Granted Patent B2

US 8,859,674 · App. 13/077,077 · Granted Oct 14, 2014

Abstract

Claims (48)

1. A moisture-curable resin composition comprising:

(a) at least one moisture-curable polymer having at least one hydrolysable silyl group;

(b) at least one hydrocarbylalkoxysilane represented by the general Formula (II)

R 6 CH 2 CHSi(CH 3 ) c (OCH 3 ) 3-c   Formula (II)

wherein c is zero or 1, and R 6 is an alkyl or an alkenyl group of 2 to 18 carbon atoms;

(c) at least one silane adhesion promoter represented by the general Formula (III)

wherein d is 0, 1, or 2, and n is 2 to 6;

wherein

(i) the amount of said component (b) present in the moisture-curable resin composition is from about 5 to about 35 weight percent based upon the weight of said component (a);

(ii) the amount of said component (c) present in the moisture-curable resin composition is from about 1 to about 25 weight percent based upon the weight of said component (a);

(iii) the total amount of said component (b) and said component (c) present in the moisture-curable resin composition is from about 10 to about 45 weight percent based upon the weight of said component (a);

with the provisos that

(i) the moisture-curable resin composition is substantially free of hydroxyl-terminated dimethyl siloxane; and

(ii) the moisture-curable resin composition is substantially free of low molecular weight glycols having the Formula (V):

HO[(CR 7 2 ) m O] y H  (V)

wherein R 7 is hydrogen or an alkyl group of from 1 to 4 carbon atoms, m is an integer of from 2 to 6 and y is an integer from 1 to 4.

2. The moisture-curable resin composition of claim 1 , wherein said component (a) has the general Formula (I):

wherein

R 1 is independently a monovalent or polyvalent organic polymer fragment having a number average molecular weight of from 500 to 25,000 grams per mole (g/mol);

each occurrence of R 2 is independently a divalent hydrocarbylene group containing from 1 to 12 carbon atoms;

each occurrence of A 1 is independently selected from divalent oxygen (—O—), sulfur (—S—) or the structure (−) n NR 3 , wherein R 3 is hydrogen, alkyl, alkenyl, arenyl, aryl, aralkyl, alkyl containing at least one ester functional group or —R 2 SiX 1 X 2 X 3 group, wherein each R 3 , other than hydrogen, contains from 1 to 18 carbon atoms, and with the provisos that when A′ is oxygen or sulfur, then A 2 is (−) 2 NR 3 and when a is 0, then A 1 is oxygen;

each occurrence of A 2 is independently selected from divalent oxygen (—O—), sulfur (—S—) or the structure (−) n NR 3 , wherein R 3 is hydrogen, alkyl, alkenyl, arenyl, aryl, aralkyl, alkyl containing at least one ester functional group or —R 2 SiX 1 X 2 X 3 group, wherein each R 3 , other than hydrogen, contains from 1 to 18 carbon atoms, and with the proviso that when A 2 is oxygen or sulfur, then A 1 is (−) 2 NR 3 ;

each occurrence of X 1 is independently R 4 O—, wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl groups, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom;

each occurrence of X 2 and X 3 is independently selected from the group consisting of R 4 O— and R 5 wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom and each R 5 is independently an alkyl group containing from 1 to 6 carbon atoms; and,

each occurrence of subscripts a and b is independently an integer wherein a is 0 or 1 and b is 1 to 6.

3. A moisture-curable resin composition of claim 2 , wherein said component (a) is derived from a polyol reactant or a combination of polyol reactants and optionally contain at least one organic functional group selected from the group consisting of urethane, thiourethane, urea, biuret, ester, thioester, ether, thioether, and amide.

4. The moisture-curable resin composition of claim 3 , wherein the polyol reactant has a number average molecular weight of from 300 to 24,000 grams per mole (g/mol).

5. The moisture-curable resin composition of claim 2 , wherein R 1 is a polymer fragment having a number average molecular weight from 500 to 25,000 grams per mole, R 2 is an alkylene of from 1 to 3 carbon atoms; A 1 is oxygen or the structure (−) 2 NR 3 , wherein R 3 is hydrogen; A 2 is the structure (−) 2 NR 3 , wherein R 3 is hydrogen, alkyl or aryl, wherein each R 3 , other than hydrogen, contains 1 to 10 carbon atoms; X 1 and X 2 are methoxy, ethoxy or propoxy; and X 3 is methyl, methoxy, ethoxy or propoxy.

6. The moisture-curable resin composition of claim 2 , wherein the moisture-curable polymer (a) is prepared by reacting a polyol or a combination of polyols with a hydrolysable silane containing an isocyanate group, wherein the molar ratio of —NCO of the hydrolysable silane containing an isocyanate group to —OH of the polyol or combination of polyols is from 0.3 to 1.2.

7. The moisture-curable resin composition of claim 6 , wherein the hydrolysable silane is selected from the group consisting of isocyanatomethyltrimethoxysilane, isocyanatomethylmethydimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatoisopropyltrimethoxysilane, 4-isocyanatobutyltrimethoxysilane, 2-isocyanato-1,1-dimethylethyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-isocyanatoisopropyltriethoxysilane, 4-isocyanatobutyltriethoxysilane, 2-isocyanato-1,1-dimethylethyltriethoxysilane, 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanatoisopropyldimethylmethoxysilane, 4-isocyanatobutylphenyldimethoxysilane, 2-(4-isocyanatophenyl)ethylmethyldimethoxysilane, and mixtures thereof.

8. The moisture-curable resin composition of claim 1 , wherein said component (a) is represented by generic Formula (VII):

wherein R 1 is an organic polymer fragment containing at least a urethane group as a result of the reaction of a polyol with an isocyanate group, and has a number average molecular weight of 4,000 to 18,000 grams per mole, each occurrence of R 2 is independently a divalent hydrocarbylene group containing from 1 to 12 carbon atoms, each occurrence of X 1 is independently R 4 O—, wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl groups, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom; each occurrence of X 2 and X 3 is independently selected from the group consisting of R 4 O— and R 5 wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom and each R 5 is independently an alkyl group containing from 1 to 6 carbon atoms, and b is 2.

9. The moisture-curable resin composition of claim 8 , wherein component (a) is a silylated polyurethane prepared by a process comprising: (A) reacting a polyol component with a diisocyanate component at a stoichiometric excess of the polyol component to the diisocyanate component to form a hydroxyl-terminated polyurethane; and (B) reacting the hydroxyl-terminated polyurethane with one or more isocyanate silanes of the formula OCN—R 2 —SiX 1 X 2 X 3 , wherein each occurrence of R 2 is independently a divalent hydrocarbylene group containing from 1 to 12 carbon atoms, each occurrence of X 1 is independently R 4 O—, wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl groups, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom; and each occurrence of X 2 and X 3 is independently selected from the group consisting of R 4 O— and R 5 wherein each R 4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl, wherein each R 4 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom and each R 5 is independently an alkyl group containing from 1 to 6 carbon atoms.

10. The moisture-curable resin composition of claim 9 wherein the polyol is selected from the group consisting of hydroxyl-terminated polypropylene oxide, hydroxyl-terminated polyethylene oxide, hydroxyl-terminated polybutylene oxide, and combinations thereof.

11. The moisture-curable resin composition of claim 10 wherein the diisocyanate is selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, a mixture of 2,4- and 2,6-toluene diisocyanate isomers, 4,4′ diphenyl-methanediisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, liquid diphenylmethane-diisocyanates containing a mixture of 2,4- and 4,4′ isomers, and combinations thereof.

12. The moisture-curable resin composition of claim 1 , wherein said component (b) is selected from the group consisting of butyl-trimethoxy-silane, sec-butyl-tiimethoxy-silane, hexyl-trimethoxy-silane, hexyl-dimethoxy-methyl-silane, hex-5-enyl-trimethoxy-silane, hex-5-enyl-dimethoxy-methyl-silane, trimethoxy-octyl-silane, dimethoxy-methyl-octyl-silane, decyl-trimethoxy-silane, decyl-dimethoxy-methyl-silane, dodecyl-trimethoxy-silane, dodecyl-dimethoxy-methyl-silane, hexadecyl-trimethoxy-silane, hexadecyl-dimethoxy-methyl-silane, octadecyl-trimethoxy-silane, dimethoxy-methyl-octadecyl-silane, dimethoxy-methyl-eicosyl-silane, trimethoxy-methyl-eicosyl-silane, and combinations thereof.

13. The moisture-curable resin composition of claim 11 , wherein said component (c) is selected from the group consisting of trimethoxy-(3-oxiranylmethoxy-propyl)-silane, dimethoxy-methyl-(3-oxiranylmethoxy-propyl)-silane, and combinations thereof.

14. The moisture-curable composition of claim 1 wherein the composition is substantially free of aminofunctional alkoxysilanes.

15. The moisture-curable composition of claim 1 further comprising at least one additive selected from the group consisting of a catalyst for catalyzing the reaction between said component (a) with water under curing conditions, a filler, a plasticizer, and combinations thereof.

16. The moisture-curable composition of claim 15 further comprising at least one additive selected group the group consisting of pigments, thixotropes, waxes, anti-sagging agents, stabilizers, viscosity modifiers, and combinations thereof.

17. A cured composition produced by contacting the composition of claim 1 with water.

18. A moisture-curable sealant, adhesive or coating containing the moisture-curable resin composition of claim 1 .

19. A method for treating a substrate comprising:

(a) providing a composition of claim 1 ;

(b) applying said composition to a surface of the substrate.

20. The method of claim 19 wherein the substrate is concrete.

21. An article comprising the cured moisture-curable resin composition of claim 1 and an unprimed concrete substrate to which the cured moisture-curable resin composition is bonded.

22. The article of claim 21 wherein the article has a peel strengths of from 1.80 to 8.90 N/mm (10 to 50 lb/in) after exposure to water for seven days when the article is tested according to ASTM C-794-06.

Assignments (22)