DE2517284C2 - Substituierte Formamidine und deren Verwendung - Google Patents
Substituierte Formamidine und deren VerwendungInfo
- Publication number
- DE2517284C2 DE2517284C2 DE2517284A DE2517284A DE2517284C2 DE 2517284 C2 DE2517284 C2 DE 2517284C2 DE 2517284 A DE2517284 A DE 2517284A DE 2517284 A DE2517284 A DE 2517284A DE 2517284 C2 DE2517284 C2 DE 2517284C2
- Authority
- DE
- Germany
- Prior art keywords
- ethoxycarbonylphenyl
- methyl
- phenylformamidine
- formamidine
- methylformamidine
- 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 26
- -1 4-Ethoxycarbonylphenyl Chemical group 0.000 claims description 18
- WGRDGYQXGAVZRE-UHFFFAOYSA-N ethyl 4-[(4-butoxycarbonyl-n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1N(C)C=NC1=CC=C(C(=O)OCC)C=C1 WGRDGYQXGAVZRE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- SJYQTTWGAWDSNE-UHFFFAOYSA-N ethyl 4-[(2-methoxy-n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C)C1=CC=CC=C1OC SJYQTTWGAWDSNE-UHFFFAOYSA-N 0.000 claims description 2
- UDNPARSFHLMMQF-UHFFFAOYSA-N ethyl 4-[(3,4-dichloro-n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C)C1=CC=C(Cl)C(Cl)=C1 UDNPARSFHLMMQF-UHFFFAOYSA-N 0.000 claims description 2
- QQQSJXMJXHPQRT-UHFFFAOYSA-N ethyl 2-methoxy-4-[(N-methylanilino)methylideneamino]benzoate Chemical compound C(C)OC(=O)C1=C(C=C(C=C1)N=CN(C1=CC=CC=C1)C)OC QQQSJXMJXHPQRT-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000002845 discoloration Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000002360 preparation method 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
- YKSCOZXTXACAIX-UHFFFAOYSA-N n'-phenylmethanimidamide Chemical compound N=CNC1=CC=CC=C1 YKSCOZXTXACAIX-UHFFFAOYSA-N 0.000 description 6
- QHDDNVUKHNJOLQ-UHFFFAOYSA-N ethyl 4-(ethoxymethylideneamino)benzoate Chemical compound CCOC=NC1=CC=C(C(=O)OCC)C=C1 QHDDNVUKHNJOLQ-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
- 238000001782 photodegradation Methods 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-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
- 150000001448 anilines Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000001066 destructive effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 229940064734 aminobenzoate Drugs 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- IUWVALYLNVXWKX-UHFFFAOYSA-N butamben Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1 IUWVALYLNVXWKX-UHFFFAOYSA-N 0.000 description 2
- ADQAUJINXGBRLX-UHFFFAOYSA-N butyl 4-[(n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1N=CN(C)C1=CC=CC=C1 ADQAUJINXGBRLX-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- VEJNALIVSLRUGG-UHFFFAOYSA-N ethyl 4-[(n-octylanilino)methylideneamino]benzoate Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C=NC1=CC=C(C(=O)OCC)C=C1 VEJNALIVSLRUGG-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NVFPHKSEIQNWCE-UHFFFAOYSA-N n'-methylmethanimidamide Chemical compound CNC=N NVFPHKSEIQNWCE-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000526 short-path distillation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 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
- KNZWULOUXYKBLH-UHFFFAOYSA-N 2-methoxy-n-methylaniline Chemical compound CNC1=CC=CC=C1OC KNZWULOUXYKBLH-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- WQBRUSQHYBTUNK-UHFFFAOYSA-N butyl 4-(methylamino)benzoate Chemical compound CCCCOC(=O)C1=CC=C(NC)C=C1 WQBRUSQHYBTUNK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ITLCGBBKMUHGAB-UHFFFAOYSA-N ethyl 4-[(n-butylanilino)methylideneamino]benzoate Chemical compound C=1C=CC=CC=1N(CCCC)C=NC1=CC=C(C(=O)OCC)C=C1 ITLCGBBKMUHGAB-UHFFFAOYSA-N 0.000 description 1
- GNGYPJUKIKDJQT-UHFFFAOYSA-N ethyl 4-[(n-methylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C)C1=CC=CC=C1 GNGYPJUKIKDJQT-UHFFFAOYSA-N 0.000 description 1
- NUZXPIAFFMSGDK-UHFFFAOYSA-N ethyl 4-[(n-phenylanilino)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C=1C=CC=CC=1)C1=CC=CC=C1 NUZXPIAFFMSGDK-UHFFFAOYSA-N 0.000 description 1
- QZUHCYNHKPKZHM-UHFFFAOYSA-N ethyl 4-[[4-(dimethylamino)-n-methylanilino]methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CN(C)C1=CC=C(N(C)C)C=C1 QZUHCYNHKPKZHM-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UVIRXWRITCUPDJ-UHFFFAOYSA-N methyl 2-hydroxy-4-[(n-methylanilino)methylideneamino]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1N=CN(C)C1=CC=CC=C1 UVIRXWRITCUPDJ-UHFFFAOYSA-N 0.000 description 1
- DMLCOBJFBCTPGR-UHFFFAOYSA-N methyl 4-(ethoxymethylideneamino)-2-hydroxybenzoate Chemical compound CCOC=NC1=CC=C(C(=O)OC)C(O)=C1 DMLCOBJFBCTPGR-UHFFFAOYSA-N 0.000 description 1
- PANBFSGJYKYTNM-UHFFFAOYSA-N n'-phenylethanimidamide Chemical compound CC(N)=NC1=CC=CC=C1 PANBFSGJYKYTNM-UHFFFAOYSA-N 0.000 description 1
- HTCKXHQQEOBPAW-UHFFFAOYSA-N n-methyl-n-phenylmethanimidamide Chemical compound N=CN(C)C1=CC=CC=C1 HTCKXHQQEOBPAW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002994 raw material 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
- 239000004753 textile Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical class COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/462,051 US4021471A (en) | 1974-04-18 | 1974-04-18 | Formamidines useful as ultraviolet light absorbers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2517284A1 DE2517284A1 (de) | 1975-11-06 |
| DE2517284C2 true DE2517284C2 (de) | 1985-06-27 |
Family
ID=23834999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2517284A Expired DE2517284C2 (de) | 1974-04-18 | 1975-04-18 | Substituierte Formamidine und deren Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4021471A (en, 2012) |
| JP (1) | JPS6054300B2 (en, 2012) |
| CA (1) | CA1064514A (en, 2012) |
| CH (2) | CH608486A5 (en, 2012) |
| DE (1) | DE2517284C2 (en, 2012) |
| FR (1) | FR2268011B1 (en, 2012) |
| GB (1) | GB1457385A (en, 2012) |
| NL (1) | NL184951C (en, 2012) |
Families Citing this family (27)
| 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 |
| ES2009721A4 (es) * | 1987-08-07 | 1989-10-16 | Fomagisomer Kunststoffe Gmbh | Cuerpos de moldeo de poliuretano sintetico con agentes estabilizantes, asi como el metodo y agente para su produccion |
| 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 |
| US6545074B1 (en) * | 1999-07-02 | 2003-04-08 | Kolon Industries, Inc. | Polyurethaneures elastic fiber, and a process of preparing the same |
| TW584650B (en) * | 2001-04-20 | 2004-04-21 | Denki Kagaku Kogyo Kk | Latex composition |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| US20220220068A1 (en) * | 2019-05-23 | 2022-07-14 | Corteva Agriscience Llc | Fungicidal aryl amidines |
| 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 JP JP50046946A patent/JPS6054300B2/ja not_active Expired
- 1975-04-17 GB GB1587975A patent/GB1457385A/en not_active Expired
- 1975-04-17 NL NLAANVRAGE7504572,A patent/NL184951C/xx not_active IP Right Cessation
- 1975-04-18 DE DE2517284A patent/DE2517284C2/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50148323A (en, 2012) | 1975-11-27 |
| JPS6054300B2 (ja) | 1985-11-29 |
| NL184951C (nl) | 1989-12-18 |
| CA1064514A (en) | 1979-10-16 |
| NL184951B (nl) | 1989-07-17 |
| CH608486A5 (en, 2012) | 1979-01-15 |
| FR2268011A1 (en, 2012) | 1975-11-14 |
| GB1457385A (en) | 1976-12-01 |
| US4021471A (en) | 1977-05-03 |
| FR2268011B1 (en, 2012) | 1978-09-01 |
| CH612923A5 (en, 2012) | 1979-08-31 |
| DE2517284A1 (de) | 1975-11-06 |
| NL7504572A (nl) | 1975-10-21 |
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