GB1396469A - Thiaalkyl substituted phenols and their use in the stabili sation of organic materials - Google Patents

Thiaalkyl substituted phenols and their use in the stabili sation of organic materials

Info

Publication number
GB1396469A
GB1396469A GB4347273A GB4347273A GB1396469A GB 1396469 A GB1396469 A GB 1396469A GB 4347273 A GB4347273 A GB 4347273A GB 4347273 A GB4347273 A GB 4347273A GB 1396469 A GB1396469 A GB 1396469A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
denotes
formula
radical
thiaalkyl
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
GB4347273A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1396469A publication Critical patent/GB1396469A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
    • C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • 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
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • 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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • 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
    • C08K5/41—Compounds containing sulfur bound to oxygen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Lubricants (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

1396469 Thiaalkyl substituted phenols CIBAGEIGY AG 17 Sept 1973 [18 Sept 1972] 43472/73 Heading C2C [Also in Division C3] The novel compounds of Formula I in which R 1 and R 2 independently of one another denote alkyl with 1 to 5 carbon atoms, cycloalkyl or alkylcycloalkyl with 6 to 8 carbon atoms or aralkyl or alkylaralkyl with 7 to 9 carbon atoms, R 3 denotes hydrogen or methyl, X denotes alkylene with 3 to 18 carbon atoms, with the phenol radical and the sulphur atom being separated by 2 or 3 carbon atoms, Y denotes alkyl with 1 to 18 carbon atoms, cycloalkyl or alkylcycloalkyl with 5 to 8 carbon atoms, aralkyl or alkylaralkyl with 7 to 9 carbon atoms, oxaalkyl with 3 to 21 carbon atoms, thiaalkyl with 3 to 21 carbon atoms, mercaptoalkyl with 2 to 18 carbon atoms, alkoxycarbonylalkyl with 3 to 21 carbon atoms, carboxyalkyl with 2 or 3 carbon atoms, hydroxyalkyl with 2 to 8 carbon atoms, acyloxyalkyl with 4 to 20 carbon atoms, alkylene with 2 to 18 carbon atoms, oxaalkylene with 4 to 18 carbon atoms, thiaalkylene with 4 to 18 carbon atoms, hydroxyalkylene with 3 to 21 carbon atoms, acyloxyalkylene with 5 to 23 carbon atoms, alkoxyalkylene with 4 to 22 carbon atoms or one of the groups with heteroatoms in the radical Y being separated from sulphur, or the sulphur atoms being separated from one another, by at least 2 carbon atoms, n denotes 0, 1 or 2 and q denotes 1, 2, 3 or 4 may be prepared by reaction of one mole of a compound of Formula II in which Z denotes a radical of a C 3-18 alkene, the double bond in said alkene being either conjugated with or in the allyl position relative to the phenyl nucleus with one mole of a compound of Formula III at 50-160‹ C. in the presence of a radical forming agent to produce compounds of Formula I in which n is 0 which may be converted to compounds of Formula I in which n is 1 or 2 by reacting with an organic or inorganic oxidizing agent in a solvent at 0‹ to 100‹ C. The compounds of Formula I have application as stabilizers for organic materials such as polymers especially polyamides and polypropylene, stabilizing them against thermo oxidative degradation.
GB4347273A 1972-09-18 1973-09-17 Thiaalkyl substituted phenols and their use in the stabili sation of organic materials Expired GB1396469A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1364672A CH571466A5 (en) 1972-09-18 1972-09-18

Publications (1)

Publication Number Publication Date
GB1396469A true GB1396469A (en) 1975-06-04

Family

ID=4394151

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4347273A Expired GB1396469A (en) 1972-09-18 1973-09-17 Thiaalkyl substituted phenols and their use in the stabili sation of organic materials

Country Status (9)

