DE2152257A1 - Verfahren zur Herstellung in Wasser schwerloeslicher Verbindungen - Google Patents

Verfahren zur Herstellung in Wasser schwerloeslicher Verbindungen

Info

Publication number: DE2152257A1
Authority: DE; Germany
Prior art keywords: formula; compounds; free; yellow; atoms
Prior art date: 1970-10-22
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.): Pending

Application number

DE19712152257

Other languages

German (de)

English (en)

Inventor

Dr Kaul Bans Lal

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz 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.)

1970-10-22

Filing date

1971-10-20

Publication date

1972-04-27

1970-10-22 Priority claimed from CH1557170A external-priority patent/CH540323A/de

1970-12-01 Priority claimed from CH1777370A external-priority patent/CH542905A/de

1971-10-20 Application filed by Sandoz AG filed Critical Sandoz AG

1972-04-27 Publication of DE2152257A1 publication Critical patent/DE2152257A1/de

Status Pending legal-status Critical Current

Links

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239000000986 disperse dye Substances 0.000 title description 3
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 2
241000394567 Viola pubescens Species 0.000 title 1
229920002994 synthetic fiber Polymers 0.000 title 1
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
125000005842 heteroatom Chemical group 0.000 claims abstract description 11
125000004429 atom Chemical group 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 10
125000000542 sulfonic acid group Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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239000003795 chemical substances by application Substances 0.000 claims description 3
238000004040 coloring Methods 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
125000002843 carboxylic acid group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract description 7
229910052760 oxygen Inorganic materials 0.000 abstract description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 57
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239000000049 pigment Substances 0.000 description 9
239000000975 dye Substances 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
229920000915 polyvinyl chloride Polymers 0.000 description 7
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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150000003254 radicals Chemical class 0.000 description 6
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
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239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
235000000177 Indigofera tinctoria Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
230000003750 conditioning effect Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
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238000010992 reflux Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
238000004061 bleaching Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000835 fiber Substances 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000004753 textile Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910019213 POCl3 Inorganic materials 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
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239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Chemical class 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical compound [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002237 fumaric acid derivatives Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000000976 ink Substances 0.000 description 1
239000002649 leather substitute Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
229910052751 metal Chemical group 0.000 description 1
239000002184 metal Chemical group 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc 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
- C09B57/00—Other synthetic dyes of known constitution

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)

DE19712152257 1970-10-22 1971-10-20 Verfahren zur Herstellung in Wasser schwerloeslicher Verbindungen Pending DE2152257A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1557170A CH540323A (de)	1970-10-22	1970-10-22	Verfahren zur Herstellung in Wasser schwer löslicher Verbindungen
CH1777370A CH542905A (de)	1970-12-01	1970-12-01	Verfahren zur Herstellung schwer löslicher heterocyclischer Verbindungen

Publications (1)

Publication Number	Publication Date
DE2152257A1 true DE2152257A1 (de)	1972-04-27

Family

ID=25716623

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19712152257 Pending DE2152257A1 (de)	1970-10-22	1971-10-20	Verfahren zur Herstellung in Wasser schwerloeslicher Verbindungen

Country Status (2)

Country	Link
BE (1)	BE773969A (fr)
DE (1)	DE2152257A1 (fr)

1971
- 1971-10-14 BE BE773969A patent/BE773969A/fr unknown
- 1971-10-20 DE DE19712152257 patent/DE2152257A1/de active Pending

Also Published As

Publication number	Publication date
BE773969A (fr)	1972-01-31

Publication	Publication Date	Title
DE2263235A1 (de)	1973-07-12	Heterocyclische metallkomplexverbindungen, ihre herstellung und verwendung
DE1156527B (de)	1963-10-31	Verfahren zur Herstellung von Anthrachinonkuepenfarbstoffen
DE1277476B (de)	1968-09-12	Verfahren zur Herstellung von Farbstoffen
CH622278A5 (fr)	1981-03-31
DE2152257A1 (de)	1972-04-27	Verfahren zur Herstellung in Wasser schwerloeslicher Verbindungen
DE2151723B2 (de)	1973-09-20	Indigoide Pigmente, ihre Herste! lung und Verwendung
EP0017621A1 (fr)	1980-10-15	Dérivés du naphtolactame, leur procédé de préparation et leur utilisation comme colorants
DE2533428A1 (de)	1977-02-10	Kationische farbstoffe
CH512564A (de)	1971-09-15	Verfahren zur Herstellung von Monoazoverbindungen
CH516628A (de)	1971-12-15	Farbstoffpräparate, welche wasserunlösliche Styrylfarbstoffe enthalten
CH540323A (de)	1973-08-15	Verfahren zur Herstellung in Wasser schwer löslicher Verbindungen
EP0037374B1 (fr)	1983-12-28	Composés méthiniques
CH542905A (de)	1973-10-15	Verfahren zur Herstellung schwer löslicher heterocyclischer Verbindungen
CH558415A (de)	1975-01-31	Verfahren zur herstellung von naphthochinonverbindungen.
DE1963356A1 (de)	1971-06-24	Chinophthalon-Farbstoffe
DE2020299A1 (de)	1971-11-11	Perinonfarbstoffe
DE2447229A1 (de)	1976-04-15	Styrylfarbstoffe
DE2059708B2 (de)	1975-05-15	Monoazopigmente der beta - Hydroxynaphthoesäurereihe, Verfahren zu deren Herstellung und ihre Verwendung
CH549626A (de)	1974-05-31	Verfahren zur herstellung schwer loeslicher, heterocyclischer verbindungen.
DE2342815A1 (de)	1975-04-24	Neue dioxazinfarbstoffe
DE2454549A1 (de)	1975-06-05	Heterocyclische verbindungen, ihre herstellung und verwendung
CH517156A (de)	1971-12-31	Verfahren zur Herstellung von Verbindungen der heterocyclischen Reihe
AT234872B (de)	1964-07-27	Verfahren zur Herstellung neuer Küpenfarbstoffe
CH561261A5 (en)	1975-04-30	Heterocyclic polynuclear pigments - of phenylene, naphthylene, perylene or benzophenone series, for synthetics, coatings, fibres, paper, printing
CH560244A5 (en)	1975-03-27	Triazolyl-styryl derivs. useful as optical brighteners - by reacting 2-phenyl-4-styryl-1,2,3-triazole-4',4"-dicarboxylic acid with aniline derivative