CH368251A - Verfahren zur Herstellung von Farbstoffen - Google Patents

Verfahren zur Herstellung von Farbstoffen

Info

Publication number: CH368251A
Authority: CH; Switzerland
Prior art keywords: parts; dye; aldehyde; groups; formula
Prior art date: 1959-08-08

Application number

CH836360A

Other languages

German (de)

English (en)

Inventor

Roderich Dr Raue

Original Assignee

Bayer 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.)

1959-08-08

Filing date

1960-07-21

Publication date

1963-03-31

1960-07-21 Application filed by Bayer Ag filed Critical Bayer Ag

1963-03-31 Publication of CH368251A publication Critical patent/CH368251A/de

Links

238000000034 method Methods 0.000 title claims description 12
239000000975 dye Substances 0.000 title description 41
239000002253 acid Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
150000005840 aryl radicals Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
-1 heterocyclic radical Chemical class 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 5
239000003086 colorant Substances 0.000 claims description 4
150000007857 hydrazones Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
150000002429 hydrazines Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
150000003868 ammonium compounds Chemical class 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
235000002639 sodium chloride Nutrition 0.000 description 19
229920002239 polyacrylonitrile Polymers 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000463 material Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 9
MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 4
KSLJYMVWJQKOKG-UHFFFAOYSA-N 1-phenyl-N-(pyridin-2-ylmethylideneamino)methanamine Chemical compound C1(=CC=CC=C1)CNN=CC1=NC=CC=C1 KSLJYMVWJQKOKG-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
238000004043 dyeing Methods 0.000 description 4
239000004744 fabric Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
NQSIARGGPGHMCG-UHFFFAOYSA-N 1-ethyl-1-phenylhydrazine Chemical compound CCN(N)C1=CC=CC=C1 NQSIARGGPGHMCG-UHFFFAOYSA-N 0.000 description 3
CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BQDOMRFANBRPSZ-UHFFFAOYSA-N C1(=CC=CC=C1)CNN=CC1=NC2=CC=CC=C2C=C1 Chemical compound C1(=CC=CC=C1)CNN=CC1=NC2=CC=CC=C2C=C1 BQDOMRFANBRPSZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
229940008406 diethyl sulfate Drugs 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
IFARRRGGHHADCF-UHFFFAOYSA-N 1-ethyl-1-(4-methylphenyl)hydrazine Chemical compound CCN(N)C1=CC=C(C)C=C1 IFARRRGGHHADCF-UHFFFAOYSA-N 0.000 description 2
DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZENIIUAGMKRDNV-UHFFFAOYSA-N C(C1=NC2=CC=CC=C2C=C1)=NN(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C1=NC2=CC=CC=C2C=C1)=NN(C1=CC=CC=C1)C1=CC=CC=C1 ZENIIUAGMKRDNV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
RRUYZUKIYKHCNR-UHFFFAOYSA-N n-phenyl-n-(pyridin-2-ylmethylideneamino)aniline Chemical compound C=1C=CC=NC=1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 RRUYZUKIYKHCNR-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RHKPJTFLRQNNGJ-UHFFFAOYSA-N 1,3-benzothiazole-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=NC2=C1 RHKPJTFLRQNNGJ-UHFFFAOYSA-N 0.000 description 1
FBJHIKRTMNNHTQ-UHFFFAOYSA-N 1-(2-chloroethyl)-1-phenylhydrazine Chemical compound C1(=CC=CC=C1)N(N)CCCl FBJHIKRTMNNHTQ-UHFFFAOYSA-N 0.000 description 1
RRNWXJAWRPITPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-methylhydrazine Chemical compound CN(N)C1=CC=C(Cl)C=C1 RRNWXJAWRPITPU-UHFFFAOYSA-N 0.000 description 1
HZEHBAPKYPEFDS-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-methylhydrazine Chemical compound COC1=CC=C(N(C)N)C=C1 HZEHBAPKYPEFDS-UHFFFAOYSA-N 0.000 description 1
VKXUWCNLFZXHEF-UHFFFAOYSA-N 1-butyl-1-phenylhydrazine Chemical compound CCCCN(N)C1=CC=CC=C1 VKXUWCNLFZXHEF-UHFFFAOYSA-N 0.000 description 1
FFWWXLMIYACZCP-UHFFFAOYSA-N 1-cyclohexyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1CCCCC1 FFWWXLMIYACZCP-UHFFFAOYSA-N 0.000 description 1
TUFIMQRAQOQZOS-UHFFFAOYSA-N 1-methyl-1-(4-methylphenyl)hydrazine Chemical compound CN(N)C1=CC=C(C)C=C1 TUFIMQRAQOQZOS-UHFFFAOYSA-N 0.000 description 1
DQOSJWYZDQIMGM-UHFFFAOYSA-N 1H-benzimidazole-2-carbaldehyde Chemical compound C1=CC=C2NC(C=O)=NC2=C1 DQOSJWYZDQIMGM-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
MDISQESZDBPYRY-UHFFFAOYSA-N 6-chloroquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(Cl)=CC=C21 MDISQESZDBPYRY-UHFFFAOYSA-N 0.000 description 1
AYIIFDAAXPMDAG-UHFFFAOYSA-N 6-methoxyquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(OC)=CC=C21 AYIIFDAAXPMDAG-UHFFFAOYSA-N 0.000 description 1
BOUDHYSDNNTOQD-UHFFFAOYSA-N 6-nitroquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC([N+](=O)[O-])=CC=C21 BOUDHYSDNNTOQD-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
240000009038 Viola odorata Species 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
239000000981 basic dye Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
LGDPTPLJZGPOJL-UHFFFAOYSA-N n,n-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-UHFFFAOYSA-N 0.000 description 1
BCQMHPRJRFQRPW-UHFFFAOYSA-N n-methyl-n-(pyridin-2-ylmethylideneamino)aniline Chemical compound C=1C=CC=CC=1N(C)N=CC1=CC=CC=N1 BCQMHPRJRFQRPW-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000000123 paper Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000009466 transformation Effects 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
- C09B26/00—Hydrazone dyes; Triazene dyes
- C09B26/02—Hydrazone dyes
- C09B26/04—Hydrazone dyes cationic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH836360A 1959-08-08 1960-07-21 Verfahren zur Herstellung von Farbstoffen CH368251A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF29144A DE1150475B (de)	1959-08-08	1959-08-08	Verfahren zur Herstellung basischer Farbstoffe

Publications (1)

Publication Number	Publication Date
CH368251A true CH368251A (de)	1963-03-31

Family

ID=7093178

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH836360A CH368251A (de)	1959-08-08	1960-07-21	Verfahren zur Herstellung von Farbstoffen

Country Status (3)

Country	Link
BE (1)	BE593876R (fr)
CH (1)	CH368251A (fr)
DE (1)	DE1150475B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2340571C3 (de) *	1973-08-10	1982-01-21	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von heterocyclischen Verbindungen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1004748B (de)	1954-05-13	1957-03-21	Ciba Geigy	Verfahren zur Herstellung neuer Hydrazonfarbstoffe

1959
- 1959-08-08 DE DEF29144A patent/DE1150475B/de active Pending
1960
- 1960-07-21 CH CH836360A patent/CH368251A/de unknown
- 1960-08-08 BE BE593876A patent/BE593876R/fr active

Also Published As

Publication number	Publication date
DE1150475B (de)	1963-06-20
BE593876R (fr)	1960-12-01

Publication	Publication Date	Title
DE1065544B (de)	1959-09-17	Verfahren zur Herstellung von basischen Azofarbstoffen
DE2340571C3 (de)	1982-01-21	Verfahren zur Herstellung von heterocyclischen Verbindungen
DE2238378B2 (de)	1974-05-30	Perinonfarbstoffe und Verfahren zu ihrer Herstellung
DE2912428A1 (de)	1980-10-09	Neue dispersionsfarbstoffe, deren herstellung und verwendung
CH368251A (de)	1963-03-31	Verfahren zur Herstellung von Farbstoffen
DE1544469B1 (de)	1970-07-30	Verfahren zur Herstellung von Pyridazinazofarbstoffen,neue Pyridazinazofarbstoffe und deren Verwendung
AT223301B (de)	1962-09-10	Verfahren zur Herstellung basischer Hydrazonfarbstoffe
EP0111236A1 (fr)	1984-06-20	Colorants pyridoniques
DE2408012C2 (de)	1983-03-17	4-Amino-1,8-naphthalsäureimid-3-sulfonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe zum Färben von natürlichen oder synthetischen Polyamidfasern
DE1133054B (de)	1962-07-12	Verfahren zur Herstellung basischer Farbstoffe
AT223302B (de)	1962-09-10	Verfahren zur Herstellung neuer basischer Hydrazonfarbstoffe
DE2617807C2 (de)	1984-07-12	3-Amino-5-nitro-benzisothiazol-(2,1)-Derivate
DE2062678A1 (de)	1971-07-01	Neue Naphthahmidverbindungen, ihre Herstellung und Verwendung
AT223724B (de)	1962-10-10	Verfahren zur Herstellung von neuen Cyaninfarbstoffen
EP0037374B1 (fr)	1983-12-28	Composés méthiniques
AT206549B (de)	1959-12-10	Verfahren zur Herstellung neuer basischer Farbstoffe
DE1813241C3 (fr)	1978-02-02
DE1569696C3 (de)	1977-02-10	Wasserunlösliche Styrylfarbstoffe
AT220743B (de)	1962-04-10	Verfahren zur Herstellung von neuen Imidazolium-Azofarbstoffen
DE1133053B (de)	1962-07-12	Verfahren zur Herstellung basischer Farbstoffe
CH523955A (de)	1972-06-15	Verfahren zur Herstellung sulfonsäuregruppenfreier Azoverbindungen
AT235234B (de)	1964-08-10	Optische Aufhellungsmittel
DE1209679B (de)	1966-01-27	Verfahren zur Herstellung von basischen Farbstoffen
DE1103485B (de)	1961-03-30	Verfahren zur Herstellung basischer Styrylfarbstoffe
DE2055894A1 (en)	1972-05-18	Dyes from quadrate acid and pyrazolones - for colouring synthetic fri esp metal-modified polypropylene