CH632527A5 - Process for preparing a stable, concentrated aqueous dye solution - Google Patents

Process for preparing a stable, concentrated aqueous dye solution Download PDF

Info

Publication number: CH632527A5
Authority: CH; Switzerland
Prior art keywords: amine; formula; stable; tertiary amine; dye
Prior art date: 1976-12-09

Application number

CH1489777A

Other languages

German (de)

English (en)

Inventor

John David Dr Hildreth

David Geoffrey Haslam

Original Assignee

Ciba Geigy Ag

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.)

1976-12-09

Filing date

1977-12-06

Publication date

1982-10-15

1977-12-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-10-15 Publication of CH632527A5 publication Critical patent/CH632527A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 8
239000000203 mixture Substances 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
238000000034 method Methods 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
150000003512 tertiary amines Chemical class 0.000 claims description 8
-1 methoxyethyl Chemical group 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
239000004202 carbamide Substances 0.000 claims description 5
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
239000000470 constituent Substances 0.000 claims description 4
238000004043 dyeing Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
239000012954 diazonium Substances 0.000 claims description 2
150000001989 diazonium salts Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000006277 sulfonation reaction Methods 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims 2
239000000975 dye Substances 0.000 description 29
239000000243 solution Substances 0.000 description 25
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
239000012065 filter cake Substances 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003860 storage Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003866 tertiary ammonium salts Chemical class 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 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 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical group CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N methylguanidine Chemical compound CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000005185 salting out Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003419 tautomerization reaction Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
UGQBKQLRGMYYQP-UHFFFAOYSA-N 2,2,2-trimethoxyethanamine Chemical compound COC(CN)(OC)OC UGQBKQLRGMYYQP-UHFFFAOYSA-N 0.000 description 1
XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
YDIKCZBMBPOGFT-PWUSVEHZSA-N Malvidin 3-galactoside Chemical compound [Cl-].COC1=C(O)C(OC)=CC(C=2C(=CC=3C(O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)=C1 YDIKCZBMBPOGFT-PWUSVEHZSA-N 0.000 description 1
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
229910003202 NH4 Inorganic materials 0.000 description 1
PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
BLNJZMQZYXWQGM-UHFFFAOYSA-N carbamoyl azide Chemical class NC(=O)N=[N+]=[N-] BLNJZMQZYXWQGM-UHFFFAOYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001470 diamides Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000006101 laboratory sample Substances 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 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
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 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
- C09B67/0073—Preparations of acid or reactive 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- 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
- C09B69/045—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds of anionic azo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paper (AREA)

CH1489777A 1976-12-09 1977-12-06 Process for preparing a stable, concentrated aqueous dye solution CH632527A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5146276A GB1593859A (en)	1976-12-09	1976-12-09	Process for preparing concentrated aqueous solutions of phenylbenzthiazolmonoazo dyes

Publications (1)

Publication Number	Publication Date
CH632527A5 true CH632527A5 (en)	1982-10-15

Family

ID=10460118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1489777A CH632527A5 (en)	1976-12-09	1977-12-06	Process for preparing a stable, concentrated aqueous dye solution

Country Status (9)

Country	Link
JP (1)	JPS5381528A (fr)
BE (1)	BE861624A (fr)
BR (1)	BR7708176A (fr)
CH (1)	CH632527A5 (fr)
DE (1)	DE2754486A1 (fr)
ES (1)	ES464845A1 (fr)
FR (1)	FR2373586A1 (fr)
GB (1)	GB1593859A (fr)
NL (1)	NL7713441A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2949517A1 (de) *	1979-12-08	1981-06-25	Bayer Ag, 5090 Leverkusen	Konzentrierte waessrige loesungen von monoazofarbstoffen und deren verwendung zum faerben von papier
DE3434921A1 (de) *	1984-09-22	1986-05-07	Sandoz-Patent-GmbH, 7850 Lörrach	Heterocyclische monoazoverbindungen
DE3743235A1 (de) *	1987-12-19	1989-06-29	Bayer Ag	Basische farbstoffe
EP0369940B1 (fr) *	1988-11-15	1995-05-31	Ciba-Geigy Ag	Solutions concentrées de colorants
DE4030915A1 (de) *	1990-09-29	1992-04-02	Basf Ag	Konzentrierte waessrige loesungen von 2-phenylbenzthiazolazofarbstoffen
DK1470196T3 (da) *	2002-01-28	2005-06-20	Ciba Sc Holding Ag	Vandige farvestofoplösninger

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA918643A (en) *	1970-10-19	1973-01-09	Blackwell John	Green-yellow monazo paper dyes derived from barbituric acid

1976
- 1976-12-09 GB GB5146276A patent/GB1593859A/en not_active Expired
1977
- 1977-12-05 NL NL7713441A patent/NL7713441A/xx not_active Application Discontinuation
- 1977-12-06 CH CH1489777A patent/CH632527A5/de not_active IP Right Cessation
- 1977-12-07 DE DE19772754486 patent/DE2754486A1/de active Pending
- 1977-12-07 ES ES464845A patent/ES464845A1/es not_active Expired
- 1977-12-07 FR FR7736911A patent/FR2373586A1/fr active Granted
- 1977-12-08 BR BR7708176A patent/BR7708176A/pt unknown
- 1977-12-08 BE BE183266A patent/BE861624A/fr unknown
- 1977-12-09 JP JP14733877A patent/JPS5381528A/ja active Pending

Also Published As

Publication number	Publication date
JPS5381528A (en)	1978-07-19
BE861624A (fr)	1978-06-08
GB1593859A (en)	1981-07-22
DE2754486A1 (de)	1978-10-26
FR2373586A1 (fr)	1978-07-07
FR2373586B1 (fr)	1980-06-13
BR7708176A (pt)	1978-08-08
NL7713441A (nl)	1978-06-13
ES464845A1 (es)	1978-08-01

Legal Events

Date	Code	Title	Description
1984-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2139311B2 (de)	1974-12-19	Verfahren zur einstufigen Herstellung von Azofarbstoffen
DE60126268T2 (de)	2007-05-31	Verfahren zur herstellung von lösungen anionischer organischer verbindungen
DE2854974A1 (de)	1980-07-10	Rekristallisationsstabile farbstarke monoazopigmentgemische, verfahren zu ihrer herstellung und ihre verwendung
DE2503714B2 (de)	1977-08-11	Verfahren zur herstellung von wasserloeslichen azofarbstoffen
CH634091A5 (de)	1983-01-14	Verfahren zur herstellung eines aminosaeure-farbstoffsalzes.
CH620238A5 (fr)	1980-11-14
CH632527A5 (en)	1982-10-15	Process for preparing a stable, concentrated aqueous dye solution
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