CN105504869A - Yellow reactive dye - Google Patents

Yellow reactive dye Download PDF

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Publication number
CN105504869A
CN105504869A CN201510892249.2A CN201510892249A CN105504869A CN 105504869 A CN105504869 A CN 105504869A CN 201510892249 A CN201510892249 A CN 201510892249A CN 105504869 A CN105504869 A CN 105504869A
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CN
China
Prior art keywords
add
ester
methyl
formamido
hydroxy
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Pending
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CN201510892249.2A
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Chinese (zh)
Inventor
张兴华
曹世川
马志坚
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Tianjin Dek Chemical Co Ltd
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Tianjin Dek Chemical Co Ltd
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Priority to CN201510892249.2A priority Critical patent/CN105504869A/en
Publication of CN105504869A publication Critical patent/CN105504869A/en
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    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes
    • C09B62/51—Monoazo dyes

Abstract

The invention relates to a yellow reactive dye. The reactive dye comprises has a general structural formula represented as a formula (I). The yellow reactive dye can be used for dyeing fabric such as cotton, wool, nylon and the like, the dye has the best dyeing effect when applied to cotton fibers, the color is bright, the color fixation is good, and better fastness property is achieved; good repeatability and stability are realized in the dyeing process, the preparation process is simple, and the operation is convenient.

Description

A kind of Yellow active dye
Technical field
The present invention relates to active dye technical field, particularly relate to a kind of Yellow active dye and preparation method thereof.
Background technology
Reactive dyestuffs, also known as chemically-reactive dyes, for when dyeing and the dye of fiber react with.In this kind of dye molecule containing can with the group of fiber generation chemical reaction, during dyeing, dyestuff and fiber-reactive, form covalent linkage therebetween, becomes overall, and washable and fastness to rubbing is improved.
Reactive dyestuffs because chromatogram is complete, bright in colour, excellent performance, suitability strong, and become the primary dye of cellulose dyeing.It is the Dyestuffs Used for Cellulose Fibres that a kind of cost performance is the highest, this is not only because it is one of optimal selection replacing prohibitive dye and other types Dyestuffs Used for Cellulose Fibres, and it can obtain high-caliber every fastness particularly wet fastness with economic dyeing and simple dying operation.
But along with the continuous renewal of dye techniques, high colour-fast rate, high-performance, oligosaprobic environmental protection type dye have become following main development direction.The object of this invention is to provide a kind of Yellow active dye, can be used for the dyeing of the fabrics such as cotton, hair, nylon, the Color being applied to cotton fibre is best, not only bright in colour, fixation is good, and has good performance fastness.Dyeing course has good circulation ratio and stability, and preparation process is simple, convenient operation.
Summary of the invention
The object of the invention is preparation Yellow active dye, these reactive dyestuffs have such as formula (I) general structure:
In formula
Work as R 1for-SO 2c 2h 4oSO 3m, R 2for-H or-CL;
Work as R 1for-H or-CH 3; R 2for-SO 2c 2h 4oSO 3m;
M is-H or basic metal, and preferably, described M is-H or-Na or-K.
The preferred dye structure of institute is as shown in (II):
Present invention also offers the preparation method of formula II reactive dyestuffs, comprise the steps:
A () 4-beta-hydroxyethyl sulfonyl sulfuric ester-2-anisidine (hereinafter referred to as O-methoxy para-ester) is pulled an oar: be added to the water by O-methoxy para-ester, and making beating makes material particles even, for subsequent use;
(b) O-methoxy para-ester diazotization; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff as shown in structure (II).
The preferred dye structure of institute is as shown in (III):
Present invention also offers the preparation method of above-mentioned reactive dyestuffs, comprise the steps:
A () 5-beta-hydroxyethyl sulfonyl sulfuric ester-2-anisidine (hereinafter referred to as position ester between O-methoxy) pulls an oar: be added to the water by position ester between O-methoxy, and making beating makes material particles even, for subsequent use;
Ester diazotization in position between (b) O-methoxy; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff as shown in structure (III).
The preferred dye structure of institute is as shown in (IV):
Present invention also offers the preparation method of above-mentioned reactive dyestuffs, comprise the steps:
A () 5-methyl-4-beta-hydroxyethyl sulfonyl sulfuric ester-2-anisidine (hereinafter referred to as a gram Li Xiding para-ester) is pulled an oar: be added to the water by a gram Li Xiding para-ester, and making beating makes material particles even, for subsequent use;
(b) gram Li Xiding para-ester diazotization; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff as shown in structure (IV).
In the present invention, the structural formula of described 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone is:
The beneficial effect that the present invention has:
Yellow active dye of the present invention, can be used for the dyeing of the fabrics such as cotton, hair, nylon, the Color being applied to cotton fibre is best, not only bright in colour, fixation is good, and has good performance fastness.Dyeing course has good circulation ratio and stability, and preparation process is simple, convenient operation.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, but do not limit protection scope of the present invention.
Embodiment 1
A kind of Yellow active dye, has the compound of formula II structure:
The preparation method of this Yellow active dye, comprises the steps:
A () O-methoxy para-ester is pulled an oar: add in 200ml water by 100% O-methoxy para-ester 31.1g, and making beating makes material particles even, for subsequent use;
(b) O-methoxy para-ester diazotization; Trash ice 200ml is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add 30% hydrochloric acid 29.81g, the sodium nitrite solution 35.86g adding 20% fast carries out diazotization reaction, keeps the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add the 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder 19.6g of 100% in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then adjust reaction solution pH=6.0 ~ 7.0, through saltouing, filtering, pull an oar, spraying dry gets product dyestuff.I.e. obtained finished product dyestuff as shown in structure (II).
The performance of Yellow active dye prepared by the embodiment of the present invention 1 is as follows:
Light fastness Metal to-metal contact Wet friction To soap colourity Acid sweat stain colourity Alkali sweat stain colourity
4 grades 4-5 level 4-5 level 4-5 level 5 grades 4 grades
Cellulose acetate fibre staining Cotton staining Polymeric amide staining Polyester staining Acrylic fibers staining Wool staining
Soap 4 grades 4-5 level 4-5 level 4 grades 4-5 level 4 grades
Acid sweat stain 4 grades 4-5 level 4-5 level 4-5 level 4-5 level 4 grades
Alkali sweat stain 4 grades 4-5 level 4-5 level 4 grades 4 grades 4-5 level
Embodiment 2
A kind of Yellow active dye, has the compound of formula III structure:
The preparation method of this Yellow active dye, comprises the steps:
Ester making beating in position between (a) O-methoxy: position ester 31.1g between 100% O-methoxy is added in 200ml water, making beating makes material particles even, for subsequent use;
Ester diazotization in position between (b) O-methoxy; Trash ice 200ml is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add 30% hydrochloric acid 29.81g, the sodium nitrite solution 35.86g adding 20% fast carries out diazotization reaction, keeps the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add the 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder 19.6g of 100% in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then adjust reaction solution pH=6.0 ~ 7.0, through saltouing, filtering, pull an oar, spraying dry gets product dyestuff.I.e. obtained finished product dyestuff as shown in structure (III).
The performance of Yellow active dye prepared by the embodiment of the present invention 2 is as follows:
Light fastness Metal to-metal contact Wet friction To soap colourity Acid sweat stain colourity Alkali sweat stain colourity
4 grades 4-5 level 4-5 level 4-5 level 5 grades 4 grades
Cellulose acetate fibre staining Cotton staining Polymeric amide staining Polyester staining Acrylic fibers staining Wool staining
Soap 4 grades 4-5 level 4-5 level 4 grades 4-5 level 4 grades
Acid sweat stain 4 grades 4-5 level 4-5 level 4-5 level 4-5 level 4 grades
Alkali sweat stain 4 grades 4-5 level 4-5 level 4 grades 4 grades 4-5 level
Embodiment 3
A kind of Yellow active dye, has the compound of formula IV structure:
The preparation method of this Yellow active dye, comprises the steps:
(a) gram Li Xiding para-ester making beating: add in 200ml water by 100% gram of Li Xiding para-ester 32.5g, making beating makes material particles even, for subsequent use;
(b) gram Li Xiding para-ester diazotization; Trash ice 200ml is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add 30% hydrochloric acid 29.81g, add the sodium nitrite solution 35.86g that speed adds 20% fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add the 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder 19.6g of 100% in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then adjust reaction solution pH=6.0 ~ 7.0, through saltouing, filtering, pull an oar, spraying dry gets product dyestuff.I.e. obtained finished product dyestuff as shown in structure (IV).
The performance of Yellow active dye prepared by the embodiment of the present invention 3 is as follows:
Light fastness Metal to-metal contact Wet friction To soap colourity Acid sweat stain colourity Alkali sweat stain colourity
4 grades 4-5 level 4-5 level 4-5 level 5 grades 4 grades
Cellulose acetate fibre staining Cotton staining Polymeric amide staining Polyester staining Acrylic fibers staining Wool staining
Soap 4 grades 4-5 level 4-5 level 4 grades 4-5 level 4 grades
Acid sweat stain 4 grades 4-5 level 4-5 level 4-5 level 4-5 level 4 grades
Alkali sweat stain 4 grades 4-5 level 4-5 level 4 grades 4 grades 4-5 level

