Granted Patent B2

US 8,809,479 · App. 12/767,715 · Granted Aug 19, 2014

Abstract

Claims (57)

1. A moisture-curable resin composition comprising:

(a) a moisture-curable polymer having at least one hydrolysable silyl group wherein the polymer is represented by the general Formula (3):

wherein:

each occurrence of R 6 is independently a monovalent or polyvalent organic polymer fragment having a number average molecular weight of from 500 to 25,000 grams per mole and derived from a hydroxyl-terminated polypropylene oxide having a terminal ethylenic unsaturation of less than 0.02 milliequivalents per gram polyol and containing at least one urethane functional group;

each occurrence of R 7 is independently a divalent alkylene group containing from 1 to 6 carbon atoms;

each occurrence of A 1 is divalent oxygen (—O—);

each occurrence of A 2 is substituted nitrogen of the structure —NR 8 —, wherein R 8 is hydrogen;

each occurrence of X 1 is independently R 9 O—, wherein each R 9 is independently hydrogen or an alkyl group containing from 1 to 4 carbon atoms;

each occurrence of X 2 and X 3 is independently selected from the group consisting of R 9 O— and R 10 wherein each R 9 is independently hydrogen or an alkyl group containing from 1 to 4 carbon atoms and each R 10 is independently an alkyl group containing from 1 to 4 carbon atoms; and,

each occurrence of subscripts e and f is independently an integer wherein e is 1 and f is 1 to 6;

(b) a reactive modifier of the general Formula (2):

G 2 [-SiR 4 c (OR 5 ) 3-c ] d   (Formula 2)

wherein:

G 2 is selected from the group consisting of a monovalent or divalent linear hydrocarbon group containing from 3 to 16 carbon atoms;

each occurrence of R 4 is monovalent alkyl group containing from 1 to 4 carbon atoms;

each occurrence of R 5 is monovalent alkyl group containing from 1 to 4 carbon atoms;

each occurrence of c and d is independently an integer, wherein; c is 0 or 1; and d is 1 or 2 with the provisos that,

(i) when G 2 contains a heteroatom, the terminal atoms of G 2 are carbon atoms; and

(ii) when the silicon atom is attached to G 2 , the silicon atom is covalently bonded to a terminal carbon of G 2 ; and

(c) at least one catalyst which is a compound selected from the group consisting of organic dibutyltin, zirconium complex, aluminum chelate, titanic chelate, organic zinc, organic cobalt, organic iron, organic nickel, organobismuth and amine for catalyzing the reaction between the moisture-curable polymer (a) and reactive modifier (b) under moisture curing conditions; and

wherein component (b) is present in an amount of from 20 weight percent to 40 weight percent and component (c) is present in an amount of from 0.1 to 3 weight percent, based upon the total weight of components (a), (b) and (c).

2. The moisture-curable composition of claim 1 , wherein the catalyst (c) is a compound selected from the group consisting of aluminum chelate, titanic chelate, organic zinc, and organobismuth.

3. The moisture-curable resin composition of claim 1 , wherein the reactive modifier (b) is selected from the group consisting of trimethoxy-pentyl-silane, dimethoxy-methyl-pentyl-silane, triethoxy-hexyl-silane, trimethoxy-hexyl-silane, dimethoxy-methyl-hexyl-silane, triethoxy-hexyl-silane, trimethoxy-octyl-silane, dimethoxy-methyl-octyl-silane, triethoxy-octyl-silane, trimethoxy-hexadecyl-silane, dimethoxy-methyl-hexadecyl-silane, triethoxy-hexadecyl-silane, 1,6-bis-(trimethoxy-silanyl)-hexane, 1,6-bis-(dimethoxy-methyl-silanyl)-hexane, 1,6-bis-(triethoxy-silanyl)-hexane, 1,8-bis-(trimethoxy-silanyl)-octane, 1,8-bis-(dimethoxy-methyl-silanyl)-octane, 1,8-bis-(triethoxy-silanyl)-octane, 1-[2-(trimethoxy-silanyl)-ethyl]-3-[3-(trimethoxy-silanyl)-propyl]-1,1,3,3-tetramethyl-disiloxane, and combinations thereof.

4. The moisture-curable resin composition of claim 3 , wherein the reactive modifier (b) is triethoxy-octyl-silane.

5. The moisture-curable resin composition of claim 3 further comprising at least one additive selected from the group consisting of pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, UV stabilizers, and combinations thereof.

6. The moisture-curable resin composition of claim 1 , wherein

G 2 is a monovalent or divalent linear hydrocarbon containing from 6 to 12 carbon atoms; and f is 2.

7. The moisture-curable resin composition of claim 1 , wherein

G 2 is a monovalent hydrocarbon derivable from pentane, hexane, octane, decane and dodecane; each occurrence of R 7 is independently methylene, ethylene or propylene; each occurrence of R 4 , R 5 , R 9 and R 10 is independently methyl or ethyl c is 0; d is 1; and f is 2.

