CA1185755A - Dyeing formulations, process for their manufacture and their use for the dyeing and printing of synthetic fiber materials - Google Patents
Dyeing formulations, process for their manufacture and their use for the dyeing and printing of synthetic fiber materialsInfo
- Publication number
- CA1185755A CA1185755A CA000403951A CA403951A CA1185755A CA 1185755 A CA1185755 A CA 1185755A CA 000403951 A CA000403951 A CA 000403951A CA 403951 A CA403951 A CA 403951A CA 1185755 A CA1185755 A CA 1185755A
- Authority
- CA
- Canada
- Prior art keywords
- dyeing
- dyestuff
- formula
- parts
- printing
- Prior art date
- 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
Links
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
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- 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
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
-
- 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
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Abstract of the disclosure:
Subject of the present invention are novel dyeing formu-lations the dyestuff portion of which is a mixture of dyestuffs of the formula (1) ( 1 )
Subject of the present invention are novel dyeing formu-lations the dyestuff portion of which is a mixture of dyestuffs of the formula (1) ( 1 )
Description
575~i
- 2 - ~IOE ~1/F 132 Subject of the present invention are novel dyeing formulations the dyestuff portion of which is a mixture of dyestuffs of the formula (1) ~ 2 2 ~ 2 2 ~ N-N~ = R1 (1) in which X is a chlorine or bromine atom, R1 is a hydrogen atom or an alkyl group haviny -from 1 to 4 carbon atoms, and R2 and R3, independently of each other, represent a methyl or ethyl group; a process for their manufacture, and their use for the dyeiny or printing of synthetlc fiber materials.
It has been found that dyeing formulations the dye-stu~f portion of which consists of a mixture of dyestuffs of the above formula (1), yield dyeing baths havina very good tinctorial properties. Especially dyeings of wound packages, for examp]e cross-wound bobblns, so obtained are ~ree from dyestuff deposits on the goods. Further-more, the color build-up is very good, the sensitivi.ty to reduction and to temperature variation on dyeing is low. The dyeing formulations are suitable for high-speed dyeing processes and for the dyeing of the polyester ~5 portions in fiber mixtures.
The dyestuff mixtures required for the dyeing formu-lations oE the invention are prepared in known manner by coupllng diazotized 2,4~dinitro-6-chloraniline or diazotized 2,4-dinitro-6-bromaniline or a mixture thereof 30 with a mixture of coupling components of the formula (2~
.
OC2~ 40R2 ~ N / .
~ ~1 NHCOR
. 3 .. ~ .. ,. ,= .. . ...... . . . . .. . . . . . ... . .. .. .
75i~
It has been found that dyeing formulations the dye-stu~f portion of which consists of a mixture of dyestuffs of the above formula (1), yield dyeing baths havina very good tinctorial properties. Especially dyeings of wound packages, for examp]e cross-wound bobblns, so obtained are ~ree from dyestuff deposits on the goods. Further-more, the color build-up is very good, the sensitivi.ty to reduction and to temperature variation on dyeing is low. The dyeing formulations are suitable for high-speed dyeing processes and for the dyeing of the polyester ~5 portions in fiber mixtures.
The dyestuff mixtures required for the dyeing formu-lations oE the invention are prepared in known manner by coupllng diazotized 2,4~dinitro-6-chloraniline or diazotized 2,4-dinitro-6-bromaniline or a mixture thereof 30 with a mixture of coupling components of the formula (2~
.
OC2~ 40R2 ~ N / .
~ ~1 NHCOR
. 3 .. ~ .. ,. ,= .. . ...... . . . . .. . . . . . ... . .. .. .
75i~
- 3 - HOE 81/F 132 in which ~1 through R3 are as defined above sub ~ormula 11), in an acidic, aqueous solution.
The dyeing formulations are manufactured from the dyestuff mixtures by ~rinding the latter ones in wet state together with dispersing agents, for example ligninsulfo-nates. Alternatively, the sepa ately prepared dyestuffs are subjected to wet grinding with dispersing agents, and the components are mixed before, during or after the grinding operation.
Synthetic fiber materials which can be dyed or printed with the use of the dyeing formulations according to the invention are for example polyamide, cellulose 2 1/2-acetate or cellulose triacetate, and especially polyester fiber materialsO Corresponding suitable fiber mixtures are for example blends of polyester fibers and wool or polyester fibers and cotton.
