GB677585A - Improvements in or relating to synthetic rubbers and method of stabilizing same - Google Patents

Improvements in or relating to synthetic rubbers and method of stabilizing same

Info

Publication number
GB677585A
GB677585A GB12310/50A GB1231050A GB677585A GB 677585 A GB677585 A GB 677585A GB 12310/50 A GB12310/50 A GB 12310/50A GB 1231050 A GB1231050 A GB 1231050A GB 677585 A GB677585 A GB 677585A
Authority
GB
United Kingdom
Prior art keywords
tert
methyl
phenol
heptane
methylene
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
GB12310/50A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB677585A publication Critical patent/GB677585A/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
    • C08K5/04Oxygen-containing compounds
    • C08K5/13Phenols; Phenolates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Synthetic rubbers, such as copolymers of butadiene with styrene or acrylonitrile, produced by the polymerization of the ingredients in latex form, are stabilized by addition to the latex, prior to coagulation, of a 2,21-methylene bis-(4,6-dialkyl phenol) of the general formula <FORM:0677585/IV (a)/1> where R1 is an alkyl radical of 1 to 3 carbon atoms, and R2 is a tert.-alkyl radical of 4 to 8 carbon atoms, the linkage from the tertiary carbon atom being directly to the benzene nucleus. Phenols specified are 2,21-methylene bis-(4-methyl-6-tert.-butyl phenol), and 2,21-methylene bis-(4-methyl-6-tert.-butyl phenol).ALSO:The preparation of 2,21-methylene bis-(4,6-dialkyl phenols) is described in examples. 2,21 - methylene - bis - (4 - methyl - 6 - tert. - butyl phenol) is prepared by treating a mixture of 4 - methyl - 6 - tert. - butyl phenol, concentrated hydrochloric acid and heptane with 36 per cent aqueous formaldehyde solution, followed by digestion at 50-60 DEG C.; after cooling the solid product is filtered off and washed with heptane-water mixture. 2,21-Methylene-bis-(4-methyl-6-tert.-octyl phenol) is prepared by treating a mixture of 2-tert.-octyl-4-methyl phenol and concentrated hydrochloric acid with 36 per cent aqueous formaldehyde, heptane is then added and the reaction mixture is heated at 55-60 DEG with stirring, the product is then washed with water, and the heptane-water mixture removed by distillation. The products are used as stabilizers for synthetic rubbers.
GB12310/50A 1949-07-25 1950-05-17 Improvements in or relating to synthetic rubbers and method of stabilizing same Expired GB677585A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US291211XA 1949-07-25 1949-07-25

Publications (1)

Publication Number Publication Date
GB677585A true GB677585A (en) 1952-08-20

Family

ID=21847340

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12310/50A Expired GB677585A (en) 1949-07-25 1950-05-17 Improvements in or relating to synthetic rubbers and method of stabilizing same

Country Status (6)

Country Link
BE (1) BE496125A (en)
CH (1) CH291211A (en)
DE (1) DE927535C (en)
FR (1) FR1088904A (en)
GB (1) GB677585A (en)
NL (1) NL73609C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1233588B (en) * 1958-05-13 1967-02-02 Bayer Ag Anti-aging agent for natural rubber
CN111088099A (en) * 2018-10-23 2020-05-01 中国石油化工股份有限公司 Gas engine oil composition and preparation method thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2883364A (en) * 1955-03-01 1959-04-21 Goodrich Co B F Stabilization of rubber with resinous bis-cresols

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE733031C (en) * 1938-10-14 1943-03-18 Ig Farbenindustrie Ag Process for stabilizing synthetic rubber-like substances
US2538355A (en) * 1949-07-25 1951-01-16 American Cyanamid Co 2, 2'-alkylene bis-4, 6-dialkyl phenols as rubber stabilizers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1233588B (en) * 1958-05-13 1967-02-02 Bayer Ag Anti-aging agent for natural rubber
CN111088099A (en) * 2018-10-23 2020-05-01 中国石油化工股份有限公司 Gas engine oil composition and preparation method thereof

Also Published As

Publication number Publication date
BE496125A (en)
FR1088904A (en) 1955-03-11
CH291211A (en) 1953-06-15
DE927535C (en) 1955-05-12
NL73609C (en)

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