CA1160625A - Process for the preparation of dyes which contain sulfonic acid groups and have a low electrolyte content - Google Patents
Process for the preparation of dyes which contain sulfonic acid groups and have a low electrolyte contentInfo
- Publication number
- CA1160625A CA1160625A CA000391269A CA391269A CA1160625A CA 1160625 A CA1160625 A CA 1160625A CA 000391269 A CA000391269 A CA 000391269A CA 391269 A CA391269 A CA 391269A CA 1160625 A CA1160625 A CA 1160625A
- Authority
- CA
- Canada
- Prior art keywords
- water
- dye
- amine
- parts
- sulfo group
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003792 electrolyte Substances 0.000 title claims abstract description 6
- 125000000542 sulfonic acid group Chemical group 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 13
- -1 amine salt Chemical class 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 7
- 150000008054 sulfonate salts Chemical class 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 239000012071 phase Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 150000003839 salts Chemical class 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 16
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 13
- 239000012530 fluid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZDTXQHVBLWYPHS-UHFFFAOYSA-N 4-nitrotoluene-2-sulfonic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O ZDTXQHVBLWYPHS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- RXRBXRIWFKOICY-UHFFFAOYSA-N N1=NN=C(C=C1)C(=C(C1=C(C(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O)C1=NN=NC=C1)C1=CC=CC=C1 Chemical class N1=NN=C(C=C1)C(=C(C1=C(C(=C(C=C1)N)S(=O)(=O)O)S(=O)(=O)O)C1=NN=NC=C1)C1=CC=CC=C1 RXRBXRIWFKOICY-UHFFFAOYSA-N 0.000 description 1
- 241001585714 Nola Species 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 150000001768 cations Chemical class 0.000 description 1
- ZBNARPCCDMHDDV-UHFFFAOYSA-N chembl1206040 Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S(O)(=O)=O)S(O)(=O)=O)C)=C(O)C2=C1N ZBNARPCCDMHDDV-UHFFFAOYSA-N 0.000 description 1
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
- WPWNIQBSYQVEKJ-UHFFFAOYSA-M chembl2028451 Chemical compound [Na+].CC1=CC(S([O-])(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-M 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940037395 electrolytes Drugs 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- WPWNIQBSYQVEKJ-UHFFFAOYSA-N sodium 4-[(2-hydroxynaphthalen-1-yl)diazenyl]-3-methylbenzenesulfonic acid Chemical compound [Na+].CC1=CC(S(O)(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 239000003643 water by type 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
- 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
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
-
- 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
-
- 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
- C09B67/0096—Purification; Precipitation; Filtration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803045377 DE3045377A1 (de) | 1980-12-02 | 1980-12-02 | Verfahren zur herstellung elektrolytarmer sulfonsaeuregruppenhaltiger farbstoffe |
| DEP3045377.1 | 1980-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160625A true CA1160625A (en) | 1984-01-17 |
Family
ID=6118094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000391269A Expired CA1160625A (en) | 1980-12-02 | 1981-12-01 | Process for the preparation of dyes which contain sulfonic acid groups and have a low electrolyte content |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4560745A (en, 2012) |
| EP (1) | EP0053220B1 (en, 2012) |
| JP (1) | JPS5796052A (en, 2012) |
