DE2353918C2 - Verfahren zur Herstellung von aromatischen Sulfonsäuren - Google Patents
Verfahren zur Herstellung von aromatischen SulfonsäurenInfo
- Publication number
- DE2353918C2 DE2353918C2 DE2353918A DE2353918A DE2353918C2 DE 2353918 C2 DE2353918 C2 DE 2353918C2 DE 2353918 A DE2353918 A DE 2353918A DE 2353918 A DE2353918 A DE 2353918A DE 2353918 C2 DE2353918 C2 DE 2353918C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- sulfur trioxide
- aromatic
- sulfonation
- hydrocarbon
- 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
- 238000000034 method Methods 0.000 title claims description 30
- -1 aromatic sulfonic acids Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 150000003457 sulfones Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000011086 high cleaning Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/02—Formation or introduction of functional groups containing sulfur of sulfo or sulfonyldioxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4992872A GB1434019A (en) | 1972-10-30 | 1972-10-30 | Sulphonation of aromatic compounds |
| GB4950973A GB1434020A (en) | 1972-10-30 | 1972-10-30 | Sulphonation of aromatic compounds in the presence of solvents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2353918A1 DE2353918A1 (de) | 1974-05-02 |
| DE2353918C2 true DE2353918C2 (de) | 1983-06-23 |
Family
ID=26266499
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2353918A Expired DE2353918C2 (de) | 1972-10-30 | 1973-10-27 | Verfahren zur Herstellung von aromatischen Sulfonsäuren |
| DE19732354097 Withdrawn DE2354097A1 (de) | 1972-10-30 | 1973-10-29 | Verfahren zur sulfonierung aromatischer kohlenwasserstoffe mit hilfe von gasfoermigem schwefeltrioxid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732354097 Withdrawn DE2354097A1 (de) | 1972-10-30 | 1973-10-29 | Verfahren zur sulfonierung aromatischer kohlenwasserstoffe mit hilfe von gasfoermigem schwefeltrioxid |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723858B (zh) * | 2008-10-17 | 2012-07-18 | 南化集团研究院 | 一种制备苯磺酸的方法 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357281A (en) * | 1978-05-30 | 1982-11-02 | The Dow Chemical Company | Alkylated biphenylyl phenyl ether sulfonates |
| DE2853337A1 (de) * | 1978-12-09 | 1980-06-26 | Bayer Ag | Neue sulfierungsprodukte des naphthalins, verfahren zu ihrer herstellung und verwendung |
| DE2901178A1 (de) * | 1979-01-13 | 1980-07-24 | Bayer Ag | Verfahren zur herstellung von naphthalin-1,3,5-trisulfonsaeure |
| US4322367A (en) * | 1979-11-26 | 1982-03-30 | Colgate-Palmolive Company | Deoiling of aqueous solutions of sodium lauryl sulfate |
| DE3330334A1 (de) * | 1983-08-23 | 1985-03-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur sulfonierung von aromatischen verbindungen mit schwefeltrioxid |
| DE3463264D1 (en) * | 1983-11-28 | 1987-05-27 | Ciba Geigy Ag | Process for the preparation of 4-nitrotoluene-2-sulfonic acid |
| US4937387A (en) * | 1986-09-05 | 1990-06-26 | Amoco Corporation | Processes for preparing diaryl sulfones |
| WO1988001617A1 (en) * | 1986-09-05 | 1988-03-10 | Amoco Corporation | Improvement for processes for preparing diaryl sulfones |
| US5164465A (en) * | 1988-05-13 | 1992-11-17 | Ohio State University Research Foundation | Sulfonated polyaniline salt compositions, processes for their preparation and uses thereof |
| US5208301A (en) * | 1988-05-13 | 1993-05-04 | Ohio State University Research Foundation | Sulfonated polyaniline compositions, ammonium salts thereof, process for their preparation and uses thereof |
| US5159031A (en) * | 1988-05-13 | 1992-10-27 | Ohio State University Research Foundation | Sulfonated polyaniline salt compositions and uses thereof |
| US5137991A (en) * | 1988-05-13 | 1992-08-11 | The Ohio State University Research Foundation | Polyaniline compositions, processes for their preparation and uses thereof |
| US5109070A (en) * | 1989-10-19 | 1992-04-28 | Ohio State University Research Foundation | Compositions of insulating polymers and sulfonated polyaniline compositions and uses thereof |
| US5135696A (en) * | 1989-10-19 | 1992-08-04 | Ohio State University Research Foundation | Process for forming fibers of sulfonated polyaniline compositions and uses thereof |
| US5093439A (en) * | 1989-10-19 | 1992-03-03 | Ohio State University Research Foundation | Processes for preparation of sulfonated polyaniline compositions and uses thereof |
| DE4007603A1 (de) * | 1990-03-09 | 1991-09-12 | Henkel Kgaa | Verfahren zur herstellung von naphthalinsulfonsaeuren |
| KR0185224B1 (ko) * | 1990-10-12 | 1999-05-15 | 고니시 기히꼬 | 술폰화제 및 술폰화법 |
| CN102180815B (zh) * | 2011-03-23 | 2013-02-27 | 江苏中丹集团股份有限公司 | 一种气相磺化法生产间苯二磺酸的生产工艺 |
| US9388128B2 (en) | 2011-04-18 | 2016-07-12 | Solvay Speciality Polymers Usa, Llc | Process for the manufacture of dihalodiphenylsulfones starting from organic acids |
| EP2699542B1 (en) | 2011-04-18 | 2016-10-12 | Solvay Specialty Polymers USA, LLC. | Process for the manufacture of dihalodiphenylsulfones |
| CN102746195A (zh) * | 2011-04-27 | 2012-10-24 | 江苏尼高科技有限公司 | 一种改进萘系减水剂磺化工艺的方法 |
| CN105237442A (zh) * | 2015-10-20 | 2016-01-13 | 江苏瑞燕橡塑助剂有限公司 | 一种磺化过程中芳烃的回收方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2616936A (en) * | 1949-04-12 | 1952-11-04 | Universal Oil Prod Co | Method of sulfonation with sulfur trioxide |
| US2704295A (en) * | 1952-07-11 | 1955-03-15 | Allied Chem & Dye Corp | Aromatic hydrocarbon sulfonation |
| US2832801A (en) * | 1954-07-19 | 1958-04-29 | Emulsol Chemical Corp | Sulfonation of alkyl benzenes with sulfur trioxide |
| US2798089A (en) * | 1954-11-29 | 1957-07-02 | Tennessee Corp | Sulfonation of benzene |
| NL278901A (US20100154141A1-20100624-C00001.png) * | 1961-05-26 | |||
| BE634264A (US20100154141A1-20100624-C00001.png) * | 1962-06-28 | |||
| NL129849C (US20100154141A1-20100624-C00001.png) * | 1964-06-04 | |||
| CH439265A (de) * | 1964-07-16 | 1967-07-15 | Sandoz Ag | Verfahren zur Herstellung von a-Naphthalinsulfonsäure |
| DE1813646C3 (de) * | 1968-12-10 | 1978-08-10 | Chemische Werke Lowi Gmbh, 8264 Waldkraiburg | Verfahren zur Herstellung von Arylsulfonsäuren |
| NL7005559A (US20100154141A1-20100624-C00001.png) * | 1969-04-25 | 1970-10-27 | ||
| GB1306226A (US20100154141A1-20100624-C00001.png) * | 1969-04-30 | 1973-02-07 |
-
1972
- 1972-10-30 GB GB4992872A patent/GB1434019A/en not_active Expired
- 1972-10-30 GB GB4950973A patent/GB1434020A/en not_active Expired
-
1973
- 1973-10-27 DE DE2353918A patent/DE2353918C2/de not_active Expired
- 1973-10-29 SE SE7314690A patent/SE421416B/xx unknown
- 1973-10-29 SE SE7314689A patent/SE421415B/xx unknown
- 1973-10-29 DE DE19732354097 patent/DE2354097A1/de not_active Withdrawn
- 1973-10-30 US US05/411,053 patent/US3941810A/en not_active Expired - Lifetime
- 1973-10-30 JP JP12214873A patent/JPS566989B2/ja not_active Expired
- 1973-10-30 FR FR7338635A patent/FR2204596B2/fr not_active Expired
- 1973-10-30 US US05/411,054 patent/US3946037A/en not_active Expired - Lifetime
- 1973-10-30 JP JP12214773A patent/JPS546540B2/ja not_active Expired
- 1973-10-30 FR FR7338575A patent/FR2204595B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723858B (zh) * | 2008-10-17 | 2012-07-18 | 南化集团研究院 | 一种制备苯磺酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49132032A (US20100154141A1-20100624-C00001.png) | 1974-12-18 |
| FR2204596A2 (US20100154141A1-20100624-C00001.png) | 1974-05-24 |
| JPS49132033A (US20100154141A1-20100624-C00001.png) | 1974-12-18 |
| US3941810A (en) | 1976-03-02 |
| US3946037A (en) | 1976-03-23 |
| DE2354097A1 (de) | 1974-05-22 |
| JPS566989B2 (US20100154141A1-20100624-C00001.png) | 1981-02-14 |
| JPS546540B2 (US20100154141A1-20100624-C00001.png) | 1979-03-29 |
| FR2204596B2 (US20100154141A1-20100624-C00001.png) | 1976-05-07 |
| FR2204595A1 (US20100154141A1-20100624-C00001.png) | 1974-05-24 |
| GB1434020A (en) | 1976-04-28 |
| GB1434019A (en) | 1976-04-28 |
| SE421416B (sv) | 1981-12-21 |
| SE421415B (sv) | 1981-12-21 |
| FR2204595B1 (US20100154141A1-20100624-C00001.png) | 1976-05-07 |
| DE2353918A1 (de) | 1974-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: REWO CHEMISCHE WERKE GMBH, 6497 STEINAU, DE |
|
| 8181 | Inventor (new situation) |
Free format text: KOEBNER, ADOLF, DR.PHIL., ST. BEES, CUMBERLAND, GB |
|
| AG | Has addition no. |
Ref country code: DE Ref document number: 2354097 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8365 | Fully valid after opposition proceedings | ||
| 8339 | Ceased/non-payment of the annual fee |