Moisture-curable silylated resin derived from polycarbonate diol and coating, sealant and adhesive compositions containing same

Patent metadata

Field	Value
Publication number	US-11945899-B2
Application number	US-201916707061-A
Country	US
Kind code	B2
Filing date	Dec 9, 2019
Priority date	Mar 10, 2016
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

A moisture-curable silylated resin is derived from a copolycarbonate diol prepared from diol(s) of specific types.

First claim

What is claimed is:

1. A coating, sealant or adhesive composition containing a moisture-curable silylated resin, the moisture-curable silylated resin obtained by a process comprising reacting a silylating agent with at least one of:
a hydroxyl—terminated polyurethane (VI) derived from the reaction of an organic polyisocyanate and a polycarbonate diol (V); and,
an isocyanate—terminated polyurethane (VII) derived from the reaction of an organic polyisocyanate and a polycarbonate diol (V), and
wherein the polycarbonate diol (V) is obtained from the reaction of carbonylating agent and a diol of which at least 80 mole percent is diol selected from the group consisting of:
(i) a mixture of at least two different acyclic straight chain aliphatic diols each diol possessing up to 20 carbon atoms,
(ii) at least one acyclic branched chain diol possessing up to 20 carbon atoms, and

(iii) a mixture of at least one acyclic straight chain aliphatic diol possessing up to 20 carbon atoms and at least one acyclic branched chain aliphatic diol possessing up to 20 carbon atoms;
and wherein the hydroxyl—terminated polyurethane (VI) and the isocyanate—terminated polyurethane (VII) are derived from a mixture of polyisocyanates in which at least one polyisocyanate is an organic polyisocyanate containing two isocyanate groups and at least one other polyisocyanate is an organic polyisocyanate containing three isocyanate groups;
and wherein the moisture-curable silylated resin is combined with ingredients and formulated to result in a coating, sealant or adhesive composition.

2. The coating, sealant or adhesive composition of claim 1 , wherein the molar ratio of organic polyisocyanate containing two isocyanate groups and organic polyisocyanate containing three isocyanate groups is from 10:1 to 1:10.

3. The coating, sealant or adhesive composition of claim 1 , wherein the silylating agent that is reacted with the hydroxyl-terminated polyurethane (VI) is an isocyanatosilane having the general formula (IX):

wherein each R 1 is independently an alkyl group of from 1 to 6 carbon atoms, each R 2 is independently an alkyl group of from 1 to 4 carbon atoms or phenyl group, R 3 is a divalent alkylene group of from 1 to 12 carbon atoms, and a is an integer of from 1 to 3.

4. The coating, sealant or adhesive composition of claim 3 , wherein the isocyanatosilane is selected from the group consisting of 1-isocyanatomethyltrimethoxysilane, 2-isocyanatoethyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 1-isocyanatomethyltriethoxysilane, 2-isocyanatoethyltriethoxysilane, 3-isocyanatopropyltriethoxysilane, 1-isocyanatomethylmethyldimethoxysilane, 3-isocyanatopropylmethyldimethoxysilane, 1-isocyantomethylmethyldiethoxysilane, 3-isocyanatopropylmethyldiethoxysilane and mixtures thereof.

5. The coating, sealant or adhesive composition of claim 1 , wherein the silylating agent that is reacted with the isocyanate-terminated polyurethane (VII) is an aminosilane having the general formula (X):

wherein each R 1 is independently an alkyl group of from 1 to 6 carbon atoms, each R 2 is independently an alkyl group of from 1 to 4 carbon atoms or phenyl group, R 3 is a divalent alkylene group of from 1 to 12 carbon atoms, R 4 is an alkyl group of from 1 to 12 carbon atoms, phenyl group, hydrogen or —R 3 SiR 2 3-a (OR 1 ) a group and a is an integer of from 1 to 3.

6. The coating, sealant or adhesive composition of claim 5 , wherein the aminosilane is selected from the group consisting 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, 4-amino-3,3-dimethylbutyldimethoxymethylsilane, N-methylaminoisobutyltrimethoxysilane, N-ethylaminoisobutyltrimethoxysilane, N-ethyl-3-amino-2-methylpropyldiethoxymethylsilane, N-ethyl-3-amino-2-methylpropyltriethoxy silane, N-ethyl-3-amino-2-methylpropylmethyldimethoxysilane, N-butyl-3-aminopropyltrimethoxysilane, N-butyl-3-amino-2-methylpropyltrimethoxysilane, N-ethyl-4-amino-3,3-dimethylbutyldimethoxymethylsilane and N-ethyl-4-amino-3,3-dimethylbutyltrimethoxysilane, N,N-bis-(3-trimethoxysilylpropyl) amine and combinations thereof.

7. The coating, sealant or adhesive composition of claim 6 , wherein the aminosilane is N-ethylaminoisobutyltrimethoxysilane, N-ethyl-4-amino-3,3-dimethylbutyltrimethoxysilane, N-butyl-3-aminopropyltrimethoxysilane or a combination thereof.

8. The coating, sealant or adhesive composition of claim 1 possessing at least one of a number average molecular weight of from 1500 to 10,000, a crystalline content as measured by differential scanning colorimetry of not greater than 1 weight percent crystallinity, based on the total weight of the moisture-curable silylated resin (1), or a viscosity 0.05 to 50 Pascal·second.

9. A substantially water-free coating, sealant or adhesive composition comprising the moisture-curable silylated resin of claim 1 , wherein at least one of the ingredients is selected from the group consisting of organoalkoxysilanes, silicone hardcoats, metal particulates, metal oxide particulates, pigments, curing catalysts, leveling agents, antioxidants, UV stabilizers, dyes, fillers, adhesion promoters and solvents.

10. The substantially water-free coating, sealant or adhesive composition of claim 9 , wherein the composition is an adhesive.

11. The coating, sealant or adhesive composition containing the moisture-curable silylated resin of claim 1 , wherein the polycarbonate diol (V) is obtained from the reaction of carbonylating agent and diol mixture (ii), wherein at least one of the diols possesses an even number of carbon atoms and at least one other diol possesses an odd number of carbon atoms.

Assignees

• Momentive Performance Mat Inc

Inventors

• Kondos Constantine
• Soad Nayeem
• Huang Misty
• Lacroix Christine
• Kumar Vikram

Classifications

• C08G18/289 Primary

  containing silicon · CPC title

• C08G18/10

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

• C08G18/12

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

• C08G18/3206

  aliphatic · CPC title

• C08G18/44

  Polycarbonates · CPC title