# US 2013/0158159 A1 · Epoxy-containing polysiloxane oligomer compositions, process for making same and uses thereof

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- Number: US 2013/0158159 A1
- Document ID: US20130158159A1
- Status: Published application
- Kind: A1
- Application number: 13/329,430
- Filed: 2011-12-19
- Published: 2013-06-20
- Earliest claimed: 2011-12-19
- Assignees: Momentive Performance Materials Inc.
- Inventors: Narayana Padmanabha Iyer; Lesley Hwang; Vikram Kumar; Christian Geismann; Constantine Kondos; Shiu-Chin Su
- Web page: https://patentgrep.com/patent/US20130158159A1

## CPC

- C09D 7/63: organic
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C09J 183/06: containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence)
- 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
- 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

The present invention relates to stable, zero or low VOC epoxy-containing polysiloxane oligomer compositions that provide for a high degree of chemical resistance to compositions containing organic resins, while at the same time, maintaining or improving the flexibility of these organic resin-containing compositions, to processes for preparing epoxy-containing polysiloxane oligomer compositions, and to uses in coatings, sealants, adhesives, and composites containing the same.

## Claims

### Claim 1

An epoxy-containing polysiloxane oligomer composition comprising,
(i) from 5 to 65 mole percent of a polysiloxane of the Formula (I):
(ii) from 10 to 55 mole percent of a polysiloxane of the Formula (II):
(iii) from 5 to 45 mole percent of a polysiloxane of the Formula (III):
(iv) from 1 to 20 mole percent of a polysiloxane of the Formula (IV):
and
(v) from 0.1 to 20 mole percent of a polysiloxane of the Formula (V):
wherein each occurrence of R1 is —CH2CH2CH2— and the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

### Claim 2 (depends on 1)

The epoxy-containing polysiloxane oligomer composition of claim 1, wherein component (i) is from 9 to 30 mole percent, component (ii) is from 30 to 50 mole percent; component (iii) is from 20 to 40 mole percent; component (iv) is from 5 to 18 mole percent; component (v) is from 2 to 8 mole percent, wherein the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

### Claim 3 (depends on 2)

The epoxy-containing polysiloxane oligomer composition of claim 2, wherein component (i) is from 10 to 20 mole percent, component (ii) is from 35 to 48 mole percent; component (iii) is from 25 to 35 mole percent; component (iv) is from 7 to 15 mole percent; and component (v) is from 3 to 6 mole percent, wherein the mole percent of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v).

### Claim 4 (depends on 1)

The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has a viscosity of from 50 centistokes to 250 centistokes at 20° C. in accordance with ASTM method D-1545.

### Claim 5 (depends on 1)

The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has a number average molecular weight of from 500 grams per mole to 700 grams per mole.

### Claim 6 (depends on 1)

The epoxy-containing polysiloxane oligomer composition of claim 1 wherein the polysiloxane oligomer composition has less than 1 weight percent releasable alcohol, based upon the sum of the weights for components (i), (ii), (iii), (iv) and (v).

### Claim 7 (depends on 1)

The epoxy-containing polysiloxane oligomer composition of claim 1 further comprising a stabilizing agent having the Formula (VII):
R4(OR5)p (VII)
wherein:
R4 is a boron atom, a HP(═O)(−)2 group, a P(═O)(−)3 group, a R6C(═O)(−) group, a polyvalent hydrocarbon group containing from 3 to 20 carbon atoms or a polyvalent heterocarbon group containing from 3 to 20 carbon atoms;
each R5 is independently a hydrogen, a R6C(═O)(−) group, or a hydrocarbon containing from 1 to 6 carbon atoms;
each R6 is independently a monovalent hydrocarbon containing from 1 to 5 carbon atoms; and
p is an integer of from 1 to 6.

### Claim 8 (depends on 7)

The polysiloxane composition of claim 7 wherein the stabilizing agent is selected from the group consisting of boric acid, phosphoric acid, phosphorus acid, acetic acid, acetic acid anhydride, glycerol, 2-methyl-1,3-propanediol, 1-methoxy-2,3-propanediol, 1,2-hexanediol, and 2,3-dimethyl-2,3-butanediol.

### Claim 9 (depends on 1)

A process for making the polysiloxane composition of claim 1 comprising:
(a) hydrolyzing a silane of the general Formula (VI)
wherein:
R1 is —CH2CH2CH2—;
R2 is a monovalent alkyl group of from 1 to 3 carbon atoms; and
R3 is a monovalent alkyl group of from 1 to 3 carbon atoms;
in the presence of 2 to 15 moles of water per mole of the silane and, optionally, a hydrolysis catalyst, at a temperature of from 10° to 100° C. to provide an intermediate containing a silanol and an alcohol;
(b) removing the alcohol by distillation;
(c) removing water to condense the silanol to the desired polysiloxane oligomer composition comprising from 5 to 65 mole percent of the polysiloxane of the Formula (I), from 10 to 55 mole percent of the polysiloxane of the Formula (II), from 5 to 45 mole percent of the polysiloxane of the Formula (III), from 1 to 20 mole percent of the polysiloxane of the Formula (IV), and from 0.1 to 20 mole percent of the polysiloxane of the Formula (V), wherein the Formulae (I), (II), (III), (IV) and (V) are as defined above, wherein the mole percents of components (i), (ii), (iii), (iv) and (v) are based upon the sum of the molar amounts of components (i), (ii), (iii), (iv) and (v); and optionally
(d) adding a stabilizing agent,
thereby making the polysiloxane oligomer composition of claim 1.

### Claim 10 (depends on 9)

The process of claim 9, wherein the step (b) is carried out under a pressure of from 0.1 kilopascal to 200 kilopascal.

### Claim 11 (depends on 9)

The process of claim 9, wherein the step (c) is carried out under a pressure of from 0.1 kilopascal to 200 kilopascal.

### Claim 12 (depends on 9)

The process of claim 9, wherein the stabilizing agent has the Formula (VII):
R4(OR5)p (VII)
wherein:
R4 is a boron atom, a HP(═O)(−)2 group, a P(═O)(−)3 group, a R6C(═O)(−) group, a polyvalent hydrocarbon group containing from 3 to 20 carbon atoms or a polyvalent heterocarbon group containing from 3 to 20 carbon atoms;
each R5 is independently a hydrogen, a R6C(═O)(−) group, or a hydrocarbon containing from 1 to 6 carbon atoms;
each R6 is independently a monovalent hydrocarbon containing from 1 to 5 carbon atoms; and
p is an integer of from 1 to 6.

### Claim 13 (depends on 12)

The process of claim 12, wherein the stabilizing agent is selected from the group consisting of boric acid, phosphoric acid, phosphorus acid, acetic acid, acetic acid anhydride, glycerol, 2-methyl-1,3-propanediol, 1-methoxy-2,3-propanediol, 1,2-hexanediol, and 2,3-dimethyl-2,3-butane diol.

### Claim 14 (depends on 9)

The process of claim 9, further comprising carrying out the reaction of step (a) in the presence of a catalyst.

### Claim 15 (depends on 14)

The process of claim 14, wherein the catalyst is selected from the group consisting of metal salts, carboxylic acids, mineral acids or metal chelates.

### Claim 16 (depends on 1)

A composition comprising:
(i) epoxy-containing polysiloxane oligomer composition of claim 1;
(ii) an organic resin containing at least one functional group selected from the group consisting of epoxy, carboxylic acid, carboxylate anion, amino, ureido, urethane, mercapto, hydroxyl, alkoxysilyl and isocyanato; and
(iii) at least one additional component selected from the group consisting of a solvent, surfactant, particulate metal, pigment, biocide, filler, thixotrope, catalyst, curing agent, and leveling agent.

### Claim 17 (depends on 16)

The composition of claim 16, wherein the organic resin (ii) is an epoxy resin, an isocyanate-terminated polymer, an alkoxysilyl-terminated polyurethane, an alkoxysilyl-terminated polyether, a polyamide, a polyvinyl acetate, a polyvinyl alcohol, a polycarbonate, a polyamine, a copolymer of an alkene and (meth)acrylic, a copolymer of (meth)acrylate ester and (meth)acrylic acid, a terpolymer of an alkene, (meth)acrylate ester and (meth)acrylic acid, a urea-extended phenolic resin, a phenolic resin, or combination thereof.

### Claim 18 (depends on 16)

The composition of claim 16, wherein the organic resin (ii) is an emulsion or a dispersion.

### Claim 19 (depends on 16)

The composition of claim 16, wherein the organic resin (ii) is an epoxy resin selected from the group consisting of diglycidyl ether of bis-phenol A, diglycidyl ether of bis-phenol F, epoxy phenolic novolac resin, glycidyl ether of bisphenol, glycidyl ether of aliphatic polyol, glycidyl amide, glycidyl amine, thioglycidyl resins, glycidyl ester of dicarboxylic acids, tetraglycidyl ether of tetra phenol ethane, epoxy cresol novolac, and combinations thereof.

### Claim 20 (depends on 16)

The composition of claim 16, wherein the curing agent is selected from group consisting of dicarboxylic acids, carboxylic acid anhydrides, aziridines, fatty acid polyamides, dicyandiamide, acrylamides, imidazoles, hydrazidines, ethylene imines, thioureas, sulfonamides, acrylamides, guanamines, melamine, urea, polyamines, imidazoline-polyamines, and polyamine-amides.

### Claim 21 (depends on 16)

The composition of claim 16, wherein the solvent is selected from the group consisting of water, alcohols, ketones, esters, amides, ether-alcohols, and mixtures thereof.

### Claim 22 (depends on 16)

The composition of claim 16, wherein the composition is a coating, a sealant, an adhesive or a composite.

### Claim 23 (depends on 22)

The composition of claim 22, wherein the coating is selected from the group consisting of powder coatings, conversion coatings, passivation coatings, primers, high solids coatings, waterborne coatings, solventborne coatings, e-coatings and hardcoats.

### Claim 24 (depends on 23)

The composition of claim 23, wherein the coating is selected from the group consisting of conversion coatings and passivation coatings.

### Claim 25 (depends on 16)

A substrate having the composition of claim 16 applied thereto.

### Claim 26 (depends on 25)

The substrate of claim 25 wherein the composition is cured.