Polyurethanes

Patent metadata

Field	Value
Publication number	US-9815939-B2
Application number	US-201314422554-A
Country	US
Kind code	B2
Filing date	Aug 15, 2013
Priority date	Aug 23, 2012
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

The present invention relates to a polyurethane which is the reaction product of a polyisocyanate and polyester, wherein said polyester is formed from a dimer fatty acid, a C 2 to C 4 diol, and a C 8 to C 16 dicarboxylic acid or C 6 to C 12 lactide. The inventions also relates to a polyester for use in forming the polyurethane of the first aspect, said polyester formed from a dimer fatty acid, a C 2 to C 4 diol, and a C 8 to C 16 dicarboxylic acid or C 6 to C 12 lactide.

First claim

The invention claimed is:

1. A polyurethane, said polyurethane being the reaction product of a polyisocyanate and polyester, wherein said polyester is formed from a dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids, a diol selected from propanediol or butanediol, and a C 10 or C 12 linear aliphatic dicarboxylic acid, wherein the ratio of the dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids to the C 10 to C 12 linear aliphatic dicarboxylic acid ranges from about 25:75 to about 50:50, wherein the polyester has a molecular weight number average in the range from 800 to 5,000 and wherein a particle size of the polyurethane is 150 nm or less.

2. The polyurethane according to claim 1 , wherein the dimer fatty acid is derived from the dimerisation products of oleic acid, linoleic acid, linolenic acid, palmitoleic acid, and/or elaidic acid.

3. The polyurethane according to claim 1 , wherein the dimer fatty acid has a dimer fatty acid content of greater than 60 wt.%.

4. The polyurethane according to claim 1 , wherein the propanediol or butanediol has a renewable carbon content of at least 50% when determined using ASTM D6866.

5. The polyurethane according to claim 1 , wherein the dicarboxylic acid is a non-dimeric dicarboxylic acid.

6. The polyurethane according to claim 1 , wherein the dicarboxylic acid is selected from sebacic acid (decanedioic acid), dodecane dicarboxylic acid (dodecanedioic acid), or combinations thereof.

7. The polyurethane according to claim 5 , wherein the dicarboxylic acid has a renewable carbon content of at least 50% when determined using ASTM D6866.

8. The polyurethane according to claim 1 , wherein the ratio of carbon atoms of propanediol or butanediol to the ratio of carbon atoms in the dicarboxylic acid is in the range from 1:1.5 to 12 respectively.

9. The polyurethane according to claim 1 , wherein the polyester is formed from dimer fatty acid; C 10 or C 12 linear aliphatic dicarboxylic acids; and 1,3 propanediol or 1,4 butane diol at a weight ratio in the range from 0.3 to 0.5:0.5 to 0.7:1.0 to 3.0 respectively.

10. The polyurethane according to claim 1 , wherein the polyester has a glass transition temperature (T g ) value in the range from −60° C. to 0° C.

11. A method of forming polyurethane in accordance with claim 1 , the method comprising;
forming polyester from a dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids, a diol selected from propanediol or butanediol, and a C 10 or C 12 linear aliphatic dicarboxylic acid, wherein the ratio of the dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids to the C 10 to C 12 linear aliphatic dicarboxylic acid ranges from about 25:75 to about 50:50, wherein the polyester has a molecular weight number average in the range from 800 to 5,000; and
reacting said polyester with a polyisocyanate to form polyurethane having a particle size of 150 nm or less.

12. A method of forming polyurethane in accordance with claim 1 , the method comprising;
forming polyester from a dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids, a diol selected from propanediol or butanediol, and a C 10 or C 12 linear aliphatic dicarboxylic acid, wherein the ratio of the dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids to the C 10 to C 12 linear aliphatic dicarboxylic acid ranges from about 25:75 to about 50:50, wherein the polyester has a molecular weight number average in the range from 800 to 5,000; and
reacting said polyester with polyisocyanate to form an isocyanate-terminated prepolymer; and reacting said prepolymer with a chain extender to form a polyurethane having a particle size of 150 nm or less.

13. The method according to claim 11 , wherein the polyisocyanate comprises at least one isocyanate which has a functionality of at least 2.

14. The method according to claim 12 , wherein the chain extender is a diol having an aliphatic linear carbon chain comprising in the range from 1 to 10 carbon atoms.

15. The method according to claim 12 , wherein the molar ratio of chain extender to polyester is in the range from 1 to 10:1.

16. An isocyanate-terminated pre-polymer which is a reaction product of polyisocyanate and polyester, wherein said polyester is formed from a dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids, a diol selected from propanediol or butanediol, and a C 10 or C 12 linear aliphatic dicarboxylic acid, wherein the ratio of the dimer fatty acid derived from the dimerization products of C 14 to C 22 fatty acids to the C 10 to C 12 linear aliphatic dicarboxylic acid ranges from about 25:75 to about 50:50, wherein the polyester has a molecular weight number average in the range from 800 to 5,000 and wherein the pre-polymer has a particle size of 150 nm or less.

17. An adhesive, coating, or elastomer composition comprising polyurethane in accordance with claim 1 .

Assignees

• Croda Int Plc

Inventors

• Smits Angela Leonarda Maria
• Van Der Helm-Rademaker Karin

Classifications

• C08G18/0866

  the dispersing or dispersed phase being an aqueous medium · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C08G18/6659 Primary

  with compounds of group C08G18/34 · CPC title

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• C08G63/553

  Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts · CPC title