CS214764B2 - Method of making the polymeres of cyclodextrine with polyvinylalcool capable of forming the inclusive complexes and prepared in the form of beads,foils,fibres or blocks - Google Patents

Method of making the polymeres of cyclodextrine with polyvinylalcool capable of forming the inclusive complexes and prepared in the form of beads,foils,fibres or blocks Download PDF

Info

Publication number: CS214764B2
Authority: CS; Czechoslovakia
Prior art keywords: cyclodextrin; polyvinyl alcohol; polymer; prepared; polymers
Prior art date: 1978-07-13

Application number

CS794890A

Other languages

Czech (cs)

English (en)

Inventor

Jozsef Szejtli

Eva Fenyvesi

Sandor Zoltan

Bela Zsadon

Ferenc Toedoes

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1978-07-13

Filing date

1979-07-12

Publication date

1982-05-28

1979-07-12 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1982-05-28 Publication of CS214764B2 publication Critical patent/CS214764B2/cs

Links

229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 83
229920000642 polymer Polymers 0.000 title claims abstract description 57
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 51
239000011324 bead Substances 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title claims description 5
239000011888 foil Substances 0.000 title 1
229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 43
239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 42
239000000203 mixture Substances 0.000 claims abstract description 28
229940097362 cyclodextrins Drugs 0.000 claims abstract description 16
229920002689 polyvinyl acetate Polymers 0.000 claims abstract description 10
239000011118 polyvinyl acetate Substances 0.000 claims abstract description 10
150000001720 carbohydrates Chemical class 0.000 claims abstract description 8
238000004132 cross linking Methods 0.000 claims abstract description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 36
238000000034 method Methods 0.000 claims description 16
239000000835 fiber Substances 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 9
239000003431 cross linking reagent Substances 0.000 claims description 7
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
239000004721 Polyphenylene oxide Substances 0.000 claims description 4
239000010408 film Substances 0.000 claims description 4
229920000570 polyether Polymers 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 7
229920002554 vinyl polymer Polymers 0.000 abstract description 2
230000008878 coupling Effects 0.000 abstract 1
238000010168 coupling process Methods 0.000 abstract 1
238000005859 coupling reaction Methods 0.000 abstract 1
239000000376 reactant Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 30
239000000047 product Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002245 particle Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 9
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 8
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235000004279 alanine Nutrition 0.000 description 3
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JJWFIVDAMOFNPS-QRPNPIFTSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JJWFIVDAMOFNPS-QRPNPIFTSA-N 0.000 description 2
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239000004593 Epoxy Substances 0.000 description 2
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235000001014 amino acid Nutrition 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
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238000004587 chromatography analysis Methods 0.000 description 2
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230000000536 complexating effect Effects 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
239000002612 dispersion medium Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 2
229940080345 gamma-cyclodextrin Drugs 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920006254 polymer film Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
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SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
125000002353 D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
241001104043 Syringa Species 0.000 description 1
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239000004473 Threonine Substances 0.000 description 1
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HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
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OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
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238000010668 complexation reaction Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
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229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229960002591 hydroxyproline Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000010842 industrial wastewater Substances 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000007431 microscopic evaluation Methods 0.000 description 1
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229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
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231100000719 pollutant Toxicity 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920005594 polymer fiber Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1
WHGYBXFWUBPSRW-FEYSZYNQSA-N β-dextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)C(O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FEYSZYNQSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Materials Engineering (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Artificial Filaments (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Medicinal Preparation (AREA)
Nonwoven Fabrics (AREA)

CS794890A 1978-07-13 1979-07-12 Method of making the polymeres of cyclodextrine with polyvinylalcool capable of forming the inclusive complexes and prepared in the form of beads,foils,fibres or blocks CS214764B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78CI1845A HU177419B (en)	1978-07-13	1978-07-13	Process for preparing threedimensional,retentive polymers consisting of cyclodextrin and polyvinylalcohol units,capable of forming inclusion complexes in the form of bead,fibre or mainly block

Publications (1)

Publication Number	Publication Date
CS214764B2 true CS214764B2 (en)	1982-05-28

Family

ID=10994703

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794890A CS214764B2 (en)	1978-07-13	1979-07-12	Method of making the polymeres of cyclodextrine with polyvinylalcool capable of forming the inclusive complexes and prepared in the form of beads,foils,fibres or blocks

Country Status (17)

Country	Link
US (1)	US4274985A (da)
JP (1)	JPS5820962B2 (da)
AT (1)	AT369402B (da)
BE (1)	BE877653A (da)
CA (1)	CA1124928A (da)
CH (1)	CH644386A5 (da)
CS (1)	CS214764B2 (da)
DD (1)	DD145108A1 (da)
DE (1)	DE2927733C2 (da)
DK (1)	DK166028C (da)
FI (1)	FI65444C (da)
FR (1)	FR2430954A1 (da)
GB (1)	GB2030574B (da)
HU (1)	HU177419B (da)
NO (1)	NO153967C (da)
SE (1)	SE446453B (da)
SU (1)	SU1227118A3 (da)

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US6527887B1 (en)	2002-01-18	2003-03-04	Mach I, Inc.	Polymeric cyclodextrin nitrate esters
RU2217521C2 (ru) *	2002-02-08	2003-11-27	Стадничук Александр Викторович	Литая износостойкая сталь для деталей горно-обогатительного производства
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1978
- 1978-07-13 HU HU78CI1845A patent/HU177419B/hu not_active IP Right Cessation
1979
- 1979-07-06 AT AT0471279A patent/AT369402B/de not_active IP Right Cessation
- 1979-07-09 US US06/055,536 patent/US4274985A/en not_active Expired - Lifetime
- 1979-07-10 GB GB7923950A patent/GB2030574B/en not_active Expired
- 1979-07-10 DE DE2927733A patent/DE2927733C2/de not_active Expired
- 1979-07-11 FI FI792180A patent/FI65444C/fi not_active IP Right Cessation
- 1979-07-11 FR FR7918012A patent/FR2430954A1/fr active Granted
- 1979-07-12 SE SE7906088A patent/SE446453B/sv not_active IP Right Cessation
- 1979-07-12 DD DD79214293A patent/DD145108A1/de not_active IP Right Cessation
- 1979-07-12 CH CH652179A patent/CH644386A5/de not_active IP Right Cessation
- 1979-07-12 BE BE0/196261A patent/BE877653A/xx not_active IP Right Cessation
- 1979-07-12 DK DK293379A patent/DK166028C/da not_active IP Right Cessation
- 1979-07-12 NO NO792322A patent/NO153967C/no unknown
- 1979-07-12 SU SU792788604A patent/SU1227118A3/ru active
- 1979-07-12 CS CS794890A patent/CS214764B2/cs unknown
- 1979-07-13 CA CA331,763A patent/CA1124928A/en not_active Expired
- 1979-07-13 JP JP54088357A patent/JPS5820962B2/ja not_active Expired

Also Published As

Publication number	Publication date
DD145108A1 (de)	1980-11-19
NO153967B (no)	1986-03-17
SE7906088L (sv)	1980-01-14
FI792180A7 (fi)	1980-01-14
NO792322L (no)	1980-01-15
SE446453B (sv)	1986-09-15
CH644386A5 (de)	1984-07-31
FI65444C (fi)	1984-05-10
NO153967C (no)	1986-06-25
SU1227118A3 (ru)	1986-04-23
GB2030574A (en)	1980-04-10
JPS5513796A (en)	1980-01-30
JPS5820962B2 (ja)	1983-04-26
DK166028C (da)	1993-07-12
DK166028B (da)	1993-03-01
ATA471279A (de)	1982-05-15
HU177419B (en)	1981-10-28
FR2430954A1 (fr)	1980-02-08
US4274985A (en)	1981-06-23
GB2030574B (en)	1983-03-23
FI65444B (fi)	1984-01-31
FR2430954B1 (da)	1984-08-17
DE2927733C2 (de)	1986-03-27
CA1124928A (en)	1982-06-01
AT369402B (de)	1982-12-27
DK293379A (da)	1980-01-14
DE2927733A1 (de)	1980-01-31
BE877653A (fr)	1979-11-05

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