Siloxane organic hybrid materials providing flexibility to epoxy-based coating compositions

Patent metadata

Field	Value
Publication number	US-9273225-B2
Application number	US-201213611791-A
Country	US
Kind code	B2
Filing date	Sep 12, 2012
Priority date	Sep 12, 2012
Publication date	Mar 1, 2016
Grant date	Mar 1, 2016

Abstract

Disclosed herein are epoxy-based compositions that include a polysiloxane flexibilizer and amino-functional alkoxysilane, which provides flexibility, hardness and gloss to such compositions and that are useful as coatings, adhesives, sealants and composites. Also disclosed are cured compositions and substrates coated with such epoxy-based compositions.

First claim

What is claimed is:

1. An epoxy-based composition comprising:
(a) an epoxide resin having at least one 1,2-epoxy group per molecule with an epoxide equivalent weight in the range of from 100 to 2000;
(b) an amino-functional alkoxysilane;
(c) a flexibilizer having the general Formula (I):

wherein:
each occurrence of R 1 is independently an alkyl group having from 1 to 6 carbon atoms, a phenyl group or an arenyl group having 7 to 12 carbon atoms;
each occurrence of R 2 is independently an alkyl group having from 1 to 6 carbon atoms;
each occurrence of R 3 is independently a phenyl group or an arenyl group having 7 to 12 carbon atoms;
each X 1 is independently a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms and at least one ether or ester functional group;
each X 2 is independently a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms and at least one ether or ester functional group, or a group with the Formula (II):

each occurrence of the subscripts a, m, n, p, x and y is independently an integer wherein a is 1 to 3; m is 0 to 500, n is 1 to 500, p is 0 to 10, x is 0 to 50, and y is 0 to 50 with the provisos that
(i) the molar ratio of m to n is from 0 to 15, and
(ii) the molar ratio of p to n is from 0 to 1; and
(iii) the flexibilizer (c) has a silanol content or a SiX 1 content of from 2 to 15 mole %, based upon the total number of silicon atoms; and
(d) at least one curing catalyst.

2. The epoxy-based composition of claim 1 wherein the epoxy resin (a) has the general Formula (III):

wherein:
each occurrence of R 4 is independently hydrogen, an alkyl group of from 1 to 8 carbon atoms, a phenyl group or an aralkyl or arenyl group of from 7 to 12 carbon atoms;
each occurrence of R 5 is a divalent organic group of from 1 to 12 carbon atoms or a chemical bond;
G 1 is a divalent or polyvalent organic group containing from 1 to 1,000 carbon atoms; and b is 2 to 8.

3. The epoxy-based composition of claim 2 wherein R 4 is hydrogen or methyl; R 5 is a chemical bond, or a —C(═O)—, —C(═O)O—, —O—, —C c H 2c —, —C c H 2c O—, —C c H 2c OC(═O)—, —C c H 2c C(═O)—,
—C c H 2c C(═O)O— or —(C c H 2c O—) d group, wherein each occurrence of c and d is independently an integer where c is from 1 to 8 and d is from is 1 to 6; and G 1 is a divalent or polyvalent hydrocarbon group containing from 1 to 700 carbon atoms derived from an linear or branched alkylcycloalkyl, alkenyl aralkyl, aryl, arenyl or a group derived from a heterocarbon containing from 1 to 700 carbon atoms at least one functional group selected from the group consisting of —O—, N═, —OH, —S—, —C(═O)—, —C(═O)O—, —C(═O)OH, and —C(═O)S—, and b is 2 to 5.

4. The epoxy-based composition of claim 2 wherein G 1 is selected from the group consisting of hydrogenated cyclohexane dimethyl, hydrogenated Bisphenol A, bisphenol A,

where z is 0 to 12;

where z is 0 to 1.2:

where z is 0 to 12;

where z is 0 to 10;

5. The epoxy-based composition of claim 1 wherein the epoxy resin (a) is selected from the group consisting of 2-{4-[1-methyl-1-(4-oxiranylmethoxy-cyclohexyl)-ethyl]-cyclohexyloxymethyl}-oxirane, diglycidyl ether of bisphenol A, hydrogenated diglycidyl ether of bisphenol A, epoxy phenol novolac resins, epoxy cresol novolac resins, diglycidyl ether of bisphenol F, tetradlycidyl ether of tetrakis(4-hydroxyphenyl)ethane, triglycidyl-p-aminophenol, N,N,N′,N′-tetraglycidyl-4,4′-diaminodiphenylmethane, triglycidyl isocyanurate, and diglycidyl ether of hexahydrophthalic acid.

