CN1317337C - Red monoazo-dyes composition - Google Patents

Red monoazo-dyes composition Download PDF

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Publication number
CN1317337C
CN1317337C CNB2004100990968A CN200410099096A CN1317337C CN 1317337 C CN1317337 C CN 1317337C CN B2004100990968 A CNB2004100990968 A CN B2004100990968A CN 200410099096 A CN200410099096 A CN 200410099096A CN 1317337 C CN1317337 C CN 1317337C
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China
Prior art keywords
dye
dyestuff
grades
formula
red
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CNB2004100990968A
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CN1648168A (en
Inventor
阮伟祥
张云保
宋瑜
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Runtu Group Holdings Ltd
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Zhejiang Longsheng Group Co Ltd
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Priority to CNB2004100990968A priority Critical patent/CN1317337C/en
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046Mixtures of two or more azo dyes
    • C09B67/0051Mixtures of two or more azo dyes mixture of two or more monoazo dyes

Abstract

The present invention relates to red mono-azo-dye composition which comprises dye A shown in a formula (I) and dye B shown in a formula (II). The red dye composition of the present invention dyes hydrophobic textile materials; particularly, when ester is gathered and materials are blended, the present invention has the advantage of excellent dye performance, such as good heat resistance migration fastness, fine colour fastness to water, excellent light fastness, and uniform colour tone, and still has fine lifting performance during dipping dye and hot melted dyeing. The dye is also suitable for the discharge printing of polyester materials.

