CH502413A - Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen - Google Patents

Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen

Info

Publication number: CH502413A
Authority: CH; Switzerland
Prior art keywords: alkyl; formula; compound; water; hydroxyalkyl
Prior art date: 1966-03-03

Application number

CH312767A

Other languages

German (de)

English (en)

Inventor

Scibisz Halina

Gmaj Jan

Mielicki Jozef

Wojciechowski Lech

Original Assignee

Inst Przemyslu Organiczego

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.)

1966-03-03

Filing date

1967-03-03

Publication date

1971-01-31

1966-03-03 Priority claimed from PL113296A external-priority patent/PL56821B1/pl

1967-03-03 Application filed by Inst Przemyslu Organiczego filed Critical Inst Przemyslu Organiczego

1971-01-31 Publication of CH502413A publication Critical patent/CH502413A/de

Links

150000003242 quaternary ammonium salts Chemical class 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000000987 azo dye Substances 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
239000006172 buffering agent Substances 0.000 claims description 3
150000004982 aromatic amines Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
239000000395 magnesium oxide Substances 0.000 claims description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
238000005956 quaternization reaction Methods 0.000 claims 1
239000000975 dye Substances 0.000 abstract description 12
229920002239 polyacrylonitrile Polymers 0.000 abstract description 7
230000008878 coupling Effects 0.000 abstract description 6
238000010168 coupling process Methods 0.000 abstract description 6
238000005859 coupling reaction Methods 0.000 abstract description 6
238000000859 sublimation Methods 0.000 abstract description 5
230000008022 sublimation Effects 0.000 abstract description 5
238000004043 dyeing Methods 0.000 abstract description 4
150000001412 amines Chemical class 0.000 abstract 2
229910006069 SO3H Inorganic materials 0.000 abstract 1
229940100198 alkylating agent Drugs 0.000 abstract 1
239000002168 alkylating agent Substances 0.000 abstract 1
239000003086 colorant Substances 0.000 abstract 1
239000012458 free base Substances 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 1
239000000243 solution Substances 0.000 description 11
239000000835 fiber Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000008049 diazo compounds Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
230000001035 methylating effect Effects 0.000 description 2
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
JHRMJWGBGBDNJE-UHFFFAOYSA-N 1,3-benzothiazole-2,4-diamine Chemical compound C1=CC=C2SC(N)=NC2=C1N JHRMJWGBGBDNJE-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
LHRIICYSGQGXSX-UHFFFAOYSA-N 2-chloro-4,6-dinitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1[N+]([O-])=O LHRIICYSGQGXSX-UHFFFAOYSA-N 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
-1 phenylsulfonyl anion Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000003756 stirring 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
- C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group

Landscapes

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

CH312767A 1966-03-03 1967-03-03 Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen CH502413A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL113296A PL56821B1 (fr)		1966-03-03

Publications (1)

Publication Number	Publication Date
CH502413A true CH502413A (de)	1971-01-31

Family

ID=19949434

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH312767A CH502413A (de)	1966-03-03	1967-03-03	Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen

Country Status (5)

Country	Link
BE (1)	BE694938A (fr)
CH (1)	CH502413A (fr)
DE (1)	DE1644279A1 (fr)
GB (1)	GB1133683A (fr)
NL (1)	NL6703423A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4072672A (en) *	1972-07-31	1978-02-07	Sandoz Ltd.	Cationic dyes containing an aryloxy group linked through a bridging radical to a quaternized nitrogen atom
DD113239A5 (fr) *	1973-02-26	1975-05-20
EP0514336B1 (fr) *	1991-05-17	1996-12-11	Ciba-Geigy Ag	Procédé de préparation de solutions aqueuses hautement concentrées de colorants azoiques cationiques

1967
- 1967-03-02 BE BE694938D patent/BE694938A/xx unknown
- 1967-03-02 DE DE19671644279 patent/DE1644279A1/de active Pending
- 1967-03-02 NL NL6703423A patent/NL6703423A/xx unknown
- 1967-03-03 CH CH312767A patent/CH502413A/de not_active IP Right Cessation
- 1967-03-03 GB GB1008867A patent/GB1133683A/en not_active Expired

Also Published As

Publication number	Publication date
BE694938A (fr)	1967-08-14
GB1133683A (en)	1968-11-13
NL6703423A (fr)	1967-09-04
DE1644279A1 (de)	1971-07-15

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Legal Events

Date	Code	Title	Description
1971-12-31	PL	Patent ceased