DE2366216C2 - Verfahren zur Herstellung der wasserlöslichen Natriumsalze der Carboxymethoxy-Bernsteinsäure - Google Patents
Verfahren zur Herstellung der wasserlöslichen Natriumsalze der Carboxymethoxy-BernsteinsäureInfo
- Publication number
- DE2366216C2 DE2366216C2 DE2366216A DE2366216A DE2366216C2 DE 2366216 C2 DE2366216 C2 DE 2366216C2 DE 2366216 A DE2366216 A DE 2366216A DE 2366216 A DE2366216 A DE 2366216A DE 2366216 C2 DE2366216 C2 DE 2366216C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- salt
- sodium
- methanol
- succinic acid
- 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
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- CIOXZGOUEYHNBF-UHFFFAOYSA-N (carboxymethoxy)succinic acid Chemical class OC(=O)COC(C(O)=O)CC(O)=O CIOXZGOUEYHNBF-UHFFFAOYSA-N 0.000 title claims description 8
- 159000000000 sodium salts Chemical class 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
- 239000011734 sodium Substances 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- -1 sodium carboxymethoxy succinic acid tetrahydrate Chemical compound 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 239000003599 detergent Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 150000004686 pentahydrates Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004685 tetrahydrates Chemical class 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- MPSJHIAGGNGGEZ-UHFFFAOYSA-L trisodium;2-(carboxymethoxy)butanedioate Chemical compound [Na+].[Na+].[Na+].OC(=O)COC(C([O-])=O)CC([O-])=O MPSJHIAGGNGGEZ-UHFFFAOYSA-L 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- CFPOJWPDQWJEMO-UHFFFAOYSA-N 2-(1,2-dicarboxyethoxy)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)OC(C(O)=O)CC(O)=O CFPOJWPDQWJEMO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FAAQYZLKKYNOKF-UHFFFAOYSA-K C(=O)([O-])COC(C(=O)[O-])CC(=O)[O-].[K+].[K+].[K+] Chemical compound C(=O)([O-])COC(C(=O)[O-])CC(=O)[O-].[K+].[K+].[K+] FAAQYZLKKYNOKF-UHFFFAOYSA-K 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000001744 Sodium fumarate Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- MPSJHIAGGNGGEZ-UHFFFAOYSA-K trisodium;2-(carboxylatomethoxy)butanedioate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)COC(C([O-])=O)CC([O-])=O MPSJHIAGGNGGEZ-UHFFFAOYSA-K 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2089—Ether acids-salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/248,053 US4100188A (en) | 1972-04-27 | 1972-04-27 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2366216C2 true DE2366216C2 (de) | 1982-01-28 |
Family
ID=22937464
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2366216A Expired DE2366216C2 (de) | 1972-04-27 | 1973-04-17 | Verfahren zur Herstellung der wasserlöslichen Natriumsalze der Carboxymethoxy-Bernsteinsäure |
| DE2319429A Expired DE2319429C3 (de) | 1972-04-27 | 1973-04-17 | Verfahren zur Herstellung von wasserlöslichen Natrium-, Kalium- oder Ammoniumsalzen der Carboxymethoxy-Brnsteinsäure |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2319429A Expired DE2319429C3 (de) | 1972-04-27 | 1973-04-17 | Verfahren zur Herstellung von wasserlöslichen Natrium-, Kalium- oder Ammoniumsalzen der Carboxymethoxy-Brnsteinsäure |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4100188A (en:Method) |
| JP (1) | JPS546531B2 (en:Method) |
| BE (1) | BE798773A (en:Method) |
| CA (1) | CA1000733A (en:Method) |
