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GB1103144A - Esters containing an alkylhydroxyphenyl group and the stabilisation of organic material therewith - Google Patents

Esters containing an alkylhydroxyphenyl group and the stabilisation of organic material therewith

Info

Publication number
GB1103144A
GB1103144A GB15479/65A GB1547965A GB1103144A GB 1103144 A GB1103144 A GB 1103144A GB 15479/65 A GB15479/65 A GB 15479/65A GB 1547965 A GB1547965 A GB 1547965A GB 1103144 A GB1103144 A GB 1103144A
Authority
GB
United Kingdom
Prior art keywords
hydroxyphenyl
propionate
methylene
tert
butyl
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
GB15479/65A
Inventor
Dexter Martin
John D Spivack
David H Steinberg
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
JR 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1103144A publication Critical patent/GB1103144A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • 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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0028—Carboxylic acids; Their derivates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/402—Castor oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

As agents for stabilizing the materials specified below against deterioration due to oxidation, heat and/or light, use is made of esters of the formula <FORM:1103144/C3/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and z denotes hydrogen or the group <FORM:1103144/C3/2> (see Division C2). Specific esters described are n-propyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert. - butyl - hydroxyphenyl)propionate], ethy 1,1,1 - tris[methylene - 3 - (3,5 - di - tert.- butyl - 4 - hydroxyphenyl)propionate] and tetra[methylene - 3 - (3,5 - di - tert.- butyl - 4 - hydroxyphenyl propionate] - methane. The specified materials are (1) polymers or copolymers of vinyl halides, a number of copolymeric compounds being mentioned, (2) polyolefines, e.g. polyethylene, polypropylene, polybutylene and polyisoprene, (3) polyurethanes, (4) polyamides, e.g. polyhexamethylene adipamide, (5) polyesters, e.g. polymethylene terephthalates, (6) polycarbonates, (7) polyacetals, (8) polystyrene, (9) polyethylene oxide, and (10) copolymers of butadiene and styrene and (or) acrylonitrile. A comparative example of the treatment of polypropylene is given.ALSO:As agents for stabilizing the materials specified below against deterioration due to oxidation, heat and (or) light, use is made of esters of the formula <FORM:1103144/C4-C5/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and z denotes hydrogen or the group <FORM:1103144/C4-C5/2> (see Division C2). Specific esters described are n - propyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate], ethyl 1,1,1 - tris[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate] and tetra[methylene - 3 - (3,5 - di - tert - butyl - 4 - hydroxyphenyl)propionate] - methane. The specified materials are (1) animal and vegetable fats and oils, a number of which are specified; (2) hydrocarbons, including gasoline and fuel oil; (e) waxes; (4) fatty acids; and (5) soaps.ALSO:The invention comprises esters of the formula <FORM:1103144/C2/1> in which R1 and R2 denote branched- or straight-chain alkyl groups of 1-6 carbon atoms, x is 1-6, y is 1 or 2 and Z denotes hydrogen or the group <FORM:1103144/C2/2> The esters are obtainable by reacting an alkane polyol with an acid having a radical of the second formula above, the acid being taken as such or as its anhydride or acid halide. Reference is made also to the manufacture of the esters by transesterification. Examples are given of the preparation of n-propyl 1,1,1-tris [methylene - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate], ethyl 1,1,1-tris [methylene - 3 - (3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate] and tetra[methylene-3-(3,5 - di - tert. - butyl - 4 - hydroxyphenyl) propionate]-methane, and these esters are specifically claimed. The esters are useful for stabilizing organic materials against deterioration due to oxidation, heat or light, and reference is made to the stabilization of lubricating oils of the aliphatic ester type, e.g. di(2-ethylhexyl) azelate or pentaerythritol tetracaproate.
GB15479/65A 1964-04-13 1965-04-12 Esters containing an alkylhydroxyphenyl group and the stabilisation of organic material therewith Expired GB1103144A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US35946064A 1964-04-13 1964-04-13

Publications (1)

Publication Number Publication Date
GB1103144A true GB1103144A (en) 1968-02-14

Family

ID=23413882

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15479/65A Expired GB1103144A (en) 1964-04-13 1965-04-12 Esters containing an alkylhydroxyphenyl group and the stabilisation of organic material therewith

Country Status (8)

Country Link
AT (1) AT257952B (en)
BE (1) BE662372A (en)
CH (1) CH455278A (en)
DE (1) DE1493779C3 (en)
ES (1) ES311741A1 (en)
FR (1) FR1448811A (en)
GB (1) GB1103144A (en)
NL (1) NL145525B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0032459A1 (en) * 1980-01-14 1981-07-22 Mitsui Petrochemical Industries, Ltd. Tetrakis(3-(3.5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl)methane having a novel crystal structure, process for its production and its use as an antioxidant
EP0245204A1 (en) * 1986-05-05 1987-11-11 Ciba-Geigy Ag Process for the photochemical stabilization of undyed and dyed fibrous polyamide material and its mixture with other fibres
WO1989005789A1 (en) * 1987-12-14 1989-06-29 Nauchno-Issledovatelsky Institut Khimikatov Dlya P Method of extracting pentaerythryl-tetrakis-[3-(3,5-ditert. butyl-4-oxyphenyl)propionate] from the reaction mass obtained during synthesis of said product
US4874391A (en) * 1986-07-29 1989-10-17 Ciba-Geigy Corporation Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer
US6296677B1 (en) 1997-02-03 2001-10-02 Ciba Specialty Chemicals Corporation Liquid polyfunctional additives for improved fuel lubricity

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0032459A1 (en) * 1980-01-14 1981-07-22 Mitsui Petrochemical Industries, Ltd. Tetrakis(3-(3.5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl)methane having a novel crystal structure, process for its production and its use as an antioxidant
EP0245204A1 (en) * 1986-05-05 1987-11-11 Ciba-Geigy Ag Process for the photochemical stabilization of undyed and dyed fibrous polyamide material and its mixture with other fibres
US4775386A (en) * 1986-05-05 1988-10-04 Ciba-Geigy Corporation Process for photochemical stabilization of undyed and dyed polyamide fibre material and blends thereof with other fibres: copper complex and light stabilizer treatment
US4874391A (en) * 1986-07-29 1989-10-17 Ciba-Geigy Corporation Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer
WO1989005789A1 (en) * 1987-12-14 1989-06-29 Nauchno-Issledovatelsky Institut Khimikatov Dlya P Method of extracting pentaerythryl-tetrakis-[3-(3,5-ditert. butyl-4-oxyphenyl)propionate] from the reaction mass obtained during synthesis of said product
US6296677B1 (en) 1997-02-03 2001-10-02 Ciba Specialty Chemicals Corporation Liquid polyfunctional additives for improved fuel lubricity

Also Published As

Publication number Publication date
CH455278A (en) 1968-06-28
DE1493779A1 (en) 1972-04-20
DE1493779B2 (en) 1973-07-05
DE1793588B2 (en) 1973-01-11
ES311741A1 (en) 1965-12-16
AT257952B (en) 1967-11-10
DE1793588A1 (en) 1972-06-08
DE1493779C3 (en) 1974-02-07
FR1448811A (en) 1966-08-12
NL145525B (en) 1975-04-15
NL6504638A (en) 1965-10-14
BE662372A (en) 1965-10-12

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