Alkyd resins containing hydroxyl groups

Claim 2

A process for synthesizing alkyd resin compositions comprising: (A) condensing a carboxylic acid with an alcohol to form a polyester precondensate having terminal hydroxyl groups, wherein (1) said carboxylic acid is a fatty acid, a polycarboxylic acid, a reactive derivative thereof, or any mixture thereof, (2) said alcohol is at least one polyfunctional alcohol, and said condensation reaction is conducted at a temperature of about from 120° to 220° C. and is continued until the acid number of the precondensate is less than 2; (B) converting said precondensate into an acidic precondensate by further condensation with a polycarboxylic acid anhydride wherein (1) said polycarboxylic acid anhydride is a dicarboxylic acid anhydride, a tricarboxylic acid anhydride, a higher polycarboxylic acid anhydride, or any mixture thereof, and said further condensation is conducted at a temperature of about from 140° to 200° C. and continued until an acid number of about 50 to 130 is obtained; and (C) forming an alkyd resin by further esterification of said acidic precondensate with a further alcohol wherein (1) said further alcohol is at least one polyol having a functionality of from 3 to 10 or any mixture thereof, and said further esterification reaction is conducted at a temperature of about from 120° to 220° C. and is continued until an acid number of about 10 to 40 is obtained.

Claim 3

The process of claim 1 with an additional step comprising: (D) forming an alkyd resin emulsion by mixing said alkyd resin with an aminoalcohol present in an amount sufficient to neutralize said alkyd resin, and water.

Claim 4

The process of claim 2 wherein a hydroxylfunctional emulsifier is present is step (D)

Claim 5

The process of claim 1 wherein in step (A), (1) said carboxylic acid is at least one naturally occurring, or synthetic branched-chain, fatty acid having predominantly from 6 to 24 carbon atoms; at least one aliphatic or aromatic di- or tri-carboxylic acid or its anhydride; or any mixture thereof; and (2) said alcohol is dihydroxy and has about 2 to 30 carbon atoms, is trihydroxy and has about 3 to 30 carbon atoms, has 4 to 10 hydroxy groups and up to 75 carbon atoms, or is any mixture thereof.

Claim 6

The process of claim 1 wherein in step (A), said carboxylic acid is a mixture of naturally occurring fatty acids selected from one of (a) C 8-18 fractionated coconut oil fatty acids in which at least 40% by weight is lauric acid, at least 10% by weight is myristic acid, and at least 10% by weight is palmitic acid, (b) C 14-18 selectively hardened tallow fatty acids in which at least 35% by weight is oleic acid, at least 20% by weight is palmitic acid, and at least 20% by weight is stearic acid, or (c) predominantly C 8-12 fractionated fatty acids in which at least 55% by weight is caprylic acid and at least 30% by weight is capric acid, or said carboxylic acid is at least one polycarboxylic acid or its derivative selected from (d) glutaric acid, adipic acid, sebacic acid, homologs of the foregoing, phthalic acid or its isomers, trimellitic acid, cyclic anhydrides of the foregoing, or maleic acid anhydride.

Claim 7

The process of claim 1 wherein in step (A) said alcohol is: ethylene glycol, propylene glycol, neopentyl glycol, or the dimers, trimers, homologs of the foregoing containing up to 8 carbon atoms, or isomers of the foregoing; alcohols having a functionality higher than 3 which are glycerol, trimethlylol ethane, trimethylol propane, pentaerythritol, dipentaenythritol, sorbitol; or any mixture of the above.

Claim 8

The process of claim 1 wherein in step (B) said carboxylic acid anhydride is a cyclic anhydride having a functionality of more than 4.

Claim 9

The process of claim 1 wherein in step (B) said carboxylic acid anhydride is at least one of succinic acid anhydride, glutaric acid anhydride, maleic acid anhydride, phthalic acid anhydride, or trimellitic acid anhydride.

Claim 10

The process of claim 1 wherein in step (C) said further alcohol has up to 10 ether radicals and a number-average molecular weight of less than 1,000.

Claim 11

The process of claim 1 wherein in step (C) said further alcohol has a functionality of from 3 to 6, and a number-average molecular weight of less than 1,000.

Claim 12

The process of claim 1 wherein in step (C) said further alcohol is at least one of: glycerol; trimethylol ethane; trimethylol propane; pentaerythritol; the dimerization products of glycerol, trimethylol ethane or trimethylol propane; reaction products of any of the foregoing with up to 5 mols of ethylene oxide or propylene oxide; a polyol having 4 to 10 hydroxyl group selected from sorbitol, a polyglycerol with 2 to 4 ether oxygens, depentaerythritol, the reaction products of any of the foregoing polyols having 4 to 10 hydroxyl groups with up to 10 mols of ethylene oxide or propylene oxide; or any mixture thereof.

Claim 13

The process of claim 2 wherein in step (D) said aminoalcohol is: methylaminopropanol; methylaminopropane diol; tris-hydroxymethylaminomethane; reaction products of the foregoing with ethylene oxide; diethanolamine, triethanolamine; methyldiethanolamine; or any mixture thereof.

Claim 14

The process of claim 3 wherein in step (D) said emulsifier is at least one salt of an aminoalcohol with a hydroxyalkoxystearic acid containing at least one hydroxyl group in the alkoxy radical.

Claim 15

The process of claim 3 wherein in step (D) said emulisfier is at least one salt of an aminoalcohol with a 10,9- or 9,10-hydroxyalkoxystearic acid of which the alkoxy radical is derived from polyfunctional alcohols containing from 3 to 6 hydroxyl groups, and any mixtures of the above.

Claim 16

The process of claim 14 wherein in said emulsifier the alkoxy radical is derived from: glycerol, trimethylol propane, pentaerythritol, or sorbitol; the autocondensation products of the foregoing alcohols; the reaction products of the foregoing alcohols with up to 10 mols of ethylene oxide per mol of alcohol, or any mixtures of the above.

Claim 17

The process of claim 1 wherein: in step (A) said condensation reaction is conducted at a temperature of about from 140° to 200° C., and is continued until the acid number of the precondensate approaches 0; in step (B) said further condensation is continued until an acid number of about from 60 to 90 is obtained; and in step (C) said esterification is conducted at a temperature of about from 140° to 200° C., and is continued until an acid number of about 15 to 35 is obtained.

Claim 18

The process of claim 16 wherein: in step (C) said esterification is continued until an acid number of about 20 to 25 is obtained.

Claim 19

The process of claim 2 wherein said emulsion is about 5% to 25% by weight of water.

Claim 20

The process of claim 3 wherein said emulsion is about 15% by weight of water.

Claim 21

A process for synthesizing alkyd resin compositions comprising: (A) condensing a carboxylic acid with an alcohol to form a polyester precondensate having terminal hydroxyl groups wherein (1) said carboxylic acid is a mixture of naturally occurring fatty acids selected from one of (a) C 8-18 fractionated coconut oil fatty acids in which at least 40% by weight is lauric acid, at least 10% by weight is myristic acid, and at least 10% by weight is palmitic acid, (b) C 14-18 selectively hardened tallow fatty acids in which at least 35% by weight is oleic acid, at least 20% by weight is palmitic acid, and at least 20% by weight is stearic acid, or (c) predominantly C 8-12 fractionated fatty acids in which at least 55% by weight is caprylic acid and at least 30% by weight is capric acid, or said carboxylic acid is at least one polycarboxylic acid or its derivative selected from (d) glutaric acid, adipic acid, sebacic acid, homologs of the foregoing, phthalic acid or its isomers, trimellitic acid, cyclic anhydrides of the foregoing, or maleic acid anhydride, (2) said alcohol is: ethylene glycol, propylene glycol, neopentyl glycol, or the dimers, trimers, homologs of the foregoing containing up to 8 carbon atoms, or isomers of the foregoing; alcohols having a functionality higher than 3 which are glycerol, trimethylol ethane, trimethylol propane, pentaerythritol, dipentaenythritol, sorbitol, or any mixture of the above, and said condensation reaction is conducted at a temperature of about from 120° to 220° C. and is continued until the acid number of the precondensate is less than 2; (B) converting said precondensate into an acidic precondensate by further condensation with a polycarboxylic acid anhydride wherein said carboxylic acid anhydride is at least one of succinic acid anhydride, glutaric acid anhydride, maleic acid anhydride, phthalic acid anhydride, or trimellitic acid anhydride, and said further condensation is conducted at a temperature of about from 140° to 200° C. and continued until an acid number of about 50 to 130 is obtained; (C) forming an alkyd resin by further esterification of said acidic precondensate with a further alcohol wherein said further alcohol is at least one of: glycerol; trimethylol ethane; trimethylol propane; pentaerythritol; the dimerization products of glycerol, trimethylol ethane or trimethylol propane; reaction products of any of the foregoing with up to 5 mols of ethylene oxide or propylene oxide; a polyol having 4 to 10 hydroxyl group selected from sorbitol, a polyglycerol with 2 to 4 ether oxygens, depentaerythritol, the reaction products of any of the foregoing polyols having 4 to 10 hydroxyl groups with up to 10 mols of ethylene oxide or propylene oxide; or any mixture thereof, said further esterification reaction is conducted at a temperature of about from 120° to 220° C. and is continued until an acid number of about 10 to 40 is obtained; and (D) forming an alkyd resin emulsion by mixing said alkyd resin with an aminoalcohol present in an amount sufficient to neutralize said alkyd resin, an emulsifier present when said alkyd resins contain fatty acids whose average chain length is greater than C 16 , and water, wherein: said aminoalcohol is: methylaminopropanol; methylaminopropane diol; tris-hydroxymethylaminomethane; reaction products of the foregoing with ethylene oxide; diethanolamine, triethanolamine; methyldiethanolamine; or any mixture thereof, and said emulsifier is at least one salt of an aminoalcohol with a 10,9- or 9,10-hydroxyalkoxystearic acid wherein said alkoxy radical is derived from: glycerol, trimethylol propane, pentaerythritol, or sorbitol; the autocondensation products of the foregoing alcohols; the reaction products of the foregoing alcohols with up to 10 mols of ethylene oxide per mol of alcohol, or any mixtures of the above, and said water is present in 25% to 5% by weight.