Description

A kind of red monoazo-dyes composition
(1) technical field
The present invention relates to a kind of red monoazo-dyes composition.
(2) background technology
Dispersed dye are usually used in the dyeing of hydrophobic textile materials, particularly polyester textile.But during with present known disperse dyeing or stamp, find to exist following problem: otherwise its heat-resisting transport property, color fastness to water, colour fastness to light can not meet the demands well; Its diffustivity is relatively poor, and enhancing is not ideal enough when dip-dye, pad-dry-cure dyeing.Show that especially printing and dyeing are red under the situation of blue color.For this reason, be necessary to develop a class dyeing behavior excellence, the well behaved dyestuff of lifting or dye composite.
(3) summary of the invention
In order to overcome the deficiency of existing dispersive red dye dyeing behavior, the invention provides a kind of Monoazo-dyes composition.
Described red monoazo-dyes composition comprises suc as formula the dyestuff A shown in (I) with suc as formula the dyestuff B shown in (II);
Figure C20041009909600041
Wherein, X 1For H or-CN, be preferably-CN;
X 2For H ,-CN or-NO 2, be preferably H;
R 1Be H or halogen, be preferably H or Cl;
R 2, R 3Independently be-CH separately 3Or-C 2H 5, be preferably-CH 3
R 4Be C 1~C 4Alkyl, be preferably-CH 3,-C 2H 5
R 5Be H or halogen, be preferably H, Br.
R 6Be CN or halogen, be preferably CN, Br.
R 7, R 8Independent separately is H, C 1~C 4Alkyl ,-C 2H 4OCH 3Or-CH (CH 3) COOCH 3,
Be preferably-C 2H 5,-C 2H 4OCH 3Or-CH (CH 3) COOCH 3
Described dye composite is preferably basically especially by suc as formula dyestuff A shown in (III) and the composition formed suc as formula the dyestuff B shown in (IV).
Figure C20041009909600051
The weight percentage of described dyestuff A can be 1~99%, is preferably 5~95%, more preferably 10~90%; The weight percentage of dyestuff B can be 1~99%, is preferably 5~95%, more preferably 10~90%.
When preparing orchil composition of the present invention, the dyestuff of the dyestuff of employed formula (I) expression and formula (II) expression is respectively disclosed dyestuff such as patent EP555179 and patent WO2004044058 or similar these dyestuff, with the method for wherein record or similarly method can make at an easy rate.
Dispersion red dye composition of the present invention generally needs to add auxiliary agent and disperses during application.For example that structural formula (I) and structural formula (II) is represented former dyestuff carries out corpusculed with pulverizers such as sand mill or shredders after mixing by above-mentioned proportioning in the presence of auxiliary agent, water or other wetting agent; Also structural formula (I) and the represented former dyestuff of structural formula (II) can be carried out mixing with above-mentioned ratio after corpusculed is handled with pulverizers such as sand mill or shredders respectively in the presence of auxiliary agent, water or other wetting agent in addition.Usually, auxiliary agent is 0.8~5: 1 with the ratio of former dyestuff weight.
Described auxiliary agent is dyestuff dispersion agent commonly used, diffusant etc. when composite, comprise one of following or its several mixture arbitrarily: anionic dispersing agents such as the formaldehyde condensation products of the formaldehyde condensation products of naphthene sulfonic acid and alkyl benzene sulphonate (ABS), the formaldehyde condensation products of alkyl naphthalene sulfonic acid, cresol sulfonic acid, sulfonated lignin, the perhaps non-ionic dispersing agents such as ethylene oxide adduct of the ethylene oxide adduct of the segmented copolymer of oxyethane, propylene oxide, alkylphenol, polystyrene phenol.Particularly, naphthalene sulfonic acidformaldehyde condensation product such as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound) etc., sulfonated lignin such as sodium lignosulfonate (as commercial dispersants Reax 83A, Reax 85A) etc.
Orchil composition of the present invention, the liquid state after can corpusculed, emulsifiable paste attitude or with spray-drying process etc. carry out dried powdery, the particulate state state is supplied with dyeing.With the orchil composition of the present invention hydrophobic textile materials of printing and dyeing, particularly when polyester and blended material thereof, has remarkable dyeing behavior, for example heat-resisting migration fastness is good, color fastness to water is good, light fastness is excellent, uniform hue, and when dip-dye, pad-dry-cure dyeing, still have good enhancing.This dyestuff also is applicable to the discharge printing of polyester material.
(4) embodiment
The invention will be further described below in conjunction with embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
Former dyestuff 20 grams shown in former dyestuff shown in the formula (III) 30 grams, the formula (IV), dispersion agent Reax 85A 60 grams, pure water 135 grams one are reinstated sand mill and carried out corpusculed (making dispersion treatment), spraying drying promptly gets orchil composition of the present invention again.
Embodiment 2~10
According to the preparation method of embodiment 1, be by the continuous data shown in the following table 2 component A, B component to be pieced together mixedly as the dye composite that is used, wherein, the defined dye structure formula of each substituting group sees Table 1.
Table 1
The embodiment title Dyestuff A Dyestuff B
X 1 X 2 R 1 R 2=R 3 R 4 R 5 R 6 R 7 R 8
Embodiment 2 -CN H H -CH 3 -C 3H 7 H Br H -CH(CH 3)CO 2CH 3
Embodiment 3 H -NO 2 H -CH 3 -CH 3 H -CN -C 2H 5 -CH(CH 3)CO 2CH 3
Embodiment 4 H -CN H -C 2H 5 -C 2H 5 H Br H -CH(CH 3)CO 2CH 3
Embodiment 5 H -CN H -C 2H 5 -CH 3 H Br -C 2H 4OCH 3 -C 2H 4OCH 3
Embodiment 6 -CN H Cl -CH 3 -CH 3 Br Br -C 2H 4OCH 3 -C 2H 4OCH 3
Embodiment 7 -CN H H -C 2H 5 -C 2H 5 H -CN -C 2H 4OCH 3 -C 2H 4OCH 3
Embodiment 8 -CN H Cl -C 2H 5 -CH 3 Br Br -C 2H 4OCH 3 -C 2H 4OCH 3
Embodiment 9 H -CN H -CH 3 -C 2H 5 H Br H -CH(CH 3)CO 2CH 3
Embodiment H -NO 2 H -C 2H 5 -CH 3 H -CN -C 2H 5 -CH(CH 3)CO 2CH 3
Table 2
The embodiment title Dyestuff A (gram) Dyestuff B (gram) Auxiliary agent (gram) Pure water (gram)
Embodiment 2 49 1 60 Dispersant MF 135
Embodiment 3 45 5 60 135
Embodiment 4 40 10 60 135
Embodiment 5 35 15 60 Dispersing agent CNF 135
Embodiment 6 25 25 60 135
Embodiment 7 20 30 60 135
Embodiment 8 15 35 60 Dispersion agent Reax 83A 135
Embodiment 9 8 42 60 135
Embodiment 10 2 48 60 135
Embodiment 11
Respectively getting 0.5 dye composite that makes of gram embodiment 1~10 is dispersed in 500 ml waters, mix with 60 milliliters water after drawing 20 milliliters, transferring dye bath PH with acetic acid is 4.5~5, be warming up to 70 ℃ put into simultaneously 2 the gram woven dacrons dye, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 40 minutes, be cooled to begin below 90 ℃ the sampling.Adopt that GB GB/T3921-1997, GB/T3920-1997, GB/T8427-1998, GB/T5718-1997 test respectively that it is water-fastly washed, rub resistance, colour fastness to light and sub limation fastness.Test result sees Table 3.
Table 3
The embodiment title Water-fast washing (60 ℃) Rub resistance Fast light Sublimation fastness (180 ℃)
Embodiment 1 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 2 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 3 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 4 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 5 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 6 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 7 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 8 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 9 4~5 grades 4~5 grades 〉=6 grades 4~5 grades
Embodiment 10 4~5 grades 4~5 grades 〉=6 grades 4~5 grades

