GB1012945A - Antiozonants for diene rubbers - Google Patents

Antiozonants for diene rubbers

Info

Publication number
GB1012945A
GB1012945A GB1902162A GB1902162A GB1012945A GB 1012945 A GB1012945 A GB 1012945A GB 1902162 A GB1902162 A GB 1902162A GB 1902162 A GB1902162 A GB 1902162A GB 1012945 A GB1012945 A GB 1012945A
Authority
GB
United Kingdom
Prior art keywords
mols
mixed
aniline
mol
toluidines
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
GB1902162A
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.)
Goodyear Tire and Rubber Co
Original Assignee
Goodyear Tire and Rubber 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 Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co
Publication of GB1012945A publication Critical patent/GB1012945A/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
    • C08K5/17Amines; Quaternary ammonium compounds
    • C08K5/18Amines; 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An oxidizable diene rubber contains as an antiozonant a mixture of ring alkylated diphenyl - para - phenylenediamines melting below 80 DEG C. prepared by reacting in the presence of a condensation catalyst (a) a compound selected from the group consisting of hydroquinone and ring-alkylated hydroquinones, and (b) per mol. of compound from group (a) an amine mixture selected from the group consisting of 2.0 to 2.5 mols. of mixed xylidines; 1.0 to 1.25 mols. mixed toluidines and 1.0 to 1.25 mols. mixed xylidines; 1.0 to 1.25 mols. 2,4-dimethyl aniline and 1.0 to 1.25 mols. ortho-toluidine; 1.0 to 1.25 mols. mixed toluidines, 0.7 to 1.0 mol. of mixed xylidines and 0.1 to 0.5 mol. of aniline; 1.0 to 1.25 mols. of mixed xylidines and 1.0 to 1.25 mols. of ortho-ethyl aniline; 1.0 to 1.25 mols. of ortho-ethyl aniline and 1.0 to 1.25 mols. of aniline; 1.0 to 1.25 mols. of ortho toluidine and 1.0 to 1.25 mols. ortho-ethyl aniline; 2.0 to 2.5 mols. of dodecyl anilines; 1.0 to 1.25 mols. of mixed toluidines and 1.0 to 1.25 mols. of amyl anilines; 1.0 to 1.25 mols. of mixed toluidines and 1.0 to 1.25 mols. of dodecylanilines; 1.0 to 1.25 mols. of mixed toluidines, 0.5 to 0.625 mol. of aniline and 0.5 to 0.625 mol. of mixed xylidines; 1.0 to 1.25 mols. of mixed toluidines, 0.5 to 0.625 mol. of amyl anilines, and 0.5 to 0.625 mol. of 2,6-diethyl aniline; 1.0 to 1.25 mols. of mixed toluidines and 1.0 to 1.25 mols. of ortho-ethyl aniline; 1.0 to 1.25 mols. of mixed toluidines, 0.5 to 0.625 mol. of 2,6-diethyl aniline and 0.5 to 0.625 mol. of ortho-ethyl aniline; 1.0 to 1.25 mols. of mixed toluidines, 0.5 to 0.625 mol. of amyl aniline and 0.5 to 0.625 mol. of ortho-ethyl aniline; 1.0 to 1.25 mols. of mixed xylidines and 1.0 to 1.25 mols. of aniline; 1.0 to 1.25 mols. of aniline, 0.5 to 0.625 mol. of 2,6-diethyl aniline and 0.5 to 0.625 mol. of ortho-ethyl aniline; 1.0 to 1.25 mols. of mixed cumidines and 1.0 to 1.25 mols. of mixed toluidines; 2.0 to 2.5 mols. of mixed cumidines. The ring alkylated diphenyl-para-phenylene-diamine may be prepared by reacting (a) a compound selected from the group consisting of hydroquinone and ring alkylated hydroquinone and, (b) per mol. of compound from group (a) an amine mixture consisting of from 2.0 to 2.5 mols. of mixed xylidines, or (b) per mol. of compound from group (a) an amine mixture consisting of from 1.0 to 1.25 mols. of mixed toluidine, 0.7 to 1.0 mols. of mixed xylidines and 0.1 to 0.5 mols. of aniline, or (b) per mol. of compound from group (a) an amine mixture consisting of from 2.0 to 2.5 mols. of mixed cumidines, or (b) per mol. of compound from group (a) an amine mixture consisting of from 1.0 to 1.25 mols. of mixed cumidines and from 1.0 to 1.25 mols. of mixed toluidines. Specified rubbers are natural rubber polychloroprene, as 1,4-polyisoprene, as 1,4-polybutadiene, butadiene-styrene, and butyl rubber.ALSO:An antizonant comprises a mixture of ring alkylated diphenyl - para - phenylenediamines