DE2733178C2 - Verfahren zur Herstellung von Tetrachlorzinksalzen - Google Patents
Verfahren zur Herstellung von TetrachlorzinksalzenInfo
- Publication number
- DE2733178C2 DE2733178C2 DE2733178A DE2733178A DE2733178C2 DE 2733178 C2 DE2733178 C2 DE 2733178C2 DE 2733178 A DE2733178 A DE 2733178A DE 2733178 A DE2733178 A DE 2733178A DE 2733178 C2 DE2733178 C2 DE 2733178C2
- Authority
- DE
- Germany
- Prior art keywords
- zinc
- dye
- azo
- dialkyl sulfate
- alkylation
- 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
- 238000000034 method Methods 0.000 title claims description 21
- WLBHJIHRLZNSIV-UHFFFAOYSA-J dizinc tetrachloride Chemical class [Cl-].[Cl-].[Cl-].[Cl-].[Zn+2].[Zn+2] WLBHJIHRLZNSIV-UHFFFAOYSA-J 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 31
- 239000000987 azo dye Substances 0.000 claims description 23
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 20
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 150000003752 zinc compounds Chemical class 0.000 claims description 10
- 239000011787 zinc oxide Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 230000029936 alkylation Effects 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000005956 quaternization reaction Methods 0.000 claims description 5
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 4
- 229940007718 zinc hydroxide Drugs 0.000 claims description 4
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 4
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000011667 zinc carbonate Substances 0.000 claims description 3
- 235000004416 zinc carbonate Nutrition 0.000 claims description 3
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000005352 clarification Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- -1 benzothiazolium azo compound Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KVYNYRIOAYQBFK-JOEBSVEZSA-N (2s,3r)-n-[4-(diaminomethylideneamino)butyl]-5-[(e)-3-[4-(diaminomethylideneamino)butylamino]-3-oxoprop-1-enyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxamide Chemical compound C1([C@H]2OC3=CC=C(C=C3[C@H]2C(=O)NCCCCNC(N)=N)/C=C/C(=O)NCCCCNC(=N)N)=CC=C(O)C=C1 KVYNYRIOAYQBFK-JOEBSVEZSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- KLHYPYAETJWSBK-UHFFFAOYSA-J Cl[Zn](Cl)(Cl)Cl Chemical class Cl[Zn](Cl)(Cl)Cl KLHYPYAETJWSBK-UHFFFAOYSA-J 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ICGLOTCMOYCOTB-UHFFFAOYSA-N [Cl].[Zn] Chemical compound [Cl].[Zn] ICGLOTCMOYCOTB-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/005—Special process features in the quaternization reaction
-
- 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/20—Thiazoles or hydrogenated thiazoles
-
- 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
- C09B69/065—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids of cationic azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2733178A DE2733178C2 (de) | 1977-07-22 | 1977-07-22 | Verfahren zur Herstellung von Tetrachlorzinksalzen |
| CH779878A CH634594A5 (de) | 1977-07-22 | 1978-07-19 | Verfahren zur herstellung von chlorzinksalzen von benzthiazoliumazofarbstoffen. |
| MX174247A MX149712A (es) | 1977-07-22 | 1978-07-20 | Procedimiento para la obtencion de una sal de tetracloro zincato de un colorante azoico de benzotiazolio |
| IT25931/78A IT1097048B (it) | 1977-07-22 | 1978-07-20 | Processo per la preparazione di clorozincati di azo-coloranti di benzotiazolio |
| GB787830676A GB2001666B (en) | 1977-07-22 | 1978-07-21 | Process for the preparation of benzothiazolium azo compounds and chlorozincate salts thereof |
| NL7807823A NL7807823A (nl) | 1977-07-22 | 1978-07-21 | Werkwijze voor het bereiden van chloorzinkzouten van benzthiazoliumazokleurstoffen. |
| JP8851778A JPS5422439A (en) | 1977-07-22 | 1978-07-21 | Production of chlor zinc salt of benzthiazolium azo dyestuff |
| BR7804701A BR7804701A (pt) | 1977-07-22 | 1978-07-21 | Processo para a producao de sais de zinco e cloro de corantes azoicos de benzotiazolio |
| FR7821806A FR2398093A1 (fr) | 1977-07-22 | 1978-07-24 | Procede de preparation de sels de chlorure de zinc de colorants d'azobenzothiazolium |
| BE189455A BE869213A (fr) | 1977-07-22 | 1978-07-24 | Procede de preparation de sels de chlorure de zinc de colorants d'azo-benzothiazolium |
| US06/775,111 US4638053A (en) | 1977-07-22 | 1985-09-11 | Process for the preparation of chlorozincate salts of benzo thiazolium azo dyestuffs by alkylating with dialkylsulfate in aqueous medium in the presence of Zn-containing acid acceptor at pH≦7 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2733178A DE2733178C2 (de) | 1977-07-22 | 1977-07-22 | Verfahren zur Herstellung von Tetrachlorzinksalzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2733178B1 DE2733178B1 (de) | 1979-01-04 |
| DE2733178C2 true DE2733178C2 (de) | 1985-04-25 |
Family
ID=6014619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2733178A Expired DE2733178C2 (de) | 1977-07-22 | 1977-07-22 | Verfahren zur Herstellung von Tetrachlorzinksalzen |
Country Status (11)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840121C2 (de) * | 1978-09-15 | 1982-10-28 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Chlorzinksalzen von Thiazoliumazofarbstoffen |
| JPS59102808A (ja) * | 1982-12-02 | 1984-06-14 | Toagosei Chem Ind Co Ltd | 水不溶性リン酸塩の製造方法 |
| US4925926A (en) * | 1986-12-15 | 1990-05-15 | Ciba-Geigy Corporation | Preparation of cationic azo or hydrazone dyes in which the alkylation and the separation of the cationic dye are carried out continuously |
| ES2060997T3 (es) * | 1989-12-06 | 1994-12-01 | Ciba Geigy Ag | Procedimiento para teñir materiales de poliacrilonitrilo. |
| DE19964015A1 (de) * | 1999-12-30 | 2001-08-09 | Octapharma Ag Lachen | Verfahren zur Entfernung oder Abtrennung von Viren in potentiell Viren enthaltenden Proben |
| US20070191246A1 (en) * | 2006-01-23 | 2007-08-16 | Sivik Mark R | Laundry care compositions with thiazolium dye |
| US9796952B2 (en) * | 2012-09-25 | 2017-10-24 | The Procter & Gamble Company | Laundry care compositions with thiazolium dye |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889315A (en) * | 1954-12-15 | 1959-06-02 | Geigy Ag J R | Water soluble dye salts and process for the production thereof |
| FR1223107A (fr) * | 1958-11-03 | 1960-06-15 | Eureka Williams Corp | Accessoire d'aspirateur |
| BE695327A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-03-19 | 1967-08-14 | ||
| DE1943799A1 (de) * | 1968-09-18 | 1970-04-09 | Toms River Chemical Corp | Verfahren zur Alkylierung von Benzthiazolazoverbindungen |
| JPS4828529A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-08-19 | 1973-04-16 | ||
| US3936435A (en) * | 1974-08-08 | 1976-02-03 | Eastman Kodak Company | Cationic heterocyclic-azo-heterocyclic compounds from 5-aminoimidazo-(1,2-A)pyridines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE658939A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-02-01 | 1965-05-17 | ||
| CH501039A (de) * | 1968-07-29 | 1970-12-31 | Sandoz Ag | Verfahren zur Herstellung von basischen Monoazoverbindungen |
| GB1411243A (en) * | 1972-08-18 | 1975-10-22 | Ici Ltd | Water soluble azo dyestuffs |
| DE2255060A1 (de) * | 1972-11-10 | 1974-05-22 | Bayer Ag | Basische farbstoffe |
| US3991043A (en) * | 1973-01-23 | 1976-11-09 | Toms River Chemical Corporation | Quaternization of benzthiazole-azo compounds |
| PL89775B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-06-01 | 1976-12-31 | ||
| JPS5124529A (en) * | 1974-08-22 | 1976-02-27 | Kishiwada Tetsuko Kk | Senzaino sukeerujokyohoho oyobi sonosochi |
| GB1501882A (en) * | 1974-12-18 | 1978-02-22 | Ici Ltd | Cationic monoazo dyestuffs derived from dioxinobenzthiazoles |
| DE2553508A1 (de) * | 1975-11-28 | 1977-06-02 | Hoechst Ag | Basische azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| GB1533260A (en) * | 1976-11-08 | 1978-11-22 | Ici Ltd | Water soluble azo dyestuffs |
-
1977
- 1977-07-22 DE DE2733178A patent/DE2733178C2/de not_active Expired
-
1978
- 1978-07-19 CH CH779878A patent/CH634594A5/de not_active IP Right Cessation
- 1978-07-20 MX MX174247A patent/MX149712A/es unknown
- 1978-07-20 IT IT25931/78A patent/IT1097048B/it active
- 1978-07-21 BR BR7804701A patent/BR7804701A/pt unknown
- 1978-07-21 JP JP8851778A patent/JPS5422439A/ja active Pending
- 1978-07-21 GB GB787830676A patent/GB2001666B/en not_active Expired
- 1978-07-21 NL NL7807823A patent/NL7807823A/xx not_active Application Discontinuation
- 1978-07-24 FR FR7821806A patent/FR2398093A1/fr active Granted
- 1978-07-24 BE BE189455A patent/BE869213A/xx not_active IP Right Cessation
-
1985
- 1985-09-11 US US06/775,111 patent/US4638053A/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889315A (en) * | 1954-12-15 | 1959-06-02 | Geigy Ag J R | Water soluble dye salts and process for the production thereof |
| FR1223107A (fr) * | 1958-11-03 | 1960-06-15 | Eureka Williams Corp | Accessoire d'aspirateur |
| BE695327A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-03-19 | 1967-08-14 | ||
| DE1943799A1 (de) * | 1968-09-18 | 1970-04-09 | Toms River Chemical Corp | Verfahren zur Alkylierung von Benzthiazolazoverbindungen |
| JPS4828529A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-08-19 | 1973-04-16 | ||
| US3936435A (en) * | 1974-08-08 | 1976-02-03 | Eastman Kodak Company | Cationic heterocyclic-azo-heterocyclic compounds from 5-aminoimidazo-(1,2-A)pyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| MX149712A (es) | 1983-12-14 |
| JPS5422439A (en) | 1979-02-20 |
| IT1097048B (it) | 1985-08-26 |
| NL7807823A (nl) | 1979-01-24 |
| US4638053A (en) | 1987-01-20 |
| BR7804701A (pt) | 1979-04-17 |
| BE869213A (fr) | 1979-01-24 |
| IT7825931A0 (it) | 1978-07-20 |
| FR2398093A1 (fr) | 1979-02-16 |
| GB2001666B (en) | 1982-02-10 |
| CH634594A5 (de) | 1983-02-15 |
| DE2733178B1 (de) | 1979-01-04 |
| FR2398093B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-07-29 |
| GB2001666A (en) | 1979-02-07 |
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