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 therewithInfo
- 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
Links
- 150000002148 esters Chemical class 0.000 title abstract 10
- 239000011368 organic material Substances 0.000 title abstract 2
- 230000006641 stabilisation Effects 0.000 title abstract 2
- -1 vinyl halides Chemical class 0.000 abstract 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 8
- 239000007983 Tris buffer Substances 0.000 abstract 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 5
- 239000000463 material Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 230000006866 deterioration Effects 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- 230000000087 stabilizing effect Effects 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004743 Polypropylene Substances 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229920001155 polypropylene Polymers 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002302 Nylon 6,6 Polymers 0.000 abstract 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000000295 fuel oil Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920001748 polybutylene Polymers 0.000 abstract 1
- 239000004417 polycarbonate Substances 0.000 abstract 1
- 229920000515 polycarbonate Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- 229920006324 polyoxymethylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 235000019871 vegetable fat Nutrition 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- 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.
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)
| 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 |
-
1965
- 1965-04-08 CH CH496265A patent/CH455278A/en unknown
- 1965-04-12 AT AT336165A patent/AT257952B/en active
- 1965-04-12 DE DE1493779A patent/DE1493779C3/en not_active Expired
- 1965-04-12 BE BE662372A patent/BE662372A/en unknown
- 1965-04-12 GB GB15479/65A patent/GB1103144A/en not_active Expired
- 1965-04-12 ES ES0311741A patent/ES311741A1/en not_active Expired
- 1965-04-12 FR FR12885A patent/FR1448811A/en not_active Expired
- 1965-04-12 NL NL656504638A patent/NL145525B/en not_active IP Right Cessation
Cited By (6)
| 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 |
|---|---|
| DE1793588B2 (en) | 1973-01-11 |
| DE1493779C3 (en) | 1974-02-07 |
| ES311741A1 (en) | 1965-12-16 |
| AT257952B (en) | 1967-11-10 |
| FR1448811A (en) | 1966-08-12 |
| DE1493779A1 (en) | 1972-04-20 |
| DE1793588A1 (en) | 1972-06-08 |
| DE1493779B2 (en) | 1973-07-05 |
| NL6504638A (en) | 1965-10-14 |
| BE662372A (en) | 1965-10-12 |
| CH455278A (en) | 1968-06-28 |
| NL145525B (en) | 1975-04-15 |
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