CA1147328A - Salts of basic dyes, preparation and uses of same - Google Patents
Salts of basic dyes, preparation and uses of sameInfo
- Publication number
- CA1147328A CA1147328A CA000358024A CA358024A CA1147328A CA 1147328 A CA1147328 A CA 1147328A CA 000358024 A CA000358024 A CA 000358024A CA 358024 A CA358024 A CA 358024A CA 1147328 A CA1147328 A CA 1147328A
- Authority
- CA
- Canada
- Prior art keywords
- dye
- acid
- parts
- basic
- salts
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 83
- 239000000981 basic dye Substances 0.000 title abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000000975 dye Substances 0.000 claims abstract description 95
- 125000000129 anionic group Chemical group 0.000 claims abstract description 20
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000004327 boric acid Substances 0.000 claims abstract description 17
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 238000004043 dyeing Methods 0.000 claims description 27
- 150000001768 cations Chemical class 0.000 claims description 26
- 239000000976 ink Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 14
- 238000007639 printing Methods 0.000 claims description 13
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 239000000010 aprotic solvent Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000004922 lacquer Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
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- 239000000463 material Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229920002994 synthetic fiber Polymers 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
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- 229910052751 metal Inorganic materials 0.000 claims description 2
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- 150000001412 amines Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 239000013067 intermediate product Substances 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
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- 125000003010 ionic group Chemical group 0.000 claims 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 17
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- 230000008018 melting Effects 0.000 description 13
- 229960004889 salicylic acid Drugs 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 6
- QFIDXXOVFQZHDX-UHFFFAOYSA-J C(C=1C(O)=CC=CC1)(=O)[O-].[Na+].[B+3].C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-] Chemical compound C(C=1C(O)=CC=CC1)(=O)[O-].[Na+].[B+3].C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-].C(C=1C(O)=CC=CC1)(=O)[O-] QFIDXXOVFQZHDX-UHFFFAOYSA-J 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
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- 239000002798 polar solvent Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- UDHQWZLOKFJXDG-UHFFFAOYSA-N boric acid 2-hydroxybenzoic acid Chemical compound B(O)(O)O.C(C=1C(O)=CC=CC1)(=O)O.C(C=1C(O)=CC=CC1)(=O)O UDHQWZLOKFJXDG-UHFFFAOYSA-N 0.000 description 4
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 3
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 3
- TZXATTMVGZDPHM-UHFFFAOYSA-N 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium Chemical compound C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl TZXATTMVGZDPHM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 235000010980 cellulose Nutrition 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
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010016 exhaust dyeing Methods 0.000 description 3
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- 150000002334 glycols Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000010413 mother solution Substances 0.000 description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- VZOOHWGPNLPIHR-UHFFFAOYSA-N 3-[2-[[4-[bis(2-chloroethyl)amino]phenyl]diazenyl]-6-methoxy-1,3-benzothiazol-3-ium-3-yl]propanamide;chloride Chemical compound [Cl-].S1C2=CC(OC)=CC=C2[N+](CCC(N)=O)=C1N=NC1=CC=C(N(CCCl)CCCl)C=C1 VZOOHWGPNLPIHR-UHFFFAOYSA-N 0.000 description 2
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- IURGIPVDZKDLIX-UHFFFAOYSA-M [7-(diethylamino)phenoxazin-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](CC)CC)C=C2OC3=CC(N(CC)CC)=CC=C3N=C21 IURGIPVDZKDLIX-UHFFFAOYSA-M 0.000 description 2
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- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229910001411 inorganic cation Inorganic materials 0.000 description 2
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- 230000008022 sublimation Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0075—Preparations with cationic dyes
- C09B67/0076—Preparations of cationic or basic dyes in liquid form
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/607—Optical bleaching or brightening in organic solvents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/919—Paper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25061/79A IT1122748B (it) | 1979-08-10 | 1979-08-10 | Sali di coloranti basici,loro preparazione ed impieghi |
| IT25061A/79 | 1979-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1147328A true CA1147328A (en) | 1983-05-31 |
