CH620700A5 - Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure - Google Patents

Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure Download PDF

Info

Publication number: CH620700A5
Authority: CH; Switzerland
Prior art keywords: bromo; nitro; methoxycarbonylethyl; dye; chloro
Prior art date: 1975-09-01

Application number

CH1102376A

Other languages

German (de)

English (en)

Inventor

Peter William Barker

Michael Edmondson

Original Assignee

Ici Ltd

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.)

1975-09-01

Filing date

1976-08-31

Publication date

1980-12-15

1976-08-31 Application filed by Ici Ltd filed Critical Ici Ltd

1980-12-15 Publication of CH620700A5 publication Critical patent/CH620700A5/de

Links

238000000034 method Methods 0.000 title claims description 13
239000013078 crystal Substances 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 4
239000007788 liquid Substances 0.000 claims description 16
-1 azo compound Chemical class 0.000 claims description 14
238000002441 X-ray diffraction Methods 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
239000002609 medium Substances 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 7
238000010586 diagram Methods 0.000 claims description 6
239000012736 aqueous medium Substances 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims 1
239000000975 dye Substances 0.000 description 25
239000006185 dispersion Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
GLUCALKKMFBJEB-UHFFFAOYSA-N 2-bromo-6-chloro-4-nitroaniline Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Br GLUCALKKMFBJEB-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
239000004753 textile Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000004043 dyeing Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
NQMXUYSFHRWLLV-UHFFFAOYSA-N methyl 3-(n-(3-methoxy-3-oxopropyl)anilino)propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)C1=CC=CC=C1 NQMXUYSFHRWLLV-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000004040 coloring Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000227 grinding Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
DQBNLFRFALCILS-UHFFFAOYSA-N 1-[(2-sulfonaphthalen-1-yl)methyl]naphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3S(=O)(=O)O)=C(S(O)(=O)=O)C=CC2=C1 DQBNLFRFALCILS-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000011282 treatment 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
- 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
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds

Landscapes

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

CH1102376A 1975-09-01 1976-08-31 Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure CH620700A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3594875A GB1543316A (en)	1975-09-01	1975-09-01	Stabilised disperse azo dyestuff

Publications (1)

Publication Number	Publication Date
CH620700A5 true CH620700A5 (en)	1980-12-15

Family

ID=10383284

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1102376A CH620700A5 (en)	1975-09-01	1976-08-31	Process for the preparation of 2-bromo-4'-nitro-6-chloro-4-(N,N-di(beta-methoxycarbonylethyl)amino)az obenzene having a novel crystal structure

Country Status (12)

Country	Link
JP (1)	JPS5229822A (fr)
AR (1)	AR210156A1 (fr)
BE (1)	BE845511A (fr)
BR (1)	BR7605768A (fr)
CH (1)	CH620700A5 (fr)
DE (1)	DE2639401C3 (fr)
ES (1)	ES451146A1 (fr)
FR (1)	FR2322175A1 (fr)
GB (1)	GB1543316A (fr)
IT (1)	IT1064973B (fr)
NL (1)	NL7609436A (fr)
TR (1)	TR19366A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2918567A1 (de) *	1979-05-09	1980-11-20	Hoechst Ag	Kondensate aus addukten von phosphiten und propen-2-olen und deren herstellung
DE2921210A1 (de)	1979-05-25	1980-12-04	Hoechst Ag	Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung
DE2950588A1 (de) *	1979-12-15	1981-06-19	Hoechst Ag, 6230 Frankfurt	Faerbestabiler monoazofarbstoff, dessen herstellung und verwendung
US4329144A (en)	1979-12-27	1982-05-11	Ciba-Geigy Corporation	Disperse dye stable to dyeing, and its use for dyeing and printing synthetic and semi-synthetic fibre materials
US4327999A (en)	1980-01-09	1982-05-04	Ciba-Geigy Corporation	Disperse dye stable to dyeing, and its use for dyeing synthetic and semi-synthetic fibre materials
US4332588A (en)	1980-01-11	1982-06-01	Ciba-Geigy Corporation	Disperse dye stable to dyeing, and its use for dyeing and printing synthetic and semi-synthetic fibre materials
US4388078A (en)	1982-03-24	1983-06-14	Mobay Chemical Corporation	Anthraquinone dyestuff modification
JPS58225156A (ja) *	1982-06-21	1983-12-27	Gosei Senriyou Gijutsu Kenkyu Kumiai	モノアゾ染料及びその製法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2007382A (en) *	1932-08-16	1935-07-09	Celanese Corp	Production of dispersions
DE734846C (de) *	1939-03-04	1943-05-10	Ig Farbenindustrie Ag	Verfahren zur Herstellung von Azofarbstoffen
DE1619535A1 (de) *	1967-07-19	1971-05-19	Bayer Ag	Faerbestabile Dispersionsfarbstoffe
CH559767A5 (en) *	1972-12-12	1975-03-14	Sandoz Ag	Azo-dispersion dye in beta-modification and prodn. - by prepn. and conditioning at relatively low temp., for continuous dyeing
DE2336717A1 (de) *	1973-07-19	1975-02-06	Basf Ag	Dispersionsstabile modifikation eines dispersionsfarbstoffs

1975
- 1975-09-01 GB GB3594875A patent/GB1543316A/en not_active Expired
1976
- 1976-08-25 BE BE170071A patent/BE845511A/fr unknown
- 1976-08-25 NL NL7609436A patent/NL7609436A/xx not_active Application Discontinuation
- 1976-08-26 IT IT2658076A patent/IT1064973B/it active
- 1976-08-30 AR AR26450876A patent/AR210156A1/es active
- 1976-08-31 CH CH1102376A patent/CH620700A5/de not_active IP Right Cessation
- 1976-08-31 FR FR7626256A patent/FR2322175A1/fr active Pending
- 1976-08-31 BR BR7605768A patent/BR7605768A/pt unknown
- 1976-09-01 TR TR1936676A patent/TR19366A/xx unknown
- 1976-09-01 JP JP10541476A patent/JPS5229822A/ja active Pending
- 1976-09-01 DE DE19762639401 patent/DE2639401C3/de not_active Expired
- 1976-09-01 ES ES451146A patent/ES451146A1/es not_active Expired

Also Published As

Publication number	Publication date
BE845511A (fr)	1977-02-25
AR210156A1 (es)	1977-06-30
BR7605768A (pt)	1977-08-23
DE2639401C3 (de)	1982-02-04
JPS5229822A (en)	1977-03-07
FR2322175A1 (fr)	1977-03-25
NL7609436A (nl)	1977-03-03
TR19366A (tr)	1979-01-22
GB1543316A (en)	1979-04-04
DE2639401A1 (de)	1977-04-21
DE2639401B2 (de)	1981-01-15
IT1064973B (it)	1985-02-25
ES451146A1 (es)	1977-08-16

Legal Events

Date	Code	Title	Description
1982-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0019831A1 (fr)	1980-12-10	Modification cristallographique stable d'un colorant monoazoique, sa préparation et son utilisation pour la teinture de fibres
DE2639401C3 (de)	1982-02-04	2-Brom-4-nitro-6-chlor-4'-[N,N-di-(β-methoxycarbonyläthyl)-amino]-azobenzol und Verfahren zu seiner Herstellung
DE2347532B1 (de)	1975-03-13	Monoazopigmente,Verfahren zu ihrer Herstellung und ihre Verwendung
EP0045276B1 (fr)	1983-06-22	Colorants complexes de chrome et de cobalt 1:2
DE1150046B (de)	1963-06-12	Verfahren zur Umwandlung der Kristallstruktur von linearem Rohchinacridon in die reine ª‰-Kristallphase
DE1769443C3 (de)	1978-09-07	Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Druckfarben
DE2729915A1 (de)	1978-01-19	Gemische von 1 zu 2-kobaltkomplexazoverbindungen, deren herstellung und verwendung
AT166451B (de)	1950-08-10	Verfahren zur Herstellung neuer chromhaltiger Monoazofarbstoffe
DE2110349C3 (de)	1974-07-04	Monoazopigment, Verfahren zu seiner Herstellung und Verwendung
DE1298661B (de)	1969-07-03	Verfahren zur Herstellung in Wasser schwer loeslicher Dispersionsfarbstoffe
DE2317532C2 (de)	1975-01-30	Monoazoplgment, Verfahren zu seiner Herstellung und seine Verwendung
DE2735376A1 (de)	1978-03-02	Stabilisierter disperser azofarbstoff
DE2824829A1 (de)	1979-02-08	Verfahren zum faerben von synthetischen textilien
DE2125099B2 (de)	1973-07-26	Marineblaue dispersions-disazofarbstoffe, deren herstellung und verwendung
EP0187916A2 (fr)	1986-07-23	Modification stable d'un colorant de dispersion, son procédé de fabrication et son utilisation
DE2224447C3 (de)	1976-11-25	Pyridonfarbstorf-Modifikation, deren Herstellung und deren Verwendung zum Färben von Polyester
DE2336717A1 (de)	1975-02-06	Dispersionsstabile modifikation eines dispersionsfarbstoffs
DE3322301A1 (de)	1984-01-05	Monoazofarbstoff und verfahren zu dessen herstellung
DE2511534B1 (de)	1976-09-02	Faerbestabiler monoazofarbstoff, dessen herstellung und dessen verwendung
DE1644167C3 (fr)	1974-05-22
AT278192B (de)	1970-01-26	Verfahren zur Herstellung von neuen, wasserunlöslichen Monoazofarbstoffen
DE2043483C3 (de)	1973-10-11	Wasserunlösliche Monoazofarb stoffe, Verfahren zu ihrer Herstellung und Verwendung
DE2756331A1 (de)	1979-06-21	Azofarbstoffe
DD298189A7 (de)	1992-02-13	Verfahren zur herstellung eines bordoroten azopigments mit verbesserter farbstaerke
DE1219145B (de)	1966-06-16	Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe