# US 10,308,793 B2 · Nitrile rubber composition, latex composition of highly saturated nitrile rubber, and cross-linked rubber

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- Number: US 10,308,793 B2
- Document ID: US10308793B2
- Status: Granted
- Kind: B2
- Application number: 15/527,948
- Filed: 2015-11-20
- Published: 2017-11-16
- Granted: 2019-06-04
- Earliest claimed: 2014-11-27
- Assignees: Zeon Corporation
- Applicants: Zeon Corporation
- Inventors: Sayaka Inoue; Tomonori Nakashima
- Web page: https://patentgrep.com/patent/US10308793B2

## CPC

- C08L 15/005: {Hydrogenated nitrile rubber}
- C08J 3/26: of latex
- C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators}
- C08K 5/13: Phenols; Phenolates
- C08K 7/02: Fibres or whiskers
- C08L 9/02: Copolymers with acrylonitrile
- C08L 9/04: Latex
- C08L 13/02: Latex
- C08J 2415/00: Characterised by the use of rubber derivatives (C08J2411/00, C08J2413/00 takes precedence)
- C08L 2312/02: with dienes
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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

A nitrile rubber composition comprising a highly saturated nitrile rubber (A) containing α,β-ethylenically unsaturated nitrile monomer units in a ratio of 8 to 60 wt % and having an iodine value of 120 or less and an alkylated phenol compound (B), wherein a ratio of content of the alkylated phenol compound (B) with respect to a total of the highly saturated nitrile rubber (A) and the alkylated phenol compound (B) is 0.01 to 1 wt %, and a difference (η2−η1) between a plasticity number η2 after storage at 70° C. for 7 days in a state of an aqueous dispersion by being dispersed in water and a plasticity number η1 before the storage is 12 or less is provided.

## Claims

### Claim 1

A nitrile rubber composition comprising:
a highly saturated nitrile rubber (A) containing α,β-ethylenically unsaturated nitrile monomer units in a ratio of 8 to 60 wt % and having an iodine value of 120 or less;
an alkylated phenol compound (B); and
an organic staple fiber,
wherein:
a ratio of content of the alkylated phenol compound (B) with respect to a total of the highly saturated nitrile rubber (A) and the alkylated phenol compound (B) is 0.01 to 1 wt %, and
a difference (η2−η1) between a plasticity number η2 after storage at 70° C. for 7 days in a state of an aqueous dispersion by being dispersed in water and a plasticity number η1 before the storage is 12 or less.

### Claim 2 (depends on 1)

The nitrile rubber composition according to claim 1, wherein the ratio of content of the alkylated phenol compound (B) with respect to a total of the highly saturated nitrile rubber (A) and the alkylated phenol compound (B) is 0.01 to 0.95 wt %.

### Claim 3 (depends on 1)

The nitrile rubber composition according to claim 1, wherein the alkylated phenol compound (B) is a compound represented by the following general formula (1) or a compound represented by the following general formula (2):
where, in the general formula (1), each of R1 is respectively independently an alkyl group having 1 to 7 carbon atoms, alkoxy group having 1 to 5 carbon atoms, amino group, amino group substituted by an alkyl group having 1 to 4 carbon atoms, or nitrogen-containing heterocyclic group, and “n” is an integer of 1 to 5; in the above general formula (1), at least one of R1 is an alkyl group having 1 to 7 carbon atoms:
where, in the general formula (2), each of R2 and R3 is respectively independently an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, amino group, amino group substituted by an alkyl group having 1 to 4 carbon atoms, or nitrogen-containing heterocyclic group, A is a chemical single bond or alkylene group having 1 to 4 carbon atoms, and each of “m” and “k” is respectively independently an integer of 1 to 4; in the above general formula (2), at least one of R2 is an alkyl group having 1 to 7 carbon atoms, while in the above general formula (2), at least one of R3 is an alkyl group having 1 to 7 carbon atoms.

### Claim 4

A latex composition of a highly saturated nitrile rubber comprising:
a highly saturated nitrile rubber (A) containing α,β-ethylenically unsaturated nitrile monomer units in a ratio of 8 to 60 wt % and having an iodine value of 120 or less;
an alkylated phenol compound (B); and
an organic staple fiber,
wherein:
a ratio of content of the alkylated phenol compound (B) with respect to a total of the highly saturated nitrile rubber (A) and the alkylated phenol compound (B) is 0.01 to 1 wt %, and
a difference (η2−η1) between a plasticity number η2 of a coagulated product after storage at 70° C. for 7 days and a plasticity number η1 of a coagulated product before the storage is 12 or less.

### Claim 5 (depends on 4)

The latex composition of a highly saturated nitrile rubber according to claim 4, wherein the ratio of content of the alkylated phenol compound (B) with respect to a total of the highly saturated nitrile rubber (A) and the alkylated phenol compound (B) is 0.01 to 0.95 wt %.

### Claim 6 (depends on 4)

The latex composition of a highly saturated nitrile rubber according to claim 4, wherein the alkylated phenol compound (B) is a compound represented by the following general formula (1) or a compound represented by the following general formula (2):
where, in the general formula (1), each of R1 is respectively independently an alkyl group having 1 to 7 carbon atoms, alkoxy group having 1 to 5 carbon atoms, amino group, amino group substituted by an alkyl group having 1 to 4 carbon atoms, or nitrogen-containing heterocyclic group, and “n” is an integer of 1 to 5; in the above general formula (1), at least one of R1 is an alkyl group having 1 to 7 carbon atoms:
where, in the general formula (2), each of R2 and R3 is respectively independently an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, amino group, amino group substituted by an alkyl group having 1 to 4 carbon atoms, or nitrogen-containing heterocyclic group, A is a chemical single bond or alkylene group having 1 to 4 carbon atoms, and each of “m” and “k” is respectively independently an integer of 1 to 4; in the above general formula (2), at least one of R2 is an alkyl group having 1 to 7 carbon atoms, while in the above general formula (2), at least one of R3 is an alkyl group having 1 to 7 carbon atoms.

### Claim 7 (depends on 1)

A cross-linkable nitrile rubber composition obtained by mixing a cross-linking agent into the nitrile rubber composition according to claim 1.

### Claim 8 (depends on 7)

A cross-linked rubber obtained by cross-linking a cross-linkable nitrile rubber composition according to claim 7.

### Claim 9 (depends on 4)

A cross-linkable nitrile rubber composition obtained by mixing a cross-linking agent into a nitrile rubber composition obtained by coagulating the latex composition of a highly saturated nitrile rubber according to claim 4.

### Claim 10 (depends on 9)

A cross-linked rubber obtained by cross-linking a cross-linkable nitrile rubber composition according to claim 9.

### Claim 11 (depends on 1)

The nitrile rubber composition according to claim 1, wherein the alkylated phenol compound (B) is 2,6-di-tert-butyl-4-methylphenol or 2,2′-methylenebis(4-methyl-6-tert-butylphenol).

### Claim 12 (depends on 4)

The latex composition of a highly saturated nitrile rubber according to claim 4, wherein the alkylated phenol compound (B) is 2,6-di-tert-butyl-4-methylphenol or 2,2′-methylenebis(4-methyl-6-tert-butylphenol).