CN103524385A - Preparation method for modified disperse dye dispersing agent and product - Google Patents

Preparation method for modified disperse dye dispersing agent and product Download PDF

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CN103524385A
CN103524385A CN201310480491.XA CN201310480491A CN103524385A CN 103524385 A CN103524385 A CN 103524385A CN 201310480491 A CN201310480491 A CN 201310480491A CN 103524385 A CN103524385 A CN 103524385A
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diffusant
dispersed dye
preparation
reaction
acid
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CN103524385B (en
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仇文仲
陈昭文
王晓辉
徐薇
杨军浩
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ZHEJIANG QINYAN TECHNOLOGY CO., LTD.
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ZHEJIANG QINYAN CHEMICAL CO Ltd
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Abstract

The invention discloses a preparation method for a modified disperse dye dispersing agent. The preparation method comprises the following steps of heating a naphthalene compound to 130-170 DEG C, adding sulfuric acid to perform sulfonation reaction, cooling to 100-130 DEG C after the sulfonation reaction is finished, adding water, cooling to 80-100 DEG C after the reaction is finished, adding an aldehyde compound to perform primary condensation reaction under a temperature condition until the reaction is finished, adding an isomer mixture of CLT (cross laminated timber) acid, heating to 80-100 DEG C, adding the aldehyde compound again to perform secondary condensation reaction, and obtaining the modified disperse dye dispersing agent after the reaction is finished. The invention also provides a dispersing agent product obtained by the method. Wastewater produced by the CLT acid produced in an organic pigment production process is used as a part of production raw materials for producing the modified disperse dye dispersing agent, so that the production cost of the modified disperse dye dispersing agent is reduced, and the pollution caused by the production of the wastewater through the CLT acid on the environment is alleviated; the modified disperse dye dispersing agent is suitable for industrial production.