8. The moisture-curable resin composition of claim 1 additionally containing a thermoplastic polymer and a tackifier, wherein component (a) is present in an amount of from 1% to 25%, component (b) is present in an amount of from 0.5% to 10%, component (c) is present in an amount of from 0.5% to 2%, the thermoplastic polymer is present in an amount of from 25% to 80%, and the tackifier is present in an amount of from 25% to 75%, all percents are weight percent based on the total weight of components (a), (b), (c), the thermoplastic polymer and the tackifier.

9. The cured composition of claim 8 .

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

11. A hot melt composition containing the moisture-curable resin composition of claim 1 .

12. The moisture-curable resin composition of claim 1 further comprising at least one additive selected from the group consisting of pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, UV stabilizers, and combinations thereof.

13. A cured composition produced by contacting a moisture-curable composition with water, said moisture-curable composition comprising:

(a) a moisture-curable polymer having at least one hydrolysable silyl group wherein the polymer is represented by the general Formula (3):

wherein:

each occurrence of R 6 is independently a monovalent or polyvalent organic polymer fragment having a number average molecular weight of from 500 to 25,000 grams per mole and, optionally, urethane functional groups, derived from a hydroxyl-terminated polypropylene oxide having a terminal ethylenic unsaturation of less than 0.02 milliequivalents per gram polyol;

each occurrence of R 7 is independently a divalent alkylene group containing from 1 to 6 carbon atoms;

each occurrence of A 1 is divalent oxygen (—O—);

each occurrence of A 2 is substituted nitrogen of the structure —NR 8 —, wherein R 8 is hydrogen;

each occurrence of X 1 is independently R 9 O—, wherein each R 9 is independently hydrogen or an alkyl group containing from 1 to 4 carbon atoms;

each occurrence of X 2 and X 3 is independently selected from the group consisting of R 9 O— and R 10 wherein each R 9 is independently hydrogen or an alkyl group containing from 1 to 4 carbon atoms and each R 10 is independently an alkyl group containing from 1 to 4 carbon atoms; and,

each occurrence of subscripts e and f is independently an integer wherein e is 1 and f is 1 to 6;

(b) a reactive modifier of the general Formula (2):

G 2 [-SiR 4 c (OR 5 ) 3-c ] d   (Formula 2)

wherein:

G 2 is selected from the group consisting of a monovalent or divalent linear hydrocarbon group containing from 3 to 16 carbon atoms;

each occurrence of R 4 is monovalent alkyl group containing from 1 to 4 carbon atoms;

each occurrence of R 5 is monovalent alkyl group containing from 1 to 4 carbon atoms;

each occurrence of c and d is independently an integer, wherein c is 0 or 1; and d is 1 or 2 with the provisos that,

(i) when G 2 contains a heteroatom, the terminal atoms of G 2 are carbon atoms; and

(ii) when the silicon atom is attached to G 2 , the silicon atom is covalently bonded to a terminal carbon of G 2 ; and

(c) at least one catalyst which is a compound selected from the group consisting of organic dibutyltin, zirconium complex, aluminum chelate, titanic chelate, organic zinc, organic cobalt, organic iron, organic nickel, organobismuth and amine for catalyzing the reaction between the moisture-curable polymer (a) and reactive modifier (b) under moisture curing conditions; and

wherein component (b) is present in an amount of from 20 weight percent to 40 weight percent and component (c) is present in an amount of from 0.1 to 3 weight percent, based upon the total weight of components (a), (b) and (c).

14. The cured composition of claim 13 , wherein the catalyst (c) is a compound selected from the group consisting of aluminum chelate, titanic chelate, organic zinc, and organobismuth.

15. The cured composition of claim 13 , wherein the reactive modifier (b) is selected from the group consisting of trimethoxy-pentyl-silane, dimethoxy-methyl-pentyl-silane, triethoxy-hexyl-silane, trimethoxy-hexyl-silane, dimethoxy-methyl-hexyl-silane, triethoxy-hexyl-silane, trimethoxy-octyl-silane, dimethoxy-methyl-octyl-silane, triethoxy-octyl-silane, trimethoxy-hexadecyl-silane, dimethoxy-methyl-hexadecyl-silane, triethoxy-hexadecyl-silane, 1,6-bis-(trimethoxy-silanyl)-hexane, 1,6-bis-(dimethoxy-methyl-silanyl)-hexane, 1,6-bis-(triethoxy-silanyl)-hexane, 1,8-bis-(trimethoxy-silanyl)-octane, 1,8-bis-(dimethoxy-methyl-silanyl)-octane, 1,8-bis-(triethoxy-silanyl)-octane, 1-[2-(trimethoxy-silanyl)-ethyl]-3-[3-(trimethoxy-silanyl)-propyl]-1,1,3,3-tetramethyl-disiloxane, and combinations thereof.

Assignments (24)