Patent EA-001544-B1 (EA)
Title: Water dispersible/redispersible hydrophobic polyester resins and their application in coatings
Inventor: SALSMAN ROBERT KEITH
IPC: C08G63/20
Filed: 1998-01-27
Abstract: 1. A water dispersible and hydrophobic polyester resin having the formula: In-P-Am wherein I is an ionic group; n=1-3 is the number of ionic groups; P is a polyester backbone; A is a fatty aliphatic group; m=3-8 is the number of fatty aliphatic groups and wherein I is present in amount of from about 1 % to 20% by weight; the polyester backbone is present in an amount of from about 30% to 80% by weight and the fatty aliphatic group is present in an amount of about 10% to 60% by weight; said polyester resins exhibiting high water repellency as shown by an initial contact angle of at least 98 when a drop of water is applied to the surface of a cellulosic substrate which has been coated with said resin. 2. The water dispersible and hydrophobic polyester resin of claim 1 wherein I is present in an amount ranging from 5 % to 10% by weight. 3. The water dispersible and hydrophobic polyester resin of claim 1 wherein the polyester backbone P is present in an amount ranging from 50% to 60% by weight. 4. The water dispersible and hydrophobic polyester resin of claim 1 wherein the fatty acid group A is present in an amount ranging from 20% to 40% by weight. 5. The water dispersible and hydrophobic polyester resin of claim 1 wherein I is derived from polycarboxylic acid or anhydrides selected from the group consisting of trimellitic anhydride, trimellitic acid and malefic anhydride. 6. The water dispersible and hydrophobic polyester resin of claim 1 wherein the polyester backbone P is a polyalkyleneterephthalate selected from the group consisting of polyethyleneterephthalate, polypropyleneterephthalate and polybutyleneterephthalate. 7. The water dispersible and hydrophobic polyester resin of claim 1 wherein the fatty acid group A is selected from the group consisting of stearic acid, behenic acid, palmitic acid, lauric acid, oleic acid and linoleic acid. 8. A water dispersible and hydrophobic polyester resin, comprising a reaction product of 30-70% by weight of a terephthalate polymer; 5-40% by weight of a hydroxy functional compound having at least two hydroxyl groups; 1-20% by weight of a carboxy functional compound having at least two carboxyl groups and 10-60% by weight of a hydrophobic compound selected from the group consisting of C6-C24 straight chain or branched fatty acid or triglycerides thereof; said resin being further characterized in that the hydroxy functional compound is present at 1-3 times the equivalents of the hydrophobic moiety. 9. The water dispersible and hydrophobic polyester resin of claim 8, comprising the reaction product of waste terephthalate of the unit formula   wherein R is the residue of an aliphatic or cycloaliphatic glycol of 2-10 carbon atoms of or oxygenated glycol of the formula HO (CxH2xO)nCxH2xOH                       (2) wherein x is an integer from 2-4 and n is 1-10. 10. The water dispersible and hydrophobic polyester resin of claim 8, wherein the waste terephthalate polymer is polyethyleneterephthalate, poly-1,2-propyleneterephthalate, poly-l,3-propyleneterephthalate, polybutylene-terephthalate, poly(cyclohexanedimethanolterephthalate) or a mixture thereof. 11. The water dispersible and hydrophobic polyester resin of claim 8, wherein said hydroxy functional compound having at least two hydroxyl groups is selected from the group consisting of ethyleneglycol, diethyleneglycol, triethyleneglycol, cyclohexanedimethanol, propyleneglycol, 1,2-propyleneglycol, 1,3-propanediol, 1,2-butyleneglycol, 1,3-butanediol, 1,4-butanediol, neopentylglycol, 1,5-pentanediol, 1,6-hexanediol, glycerin, trimethylolpropane, trimethylolethane, pentaerythrite, erythrite or a monosaccharide. 12. The water dispersible and hydrophobic polyester resin of claim 8, wherein said hydroxy functional compound having at least two hydroxyl groups is selected from the group consisting of derivatives of glycerine, trimethylolpropane, trimethylolethane, pentaerythrite, erythrite or a monosaccharide oxyalkylated with 5-30 moles of ethyleneoxide, propyleneoxide or a mixture thereof, per hydroxyl of the hydroxy functional compound. 13. The water dispersible and hydrophobic polyester resin of claim 8, wherein said carboxy functional compound having at least two carboxyl groups is selected from the group consisting of trimellitic acid, trimellitic anhydride, malefic acid, malefic anhydride, fumaric acid and isophthalic acid. 14. The water dispersible and hydrophobic polyester resin of claim 8, wherein said hydrophobic compound is selected from the group consisting of stearic acid, oleic acid, linoleic acid, behenic acid, lauric acid, palmitic acid, beef tallow, lard, corn oil and soybean oil. 15. The water dispersible and hydrophobic polyester resin of claim 8, comprising the reaction product of 40-60% by weight of polyethyleneterephthalate polymer; 1-10% by weight of neopentylglycol; 5-10% pentaerythrite; 3 to 15 % by weight of trimellitic acid or trimellitic anhydride; and 10-45 % by weight of stearic acid. 16. The water dispersible and hydrophobic polyester resin of claim 8, comprising a reaction product prepared in the presence of monobutylstannoic acid or a tetraalkyltitanate, or a mixture thereof. 