Fast cure aspartate polysiloxane hybrid coating

Patent metadata

Field	Value
Publication number	US-9957417-B2
Application number	US-201514749989-A
Country	US
Kind code	B2
Filing date	Jun 25, 2015
Priority date	Mar 14, 2013
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The present invention provides a hybrid two component coating composition comprising as component I, (A) an N-alkoxysilylalkyl-aspartic acid ester, (B) a polysiloxane having a molecular weight in the range of from about 400 to 10,000, and optionally (C) at least one hydrolyzable silane; and as component II, (D) a polyisocyanate having an average NCO functionality of 2.5 to 5.5 and an isocyanate content, based on solids, of 9 to 50 wt % and containing aliphatic polyisocyanates; and (E) a catalyst. Methods of making and applying the hybrid coating composition are also provided.

First claim

What is claimed is:

1. A hybrid coating composition containing:
(I) a first Component comprising (A) an N-alkoxysilylalkyl-aspartic acid ester, (B) a polysiloxane having a molecular weight in the range of from about 400 to 10,000, corresponding to the formula:

wherein R 1 and R 6 are each independently selected from the group comprising hydroxyl, alkyl, aryl and alkoxy radicals having up to six carbon atoms, and each R 2 is independently selected from the group comprising hydrogen, alkyl and aryl radicals having up to six carbons, and n is selected so that the molecular weight for the polysiloxane is in the range of from about 400 to 10,000 and optionally (C) at least one hydrolyzable silane; and

(II) a second Component comprising (D) a polyisocyanate having an average NCO functionality of 2.0 to 5.5 and an isocyanate content, based on solids, of 2 to 50 wt % and containing aliphatic polyisocyanates; and (E) a catalyst.

2. The hybrid coating composition of claim 1 , wherein the N-alkoxysilylalkyl-aspartic acid ester (A) is prepared by the reaction of
(i) equimolar quantities of amino-alkyl alkoxysilanes corresponding to formula (I)

in which X, Y and Z represent identical or different organic groups which are inert with respect to isocyanate groups at a temperature below 100° C., provided that at least one of these groups is an alkoxy group, and n represents an integer of from 2 to 4, and
(ii) a maleic or fumaric acid ester.

3. The hybrid coating composition of claim 1 , wherein the N-alkoxysilylalkyl-aspartic acid ester (A) is selected from the group comprising N-(3-Trimethoxysilylpropyl)-aspartic acid dimethyl ester, N-(3-Trimethoxysilylpropyl)-aspartic acid diethyl ester, N-(3-Trimethoxysilylpropyl)-aspartic acid di-n-butyl ester, N-(3-Triethoxysilylpropyl)-aspartic acid dimethyl ester, N-(3-Triethoxysilylpropyl)-aspartic acid diethyl ester, and N-(3-Triethoxysilylpropyl)-aspartic acid di-n-butyl ester.

4. The hybrid coating composition of claim 1 , wherein R 1 and R 2 are methyl and R 6 is phenyl.

5. The hybrid coating composition of claim 1 , wherein the at least one hydrolyzable silane (C) corresponds to formula (III)
QSi(OX) 3   (III),

wherein X represents C 1 to C 4 alkyl and Q represents C 1 to C 8 alkyl, phenyl, methoxy, or ethoxy, and/or a hydrolyzate/condensate obtained therefrom.

6. The hybrid coating composition of claim 1 , wherein the at least one hydrolyzable silane (C) comprises methyltrimethoxysilane or a hydrolyzate/condensate obtained therefrom.

7. The hybrid coating composition of claim 1 , wherein the polyisocyanate (D) has an average NCO functionality of 3.0 and 4.5.

8. The hybrid coating composition of claim 1 , wherein the polyisocyanate (D) has an isocyanate content, based on solids, of 10 to 30 wt %.

9. The hybrid coating composition of claim 1 , wherein the polyisocyanate (D) has a content of monomeric diisocyanates of less than 2 wt %.

