GB785656A - Rubber reaction product and preparation and uses thereof - Google Patents

Rubber reaction product and preparation and uses thereof

Info

Publication number
GB785656A
GB785656A GB21114/55A GB2111455A GB785656A GB 785656 A GB785656 A GB 785656A GB 21114/55 A GB21114/55 A GB 21114/55A GB 2111455 A GB2111455 A GB 2111455A GB 785656 A GB785656 A GB 785656A
Authority
GB
United Kingdom
Prior art keywords
nitroso
rubber
butyl rubber
naphthalene
toluene
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
Application number
GB21114/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB785656A publication Critical patent/GB785656A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/22Compounds containing nitrogen bound to another nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/30Introducing nitrogen atoms or nitrogen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/29Compounds containing one or more carbon-to-nitrogen double bonds
    • C08K5/31Guanidine; Derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A vulcanizable rubber is reacted before vulcanization with an aromatic compound having an empirical formula ONArMmY in which Ar is a mono or polynuclear aromatic hydrocarbon nucleus, M is an aliphatic divalent hydrocarbon group, m is zero or an integer and Y may be any one or more of the following groups: OR; C=OR; COOR; X1CH; NO2; NR2, where X is halogen and R is hydrogen or a monovalent hydrocarbon radical. Specified aromatic compounds are p-nitrosophenol, o-nitroso cresol the benzoatoester of a nitrosophenol, p-nitrosophenylmethylether, m-nitrosophenyl cyclohexyl ether, p-nitrosobenzyl alcohol, nitrosobenzyl ethyl ether, m-nitrosobenzaldehyde, p-nitrosophenyl ethyl ketone, p-nitrosobenzoic acid, and its methyl and ethyl esters, p-nitrosochlorobenzene, p-nitrosodichlorobenzene, p-nitrosocyano-benzene or -toluene or -naphthalene, nitrosonitrobenzene, -toluene or -naphthalene, nitrosoresorcinol, nitrososalicylic acid, nitrosohydroxyanisole, p-nitroso dimethylaniline, m-nitroso diethyl aniline, and p-nitroso-aniline, -toluidine or -xylidine. Specified rubbers are butyl rubber and butadiene-styrene copolymer rubber. The product may be compounded with the usual curing agents and vulcanized.ALSO:A natural rubber or Butyl rubber is reacted before vulcanization with an aromatic compound having an empirical formula ON ArMmY in which Ar is a mono or polynuclear aromatic hydrocarbon nucleus, M is an aliphatic divalent hydrocarbon group, m is zero or an integer and Y may be any one or more of the following groups; OR; C =OR; COOR; X; CN; NO2; NR2; where X is halogen and R is hydrogen or a monovalent hydrocarbon radical. Specified aromatic compounds are o-nitroso-cresol, p-nitroso-phenol, the benzoate ester of p-nitroso-phenol, p-nitroso-phenylmethyl ether, m-nitroso-phenyl cyclohexyl ether, p-nitrosobenzyl alcohol, nitroso-benzyl ethyl ether, m-nitroso benzaldehyde, p-nitrosophenyl ethyl ketone, p-nitrobenzoic acid and its methyl and ethyl esters, p-nitrosochlorobenzene, op-nitrosodichloro-benzene, p-nitrosocyanobenzene or -toluene or -naphthalene, nitrosonitrobenzene, -toluene or -naphthalene, nitroso-resorcinol, nitrososalicylic acid, nitrosohydroxy anisole, p-nitroso dimethylanidine, m-nitrosodiethylaniline and p-nitroso-aniline or -toluidine or -xylidine. The modified Butyl rubber may be used as a coating for automobile tyre cord. The cord is coated first with an aqueous solution of a resinous phenolic-aldehyde condensation product, preferably resorcinol-formaldehyde and then coated with a cement comprising a volatile solvent solution of the modified Butyl rubber, the cement preferably also containing a rubber pigment or filler such as carbon black, and dried. In particular, the auto tyre cord is coated with an aqueous solution of a resorcinal-formaldehyde resin formed by condensing 0,2 to 3 mols of formaldehyde per mole of resorcinol, in the presence of about 0,5 to 2 parts of sodium hydroxide catalyst per 100 parts resorcinol, the aqueous solution containing about 2-5 weight per cent of resin solids, dried, coated with a modified Butyl rubber cement made by first reacting in isobutylene-isoprene rubber having a Standinger molecular weight of 30,000 to 50,000 and an iodine number of 1 to 10, with 0,5 to 3 per cent p-nitrosophenol at 200-350 DEG DEG F. from 20-1 minutes, cooling at 75 DEG -125 DEG F., compounding the modified Butyl rubber with 30-50 parts of a powdered filler, hot-milling at 225 DEG -350 DEG F. for 15 to 3 minutes, cooling at 75 DEG -125 DEG F., adding the other compounding, including vulcanising, agents, and dissolved in a concentration of 8-20 per cent in a volatile hydrocarbon solvent of 6-8 carbon atoms, the cement also containing 1-10 per cent by volume of a volatile organic viscosity-reducer, and dried. This cord may then be bonded directly with a layer of unmodified Butyl rubber.
GB21114/55A 1954-07-23 1955-07-21 Rubber reaction product and preparation and uses thereof Expired GB785656A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US785656XA 1954-07-23 1954-07-23

Publications (1)

Publication Number Publication Date
GB785656A true GB785656A (en) 1957-10-30

Family

ID=22144845

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21114/55A Expired GB785656A (en) 1954-07-23 1955-07-21 Rubber reaction product and preparation and uses thereof

Country Status (5)

Country Link
BE (2) BE540014A (en)
DE (1) DE1137865B (en)
FR (1) FR1134478A (en)
GB (1) GB785656A (en)
NL (2) NL199125A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1237780B (en) * 1959-10-23 1967-03-30 Jupp Lebenstedt Vulcanizable, foamable polyolefin molding compounds
BE623634A (en) * 1961-10-19

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2616876A (en) * 1949-05-06 1952-11-04 Standard Oil Dev Co Curing rubbery substances with meta-dinitroso aromatic compounds

Also Published As

Publication number Publication date
NL199125A (en)
NL96261C (en)
BE540014A (en)
DE1137865B (en) 1962-10-11
BE565930A (en)
FR1134478A (en) 1957-04-11

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