Country Link
JP (1) JPS5756514B2 (en)
AT (1) ATA799773A (en)
BE (1) BE804912A (en)
CA (1) CA1017355A (en)
CH (1) CH571466A5 (en)
DE (1) DE2346458C2 (en)
FR (1) FR2200260B1 (en)
GB (1) GB1396469A (en)
NL (1) NL7312715A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145658A1 (en) * 1983-11-21 1985-06-19 Ciba-Geigy Ag Amides of hydroxyphenylalkylthio-alkane-carboxylic acids
EP0174277A1 (en) * 1984-09-03 1986-03-12 Ciba-Geigy Ag Anti-oxidant compositons for organic material
EP0473549A1 (en) * 1990-08-28 1992-03-04 Ciba-Geigy Ag Sulfoxides of alkylthiomethylphenols
US5167846A (en) * 1990-02-05 1992-12-01 Ciba-Geigy Corporation Sulfoxides of bisthiomethylated and tristhiomethylated phenols
US8258217B2 (en) 2006-09-07 2012-09-04 BASF SE Ludwigshafen Perfluoroalkyl substituted phenol derivatives as surface modifiers

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2659406A1 (en) * 1976-12-29 1978-07-13 Goodyear Tire & Rubber Phenolic antioxidants esp. for clear polymers - esp. polypropylene and polyethylene; also useful as chain transfer agents
JP2003327669A (en) 2002-05-13 2003-11-19 Hitachi Chem Co Ltd Epoxy resin composition and adhesive

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL263103A (en) * 1961-03-30
NL284832A (en) * 1961-10-30
US3285855A (en) * 1965-03-11 1966-11-15 Geigy Chem Corp Stabilization of organic material with esters containing an alkylhydroxy-phenyl group
DE1288604B (en) * 1966-08-18 1969-02-06 Advance Prod Gmbh Stabilization of organic substances against decomposition by oxygen in the heat
US3546272A (en) * 1966-12-27 1970-12-08 Nat Distillers Chem Corp Pentaerythritoltetrakis-(3,5-di-t-butyl-4-hydroxy-benzylthioacetate)
US3504012A (en) * 1967-04-07 1970-03-31 Nat Distillers Chem Corp Hydroxyethyl-beta-(3,5-di-t-butyl-4-hydroxy benzylthio) alkanoate
US3457286A (en) * 1967-12-01 1969-07-22 Geigy Chem Corp Organic esters containing an alkylhydroxyphenyl group
GB1206262A (en) * 1968-02-15 1970-09-23 American Cyanamid Co Hindered phenol sulfides
US3699152A (en) * 1969-12-10 1972-10-17 Carlisle Chemical Works Sulfur containing esters of substituted hydroxyphenyl-alkanoic acids

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0145658A1 (en) * 1983-11-21 1985-06-19 Ciba-Geigy Ag Amides of hydroxyphenylalkylthio-alkane-carboxylic acids
EP0174277A1 (en) * 1984-09-03 1986-03-12 Ciba-Geigy Ag Anti-oxidant compositons for organic material
US5167846A (en) * 1990-02-05 1992-12-01 Ciba-Geigy Corporation Sulfoxides of bisthiomethylated and tristhiomethylated phenols
EP0473549A1 (en) * 1990-08-28 1992-03-04 Ciba-Geigy Ag Sulfoxides of alkylthiomethylphenols
US5258433A (en) * 1990-08-28 1993-11-02 Ciba-Geigy Corporation Sulfoxides of alkylthiomethylphenols
US8258217B2 (en) 2006-09-07 2012-09-04 BASF SE Ludwigshafen Perfluoroalkyl substituted phenol derivatives as surface modifiers

Also Published As

Publication number Publication date
FR2200260B1 (en) 1977-03-11
FR2200260A1 (en) 1974-04-19
NL7312715A (en) 1974-03-20
DE2346458A1 (en) 1974-04-11
DE2346458C2 (en) 1986-07-31
JPS5756514B2 (en) 1982-11-30
CA1017355A (en) 1977-09-13
CH571466A5 (en) 1976-01-15
JPS4970879A (en) 1974-07-09
ATA799773A (en) 1975-04-15
BE804912A (en) 1974-03-18

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee