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Title:
OIL-FREE OXIDATIVELY CURABLE POLYESTER COMPOSITIONS
Document Type and Number:
WIPO Patent Application WO/2000/066646
Kind Code:
A2
Abstract:
The invention relates to oil-free polyesters and carboxyl functional aligomeric adducts modified with 3,4-epoxy-1-butene to yield resins with allyl groups. These allyl functional resins were found to be oxidatively curable in the presence of metal catalysts such as cobalt and zirconium coupounds. As a result, the 3,4-epoxy-1-butene modified polyesters and oligomeric adducts of the present invention have utility as binders for ambient-cured coating applications.

Inventors:
KUO THAUMING (US)
POWELL JEFFREY E G (US)
Application Number:
PCT/US2000/012044
Publication Date:
November 09, 2000
Filing Date:
May 04, 2000
Export Citation:
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Assignee:
EASTMAN CHEM CO (US)
KUO THAUMING (US)
POWELL JEFFREY E G (US)
International Classes:
C08G63/58; C08G63/91; C09D167/07; (IPC1-7): C08G63/00
Foreign References:
EP0859021A21998-08-19
US3716508A1973-02-13
EP0217660A21987-04-08
Attorney, Agent or Firm:
MORGAN, LEWIS & BOCKIUS LLP (NW Washington, DC, US)
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Claims:
CLAIMS The Claimed invention is:
1. An oxidatively curable modified polyester comprising the reaction product of : (a) an oilfree polyester with an acid number of about 25200 mg KOH/g ; and (b) 3,4epoxy1butene, wherein the number of allyl groups in the oxidatively curable polyester is sufficient to enable it to cure oxidatively.
2. The oxidatively curable polyester of claim 1, wherein the oilfree polyester is formed by reacting the following compounds: (i) about 3070 mole % of a diol; (ii) about 020 mole % of a polyol; (iii) about 2060 mole % of a diacid; and (iv) about 020 mole % of a dicarboxylic acid anhydride, wherein the mole percents are based on the total moles of (i), (ii), (iii), and (iv).
3. The oxidatively curable polyester of claim 1, wherein the molar ratio of 3,4 epoxy1butene (b) to carboxyl groups in the oilfree polyester (a) is about 0.520.
4. The oxidatively curable polyester composition of claim 3, wherein the equivalent ratio of 3, 4epoxy1butene (b) to carboxyl groups in the oilfree polyester (a) is about 1 10 and wherein the diol is present in an amount of about 4060 mole %, the polyol is present in an amount of about 210 mole %, the diacid is present in an amount of about 3050 mole % and the dicarboxylic acid anhydride is present in an amount of about 315 mole %.
5. The oxidatively curable polyester composition of claim 4, wherein the equivalent ratio of 3, 4epoxy1butene (b) to carboxyl groups in the oilfree polyester (a) is about 1 5 and wherein the diol is present in an amount of about 4555 mole %, the polyol is present in an amount of about 35 mole %, the diacid is present in an amount of about 35 45 mole % and the dicarboxylic acid anhydride is present in an amount of about 410 mole %.
6. An oxidatively curable coating formulation comprising: (a) an oxidatively curable modified polyester according to claim 1; (b) an organic solvent; and (c) a catalytic amount of metal drier.
7. The oxidatively curable coating formulation of claim 6, wherein the oxidatively curable modified polyester (a) is present in an amount of about 5095 weight % and the organic solvent (b) is present in an amount of about 550 weight %, wherein the weight percents are based on the total weight of (a) and (b).
8. The oxidatively curable coating formulation of claim 7, wherein the metal drier is a metal carboxylate.
9. The oxidatively curable coating formulation of claim 8, wherein the metal is selected from the group consisting of cobalt, zirconium, calcium, manganese, a rare earth metal, aluminum, zinc, iron and mixtures thereof.
10. The oxidatively curable coating formulation of claim 9, wherein the oxidatively curable modified polyester (a) is present in an amount of from about 7080 weight % and the organic solvent (b) is present in an amount of about 2030 weight %, wherein the weight percents are based on the total weight of (a) and (b).
11. An oxidatively curable oligomeric adduct comprising the reaction products of : (a) a polyol; (b) a dicarboxylic acid anhydride (c) 3,4epoxy1butene, wherein the number of moles of dicarboxylic acid anhydride (b) is greater than or equal to the number of moles of the polyol (a) and wherein the number of allyl groups in the oxidatively curable oligomeric adduct is sufficient to enable it to cure oxidatively.
12. The oxidatively curable oligomeric adduct of claim 11, wherein the molar ratio of 3,4epoxy1butene (c) to dicarboxylic acid anhydride (b) is about 0.520.
13. The oxidatively curable oligomeric adduct according to claim 12, wherein the molar ratio of 3,4epoxy1butene (c) to dicarboxylic acid anhydride (b) is about 110.
14. An oxidatively curable oligomeric adduct according to claim 13, wherein the molar ratio of 3,4epoxy1butene (c) to dicarboxylic acid anhydride (b) is about 15.
15. An oxidatively curable coating formulation comprising: (a) the oxidatively curable oligomeric adduct of claim 11; (b) an organic solvent; and (c) a catalytic amount of a metal drier.
16. The oxidatively curable coating formulation of claim 15, wherein the oxidatively curable oligomeric adduct (a) is present in an amount of about 5095 weight % and the organic solvent (b) is present in an amount of about 550 weight %, wherein the weight percents are based on the total weight of (a) and (b).
17. The oxidatively curable coating formulation of claim 16, wherein the oxidatively curable oligomeric adduct (a) is present in an amount of about 6090 weight % and the organic solvent (b) is present in an amount of about 1040 weight %, wherein the weight percents are based on the total weight of (a) and (b).
18. The oxidatively curable coating formulation of claim 17, wherein the oxidatively curable oligomeric adduct (a) is present in an amount of about 7080 weight % and the organic solvent (b) is present in an amount of about 2030 weight %, wherein the weight percents are based on the total weight of (a) and (b).
19. An oxidatively cured film of the coating composition of claim 6.
20. An oxidatively cured film of the coating composition of claim 15.
Description:
INTERNATIONAL SEARCH REPORT mternatj ppilcatlon tao if nation on patent family members PCT/ub 00/12044 Patent document Publication Patent family Publication cited in search report date member (s) date EP 0859021 A 19-08-1998 JP 5117314 A 14-05-1993 JP 5140270 A 08-06-1993 JP 6001934 A 11-01-1994 JP 6001829 A 11-01-1994 JP 6033012 A 08-02-1994 JP 6032868 A 08-02-1994 JP 6080764 A 22-03-1994 JP 6080922 A 22-03-1994 JP 6095380 A 08-04-1994 JP 6100800 A 12-04-1994 JP 6116348 A 26-04-1994 DE 69229383 D 15-07-1999 EP 0540027 A 05-05-1993 US 5510428 A 23-04-1996 US 5494977 A 27-02-1996 JP 6041275 A 15-02-1994 JP 6049115 A 22-02-1994 US 3716508 A 13-02-1973 NONE EP 0217660 A 08-04-1987 US 4644038 A 17-02-1987 CA 1244187 A 01-11-1988 JP 2014390 C 02-02-1996 JP 7030171 B 05-04-1995 JP 62104836 A 15-05-1987