Polyurethanes made using bismuth thiophosphoric acid diester salts as catalysts

Patent metadata

Field	Value
Publication number	US-9340639-B2
Application number	US-201314390714-A
Country	US
Kind code	B2
Filing date	Mar 26, 2013
Priority date	Apr 25, 2012
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

Polyisocyanate-based polymers are formed by curing a reaction mixture containing at least one polyisocyanate and at least one isocyanate-reactive compound having at least two isocyanate-reactive groups in the presence of a bismuth thiophosphoric acid diester salt.

First claim

What is claimed is:

1. A process for preparing a polyisocyanate-based polymer, comprising forming a reaction mixture containing at least one polyisocyanate, at least one isocyanate-reactive compound having at least two isocyanate-reactive groups and at least one catalyst, and then curing the reaction mixture to form the polyisocyanate-based polymer, wherein the catalyst includes a bismuth salt of a thiophosphoric acid diester having the formula Bi 3+ A 3 , wherein each A group is independently

where each X is independently oxygen or sulfur, each R′ is independently hydrogen or alkyl or the R′ groups together form a covalent bond or a divalent linking radical that completes a ring structure with the —(X)—P—(X)— linkage, and further wherein the bismuth salt is present in an amount from 0.01 to 3 millimoles per kilogram of polyisocyanate(s) and isocyanate-reactive compounds present in the reaction mixture.

2. The process of claim 1 wherein the R′ groups in structure IV are unsubstituted alkyl.

3. The process of claim 1 wherein the R′ groups in structure IV together form a divalent organic radical that completes a ring structure with the —(X)—P—(X)— linkage.

4. The process of claim 1 wherein the bismuth thiophosphoric acid diester salt is the sole metal-containing catalyst present.

5. The process of claim 1 wherein the bismuth salt is present in an amount from 0.075 to 0.5 millimoles per kilogram of polyisocyanate(s) and isocyanate-reactive) compounds present in the reaction mixture.

6. The process of claim 1 wherein the reaction mixture contains at least one activator for the bismuth salt.

7. The process of claim 6 wherein the activator includes at least one aluminosilicate.

8. The process of claim 7 wherein the aluminosilicate is a molecular sieve or a zeolite.

9. The process of claim 6 wherein the activator includes at least one inorganic or organic base.

10. The process of claim 9 wherein the activator is a compound that contains one or more tertiary amino groups.

11. The process of claim 10 wherein the compound that contains one or more tertiary amino groups is present in an amount of not more than 5 millimoles per kilogram of polyisocyanate(s) and isocyanate-reactive compound(s) present in the reaction mixture.

12. The process of claim 11 wherein the compound that contains one or more tertiary amino groups is present in an amount from 0.5 to 3 moles of tertiary amine activator per mole of the bismuth salt.

13. The process of claim 12 wherein the compound that contains one or more tertiary amino compounds is an amidine compound.

14. The process of claim 1 wherein the polyisocyanate-based polymer is a cast elastomer, the polyisocyanate is a prepolymer or quasi-prepolymer and the isocyanate-reactive compound is a chain extender or mixture of a chain extender and at least one polyol having a hydroxyl equivalent weight of at least 250.

15. The process of claim 14 wherein the cast elastomer is microcellular and has a density of at least 500 kg/m 3 .

16. The process of claim 14 wherein the cast elastomer is noncellular.

17. A process for preparing a polyisocyanate-based polymer, comprising forming a reaction mixture containing at least one polyisocyanate, at least one isocyanate-reactive compound having at least two isocyanate-reactive groups and at least one catalyst, and then curing the reaction mixture to form the polyisocyanate-based polymer, wherein the catalyst includes a bismuth salt of a thiophosphoric acid diester having the structure:

wherein each X is independently oxygen or sulfur, each R is independently hydrogen or alkyl, each R 2 is a covalent bond or a divalent linking group, n is a number from 1 to 3, and L is an anion other than a thiophosphorate diester anion.

Assignees

• Keaton Richard J
• Margl Peter M
• Duggal Rajat
• Boelter Scott D
• Romer Duane R
• Nowlin Debra L
• Wilmot Nathan
• Wilson David R
• Welsh Dean M
• Dow Global Technologies Llc

Inventors

• Keaton Richard J
• Margl Peter M
• Duggal Rajat
• Boelter Scott D
• Romer Duane R
• Nowlin Debra L
• Wilmot Nathan
• Wilson David R
• Welsh Dean M

Classifications

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/797

  containing carbodiimide and/or uretone-imine groups · CPC title

• C08G2101/0066

  Chemistry & Metallurgy · mapped topic

• C08G18/14

  Manufacture of cellular products · CPC title

• C08G18/3206

  aliphatic · CPC title