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

Patent metadata

Field	Value
Publication number	US-9657134-B2
Application number	US-201213712110-A
Country	US
Kind code	B2
Filing date	Dec 12, 2012
Priority date	Sep 1, 2004
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

The present invention provides polyurethanes including a reaction product of components including: (a) about 1 equivalent of at least one polyisocyanate; (b) about 0.05 to about 1 equivalents of at least one branched polyol having 4 to 18 carbon atoms and at least 3 hydroxyl groups; (c) about 0.01 to about 0.3 equivalents of at least one polycarbonate diol; and (d) about 0.1 to about 0.9 equivalents of at least one polyol different from the branched polyol and having 2 to 18 carbon atoms, wherein the reaction product components are essentially free of polyether polyol and the reaction components are maintained at a temperature of at least about 100° C. for at least about 10 minutes; compositions, coatings and articles made therefrom and methods of making the same.

First claim

What is claimed is:

1. The polyurethane comprising a reaction product of components comprising:
(a) an isocyanate functional urethane prepolymer comprising a reaction product of components comprising:
(i) about 1 equivalent of at least one polyisocyanate; and
(ii) about 0.3 to about 0.4 equivalents of cyclohexane dimethanol; and

(b) about 0.1 to about 0.3 equivalents of trimethylolpropane, based upon the about 1 equivalent of at least one polyisocyanate (i);
(c) about 0.4 to about 0.5 equivalents of cyclohexane dimethanol, based upon the about 1 equivalent of at least one polyisocyanate (i); and
(d) about 0.01 to about 0.3 equivalents of at least one polycarbonate diol, based upon the about 1 equivalent of at least one polyisocyanate (i),
wherein the reaction components comprise less than about 5 weight percent of polyether polyol; wherein the prepolymer (a), the trimethylolpropane (b), the cyclohexane dimethanol (c), and the polycarbonate diol (d) are each preheated to and maintained at a temperature of at least about 100° C. for at least about 10 minutes immediately prior to mixing together within a mixing chamber of a dynamic pin mixer, degassed, and reacted at a temperature of at least about 110° C. for at least about 6 hours; and wherein the mixing chamber has a volume of about 62 cc to about 250 cc, the total flow rate components in the mixing chamber is about 499 to about 4807 grams per minute and the residence time of the components in the mixing chamber is from about 0.1 seconds to about 15 minutes.

2. The polyurethane according to claim 1 , wherein the polyisocyanate is selected from the group consisting of diisocyanates, triisocyanates, dimers, trimers and mixtures thereof.

3. The polyurethane according to claim 1 , wherein the polyisocyanate is selected from the group consisting of ethylene diisocyanate, trimethylene diisocyanate, 1,6-hexamethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, decamethylene diisocyanate, 1,6,11-undecane-triisocyanate, 1,3,6-hexamethylene triisocyanate, bis(isocyanatoethyl)-carbonate, bis(isocyanatoethyl)ether, trimethylhexane diisocyanate, trimethylhexamethylene diisocyanate, 2,2′-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, 2,4,4,-trimethylhexamethylene diisocyanate, 1,8-diisocyanato-4-(isocyanatomethyl)octane, 2,5,7-trimethyl-1,8-diisocyanato-5-(isocyanatomethyl)octane, 2-isocyanatopropyl-2,6-diisocyanatohexanoate, lysinediisocyanate methyl ester, 4,4′-methylene-bis-(cyclohexyl isocyanate), 4,4′-isopropylidene-bis-(cyclohexyl isocyanate), 1,4-cyclohexyl diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3-isocyanato methyl-3,5,5-trimethylcyclohexyl isocyanate, meta-tetramethylxylylene diisocyanate, diphenyl methane diisocyanates, diphenyl isopropylidene diisocyanate, diphenylene diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, bis(isocyanatomethyl) cyclohexane, bis(isocyanatocyclohexyl)methane, bis(isocyanatocyclohexyl)-2,2-propane, bis(isocyanatocyclohexyl)-1,2-ethane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-5-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanato-methyl-2-(3-isocyanatopropyl)-6-isocyanatomethyl-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-3-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)-bicyclo[2.2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-5-(2-isocyanatoethyl)-bicyclo-[2.2.1]-heptane, 2-isocyanatomethyl-2-(3-isocyanatopropyl)-6-(2-isocyanatoethyl)-bicyclo[2.2.1]-heptane, α,α′-xylene diisocyanate, bis(isocyanatoethyl)benzene, α,α,α′,α′-tetramethylxylene diisocyanate, 1,3-bis(1-isocyanato-1-methylethyl) benzene, bis(isocyanatobutyl)benzene, bis(isocyanatomethyl)naphthalene, bis(isocyanatomethyl)diphenyl ether, bis(isocyanatoethyl) phthalate, mesitylene triisocyanate, 2,5-di(isocyanatomethyl)furan, α,α′-xylene diisocyanate, bis(isocyanatoethyl)benzene, α,α,α′,α′-tetramethylxylene diisocyanate, 1,3-bis(1-isocyanato-1-methylethyl)benzene, bis(isocyanatobutyl) benzene, bis(isocyanatomethyl)naphthalene, bis(isocyanatomethyl)diphenyl ether, bis(isocyanatoethyl) phthalate, 2,5-di(isocyanatomethyl)furan, diphenylether diisocyanate, bis(isocyanatophenylether)ethyleneglycol, bis(isocyanatophenylether)-1,3-propyleneglycol, benzophenone diisocyanate, carbazole diisocyanate, ethylcarbazole diisocyanate, dichlorocarbazole diisocyanate, and dimers, trimers and mixtures thereof.

4. The polyurethane according to claim 1 , wherein the polyisocyanate is dicyclohexylmethane diisocyanate.

5. The polyurethane according to claim 1 , wherein the polycarbonate diol is polyhexylene carbonate diol.

6. The polyurethane according to claim 1 , wherein the reaction components comprise less than about 0.1 equivalents of polyether polyol.

7. The polyurethane according to claim 1 , wherein the reaction components are essentially free of amine curing agent.

8. The polyurethane according to claim 1 , wherein the reaction components further comprise one or more polyurethane polyols, polyvinyl alcohols, hydroxy functional acrylates, hydroxy functional methacrylates, allyl alcohols, dihydroxy oxamides, dihydroxyamides, dihydroxy piperidines, dihydroxyethyl hydroquinones and mixtures thereof.

9. The polyurethane according to claim 1 , wherein, after mixing, the reaction components are maintained at a temperature of at least about 110° C. for at least about 10 minutes prior to curing.

10. The polyurethane according to claim 1 , wherein, after mixing, reaction components are maintained at a temperature of at least about 100° C. for at least about 20 minutes prior to curing.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Rukavina Thomas G
• Hunia Robert M
• Harris Caroline S
• Frain Veronica L

Classifications

• C08G18/6607

  with compounds of group C08G18/3203 · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/765

  alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• C08G18/3872

  the sulfur atom belonging to a sulfoxide or sulfone group · CPC title

• C08G18/4018

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