Urethane-compatible polyester adhesion promoters

Patent metadata

Field	Value
Publication number	US-2016333142-A1
Application number	US-201515112535-A
Country	US
Kind code	A1
Filing date	Jan 21, 2015
Priority date	Jan 22, 2014
Publication date	Nov 17, 2016
Grant date	—

Abstract

The present invention concerns polyester resins of General Formula I (HO—[R 1 R 2 C(CH 2 —)] a [—OCOC x H y CO 2 —] b [—C p H z O—] c —H) or General Formula II (HO—[R 1 R 2 C(CH 2 —) 2 ] a [—OCOC x H y CO 2 —] b [—CH 2 CR 3 (CO 2 H)CH 2 O] d —H), wherein R 1 , R 2 , a, b, c, d, x, y, p, and z are as defined herein, for use in inks and coating compositions. The polyester resins of the present invention are particularly, but not exclusively, suitable to enhance the adhesion between a printing ink or coating composition and a substrate, especially a plastic substrate, to which it is applied. The polyester adhesion promoters of the invention are compatible with urethane-based inks and coating compositions.

First claim

1 . A polyester resin according to General Formula I:
HO—[R 1 R 2 C(CH 2 —)] a [—OCOC x H y CO 2 —] b [—C p H z O—] c —H
wherein: R 1 and R 2 are each independently selected from the group consisting of H, C 1 -C 4 alkyl, and —CH 2 OH; x is an integer 1 through 10; y is an integer 2 through 20; p is an integer 2 through 8; z is two times p; each C x H y and C p H z are each independently linear or branched alkyl, optionally comprising an aromatic, or saturated or unsaturated alicyclic ring; a, b, and c are each independently an integer 1 through 100; provided that b<a+c; the M W is less than 10,000; the Tg is less than 5° C.; the hydroxyl value is 225-300; and wherein the polyester resin is formed by the reaction of one or more unsaturated condensation polymers produced by a reaction of dibasic organic acids, one or more organic compounds with multiple functional groups, and one or more polyols.

2 . A polyester resin of the General Formula II:
HO—[R 1 R 2 C(CH 2 —) 2 ] a [—OCOC x H y CO 2 —] b [—CH 2 CR 3 (CO 2 H)CH 2 O] d —H
wherein: R 1 , R 2 , and R 3 are each independently selected from the group consisting of H, C 1 -C 4 alkyl, and —CH 2 OH; x is an integer 1 through 10; y is an integer 2 through 20; each C x H y is independently linear or branched alkyl, optionally comprising an aromatic, or saturated or unsaturated alicyclic ring; a, b, and d are each independently an integer 1 through 100; provided that b>a+d; the M W is less than 10,000; the Tg is less than 5° C.; the hydroxyl value is 225-290; the acid value is 75-100; and wherein the polyester resin is formed by the reaction of one or more unsaturated condensation polymers produced by a reaction of dibasic organic acids, one or more organic compounds with multiple functional groups, and one or more polyols.

3 . The polyester resin of claim 1 , wherein at least one of R 1 and R 2 is methyl or —CH 2 OH.

4 . (canceled)

5 . The polyester resin of claim 1 , wherein one of R 1 and R 2 is methyl, and the other is —CH 2 OH.

6 . The polyester resin of claim 2 , wherein at least one of R 1 , R 2 , and R 3 is methyl or —CH 2 OH.

7 . (canceled)

8 . The polyester resin of claim 2 , wherein at least one of R 1 , R 2 , and R 3 is methyl, and at least one of R 1 , R 2 , and R 3 is —CH 2 OH.

9 . The polyester resin of claim 1 , wherein x is 6, v is 2-10, p is 4 and z is 8.

10 . (canceled)

11 . The polyester resin of claim 1 , wherein y is 8 or 10.

12 . (canceled)

13 . (canceled)

14 . The polyester resin of claim 1 , wherein the hydroxyl value is 290 or 250.

15 . The polyester resin of claim 1 , wherein the ratio a:c is between 1:2 and about 1:4.

16 . The polyester resin of claim 1 , wherein the ratio a:c is 3:7.

17 . (canceled)

18 . The polyester resin of claim 2 , wherein the acid value is about 85.

19 . The polyester resin of claim 2 , wherein the ratio a:d is between 1:2 and 1:4.

20 . The polyester resin of claim 2 , wherein the ratio a:d is 3:7.

21 . The polyester resin of claim 1 , wherein the ratio of the total concentration of hydroxyl moieties in the combined starting materials to the total concentration of the carboxylic acid moieties is between 1.5:1 and 2.0:1.

22 . (canceled)

23 . The polyester resin of claim 1 , wherein the dibasic organic acids are selected from the group consisting of a phthalic acid, a maleic acid and tetrahydrophthalic acid.

24 . (canceled)

25 . The polyester resin of claim 1 , wherein the polyols are glycols.

26 . The polyester resin of claim 1 , wherein the M W is less than 8,000, less than 5,000 or less than 1,000.

27 . (canceled)

28 . (canceled)

29 . The polyester resin of claim 1 , wherein the Tg is less than 3° C., is less than 1° C. or less than 0° C.

30 . (canceled)

31 . (canceled)

32 . A printing ink or coating composition comprising the polyester resin of claim 1 .

33 . The printing ink or coating composition of claim 32 , wherein the polyester resin is present in an amount of from 0.1 to 10% or from 0.1 to 5%.

34 . (canceled)

35 . The printing ink or coating composition of claim 32 , wherein the polyester resin is present in an amount of from 10.1 to 35%.

36 . The printing ink or coating composition of claim 32 , wherein the ink or coating composition comprises a polyurethane or a polyurethane in combination with other polymeric binders.

37 . (canceled)

38 . The printing ink or coating composition of claim 36 , wherein the polyurethane is the predominant resin.

39 . The printing ink or coating composition of claim 32 , further comprising a colorant.

40 . A method of making a polyester resin of claim 1 , comprising reacting one or more unsaturated condensation polymers produced by a reaction of dibasic organic acids, one or more organic compounds with multiple functional groups, and one or more polyols.

Assignees

• Sun Chemical Corp

Inventors

• Arcurio Ralph
• Chudolij Alex
• Krishnan Ramasamy
• Schneider Mark
• Hunt Paul
• Smales Paul

Classifications

• C08G63/54

  the acids or hydroxy compounds containing carbocyclic rings · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08G63/52

  Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08G63/199 Primary

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title

• C09D11/104 Primary

  Polyesters · CPC title