Description

A kind of preparation method and product of modification dispersed dye diffusant
Technical field
The invention belongs to field of chemical technology, specifically relate to a kind of preparation method and product of modification dispersed dye diffusant.
Background technology
In the commercialization course of processing of dispersed dye, dispersed dye are ground into tiny particle, are conducive to it in the absorption of polyester fibre surface, are finally diffused in the inside of fiber and go, and complete whole dyeing course.And adding of dispersion agent is to be used to improve the dispersing property of such dyestuff in water, prevent in dyeing course, the phenomenons such as the crystal growth that tiny dye granule occurs in dye bath, gathering, aggegation, thus have influence on the quality of dyeing keratin-fiber.
Naphthalene is that dispersed dye diffusant belongs to naphthalene sulfonic formaldehyde condensation compound, at dispersed dye with being to belong to use to obtain the most general type disperse dye diffusant in diffusant family, naphthalene is that dispersed dye diffusant is produced and generally all be take naphthalene or methylnaphthalene and through sulfonation, hydrolysis, condensation, neutralization, desalination etc., be prepared from as raw material, in order to reduce raw materials cost, very great dispersed dye diffusant production unit all replaces naphthalene or methylnaphthalene to produce with coal tar wash oil or oil washing oil at present.
The chloro-5-phenylmethylamine-4-of CLT acid formal name used at school 2-sulfonic acid, it is a kind of important organic red pigment intermediate, on pigment industry, mainly for the production of c.I. Pigment red 52 and c.I. Pigment red 53, this pigment is widely used in paint, coating, colored ink, rubber and coloring plastic etc.CLT acid is that Year's consumption is crossed one of organic intermediate of ten thousand tons in the world.In pigment dyestuff intermediate CLT acid production process, after the hydrogenation reduction stage completes, can produce nearly 1/4 the various isomer mixtures of CLT acid, this component of mixture is more complicated, if be isolated not in time, will affect the product purity of the chloro-3-phenylmethylamine-4-of certified products 6-sulfonic acid and the coloured light of the pigment dyestuff that is later synthesized.Yet how about the various isomer mixtures of nearly 1/4 the CLT producing after separating acid are used, and make it to become the raw material in industrial production, are puzzlement researchist's difficult problems always.
The document of the report section of having CLT acid producing waste water reuse is less both at home and abroad.Publication number is that to disclose a kind of CLT acid producing waste water be that the synthetic high efficiency water reducing agent of raw material and production technique thereof comprise CLT acid producing waste water, phenol compound and solvent mixture heating for dissolving, adjust pH to the Chinese patent literature of CN102731011A; Add after aldehyde compound and auxiliary agent insulation reaction; Reaction finishes rear cooling.Above-mentioned technique is usingd the waste water of the phenyl ring class isomer mixture that CLT acid produces in producing as the raw materials for production of sulfamate high-effective water-reducing agent, on the one hand regeneration industrial waste, on the other hand, the raw materials cost of sulfamate high-effective water-reducing agent reduces approximately 30%, greatly improves the competitive power of product.
Yet the amount of the CLT acid producing waste water of annual domestic generation is very huge, only above-mentioned a kind of way of recycling is difficult to thoroughly solve the technical problem that CLT acid producing waste water reclaims.So, for reducing environmental stress, reducing enterprise's input cost, the waste water recycling mode of exploitation diversification, has great strategic importance.
Summary of the invention
The invention provides a kind of preparation method of modification dispersed dye diffusant, it is in dispersed dye diffusant production process at naphthalene that the method adopts, add the various isomer mixtures of CLT acid, make it participate in the condensation reaction of aldehyde compound, thereby produce the modification dispersed dye diffusant that price is cheaper, both reduced the production cost of modification dispersed dye diffusants, reduced again the various isomer mixtures possibility of the by product-CLT acid pollution on the environment producing in pigment dyestuff intermediate CLT acid production process, suitability for industrialized production is obtained comprehensively, the development of sustainability.
A preparation method for modification dispersed dye diffusant, comprising:
(1) naphthalene compound is heated to 130-170 ℃, adds sulfuric acid to carry out sulfonation reaction, after sulfonation reaction finishes, be cooled to 100-130 ℃, add water, under this temperature condition, reaction finishes;
(2) material step (1) being obtained is cooled to 80-100 ℃, adds aldehyde cpd, carries out primary condensation reaction under this temperature condition, to reaction end;
(3) to the isomer mixture that adds CLT acid in the reaction system liquid of step (2), be warming up to 80-100 ℃, add aldehyde cpd, carry out consecutive condensation, reaction finishes aftertreatment and obtains modification dispersed dye diffusant.
In step (1), described naphthalene compound comprises one or more in the compounds such as naphthalene, methylnaphthalene, also comprises other industrial chemicals that contain methylnaphthalene, naphthalene such as coal tar wash oil, oil washing oil or waste liquid etc.In described coal tar wash oil, oil washing oil, the total weight percent content of methylnaphthalene and naphthalene is generally 50-90%, and the weight percent content of methylnaphthalene is generally 50-80%.It is 98% the vitriol oil that described sulfuric acid is generally purity.
The sulfonation reaction of naphthalene or methylnaphthalene is an electrophilic substitution reaction, when temperature is lower (35～60 ℃) to obtain product be mainly α-naphthalenesulfonicacid or alpha-methyl-naphthalene sulfonic acid; When temperature is higher, mainly generate beta-naphthalenesulfonic-acid or beta-methylnaphthalene sulfonic acid.And the condensation reaction of naphthene sulfonic acid or methyl naphthalene sulfonic acid and formaldehyde is a cationoid reaction, on naphthalene nucleus, can reduce the reactive behavior of naphthalene nucleus during with electron withdrawing groups such as sulfonic groups, when α-naphthalenesulfonicacid or alpha-methyl-naphthalene sulfonic acid and formaldehyde condensation, steric hindrance is unfavorable for more greatly the carrying out of condensation reaction; Beta-naphthalenesulfonic-acid or beta-methylnaphthalene sulfonic acid is presence bit inhibition effect not, so should control reaction conditions in sulfonation reaction step, reaction is carried out towards the direction that generates beta-naphthalenesulfonic-acid or beta-methylnaphthalene sulfonic acid; Experiment shows that vitriol oil concentration more greatly is more conducive to generate beta-naphthalenesulfonic-acid or beta-methylnaphthalene sulfonic acid, so the concentration of the preferred vitriol oil is more than or equal to 98%; The control of temperature of reaction is also conducive to beta-naphthalenesulfonic-acid in addition or beta-methylnaphthalene sulfonic acid generates, so temperature of reaction is controlled at 130-170 ℃, is preferably 140-160 ℃.In this step, adding the object that water reacts is that the α-naphthalenesulfonicacid of generation or alpha-methyl-naphthalene sulfonic acid are converted into beta-naphthalenesulfonic-acid or beta-methylnaphthalene sulfonic acid, is beneficial to follow-up condensation reaction.
In step (1), the mol ratio of described sulfuric acid, water and naphthalene compound is 1-2:1-2:1.The time of described sulfonation reaction is about 1-6 hour, adds after water, and the time of reaction is about 0.5-4 hour.
In step (2), described aldehyde cpd comprises one or more in the compounds such as formaldehyde, trioxymethylene, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, furfural, more preferably formaldehyde.Described aldehyde cpd and the mol ratio of naphthalene compound are 1.5-5:1.The reaction times of described condensation reaction is generally 3-7 hour.The aldehyde cpd adding in this step is mainly used in carrying out condensation reaction with naphthalene compound.
In step (3), the isomer mixture of CLT acid can be arbitrary isomer of CLT acid or the mixture of isomer.As preferably, the isomer mixture of described CLT acid is at least two kinds in compound shown in formula (1)-(6):
As preferably, the isomer mixture of described CLT acid is the mixture of any ratio of forming of compound shown in formula (1)-(6).In CLT acid producing waste water, mainly contain the compound shown in formula (1)-(6), during actual use, can directly add CLT acid producing waste water, the weight percent content of the compound shown in these waste water Chinese style (1)-(6) is generally 20～40%.In the isomer mixture of described CLT acid, the isomer of CLT acid and the mol ratio of naphthalene compound are 0.1-1:1.The isomer that the aldehyde cpd adding in this step is mainly used in realizing CLT acid participates in condensation reaction, in step (3), described aldehyde cpd comprises one or more in the compounds such as formaldehyde, trioxymethylene, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, furfural, more preferably formaldehyde.The mol ratio 1-1.2:1 of the isomer of described aldehyde cpd and CLT acid.
The condensation reaction time of step (3) is generally 2-5 hour, after having reacted, obtain the intermediates that a kind of solid content is 50-60%, through neutralization, the last handling processes such as desalination, can obtain a kind of solid content is the modification dispersed dye diffusant liquid product of 30-40%, also can spray-driedly obtain a kind of modification dispersed dye diffusant powder-like product.
