH 0. 5 0. 5 0. 7 Water,minors balance balance balance