Claims (4)

1. a Yellow active dye, is characterized in that: these reactive dyestuffs have such as formula (I) general structure:
In formula
Work as R 1for-SO 2c 2h 4oSO 3m, R 2for-H or-CL;
Work as R 1for-H or-CH 3; R 2for-SO 2c 2h 4oSO 3m;
M is-H or basic metal, and preferably, described M is-H or-Na or-K.
2. a preparation method for Yellow active dye, is characterized in that: comprise the steps:
A () O-methoxy para-ester is pulled an oar: be added to the water by O-methoxy para-ester, and making beating makes material particles even, for subsequent use;
(b) O-methoxy para-ester diazotization; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff shown in structure (II):
3. a preparation method for Yellow active dye, is characterized in that: comprise the steps:
Ester making beating in position between (a) O-methoxy: position ester between O-methoxy is added to the water, making beating makes material particles even, for subsequent use;
Ester diazotization in position between (b) O-methoxy; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff as shown in structure (III);
4. a preparation method for Yellow active dye, is characterized in that: comprise the steps:
A () 5-methyl-4-beta-hydroxyethyl sulfonyl sulfuric ester-2-anisidine (hereinafter referred to as a gram Li Xiding para-ester) is pulled an oar: be added to the water by a gram Li Xiding para-ester, and making beating makes material particles even, for subsequent use;
(b) gram Li Xiding para-ester diazotization; Trash ice is added to step (a), outside ice bath simultaneously, under being cooled to 0 ~ 8 DEG C of condition, add hydrochloric acid, add the sodium nitrite solution dissolved in advance fast and carry out diazotization reaction, keep the micro-indigo plant of starch potassium iodide paper, stirring reaction 1 ~ 3 hour, add thionamic acid after having reacted and eliminate unreacted nitrous acid, then regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c) coupling: add 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone powder in the diazonium salt obtained by step (b), stirring reaction 5 ~ 10 hours under DEG C condition of control T=5 ~ 20, it is terminal by coupling completely that tlc analyzes 3-formamido--4-methyl-5-sulfonic acid methylene radical-6-hydroxy-n-ethylpyridine ketone, then reaction solution pH=6.0 ~ 7.0 are adjusted, i.e. obtained finished product dyestuff as shown in structure (IV);
CN201510892249.2A 2015-11-27 2015-11-27 Yellow reactive dye Pending CN105504869A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106118121A (en) * 2016-06-21 2016-11-16 沈阳化工大学 N substituted pyridinone yl pyridines class quaternary ammonium salt monoazo dyes preparation method
CN106349744A (en) * 2016-08-24 2017-01-25 天津德凯化工股份有限公司 Yellow active dye with high brightness and preparation method of yellow active dye

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994906A (en) * 1970-12-22 1976-11-30 Ciba-Geigy Ag 3-Sulphoalkyl-6-hydroxy-pyrid-(2)-ones
US5359041A (en) * 1991-07-11 1994-10-25 Bayer Aktiengesellschaft Pyridone dyestuffs
US5530104A (en) * 1992-03-05 1996-06-25 Ciba-Geigy Corporation Fiber reactive disazo dyes having a 2-vinylsulfonyl-5-sulfoaniline diazo component or a precursor thereof
CN101705014A (en) * 2009-11-16 2010-05-12 天津德凯化工股份有限公司 Orange reactive dye for wool and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3994906A (en) * 1970-12-22 1976-11-30 Ciba-Geigy Ag 3-Sulphoalkyl-6-hydroxy-pyrid-(2)-ones
US5359041A (en) * 1991-07-11 1994-10-25 Bayer Aktiengesellschaft Pyridone dyestuffs
US5530104A (en) * 1992-03-05 1996-06-25 Ciba-Geigy Corporation Fiber reactive disazo dyes having a 2-vinylsulfonyl-5-sulfoaniline diazo component or a precursor thereof
CN101705014A (en) * 2009-11-16 2010-05-12 天津德凯化工股份有限公司 Orange reactive dye for wool and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106118121A (en) * 2016-06-21 2016-11-16 沈阳化工大学 N substituted pyridinone yl pyridines class quaternary ammonium salt monoazo dyes preparation method
CN106349744A (en) * 2016-08-24 2017-01-25 天津德凯化工股份有限公司 Yellow active dye with high brightness and preparation method of yellow active dye

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