CH495425A - Verfahren zur Herstellung eines Isohumulone enthaltenden Hopfenextraktes - Google Patents
Verfahren zur Herstellung eines Isohumulone enthaltenden HopfenextraktesInfo
- Publication number
- CH495425A CH495425A CH1654266A CH1654266A CH495425A CH 495425 A CH495425 A CH 495425A CH 1654266 A CH1654266 A CH 1654266A CH 1654266 A CH1654266 A CH 1654266A CH 495425 A CH495425 A CH 495425A
- Authority
- CH
- Switzerland
- Prior art keywords
- aqueous
- solution
- water
- humulones
- liters
- Prior art date
Links
- 239000000284 extract Substances 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 35
- 229930193815 Isohumulone Natural products 0.000 title claims description 33
- 238000002360 preparation method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 239000000243 solution Substances 0.000 claims description 76
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- 239000003513 alkali Substances 0.000 claims description 44
- 239000008346 aqueous phase Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 30
- OLHLJBVALXTBSQ-UHFFFAOYSA-N Lupulone Natural products CC(C)CC(=O)C1C(=O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O OLHLJBVALXTBSQ-UHFFFAOYSA-N 0.000 claims description 28
- LSDULPZJLTZEFD-UHFFFAOYSA-N lupulone Chemical class CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O LSDULPZJLTZEFD-UHFFFAOYSA-N 0.000 claims description 28
- 239000003208 petroleum Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- 235000008694 Humulus lupulus Nutrition 0.000 claims description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 21
- 230000000996 additive effect Effects 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 239000012071 phase Substances 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 18
- 239000000341 volatile oil Substances 0.000 claims description 17
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 235000013405 beer Nutrition 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 238000006317 isomerization reaction Methods 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 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 claims description 7
- 239000011575 calcium Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 235000019198 oils Nutrition 0.000 claims description 7
- 159000000007 calcium salts Chemical class 0.000 claims description 6
- 239000000346 nonvolatile oil Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000012153 distilled water Substances 0.000 claims description 4
- 229940106579 hops extract Drugs 0.000 claims description 4
- 239000001906 humulus lupulus l. absolute Substances 0.000 claims description 4
- QARXXMMQVDCYGZ-UHFFFAOYSA-N isohumulone Chemical compound CC(C)CC(=O)C1=C(O)C(O)(C(=O)CC=C(C)C)C(CC=C(C)C)C1=O QARXXMMQVDCYGZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkali metal cation Chemical class 0.000 claims description 3
- 239000001099 ammonium carbonate Substances 0.000 claims description 3
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 3
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000012467 final product Substances 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
- 238000011084 recovery Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- WPVSVIXDXMNGGN-UHFFFAOYSA-N beta-bitter acid Natural products CC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)=C1O WPVSVIXDXMNGGN-UHFFFAOYSA-N 0.000 description 3
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000013124 brewing process Methods 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- YDAFVJGIRJZGKB-UHFFFAOYSA-N hulupone Chemical compound CC(C)CC(=O)C1=C(O)C(=O)C(CC=C(C)C)(CC=C(C)C)C1=O YDAFVJGIRJZGKB-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/12—Isomerised products from hops
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/11—Post fermentation treatments, e.g. carbonation, or concentration
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/04—Conserving; Storing; Packing
- C12C3/08—Solvent extracts from hops
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C7/00—Preparation of wort
- C12C7/20—Boiling the beerwort
- C12C7/205—Boiling with hops
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Gas Separation By Absorption (AREA)
- Respiratory Apparatuses And Protective Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4886665A GB1161787A (en) | 1965-11-17 | 1965-11-17 | Manufacture of Hop Extracts. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495425A true CH495425A (de) | 1970-08-31 |
Family
ID=10450220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1654266A CH495425A (de) | 1965-11-17 | 1966-11-17 | Verfahren zur Herstellung eines Isohumulone enthaltenden Hopfenextraktes |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5037760B1 (is") |
| AT (2) | AT271355B (is") |
| BE (1) | BE689841A (is") |
| CH (1) | CH495425A (is") |
| DE (3) | DE1792737A1 (is") |
| ES (2) | ES333438A1 (is") |
| FR (1) | FR1502208A (is") |
| GB (1) | GB1161787A (is") |
| IT (1) | IT954011B (is") |
| MY (1) | MY7300184A (is") |
| NL (1) | NL6616150A (is") |
| SE (2) | SE388207B (is") |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1362695A (en) * | 1970-09-17 | 1974-08-07 | Carlton & United Breweries | Isomerised hop extract |
| DE2350633C3 (de) * | 1973-10-09 | 1982-06-03 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verfahren zur Extraktion von Hopfen |
| CA1132068A (en) * | 1978-05-26 | 1982-09-21 | Charles D. Baker | Production of iso-alpha acids |
| US4778691A (en) * | 1987-04-03 | 1988-10-18 | Kalamazoo Holdings, Inc. | Removal of deleterious odor-forming impurities from hop flavors |
| US6583322B1 (en) | 2000-02-25 | 2003-06-24 | Kalamazoo Holdings, Inc. | Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same |
-
1965
- 1965-11-17 GB GB4886665A patent/GB1161787A/en not_active Expired
-
1966
- 1966-11-15 DE DE19661792737 patent/DE1792737A1/de not_active Withdrawn
- 1966-11-15 DE DE19661792738 patent/DE1792738A1/de active Pending
- 1966-11-15 DE DE19661517741 patent/DE1517741A1/de not_active Ceased
- 1966-11-16 AT AT1060566A patent/AT271355B/de active
- 1966-11-16 AT AT795368A patent/AT281731B/de not_active IP Right Cessation
- 1966-11-16 NL NL6616150A patent/NL6616150A/xx unknown
- 1966-11-16 SE SE237172A patent/SE388207B/xx unknown
- 1966-11-16 IT IT5610366A patent/IT954011B/it active
- 1966-11-16 ES ES0333438A patent/ES333438A1/es not_active Expired
- 1966-11-16 SE SE1568966A patent/SE345140B/xx unknown
- 1966-11-17 FR FR84062A patent/FR1502208A/fr not_active Expired
- 1966-11-17 BE BE689841D patent/BE689841A/xx unknown
- 1966-11-17 CH CH1654266A patent/CH495425A/de not_active IP Right Cessation
-
1967
- 1967-08-01 ES ES343705A patent/ES343705A1/es not_active Expired
-
1971
- 1971-11-19 JP JP46092483A patent/JPS5037760B1/ja active Pending
-
1973
- 1973-12-31 MY MY7300184A patent/MY7300184A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE388207B (sv) | 1976-09-27 |
| ES343705A1 (es) | 1968-09-16 |
| BE689841A (is") | 1967-05-02 |
| DE1517741A1 (de) | 1970-04-02 |
| MY7300184A (en) | 1973-12-31 |
| DE1792738A1 (de) | 1973-05-24 |
| JPS5037760B1 (is") | 1975-12-04 |
| DE1792737A1 (de) | 1973-05-24 |
| SE345140B (is") | 1972-05-15 |
| AT271355B (de) | 1969-05-27 |
| IT954011B (it) | 1973-08-30 |
| AT281731B (de) | 1970-05-25 |
| NL6616150A (is") | 1967-05-18 |
| ES333438A1 (es) | 1967-12-01 |
| FR1502208A (fr) | 1967-11-18 |
| GB1161787A (en) | 1969-08-20 |
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