Claim 22

A process for synthesizing alkyd resin compositions comprising: (A) condensing a carboxylic acid with an alcohol to form a polyester precondensate having terminal hydroxyl groups wherein (1) said carboxylic acid is a mixture of naturally occurring fatty acids selected from one of (a) C 8-18 fractionated coconut oil fatty acids in which at least 40% by weight is lauric acid, at least 10% by weight is myristic acid, and at least 10% by weight is palmitic acid, (b) C 14-18 selectively hardened tallow fatty acids in which at least 35% by weight is oleic acid, at least 20% by weight is palmitic acid, and at least 20% by weight is stearic acid, or (c) predominantly C 8-12 fractionated fatty acids in which at least 55% by weight is caprylic acid and at least 30% by weight is capric acid, or said carboxylic acid is at least one polycarboxylic acid or its derivative selected from (d) glutaric acid, adipic acid, sebacic acid, homologs of the foregoing, phthalic acid or its isomers, trimellitic acid, cyclic anhydrides of the foregoing, or maleic acid anhydride, (2) said alcohol is: ethylene glycol, propylene glycol, neopentyl glycol, or the dimers, trimers, homologs of the foregoing containing up to 8 carbon atoms, or isomers of the foregoing; alcohols having a functionality higher than 3 which are glycerol, trimethylol ethane, trimethylol propane, pentaerythritol, dipentaenythritol, sorbitol, or any mixture of the above, and said condensation reaction is conducted at a temperature of about from 120° to 220° C. and is continued until the acid number of the precondensate is less than 2; (B) converting said precondensate into an acidic precondensate by further condensation with a polycarboxylic acid anhydride wherein said carboxylic acid anhydride is at least one of succinic acid anhydride, glutaric acid anhydride, maleic acid anhydride, phthalic acid anhydride, or trimellitic acid anhydride, and said further condensation is conducted at a temperature of about from 140° to 200° C. and continued until an acid number of about 50 to 130 is obtained; (C) forming an alkyd resin by further esterification of said acidic precondensate with a further alcohol wherein said further alcohol is at least one of: glycerol; trimethylol ethane; trimethylol propane; pentaerythritol; the dimerization products of glycerol, trimethylol ethane or trimethylol propane; reaction products of any of the foregoing with up to 5 mols of ethylene oxide or propylene oxide; a polyol having 4 to 10 hydroxyl group selected from sorbitol, a polyglycerol with 2 to 4 ether oxygens, depentaerythritol, the reaction products of any of the foregoing polyols having 4 to 10 hydroxyl groups with up to 10 mols of ethylene oxide or propylene oxide; or any mixture thereof, said further esterification reaction is conducted at a temperature of about from 120° to 220° C. and is continued until an acid number of about 10 to 40 is obtained; and (D) forming an alkyd resin emulsion by mixing said alkyd resin with an aminoalcohol present in an amount sufficient to neutralize said alkyd resin, an emulsifier present when said alkyd resins contain fatty acids whose average chain length is greater than C 16 , and water, wherein: said aminoalcohol is: methylaminopropanol; methylaminopropane diol; tris-hydroxymethylaminomethane; reaction products of the foregoing with ethylene oxide; diethanolamine, triethanolamine; methyldiethanolamine; or any mixture thereof, and said emulsifier is at least one salt of an aminoalcohol with a 10,9- or 9,10-hydroxyalkoxystearic acid wherein said alkoxy radical is derived from: glycerol, trimethylol propane, pentaerythritol, or sorbitol; the autocondensation products of the foregoing alcohols; the reaction products of the foregoing alcohols with up to 10 mols of ethylene oxide per mol of alcohol, or any mixtures of the above, and said water is present in 25% to 5% by weight.

Claim 23

The product of the process of claim 1.

Claim 24

The product of the process of claim 2.

Claim 25

The product of the process of claim 3.

Claim 26

The product of the process of claim 5.

Claim 27

The product of the process of claim 6.

Claim 28

The product of the process of claim 8.

Claim 29

The product of the process of claim 11.

Claim 30

The product of the process of claim 12.

Claim 31

The product of the process of claim 15.

Claim 32

The product of the process of claim 16.

Claim 33

The product of the process of claim 20.