The dyestuffs used for the manufacture o the dyeing formula-tions of the inven-tion are described in Belgian Patent No. 634,032 and in German Patents Nos. 2,736,785 and 2,833,854.
The following Examples illustrate the invention.
E X A M P L E
__ ___ _ ___ 217.5 Parts by weight of 2,4-dinitro-6-chloraniline are introduced into 1,000 parts by weight of 96 % sulfuric acid, and dissolved with stirring. Subsequently, 320 parts by weight of 40 % nitrosylsulfuric acid are poured in, while maintaining the temperature at 30-35C by external cooling~ Stirring is continued for a further 2 hours at thi~ temperature, after which period o~ time diazotiza-tion is complete. The diazonium salt solution so obtainedis poured within 60 minutes into a mixture of 4,000 parts by weight of water, 6,000 parts by weight of ice, 1,000 parts by weight of glacial acetic acid, ~7 parts by weight of 2-ethylamino-4-propionylamino-1-B-methoxy-ethoxybenzene, 17 parts by wei~ht of 2-amino-4-propionyl-amino~ -methoxy-ethoxybenzene, 165 parts by weight of 2-ethylamino-4-acetylamlno-1-B-methoxy ethoxybenzene and 32 parts by weight of 2-amino-4-acetamino-1-B methoxy-ethoxybenzene, while stirring. ~he temperature must not
The dyeing formulations are manufactured from the dyestuff mixtures by ~rinding the latter ones in wet state together with dispersing agents, for example ligninsulfo-nates. Alternatively, the sepa ately prepared dyestuffs are subjected to wet grinding with dispersing agents, and the components are mixed before, during or after the grinding operation.
Synthetic fiber materials which can be dyed or printed with the use of the dyeing formulations according to the invention are for example polyamide, cellulose 2 1/2-acetate or cellulose triacetate, and especially polyester fiber materialsO Corresponding suitable fiber mixtures are for example blends of polyester fibers and wool or polyester fibers and cotton.
The dyestuffs used for the manufacture o the dyeing formula-tions of the inven-tion are described in Belgian Patent No. 634,032 and in German Patents Nos. 2,736,785 and 2,833,854.
The following Examples illustrate the invention.
E X A M P L E
__ ___ _ ___ 217.5 Parts by weight of 2,4-dinitro-6-chloraniline are introduced into 1,000 parts by weight of 96 % sulfuric acid, and dissolved with stirring. Subsequently, 320 parts by weight of 40 % nitrosylsulfuric acid are poured in, while maintaining the temperature at 30-35C by external cooling~ Stirring is continued for a further 2 hours at thi~ temperature, after which period o~ time diazotiza-tion is complete. The diazonium salt solution so obtainedis poured within 60 minutes into a mixture of 4,000 parts by weight of water, 6,000 parts by weight of ice, 1,000 parts by weight of glacial acetic acid, ~7 parts by weight of 2-ethylamino-4-propionylamino-1-B-methoxy-ethoxybenzene, 17 parts by wei~ht of 2-amino-4-propionyl-amino~ -methoxy-ethoxybenzene, 165 parts by weight of 2-ethylamino-4-acetylamlno-1-B-methoxy ethoxybenzene and 32 parts by weight of 2-amino-4-acetamino-1-B methoxy-ethoxybenzene, while stirring. ~he temperature must not
- 4 - HO~ 81_F 132 exceed 5C, which is ensured by aclcdition of further ice.
Stirring is continued for ~ hours, the dyes-tuff mixture ~ormed is i.1tered off and washed with water until it ls free from acid. About 1,100 parts by weight of filter cake containing 390 parts by weight of dyestuff mixture are obtained.
The filter cake is pasted with 400 parts by weight of sodium ligninsulfonate and 200 parts by weight of water, and homogeni.zed. Subsequently, it is ground in a bead mill until the dis-tribution is sufficiently fine. Wi.th the use of 900 par-ts by weigh-t of water the dyeing formula-tion is now separated from the beads and adjusted to 2,600 parts b.7 weight. The dyeing formulation so ob-tained is pourable and, after incorporation in dyeing liquors, padding baths or printing pastes, yields even dyeings or prints having very good fastnesses, especially very good fastness to rubbing, on polyester fiber materials.
The formulation is especially suitable for high-speed dyeing p.rocesses. ~he dyeings have a very good co:lor ~0 bui.3.d-up.
The amount of dyestuff in the dyeing formulation is a total 15 % and has the following composition:
Dyestuff of the formula 25NO2 oc2H~locH3 O2N ~ N=N ~/ ~ NHC2H5 55 Cl NHCOCH3 dyestuff of the formula r2~ 2 ~ 3 ~ NH2 12 %, Cl NHCOCH 3 ~s~
Stirring is continued for ~ hours, the dyes-tuff mixture ~ormed is i.1tered off and washed with water until it ls free from acid. About 1,100 parts by weight of filter cake containing 390 parts by weight of dyestuff mixture are obtained.
The filter cake is pasted with 400 parts by weight of sodium ligninsulfonate and 200 parts by weight of water, and homogeni.zed. Subsequently, it is ground in a bead mill until the dis-tribution is sufficiently fine. Wi.th the use of 900 par-ts by weigh-t of water the dyeing formula-tion is now separated from the beads and adjusted to 2,600 parts b.7 weight. The dyeing formulation so ob-tained is pourable and, after incorporation in dyeing liquors, padding baths or printing pastes, yields even dyeings or prints having very good fastnesses, especially very good fastness to rubbing, on polyester fiber materials.
The formulation is especially suitable for high-speed dyeing p.rocesses. ~he dyeings have a very good co:lor ~0 bui.3.d-up.
The amount of dyestuff in the dyeing formulation is a total 15 % and has the following composition:
Dyestuff of the formula 25NO2 oc2H~locH3 O2N ~ N=N ~/ ~ NHC2H5 55 Cl NHCOCH3 dyestuff of the formula r2~ 2 ~ 3 ~ NH2 12 %, Cl NHCOCH 3 ~s~
- 5 -HOE 81~F 132 dyestuff of the formula /NO2 OC~H40CH3 S 2~ ~ N=N ~ -~HC2H5 27 Cl NHCOC2H5 dyestuff of the foxmula NO
~r / OC2~ 0C~3 ~2N ~ -N=N - ~ - NH2 6 %.
Cl ~HCOC2H5 When for the preparation of the dyestuff mixture a mixture of 108.75 parts by weight of 2,~-dinitro-6-chlor-aniline and 131 parts by weight of 2,4-dinitro-5-bromani-line is used instead of 217.5 parts by weiyht of 2,4-d.i.nitro-6-cil].oraniline, and the operations are as indi-cated, a dyeing formulation having very good tinctorial properties, too, is obtained. The dyestuf L portion of this formulation contains 8 dyestuffs.
150 Parts by weight of the dyestuff of the formula M02 OC2H~ocH3 2 ~ ~ ~ / CH(CH3~2 Cl ~IICOC2ll5~
150 parts by weight of the dyestuff of the formula ~l~cH3)2 Cl NHCOC~i3 ;755
~r / OC2~ 0C~3 ~2N ~ -N=N - ~ - NH2 6 %.
Cl ~HCOC2H5 When for the preparation of the dyestuff mixture a mixture of 108.75 parts by weight of 2,~-dinitro-6-chlor-aniline and 131 parts by weight of 2,4-dinitro-5-bromani-line is used instead of 217.5 parts by weiyht of 2,4-d.i.nitro-6-cil].oraniline, and the operations are as indi-cated, a dyeing formulation having very good tinctorial properties, too, is obtained. The dyestuf L portion of this formulation contains 8 dyestuffs.
150 Parts by weight of the dyestuff of the formula M02 OC2H~ocH3 2 ~ ~ ~ / CH(CH3~2 Cl ~IICOC2ll5~
150 parts by weight of the dyestuff of the formula ~l~cH3)2 Cl NHCOC~i3 ;755
- 6 - HOE 8 /F 132 and 450 parts by weight of a condensation procluct of m-cresol, ~ormaldehyde and sodium bisulfite are pasted with 800 parts of water and ~omogenized. Subsequently, the batch is ~round in a bead mill, until the distribution is sufficiently fine. Tne ground paste obtained is spray-dried and adjusted to a dyestuff content of 35 % by adding further dispersing agent, for example sodium ligninsulfo-nate. The dyeing formlllation so obtained yields dyeing liquors having very good tinctorial properties, for example a very good color build-up. The dyeing formula-tion is especially suitable for high-speed dyeing processes.
The blue dyeings obtained on polyester or polyamide fiber materials are distinquished by a very good evenness, and by very good fastnesses, especially a very good fastness to rubbinc.
