Moisture curable silylated polymer compositions containing reactive modifiers

Patent metadata

Field	Value
Publication number	US-9714315-B2
Application number	US-201414327059-A
Country	US
Kind code	B2
Filing date	Jul 9, 2014
Priority date	May 1, 2009
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

A moisture-curable resin composition comprising (a) a moisture-curable polymer having at least one hydrolysable silyl group; (b) a reactive modifier; (c) a catalyst for catalyzing the reaction between the moisture-curable polymer (a) and reactive modifier (b) under curing conditions; and optionally, the composition can contain one or more conventional components, including pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, ultraviolet stabilizers, and combination thereof. The moisture-curable resin composition is useful in the production of adhesives including hot melt adhesives, primers, sealants and coatings.

First claim

What is claimed is:

1. A moisture-curable resin composition comprising:
(a) a moisture-curable polymer having at least one hydrolysable silyl group having the general Formula (3):
R 6 —[O—R 7 —Si(X 1 X 2 X 3 )] f   (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 polyols selected from the group consisting of hydroxyl-terminated polyalkylene oxides diol, hydroxyl-terminated polyalkylene oxides triol, polycaprolactone diol, polycaprolactone triol, hydroxyl terminated unsaturated rubber, and polyester made from saturated aliphatic, unsaturated and/or aromatic diacids and diols and/or triols;
each occurrence of R 7 is independently a divalent alkylene, alkenylene, arenylene, arylene or aralkylene group containing up to 12 carbon atoms;
each occurrence of X 1 is independently R 9 O—, wherein each R 9 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl groups, wherein each R 9 , 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 9 O— and R 10 wherein each R 9 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, arenyl, aryl, and aralkyl, wherein each R 9 , other than hydrogen, contains from 1 to 18 carbon atoms and, optionally, contains at least one oxygen or sulfur atom and each R 10 is independently an alkyl group containing from 1 to 6 carbon atoms; and
f is an integer wherein f is 1 to 6; and
(b) a reactive modifier having the general Formula (1):
G 1 [—R 1 SiR 2 a (OR 3 ) 3-a ] b   (Formula 1)

wherein:
G 1 is selected from the group consisting of a divalent and polyvalent monocyclic hydrocarbon group containing from 5 to 16 carbon atoms, a divalent and polyvalent cyclic heterocarbon group containing from 3 to 16 carbon atoms wherein the heteroatom are selected from the group consisting of oxygen, silicon and sulfur; and a divalent and polyvalent cyclic silicone group containing from 3 to 8 silicon atoms and from 3 to 8 oxygen atoms;
each occurrence of R 1 is independently selected from the group consisting of a covalent bond between the silicon atom and G 1 , a divalent hydrocarbon group containing from 1 to 18 carbon atoms;
each occurrence of R 2 is monovalent hydrocarbon containing from 1 to 12 carbon atoms;
each occurrence of R 3 is monovalent hydrocarbon containing from 1 to 12 carbon atoms;
each occurrence of a and b is independently an integer, wherein a is 0 to 2; and b is 2 to 6, with the provisos that,
(i) when R 1 is a chemical bond, then the silicon atom is covalently bonded to a carbon atom of G 1 ;
(ii) when R 1 contains a heteroatom, the silicon atom is bonded to a carbon atom of R 1 ;

and
(c) a catalyst for catalyzing the reaction between the moisture-curable polymer (a) and reactive modifier (b) under curing conditions selected from the group consisting of an organic dibutyltin, zirconium complex, aluminum chelate, titanic chelate, organic zinc, organic cobalt, organic iron, organic nickel, organobismuth, amine and mixtures of organometallic compounds and amine, and wherein component (a) is present in an amount of from 30 weight percent to 95 weight percent based upon the total weight of (a), (b) and (c); component (b) is present in an amount of from 5 weight percent to 70 weight percent based upon the total weight of (a), (b) and (c); and component (c) is present in an amount of from 0.05 weight percent to 5 weight percent based upon the total weight of (a), (b) and (c).

2. The moisture-curable composition of claim 1 , wherein the catalyst (c) is an organic dibutyltin, aluminum chelate, organic zinc, organobismuth and amine.

3. The moisture-curable resin composition of claim 2 , wherein the moisture-curable resin composition comprises from 50 weight percent to 90 weight percent based upon the total weight of components (a), (b) and (c) a moisture-curable polymer having at least one hydrolysable group (a), from 10 to 50 weight percent based upon the total weight of components (a), (b) and (c) a reactive modifier (b), and from 0.1 weight percent to 3 weight percent based upon the total weight of components (a), (b) and (c), a catalysts, wherein G 1 is a divalent or polyvalent cyclic hydrocarbon containing from 6 to 10 carbon atoms; each occurrence of R 1 and R 7 is independently an alkylene group of from 1 to 6 carbon atoms; each occurrence of R 2 and R 3 , is independently an alkyl group of from 1 to 4 carbon atoms; a is 0 or 1; b is 2 or 3; and f is 2.

4. The moisture-curable resin composition of claim 3 , wherein the moisture-curable resin composition comprises from 60 weight percent to 80 weight percent based upon the total weight of components (a), (b) and (c) a moisture-curable polymer having at least one hydrolysable group (a), from 20 to 40 weight percent based upon the total weight of components (a), (b) and (c) a reactive modifier (b), and from 0.5 weight percent to 2 weight percent based upon the total weight of components (a), (b) and (c), a catalysts, wherein G 1 is a divalent or polyvalent cyclic hydrocarbon derivable from cyclohexane, cyclooctane and cyclodecane; each occurrence of R 1 and R 7 is independently methylene, ethylene or propylene; each occurrence of R 2 and R 3 , is independently methyl or ethyl; a is 0; b is 3; and f is 2.

5. The moisture-curable composition of claim 2 , wherein the moisture-curable resin composition comprises 60 weight percent to 80 weight percent based upon the total weight of components (a), (b) and (c) a moisture-curable polymer having at least one hydrolysable group (a), from 20 to 40 weight percent based upon the total weight of components (a), (b) and (c) a reactive modifier (b), and from 0.5 weight percent to 2 weight percent based upon the total weight of components (a), (b) and (c), a catalysts, wherein G 1 is a divalent or polyvalent monocyclic hydrocarbon derivable from cyclohexane, cyclooctane and cyclodecane; each occurrence of R 1 and R 7 is independently methylene, ethylene or propylene; each occurrence of R 2 , R 3 , R 9 and R 10 is independently methyl or ethyl; a is 0 or 1; b is 2 or 3; and f is 2.

6. A cured moisture-curable resin composition made by curing the moisture-curable resin composition of claim 1 .

7. The cured moisture-curable resin composition of claim 6 , wherein the reactive modifier (b) is selected from the group consisting of 1,2,4-tris-[2-(trimethoxy-silanyl)-ethyl]-cyclohexane, 1,2,4-tris-[2-(dimethoxy-methyl-silanyl)-ethyl]-cyclohexane, 1,2,4-tris[2-(triethoxy-silanyl)-ethyl]-cyclohexane, 1,2,4-tris-[2-(tripropoxy-silanyl)-ethyl]-cyclohexane, 1,4-bis[2-(trimethoxy-silanyl)-ethyl]-2-vinyl-cyclohexane, 1,4-bis-[2-(dimethoxy-methyl-silanyl)-ethyl]-2-vinyl-cyclohexane, 1,4-bis-[2-(triethoxy-silanyl)-ethyl]-2-vinyl-cyclohexane, 1-(2-{2,5-bis-[2-(trimethoxy-silanyl)-ethyl]-cyclohexyl}-ethyl)-3-(2-{2,4-bis-[2-(trimethoxy-silanyl)-ethyl]-cyclohexyl)-ethyl)-1,1,3,3-tetramethyl-disiloxane, 1-(2-{2,5-bis-[2-(dimethoxy-methyl-silanyl)-ethyl)-cyclohexyl]-ethyl)-3-(2-(2,4-bis-[2-(dimethoxy-methyl-silanyl)-ethyl]-cyclohexyl}-ethyl)-1,1,3,3-tetramethyl-disiloxane, 1-(2-{2,5-bis-[2-(triethoxy-silanyl)-ethyl]-cyclohexyl}-ethyl)-3-(2-(2,4-bis-[2-(triethoxy-silanyl)-ethyl]-cyclohexyl}-ethyl)-1,1,3,3-tetramethyl-disiloxane, 2,5-bis-[2-(trimethoxy-silanyl)-ethyl]-bicyclo[2.2.1]heptane, 2,4,6,8-tetramethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocane, 2,4,6,8-tetrakis-[2-(triethoxy-silanyl)-ethyl]-2,4,6,8-tetramethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocane, 2,4,6-t

Assignees

• Momentive Performance Mat Inc

Inventors

• Huang Misty
• Cruse Richard W
• Falk Benjamin
• Pohl Eric
• Su Shiu-Chin
• Nesheiwat Jeries
• Ramdatt Philbert

Classifications

• C08G18/289

  containing silicon · CPC title

• C08G18/10 Primary

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

• C08G2/10

  Polymerisation of cyclic oligomers of formaldehyde · CPC title

• C08G18/837 Primary

  by silicon containing compounds · CPC title

• C08G18/718

  containing silicon · CPC title