GB1148550A - Substituted benzylphenyl sulfides and their use as antioxidants - Google Patents

Substituted benzylphenyl sulfides and their use as antioxidants

Info

Publication number
GB1148550A
GB1148550A GB5494767A GB5494767A GB1148550A GB 1148550 A GB1148550 A GB 1148550A GB 5494767 A GB5494767 A GB 5494767A GB 5494767 A GB5494767 A GB 5494767A GB 1148550 A GB1148550 A GB 1148550A
Authority
GB
United Kingdom
Prior art keywords
formula
denotes
reacting
carbon atoms
denote
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
GB5494767A
Inventor
Thomas Adam Clayton
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.)
Uniroyal Inc
Original Assignee
Uniroyal Inc
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 Uniroyal Inc filed Critical Uniroyal Inc
Priority to GB5494767A priority Critical patent/GB1148550A/en
Publication of GB1148550A publication Critical patent/GB1148550A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings

Abstract

1,148,550. Substituted benzylphenyl sulphides. UNIROYAL Inc. 2 Dec., 1967, No. 54947/67. Heading C2C. [Also in Division C3] The invention comprises substituted benzylphenyl sulphides of the formula in which R 1 , R 2 , R 8 and R 4 denote alkyl groups of 1-12 carbon atoms, cycloalkyl groups of 6-8 carbon atoms or aralkyl groups of 7-9 carbon atoms. Alternatively, R 4 may denote hydrogen. The compounds may be prepared by reacting (a) a mercaptophenol of the formula under alkaline conditions with (b) a compound of the formula in which X denotes a benzothiazolyl sulphide radical or an N,N-dialkyldithiocarbamate residue of the formula -SC(S)NR 5 R 6 , in which R 5 and R 6 denote lower alkyl groups. A number of mercaptophenols suitable as reagents (a) are specified. The reaction may be effected at a temperature up to 100‹ C. in an aqueous medium, preferably containing a water-miscible solvent, or in a two-phase system. Examples are given. The products are useful as antioxidants (see Divisions C3 and C5). Intermediates of the third formula above in which X denotes a benzothiazolyl sulphide radical are obtainable by reacting a phenol of the formula with one molar equivalent each of formaldehyde and 2-mercaptobenzothiazole under acid conditions. A number of phenols which may participate in this reaction are specified. Intermediates of the third formula above in which X denotes an N,N-dialkyldithiocarbamate residue are obtainable by reacting a compound of the formula with carbon disulphide.
GB5494767A 1967-12-02 1967-12-02 Substituted benzylphenyl sulfides and their use as antioxidants Expired GB1148550A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5494767A GB1148550A (en) 1967-12-02 1967-12-02 Substituted benzylphenyl sulfides and their use as antioxidants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5494767A GB1148550A (en) 1967-12-02 1967-12-02 Substituted benzylphenyl sulfides and their use as antioxidants

Publications (1)

Publication Number Publication Date
GB1148550A true GB1148550A (en) 1969-04-16

Family

ID=10472537

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5494767A Expired GB1148550A (en) 1967-12-02 1967-12-02 Substituted benzylphenyl sulfides and their use as antioxidants

Country Status (1)

Country Link
GB (1) GB1148550A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2448415A1 (en) * 1973-10-11 1975-04-24 Raychem Corp ANTIOXYDANTS AND POLYMER COMPOUNDS CONTAINING THESE ANTIOXYDANTS
US4611023A (en) * 1984-02-03 1986-09-09 Ciba-Geigy Corporation Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions
WO1998051662A2 (en) * 1997-05-14 1998-11-19 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of vcam-1
US6670398B2 (en) 1997-05-14 2003-12-30 Atherogenics, Inc. Compounds and methods for treating transplant rejection
US6852878B2 (en) 1998-05-14 2005-02-08 Atherogenics, Inc. Thioketals and thioethers for inhibiting the expression of VCAM-1
AU2002300328B2 (en) * 1997-05-14 2006-04-13 Atherogenics, Inc Compounds and methods for the inhibition of the expression of VCAM-1
EP1695959A1 (en) * 1997-05-14 2006-08-30 Atherogenics, Inc. Compouds and methods for the inhibition of the expression of VCAM-1
US7294737B2 (en) 2004-04-20 2007-11-13 Atherogenics, Inc. Process of preparing esters and ethers of probucol and derivatives thereof
AU2006202461B2 (en) * 1997-05-14 2009-12-03 Atherogenics, Inc. Compositions and methods for the inhibition of the expression of VCAM-1
US8252840B2 (en) 2007-03-26 2012-08-28 Salutria Pharmaceuticals Llc Methods of derivatives of probucol for the treatment of type II diabetes

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2448415A1 (en) * 1973-10-11 1975-04-24 Raychem Corp ANTIOXYDANTS AND POLYMER COMPOUNDS CONTAINING THESE ANTIOXYDANTS
US4611023A (en) * 1984-02-03 1986-09-09 Ciba-Geigy Corporation Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions
US6670398B2 (en) 1997-05-14 2003-12-30 Atherogenics, Inc. Compounds and methods for treating transplant rejection
US6828447B2 (en) 1997-05-14 2004-12-07 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of VCAM-1
US6121319A (en) * 1997-05-14 2000-09-19 Atherogenics, Inc. Monoesters of probucol for the treatment of cardiovascular and inflammatory disease
US6548699B1 (en) 1997-05-14 2003-04-15 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of VCAM-1
US6602914B2 (en) 1997-05-14 2003-08-05 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of VCAM-1
US6617352B2 (en) 1997-05-14 2003-09-09 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of VCAM-1
US7375252B2 (en) 1997-05-14 2008-05-20 Atherogenics, Inc. Compounds and method for the inhibition of the expression of VCAM-1
WO1998051662A3 (en) * 1997-05-14 2000-03-02 Atherogenics Inc Compounds and methods for the inhibition of the expression of vcam-1
WO1998051662A2 (en) * 1997-05-14 1998-11-19 Atherogenics, Inc. Compounds and methods for the inhibition of the expression of vcam-1
AU2002300328B2 (en) * 1997-05-14 2006-04-13 Atherogenics, Inc Compounds and methods for the inhibition of the expression of VCAM-1
US7087645B2 (en) 1997-05-14 2006-08-08 Atherogenics, Inc. Compounds and methods for treating transplant rejection
EP1695959A1 (en) * 1997-05-14 2006-08-30 Atherogenics, Inc. Compouds and methods for the inhibition of the expression of VCAM-1
US7189870B2 (en) 1997-05-14 2007-03-13 Atherogenic, Inc. Compounds and methods for the inhibition of the expression of VCAM-1
AU2006202461B2 (en) * 1997-05-14 2009-12-03 Atherogenics, Inc. Compositions and methods for the inhibition of the expression of VCAM-1
EA009370B1 (en) * 1997-05-14 2007-12-28 Атеродженикс, Инк. Compound and pharmaceutical composition for the inhibition of the expression of vcam-1
EA009987B1 (en) * 1997-05-14 2008-04-28 Атеродженикс, Инк. Probucol derivatives for the treatment of diseases mediated by vcam-1
US6852878B2 (en) 1998-05-14 2005-02-08 Atherogenics, Inc. Thioketals and thioethers for inhibiting the expression of VCAM-1
US7294737B2 (en) 2004-04-20 2007-11-13 Atherogenics, Inc. Process of preparing esters and ethers of probucol and derivatives thereof
US8252840B2 (en) 2007-03-26 2012-08-28 Salutria Pharmaceuticals Llc Methods of derivatives of probucol for the treatment of type II diabetes

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