IE35597L - Synthetic ester oils; lubricants - Google Patents
Synthetic ester oils; lubricantsInfo
- Publication number
- IE35597L IE35597L IE711131A IE113171A IE35597L IE 35597 L IE35597 L IE 35597L IE 711131 A IE711131 A IE 711131A IE 113171 A IE113171 A IE 113171A IE 35597 L IE35597 L IE 35597L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- weight
- acids
- mixture
- ester oils
- Prior art date
Links
- 239000010696 ester oil Substances 0.000 title abstract 4
- 239000000314 lubricant Substances 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 6
- 150000007513 acids Chemical class 0.000 abstract 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- 238000000605 extraction Methods 0.000 abstract 3
- 229920005862 polyol Polymers 0.000 abstract 3
- 150000003077 polyols Chemical class 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 2
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 abstract 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 150000002311 glutaric acids Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- 229940005605 valeric acid Drugs 0.000 abstract 1
Classifications
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—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
- 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
- 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
- C10M2207/288—Partial esters containing free carboxyl groups
-
- 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
- C10M2209/112—Complex polyesters having dihydric acid centres
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
1356405 Synthetic ester oils INVENTA AG 5 Aug 1971 [7 Sept 1970] 36859/71 Heading C2C [Also in Division C5] Novel ester oils in which the alcohol moieties comprise moieties of a C 2 -C 20 polyol containing primary hydroxy groups and/or of a branched chain C 3 -C 18 monoalcohol and the acid moieties comprise moieties of acids obtained in admixture as by-products in the oxidation of a C 6 - C 12 cycloalkane by means of a gas comprising molecular oxygen to give a cycloalkanol/cycloalkanone mixture as predominant reaction product, are synthesized by an esterification process wherein the alcoholic starting material comprises an aforesaid polyol and/or branched monoalcohol and the acidic starting material comprises the aforesaid mixture of acids or by an appropriate transesterification. A typical mixture of acids obtained by oxidation of cyclohexane using air and, for example, cobalt naphthenate as catalyst, followed by extraction with aqueous alkali, acidification and extraction of the liberated acids with cyclohexane, comprises 5-45% by weight of butyric acid, 40-80% by weight of valeric acid and 15- 55% by weight of caproic acid. If, however, the final extraction is carried out with methyl ethyl ketone, then the mixture of acids obtained comprises 40-60% by weight of the above mixture together with 20-40% by weight of hydroxycaproic acid and 20-40% by weight of a mixture of dicarboxylic acids comprising 65-85% by weight of adipic acid and lesser amounts of succinic and glutaric acids. Preferred polyols are polyethylene glycol, dimethylpropanediol, the polyethylene glycol 200 di-ester of decanedicarboxylic acid, trimethylol propane and pentaerythritol and the preferred branched chain C 3 -C 18 monohydric alcohol is 2-ethylhexanol. The acid starting material may also comprise additional monocarboxylic acids and/ or C 6 -C 12 dicarboxylic acids, e.g. decanedicarboxylic acid. The synthetic ester oils may be used as lubricating oils, e.g. mixed with either an antioxidant or a mineral oil.
[GB1356405A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1332870 | 1970-09-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35597L true IE35597L (en) | 1972-03-07 |
| IE35597B1 IE35597B1 (en) | 1976-03-31 |
Family
ID=4391469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1131/71A IE35597B1 (en) | 1970-09-07 | 1971-09-06 | Synthesis of ester oils |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5035991B1 (en) |
| KR (1) | KR790000105B1 (en) |
| AT (1) | AT312779B (en) |
| BE (1) | BE772225A (en) |
| BG (1) | BG19191A3 (en) |
| CA (1) | CA954850A (en) |
| CH (1) | CH545762A (en) |
| CS (1) | CS166032B2 (en) |
| DE (1) | DE2144252C3 (en) |
| DK (1) | DK144036C (en) |
| ES (1) | ES394826A1 (en) |
| FR (1) | FR2106349B1 (en) |
| GB (1) | GB1356405A (en) |
| HU (1) | HU172801B (en) |
| IE (1) | IE35597B1 (en) |
| NL (1) | NL152598B (en) |
| PL (1) | PL87254B1 (en) |
| RO (1) | RO70130A (en) |
| SU (1) | SU561519A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014047043A1 (en) * | 2012-09-21 | 2014-03-27 | Invista North America S.A R.L. | Materials comprising nvr polyols |
-
1970
- 1970-09-07 CH CH1332870A patent/CH545762A/xx not_active IP Right Cessation
-
1971
- 1971-08-02 RO RO7167871A patent/RO70130A/en unknown
- 1971-08-05 GB GB3685971A patent/GB1356405A/en not_active Expired
- 1971-09-03 DE DE2144252A patent/DE2144252C3/en not_active Expired
- 1971-09-03 CA CA122,070A patent/CA954850A/en not_active Expired
- 1971-09-04 BG BG018506A patent/BG19191A3/en unknown
- 1971-09-06 CS CS6345A patent/CS166032B2/cs unknown
- 1971-09-06 PL PL1971150373A patent/PL87254B1/pl unknown
- 1971-09-06 HU HU71IE00000474A patent/HU172801B/en unknown
- 1971-09-06 KR KR7101256A patent/KR790000105B1/en not_active Expired
- 1971-09-06 NL NL717112233A patent/NL152598B/en not_active IP Right Cessation
- 1971-09-06 FR FR7132145A patent/FR2106349B1/fr not_active Expired
- 1971-09-06 BE BE772225A patent/BE772225A/en unknown
- 1971-09-06 ES ES394826A patent/ES394826A1/en not_active Expired
- 1971-09-06 AT AT772571A patent/AT312779B/en active
- 1971-09-06 JP JP46068823A patent/JPS5035991B1/ja active Pending
- 1971-09-06 IE IE1131/71A patent/IE35597B1/en unknown
- 1971-09-06 DK DK436871A patent/DK144036C/en active
- 1971-12-31 SU SU1732565A patent/SU561519A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2106349A1 (en) | 1972-05-05 |
| FR2106349B1 (en) | 1974-03-15 |
| JPS5035991B1 (en) | 1975-11-20 |
| ES394826A1 (en) | 1974-03-01 |
| IE35597B1 (en) | 1976-03-31 |
| HU172801B (en) | 1978-12-28 |
| SU561519A3 (en) | 1977-06-05 |
| GB1356405A (en) | 1974-06-12 |
| DE2144252C3 (en) | 1979-02-15 |
| DK144036C (en) | 1982-05-03 |
| BE772225A (en) | 1972-01-17 |
| DE2144252A1 (en) | 1972-03-09 |
| NL7112233A (en) | 1972-03-09 |
| RO70130A (en) | 1980-12-30 |
| CA954850A (en) | 1974-09-17 |
| DE2144252B2 (en) | 1978-06-15 |
| KR790000105B1 (en) | 1979-03-15 |
| PL87254B1 (en) | 1976-06-30 |
| CH545762A (en) | 1974-02-15 |
| AT312779B (en) | 1974-01-25 |
| CS166032B2 (en) | 1976-01-29 |
| DK144036B (en) | 1981-11-23 |
| NL152598B (en) | 1977-03-15 |
| BG19191A3 (en) | 1975-04-30 |
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