The present invention also provides a kind of modification dispersed dye diffusant product being prepared by aforesaid method, and the formaldehyde of take is example as raw material, and its structure is shown below:
In above formula, R1 is Cl, and R2 is CH 3, R3 is H or CH 3, n=5-7, m=1-2.
This modification dispersed dye diffusant had both contained naphthene sulfonic acid quasi-molecule structure, contain again aniline sulfonic acid quasi-molecule structure, owing to having introduced aniline sulfonic acid molecular structure, improve the avidity of dispersed dye diffusant and dispersed dye, can improve again the diffusive force of dispersed dye diffusant.
Compared with prior art, beneficial effect of the present invention is embodied in:
(1) present method is a kind of commercial run, and its preparation process operation steps is simple, in same reactor, can complete;
(2) the present invention has utilized the sour various isomer mixtures of the byproduct-CLT producing in the production process of pigment dyestuff intermediate CLT acid as a part of raw materials for production of production modification dispersed dye diffusant, by adding naphthalene compounds, sulfuric acid, aldehyde compound, under certain reaction conditions, react and obtain modification dispersed dye diffusant liquid product or the modification dispersed dye diffusant powder-like product that solid content is 30-40%, both reduced the production cost of modification dispersed dye diffusants, reduced again the various isomer mixtures possibility of the by product-CLT acid pollution on the environment producing in pigment dyestuff intermediate CLT acid production process, suitability for industrialized production is obtained comprehensively, the development of sustainability.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read the content of the present invention's instruction, these equivalent form of values fall within the application's appended claims limited range equally.
Embodiment 1
One, modification dispersed dye diffusant production formula (weight part):
Two, modification dispersed dye diffusant production technique:
In reactor, add 20.0 parts of technical methylnaphthalenes (being selected from methylnaphthalene content >=60% of Zhejiang development of evil in febrile disease limited energy company), be warming up to 140 ℃; Be added dropwise to 20.5 parts of 98% sulfuric acid amount, temperature control to 160 ℃; Dropwise back flow reaction 5 hours; Be cooled to 110 ℃; Add 5.4 parts, water; Back flow reaction 3 hours; Be cooled to 90 ℃; Be added dropwise to 14.5 parts, 37% formaldehyde, temperature control to 90 ℃; Back flow reaction 6 hours; Add 16.5 parts of the CLT acid waste water (being selected from the CLT acid waste water that Zhejiang Qin Yan Chemical Co., Ltd. produces) containing the various isomer of 23%CLT acid, be warming up to 90 ℃; Be added dropwise to 1.5 parts, 37% formaldehyde, temperature control to 90 ℃; Back flow reaction 4 hours; Obtain a kind of solid content and be 55% intermediates.Residual sulfuric acid wherein of neutralization, desalination, obtains a kind of solid content and is 35% modification dispersed dye diffusant liquid product, also can spray-driedly obtain a kind of modification dispersed dye diffusant powder-like product.
Embodiment 2
One, modification dispersed dye diffusant production formula (weight part):
Two, modification dispersed dye diffusant production technique:
In reactor, add 17.0 parts of coal tar wash oils (adopt Hunan steel coal tar wash oil, the content of methylnaphthalene is 50% left and right), be warming up to 150 ℃; Be added dropwise to 18.0 parts of 98% sulfuric acid amount, temperature control to 160 ℃; Dropwise back flow reaction 5 hours; Be cooled to 110 ℃; Add 3.9 parts, water; Back flow reaction 3 hours; Be cooled to 90 ℃; Be added dropwise to 12.3 parts, 37% formaldehyde, temperature control to 90 ℃; Back flow reaction 7 hours; Add containing 27.9 parts of the CLT acid waste water of the various isomer of 23%CLT acid, be warming up to 90 ℃; Be added dropwise to 2.4 parts, 37% formaldehyde, temperature control to 90 ℃; Back flow reaction 4 hours; Obtain a kind of solid content and be 60% intermediates.Neutralization, desalination, obtains a kind of solid content and is 40% modification dispersed dye diffusant liquid product, also can spray-driedly obtain a kind of modification dispersed dye diffusant powder-like product.
The modification dispersed dye diffusant that embodiment 1 and embodiment 2 are prepared carries out performance test, and test result is as shown in table 1:
Table 1
As shown in Table 1, the modification dispersed dye diffusant that the inventive method prepares meets HG/T2499-2006 completely about the performance requriements of dispersion agent.During the actual use of modification dispersed dye diffusant of the present invention, consumption is similar to the usage quantity of existing Dispersant MF, can adjust according to actual needs.

Claims (10)

1. a preparation method for modification dispersed dye diffusant, comprising:
(1) naphthalene compound is heated to 130-170 ℃, adds sulfuric acid to carry out sulfonation reaction, after sulfonation reaction finishes, be cooled to 100-130 ℃, add water, under this temperature condition, reaction finishes;
(2) material step (1) being obtained is cooled to 80-100 ℃, adds aldehyde cpd, carries out primary condensation reaction under this temperature condition, to reaction end;
(3) to the isomer mixture that adds CLT acid in the reaction system liquid of step (2), be warming up to 80-100 ℃, add aldehyde cpd, carry out consecutive condensation, reaction finishes aftertreatment and obtains modification dispersed dye diffusant.
2. the preparation method of modification dispersed dye diffusant according to claim 1, is characterized in that, in step (1), described naphthalene compound is at least one in naphthalene, methylnaphthalene, coal tar wash oil, oil washing oil.
3. the preparation method of modification dispersed dye diffusant according to claim 1, is characterized in that, in step (1), the mol ratio of described sulfuric acid, water and naphthalene compound is 1-2:1-2:1.
4. the preparation method of modification dispersed dye diffusant according to claim 1, it is characterized in that, in step (2) and step (3), described aldehyde cpd comprises one or more in formaldehyde, trioxymethylene, acetaldehyde, propionic aldehyde, butyraldehyde, valeral, furfural; In step (2), described aldehyde cpd and the mol ratio of naphthalene compound are 1.5-5:1.
5. the preparation method of modification dispersed dye diffusant according to claim 4, is characterized in that, in step (2) and step (3), described aldehyde cpd is formaldehyde.
6. the preparation method of modification dispersed dye diffusant according to claim 1, is characterized in that, the isomer mixture of described CLT acid is at least two kinds in compound shown in formula (1)-(6):
7. the preparation method of modification dispersed dye diffusant according to claim 6, it is characterized in that, the isomer mixture of described CLT acid is CLT acid producing waste water, and the weight percent content of the compound shown in these waste water Chinese style (1)-(6) is 20～40%.
8. the preparation method of modification dispersed dye diffusant according to claim 1, is characterized in that, in the isomer mixture of described CLT acid, the isomer of CLT acid and the mol ratio of naphthalene compound are 0.1-1:1.
9. the preparation method of modification dispersed dye diffusant according to claim 1, is characterized in that, in step (3), and the mol ratio 1-1.2:1 of the isomer of described aldehyde cpd and CLT acid.
10. a modification dispersed dye diffusant product, is characterized in that, described modification dispersed dye diffusant product is prepared by the preparation method described in the arbitrary claim of claim 1～9.
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CN104892468A (en) * 2015-05-21 2015-09-09 天津大学 Preparation method of sodium 6-chloro-3-nitromethylbenzoyl-4-sulfonate
CN106590013A (en) * 2016-11-30 2017-04-26 浙江秦燕科技股份有限公司 Acid dye raw powder prepared from CLT acid isomer mixture and product
CN106590012A (en) * 2016-11-30 2017-04-26 浙江秦燕科技股份有限公司 Method of using CLT acid isomer mixture to prepare acid dye powder and production

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Publication number Priority date Publication date Assignee Title
CN104892468A (en) * 2015-05-21 2015-09-09 天津大学 Preparation method of sodium 6-chloro-3-nitromethylbenzoyl-4-sulfonate
CN106590013A (en) * 2016-11-30 2017-04-26 浙江秦燕科技股份有限公司 Acid dye raw powder prepared from CLT acid isomer mixture and product
CN106590012A (en) * 2016-11-30 2017-04-26 浙江秦燕科技股份有限公司 Method of using CLT acid isomer mixture to prepare acid dye powder and production
CN106590013B (en) * 2016-11-30 2019-03-05 浙江秦燕科技股份有限公司 The isomer mixture of CLT acid prepares acid dyes original powder and product
CN106590012B (en) * 2016-11-30 2019-03-12 浙江秦燕科技股份有限公司 The isomer mixture of CLT acid prepares the method and product of acid dyes original powder

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