Epoxy-containing polysiloxane oligomer compositions, process for making same and uses thereof

Patent metadata

Field	Value
Publication number	US-9243152-B2
Application number	US-201414247645-A
Country	US
Kind code	B2
Filing date	Apr 8, 2014
Priority date	Dec 19, 2011
Publication date	Jan 26, 2016
Grant date	Jan 26, 2016

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.

First claim

What is claimed is:

1. A process for making an epoxy-containing polysiloxane oligomer composition wherein the composition comprises,
(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 R 1 is —CH 2 CH 2 CH 2 — 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),
and wherein the process comprises:
(a) hydrolyzing a silane of the general Formula (VI)

wherein:
R 1 is —CH 2 CH 2 CH 2 —;
R 2 is a monovalent alkyl group of from 1 to 3 carbon atoms; and
R 3 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 epoxy-containing polysiloxane oligomer composition.

2. The process of claim 1 , wherein the step (b) is carried out under a pressure of from 0.1 kilopascal to 200 kilopascal.

3. The process of claim 1 , wherein the step (c) is carried out under a pressure of from 0.1 kilopascal to 200 kilopascal.

4. The process of claim 1 , wherein the stabilizing agent has the Formula (VII):
R 4 (OR 5 ) p   (VII)

wherein:
R 4 is a boron atom, a HP(═O)(—) 2 group, a P(═O)(—) 3 group, a R 6 C(═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 R 5 is independently a hydrogen, a R 6 C(═O)(—) group, or a hydrocarbon containing from 1 to 6 carbon atoms;
each R 6 is independently a monovalent hydrocarbon containing from 1 to 5 carbon atoms; and
p is an integer of from 1 to 6.

5. The process of claim 4 , 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.

6. The process of claim 1 , further comprising carrying out the reaction of step (a) in the presence of a catalyst.

7. The process of claim 6 , wherein the catalyst is selected from the group consisting of metal salts, carboxylic acids, mineral acids or metal chelates.

8. A composition comprising:
(A) an epoxy-containing polysiloxane oligomer composition which comprises:
(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 R 1 is —CH 2 CH 2 CH 2 — 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);
(B) 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,
(C) 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.

9. The composition of claim 8 , wherein the organic resin (B) 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.

10. The composition of claim 8 , wherein the organic resin (B) is an emulsion or a dispersion.

11. The composition of claim 8 , wherein the organic resin (B) 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.

12. The composition of claim 8 , 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.

13. The composition of claim 8 , wherein the solvent is selected from the group consisting of water, alcohols, ketones, esters, amides, ether-alcohols, and mixtures thereof.

14. The composition of claim 8 , wherein the composition is a coating, a sealant, an adhesive or a composite.

15. The composition of claim 14 , wherein the coating is selected from the group consisting of powder coatings, conversion coatings, passivation coatings, prim

Assignees

• Momentive Performance Mat Inc

Inventors

• Iyer Narayana Padmanabha
• Hwang Lesley
• Kumar Vikram
• Geismann Christian
• Kondos Constantine
• Su Shiu-Chin

Classifications

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C09D7/1233 Primary

  Chemistry & Metallurgy · mapped topic

• C09J183/06

  containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence) · CPC title

• C09D7/63 Primary

  organic · CPC title