Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same

• US 20070149747A1
• Filed: 12/14/2006
• Published: 06/28/2007
• Est. Priority Date: 09/01/2004
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Hunia, Robert, Rukavina, Thomas
• Granted Patent: US 8,859,680 B2
• Time in Patent Office: Days
• US Class Current: 528/44
• CPC Class Codes: B32B 17/1077 containing polyurethane
• CPC Class Codes: B32B 2307/412 Transparent
• CPC Class Codes: B32B 2307/558 Impact strength, toughness
• CPC Class Codes: B32B 2307/584 Scratch resistance
• CPC Class Codes: B32B 2307/71 Resistive to light or to UV
• CPC Class Codes: B32B 2307/712 Weather resistant
• CPC Class Codes: B32B 2457/20 Displays, e.g. liquid crystal displays, plasma displays
• CPC Class Codes: B32B 2551/00 Optical elements
• CPC Class Codes: B32B 2571/02 defensive, e.g. armour plates or anti-ballistic clothing
• CPC Class Codes: B32B 2605/006 Transparent parts other than made from inorganic glass, e.g. polycarbonate glazings
• CPC Class Codes: B32B 2605/18 Aircraft
• CPC Class Codes: B32B 27/40 comprising polyurethanes
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/305 creating amino end groups
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3212 containing cycloaliphatic groups
• CPC Class Codes: C08G 18/3215 containing aromatic groups or benzoquinone groups
• CPC Class Codes: C08G 18/3284 containing four hydroxy groups
• CPC Class Codes: C08G 18/381 having bromine atoms
• CPC Class Codes: C08G 18/3868 : the sulfur atom belonging to a sulfide group
• CPC Class Codes: C08G 18/3872 : the sulfur atom belonging to a sulfoxide or sulfone group
• CPC Class Codes: C08G 18/4018 : Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
• CPC Class Codes: C08G 18/44 : Polycarbonates
• CPC Class Codes: C08G 18/6607 : with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/6644 : having at least three hydroxy groups
• CPC Class Codes: C08G 18/671 : Unsaturated compounds having only one group containing active hydrogen takes precedence on groups C08G18/675 - C08G18/69
• CPC Class Codes: C08G 18/724 : Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates
• CPC Class Codes: C08G 18/758 : containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 18/765 : alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C08G 18/7657 : containing two or more aromatic rings
• CPC Class Codes: C08G 18/792 : formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates

Abstract

The present invention provides poly(ureaurethane)s including a reaction product of components comprising: (a) at least one polyisocyanate selected from the group consisting of polyisocyanate trimers and branched polyisocyanates, the polyisocyanate having at least three isocyanate functional groups; (b) about 0.1 to about 0.9 equivalents of at least one polyol having 4 to 18 carbon atoms and at least 2 hydroxyl groups; and (c) at least one amine curing agent, wherein the reaction product components are essentially free of polyester polyol and polyether polyol; compositions, coatings and articles made therefrom and methods of making the same.

Claims

1. A poly(ureaurethane) comprising a reaction product of components comprising:

(a) at least one polyisocyanate selected from the group consisting of polyisocyanate trimers and branched polyisocyanates, the polyisocyanate having at least three isocyanate functional groups;

(b) about 0.1 to about 0.9 equivalents of at least one polyol having 4 to 18 carbon atoms and at least 2 hydroxyl groups; and

(c) at least one amine curing agent,

wherein the reaction product components are essentially free of polyester polyol and polyether polyol.

2. The poly(ureaurethane) according to claim 1, wherein the polyisocyanate is a trimer of a diisocyanate selected from the group consisting of hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylylene diisocyanate, and mixtures thereof.

3. The poly(ureaurethane) according to claim 1, wherein the polyisocyanate is a branched polyisocyanate selected from the group consisting of 2,4,6-trioxo-1,3,5-tris(6-isocyanatohexyl)hexahydro-1,3,5-triazine, 2,4,6-trioxo-1,3,5-tris(5-isocyanato-1,3,3-trimethylcyclohexylmethyl)hexahydro-1,3,5-triazine, tris(4-iso-cyanatophenyl)methane, 1,3,5-tris(3-isocyanato-4-methylphenyl)-2,3,6-trioxohexahydro-1,3,5 triazine, N-isocyanatohexylaminocarbonyl-N,N′

-bis(isocyanatohexyl) urea, 4-(isocyanatomethyl)-1,8-octane diisocyanate and mixtures thereof.

4. The polyurethane according to claim 1, wherein the polyisocyanate is selected from the group consisting of aliphatic, cycloaliphatic, aromatic and heterocyclic isocyanates, dimers and trimers thereof and mixtures thereof.

5. The poly(ureaurethane) according to claim 1, wherein the polyisocyanate is present in an amount of about 1 equivalent and the water is present in an amount of about 0.05 to about 0.5 equivalents.

6. The poly(ureaurethane) according to claim 1, wherein the aliphatic polyol is selected from the group consisting of diols, triols, and mixtures thereof.

7. The poly(ureaurethane) according to claim 6, wherein the aliphatic polyol is a diol 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.

8. The poly(ureaurethane) according to claim 7, wherein the diol is selected from the group consisting of butanediol, pentanediol, cyclohexane dimethanol and mixtures thereof.

9. The poly(ureaurethane) according to claim 1, wherein the aliphatic polyol is a triol selected from the group consisting of glycerol, glycerin, tetramethylolmethane, trimethylolethane, trimethylolpropane, erythritol, pentaerythritol, dipentaerythritol, tripentaerythritol, alkoxylated derivatives thereof and mixtures thereof.

10. The poly(ureaurethane) according to claim 9, wherein the branched polyol is trimethylolpropane.

11. The poly(ureaurethane) according to claim 1, wherein the aliphatic polyol is present in an amount of about 0.1 to about 1 equivalents.

12. The poly(ureaurethane) according to claim 1, wherein the reaction product components are essentially free of polyester polyol

13. The poly(ureaurethane) according to claim 1, wherein the reaction product components are essentially free of polyether polyol.

14. The poly(ureaurethane) according to claim 1, wherein the reaction product components further comprise 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.

15. An article comprising the poly(ureaurethane) of claim 1.

16. The article according to claim 15, wherein the article is a molded article.

17. The article according to claim 15, wherein the article is selected from the group consisting of transparencies, optical articles, photochromic articles, ballistic resistant articles, and glazings.

18. A laminate comprising:

(a) at least one layer of the poly(ureaurethane) of claim 1;

and

(b) at least one layer of a substrate selected from the group consisting of paper, glass, ceramic, wood, masonry, textile, metal or organic polymeric material and combinations thereof.

19. A coating composition comprising the poly(ureaurethane) of claim 1.