GB1442133A - 1,5-bis-3,5-hydrocarbyl-4-hydroxyphenyl-pentyl derivatives - Google Patents

1,5-bis-3,5-hydrocarbyl-4-hydroxyphenyl-pentyl derivatives

Info

Publication number
GB1442133A
GB1442133A GB4132473A GB4132473A GB1442133A GB 1442133 A GB1442133 A GB 1442133A GB 4132473 A GB4132473 A GB 4132473A GB 4132473 A GB4132473 A GB 4132473A GB 1442133 A GB1442133 A GB 1442133A
Authority
GB
United Kingdom
Prior art keywords
carbons
attached
pentyl
alkyl
hydrogen
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
GB4132473A
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
Publication of GB1442133A publication Critical patent/GB1442133A/en
Expired legal-status Critical Current

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    • 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
    • C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • C07C49/248—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/1414—Esters of phosphorous acids with arylalkanols
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • 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
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1442133 Phenolic antioxidants UNIROYAL INC 3 Sept 1973 [5 Sept 1972] 41324/73 Heading C3P [Also in Division C2] Polymers are stabilized by adding thereto 1,5 - bis - (3<SP>1</SP>,5<SP>1</SP> - hydrocarbyl - 4<SP>1</SP> - hydroxyphenyl)pentyl derivatives of formula wherein R and R<SP>1</SP> are hydrogen or alkyl having up to 4 carbons each or may be taken together to form a carbocyclic ring or 5 to 7 carbons and including the carbon to which A is attached; R<SP>2</SP> through R<SP>5</SP> are hydrogen, alkyl, cycloalkyl, aryl, aralkyl or alkaryl, each of such hydrocarbyl groups having up to 12 carbons each and, when A is -OH or =O, R and R<SP>1</SP> are only hydrogen or alkyl and at least two of R<SP>2</SP> to R<SP>6</SP> are hydrocarbyl groups having at least 3 carbons each; A is -OH, -OR<SP>6</SP>, -OR<SP>7</SP>, = O, #N, =N-R<SP>7</SP>, PO 3 #, PO 4 #, or R<SP>7</SP> is R<SP>6</SP>, R<SP>6</SP> and R<SP>8</SP> are hydrogen, alkyl of up to 30 carbons, cycloalkyl of 3 to 7 carbons, aryl, aralkyl, alkaryl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl or alkylthioalkyl, the latter, seven radicals having up to 16 carbons each; R<SP>6</SP> and R<SP>7</SP> may be taken together with the nitrogen to which they are attached in to form a heterocylic ring; R<SP>9</SP> is alkylene, oxydialkylene, thiodialkylene or arylene of up to 16 carbons each; m is 1 when A is attached to the same pentyl carbon by a single bond and zero when A is attached to the same pentyl carbon by a double bond; and n is an integer corresponding to the functionality of A except that it is 1 when A is attached to the same pentyl carbon by a double bond. The compounds of the invention are especially effective in combination with dialkyl-3,3<SP>1</SP>-thiodipropionates and triaryl phosphites.
GB4132473A 1972-09-05 1973-09-03 1,5-bis-3,5-hydrocarbyl-4-hydroxyphenyl-pentyl derivatives Expired GB1442133A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US28596972A 1972-09-05 1972-09-05

Publications (1)

Publication Number Publication Date
GB1442133A true GB1442133A (en) 1976-07-07

Family

ID=23096466

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4132473A Expired GB1442133A (en) 1972-09-05 1973-09-03 1,5-bis-3,5-hydrocarbyl-4-hydroxyphenyl-pentyl derivatives

Country Status (12)

Country Link
JP (1) JPS4964633A (en)
AR (1) AR202008A1 (en)
AU (1) AU485682B2 (en)
BE (1) BE804386A (en)
BR (1) BR7306881D0 (en)
CA (1) CA999302A (en)
DE (1) DE2344525A1 (en)
FR (2) FR2197854B1 (en)
GB (1) GB1442133A (en)
IT (1) IT999543B (en)
NL (1) NL7312311A (en)
ZA (1) ZA735912B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4965399A (en) * 1988-08-19 1990-10-23 Eastman Kodak Company 1,5-diaryl-3-pentanol compounds and processes for the preparation thereof
EP0860422A1 (en) * 1997-02-20 1998-08-26 The University of Gajah Mada Derivatives of benzylidene cyclohexanone, benzylidene cyclopentanone, and benzylidene acetone and their synthesis.
CN116284642A (en) * 2023-05-18 2023-06-23 平原倍斯特化工有限公司 Yellowing-resistant isocyanate composition and preparation method thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9210027D0 (en) * 1992-05-09 1992-06-24 Interox Chemicals Ltd Oxidation process
JP6035888B2 (en) * 2012-06-13 2016-11-30 Dic株式会社 Phenol derivative

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3594424A (en) * 1967-11-01 1971-07-20 Goodrich Co B F 2,6-bis(3,5-dialkyl-4-hydroxybenzyl) cycloalkanones
DE2009504A1 (en) * 1970-02-28 1971-09-09 Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen Bisphenol antioxidants for polyolefins

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4965399A (en) * 1988-08-19 1990-10-23 Eastman Kodak Company 1,5-diaryl-3-pentanol compounds and processes for the preparation thereof
EP0860422A1 (en) * 1997-02-20 1998-08-26 The University of Gajah Mada Derivatives of benzylidene cyclohexanone, benzylidene cyclopentanone, and benzylidene acetone and their synthesis.
CN116284642A (en) * 2023-05-18 2023-06-23 平原倍斯特化工有限公司 Yellowing-resistant isocyanate composition and preparation method thereof

Also Published As

Publication number Publication date
AR202008A1 (en) 1975-05-09
JPS4964633A (en) 1974-06-22
CA999302A (en) 1976-11-02
IT999543B (en) 1976-03-10
AU485682B2 (en) 1975-03-06
BE804386A (en) 1974-03-04
FR2197854B1 (en) 1979-05-04
NL7312311A (en) 1974-03-07
FR2303791A1 (en) 1976-10-08
BR7306881D0 (en) 1974-07-18
FR2197854A1 (en) 1974-03-29
ZA735912B (en) 1974-07-31
AU5983073A (en) 1975-03-06
DE2344525A1 (en) 1974-03-14

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Legal Events

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PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee