Polyurethanes, articles and coatings prepared therefrom and methods of making the same

Patent metadata

Field	Value
Publication number	US-9464169-B2
Application number	US-201414212192-A
Country	US
Kind code	B2
Filing date	Mar 14, 2014
Priority date	Sep 1, 2004
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

The present invention provides polyurethanes including a reaction product of components including: (a) at least one isocyanate functional prepolymer including a reaction product of: (1) about 1 equivalent of at least one polyisocyanate; and (2) about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol; and (b) about 0.01 to about 1 equivalent of at least one branched polyol having at least 3 hydroxyl groups; compositions, coatings and articles made therefrom and methods of making the same.

First claim

What is claimed is:

1. A polyurethane comprising a reaction product of components comprising:
(a) at least one isocyanate functional prepolymer comprising a reaction product of:
(1) about 1 equivalent of at least one polyisocyanate; and
(2) about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate; and
(b) about 0.01 to about 1 equivalent of at least one polyol having at least 3 hydroxyl groups based upon the about 1 equivalent of the at least one polyisocyanate,
wherein the components further comprise about 0.01 to about 0.5 equivalent of water based upon the about 1 equivalent of the at least one polyisocyanate.

2. The polyurethane according to claim 1 , wherein the water is reacted with the polyisocyanate and polycarbonate polyol to form an isocyanate functional ureaurethane prepolymer.

3. A polyurethane comprising a reaction product of components comprising:
(a) about 1 equivalent of at least one polyisocyanate;
(b) about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate; and
(c) about 0.01 to about 1 equivalent of at least one polyol having at least 3 hydroxyl groups based upon the about 1 equivalent of the at least one polyisocyanate, and
(d) about 0.01 to about 0.5 equivalent of water based upon the about 1 equivalent of the at least one polyisocyanate.

4. A process for preparing a polyurethane article comprising:
(a) heating a mixture of about 1 equivalent of at least one polyisocyanate and about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate, to a temperature of about 110° C. to about 130° C. for at least about an hour to form a reaction product;
(b) mixing the reaction product (a) with about 0.01 to about 1 equivalent of at least one polyol having at least 3 hydroxyl groups based upon the about 1 equivalent of the at least one polyisocyanate until the mixture reaches a temperature of at least about 110° C. to about 130° C., optionally by heating if necessary;
(c) casting the reaction product into a mold preheated to a temperature of at least about 100° C. to about 130° C.; and
(d) curing the reaction product at a first predetermined temperature of about 100° C. to about 120° C. for at least about 0.5 hours; and then at a second predetermined temperature of about 140° C. to about 180° C. for about 15 to about 30 hours,
wherein the at least one polyol of step (b) is selected from the group consisting of glycerol, glycerin, tetramethylolmethane, trimethylolmethane, trimethylolpropane, erythritol, pentaerythritol.

5. The process of claim 4 , wherein the polyisocyanate of step (a) is selected from the group consisting of diisocyanates, triisocyanates, dimers, trimers and mixtures thereof.

6. The process of claim 4 , wherein the polycarbonate polyol of step (a) is prepared from hexanediol and dialkyl carbonate.

7. The process of claim 4 , wherein the at least one polyol of step (b) is trimethylolpropane.

8. The process of claim 4 , wherein step (b) further comprises mixing about 0.001 to about 0.5 equivalent of at least one polyol different from the at least one polyol of step (b), based upon the about 1 equivalent of the at least one polyisocyanate, with the reaction product (a) and the at least one polyol of step (b).

9. The process of claim 8 , wherein the at least one polyol different from the at least one polyol of step (b) is a diol.

10. The process of claim 8 , wherein the at least one polyol different from the at least one polyol of step (b) is selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-ethanediol, propanediol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, dodecane diol, sorbitol, mannitol, cyclopentanediol, 1,4-cyclohexanediol, cyclohexanedimethanol, 1,4-benzenedimethanol, xylene glycol, hydroxybenzyl alcohol, dihydroxytoluene bis(2-hydroxyethyl) terephthalate, 1,4-bis(hydroxyethyl)piperazine, N,N′,bis(2-hydroxyethyl)oxamide and mixtures thereof.

11. The process of claim 4 , wherein the mixture of step (a) and/or step (b) further comprises one or more polyurethane polyols, acrylamides, polyvinyl alcohols, hydroxy functional acrylates, hydroxy functional methacrylates, allyl alcohols, dihydroxy oxamides, dihydroxyamides, dihydroxy piperidines, dihydroxy phthalates, dihydroxyethyl hydroquinones and mixtures thereof.

12. The process of claim 4 , comprising:
(a) heating a mixture of about 1 equivalent of at least one polyisocyanate and about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate, to a temperature of about 110° C. to about 130° C. for at least about an hour to form a reaction product;
(b) mixing the reaction product (a) with about 0.5 to about 0.8 equivalent of trimethylolpropane based upon the about 1 equivalent of the at least one polyisocyanate and about 0.1 to about 0.5 equivalent of butanediol, pentanediol or cyclohexane dimethanol based upon the about 1 equivalent of the at least one polyisocyanate until the mixture reaches a temperature of at least about 110° C. to about 130° C., optionally by heating if necessary;
(c) casting the reaction product into a mold preheated to a temperature of at least about 100° C. to about 130° C.; and
(d) curing the reaction product at a first predetermined temperature of about 100° C. to about 120° C. for at least about 0.5 hours; and then at a second predetermined temperature of about 140° C. to about 180° C. for about 15 to about 30 hours.

13. The process of claim 4 , comprising:
(a) heating a mixture of about 1 equivalent of at least one polyisocyanate and about 0.2 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate, to a temperature of about 110° C. to about 130° C. for at least about an hour to form a reaction product;
(b) mixing the reaction product (a) with about 0.7 equivalent of trimethylolpropane based upon the about 1 equivalent of the at least one polyisocyanate and about 0.1 equivalent of butanediol, pentanediol or cyclohexane dimethanol based upon the about 1 equivalent of the at least one polyisocyanate until the mixture reaches a temperature of at least about 110° C. to about 130° C., optionally by heating if necessary;
(c) casting the reaction product into a mold preheated to a temperature of at least about 100° C. to about 130° C.; and
(d) curing the reaction product at a first predetermined temperature of about 100° C. to about 120° C. for at least about 0.5 hours; and then at a second predetermined temperature of about 140° C. to about 180° C. for about 15 to about 30 hours.

14. A polyurethane article prepared by a process comprising:
(a) heating a mixture of about 1 equivalent of at least one polyisocyanate and about 0.01 to about 0.5 equivalent of at least one polycarbonate polyol based upon the about 1 equivalent of the at least one polyisocyanate, to a temperature of about 110° C. to about 130° C. for at least about an hour to form a reaction product;
(b) mixing the reaction product (a) with about 0.01 to about 1 equivalent of at least one polyol having at least 3 hydroxyl groups based upon the about 1 equivalent of the at least one polyisocyanate until the mixture reaches a temperature of at least about 110° C. to about 130° C., optionally by heating if necessary;
(c) casting the reaction product into a mold preheated t

Assignees

• Ppg Ind Ohio Inc

Inventors

• Rukavina Thomas G

Classifications

• B32B2605/18

  Aircraft · CPC title

• C08G18/6644

  having at least three hydroxy groups · CPC title

• C08G18/3212

  containing cycloaliphatic groups · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• C08G18/664

  with compounds of group C08G18/3203 · CPC title