JPS6054300B2 - 置換ホルムアミジン類の製造方法 - Google Patents
置換ホルムアミジン類の製造方法Info
- Publication number
- JPS6054300B2 JPS6054300B2 JP50046946A JP4694675A JPS6054300B2 JP S6054300 B2 JPS6054300 B2 JP S6054300B2 JP 50046946 A JP50046946 A JP 50046946A JP 4694675 A JP4694675 A JP 4694675A JP S6054300 B2 JPS6054300 B2 JP S6054300B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen
- defined above
- alkyl group
- 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
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
- -1 Ethyl-(4-ethoxycarbonylphenyl)formimidate Ethyl 4-aminobenzoate Chemical compound 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- QHDDNVUKHNJOLQ-UHFFFAOYSA-N ethyl 4-(ethoxymethylideneamino)benzoate Chemical compound CCOC=NC1=CC=C(C(=O)OCC)C=C1 QHDDNVUKHNJOLQ-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940064734 aminobenzoate Drugs 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- WQBRUSQHYBTUNK-UHFFFAOYSA-N butyl 4-(methylamino)benzoate Chemical compound CCCCOC(=O)C1=CC=C(NC)C=C1 WQBRUSQHYBTUNK-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 238000006303 photolysis reaction Methods 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- KNZWULOUXYKBLH-UHFFFAOYSA-N 2-methoxy-n-methylaniline Chemical compound CNC1=CC=CC=C1OC KNZWULOUXYKBLH-UHFFFAOYSA-N 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- IUWVALYLNVXWKX-UHFFFAOYSA-N butamben Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1 IUWVALYLNVXWKX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- XXNAVWORVSFFAD-UHFFFAOYSA-N ethyl 4-formamidobenzoate Chemical compound CCOC(=O)C1=CC=C(NC=O)C=C1 XXNAVWORVSFFAD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 238000010137 moulding (plastic) Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GCULWAWIZUGXTO-UHFFFAOYSA-N n-octylaniline Chemical compound CCCCCCCCNC1=CC=CC=C1 GCULWAWIZUGXTO-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/462,051 US4021471A (en) | 1974-04-18 | 1974-04-18 | Formamidines useful as ultraviolet light absorbers |
| US462051 | 1974-04-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50148323A JPS50148323A (US07655688-20100202-C00010.png) | 1975-11-27 |
| JPS6054300B2 true JPS6054300B2 (ja) | 1985-11-29 |
Family
ID=23834999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50046946A Expired JPS6054300B2 (ja) | 1974-04-18 | 1975-04-17 | 置換ホルムアミジン類の製造方法 |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003504521A (ja) * | 1999-07-02 | 2003-02-04 | コーロン インダストリーズ インク | ポリウレタンウレア弾性繊維およびその製造方法 |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085062A (en) * | 1976-11-24 | 1978-04-18 | Givaudan Corporation | N,N'-bis-aromaticformamidines useful as sunscreening agents |
| US4216335A (en) * | 1977-03-02 | 1980-08-05 | E. R. Squibb & Sons, Inc. | Azo methine containing compounds |
| JPS6169849A (ja) * | 1984-09-14 | 1986-04-10 | Mitsubishi Gas Chem Co Inc | 熱安定性にすぐれたポリフエニレンエ−テル系樹脂組成物 |
| IT1213028B (it) * | 1986-01-30 | 1989-12-07 | Ciba Geigy Spa | Composti piperidinici atti all'impiego come stabilizzanti per polimeri sintetici. |
| IT1204389B (it) * | 1986-06-16 | 1989-03-01 | Ciba Geigy Spa | Derivati triazinici di piperidinilammidine atti all'impiego come stabilizzanti per polimeri sintetici |
| US4839405A (en) * | 1986-07-08 | 1989-06-13 | Plasticolors, Inc. | Ultraviolet stabilizer compositions, stabilized organic materials, and methods |
| US4721531A (en) * | 1986-07-08 | 1988-01-26 | Plasticolors, Inc. | Pigment dispersions exhibiting improved compatibility in polyurethane systems |
| US4872877A (en) * | 1987-03-17 | 1989-10-10 | Dennis T. Grendahl | Intraocular lens with ultraviolet screening agent |