Claims (10)

1, a kind of red monoazo-dyes composition comprises suc as formula the dyestuff A shown in (I) with suc as formula the dyestuff B shown in (II);
Figure C2004100990960002C1
Wherein, X 1For H or-CN, X 2For H ,-CN or-NO 2
R 1Be H or halogen; R 2, R 3Independently be-CH separately 3Or-C 2H 5
R 4Be C 1~C 4Alkyl; R 5Be H or halogen; R 6Be CN or halogen;
R 7, R 8Independent separately is H, C 1~C 4Alkyl ,-C 2H 4OCH 3Or-CH (CH 3) COOCH 3
2, red monoazo-dyes composition as claimed in claim 1 is characterized in that described X 1For-CN, X 2Be H.
3, red monoazo-dyes composition as claimed in claim 1 is characterized in that described R 1Be H or Cl, R 2, R 3Be respectively-CH 3
4, red monoazo-dyes composition as claimed in claim 2 is characterized in that described R 1Be H, R 2, R 3Be respectively-CH 3
5, red monoazo-dyes composition as claimed in claim 1 is characterized in that described R 4For-CH 3Or-C 2H 5, R 5Be H or Br, R 6For-CN or Br, R 7, R 8Independently be-C separately 2H 5,-C 2H 4OCH 3Or-CH (CH 3) COOCH 3
6, red monoazo-dyes composition as claimed in claim 5 is characterized in that described R 4For-CH 3, R 5Be H, R 6For-CN, R 7For-C 2H 5, R 8For-CH (CH 3) COOCH 3
7, red monoazo-dyes composition as claimed in claim 6 is characterized in that basically by forming suc as formula the dyestuff A shown in (III) with suc as formula the dyestuff B shown in (IV).
8, as the described red monoazo-dyes composition of one of claim 1~7, the weight percentage that it is characterized in that dyestuff A is 1~99%, and the weight percentage of dyestuff B is 1~99%.
9, red monoazo-dyes composition as claimed in claim 8, the weight percentage that it is characterized in that dyestuff A is 5~95%, the weight percentage of dyestuff B is 5~95%.
10, red monoazo-dyes composition as claimed in claim 9, the weight percentage that it is characterized in that dyestuff A is 10~90%, the weight percentage of dyestuff B is 10~90%.
CNB2004100990968A 2004-12-28 2004-12-28 Red monoazo-dyes composition Expired - Fee Related CN1317337C (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0196537A2 (en) * 1985-03-30 1986-10-08 CASSELLA Aktiengesellschaft Water insoluble red monoazo dyes, their preparation and their use
EP0228092A2 (en) * 1985-12-30 1987-07-08 Mitsubishi Kasei Corporation Mixed monoazo dye and method of dyeing polyester fibers using the same
US5608042A (en) * 1994-03-08 1997-03-04 Dystar Japan Ltd. Benzothiazolemonoazo dyes
WO2004044058A1 (en) * 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azo dyes, process for their preparation and their use
WO2005055179A1 (en) * 2003-12-02 2005-06-16 Leif Bertil Hjert Advertisment switcher

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0196537A2 (en) * 1985-03-30 1986-10-08 CASSELLA Aktiengesellschaft Water insoluble red monoazo dyes, their preparation and their use
EP0228092A2 (en) * 1985-12-30 1987-07-08 Mitsubishi Kasei Corporation Mixed monoazo dye and method of dyeing polyester fibers using the same
US5608042A (en) * 1994-03-08 1997-03-04 Dystar Japan Ltd. Benzothiazolemonoazo dyes
WO2004044058A1 (en) * 2002-11-11 2004-05-27 Ciba Specialty Chemicals Holding Inc. Phthalimidyl-azo dyes, process for their preparation and their use
WO2005055179A1 (en) * 2003-12-02 2005-06-16 Leif Bertil Hjert Advertisment switcher

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