GB751630A - Production of vulcanized rubber of improved resistance to cracking and compounds for use therein - Google Patents
Production of vulcanized rubber of improved resistance to cracking and compounds for use thereinInfo
- Publication number
- GB751630A GB751630A GB4929/54A GB492954A GB751630A GB 751630 A GB751630 A GB 751630A GB 4929/54 A GB4929/54 A GB 4929/54A GB 492954 A GB492954 A GB 492954A GB 751630 A GB751630 A GB 751630A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- rubber
- para
- alkyl
- phenylene diamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Vulcanized synthetic rubber with improved resistance to cracking under exposure is obtained by incorporating into a sulphur-vulcanizable synthetic rubber stock a vulcanizing agent and an N-alkyl-N1-phenyl-paraphenylene diamine in which the alkyl group contains at least six but not more than ten carbon atoms (see Group IV (b)) and maintaining the mixture at a vulcanizing temperature until vulcanization is effected. Between 0.2 and 5 per cent by weight of the phenylene diamine based on the weight of the rubber may be used. Specified synthetic rubbers include polymers of aliphatic conjugated dienes such as butadiene, isoprene, piperylene, dimethyl butadiene and ethyl butadiene and their copolymers with olefins containing a vinyl group such as styrene, a -methyl styrene, mono- and dichlorostyrene, vinyl naphthalene, divinyl benzene, vinyl diphenyl, vinyl carbazole, 2-vinyl-5-ethyl-pyridine, acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid and esters thereof and methyl vinyl ketone. The effect of the N-alkyl - N1 - phenyl - para - phenylene diamine compounds is shown by admixing the N-n-hexyl- or N-n-decyl-compounds with a butadiene-1 : 3-styrene copolymer composition containing the usual vulcanizing agents, vulcanizing and evaluating the cured compositions by exposure under dynamic conditions in an atmosphere of ozone. Similar compositions containing copolymers of butadiene-1 : 3-acrylonitrile copolymer or isobutylene-isoprene copolymer are described. The vulcanized rubbers so treated are also resistant to flex cracking and to ageing due to exposure to air or oxygen, even when the vulcanized rubber contains copper.ALSO:The invention comprises N-alkyl-N1-phenyl-para-phenylene diamines in which the alkyl groups contain at least six but not more than ten carbon atoms. The compounds are incorporated into sulphur-vulcanizable natural (see Group V) or synthetic (see Group IV (a)) rubber stocks and improve the resistance to cracking under exposure of the vulcanized rubber. In Example (1) a mixture of n-hexyl alcohol and N - phenyl - para - phenylene diamine are refluxed together in the presence of a nickel catalyst with concurrent removal of water, the reaction mixture extracted with ether and distilled to give N-hexyl-N1-phenyl-para-phenylene diamine; (2) as in (1) but using n-decanol and crystallizing the reaction mixture from heptane to yield N-n-decyl-N1-phenyl-para-phenylene diamine.ALSO:Vulcanized natural rubber with improved resistance to cracking under exposure is obtained by incorporating into a sulphur-vulcanizable natural rubber stock a vulcanizing agent and an N-alkyl-N1-phenyl-para-phenylene diamine in which the alkyl group contains at least six but not more than ten carbon atoms (see Group IV(b)) and maintaining the mixture at a vulcanizing temperature until vulcanization is effected. Between 0.2 and 5 per cent by weight of the phenylene diamine based on the weight of rubber may be used. The effect of the N-alkyl-N1-phenyl-para-phenylene diamine compounds is shown by admixing the N-n-hexyl-compound with a rubber composition containing the usual vulcanizing agents and fillers, and then vulcanizing and evaluating the cured compositions by exposure under dynamic conditions in an atmosphere of ozone. The antioxidant action of the N-n-hexyl-compound is also shown in cured compositions containing copper.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US751630XA | 1953-02-19 | 1953-02-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB751630A true GB751630A (en) | 1956-07-04 |
Family
ID=22123971
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4929/54A Expired GB751630A (en) | 1953-02-19 | 1954-02-19 | Production of vulcanized rubber of improved resistance to cracking and compounds for use therein |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB751630A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1153158B (en) * | 1957-10-30 | 1963-08-22 | Firestone Tire & Rubber Co | Rubber compounds vulcanized with sulfur and containing antiozonants |
US3163616A (en) * | 1956-08-31 | 1964-12-29 | Burke Oliver W Jun | P-phenylenediamine stabilizers for elastomers and compositions containing the same |
DE1220124B (en) * | 1961-09-05 | 1966-06-30 | Bayer Ag | Anti-ozone agent for natural or synthetic rubber |
CN101333304B (en) * | 2008-07-28 | 2011-09-28 | 常州市五洲化工有限公司 | Rubber antiager and method for preparing same |
-
1954
- 1954-02-19 GB GB4929/54A patent/GB751630A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3163616A (en) * | 1956-08-31 | 1964-12-29 | Burke Oliver W Jun | P-phenylenediamine stabilizers for elastomers and compositions containing the same |
DE1153158B (en) * | 1957-10-30 | 1963-08-22 | Firestone Tire & Rubber Co | Rubber compounds vulcanized with sulfur and containing antiozonants |
DE1220124B (en) * | 1961-09-05 | 1966-06-30 | Bayer Ag | Anti-ozone agent for natural or synthetic rubber |
CN101333304B (en) * | 2008-07-28 | 2011-09-28 | 常州市五洲化工有限公司 | Rubber antiager and method for preparing same |
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