| DE (2) | DE2366216C2 (en:Method) |
| FR (1) | FR2182130B1 (en:Method) |
| GB (1) | GB1419991A (en:Method) |
| NL (1) | NL7305798A (en:Method) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60249828A (ja) * | 1984-05-23 | 1985-12-10 | ニユ−ト−キヨ−株式会社 | 自動車のバツテリ−充電方法及び装置 |
| JPS61295835A (ja) * | 1985-06-25 | 1986-12-26 | 松下電器産業株式会社 | 充電式掃除機の充電制御装置 |
| JPS6253134A (ja) * | 1985-08-29 | 1987-03-07 | 東光株式会社 | 充電器 |
| JPS62118719A (ja) * | 1985-11-14 | 1987-05-30 | 松下電器産業株式会社 | 車専用充電式掃除機の充電制御装置 |
| US4663071A (en) * | 1986-01-30 | 1987-05-05 | The Procter & Gamble Company | Ether carboxylate detergent builders and process for their preparation |
| US4798907A (en) * | 1988-02-26 | 1989-01-17 | The Procter & Gamble Company | Controlled temperature process for making 2,2'-oxodisuccinates useful as laundry detergent builders |
| JPH01134944U (en:Method) * | 1988-03-03 | 1989-09-14 | ||
| US5034105A (en) * | 1989-07-27 | 1991-07-23 | Michigan Biotechnology Institute | Carboxylic acid purification and crystallization process |
| US5958744A (en) * | 1997-08-18 | 1999-09-28 | Applied Carbochemicals | Succinic acid production and purification |
| DE102012016463A1 (de) | 2012-08-18 | 2014-02-20 | Clariant International Ltd. | Verfahren zur Herstellung von Carboxymethyloxy-bernsteinsäure und deren Salzen ausgehend von Glyoxal |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2057258A1 (de) * | 1968-05-24 | 1971-06-24 | Unilever Nv | Wasch- und Reinigungsmittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635830A (en) * | 1968-05-24 | 1972-01-18 | Lever Brothers Ltd | Detergent compositions containing oxydisuccing acid salts as builders |
-
1972
- 1972-04-27 US US05/248,053 patent/US4100188A/en not_active Expired - Lifetime
-
1973
- 1973-03-22 CA CA166,767A patent/CA1000733A/en not_active Expired
- 1973-04-17 DE DE2366216A patent/DE2366216C2/de not_active Expired
- 1973-04-17 DE DE2319429A patent/DE2319429C3/de not_active Expired
- 1973-04-25 NL NL7305798A patent/NL7305798A/xx not_active Application Discontinuation
- 1973-04-26 JP JP4829773A patent/JPS546531B2/ja not_active Expired
- 1973-04-26 FR FR7315129A patent/FR2182130B1/fr not_active Expired
- 1973-04-26 BE BE130463A patent/BE798773A/xx not_active IP Right Cessation
- 1973-04-27 GB GB2018773A patent/GB1419991A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2057258A1 (de) * | 1968-05-24 | 1971-06-24 | Unilever Nv | Wasch- und Reinigungsmittel |
| US3692685A (en) * | 1968-05-24 | 1972-09-19 | Lever Brothers Ltd | Detergent compositions |
Non-Patent Citations (4)
| Title |
|---|
| Fieser, L.F.: Experiments in Organic Chemistry, 3. Aufl., 1957, S. 32, 33 * |
| Lehrbuch von Perrin, 1966, S. 15, 357 * |
| Römpp: Chemie-Lexikon, 5. Aufl., 1962, Sp. 398 * |
| Vogel: Practical Organic Chemistry, 1956, S. 122-125 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2319429B2 (de) | 1974-04-18 |
| JPS546531B2 (en:Method) | 1979-03-29 |
| NL7305798A (en:Method) | 1973-10-30 |
| FR2182130A1 (en:Method) | 1973-12-07 |
| FR2182130B1 (en:Method) | 1977-04-29 |
| DE2319429A1 (de) | 1973-12-13 |
| DE2319429C3 (de) | 1982-03-25 |
| BE798773A (fr) | 1973-10-26 |
| CA1000733A (en) | 1976-11-30 |
| US4100188A (en) | 1978-07-11 |
| GB1419991A (en) | 1976-01-07 |
| JPS4947315A (en:Method) | 1974-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
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