10. The hybrid coating composition of claim 1 , wherein the polyisocyanate (D) is selected from the group consisting of 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate, 1-isocyanato-2-isocyanatomethyl cyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)-methane, 2,4′-dicyclohexyl-methane diisocyanate, 1,3- and 1,4-bis-(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)-methane, α,α,α′,α′-tetramethyl-1,3-diisocyanate, α,α,α′,α′-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotoluylene diisocyanate, 2,6-hexahydrotoluylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-toluylene diisocyanate, 2,6-toluylene diisocyanate, 2,4-diphenyl-methane diisocyanate, 4,4′-diphenyl-methane diisocyanate, 1,5-diisocyanato naphthalene and mixtures thereof.

11. The hybrid coating composition of claim 1 , wherein at least 0.9 amine equivalents of the N-alkoxysilylalkyl-aspartic acid ester (A) are present for each NCO equivalent of polyisocyanate (D).

12. The hybrid coating composition of claim 1 , wherein the catalyst (E) is an amidine compound which has amidino functional group, —HN═CNH 2 , or an organotin compound.

13. The hybrid coating composition of claim 1 , wherein the catalyst (E) is 1,5-Diazobicyclo[4.3.0]non-5-en or dibutyltin dilaurate.

14. The hybrid coating composition of claim 1 , further comprising in Component (I) one or more materials selected from the group consisting of leveling agents, wetting agents, moisture scavengers, flow control agents, anti-skinning agents, antifoaming agents, fillers, adhesion promoters, viscosity regulators, plasticizers, pigments, dyes, UV absorbers, thermal stabilizers, antioxidants, and mixtures thereof.

15. The hybrid coating composition of claim 1 , further comprising a moisture scavenger which is an alkali metal aluminosilicate having the chemical formula (M x [(AIO 2 ) x (SiO 2 ) y ].(H 2 O) z , wherein M is a metal.

16. A substrate coated with a hybrid coating composition containing:
(I) a first Component comprising (A) an N-alkoxysilylalkyl-aspartic acid ester, (B) a polysiloxane having a molecular weight in the range of from about 400 to 10,000 corresponding to the formula:

wherein R 1 and R 6 are each independently selected from the group comprising hydroxyl, alkyl, aryl and alkoxy radicals having up to six carbon atoms, and each R 2 is independently selected from the group comprising hydrogen, alkyl and aryl radicals having up to six carbons, and n is selected so that the molecular weight for the polysiloxane is in the range of from about 400 to 10,000, and optionally (C) at least one hydrolyzable silane; and

(II) a second Component comprising (D) a polyisocyanate having an average NCO functionality of 2.0 to 5.5 and an isocyanate content, based on solids, of 2 to 50 wt % and containing aliphatic polyisocyanates; and (E) a catalyst.

17. The substrate of claim 16 , wherein the substrate is comprised of metal, natural and/or synthetic stone, ceramic, glass, brick, cement, concrete, cinderblock, wood and composites and laminates thereof; wallboard, drywall, cement board, plastic, paper, PVC, styrofoam, plastic composites, acrylic composites, polyurethane composites, polyester composites, asphalt, fiberglass, soil, or gravel.

18. A method of coating a substrate, the method comprising the step of pre-mixing and applying Components I and II of a hybrid coating composition to a substrate, wherein the hybrid coating composition contains:
(I) a first Component comprising (A) an N-alkoxysilylalkyl-aspartic acid ester, (B) a polysiloxane having a molecular weight in the range of from about 400 to 10,000 corresponding to the formula:

wherein R 1 and R 6 are each independently selected from the group comprising hydroxyl, alkyl, aryl and alkoxy radicals having up to six carbon atoms, and each R 2 is independently selected from the group comprising hydrogen, alkyl and ar

Assignees

• Bayer Materialscience Llc
• Covestro Llc

Inventors

• Olson Ahren

Classifications

• C09D183/04 Primary

  Polysiloxanes · CPC title

• C08G18/3821

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• Y10T428/31551

  Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C09D183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title