17. The water dispersible and hydrophobic polyester resin of claim 8, dispersed in water with an alkali metal or ammonium hydroxide or carbonate. 18. The water dispersible and hydrophobic polyester resin of claim 15, dispersed in water with an alkali metal or ammonium hydroxide or carbonate. 19. An article of manufacture comprising a substrate coated with a water dispersible and hydrophobic polyester resin coating composition comprising a reaction product of 30-70% by weight of a terephthalate polymer; 5-40% by weight of a hydroxy functional compound having at least two hydroxyl groups; 1-20% by weight of a carboxy functional compound having at least two carboxyl groups and 10-60% by weight of a hydrophobic compound selected from the group consisting of C6-C24 straight chain or branched fatty acid or triglycerides thereof. 20. The article of manufacture of claim 19, wherein said substrate is a fibrous substrate. 21. The article of manufacture of claim 19, wherein said substrate is a paper substrate. 22. The article of manufacture of claim 19, wherein said substrate is a textile substrate. 23. The article of manufacture of claim 19, wherein said substrate is food packaging. 24. The article of manufacture of claim 19, wherein said substrate is separating paper. 25. The article of manufacture of claim 19, wherein said substrate is concrete. 26. The coated article of manufacture of claim 19, wherein said terephthalate polymer is a waste terephthalate of the unit formula   wherein R is the residue of an aliphatic or cycloaliphatic glycol of 2-10 carbon atoms or oxygenated glycol of the formula HO (CxH2xO)nCxH2xOH                       (2) wherein x is an integer from 2-4 and n is 1-10. 27. The coated article of manufacture of claim 26 wherein the waste terephthalate polymer is polyethyleneterephthalate, poly-l,2-propyleneterephthalate, poly-1,3-propyleneterephthalate, polybutyleneterephthalate, poly(cyclohexanedimethanolterephthalate) or a mixture thereof. 28. The coated article of manufacture of claim 19, wherein said hydroxy functional compound having at least two hydroxyl groups selected from the group consisting of ethyleneglycol, diethyleneglycol, triethyleneglycol, cyclohexanedimethanol, propyleneglycol, 1,2-propyleneglycol, 1,3-propanediol, 1,2-butyleneglycol, 1,3-butanediol, 1,4-butanediol, neopentylglycol, 1,5-pentanediol, 1,6-hexanediol, glycerine, trimethylolpropane, trimethylolethane, pentaerythrite, erythrite or a monosaccharide. 29. The coated article of manufacture of claim 19, wherein said hydroxy functional compound having at least two hydroxyl groups is selected from the group consisting of derivatives of glycerine, trimethylolpropane, trimethylolethane, pentaerythrite, erythrite or a monosaccharide oxyalkylated with 5-30 moles of ethyleneoxide, propyleneoxide or a mixture thereof, per hydroxyl group of the hydroxy functional compound. 30. The coated article of manufacture of claim 19, wherein said carboxy functional compound having at least two carboxyl groups is selected from the group consisting of trimellitic acid, trimellitic anhydride, maleic acid, maleic anhydride, fumaric acid and isophthalic acid. 31. The coated article of manufacture of claim 19, wherein said hydrophobic compound is selected from the group consisting of stearic acid, oleic acid, linoleic acid, behenic acid, lauric acid, palmitic acid, beef tallow, lard, corn oil and soybean oil. 32. An article of manufacture comprising a substrate coated with a water dispersible and hydrophobic polyester resin coating composition comprising a reaction product of 40-60% by weight of polyethylene terephthalate polymer; 1-10% by weight of neopentylglycol; 5-10% pentaerythrite; 3-15% by weight of trimellitic acid or trimellitic anhydride; and 10-45% by weight of stearic acid. 33. The article of manufacture of claim 32, wherein said substrate is a fibrous substrate. 34. The article of manufacture of claim 32, wherein said substrate is a paper substrate. 35. The article of manufacture of claim 32, wherein said substrate is a textile substrate. 36. The article of manufacture of claim 32, wherein said substrate is food packaging. 37. The article of manufacture of claim 32, wherein said substrate is separating paper. 38. The article of manufacture of claim 32, wherein said substrate is concrete. 39. A water repellent polyester coating composition, comprising a reaction product of 30-70% by weight of a terephthalate polymer; 5-40% by weight of a hydroxy functional compound having at least two hydroxyl groups; 1-20% by weight of a carboxy functional compound having at least two carboxyl groups and 10-60% by weight of a hydrophobic compound selected from the group consisting of C6-C24 straight chain or branched fatty acid or triglycerides thereof. 40. A water repell