# US 9,518,182 B2 · Ester-functional polysiloxanes and copolymers made therefrom

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- Number: US 9,518,182 B2
- Document ID: US9518182B2
- Status: Granted
- Kind: B2
- Application number: 14/790,457
- Filed: 2015-07-02
- Published: 2016-01-07
- Granted: 2016-12-13
- Earliest claimed: 2014-07-03
- Assignees: Momentive Performance Materials Inc.
- Applicants: Momentive Performance Materials Inc.
- Inventors: Narayana Padmanabha Iyer; Indumathi Ramakrishnan; Anuj Mittal; Roy Rojas-Wahl; Samim Alam
- Web page: https://patentgrep.com/patent/US9518182B2

## CPC

- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08G 64/186: {containing polysiloxane sequences}
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08G 77/448: containing polycarbonate sequences
- C08L 69/00: Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C08G 77/12: containing silicon bound to hydrogen
- 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)

## Abstract

There is described a polysiloxane having the structure: wherein R1, R2, and R3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical, R4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen, R5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group, R6 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group, x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50. The polysiloxane is used to make various copolymers and polymer blends. A variety of articles can be made using the polysiloxane described as a polymer blend or copolymer.

## Claims

### Claim 1

A polyorganosiloxane having the structure of Formula I:
wherein R1, R2, and R3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical, wherein at least one of R1, R2 and R3 is selected from an unsaturated radical or an alkenyloxy radical; R4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen; R5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; R6 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group; and x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50.

### Claim 2 (depends on 1)

A composition comprising the polyorganosiloxane of claim 1, and a polymer selected from the group consisting of: polycarbonate homopolymers, polycarbonate copolymers, polycarbonate-polyesters, polyesters, polysulfones, polyethersulfones, polyetheretherketones, polyimides and polyetherimides.

### Claim 3 (depends on 2)

An article comprising the composition of claim 2.

### Claim 4 (depends on 3)

The article of claim 3, wherein the article is selected from the group consisting of mobile phone housings, frozen food service equipment, helmets, automotive windshields, motorcycle windshields, automotive sunroofs, dashboards, headlamps, and electric screens.

### Claim 5

A copolymer composition containing a copolymer comprising at least one polyorganosiloxane having units of Formula III:
wherein R1, R2, and R3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical, wherein at least one of R1, R2 and R3 is selected from an unsaturated radical or an alkenyloxy radical; R4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen; R5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50.

### Claim 6 (depends on 5)

The copolymer composition of claim 5, wherein the copolymer further comprises structural units of Formula IV:
wherein each R7 is a hydrocarbon radical having 1 to 60 carbon atoms, a divalent hydrocarbon group, a group derived from the structural unit of Formula V
where R8 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; and R9 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group; and V is selected from the group consisting of:
wherein R10, R11 are independently a hydrogen, halogen, an alkyl group having from 1 to 18 carbon atoms, an aryl group having from 3 to 14 carbon atoms, an aryloxy group having from 6 to 10 carbon atoms, an aralkyl group having from 7 to 20 carbon atoms, an alkoxy group having from 1 to 10 carbon atoms, a cycloalkyl group having from 6 to 20 carbon atoms, a cycloalkoxy group having from 6 to 20 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an aralkyloxy group, a nitro group, an aldehyde group, a cyano group, or a carboxyl group.

### Claim 7 (depends on 5)

The copolymer composition of claim 5, further comprising a polycarbonate homopolymer, a polycarbonate copolymer, a polycarbonate-polyester, a polyester, a polysulfone, a polyethersulfone, a polyetheretherketone, a polyimide or a polyetherimide.

### Claim 8 (depends on 5)

An article comprising the copolymer composition of claim 5.

### Claim 9 (depends on 6)

The copolymer composition of claim 6, wherein R9 is a hydroxy group and R10 is an alkyl group of from 1 to 6 carbon atoms.

### Claim 10 (depends on 8)

The article of claim 8, wherein the article is selected from the group consisting of mobile phone housings, frozen food service equipment, helmets, automotive windshields, motorcycle windshields, automotive sunroofs, dashboards, headlamps and electric screens.

### Claim 11 (depends on 5)

A method of making an article comprising: molding, shaping, or forming the copolymer composition of claim 5 to form the article.

### Claim 12

A method of preparing a polysiloxane copolymer, comprising polymerizing a polyorganosiloxane of Formula I represented by:
wherein R1, R2, and R3 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical, wherein at least one of R1, R2 and R3 is selected from an unsaturated radical or an alkenyloxy radical; R4 is independently a direct bond or hydrocarbon radical optionally substituted with oxygen and nitrogen; R5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; and R6 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group; wherein x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50,
with a compound of Formula V represented by
where R8 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; and R9 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group; and V is selected from the group consisting of
wherein R10, R11 are independently a hydrogen, halogen, an alkyl group having from 1 to 18 carbon atoms, an aryl group having from 3 to 14 carbon atoms, an aryloxy group having from 6 to 10 carbon atoms, an aralkyl group having from 7 to 20 carbon atoms, an alkoxy group having from 1 to 10 carbon atoms, a cycloalkyl group having from 6 to 20 carbon atoms, a cycloalkoxy group having from 6 to 20 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, an aralkyloxy group, a nitro group, an aldehyde group, a cyano group, or a carboxyl group in the presence of a carbonate precursor.

### Claim 13 (depends on 12)

The method of claim 12, wherein R9 is a hydroxy group and R10 is an alkyl group of from 1 to 6 carbon atoms.

### Claim 14 (depends on 12)

The method of claim 12, wherein the carbonate precursor is selected from the group consisting of phosgene, diphosgene, diarylcarbonate, bis(methylsalicyl)carbonate and a combination thereof.

### Claim 15 (depends on 12)

The method of claim 12, wherein the polymerizing is an interfacial polymerization process conducted in the presence of a solvent and optionally one or more catalysts.

### Claim 16 (depends on 15)

The method of claim 15, wherein the one or more catalysts are selected from the group consisting of: aliphatic amines, trialkylamine; and phase transfer catalysts of the formula (A3)4L+B, wherein each A is independently a C1-10 alkyl group, L is a nitrogen or a phosphorus atom; and B is a halogen atom, a C1-8 alkoxy group or C6-18 aryloxy group.

### Claim 17 (depends on 12)

The method of claim 12, wherein the polymerizing step is an interfacial polymerization process conducted in the presence of a solvent, a caustic, and optionally one or more catalysts, and wherein the carbonate precursor is phosgene, diphosgene, diarylcarbonate, bis(methylsalicyl)carbonate, or a combination thereof.

### Claim 18 (depends on 12)

The method of claim 12, wherein polymerizing comprises reacting bisphenol A with phosgene in a biphasic solvent in the presence of a phase transfer catalyst to form a bischloroformate; wherein the method further comprises adding polyorganosiloxane.

### Claim 19 (depends on 18)

The method of claim 18, wherein the bischloroformates of polyorganosiloxane are formed in a tube reactor, and then added into an interfacial polycondensation reactor with catalyst.