Family
ID=11215578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000358024A Expired CA1147328A (en) | 1979-08-10 | 1980-08-08 | Salts of basic dyes, preparation and uses of same |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4306875A (oth) |
| JP (1) | JPS5645959A (oth) |
| BE (1) | BE884694A (oth) |
| CA (1) | CA1147328A (oth) |
| CH (1) | CH652736A5 (oth) |
| DE (1) | DE3029581A1 (oth) |
| ES (1) | ES8106325A1 (oth) |
| FR (1) | FR2463166A1 (oth) |
| GB (1) | GB2065694B (oth) |
| IT (1) | IT1122748B (oth) |
| NL (1) | NL8004474A (oth) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5725364A (en) * | 1980-07-22 | 1982-02-10 | Showa Kagaku Kogyo Kk | Dyestuff salt |
| US4452604A (en) * | 1982-05-10 | 1984-06-05 | Armstrong World Industries, Inc. | Decorative sheets and coverings comprising polyvinyl chloride and cationic dyestuffs |
| US4763966A (en) * | 1984-07-16 | 1988-08-16 | Fuji Photo Film Co., Ltd. | Infrared absorbent |
| US4657590A (en) * | 1984-10-22 | 1987-04-14 | The First National Bank Of Cincinnati | Basic dye ink formulations and methods |
| JPS62174741A (ja) * | 1986-01-24 | 1987-07-31 | Fuji Photo Film Co Ltd | 有機基体物質を光に対して安定化する方法 |
| US5091004A (en) * | 1987-09-22 | 1992-02-25 | Dainippon Ink And Chemicals, Inc. | Ink composition |
| DE3833195A1 (de) * | 1988-09-30 | 1990-04-05 | Basf Ag | Verfahren zur herstellung konzentrierter loesungen kationischer farbstoffe |
| US5057393A (en) * | 1989-07-10 | 1991-10-15 | The Mead Corporation | Dye branched-alkyl borate photoinitiators |
| EP0447196A1 (en) * | 1990-03-16 | 1991-09-18 | Hewlett-Packard Company | Boronic acid dyes |
| JP3620097B2 (ja) * | 1995-04-28 | 2005-02-16 | 株式会社リコー | 水性インク |
| DE19517071A1 (de) * | 1995-05-10 | 1996-11-14 | Bayer Ag | Verfahren zur Herstellung von N,N'-disubstituierten 1,4-Diaminoanthrachinonen |
| JP4512809B2 (ja) * | 1999-04-20 | 2010-07-28 | 山田化学工業株式会社 | ポリメチン系色素化合物 |
| DE10122529A1 (de) * | 2001-05-09 | 2002-11-28 | Basf Drucksysteme Gmbh | Flexodruckfarbe zum Drucken von Steuermarkierungen |
| JP2005533915A (ja) * | 2002-07-26 | 2005-11-10 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 有機溶媒ベースの印刷インク |
| JP5428223B2 (ja) * | 2008-07-08 | 2014-02-26 | 山田化学工業株式会社 | 金属錯体色素及びディスプレイ用フィルタ |
| KR102104008B1 (ko) * | 2012-07-19 | 2020-04-23 | 스미또모 가가꾸 가부시키가이샤 | 염료용 염 |
| KR102284012B1 (ko) * | 2013-06-07 | 2021-07-30 | 동우 화인켐 주식회사 | 착색 경화성 수지 조성물 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE747583A (fr) | 1969-04-30 | 1970-08-31 | Sandoz Sa | Procede de preparation de sels de colorants |
| DE2130790C3 (de) * | 1971-06-22 | 1978-04-06 | Bayer Ag, 5090 Leverkusen | Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| BE786295A (fr) * | 1971-07-14 | 1973-01-15 | Bayer Ag | Colorants cationiques |
| BE787762A (fr) * | 1971-08-21 | 1973-02-19 | Bayer Ag | Colorants cationiques |
| DE2228147A1 (de) * | 1972-06-09 | 1973-12-20 | Bayer Ag | Kationische diazacyaninfarbstoffe |
| US4057388A (en) * | 1972-12-01 | 1977-11-08 | Ciba-Geigy Ag | Dry heat process for dyeing and printing organic material which can be dyed with cationic dyestuffs |
| GB1477324A (en) * | 1973-09-13 | 1977-06-22 | Sublistatic Holding Sa | Carriers and their use in printing and dyeing |
| DE2353537C3 (de) * | 1973-10-25 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Kationische Dimethinfarbstoffe, deren Herstellung und Verwendung zum Färben und Bedrucken von Polymerisaten oder Mischpolymerisaten des Acrylnitrils, von sauer modifizierten Polyestern und Polyamidmaterialien |
| CH632783A5 (de) * | 1977-12-28 | 1982-10-29 | Ciba Geigy Ag | Verfahren zur herstellung von loesungen von salzen wasserloeslicher carbonsaeuren kationischer farbstoffe bzw. optischer aufheller. |
-
1979
- 1979-08-10 IT IT25061/79A patent/IT1122748B/it active
-
1980
- 1980-08-05 GB GB8025528A patent/GB2065694B/en not_active Expired
- 1980-08-05 FR FR8017269A patent/FR2463166A1/fr active Granted
- 1980-08-05 DE DE19803029581 patent/DE3029581A1/de not_active Withdrawn
- 1980-08-05 US US06/175,598 patent/US4306875A/en not_active Expired - Lifetime
- 1980-08-06 JP JP10725580A patent/JPS5645959A/ja active Pending
- 1980-08-06 NL NL8004474A patent/NL8004474A/nl not_active Application Discontinuation
- 1980-08-08 BE BE0/201686A patent/BE884694A/fr not_active IP Right Cessation
- 1980-08-08 CH CH6026/80A patent/CH652736A5/it not_active IP Right Cessation
- 1980-08-08 CA CA000358024A patent/CA1147328A/en not_active Expired
- 1980-08-09 ES ES494145A patent/ES8106325A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL8004474A (nl) | 1981-02-12 |
| IT1122748B (it) | 1986-04-23 |
| JPS5645959A (en) | 1981-04-25 |
| FR2463166B1 (oth) | 1984-03-30 |
| IT7925061A0 (it) | 1979-08-10 |
| GB2065694B (en) | 1983-06-02 |
| ES494145A0 (es) | 1981-08-01 |
| DE3029581A1 (de) | 1981-02-26 |
| FR2463166A1 (fr) | 1981-02-20 |
| GB2065694A (en) | 1981-07-01 |
| CH652736A5 (it) | 1985-11-29 |
| ES8106325A1 (es) | 1981-08-01 |
| US4306875A (en) | 1981-12-22 |
| BE884694A (fr) | 1981-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |