DE2206551C3 - Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Papier sowie naturlicher und regenerierter Cellulose - Google Patents
Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Papier sowie naturlicher und regenerierter CelluloseInfo
- Publication number
- DE2206551C3 DE2206551C3 DE2206551A DE2206551A DE2206551C3 DE 2206551 C3 DE2206551 C3 DE 2206551C3 DE 2206551 A DE2206551 A DE 2206551A DE 2206551 A DE2206551 A DE 2206551A DE 2206551 C3 DE2206551 C3 DE 2206551C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dye
- formula
- water
- dyeing
- 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
- 239000000987 azo dye Substances 0.000 title claims description 9
- 238000004043 dyeing Methods 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000004627 regenerated cellulose Substances 0.000 title description 3
- 239000000975 dye Substances 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 7
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 150000008049 diazo compounds Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 naphthyl radical Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- RNBXVHYQKFVFKG-UHFFFAOYSA-N 6-(3-oxobutanoylamino)naphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)CC(=O)C)=CC=C21 RNBXVHYQKFVFKG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- KGZUHYIHYBDNLC-UHFFFAOYSA-N 2-(4-aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Chemical compound S1C2=C(S(O)(=O)=O)C(C)=CC=C2N=C1C1=CC=C(N)C=C1 KGZUHYIHYBDNLC-UHFFFAOYSA-N 0.000 description 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
- SGFXNJIQRFEOIA-UHFFFAOYSA-N 2-amino-5-(6-methyl-1,3-benzothiazol-2-yl)benzenesulfonic acid Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C(S(O)(=O)=O)=C1 SGFXNJIQRFEOIA-UHFFFAOYSA-N 0.000 description 1
- PRLIMMHXFBMDPL-UHFFFAOYSA-N 4-(3-oxobutanoylamino)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(NC(=O)CC(=O)C)=CC=C(S(O)(=O)=O)C2=C1 PRLIMMHXFBMDPL-UHFFFAOYSA-N 0.000 description 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- LKVXQCKDIYHFGZ-UHFFFAOYSA-N n-naphthalen-1-yl-3-oxobutanamide Chemical compound C1=CC=C2C(NC(=O)CC(=O)C)=CC=CC2=C1 LKVXQCKDIYHFGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- C09B67/0072—Preparations with anionic dyes or reactive dyes
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH225071A CH554397A (de) | 1971-02-16 | 1971-02-16 | Verfahren zur herstellung von azofarbstoffen. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2206551A1 DE2206551A1 (de) | 1972-08-31 |
| DE2206551B2 DE2206551B2 (de) | 1977-10-27 |
| DE2206551C3 true DE2206551C3 (de) | 1978-07-20 |
Family
ID=4229372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206551A Expired DE2206551C3 (de) | 1971-02-16 | 1972-02-11 | Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von Papier sowie naturlicher und regenerierter Cellulose |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4001206A (enExample) |
| JP (1) | JPS5713589B1 (enExample) |
| AU (1) | AU467338B2 (enExample) |
| BE (1) | BE779345A (enExample) |
| BR (1) | BR7200768D0 (enExample) |
| CA (1) | CA975356A (enExample) |
| CH (1) | CH554397A (enExample) |
| DD (1) | DD100966A5 (enExample) |
| DE (1) | DE2206551C3 (enExample) |
| ES (1) | ES399765A1 (enExample) |
| FR (1) | FR2125457B1 (enExample) |
| GB (1) | GB1380994A (enExample) |
| HK (1) | HK30077A (enExample) |
| IT (1) | IT947572B (enExample) |
| NL (1) | NL174061C (enExample) |
| SE (3) | SE390177B (enExample) |
| SU (1) | SU470971A3 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2702584C2 (de) * | 1977-01-22 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen |
| DE2738510C3 (de) * | 1977-08-26 | 1980-06-12 | Bayer Ag, 5090 Leverkusen | Wasserlösliche Mono- und Disazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung zum Färben und Bedrucken von Zellulosefasermaterialien |
