NO129337B - - Google Patents
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- Publication number
- NO129337B NO129337B NO04963/68A NO496368A NO129337B NO 129337 B NO129337 B NO 129337B NO 04963/68 A NO04963/68 A NO 04963/68A NO 496368 A NO496368 A NO 496368A NO 129337 B NO129337 B NO 129337B
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- keto
- alkylprogesterone
- methyl
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 alkyl oxalate Chemical compound 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 241000122824 Aspergillus ochraceus Species 0.000 claims description 3
- 241000223211 Curvularia lunata Species 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 241000235546 Rhizopus stolonifer Species 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000033444 hydroxylation Effects 0.000 claims 3
- 238000005805 hydroxylation reaction Methods 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 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 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 3
- 230000001706 oxygenating effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
- JYYRDDFNMDZIIP-IDDWWOGSSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13,16-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(C)[C@H](C(C)=O)[C@@]1(C)CC2 JYYRDDFNMDZIIP-IDDWWOGSSA-N 0.000 description 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WFEIIAIREWCXNS-FAPAVZISSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13,16-trimethyl-2,6,7,8,9,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound CC1[C@@H]([C@]2(CC([C@@H]3[C@]4(CCC(C=C4CC[C@H]3[C@@H]2C1)=O)C)=O)C)C(C)=O WFEIIAIREWCXNS-FAPAVZISSA-N 0.000 description 1
- XXSFRYVGIQYVIQ-UHFFFAOYSA-N 1-(3-hydroxy-10,13,16-trimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethanone Chemical compound C1C=C2CC(O)CCC2(C)C2C1C1CC(C)C(C(C)=O)C1(C)CC2 XXSFRYVGIQYVIQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CRRKVZVYZQXICQ-RJJCNJEVSA-N Pregnenolone acetate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H](C(C)=O)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 CRRKVZVYZQXICQ-RJJCNJEVSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000001780 adrenocortical effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D71/00—Bundles of articles held together by packaging elements for convenience of storage or transport, e.g. portable segregating carrier for plural receptacles such as beer cans or pop bottles; Bales of material
- B65D71/06—Packaging elements holding or encircling completely or almost completely the bundle of articles, e.g. wrappers
- B65D71/08—Wrappers shrunk by heat or under tension, e.g. stretch films or films tensioned by compressed articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D73/00—Packages comprising articles attached to cards, sheets or webs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D75/00—Packages comprising articles or materials partially or wholly enclosed in strips, sheets, blanks, tubes, or webs of flexible sheet material, e.g. in folded wrappers
- B65D75/52—Details
- B65D75/54—Cards, coupons, or other inserts or accessories
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D2571/00—Bundles of articles held together by packaging elements for convenience of storage or transport, e.g. portable segregating carrier for plural receptacles such as beer cans, pop bottles; Bales of material
- B65D2571/00006—Palletisable loads, i.e. loads intended to be transported by means of a fork-lift truck
- B65D2571/00012—Bundles surrounded by a film
- B65D2571/00018—Bundles surrounded by a film under tension
- B65D2571/00024—Mechanical characteristics of the shrink film
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Packages (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69795768A | 1968-01-15 | 1968-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129337B true NO129337B (pl) | 1974-04-01 |
Family
ID=24803296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04963/68A NO129337B (pl) | 1968-01-15 | 1968-12-11 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3424306A (pl) |
| AT (1) | AT294691B (pl) |
| BE (1) | BE725224A (pl) |
| BR (1) | BR6804745D0 (pl) |
| CH (1) | CH489403A (pl) |
| FR (1) | FR1595053A (pl) |
| GB (1) | GB1239998A (pl) |
| NL (1) | NL152214B (pl) |
| NO (1) | NO129337B (pl) |
| OA (1) | OA02952A (pl) |
| SE (1) | SE360328B (pl) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3734279A (en) * | 1971-06-30 | 1973-05-22 | Union Carbide Corp | Display tray |
| US3863837A (en) * | 1972-08-17 | 1975-02-04 | Gilbreth Co | Cardless head board merchandising package |
| FR2223983A5 (pl) * | 1973-03-28 | 1974-10-25 | Solvay | |
| US3881601A (en) * | 1973-09-21 | 1975-05-06 | Possis Corp | Rack display package for dry cells and the like |
| US3990578A (en) * | 1974-10-25 | 1976-11-09 | Packaging Corporation Of America | Foldable display package |
| EP0018705B1 (en) * | 1979-03-09 | 1983-12-07 | The Mead Corporation | Composite material packages and method of producing such packages |
| US4696402A (en) * | 1985-03-19 | 1987-09-29 | Rayovac Corporation | Easy-open, individual unit dispensing package |
| US4940141A (en) * | 1989-01-17 | 1990-07-10 | Terry Philpot | Shrinkwrap beverage pack |
| US4971197A (en) * | 1989-12-06 | 1990-11-20 | Eveready Battery Company, Inc. | Battery package |
| US5143215A (en) * | 1990-06-27 | 1992-09-01 | P.T.P. Industries | Battery display package |
| US5018622A (en) * | 1990-06-27 | 1991-05-28 | P.T.P. Industries | Battery display package |
| US5323896A (en) * | 1993-06-24 | 1994-06-28 | Jones W Charles | Article packaging kit, system and method |
| US5678695A (en) * | 1995-10-11 | 1997-10-21 | Sealed Air Corporation | Packaging structure |
| US6148590A (en) * | 1995-10-11 | 2000-11-21 | Sealed Air Corporation | Packaging structure |
| US5694744A (en) * | 1996-02-29 | 1997-12-09 | Jones; William Charles | Article packaging kit, and method |
| US6050416A (en) * | 1996-04-01 | 2000-04-18 | The Mead Corporation | Display package |
| US5676245A (en) * | 1996-04-02 | 1997-10-14 | Jones; William Charles | Article packaging kit, system and method |
| EP1089922B1 (de) | 1998-06-22 | 2002-11-06 | Hawera Probst GmbH | Verkaufsverpackung |
| DE19827747B4 (de) * | 1998-06-22 | 2007-03-22 | Robert Bosch Gmbh | Verkaufspackung für Bohrer |
| US5893462A (en) * | 1998-07-01 | 1999-04-13 | Sealed Air Corporation | Retention package |
| US6302274B1 (en) | 1999-12-01 | 2001-10-16 | Sealed Air Corporation (Us) | Suspension and retention packaging structures and methods for forming same |
| GB2366276A (en) * | 2000-08-31 | 2002-03-06 | Gen Electric | Packaging for light bulbs |
| US6490844B1 (en) | 2001-06-21 | 2002-12-10 | Emerging Technologies Trust | Film wrap packaging apparatus and method |
| FR2841223B1 (fr) * | 2002-06-19 | 2004-10-15 | Sleever Int | Enveloppe d'emballage d'objets(s) en materiau thermoretractable a face interne ou externe essentiellement lisse |
| US7448497B2 (en) * | 2002-12-30 | 2008-11-11 | Fck, Llc. | Batteries, accessories, marketing bundles and marketing methods |
| US6920981B2 (en) * | 2003-01-03 | 2005-07-26 | Ade, Inc. | Suspension packages and systems, cushioning panels, and methods of using same |
| US7780009B2 (en) * | 2004-02-27 | 2010-08-24 | Eveready Battery Company, Inc. | Modular battery package |
| DE102006005453B4 (de) * | 2006-02-03 | 2008-03-13 | Beiersdorf Ag | Schrumpfbare Folienverpackung |
| US9493681B2 (en) | 2012-12-27 | 2016-11-15 | Michael James Osella | Attachment device for securing items |
| US10787286B2 (en) * | 2017-03-16 | 2020-09-29 | Sealed Air Corporation (Us) | Identification of shrink-wrapped objects |
| US11697538B2 (en) * | 2018-06-21 | 2023-07-11 | First Quality Tissue, Llc | Bundled product and system and method for forming the same |
| US11738927B2 (en) * | 2018-06-21 | 2023-08-29 | First Quality Tissue, Llc | Bundled product and system and method for forming the same |
| AU2019391712A1 (en) | 2018-12-07 | 2021-06-17 | Bedford Industries, Inc. | Tag attachment by shrink film |
| USD1000291S1 (en) * | 2020-09-04 | 2023-10-03 | Stora Enso Oyj | Take away cup carrier |
| USD1005131S1 (en) * | 2020-09-04 | 2023-11-21 | Stora Enso Oyj | Take away cup carrier |
| USD986748S1 (en) * | 2020-09-04 | 2023-05-23 | Stora Enso Oyj | Take away cup carrier |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087610A (en) * | 1960-12-27 | 1963-04-30 | Grace W R & Co | Plastic multiple pack carrier |
| US3260358A (en) * | 1964-01-27 | 1966-07-12 | Monsanto Co | Shrink wrapped textile shipping package |
-
1968
- 1968-01-15 US US697957A patent/US3424306A/en not_active Expired - Lifetime
- 1968-12-10 BE BE725224D patent/BE725224A/xx not_active IP Right Cessation
- 1968-12-11 GB GB58859/68A patent/GB1239998A/en not_active Expired
- 1968-12-11 CH CH1847068A patent/CH489403A/fr not_active IP Right Cessation
- 1968-12-11 BR BR204745/68A patent/BR6804745D0/pt unknown
- 1968-12-11 NO NO04963/68A patent/NO129337B/no unknown
- 1968-12-11 AT AT1206968A patent/AT294691B/de not_active IP Right Cessation
- 1968-12-11 OA OA53447A patent/OA02952A/xx unknown
- 1968-12-11 SE SE16961/68A patent/SE360328B/xx unknown
- 1968-12-12 NL NL686817853A patent/NL152214B/xx not_active IP Right Cessation
- 1968-12-12 FR FR1595053D patent/FR1595053A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1901104B2 (de) | 1975-09-04 |
| FR1595053A (pl) | 1970-06-08 |
| BE725224A (fr) | 1969-06-10 |
| DE1901104A1 (de) | 1969-11-20 |
| BR6804745D0 (pt) | 1973-02-01 |
| GB1239998A (en) | 1971-07-21 |
| NL6817853A (pl) | 1969-07-17 |
| NL152214B (nl) | 1977-02-15 |
| AT294691B (de) | 1971-11-25 |
| OA02952A (fr) | 1970-12-15 |
| US3424306A (en) | 1969-01-28 |
| SE360328B (pl) | 1973-09-24 |
| CH489403A (fr) | 1970-04-30 |
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