Moisture curable silylated polymer compositions containing reactive modifiers

Patent metadata

Field	Value
Publication number	US-9932437-B2
Application number	US-201213608142-A
Country	US
Kind code	B2
Filing date	Sep 10, 2012
Priority date	May 1, 2009
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

Moisture-curable resin compositions 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 cured compositions produced by contacting such resin compositions with water are disclosed. 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 hydrolysable silyl groups and given by Formula (3):

wherein:
each occurrence of R 6 is independently a 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 optionally at least one urethane functional group;
each occurrence of R 7 is independently a divalent alkylene group containing from 1 to 3 carbon atoms;
each occurrence of A 1 is independently selected from a divalent oxygen (—O—), sulfur (—S—) or a substituted nitrogen of the structure (—) 2 NR 8 , wherein R 8 is alkyl, alkenyl, arenyl, aryl, aralkyl or —R 7 SiX 1 X 2 X 3 group containing from 1 to 18 carbon atoms or hydrogen, and with the proviso that when A 1 is oxygen or sulfur, then A 2 is (—) 2 NR 8 ;
each occurrence of A 2 is independently a substituted nitrogen of the structure (—) 2 NR 8 , wherein R 8 is an alkyl or aryl group containing from 1 to 6 carbon atoms or hydrogen;
each occurrence of X 1 is independently methoxy, ethoxy or propoxy;
each occurrence of X 2 and X 3 is methyl, methoxy, ethoxy or propoxy; and,
each occurrence of subscripts e and f is independently an integer wherein e is 1 and f is 2;
(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 linear alkyl group containing from 16 to 20 carbon atoms;
each occurrence of R 4 is methyl or ethyl;
each occurrence of R 5 is methyl or ethyl;
each occurrence of c and d is independently an integer, wherein c is 0 or 1; and d is 1; wherein, the silicon atom is covalently bonded to a terminal carbon of G 2 ; and
(c) a catalyst from the group consisting of organic dibutyltin, zirconium complex, aluminum chelate, titanic chelate, organic zinc, organic cobalt, organic iron, organic nickel, organobismuth, amine and combinations thereof for catalyzing the reaction between the moisture-curable polymer (a) and reactive modifier (b) under moisture curing conditions, wherein component (b) is in the amount of from 5 to 40 weight percent and component (c) is in the amount of from 0.05 to 5 weight percent, the weight percents are based on the total weights of components (a), (b) and (c).

2. The moisture-curable resin composition of claim 1 , wherein G 2 is a linear alkyl group containing 18 carbon atoms.

3. The moisture-curable resin composition of claim 1 , wherein G 2 is a linear alkyl group containing from 16 to 18 carbon atoms, R 4 and R 5 are methyl, c is 1 and d is 1.

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

5. The moisture-curable resin composition of claim 1 , wherein the reactive modifier (b) is selected from the group consisting of hexadecyltrimethoxysilane, hexadecylmethyldimethoxysilane, octadecyltrimethoxysilane, octadecylmethyldimethoxysilane, eicosyltrimethoxysilane, eicosylmethyldimethoxysilane, and combinations thereof.

6. The moisture-curable resin composition of claim 1 , wherein
component (a) is present in an amount of from 60 weight percent to 80 weight percent based upon the total weight of components (a), (b) and (c);
component (b) is present in an amount of from 20 weight percent to 40 weight percent based upon the total weight of components (a), (b) and (c); and
component (c) is present in an amount of from 0.5 weight percent to 2 weight percent based upon the total weight of components (a), (b) and (c), and wherein
G 2 is a monovalent linear alkyl group derivable from hexadecane, octadecane, or eicosane; 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;
R 8 is hydrogen; each occurrence of A 1 is independently oxygen; each occurrence of A 2 is —NR 8 —; c is 1; d is 1; e is 1; and f is 2.

7. The moisture-curable resin composition of claim 1 , wherein
component (a) is present in an amount of from 60 weight percent to 80 weight percent based upon the total weight of components (a), (b) and (c);
component (b) is present in an amount of from 20 weight percent to 40 weight percent based upon the total weight of components (a), (b) and (c); and
component (c) is presented in an amount of from 0.5 weight percent to 2 weight percent based upon the total weight of components (a), (b) and (c), and
G 2 is a monovalent linear hydrocarbon derivable from hexadecane, octadecane or eicosane, 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; R 8 is hydrogen; each occurrence of A 1 is independently oxygen (—O—); c is 1; d is 1; e 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. A moisture-curable sealant, coating, primer, or adhesive containing the moisture-curable resin composition of claim 1 .

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

11. 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.

12. A cured composition produced by contacting a moisture-curable composition with water, said moisture-curable composition comprising:
(a) a moisture-curable polymer having hydrolysable silyl groups and given by Formula (3):

wherein:
each occurrence of R 6 is independently a 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 optionally at least one urethane functional group;
each occurrence of R 7 is independently a divalent alkylene group containing from 1 to 3 carbon atoms;
each occurrence of A l is independently selected from a divalent oxygen (—O—), sulfur (—S—) or a substituted nitrogen of the structure (—) 2 NR 8 , wherein R 8 is alkyl, alkenyl, arenyl, aryl, aralkyl or —R 7 SiX 1 X 2 X 3 group containing from 1 to 18 carbon atoms or hydrogen, and with the proviso that when A 1 is oxygen or sulfur, then A 2 is (—) 2 NR 8 ;

Assignees

• Huang Misty
• Cruse Richard W
• Falk Benjamin
• Pohl Eric
• Su Shiu Chin
• Nesheiwat Jeries
• Ramdatt Philbert
• Lim Thomas Fay Oy
• Kumar Vikram
• Momentive Performance Mat Inc

Inventors

• Huang Misty
• Cruse Richard W
• Falk Benjamin
• Pohl Eric
• Su Shiu-Chin
• Nesheiwat Jeries
• Ramdatt Philbert
• Lim Thomas Fay-Oy
• Kumar Vikram

Classifications

• C08G2170/20

  Compositions for hot melt adhesives · CPC title

• C09J175/04

  Polyurethanes · CPC title

• C08G18/10

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

• C09D201/10

  containing hydrolysable silane groups · CPC title

• C09J201/10

  containing hydrolysable silane groups · CPC title