DE2238734C2 - Bis-benzofuranyl-Verbindungen und deren Verwendung als optische Aufheller - Google Patents
Bis-benzofuranyl-Verbindungen und deren Verwendung als optische AufhellerInfo
- Publication number
- DE2238734C2 DE2238734C2 DE2238734A DE2238734A DE2238734C2 DE 2238734 C2 DE2238734 C2 DE 2238734C2 DE 2238734 A DE2238734 A DE 2238734A DE 2238734 A DE2238734 A DE 2238734A DE 2238734 C2 DE2238734 C2 DE 2238734C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- fabric
- formula
- whiteness
- bis
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 Ci- to Q-alkoxy Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910001413 alkali metal ion Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000004744 fabric Substances 0.000 description 26
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- 239000011368 organic material Substances 0.000 description 4
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001907 coumarones Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
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- 238000000465 moulding Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
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- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 3
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- 238000009987 spinning Methods 0.000 description 3
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- ADDZHRRCUWNSCS-UHFFFAOYSA-N 2-Benzofurancarboxaldehyde Chemical compound C1=CC=C2OC(C=O)=CC2=C1 ADDZHRRCUWNSCS-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 150000001408 amides Chemical class 0.000 description 2
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- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910001919 chlorite Inorganic materials 0.000 description 2
- 229910052619 chlorite group Inorganic materials 0.000 description 2
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
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- 235000011152 sodium sulphate Nutrition 0.000 description 2
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- 239000004753 textile Substances 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- UBJKHRKGYBTDIA-UHFFFAOYSA-N 3-methyl-1-benzofuran-2-carbaldehyde Chemical compound C1=CC=C2C(C)=C(C=O)OC2=C1 UBJKHRKGYBTDIA-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
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- 239000004115 Sodium Silicate Substances 0.000 description 1
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- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
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- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Furan Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1192471A CH568432B5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-08-13 | 1971-08-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2238734A1 DE2238734A1 (de) | 1973-02-22 |
| DE2238734C2 true DE2238734C2 (de) | 1983-02-17 |
Family
ID=4378211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238734A Expired DE2238734C2 (de) | 1971-08-13 | 1972-08-05 | Bis-benzofuranyl-Verbindungen und deren Verwendung als optische Aufheller |
Country Status (18)
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2306515A1 (de) * | 1973-02-09 | 1974-08-15 | Bayer Ag | Benzo-difuran-verbindungen |
| JPS51138852U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-04-26 | 1976-11-09 | ||
| DE2724408A1 (de) | 1976-06-02 | 1977-12-15 | Ciba Geigy Ag | V-triazole |
| CH623971B5 (de) * | 1976-06-04 | 1982-01-15 | Hoechst Ag | Verfahren zur herstellung neuer benzofuranderivate und deren verwendung als optische aufheller. |
| DE2711363A1 (de) * | 1977-03-16 | 1978-09-21 | Hoechst Ag | Verfahren zur herstellung von sulfonierten benzofuran-derivaten |
| DE2843850C2 (de) * | 1978-10-07 | 1987-02-12 | Bayer Ag, 5090 Leverkusen | Farbstofflaser |
| DE2918965A1 (de) * | 1979-05-11 | 1980-11-20 | Bayer Ag | Benzofuranverbindungen sowie deren verwendung als optische aufheller |
| DE2937231A1 (de) * | 1979-09-14 | 1981-04-02 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von bis-ben-zofuranyl-verbindungen |
| FR2586717B1 (fr) * | 1985-09-04 | 1988-03-18 | Picardie Lainiere | Produit thermocollant ameliore et son procede de fabrication |
| US5230820A (en) * | 1987-11-23 | 1993-07-27 | Ciba-Geigy Corporation | Storage-stable bleaching detergents containing bis-benzofuranyl fluoescent whitening agents |
| ES2065328T3 (es) * | 1987-11-26 | 1995-02-16 | Ciba Geigy Ag | Detergentes estables que contienen blanqueantes opticos. |
| US5470990A (en) * | 1988-06-02 | 1995-11-28 | Ciba-Geigy Corporation | Sulfonation of benzofuranylbiphenyls |
| GB8824108D0 (en) * | 1988-10-14 | 1988-11-23 | Unilever Plc | Bleaching & detergent compositions |
| US5326491A (en) * | 1989-04-28 | 1994-07-05 | Ciba-Geigy Corporation | Detergents containing certain sulfonated dibenzofuranylbiphenyls |
| US5279772A (en) * | 1989-04-28 | 1994-01-18 | Ciba-Geigy Corporation | Liquid detergents containing specifically disulfonated dibenzofuranyl-biphenyls as flourescent whitening agents |
| MX9207050A (es) * | 1991-12-19 | 1993-06-01 | Ciba Geigy Ag | Dispersion de blanqueador estable durante el almacenamiento |
| US5948153A (en) * | 1998-04-24 | 1999-09-07 | Milliken & Company | Water-soluble complexes of optical brighteners and quaternary ammonium compounds which are substantially free from unwanted salts |
| US9493435B2 (en) | 2009-11-03 | 2016-11-15 | Mannking Corporation | IRE-1α inhibitors |
| WO2013102145A1 (en) | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| PL3738434T3 (pl) | 2011-12-28 | 2024-03-04 | Global Blood Therapeutics, Inc. | Związki pośrednie do otrzymywania podstawionych związków benzaldehydowych i sposoby ich zastosowania do zwiększania natlenienia tkanek |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| JP6401771B2 (ja) | 2013-03-15 | 2018-10-10 | グローバル ブラッド セラピューティクス インコーポレイテッド | ヘモグロビンの修飾のための化合物及びその使用 |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| AP2015008721A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| CN105051044A (zh) | 2013-03-15 | 2015-11-11 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| CN105431147A (zh) | 2014-02-07 | 2016-03-23 | 全球血液疗法股份有限公司 | 2-羟基-6-((2-(1-异丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)苯甲醛的游离碱的结晶多晶型物 |
| CN104119311B (zh) * | 2014-05-15 | 2016-02-03 | 杭州师范大学 | 一种2，6-二芳基萘类化合物及其制备方法 |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| EP3374354B1 (en) * | 2015-11-11 | 2022-09-28 | Ambient Photonics, Inc. | Benzofuran derivatives for the treatment of cns and other disorders |
| WO2017096230A1 (en) | 2015-12-04 | 2017-06-08 | Global Blood Therapeutics, Inc. | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| TWI663160B (zh) | 2016-05-12 | 2019-06-21 | 全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| CN107089959A (zh) * | 2017-05-25 | 2017-08-25 | 浙江明生新材料有限公司 | 一种高日晒牢度棉用增白剂及其合成方法 |
| WO2020072377A1 (en) | 2018-10-01 | 2020-04-09 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin for the treatment of sickle cell disease |
| CN112457308B (zh) * | 2019-09-09 | 2024-01-02 | 上海长森药业有限公司 | 新型三环芳香杂环化合物，及其制备方法、药物组合物和应用 |
| JP7729632B2 (ja) * | 2020-05-22 | 2025-08-26 | シャンハイ ロングウッド バイオファルマシューティカルズ カンパニー リミテッド | 新規三環芳香族複素環化合物、ならびにその調製方法、医薬組成物および適用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540247A (de) * | 1967-04-21 | 1973-09-28 | Ciba Geigy Ag | Verfahren zur Herstellung von heterocyclischen, Asthylendoppelbindungen enthaltenden Verbindungen |
| CH523909A (de) * | 1969-01-09 | 1972-06-15 | Ciba Geigy Ag | Verfahren zur Herstellung heterocyclischer, Aethylendoppelbindungen enthaltender Verbindungen und deren Verwendung als optische Aufhellmittel ausserhalb der Textilindustrie |
-
0
- BE BE787576D patent/BE787576A/xx unknown
-
1971
- 1971-08-13 CH CH1192471D patent/CH1192471A4/xx unknown
- 1971-08-13 CH CH1192471A patent/CH568432B5/xx not_active IP Right Cessation
-
1972
- 1972-08-05 DE DE2238734A patent/DE2238734C2/de not_active Expired
- 1972-08-08 NL NL7210834A patent/NL7210834A/xx not_active Application Discontinuation
- 1972-08-08 ES ES405652A patent/ES405652A1/es not_active Expired
- 1972-08-10 AU AU45439/72A patent/AU465055B2/en not_active Expired
- 1972-08-10 US US279531A patent/US3859350A/en not_active Expired - Lifetime
- 1972-08-11 GB GB3757472A patent/GB1399509A/en not_active Expired
- 1972-08-11 CA CA149,215A patent/CA1000702A/en not_active Expired
- 1972-08-11 AT AT695572A patent/AT344660B/de not_active IP Right Cessation
- 1972-08-11 AR AR243537A patent/AR218844A1/es active
- 1972-08-11 SE SE7210443A patent/SE386446B/xx unknown
- 1972-08-11 BR BR5497/72A patent/BR7205497D0/pt unknown
- 1972-08-11 IT IT28157/72A patent/IT963966B/it active
- 1972-08-11 JP JP47080051A patent/JPS5012457B2/ja not_active Expired
- 1972-08-11 DD DD165016A patent/DD103472A5/xx unknown
- 1972-08-11 NO NO2888/72A patent/NO137898B/no unknown
- 1972-08-16 FR FR7229325A patent/FR2154435B1/fr not_active Expired
-
1973
- 1973-05-10 FR FR7316886A patent/FR2183291B1/fr not_active Expired
- 1973-10-30 ES ES420070A patent/ES420070A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |