CA1094055A - Colorants azoiques insolubles dans l'eau - Google Patents

Colorants azoiques insolubles dans l'eau

Info

Publication number: CA1094055A
Authority: CA; Canada
Prior art keywords: formula; dyes; parts; printed; water
Prior art date: 1977-11-22
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.): Expired

Application number

CA316,558A

Other languages

English (en)

Inventor

Gioacchino Boffa

Flavio Villani

Romano Gianola

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.)

Aziende Colori Nazionali Affini ACNA SpA

Original Assignee

Aziende Colori Nazionali Affini ACNA SpA

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.)

1977-11-22

Filing date

1978-11-21

Publication date

1981-01-20

1978-11-21 Application filed by Aziende Colori Nazionali Affini ACNA SpA filed Critical Aziende Colori Nazionali Affini ACNA SpA

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094055A publication Critical patent/CA1094055A/fr

Status Expired legal-status Critical Current

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 13
239000000987 azo dye Substances 0.000 title 1
239000000975 dye Substances 0.000 claims abstract description 30
238000004043 dyeing Methods 0.000 claims abstract description 11
239000012209 synthetic fiber Substances 0.000 claims abstract description 6
229920002994 synthetic fiber Polymers 0.000 claims abstract description 6
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 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
229920000728 polyester Polymers 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000835 fiber Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
159000000011 group IA salts Chemical class 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
230000002209 hydrophobic effect Effects 0.000 claims 3
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 2
239000007810 chemical reaction solvent Substances 0.000 claims 1
WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical class OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 abstract description 2
239000000543 intermediate Substances 0.000 description 19
238000006467 substitution reaction Methods 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
239000004744 fabric Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000011282 treatment Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
-1 e.g. Substances 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000859 sublimation Methods 0.000 description 3
230000008022 sublimation Effects 0.000 description 3
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
JJHVYGVVMBYCMQ-UHFFFAOYSA-N 6-hydroxy-4-methyl-1h-pyridin-2-one Chemical group CC=1C=C(O)NC(=O)C=1 JJHVYGVVMBYCMQ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000986 disperse dye Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000010025 steaming Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
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
JRPYLONXEYCUNV-UHFFFAOYSA-N 2,2-dimethylpropyl 2-chloroacetate Chemical compound CC(C)(C)COC(=O)CCl JRPYLONXEYCUNV-UHFFFAOYSA-N 0.000 description 1
RLFIWYGMZQJEFO-UHFFFAOYSA-N 2-chloro-n-cyclohexylacetamide Chemical compound ClCC(=O)NC1CCCCC1 RLFIWYGMZQJEFO-UHFFFAOYSA-N 0.000 description 1
AIEPOEZPSFETKH-UHFFFAOYSA-N 2-chloroacetic acid piperidine-1-carboxamide Chemical compound N1(CCCCC1)C(=O)N.ClCC(=O)O AIEPOEZPSFETKH-UHFFFAOYSA-N 0.000 description 1
BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000005415 aminobenzoic acids Chemical group 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
238000006149 azo coupling reaction Methods 0.000 description 1
YJRGMUWRPCPLNH-UHFFFAOYSA-N butyl 2-chloroacetate Chemical compound CCCCOC(=O)CCl YJRGMUWRPCPLNH-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
239000002245 particle Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000002562 thickening agent 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
- 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
- C09B29/3617—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 with only one nitrogen as heteroatom
- C09B29/3621—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 with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—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 with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/15—Locally discharging the dyes
- D06P5/17—Azo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Dispersion Chemistry (AREA)
Coloring (AREA)

CA316,558A 1977-11-22 1978-11-21 Colorants azoiques insolubles dans l'eau Expired CA1094055A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2989077A IT1088895B (it)	1977-11-22	1977-11-22	Coloranti monozoici idroinsolubili
IT29890A/77		1977-11-22

Publications (1)

Publication Number	Publication Date
CA1094055A true CA1094055A (fr)	1981-01-20

Family

ID=11228622

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA316,558A Expired CA1094055A (fr)	1977-11-22	1978-11-21	Colorants azoiques insolubles dans l'eau

Country Status (10)

Country	Link
JP (1)	JPS5480330A (fr)
BE (1)	BE872213A (fr)
CA (1)	CA1094055A (fr)
CH (1)	CH634089A5 (fr)
DE (1)	DE2850390A1 (fr)
ES (1)	ES475254A1 (fr)
FR (1)	FR2409290A1 (fr)
GB (1)	GB2008606B (fr)
IT (1)	IT1088895B (fr)
NL (1)	NL7811354A (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2966849B2 (ja) *	1987-12-03	1999-10-25	三井化学株式会社	黄色系昇華転写用色材
FR2734274B1 (fr) *	1995-05-17	1997-11-14	Clariant Finance Bvi Ltd	Nouveaux composes azoiques, leur preparation et leur utilisation comme colorants de dispersion
US6663703B1 (en)	2002-06-27	2003-12-16	Xerox Corporation	Phase change inks containing dimeric azo pyridone colorants
US6590082B1 (en)	2002-06-27	2003-07-08	Xerox Corporation	Azo pyridone colorants
US6576747B1 (en)	2002-06-27	2003-06-10	Xerox Corporation	Processes for preparing dianthranilate compounds and diazopyridone colorants
US6696552B2 (en)	2002-06-27	2004-02-24	Xerox Corporation	Process for preparing substituted pyridone compounds
US6755902B2 (en)	2002-06-27	2004-06-29	Xerox Corporation	Phase change inks containing azo pyridone colorants
US6576748B1 (en)	2002-06-27	2003-06-10	Xerox Corporation	Method for making dimeric azo pyridone colorants
US6673139B1 (en)	2002-06-27	2004-01-06	Xerox Corporation	Phase change inks containing dimeric azo pyridone colorants
US6646111B1 (en)	2002-06-27	2003-11-11	Xerox Corporation	Dimeric azo pyridone colorants
US7381253B2 (en)	2004-12-03	2008-06-03	Xerox Corporation	Multi-chromophoric azo pyridone colorants
JP2009280691A (ja) *	2008-05-22	2009-12-03	Sumitomo Chemical Co Ltd	アゾ化合物又はその塩

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE789191A (fr) *	1971-09-24	1973-03-22	Cassella Farbwerke Mainkur Ag	Colorants mono-azoiques insolubles dans l'eau
DE2438497A1 (de) *	1974-08-10	1976-02-26	Bayer Ag	Azofarbstoffe

1977
- 1977-11-22 IT IT2989077A patent/IT1088895B/it active
1978
- 1978-11-17 NL NL7811354A patent/NL7811354A/xx not_active Application Discontinuation
- 1978-11-20 FR FR7832619A patent/FR2409290A1/fr active Granted
- 1978-11-20 CH CH1188978A patent/CH634089A5/it not_active IP Right Cessation
- 1978-11-21 GB GB7845445A patent/GB2008606B/en not_active Expired
- 1978-11-21 ES ES475254A patent/ES475254A1/es not_active Expired
- 1978-11-21 DE DE19782850390 patent/DE2850390A1/de not_active Withdrawn
- 1978-11-21 CA CA316,558A patent/CA1094055A/fr not_active Expired
- 1978-11-21 JP JP14294378A patent/JPS5480330A/ja active Pending
- 1978-11-22 BE BE191885A patent/BE872213A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2850390A1 (de)	1979-05-23
GB2008606A (en)	1979-06-06
IT1088895B (it)	1985-06-10
JPS5480330A (en)	1979-06-27
ES475254A1 (es)	1979-04-16
BE872213A (fr)	1979-05-22
CH634089A5 (it)	1983-01-14
FR2409290B1 (fr)	1981-06-12
FR2409290A1 (fr)	1979-06-15
NL7811354A (nl)	1979-05-25
GB2008606B (en)	1982-04-28

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
CA1094055A (fr)	1981-01-20	Colorants azoiques insolubles dans l'eau
KR100674493B1 (ko)	2007-02-05	프탈이미딜 아조 염료 및 이의 제조방법
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