melting below 80 DEG C. prepared by reacting in the presence of a condensation catalyst (a) a compound selected from the group consisting of hydroquinone and ring-alkylated hydroquinones and (b) per mol of compound from group (a) an amine mixture selected from the group consisting of 2.0 to 2.5 mols of mixed xylidines; 1.0 to 1.25 mols mixed toluidines and 1.0 to 1.25 mols mixed xylidines; 1.0 to 1.25 mols 2,4-dimethyl aniline and 1.0 to 1.25 mols ortho-toluidine; 1.0 to 1.25 mols mixed toluidines, 0.7 to 1.0 mol of mixed xylidines and 0.1 to 0.5 mol of aniline; 1.0 to 1.25 mols of mixed xylidines and 1.0 to 1.25 mols of ortho-ethyl aniline; 1.0 to 1.25 mols of ortho-ethyl aniline and 1.0 to 1.25 mols of aniline; 1.0 to 1.25 mols of ortho toluidine and 1.0 to 1.25 mols ortho-ethyl aniline; 2.0 to 2.5 mols of dodecyl anilines; 1.0 to 1.25 mols of mixed toluidines and 1.0 to 1.25 mols of amyl anilines; 1.0 to 1.25 mols of mixed toluidines and 1.0 to 1.25 mols of dodecylanilines; 1.0 to 1.25 mols of mixed toluidines, 0.5 to 0.625 mol of aniline and 0.5 to 0.625 mol of mixed xylidines; 1.0 to 1.25 mols of mixed toluidines, 0.5 to 0.625 mol of amyl anilines, and 0.5 to 0.625 mol of 2,6-diethyl aniline; 1.0 to 1.25 mols of mixed toluidines and 1.0 to 1.25 mols of ortho-ethyl aniline; 1.0 to 1.25 mols of mixed toluidines, 0.5 to 0.625 mol of 2,6-diethyl aniline and 0.5 to 0.625 mol of ortho-ethyl aniline; 1.0 to 1.25 mols of mixed toluidines, 0.5 to 0.625 mol of amyl aniline and 0.5 to 0.625 mol of ortho-ethyl aniline; 1.0 to 1.25 mols of mixed xylidines and 1.0 to 1.25 mols of aniline; 1.0 to 1.25 mols of aniline, 0.5 to 0.625 mol of 2,6-diethyl aniline and 0.5 to 0.625 mol of ortho-ethyl aniline; 1.0 to 1.25 mols. of mixed cumidines and 1.0 to 1.25 mols of mixed toluidines; 2.0 to 2.5 mols of mixed cumidines. The ring alkylated diphenyl-paraphenylene-diamine may be prepared by reaching (a) a compound selected from the group consisting of hydroquinone and ring alkylated hydroquinone and, (b) per mol of compound from group (a) and an amine mixture consisting of from 2.0 to 2.5 mols of mixed xylidines, or (b) per mol of compound from group (a) an amine mixture consisting of from 1.0 to 1.25 mols of mixed toluidine, 0.7 to 1.0 mols of mixed xylidines and 0.1 to 0.5 mols of aniline, or (b) per mol of compound from group (a) an amine mixture consisting of from 2.0 to 2.5 mols of mixed cumidines, or (b) per mol of compound from group (a) an amine mixture consisting of from 1.0 to 1.25 mols of mixed cumidines and from 1.0 to 1.25 mols of mixed toluidines.
GB1902162A 1961-06-13 1962-05-17 Antiozonants for diene rubbers Expired GB1012945A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11667461A 1961-06-13 1961-06-13

Publications (1)

Publication Number Publication Date
GB1012945A true GB1012945A (en) 1965-12-15

Family

ID=22368560

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1902162A Expired GB1012945A (en) 1961-06-13 1962-05-17 Antiozonants for diene rubbers

Country Status (3)

Country Link
JP (1) JPS4929617B1 (en)
GB (1) GB1012945A (en)
SE (1) SE312675B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3513124A (en) * 1967-01-31 1970-05-19 Du Pont Antiozonants for chloroprene polymers
EP0041915A1 (en) * 1980-06-09 1981-12-16 The Goodyear Tire & Rubber Company Styrylated amine antioxidants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110591151B (en) * 2018-06-12 2022-10-18 圣奥化学科技有限公司 Rubber composition for tire comprising novel long-acting rubber antioxidant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3513124A (en) * 1967-01-31 1970-05-19 Du Pont Antiozonants for chloroprene polymers
EP0041915A1 (en) * 1980-06-09 1981-12-16 The Goodyear Tire & Rubber Company Styrylated amine antioxidants

Also Published As

Publication number Publication date
SE312675B (en) 1969-07-21
JPS4929617B1 (en) 1974-08-06

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