| EP0302527A3 (de) * | 1987-08-07 | 1990-08-22 | Fomagisomer Kunststoffe Gmbh | Formkörper aus Polyurethankunststoff mit Stabilisierungsmitteln, sowie Verfahren und Mittel zu seiner Herstellung |
| US5011628A (en) * | 1988-06-15 | 1991-04-30 | Givaudan Corporation | N,N'-diarylbenzamidines useful as ultraviolet light absorbers |
| DE3916494A1 (de) * | 1989-05-20 | 1990-11-22 | Basf Ag | Heterocyclische amidinderivate |
| US5243055A (en) * | 1990-12-19 | 1993-09-07 | Givaudan Corporation | Heterocyclic formamidines useful as ultraviolet light absorbers |
| KR100292812B1 (ko) * | 1998-07-23 | 2001-09-17 | 최병일 | 자외선차단제용포름아미딘의제조방법 |
| JP4841746B2 (ja) * | 2001-05-22 | 2011-12-21 | 電気化学工業株式会社 | ラテックス組成物 |
| WO2002085977A1 (fr) * | 2001-04-20 | 2002-10-31 | Denki Kagaku Kogyo Kabushiki Kaisha | Composition de latex |
| US20040167255A1 (en) * | 2003-01-14 | 2004-08-26 | Everlight Usa, Inc. | Stabilizer composition |
| KR100562428B1 (ko) * | 2004-05-27 | 2006-03-17 | 주식회사 지코 | 벤질포름아미딘 화합물 |
| CN101481331B (zh) * | 2009-01-20 | 2013-02-13 | 常州市阳光药业有限公司 | N，n’-二(4-乙氧基羰基苯基)-n’-苄基甲脒的制备方法 |
| CN101481330B (zh) * | 2009-01-20 | 2012-06-20 | 常州市阳光药业有限公司 | *-(4-乙氧基羰基苯基)-*＇-甲基-*＇-苯基甲脒的制备方法 |
| CN101838222B (zh) * | 2010-04-24 | 2013-10-09 | 遵义市倍缘化工有限责任公司 | N-(4-乙氧基羰基苯基)-n’-乙基-n’-苯基甲脒的制备方法 |
| CN102060734B (zh) * | 2011-01-14 | 2015-05-20 | 江苏尚莱特医药化工材料有限公司 | N-(4-乙氧基羰基苯基)-n'-甲基-n'-苯基甲脒的制备方法 |
| CN105315168B (zh) * | 2015-11-27 | 2017-09-15 | 常州永和精细化学有限公司 | N‑(4‑乙氧基羰基苯基)‑n’‑甲基‑n’‑苯基甲脒中间体的绿色制备工艺 |
| CN106431990B (zh) * | 2016-10-10 | 2018-09-07 | 中昊(大连)化工研究设计院有限公司 | N-（4-乙氧基羰基苯基）-n’-甲基-n’-苯基甲脒的制备方法 |
| TWI633079B (zh) * | 2017-06-12 | 2018-08-21 | 和新化學工業股份有限公司 | 紫外線吸收劑及具有該紫外線吸收劑之塑膠製品 |
| CN113480451A (zh) * | 2021-08-04 | 2021-10-08 | 天津利安隆新材料股份有限公司 | 脒类紫外线吸收剂、其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL30281A (en) * | 1967-07-11 | 1971-12-29 | Chinoin Gyogyszer Es Vegyeszet | Amidine history and process for their preparation |
| US3751466A (en) * | 1970-10-12 | 1973-08-07 | Ciba Geigy Corp | N-benzylidene alkylamines |
-
1974
- 1974-04-18 US US05/462,051 patent/US4021471A/en not_active Expired - Lifetime
-
1975
- 1975-04-10 CH CH456675A patent/CH608486A5/xx not_active IP Right Cessation
- 1975-04-10 CH CH855678A patent/CH612923A5/xx not_active IP Right Cessation
- 1975-04-16 CA CA224,721A patent/CA1064514A/en not_active Expired
- 1975-04-16 FR FR7511803A patent/FR2268011B1/fr not_active Expired
- 1975-04-17 NL NLAANVRAGE7504572,A patent/NL184951C/xx not_active IP Right Cessation
- 1975-04-17 GB GB1587975A patent/GB1457385A/en not_active Expired
- 1975-04-17 JP JP50046946A patent/JPS6054300B2/ja not_active Expired
- 1975-04-18 DE DE2517284A patent/DE2517284C2/de not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003504521A (ja) * | 1999-07-02 | 2003-02-04 | コーロン インダストリーズ インク | ポリウレタンウレア弾性繊維およびその製造方法 |
| JP4657548B2 (ja) * | 1999-07-02 | 2011-03-23 | コーロン インダストリーズ インク | ポリウレタンウレア弾性繊維およびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL184951C (nl) | 1989-12-18 |
| NL184951B (nl) | 1989-07-17 |
| NL7504572A (nl) | 1975-10-21 |
| US4021471A (en) | 1977-05-03 |
| GB1457385A (en) | 1976-12-01 |
| JPS50148323A (US07655688-20100202-C00010.png) | 1975-11-27 |
| CH612923A5 (US07655688-20100202-C00010.png) | 1979-08-31 |
| CA1064514A (en) | 1979-10-16 |
| FR2268011A1 (US07655688-20100202-C00010.png) | 1975-11-14 |
| CH608486A5 (US07655688-20100202-C00010.png) | 1979-01-15 |
| FR2268011B1 (US07655688-20100202-C00010.png) | 1978-09-01 |
| DE2517284A1 (de) | 1975-11-06 |
| DE2517284C2 (de) | 1985-06-27 |
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