Polyurethanes made using mixtures of tertiary amine compounds and lewis acids as catalysts

Patent metadata

Field	Value
Publication number	US-9969837-B2
Application number	US-201214240596-A
Country	US
Kind code	B2
Filing date	Aug 29, 2012
Priority date	Sep 21, 2011
Publication date	May 15, 2018
Grant date	May 15, 2018

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 tertiary amine catalyst having a molecular weight of up to 300 and from 0.01 to 1.0 mole per mole of the tertiary amine compound(s) of a non-protic, non-catalytic, metal-containing Lewis acid.

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 a polymer, wherein the catalyst comprises a mixture of at least one tertiary amine compound having a molecular weight of up to 300 and from 0.01 to 1.0 mole, per mole of tertiary amine compound(s) having a molecular weight of up to 300, of a non-catalytic, non-protic, metal-containing Lewis acid selected from one or more of dibutyl calcium, butylethyl calcium, lanthanum isopropoxide, and lanthanum tris-(bis(trimethylsilyl)amide).

2. The process of claim 1 , wherein the tertiary amine compound having a molecular weight of up to 300 is one or more of trimethylamine, triethylamine, dimethylethanolamine, N-methylmorpholine, N-ethylmorpholine, N,N-dimethylbenzylamine, N,N-dimethylethanolamine, N,N,N′,N′-tetramethyl-1,4-butanediamine, N,N-dimethylpiperazine, tetramethylguanidine, 1,4-diazobicyclo-2,2,2-octane, bis(dimethylaminoethyl)ether, bis(2-dimethylaminoethyl) ether, morpholine, 4,4′-(oxydi-2,1-ethanediyl)bis, triethylenediamine, pentamethyl diethylene triamine, dimethyl cyclohexyl amine, N-cetyl-N,N-dimethyl amine, N-coco-morpholine, N,N-dimethyl aminomethyl N-methyl ethanol amine, N,N,N′-trimethyl-N′-hydroxyethyl bis(aminoethyl) ether, N,N-bis(3-dimethylaminopropyl)N-isopropanolamine, (N,N-dimethyl) amino-ethoxy ethanol, N,N,N′,N′-tetramethyl hexane diamine, N,N-dimorpholinodiethyl ether, N-methyl imidazole, dimethyl aminopropyl dipropanolamine, bis(dimethylaminopropyl)amino-2-propanol, tetramethylamino bis (propylamine), (dimethyl(aminoethoxyethyl))((dimethyl amine) ethyl) ether, tris(dimethylamino propyl) amine, dicyclohexyl methyl amine, bis(N,N-dimethyl-3-aminopropyl) amine, 1,2-ethylene piperidine and methyl-hydroxyethyl piperazine.

3. The process of claim 1 wherein the tertiary amine compound having a molecular weight of up to 300 is a bicyclic amidine or substituted bicyclic amidine.

4. The process of claim 3 wherein the tertiary amine compound is 1,8-diazobicyclo-5.4.0-undecene-7,6-(dibutylamino)-1,8-diazabicyclo[5.4.0]undec-7-ene, or a mixture thereof.

5. The process of claim 1 wherein the reaction mixture contains from 0.05 to 1.0 moles of the non-catalytic, non-protic metal-containing Lewis acid per mole of the tertiary amine compound(s) having a molecular weight of up to 300.

6. The process of claim 5 wherein the reaction mixture contains from 0.05 to 0.5 moles of the non-catalytic, non-protic metal-containing Lewis acid per mole of the tertiary amine compound(s) having a molecular weight of up to 300.

7. The process of claim 1 wherein the reaction mixture contains from 0.01 to 5 parts by weight of the tertiary amine compound(s) having a molecular weight of up to 300 per 100 parts by weight of the isocyanate-reactive compounds.

8. The process of claim 1 wherein the reaction mixture contains no more than 0.1 mole of a Brønsted acid having a pKa of 5 or less in water at 25° C. per mole of the tertiary amine compound(s) having a molecular weight of up to 300.

9. 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 chain extender and at least one polyol having a hydroxyl equivalent weight of at least 250.

10. The process of claim 1 wherein the non-catalytic, non-protic metal-containing Lewis acid and the tertiary amine compound(s) having a molecular weight of up to 300 are mixed together prior to contacting the organic polyisocyanate compound with the isocyanate-reactive material.

11. The process of claim 1 wherein the non-catalytic, non-protic, metal-containing Lewis acid—selected from one or more of lanthanum isopropoxide and lanthanum tris-(bis(trimethylsilyl)amide).

Assignees

• Duggal Rajat
• Wilmot Nathan
• Keaton Richard J
• Romer Duane R
• Margl Peter M
• Dow Global Technologies Llc

Inventors

• Duggal Rajat
• Wilmot Nathan
• Keaton Richard J
• Romer Duane R
• Margl Peter M

Classifications

• C08G18/2063 Primary

  having two nitrogen atoms in the condensed ring system · CPC title

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• C08G18/163

  covered by C08G18/18 and C08G18/22 · CPC title

• C08G18/4837

  and other oxyalkylene units · CPC title

• C08G18/18

  containing secondary or tertiary amines or salts thereof · CPC title