US2019284335A1PendingUtilityA1

Urethane-compatible polyester adhesion promoters

Assignee: SUN CHEMICAL CORPPriority: Jan 22, 2014Filed: May 31, 2019Published: Sep 19, 2019
Est. expiryJan 22, 2034(~7.5 yrs left)· nominal 20-yr term from priority
C08G 63/52C08G 63/78C08G 63/54C08G 18/4241C08G 63/199C08G 18/4263C09D 11/104
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Claims

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.

Claims

exact text as granted — not AI-modified
1 . A polyester resin according to General Formula I:
   HO—[R 1 R 2 C(CH 2 —) 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 about 10,000;   the Tg is less than about 5° C.;   the hydroxyl value is about 225-300; and   wherein the polyester resin is formed by the reaction of dibasic organic acids, one or more organic compounds with multiple functional groups, and one or more polyols;   wherein 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, and wherein the polyester resin is hydroxyl-functional, with no carboxyl-functionality.   
     
     
         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 about 10,000;   the Tg is less than about 5° C.;   the hydroxyl value is about 225-290;   the acid value is about 75-100; and   wherein the polyester resin is formed by the reaction of dibasic organic acids, one or more organic compounds with multiple functional groups, and one or more polyols; and wherein the polyester resin is hydroxyl-functional and carboxyl-functional.   
     
     
         3 . The polyester resin of  claim 1 , wherein at least one of R 1  and R 2  is methyl. 
     
     
         4 . The polyester resin of  claim 1 , wherein at least one of R 1  and R 2  is —CH 2 OH. 
     
     
         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. 
     
     
         7 . The polyester resin of  claim 2 , wherein at least one of R 1 , R 2 , and R 3  is —CH 2 OH. 
     
     
         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. 
     
     
         10 . The polyester resin of  claim 1 , wherein y is 2-10. 
     
     
         11 . (canceled) 
     
     
         12 . The polyester resin of  claim 1 , wherein p is 4. 
     
     
         13 . The polyester resin of  claim 1 , wherein z is 8. 
     
     
         14 . (canceled) 
     
     
         15 . The polyester resin of  claim 1 , wherein the ratio a:c is between about 1:2 and about 1:4. 
     
     
         16 . (canceled) 
     
     
         17 . (canceled) 
     
     
         18 . (canceled) 
     
     
         19 . The polyester resin of  claim 2 , wherein the ratio a:d is between about 1:2 and about 1:4. 
     
     
         20 . (canceled) 
     
     
         21 . (canceled) 
     
     
         22 . (canceled) 
     
     
         23 . The polyester resin of  claim 1 , wherein the dibasic organic acids are selected from the group consisting of a phthalic acid and a maleic acid. 
     
     
         24 . (canceled) 
     
     
         25 . The polyester resin of  claim 1 , wherein the polyols are glycols. 
     
     
         26 . (canceled) 
     
     
         27 . (canceled) 
     
     
         28 . (canceled) 
     
     
         29 . (canceled) 
     
     
         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 about 0.1 to about 10%. 
     
     
         34 . (canceled) 
     
     
         35 . The printing ink or coating composition of  claim 32 , wherein the polyester resin is present in an amount of from about 10.1 to about 35%. 
     
     
         36 . The printing ink or coating composition of  claim 32 , wherein the ink or coating composition comprises a polyurethane. 
     
     
         37 . (canceled) 
     
     
         38 . (canceled) 
     
     
         39 . The printing ink or coating composition of  claim 32 , further comprising a colorant. 
     
     
         40 . (canceled) 
     
     
         41 . The polyester resin of  claim 2 , wherein x is 6. 
     
     
         42 . The polyester resin of  claim 2 , wherein y is 2-10. 
     
     
         43 . The polyester resin of  claim 2 , wherein the dibasic organic acids are selected from the group consisting of a phthalic acid and a maleic acid. 
     
     
         44 . The polyester resin of  claim 2 , wherein the polyols are glycols. 
     
     
         45 . A printing ink or coating composition comprising the polyester resin of  claim 2 . 
     
     
         46 . The printing ink or coating composition of  claim 45 , wherein the polyester resin is present in an amount of from about 0.1 to about 10%. 
     
     
         47 . The printing ink or coating composition of  claim 45 , wherein the polyester resin is present in an amount of from about 10.1 to about 35%. 
     
     
         48 . The printing ink or coating composition of  claim 45 , wherein the ink or coating composition comprises a polyurethane. 
     
     
         49 . The printing ink or coating composition of  claim 45 , further comprising a colorant.

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