| DE2821350A1 (de) * | 1978-05-16 | 1979-11-22 | Cassella Ag | Wasserloesliche monoazofarbstoffe, ihre herstellung, verwendung und damit gefaerbte und bedruckte materialien |
| US4400319A (en) * | 1980-10-03 | 1983-08-23 | Ciba-Geigy Corporation | Monoazo pigments containing heterocycles, and high-molecular organic materials dyed therewith |
| GB8423017D0 (en) * | 1984-09-12 | 1984-10-17 | Plessey Co Plc | Echo canceller |
| DE3443595A1 (de) * | 1984-11-29 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | Monoazofarbstoffe |
| DE3443594A1 (de) * | 1984-11-29 | 1986-05-28 | Bayer Ag, 5090 Leverkusen | Aminophenylbenzthiazole |
| US4894447A (en) * | 1986-04-16 | 1990-01-16 | Ciba-Geigy Corporation | Surflonated azo dyes containing a diazo component consisting of a two ring heterocycle with an aminophenylene group |
| DE3735078A1 (de) * | 1987-10-16 | 1989-04-27 | Cassella Ag | Wasserloesliche gelbe monoazofarbstoffe |
| DE59107782D1 (de) * | 1990-04-03 | 1996-06-13 | Ciba Geigy Ag | Konzentrierte Farbstofflösungen |
| WO2005103163A2 (en) * | 2004-04-27 | 2005-11-03 | Ciba Specialty Chemicals Holding Inc. | Salts of laked monoazo compounds |
| CN101711267B (zh) * | 2007-05-23 | 2013-04-24 | 克莱里安特财务(Bvi)有限公司 | 稳定的液体制剂 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1159386A (en) * | 1914-11-05 | 1915-11-09 | Synthetic Patents Co Inc | Yellow azo dye. |
| US2857373A (en) * | 1955-03-01 | 1958-10-21 | Eastman Kodak Co | Benzothiazole azo compounds containing a reactive methylene coupling component |
| US3274171A (en) * | 1963-04-29 | 1966-09-20 | Allied Chem | Monoazo dyestuffs containing a benzothiazole nucleus |
| US3451820A (en) * | 1965-12-01 | 1969-06-24 | Du Pont | Dispersions of lipophilic colorcoupling copolymers |
-
1971
- 1971-02-16 CH CH225071A patent/CH554397A/xx not_active IP Right Cessation
-
1972
- 1972-02-10 BR BR768/72A patent/BR7200768D0/pt unknown
- 1972-02-11 GB GB647772A patent/GB1380994A/en not_active Expired
- 1972-02-11 US US05/225,629 patent/US4001206A/en not_active Expired - Lifetime
- 1972-02-11 DE DE2206551A patent/DE2206551C3/de not_active Expired
- 1972-02-14 SU SU1745931A patent/SU470971A3/ru active
- 1972-02-14 ES ES399765A patent/ES399765A1/es not_active Expired
- 1972-02-14 SE SE7412677A patent/SE390177B/xx unknown
- 1972-02-14 SE SE7201712A patent/SE380820B/xx unknown
- 1972-02-14 BE BE779345A patent/BE779345A/xx unknown
- 1972-02-15 JP JP1527472A patent/JPS5713589B1/ja active Pending
- 1972-02-15 DD DD160922A patent/DD100966A5/xx unknown
- 1972-02-15 AU AU39010/72A patent/AU467338B2/en not_active Expired
- 1972-02-15 IT IT20576/72A patent/IT947572B/it active
- 1972-02-15 FR FR7204920A patent/FR2125457B1/fr not_active Expired
- 1972-02-15 CA CA134,714A patent/CA975356A/en not_active Expired
- 1972-02-16 NL NLAANVRAGE7202012,A patent/NL174061C/xx not_active IP Right Cessation
-
1974
- 1974-10-09 SE SE7412677A patent/SE7412677L/xx unknown
-
1977
- 1977-06-09 HK HK300/77A patent/HK30077A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU470971A3 (ru) | 1975-05-15 |
| FR2125457A1 (enExample) | 1972-09-29 |
| SE380820B (sv) | 1975-11-17 |
| BE779345A (fr) | 1972-08-14 |
| SE7412677L (enExample) | 1974-10-09 |
| NL174061B (nl) | 1983-11-16 |
| NL174061C (nl) | 1984-04-16 |
| CA975356A (en) | 1975-09-30 |
| CH554397A (de) | 1974-09-30 |
| JPS5713589B1 (enExample) | 1982-03-18 |
| HK30077A (en) | 1977-06-17 |
| DE2206551B2 (de) | 1977-10-27 |
| AU467338B2 (en) | 1973-08-16 |
| SE390177B (sv) | 1976-12-06 |
| BR7200768D0 (pt) | 1973-06-12 |
| NL7202012A (enExample) | 1972-08-18 |
| US4001206A (en) | 1977-01-04 |
| DD100966A5 (enExample) | 1973-10-12 |
| ES399765A1 (es) | 1975-07-16 |
| GB1380994A (en) | 1975-01-22 |
| DE2206551A1 (de) | 1972-08-31 |
| FR2125457B1 (enExample) | 1981-02-13 |
| IT947572B (it) | 1973-05-30 |
| AU3901072A (en) | 1973-08-16 |
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