| CA (1) | CA1160625A (en, 2012) |
| DE (2) | DE3045377A1 (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4502864A (en) * | 1984-04-25 | 1985-03-05 | Ciba-Geigy Corporation | Crown ether complexes of direct yellow 11 and dyestuff containing same |
| US4668774A (en) * | 1984-05-03 | 1987-05-26 | Basf Aktiengesellschaft | 2-ethylhexylamine salts of anionic monoazo dyes |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3462916D1 (en) * | 1983-03-04 | 1987-05-07 | Ciba Geigy Ag | Concentrated storage-stable aqueous solutions of yellow to greenish yellow stilbene azo or stilbene azoxy dyes |
| DE3344978A1 (de) * | 1983-12-13 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | Fluessige farbstoffsalze |
| US4617381A (en) * | 1984-09-11 | 1986-10-14 | Ciba-Geigy Corporation | Process for the preparation of concentrated stable liquid dye solutions of CI Direct Yellow 11 utilizing an alkanol/water solvent in a desalting procedure |
| CH660017A5 (de) * | 1984-11-12 | 1987-03-13 | Ciba Geigy Ag | Konzentrierte lagerstabile waessrige loesungen gelber stilbenazo(xy)farbstoffe. |
| JPS61173203A (ja) * | 1985-01-28 | 1986-08-04 | Sumitomo Chem Co Ltd | カラ−フィルタ−の製造法 |
| JPH01185372A (ja) * | 1988-01-18 | 1989-07-24 | Nippon Kayaku Co Ltd | 水不溶性黒色色素 |
| US5835294A (en) * | 1996-08-07 | 1998-11-10 | Minegishi; Norio | Wide-angle side-mirror device |
| DE19645105A1 (de) * | 1996-10-31 | 1998-05-07 | Basf Ag | Verfahren zur Herstellung von sulfonsäuregruppenhaltigen Cu-Phthalocyaninfarbstoffen |
| CH692246A5 (de) * | 1996-12-13 | 2002-04-15 | Basf Ag | Verfahren zur Herstellung von Aminsalzen von 4-Nitrotoluol-2-sulfonsäure. |
| KR100325880B1 (ko) * | 1997-02-14 | 2002-03-07 | 안 드와이트 | 세척가능한 착색 조성물 |
| US5900094A (en) * | 1997-02-14 | 1999-05-04 | Binney & Smith Inc. | Image transfer method for use with water based dry erase markers |
| US5981626A (en) * | 1997-02-14 | 1999-11-09 | Binney & Smith Inc. | Washable coloring composition suitable for use in dry erase markers |
| US6063175A (en) * | 1998-02-17 | 2000-05-16 | Milliken & Company | Triphenylmethane polymeric colorant having sterically hindered amine counter ion |
| US6096889A (en) * | 1999-06-01 | 2000-08-01 | Basf Corporation | Process for making high performance dyes |
| CA2373829A1 (en) * | 1999-06-02 | 2000-12-07 | Ciba Specialty Chemicals Holding Inc. | Novel yellow azo- and azoxystilbene dyes |
| DE502004011476D1 (de) * | 2003-12-22 | 2010-09-16 | Basf Se | Flüssigformulierungen von Direktfarbstoffen |
| JP2007262105A (ja) * | 2004-07-01 | 2007-10-11 | Nippon Kayaku Co Ltd | アゾ及び／又はアゾキシスチルベン染料の濃厚水溶液の製造法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956271A (en) * | 1969-01-20 | 1976-05-11 | Sandoz Ltd. | Process for the production of concentrated solutions of cationic azo dyes |
| US3719703A (en) * | 1969-04-29 | 1973-03-06 | Atomic Energy Commission | Separation of sulfonic acids from sulfuric acid |
| CH549088A (de) * | 1970-11-24 | 1974-05-15 | Ciba Geigy Ag | Verfahren zur herstellung von aminsalzen von reaktivfarbstoffen. |
| DE2115877B2 (de) * | 1971-04-01 | 1973-05-03 | Farbwerke Hoechst AG, vormals Mei ster Lucius & Brumng, 6000 Frankfurt | Verfahren zur herstellung von konzentrierten, stabilen fluessigeinstellungen von anionisch loeslichen optischen aufhellungsmitteln und farbstoffen |
| DE2451257C3 (de) * | 1974-10-29 | 1979-05-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von konzentrierten Farbstofflösungen und Verfahren zum Färben |
| JPS582976B2 (ja) * | 1975-08-06 | 1983-01-19 | タオカカガクコウギヨウ カブシキガイシヤ | スルホンサンキガンユウアゾセンリヨウノ セイゾウホウ |
| JPS52116438A (en) * | 1975-12-17 | 1977-09-29 | Toyo Soda Mfg Co Ltd | Preparation of styrene sulfonic acid salts |