Further dyelng formulations according to the inven-tion contain the following dyestuff mixtures; percentages being relative to the dyestuff portion of the formulations.
E X A M P L E 3_ _ ~0 A dyeing foxmu].ation the dyestuff ~ortion of which has the followi.ng composition:
43 % dyestuff of the formula O2N ~ - N=N ~ N~ICHtCH3)2 C l NHCHCH 3
The blue dyeings obtained on polyester or polyamide fiber materials are distinquished by a very good evenness, and by very good fastnesses, especially a very good fastness to rubbinc.
Further dyelng formulations according to the inven-tion contain the following dyestuff mixtures; percentages being relative to the dyestuff portion of the formulations.
E X A M P L E 3_ _ ~0 A dyeing foxmu].ation the dyestuff ~ortion of which has the followi.ng composition:
43 % dyestuff of the formula O2N ~ - N=N ~ N~ICHtCH3)2 C l NHCHCH 3
7 ~ dyestuff o the formula ~ 2 ~ 2 4 2 5 ~l NHCOCH3 .
~ .. ~ . .... .. ...... . . ... . .. .
~ 5~
- 7 - _IOE 81/F 132 43 % dyestuff of th~ forrnula ~2 2 ~ 2 5 2~- C \~ N=N ~ N~ICH(CI~3)~
NHcoc2H5 - 7 % d~estu~f of the formula ~2 oc2H4oc2Hs - 2 ~ -N-N - ~ NH~
Cl NHcoc2H5 . .
A dyeing formulation the dyestuff portion of which is composed as follows:
60 % dyestu~ o the formula O2N - ~ - N=N ~ \~ -NH-CH / 3 Bx NHCOCH3 40 % dyestuff of the formula O2N-- ~ N-N - ~ NH-CH
Br NHCOC2H5 __ . __ A dye.ing ormulation the dyestuff portion of which 35 is composed as follows:
. ~ , . . .. . . . . .. .. . .. .. . ., .. .... ... . , . ~ . . . ... ~
5~7~i5
~ .. ~ . .... .. ...... . . ... . .. .
~ 5~
- 7 - _IOE 81/F 132 43 % dyestuff of th~ forrnula ~2 2 ~ 2 5 2~- C \~ N=N ~ N~ICH(CI~3)~
NHcoc2H5 - 7 % d~estu~f of the formula ~2 oc2H4oc2Hs - 2 ~ -N-N - ~ NH~
Cl NHcoc2H5 . .
A dyeing formulation the dyestuff portion of which is composed as follows:
60 % dyestu~ o the formula O2N - ~ - N=N ~ \~ -NH-CH / 3 Bx NHCOCH3 40 % dyestuff of the formula O2N-- ~ N-N - ~ NH-CH
Br NHCOC2H5 __ . __ A dye.ing ormulation the dyestuff portion of which 35 is composed as follows:
. ~ , . . .. . . . . .. .. . .. .. . ., .. .... ... . , . ~ . . . ... ~
5~7~i5
- 8 - HO~ 81/F 132 85 % dyestuff of the formula O~ N=~ ~ NII-C}I~CH3)2 Cl NHCOC2H5 15 % dyestuf of the formula N~2 C2 4 3 O2N- ~ -.N=N ~ NH2 Cl NHCOC~H5 E X A M P L ~ 6 A dyeing formulation the dyestuff portion of which is composed as follows:
42 % dyestuff of the formula NO2 C2 ~s 3 2 ~ =N ~ NE~C2~I5 8 % dyestuf of the ormula ~2 / 2 4 3 2 ~ -N=N ~ NH2 Br N~ICOCH3 42 ~ dyestuf of the formul.a NO
2 /OC2~I~OCH3 2 ~ - ~=N ~ ~ NHC2H5 Br ~HCOC2H5 ~s~
42 % dyestuff of the formula NO2 C2 ~s 3 2 ~ =N ~ NE~C2~I5 8 % dyestuf of the ormula ~2 / 2 4 3 2 ~ -N=N ~ NH2 Br N~ICOCH3 42 ~ dyestuf of the formul.a NO
2 /OC2~I~OCH3 2 ~ - ~=N ~ ~ NHC2H5 Br ~HCOC2H5 ~s~
- 9 - HOE 81 /F 132 8 % dyestuff of the formula N2- ~PC2 4 3 ~sr N~COC 2H 5 ... ... . . . , . . ... , . . ~, . . . .. . .
Claims (4)
1. Dyeing formulations the dyestuff portion of which is a mixture of dyestuffs of the formula (1) (1) in which X is a chlorlne or bromine atom, R1 is a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, and R2 and R3, independently of each other, represent a methyl or ethyl group.
2. Dyeing formulations containing from 10 to 90 % of the dyestuff of the formula , from 10 to 90% of the dyestuff of the formula , from 0 to 30 % of the dyestuff of the formula and from 0 to 30% of the dyestuff of the formula
3. A process for the manufacture of dyeing formulations as claimed in claim 1, which comprises subjecting several dyestuffs of the formula (1) as claimed in claim 1 to a grinding operation.
4. A method for the dyeing or printing of synthetic fiber materials using a dyeing formulation as claimed in claim 1 or 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3121320.0 | 1981-05-29 | ||
| DE19813121320 DE3121320A1 (en) | 1981-05-29 | 1981-05-29 | NEW COLOR PRESENTATIONS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING AND PRINTING SYNTHETIC FIBER MATERIALS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1185755A true CA1185755A (en) | 1985-04-23 |
Family
ID=6133458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000403951A Expired CA1185755A (en) | 1981-05-29 | 1982-05-28 | Dyeing formulations, process for their manufacture and their use for the dyeing and printing of synthetic fiber materials |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0066235A3 (en) |
| JP (1) | JPS57200459A (en) |
| KR (1) | KR830010150A (en) |
| BR (1) | BR8203167A (en) |
| CA (1) | CA1185755A (en) |
| DE (1) | DE3121320A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133355A1 (en) * | 1981-08-22 | 1983-03-10 | Hoechst Ag, 6000 Frankfurt | NEW NAVY BLUE DISPERSION DYES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING OR PRINTING SYNTHETIC FIBER MATERIALS |
| DE3539771A1 (en) * | 1985-11-09 | 1987-05-14 | Cassella Ag | MIXTURES OF BLUE DISPERSION DYES AND THEIR USE FOR DYING POLYESTER |
| DE3834530A1 (en) * | 1988-10-11 | 1990-04-12 | Cassella Ag | COLOR-RESISTANT MONOAZO DYE, THEIR PRODUCTION AND USE |
| DE3908445A1 (en) * | 1989-03-15 | 1990-09-20 | Cassella Ag | DYE MIXTURE |
| DE4023583A1 (en) * | 1990-07-25 | 1992-02-06 | Heller Geb Gmbh Maschf | POSITIONING DEVICE |
| CN108166282B (en) * | 2017-12-30 | 2020-12-22 | 恒天宝丽丝生物基纤维股份有限公司 | Saponification dyeing method for acetate polyamide fiber composite yarn |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE634032A (en) * | ||||
| CH633307A5 (en) * | 1977-03-16 | 1982-11-30 | Ciba Geigy Ag | AZO DYES. |
| MX148450A (en) * | 1977-04-28 | 1983-04-22 | Ici Ltd | MIXTURE OF TWO OR MORE MONDAZOIC DISPERSION DYES |
| DE2736785C3 (en) * | 1977-08-16 | 1980-06-26 | Hoechst Ag, 6000 Frankfurt | New dispersion azo dyes, processes for their production and their use for dyeing or printing synthetic fiber materials |
| DE2833854C2 (en) * | 1978-08-02 | 1980-09-04 | Hoechst Ag, 6000 Frankfurt | New navy blue disperse dyes, processes for their production and their use for dyeing or printing synthetic fiber materials |
-
1981
- 1981-05-29 DE DE19813121320 patent/DE3121320A1/en not_active Withdrawn
-
1982
- 1982-05-25 EP EP82104547A patent/EP0066235A3/en not_active Withdrawn
- 1982-05-27 KR KR1019820002348A patent/KR830010150A/en unknown
- 1982-05-28 BR BR8203167A patent/BR8203167A/en unknown
- 1982-05-28 JP JP57090045A patent/JPS57200459A/en active Pending
- 1982-05-28 CA CA000403951A patent/CA1185755A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57200459A (en) | 1982-12-08 |
| BR8203167A (en) | 1983-05-17 |
| DE3121320A1 (en) | 1982-12-16 |
| EP0066235A2 (en) | 1982-12-08 |
| KR830010150A (en) | 1983-12-26 |
| EP0066235A3 (en) | 1983-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |