# US 9,518,141 B2 · Resol-type para-octylphenol-formaldehyde co-condensation resin and method for producing the same

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- Number: US 9,518,141 B2
- Document ID: US9518141B2
- Status: Granted
- Kind: B2
- Application number: 14/387,107
- Filed: 2013-02-28
- Published: 2015-02-19
- Granted: 2016-12-13
- Earliest claimed: 2012-03-27
- Assignees: Taoka Chemical Co., Ltd.
- Applicants: Taoka Chemical Co., Ltd.
- Inventors: Fumiya Ozaki; Hiroyuki Kashimoto; Nobuyuki Sato; Takafumi Yamamoto
- Web page: https://patentgrep.com/patent/US9518141B2

## CPC

- C08G 8/12: with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
- C08L 9/00: Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L 23/26: modified by chemical after-treatment (saponified copolymers C08L23/0861; unsaturated acid salts C08L23/0876)
- C08L 61/06: of aldehydes with phenols
- 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

A resol-type para-octylphenol-formaldehyde co-condensation resin and a method for producing the same are provided, the resol-type para-octylphenol-formaldehyde co-condensation resin having a content of a para-octylphenol monomer of 1 wt. % or less, having a total content of an aliphatic hydrocarbon, a halogenated aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated aromatic hydrocarbon, and an alcohol having 1 to 8 carbon atoms of 1 wt. % or less, the aliphatic hydrocarbon, the halogenated aliphatic hydrocarbon, the aromatic hydrocarbon, the halogenated aromatic hydrocarbon, and the alcohol having a boiling point of 60° C. or more, having a softening point of 70 to 105° C., and having an acid value of 20 to 28 KOHmg/g. The resol-type para-octylphenol-formaldehyde co-condensation resin can be used as a resin cross-linking agent for a rubber.

## Claims

### Claim 1

A resol-type para-octylphenol-formaldehyde co-condensation resin,
having a content of a para-octylphenol monomer of 1 wt. % or less,
having a total content of an aliphatic hydrocarbon, a halogenated aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated aromatic hydrocarbon, and an alcohol having 1 to 8 carbon atoms of 1 wt. % or less, the aliphatic hydrocarbon, the halogenated aliphatic hydrocarbon, the aromatic hydrocarbon, the halogenated aromatic hydrocarbon, and the alcohol having a boiling point of 60° C. or more,
having a softening point of 70 to 105° C., and
having an acid value of 20 to 28 KOHmg/g.

### Claim 2 (depends on 1)

A rubber composition, comprising:
100 parts by weight of a rubber; and
1 to 20 parts by weight of the resol-type para-octylphenol-formaldehyde co-condensation resin according to claim 1.

### Claim 3 (depends on 1)

A method for producing the resol-type para-octylphenol-formaldehyde co-condensation resin according to claim 1, the method comprising the steps of:
(1) reacting para-octylphenol with formaldehyde at 40 to 100° C. using a hydroxide of an alkali metal as a catalyst in an amount of 0.15 to 0.24 equivalent per equivalent of the para-octylphenol, and in the presence of at least one of organic solvents selected from the group consisting of an aliphatic hydrocarbon, a halogenated aliphatic hydrocarbon, an aromatic hydrocarbon, a halogenated aromatic hydrocarbon, and an alcohol having 1 to 8 carbon atoms, the aliphatic hydrocarbon, the halogenated aliphatic hydrocarbon, the aromatic hydrocarbon, the halogenated aromatic hydrocarbon, and the alcohol having a boiling point of 60° C. or more, to obtain a resin liquid containing a resol-type para-octylphenol-formaldehyde co-condensation resin;
(2) neutralizing the resin liquid with 0.3 to 2 equivalents of an acid component per equivalent of a base content of the hydroxide; and
(3) concentrating and thereafter heating at 100 to 140° C. the neutralized resin liquid to provide the resol-type para-octylphenol-formaldehyde co-condensation resin with a weight-average molecular weight of 1400 to 2600.