DE2229064A1 - Verfahren zur herstellung von fruktose - Google Patents
Verfahren zur herstellung von fruktoseInfo
- Publication number
- DE2229064A1 DE2229064A1 DE2229064A DE2229064A DE2229064A1 DE 2229064 A1 DE2229064 A1 DE 2229064A1 DE 2229064 A DE2229064 A DE 2229064A DE 2229064 A DE2229064 A DE 2229064A DE 2229064 A1 DE2229064 A1 DE 2229064A1
- Authority
- DE
- Germany
- Prior art keywords
- fructose
- solution
- glucose
- acid
- isomerization
- 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.)
- Pending
Links
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 title claims description 39
- 229930091371 Fructose Natural products 0.000 title claims description 35
- 239000005715 Fructose Substances 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims description 35
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 21
- 239000008103 glucose Substances 0.000 claims description 19
- -1 aryl boric acid Chemical compound 0.000 claims description 18
- 238000006317 isomerization reaction Methods 0.000 claims description 16
- 239000004327 boric acid Substances 0.000 claims description 11
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 9
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 229920000620 organic polymer Polymers 0.000 claims description 2
- BBJIQHIAPXAMSJ-UHFFFAOYSA-N (2-ethenylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1C=C BBJIQHIAPXAMSJ-UHFFFAOYSA-N 0.000 claims 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 235000010338 boric acid Nutrition 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 235000000346 sugar Nutrition 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XZRMXDPWEPRYMF-UHFFFAOYSA-N (4-ethenylphenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(C=C)C=C1 XZRMXDPWEPRYMF-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000010414 supernatant solution Substances 0.000 description 3
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XPYBSIWDXQFNMH-UHFFFAOYSA-N D-Fructose 1 Chemical compound OP(=O)(O)OCC(O)C(O)C(O)C(=O)COP(O)(O)=O XPYBSIWDXQFNMH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019534 high fructose corn syrup Nutrition 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QHFAXRHEKNHTDH-UHFFFAOYSA-N (2-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C=C QHFAXRHEKNHTDH-UHFFFAOYSA-N 0.000 description 1
- UHGZXUCJYHCRQS-UHFFFAOYSA-N (2-nitrophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1[N+]([O-])=O UHGZXUCJYHCRQS-UHFFFAOYSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- SXLHAMYMTUEALX-UHFFFAOYSA-N (4-methoxyphenoxy)boronic acid Chemical compound COC1=CC=C(OB(O)O)C=C1 SXLHAMYMTUEALX-UHFFFAOYSA-N 0.000 description 1
- NQMRYYAAICMHPE-UHFFFAOYSA-N (4-methoxyphenyl)boron Chemical compound [B]C1=CC=C(OC)C=C1 NQMRYYAAICMHPE-UHFFFAOYSA-N 0.000 description 1
- HEFOGCNQSDTNKM-UHFFFAOYSA-N (6-sulfonylcyclohexa-2,4-dien-1-yl)oxyboronic acid Chemical compound S(=O)(=O)=C1C(C=CC=C1)OB(O)O HEFOGCNQSDTNKM-UHFFFAOYSA-N 0.000 description 1
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 1
- QVNUKMYETJXJGT-UHFFFAOYSA-N B(O)(O)OC1=C(C(=C(C=C1)C=C)CC)CC=N Chemical compound B(O)(O)OC1=C(C(=C(C=C1)C=C)CC)CC=N QVNUKMYETJXJGT-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940063013 borate ion Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- LZTBZQSQFMLGQH-UHFFFAOYSA-N naphthalen-1-yloxyboronic acid Chemical compound C1=CC=C2C(OB(O)O)=CC=CC2=C1 LZTBZQSQFMLGQH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- GQQNLYRKZFBFEN-UHFFFAOYSA-N oxo(phenyl)borane Chemical compound O=BC1=CC=CC=C1 GQQNLYRKZFBFEN-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum 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
- 239000002952 polymeric resin Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K11/00—Fructose
-
- H—ELECTRICITY
- H02—GENERATION; CONVERSION OR DISTRIBUTION OF ELECTRIC POWER
- H02J—CIRCUIT ARRANGEMENTS OR SYSTEMS FOR SUPPLYING OR DISTRIBUTING ELECTRIC POWER; SYSTEMS FOR STORING ELECTRIC ENERGY
- H02J13/00—Circuit arrangements for providing remote indication of network conditions, e.g. an instantaneous record of the open or closed condition of each circuitbreaker in the network; Circuit arrangements for providing remote control of switching means in a power distribution network, e.g. switching in and out of current consumers by using a pulse code signal carried by the network
- H02J13/00004—Circuit arrangements for providing remote indication of network conditions, e.g. an instantaneous record of the open or closed condition of each circuitbreaker in the network; Circuit arrangements for providing remote control of switching means in a power distribution network, e.g. switching in and out of current consumers by using a pulse code signal carried by the network characterised by the power network being locally controlled
