# US 10,370,572 B2 · Moisture-curable hot melt silicone adhesive compositions including an alkoxy-functional siloxane reactive resin

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- Number: US 10,370,572 B2
- Document ID: US10370572B2
- Status: Granted
- Kind: B2
- Application number: 14/766,773
- Filed: 2014-02-10
- Published: 2015-12-31
- Granted: 2019-08-06
- Earliest claimed: 2013-02-11
- Assignees: Dow Silicones Corporation
- Applicants: Dow Silicones Corporation
- Inventors: Thomas Bekemeier; Adrienne Bowman; Glenn Gordon; Roger Romain; James Tonge; Afrooz Zarisfi
- Web page: https://patentgrep.com/patent/US10370572B2

## CPC

- C09J 183/06: containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence)
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 37/12: characterised by using adhesives
- C08G 77/18: to alkoxy or aryloxy groups
- C08K 5/5419: containing at least one Si—C bond
- C08K 5/57: Organo-tin compounds
- C08L 83/00: Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C09J 183/04: Polysiloxanes
- C08G 77/12: containing silicon bound to hydrogen
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G 77/70: {Siloxanes defined by use of the MDTQ nomenclature}
- C09J 2483/003: in the primer coating
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A moisture-curable silicone adhesive composition is provided that comprises (A) a reactive resin, (B) a reactive polymer, (C) a moisture cure catalyst, and (D) a crosslinker resin. The reactive resin (A) comprises the reaction product of a reaction of an alkenyl-functional siloxane resin comprising R3SiO1/2 units and SiO4/2 units and an alkoxysilane-functional organosiloxane compound having at least one silicon-bonded hydrogen atom in the presence of a hydrosilylation catalyst. The reactive polymer (B) comprises the reaction product of a reaction of an alkoxysilane-functional organosiloxane compound having at least one silicon-bonded hydrogen atom and a polyorganosiloxane having an average, per molecule, of at least 2 aliphatically unsaturated organic groups in the presence of a hydrosilylation catalyst.

## Claims

### Claim 1

A moisture-curable hot melt silicone adhesive composition comprising:
(A) a reactive resin comprising a hydrosilylation reaction product of a reaction of:
an alkenyl-functional siloxane resin comprising R3SiO1/2 units and SiO4/2 units, wherein each R is independently a monovalent hydrocarbon radical having 1 to 6 carbon atoms with the proviso that at least one R is an alkenyl radical,
wherein the molar ratio of the R3SiO1/2 units to SiO4/2 units has a value of from 0.5/1 to 1.5/1,
a first alkoxysilane-functional organosiloxane compound of a formula HSi(R2)2OSi(R2)2CH2CH2SiR2z(OR2)3-z, wherein each R2 is independently a monovalent hydrocarbon having 1 to 6 carbon atoms and wherein the subscript z is 0 or 11, and
in the presence of a first hydrosilylation catalyst;
(B) a reactive polymer comprising a (trimethoxysilylethyl)tetramethyldisiloxane-terminated polydimethylsiloxane having a viscosity of from 500 to 60,000 cps;
(C) a catalyst; and
(D) a crosslinker.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein a weight average molecular weight Mw of the reactive resin (A) is from 12,000 to 30,000 g/mole.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the reactive resin (A) has a hydroxyl content that is less than 1% by weight based on a total weight of the reactive resin (A).

### Claim 4 (depends on 1)

The composition according to claim 1, wherein a alkenyl radical content of the alkenyl-functional siloxane resin is 0.6 to 2.2 eight percent of a total weight of the alkenyl-functional siloxane resin.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein the reactive resin (A) further comprises, as a part of its hydrosilylation reaction product, an endcapper according to a formula R33SiO—(R32SiO)s—SiR32H or R43SiO—(R42SiO)t—(HR4SiO)—SiR43 , or combinations thereof, wherein each R3 and R4 is independently a hydrocarbon radical and wherein the subscripts s and t independently have values ranging from 0 to 10.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the reactive resin (A) further comprises, as a part of its hydrosilylation reaction product, an alkenyltrialkoxysilane according to a formula AlkSi(OR5)3, wherein R5 is a monovalent hydrocarbon having 1 to 6 carbon atoms, wherein Alk represents an alkenyl group having 2 to 6 carbon atoms, and wherein the alkenyl group is at the molecular terminal of the alkenyltrialkoxysilane of the reactive resin (A).

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the crosslinker (D) comprises a silane represented by monomers of a formula R104-ySiXy or oligomeric reaction products thereof in which R10 is selected from the group consisting of hydrocarbon radicals and substituted hydrocarbon radicals having 1-6 carbon atoms, X is a hydrolyzable group and the subscript y has a value of 2 to 4.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein a weight ratio of reactive resin (A) to reactive polymer (B) is from 40:60 to 80:20.

### Claim 9 (depends on 1)

A method for forming a substrate assembly, the method comprising:
(1) providing the moisture-curable hot melt silicone adhesive composition according to claim 1;
(2) heating the moisture-curable hot melt silicone adhesive composition to a temperature sufficient to induce flow of the composition;
(3) disposing the heated composition onto a first substrate and a second substrate such that the moisture-curable hot melt silicone adhesive composition is located between the first substrate and the second substrate; and
(4) curing the moisture-curable hot melt silicone adhesive composition to bond the first substrate to the second substrate to form the substrate assembly.

### Claim 10 (depends on 9)

A substrate assembly formed by the method according to claim 9.

### Claim 11

A method for forming a moisture-curable hot melt adhesive composition, the method comprising:
(a) forming a reactive resin comprising a hydrosilylation reaction product of a reaction of:
an alkenyl-functional siloxane resin comprising R3SiO1/2 units and SiO4/2 units, wherein each R is independently a monovalent hydrocarbon radical having 1 to 6 carbon atoms with the proviso that at least one R is an alkenyl radical, wherein the molar ratio of the R3SiO1/2 units to SiO4/2 units has a value of from 0.5/1 to 1.5/1, and
a first alkoxysilane-functional organosiloxane compound of the formula HSi(R2)2OSi(R2)2CH2CH2SiR2z(OR2)3-z, wherein each R2 is independently a monovalent hydrocarbon having 1 to 2 carbon atoms and wherein the subscript z is 0 or 1,
in the presence of a first hydrosilylation catalyst;
(b) providing a (trimethoxysilylethyl)tetramethyldisiloxane-terminated polydimethylsiloxane having a viscosity of from 500 to 60,000 cps as a reactive polymer;
(c) mixing the reactive resin and the reactive polymer to form a first mixture;
(d) heating the first mixture to a temperature ranging from 140° C. to 180° C. and extruding the mixture through a first extruder to form an extruded mixture;
(e) cooling the extruded mixture to a temperature below 95° C. to provide a cooled extruded mixture;
(f) introducing and mixing a moisture cure catalyst and a crosslinker to the cooled extruded mixture to form a second mixture; and
(g) extruding the second mixture through a second extruder to form a moisture-curable hot melt adhesive composition.

### Claim 12 (depends on 11)

The method according to claim 11, wherein the reactive resin further comprises, as a part of its hydrosilylation reaction product, an endcapper according to the formula R33SiO—(R32SiO)s—SiR32H or R43SiO—(R42SiO)t—(HR4SiO)—SiR43, or combinations thereof, wherein each R3 and R4 is independently a hydrocarbon radical and wherein the subscripts s and t independently have values ranging from 0 to 10.

### Claim 13 (depends on 11)

A moisture curable hot melt adhesive composition formed in accordance with the method according to claim 11.