6. The epoxy-based composition of claim 1 wherein epoxy resin (a) is present in the composition in an amount ranging from 10 to 80 percent by weight.

7. The epoxy-based composition of claim 1 , wherein the amino-functional alkoxysilane has the general Formulae (IV) or (V):

wherein:
each R 6 , R 7 and R 9 is independently a hydrogen or a monovalent hydrocarbon group containing from 1 to 12 carbon atoms selected from the group consisting of straight chain alkyl, branched chain alkyl, cycloalkyl, aralkyl, alkenyl, aryl and arenyl;
each R 8 and R 10 is independently a divalent hydrocarbon group containing from 1 to 12 carbon atoms selected from the group consisting of straight chain alkylene, branched chain alkylene, cyloalkylene, aralkylene, alkenylene, arylene or arenylene;
R 11 is a divalent hydrocarbon group containing from 1 to 12 carbon atoms selected from the group consisting of straight chain alkylene, branched chain alkylene, cyloalkylene, aralkylene, alkenylene, arylene or arenylene or a divalent organic group containing from 1 to 12 carbon atoms and at least one functional group selected from hydroxyl group, other group and ester group;
X 2 is —OR 12 , wherein R 12 is a hydrogen, a monovalent hydrocarbon group containing from 1 to 12 carbon atoms selected from the group consisting of straight chain alkyl, branched chain alkyl, cycloalkyl, aralkyl, alkenyl, aryl and arenyl or a monovalent organic group containing from 1 to 12 carbon atoms and at least one functional group selected from hydroxyl group, ether group and ester group;
each X 3 and X 4 is independently X 2 , a methyl or a phenyl group; and
the subscript c is an integer wherein c is 1 to 3.

8. The epoxy-based composition of claim 7 wherein the amino-functional alkoxysilane (b) is selected from the group consisting of (methoxy-dimethyl-silanyl)-methylamine, (dimethoxy-methyl-silanyl)-methylamine, (trimethoxy-silanyl)-methylamine, 2-(methoxy-dimethyl-silanyl)-ethylamine, 3-(dimethoxy-methyl-silanyl)-ethylamine, 2-(trimethoxy-silanyl)-ethylamine, 3-(methoxy-dimethyl-silanyl)-propylamine, 3-(dimethoxy-methyl-silanyl)-propylamine, 3-(trimethoxy-silanyl)-propylamine, (ethoxy-dimethyl-silanyl)-methylamine, (diethoxy-methyl-silanyl)-methylamine, (triethoxy-silanyl)-methylamine, 2-(ethoxy-dimethyl-silanyl)-ethylamine, 3-(diethoxy-methyl-silanyl)-ethylamine, 2-(triethoxy-silanyl)-ethylamine, 3-(ethoxy-dimethyl-silanyl)-propylamine, 3-(diethoxy-methyl-silanyl)-propylamine, 3-(triethoxy-silanyl)-propylamine, 3-(dipropoxy-methyl-silanyl)-propylamine, 3-(tripropoxy-silanyl)-propylamine, 3-(2-methyl-[1,3,2]dioxasilolan-2-yl)-propylamine, 3-(2-ethoxy-[1,3,2]dioxasilolan-2-yl)-propylamine, 3-(2-ethoxy-[1,3,2]dioxasilinan-2-yl)-propylamine, 3-(2-ethoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-propylamine, 3-[2-(3-amino-propyl)-5-methyl-[1,3,2]dioxasilinan-2-yloxy]-2-methyl-propan-1-ol, 3-(2-ethoxy-4,4,6-trimethyl-[1,3,2]dioxasilinan-2-yl)-propylamine, [3-(2-ethoxy-5-methyl-[1,3,2]dioxasilinan-2-yl)-2-methyl-propyl]-ethyl-amine, [3-(dimethoxy-

Assignees

• Geismann Christian
• Kumar Vikram
• Kondos Constantine
• Momentive Performance Mat Inc

Inventors

• Geismann Christian
• Kumar Vikram
• Kondos Constantine

Classifications

• C08G77/80

  Siloxanes having aromatic substituents, e.g. phenyl side groups · CPC title

• C08G77/16

  to hydroxy groups · CPC title

• C09D163/00 Primary

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title