# US 8,569,405 B2 · Additive mixtures for styrenic polymers

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- Number: US 8,569,405 B2
- Document ID: US8569405B2
- Status: Granted
- Kind: B2
- Application number: 12/747,547
- Filed: 2009-01-19
- Published: 2011-02-24
- Granted: 2013-10-29
- Earliest claimed: 2008-01-28
- Assignees: BASF SE
- Applicants: Alex Wegmann; Sunghee Kim; Michèle Gerster
- Inventors: Alex Wegmann; Sunghee Kim; Michèle Gerster
- Web page: https://patentgrep.com/patent/US8569405B2

## CPC

- C08F 6/006: {Removal of residual monomers by chemical reaction, e.g. scavenging}
- C08J 3/226: {using a polymer as a carrier}
- C08K 5/005: {Stabilisers against oxidation, heat, light, ozone}
- C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)}
- C08J 2425/00: Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The invention describes a process for reducing the amount of saturated or unsaturated monomers and oligomers during production and processing of styrenic polymers comprising a mixture of at least two components selected from the group consisting of a) phenol thioethers, b) phenol acrylates, c) 3-arylbenzofuran-2-ones and d) 1,1-di-substituted ethylenes or tri-substituted ethylenes.

## Claims

### Claim 1

A process for reducing the amount of saturated or unsaturated monomers and oligomers during production and processing of styrenic polymers,
which process comprises adding to the styrenic polymers an additive mixture comprising at least two components selected from the group consisting of a) phenol thioethers, b) phenol acrylates, c) 3-arylbenzofuran-2-ones and d) 1,1-di-substituted ethylenes or tri-substituted ethylenes,
with the proviso that a mixture comprising a component a) and a component b) contains a third component selected from the group consisting of c) and d).

### Claim 2 (depends on 1)

A process according to claim 1, wherein the additive mixture comprises component a) a compound of formula I
wherein
R1 is hydrogen, C1-C20alkyl, styryl, α-methyl-styryl or —CH2—S—R3; or C1-C20alkyl substituted with C2-C20alkenyl, C3-C20alkinyl, C5-C9cycloalkyl, phenyl or tolyl;
R2 is C1-C20alkyl or —CH2—S—R3,
R3 is C1-C20alkyl; C1-C20alkyl substituted with phenyl, hydroxyl, cyano, formyl, acetyl or —O—CO—R5;
C2-C20alkenyl, C3-C20alkinyl, C5-C9cycloalkyl; or C5-C9cycloalkyl substituted with hydroxyl, phenyl, 4-chlorophenyl, 2-methoxycarbonylphenyl, p-tolyl, 1,3-benzthiazol-2-yl, —(CHR5)nCOOR6 or —(CHR5)nCONR7R8;
R4 is hydrogen or methyl,
R5 is hydrogen or C1-C6alkyl,
R6 is C1-C20alkyl; C3-C20alkyl interrupted with oxygen or sulfur; C5-C9cycloalkyl, phenyl, benzyl or tolyl,
R7 and R8 are independently of each other hydrogen or C1-C6alkyl, and
n is 1 or 2.

### Claim 3 (depends on 1)

A process according to claim 1, wherein the additive mixture comprises component b) a compound of formula II
wherein
R11 and R12 are each independently of the other C1-C25alkyl; C5-C12cycloalkyl unsubstituted or substituted by C1-C4alkyl; C7-C9phenylalkyl; or phenyl unsubstituted or substituted by C1-C4alkyl,
R13 is hydrogen or methyl,
R14 is hydrogen or C1-C8alkyl,
R15 is C1-C25alkyl; C2-C25alkyl interrupted by oxygen, sulfur or
C2-C24alkenyl;
C8-C30phenylalkenyl unsubstituted or substituted on the phenyl ring by halogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio; C5-C12cycloalkyl unsubstituted or substituted by C1-C4alkyl;
C8-C30phenylalkyl unsubstituted or substituted on the phenyl ring by halogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio; or phenyl unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy or C1-C4alkylthio, and
R16 is hydrogen or C1-C18alkyl.

### Claim 4 (depends on 1)

A process according to claim 1, wherein the additive mixture comprises component c) a compound of formula III
wherein
R19 is hydrogen or C1-C8alkyl,
R20 is C1-C12alkyl,
R21 is hydrogen, C1-C4alkyl or C2-C8alkanoyl,
R22 is hydrogen or C1-C8alkyl; or R21 and R22 or R22 and R23 together with the carbon atoms to which they are attached form a C6-C8cycloalkylene ring,
R23 is hydrogen, C1-C4alkyl or C1-C4alkoxy, and
R24 is hydrogen or C1-C12alkyl.

### Claim 5 (depends on 1)

A process according to claim 1, wherein the additive mixture comprises component d) a compound of formula A-1, A-2a or A-2b

### Claim 6 (depends on 1)

A process according to claim 1, comprising adding further additives.

### Claim 7 (depends on 6)

A process according to claim 6, wherein the further additives are light stabilizers, acid scavengers and/or antistatic agents.

### Claim 8 (depends on 1)

A process according to claim 1, wherein the mixture of at least two components is added in an amount of from 0.001 to 5%, based on the weight of the styrenic polymer.

### Claim 9

A mixture for reducing the amount of saturated or unsaturated monomers and oligomers during production and processing of styrenic polymers, comprising at least two components selected from the group consisting of a) phenol thioethers, b) phenol acrylates, c) 3-arylbenzofuran-2-ones and d) 1,1-di-substituted ethylenes or tri-substituted ethylenes; with the proviso that a mixture comprising a component a) and a component b) contains a third component selected from the group consisting of c) and d).

### Claim 10 (depends on 9)

A mixture according to claim 9 with the proviso that a mixture comprising a component a) and component b) is excluded.

### Claim 11

A composition comprising
i) a styrenic polymer, and
ii) an additive mixture comprising at least two components selected from the group consisting of a) phenol thioethers, b) phenol acrylates, c) 3-arylbenzofuran-2-ones and d) 1,1-di-substituted ethylenes or tri-substituted ethylenes; with the proviso that a mixture comprising a component a) and a component b) contains a third component selected from the group consisting of c) and d).

### Claim 12 (depends on 11)

A composition according to claim 11 which does not contain a mixture comprising a component a) and a component b).

### Claim 13 (depends on 11)

A composition according to claim 11 comprising further additives.

### Claim 14 (depends on 9)

A masterbatch composition comprising an additive mixture according to claim 9 and a thermoplastic material which is identical or compatible with the styrenic polymer.

### Claim 15 (depends on 14)

A masterbatch composition according to claim 14 comprising 10 to 80% by weight of said thermoplastic material.

### Claim 16 (depends on 9)

A shaped article containing a mixture according to claim 9.

### Claim 17 (depends on 12)

A composition according to claim 12 comprising further additives.

### Claim 18 (depends on 10)

A masterbatch composition comprising an additive mixture according to claim 10 and a thermoplastic material which is identical or compatible with the styrenic polymer.

### Claim 19 (depends on 18)

A masterbatch composition according to claim 18 comprising 10 to 80% by weight of said thermoplastic material.

### Claim 20 (depends on 10)

A shaped article containing a mixture according to claim 10.