| EP0021619A1 (en) * | 1979-06-12 | 1981-01-07 | Imperial Chemical Industries Plc | A method of making concentrated aqueous solutions of dyes and these solutions |
| DE2930491C2 (de) * | 1979-07-27 | 1987-01-02 | Olympia AG, 2940 Wilhelmshaven | Verfahren zum Erzeugen fremdsalzfreier Tinten |
-
1980
- 1980-12-02 DE DE19803045377 patent/DE3045377A1/de not_active Withdrawn
-
1981
- 1981-05-05 EP EP81103377A patent/EP0053220B1/de not_active Expired
- 1981-05-05 DE DE8181103377T patent/DE3161828D1/de not_active Expired
- 1981-05-12 US US06/263,007 patent/US4560745A/en not_active Expired - Lifetime
- 1981-05-29 JP JP56081266A patent/JPS5796052A/ja active Granted
- 1981-12-01 CA CA000391269A patent/CA1160625A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4502864A (en) * | 1984-04-25 | 1985-03-05 | Ciba-Geigy Corporation | Crown ether complexes of direct yellow 11 and dyestuff containing same |
| US4668774A (en) * | 1984-05-03 | 1987-05-26 | Basf Aktiengesellschaft | 2-ethylhexylamine salts of anionic monoazo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| US4560745A (en) | 1985-12-24 |
| JPH0220662B2 (en, 2012) | 1990-05-10 |
| EP0053220A1 (de) | 1982-06-09 |
| EP0053220B1 (de) | 1984-01-04 |
| DE3161828D1 (en) | 1984-02-09 |
| DE3045377A1 (de) | 1982-08-19 |
| JPS5796052A (en) | 1982-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1160625A (en) | Process for the preparation of dyes which contain sulfonic acid groups and have a low electrolyte content | |
| EP1283856B1 (en) | Process for preparing solutions of anionic organic compounds | |
| US4087245A (en) | Process for the preparation of concentrated solutions of anionic dyestuffs | |
| CH652736A5 (it) | Sali di coloranti basici, loro preparazione ed impieghi. | |
| DE2711150A1 (de) | Verfahren zur herstellung von azoreaktivfarbstoffen | |
| US5847113A (en) | Preparation of sulfo-containing copper phthalocyanine dyes | |
| EP0212345B1 (de) | Wässrige Farbstoffzubereitung, ihre Herstellung und Verwendung | |
| EP0922038B1 (de) | Verfahren zur herstellung von substituierten 4,4'-diaminostilben-2,2'-disulfonsäuresalzen | |
| US6719906B1 (en) | Process for the preparation of solutions of anionic organic compounds | |
| DE2451219C3 (de) | Verfahren zur Herstellung konzentrierter Lösungen von Farbstoffen und Farbstoffzwischenprodukten und Verwendung der Lösungen | |
| US4668789A (en) | Liquid dye salts | |
| EP0087703B1 (de) | Verfahren zur Herstellung von Reaktivfarbstoffpräparationen | |
| KR930010743B1 (ko) | 황색 아조 - 및 아족시스틸벤 염료의 저장안정성 농축 수용액의 제조방법 | |
| EP0681005B1 (de) | Triphendioxazin-Reaktivfarbstoffe | |
| US4077767A (en) | Process for the preparation of concentrated solutions of urea compounds | |
| GB1593859A (en) | Process for preparing concentrated aqueous solutions of phenylbenzthiazolmonoazo dyes | |
| EP0202775B1 (en) | Liquid dye preparations | |
| DE2743066A1 (de) | Farbstoffpraeparationen | |
| US4502864A (en) | Crown ether complexes of direct yellow 11 and dyestuff containing same | |
| DE3014662A1 (de) | Verfahren zur herstellung von wasserloeslichen phthalocyaninfarbstoffen | |
| US4314816A (en) | Direct blue dyes from the condensation of diaminostilbenedisulfonic acid with N-alkyl or N-hydroxyalkyl-8-amino-1-naphthol-3,6-disulfonic acid | |
| US994803A (en) | Dye. | |
| MXPA01012348A (es) | Proceso para preparar tintes de alta pureza. | |
| US4851516A (en) | Dyes from diazotized sulfonylaminoalkylphosphonic acids and naphtholdisulfonic acids | |
| US2205417A (en) | Nitrosamine addition product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |