# US 10,308,838 B2 · Moisture curable compositions

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- Number: US 10,308,838 B2
- Document ID: US10308838B2
- Status: Granted
- Kind: B2
- Application number: 15/107,181
- Filed: 2014-12-22
- Published: 2016-11-24
- Granted: 2019-06-04
- Earliest claimed: 2013-12-23
- Assignees: Dow Silicones Corporation
- Applicants: Dow Corning Corporation
- Inventors: Frederic Gubbels; David M. Hagan; Angela L. Stringer
- Web page: https://patentgrep.com/patent/US10308838B2

## CPC

- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C08G 77/08: characterised by the catalysts used
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C09J 5/00: Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J 183/06: containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence)
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

A moisture curable composition comprises: (A) a polymer containing reactive hydroxyl or hydrolysable groups bonded to silicon which groups are reactive in the presence of moisture; (B) a crosslinking agent comprising at least two groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A); (C) one or more reinforcing and/or non-reinforcing fillers; and (D) a silane having the structure (R1)m(Y1)3-mSi—Z1-G1-Z2—Si(R2)q(Y2)3-q. R1 and R2 are alkoxy groups containing from 1 to 6 carbons, Y1 and Y2 are alkyl groups containing from 1 to 8 carbons, Z1 and Z2 are alkylene groups having from 1 to 12 carbons, G1 is a chemical group containing a heteroatom with a lone pair of electrons, and m and q are independently 1, 2 or 3. Silane (D) is present in an amount of from 15 to 30% by weight of the composition and functions as a cure catalyst.

## Claims

### Claim 1

A moisture curable composition comprising:
(A) a polymer containing reactive hydroxyl or hydrolysable groups bonded to silicon which groups are reactive in the presence of moisture;
(B) a crosslinking agent comprising at least two groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A);
(C) one or more reinforcing and/or non-reinforcing fillers; and
(D) a silane having the structure
(R1)m(Y1)3-mSi—Z1-G1-Z2—Si(R2)q(Y2)3-q
where R1 and R2 are alkoxy groups containing from 1 to 6 carbons,
Y1 and Y2 are alkyl groups containing from 1 to 8 carbons,
Z1 and Z2 are alkylene groups having from 1 to 12 carbons,
G1 is a chemical group containing a heteroatom with a lone pair of electrons, and
m and q are independently 1, 2 or 3;
wherein silane (D) is present in an amount of from 15 to 30% by weight of the composition and functions as a cure catalyst for the composition.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein polymer (A) has the general formula (1):
X1-A′—X2 (1);
where X1 and X2 are independently selected from silicon containing groups which contain hydroxyl or hydrolysable substituents, and
A′ represents a polymer chain in which X1 or X2 groups incorporating hydroxyl and/or hydrolysable substituents is selected from the following groups: —Si(OH)3, —(Ra)Si(OH)2, (Ra)2SiOH, —(Ra)Si(ORb)2, —Si(ORb)3, —(Ra)2SiORb or —(Ra)2Si—Rc—SiRdp(ORb)3-p where each Ra independently represents a monovalent hydrocarbyl group;
each Rb and Rd is independently an alkyl or alkoxy group in which the alkyl groups have up to 6 carbon atoms;
Rc is a divalent hydrocarbon group which contains between 1 and 10 carbon atoms which may be interrupted by one or more siloxane spacers having up to six silicon atoms; and
p has the value 0, 1 or 2.

### Claim 3 (depends on 2)

The composition according to claim 2, polymer (A) is a diorganopolysiloxane that comprises:
20 to 100 parts by weight of (A-1) a diorganopolysiloxane capped at both molecular terminals with alkoxysilyl groups or hydroxysilyl groups; and
0 to 80 parts by weight of (A-2) a diorganopolysiloxane capped at one molecular terminal with an alkoxysilyl group or a hydroxysilyl group and capped at the other molecular terminal with an alkyl group or an alkenyl group.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein (A-1) and (A-2) are present in a (A-1):(A-2) weight ratio of from 100:0 to 20:80.

### Claim 5 (depends on 3)

The composition according to claim 3, wherein (A-1) and (A-2) are present in a (A-1):(A-2) weight ratio of from 100:0 to 60:40.

### Claim 6 (depends on 2)

The composition according to claim 2, wherein polymer chain A′ is a siloxane-containing polymer chain comprising siloxane units of the formula (2):
—(R5sSiO(4-s/2)— (2);
where each R5 is independently an organic group and s has, on average, a value of from 1 to 3.

### Claim 7 (depends on 6)

The composition in accordance with claim 6, wherein:
i) each R5 is independently a hydrocarbon group having from 1 to 18 carbon atoms, a substituted hydrocarbon group having from 1 to 18 carbon atoms or a hydrocarbonoxy group having up to 18 carbon atoms;
ii) s has, on average, a value of from 1.8 to 2.2; or
iii) both i) and ii).

### Claim 8 (depends on 2)

The composition in accordance with claim 2, wherein each Ra independently represents an alkyl group having from 1 to 8 carbon atoms, alternatively each Ra is a methyl group.

### Claim 9 (depends on 1)

The composition in accordance with claim 1, wherein the composition is a two part composition comprising:
I) a base composition comprising;
30 to 70 weight % of polymer (A), and
30 to 70 weight % of filler(s) (C), and
optionally one or more additives,
with the total % weight of the base composition being 100 weight %; and
II) a cross-linking composition comprising;
crosslinking agent (B), and
silane (D) in a ratio of (B):(D) of between 1:9 and 9:1;
with the base composition and cross-linking composition being in a ratio of from 15:1 to 1:1.

### Claim 10 (depends on 9)

The composition in accordance with claim 9, wherein the cross-linking composition further comprises:
(E) one or more polymers unreactive with components (B) and (D); and/or
(F) a pigment or coloured filler.

### Claim 11 (depends on 10)

The composition in accordance with claim 10, wherein polymer(s) (E) is present, functions as a plasticiser or extender, and is selected from polydimethylsiloxanes having terminal triorganosiloxy groups or from organic polymers.

### Claim 12 (depends on 11)

The composition in accordance with claim 11, wherein polymer(s) (E) is selected from mixtures of paraffinic and naphthenic hydrocarbons, paraffin oils comprising cyclic paraffins and non-cyclic paraffins and hydrocarbon fluids containing naphthenics, polycyclic naphthenics and paraffins.

### Claim 13 (depends on 11)

The composition in accordance with claim 11, wherein polymer(s) (E) is selected from polydimethylsiloxanes having terminal triorganosiloxy groups and wherein the organic substituents of such groups are methyl, vinyl, phenyl, or combinations thereof.

### Claim 14 (depends on 10)

The composition in accordance with claim 10, wherein the cross-linking composition comprises:
2 to 50 weight % of crosslinking agent (B);
silane (D);
5 to 30 weight % of polymer(s) (E); and
1 to 15 weight % of filler(s) (F).

### Claim 15 (depends on 1)

The composition in accordance with claim 1, wherein silane (D) is selected from the group of Bis[3-trimethoxysilyl)propylamine, Bis[3-triethoxysilyl)propylamine, Bis[3-trimethoxysilyl)butylamine, Bis[3-triethoxysilyl)butylamine, and mixtures thereof.

### Claim 16 (depends on 1)

The composition in accordance with claim 1 further comprising one or more additives selected from the group of plasticizers, extenders, rheology modifiers, adhesion promoters, pigments, heat stabilizers, flame retardants, UV stabilizers, chain extenders, cure modifiers, electrically conductive fillers, heat conductive fillers, fungicides, and/or biocides.

### Claim 17 (depends on 1)

The composition according to claim 1, wherein the composition is a one part composition comprising:
30 to 70 weight % of polymer (A);
0.5 to 10 weight % of crosslinking agent (B);
30 to 70 weight % of filler(s) (C); and
silane (D);
with the total weight % of the composition being 100 weight %.

### Claim 18 (depends on 1)

The composition in accordance with claim 1, wherein crosslinking agent (B) comprises at least three groups reactive with the silicon-bonded hydroxyl or hydrolysable groups of polymer (A).

### Claim 19 (depends on 1)

A coating, caulking, mold-making and/or encapsulating material comprising and/or formed from the composition in accordance with claim 1.

### Claim 20 (depends on 1)

A method of forming an elastomeric mass between at least two surfaces, said method comprising the steps of:
introducing a mass of a moisture curable composition between the surfaces; and
allowing the composition to cure thereby adhering the surfaces;
wherein the composition is in accordance with claim 1.