DE2527402B2 - Verwendung von Phenolderivaten zur Inhibierung einer Zersetzung von zersetzbaren polymeren und öligen Substanzen - Google Patents
Verwendung von Phenolderivaten zur Inhibierung einer Zersetzung von zersetzbaren polymeren und öligen SubstanzenInfo
- Publication number
- DE2527402B2 DE2527402B2 DE2527402A DE2527402A DE2527402B2 DE 2527402 B2 DE2527402 B2 DE 2527402B2 DE 2527402 A DE2527402 A DE 2527402A DE 2527402 A DE2527402 A DE 2527402A DE 2527402 B2 DE2527402 B2 DE 2527402B2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- phenol derivatives
- decomposition
- cresol
- decomposable
- 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.)
- Withdrawn
Links
- 238000000354 decomposition reaction Methods 0.000 title claims description 25
- 150000002989 phenols Chemical class 0.000 title claims description 22
- 239000000126 substance Substances 0.000 title claims description 11
- 229920001971 elastomer Polymers 0.000 claims description 27
- 239000005060 rubber Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 15
- 230000000052 comparative effect Effects 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 12
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 11
- 230000015556 catabolic process Effects 0.000 claims description 10
- 238000006731 degradation reaction Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 238000002845 discoloration Methods 0.000 claims description 6
- -1 amine compounds Chemical class 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 claims 2
- 239000000499 gel Substances 0.000 claims 2
- 239000004033 plastic Substances 0.000 claims 2
- 229920003023 plastic Polymers 0.000 claims 2
- 150000003568 thioethers Chemical class 0.000 claims 2
- YSMALBAKHKOBAN-UHFFFAOYSA-N 2,3-dicyclohexyl-4-methylphenol Chemical class C1CCCCC1C=1C(C)=CC=C(O)C=1C1CCCCC1 YSMALBAKHKOBAN-UHFFFAOYSA-N 0.000 claims 1
- 244000043261 Hevea brasiliensis Species 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229920003052 natural elastomer Polymers 0.000 claims 1
- 229920001194 natural rubber Polymers 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 230000000704 physical effect Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920003051 synthetic elastomer Polymers 0.000 claims 1
- 239000005061 synthetic rubber Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 10
- 229920000126 latex Polymers 0.000 description 10
- 239000004816 latex Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 210000000540 fraction c Anatomy 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 210000002196 fr. b Anatomy 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 210000003918 fraction a Anatomy 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GOXKGNBQJTYZSE-UHFFFAOYSA-N 2,5-dicyclopentyl-4-methylphenol Chemical group OC=1C=C(C2CCCC2)C(C)=CC=1C1CCCC1 GOXKGNBQJTYZSE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- UMVQHMLKVSITHH-UHFFFAOYSA-N 2,5-dicyclohexyl-4-methylphenol Chemical compound OC=1C=C(C2CCCCC2)C(C)=CC=1C1CCCCC1 UMVQHMLKVSITHH-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XCACPHZINVMTGV-UHFFFAOYSA-N 3,5-dicyclohexyl-4-methylphenol Chemical compound CC1=C(C2CCCCC2)C=C(O)C=C1C1CCCCC1 XCACPHZINVMTGV-UHFFFAOYSA-N 0.000 description 1
- PDKSSHFZTRPHCP-UHFFFAOYSA-N 3,5-dicyclopentyl-4-methylphenol Chemical compound CC1=C(C2CCCC2)C=C(O)C=C1C1CCCC1 PDKSSHFZTRPHCP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000000214 vapour pressure osmometry Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- C09K13/00—Etching, surface-brightening or pickling compositions
- C09K13/04—Etching, surface-brightening or pickling compositions containing an inorganic acid
- C09K13/08—Etching, surface-brightening or pickling compositions containing an inorganic acid containing a fluorine compound
-
- 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
- C07C39/17—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 containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49069171A JPS511451A (enExample) | 1974-06-19 | 1974-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2527402A1 DE2527402A1 (de) | 1976-01-08 |
| DE2527402B2 true DE2527402B2 (de) | 1979-08-30 |
Family
ID=13394989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2527402A Withdrawn DE2527402B2 (de) | 1974-06-19 | 1975-06-19 | Verwendung von Phenolderivaten zur Inhibierung einer Zersetzung von zersetzbaren polymeren und öligen Substanzen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4008284A (enExample) |
| JP (1) | JPS511451A (enExample) |
| DE (1) | DE2527402B2 (enExample) |
| FR (1) | FR2275432A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5935949B2 (ja) * | 1975-12-18 | 1984-08-31 | ニツポンゼオン カブシキガイシヤ | レツカボウシザイ |
| US4101431A (en) * | 1977-05-12 | 1978-07-18 | Texaco Inc. | Turbine lubricant |
| JP6138115B2 (ja) * | 2012-03-30 | 2017-05-31 | 本州化学工業株式会社 | トリスフェノール類の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2864868A (en) * | 1958-12-16 | Cyclopentenyl phenols and method | ||
| US2246762A (en) * | 1934-12-22 | 1941-06-24 | Unichem Chemikalien Handels A | Method for condensation |
| US2581907A (en) * | 1946-03-09 | 1952-01-08 | Firestone Tire & Rubber Co | Rubbery diolefinic polymers containing as antioxidant a mixture of antimony oxide and a 2, 4, 6 trihydrocarbon substituted phenol |
| US2567848A (en) * | 1947-08-01 | 1951-09-11 | Shell Dev | Alkylation of phenolic compounds with olefins |
| US2802881A (en) * | 1955-05-11 | 1957-08-13 | Dow Chemical Co | Halo-dicyclohexyl-phenols |
| US2993074A (en) * | 1958-02-10 | 1961-07-18 | Hooker Chemical Corp | Process for the production of phenols by decomposition of aralkyl hydroperoxides |
| US3012049A (en) * | 1958-09-09 | 1961-12-05 | Us Rubber Co | Ester-interchange catalysts |
| US3093587A (en) * | 1960-05-17 | 1963-06-11 | Ethyl Corp | Organic material containing cyclohexyl phenols as antioxidants |
| US3444246A (en) * | 1961-06-01 | 1969-05-13 | Hooker Chemical Corp | 3,5-dicyclohexyl phenol |
-
1974
- 1974-06-19 JP JP49069171A patent/JPS511451A/ja active Pending
-
1975
- 1975-06-09 US US05/584,931 patent/US4008284A/en not_active Expired - Lifetime
- 1975-06-19 FR FR7519202A patent/FR2275432A1/fr active Granted
- 1975-06-19 DE DE2527402A patent/DE2527402B2/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US4008284A (en) | 1977-02-15 |
| FR2275432B1 (enExample) | 1980-03-28 |
| DE2527402A1 (de) | 1976-01-08 |
| FR2275432A1 (fr) | 1976-01-16 |
| JPS511451A (enExample) | 1976-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8239 | Disposal/non-payment of the annual fee |