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2229064A DE2229064A1 (de) | 1972-06-15 | 1972-06-15 | Verfahren zur herstellung von fruktose |
| US365356A US3875140A (en) | 1972-06-15 | 1973-05-30 | Process for the preparation of fructose |
| GB2769473A GB1369185A (en) | 1972-06-15 | 1973-06-11 | Process for the production of fructose |
| FR7321456A FR2189512B1 (enExample) | 1972-06-15 | 1973-06-13 | |
| AT523873A AT329472B (de) | 1972-06-15 | 1973-06-14 | Verfahren zur herstellung von fruktose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2229064A DE2229064A1 (de) | 1972-06-15 | 1972-06-15 | Verfahren zur herstellung von fruktose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2229064A1 true DE2229064A1 (de) | 1973-12-20 |
Family
ID=5847774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2229064A Pending DE2229064A1 (de) | 1972-06-15 | 1972-06-15 | Verfahren zur herstellung von fruktose |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3875140A (enExample) |
| AT (1) | AT329472B (enExample) |
| DE (1) | DE2229064A1 (enExample) |
| FR (1) | FR2189512B1 (enExample) |
| GB (1) | GB1369185A (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497888A (en) * | 1975-06-17 | 1978-01-12 | Ici Ltd | Aldose to ketose conversion |
| US4096036A (en) * | 1976-06-15 | 1978-06-20 | Standard Brands Incorporated | Method for the separation of water soluble polyols |
| US4173559A (en) * | 1977-06-30 | 1979-11-06 | Am International, Inc. | Non-aqueous polymeric dispersion of alkyl methacrylate and alkyl acrylate copolymers in mixtures of cyclohexane and alcohols and matte coatings produced therefrom |
| US4173558A (en) * | 1977-06-30 | 1979-11-06 | Am International, Inc. | Non-aqueous polymeric dispersion alkyl methacrylate copolymers in mixtures of organic solvents and glossy coatings produced therefrom |
| US4199374A (en) * | 1978-12-22 | 1980-04-22 | Chimicasa Gmbh | Process of preparing crystalline fructose from high fructose corn syrup |
| US4199373A (en) * | 1979-04-13 | 1980-04-22 | Chimicasa Gmbh | Process for the manufacture of crystalline fructose |
| US4273922A (en) * | 1980-03-21 | 1981-06-16 | The United States Of America As Represented By The Secretary Of Agriculture | Ketose sugars from aldose sugars |
| DE3373659D1 (en) * | 1982-11-16 | 1987-10-22 | Ici Plc | Process for effecting aldose to ketose conversion |
| US5234503A (en) * | 1987-02-02 | 1993-08-10 | A.E. Saley Manufacturing Co. | Integrated process for producing crystalline fructose and a high-fructose, liquid-phase sweetener |
| US5230742A (en) * | 1987-02-02 | 1993-07-27 | A. E. Staley Manufacturing Co. | Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener |
| US5350456A (en) * | 1987-02-02 | 1994-09-27 | A. E. Staley Manufacturing Company | Integrated process for producing crystalline fructose and a high fructose, liquid-phase sweetener |
| US5656094A (en) * | 1987-02-02 | 1997-08-12 | A.E. Staley Manufacturing Company | Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener |
| WO2010091313A2 (en) * | 2009-02-06 | 2010-08-12 | Zevex, Inc. | Automatic safety occluder |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746889A (en) * | 1954-07-27 | 1956-05-22 | Staley Mfg Co A E | Interconversion of sugars using anion exchange resins |
| US2818851A (en) * | 1956-02-07 | 1958-01-07 | Joseph X Khym | Separation and analysis of polyhydroxy substances |
| US3432345A (en) * | 1966-04-07 | 1969-03-11 | Union Starch & Refining Co Inc | Production of fructose from dextrose |
| US3431253A (en) * | 1966-09-06 | 1969-03-04 | Us Army | Fructose formation from glucose |
| US3514327A (en) * | 1967-09-27 | 1970-05-26 | Us Army | Isomerization of glucose,maltose,and lactose with amino compounds |
| US3558355A (en) * | 1968-07-12 | 1971-01-26 | Eisai Co Ltd | Process for enhancement of sweetness of sugars |
| US3684574A (en) * | 1970-04-20 | 1972-08-15 | Anheuser Busch | Method of producing sweet syrup by resin isomerization of dextrose syrup |
-
1972
- 1972-06-15 DE DE2229064A patent/DE2229064A1/de active Pending
-
1973
- 1973-05-30 US US365356A patent/US3875140A/en not_active Expired - Lifetime
- 1973-06-11 GB GB2769473A patent/GB1369185A/en not_active Expired
- 1973-06-13 FR FR7321456A patent/FR2189512B1/fr not_active Expired
- 1973-06-14 AT AT523873A patent/AT329472B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2189512A1 (enExample) | 1974-01-25 |
| US3875140A (en) | 1975-04-01 |
| AT329472B (de) | 1976-05-10 |
| ATA523873A (de) | 1975-07-15 |
| GB1369185A (en) | 1974-10-02 |
| FR2189512B1 (enExample) | 1977-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |