CN112646391A - Dye dispersant and preparation method thereof - Google Patents
Dye dispersant and preparation method thereof Download PDFInfo
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- CN112646391A CN112646391A CN202011531525.XA CN202011531525A CN112646391A CN 112646391 A CN112646391 A CN 112646391A CN 202011531525 A CN202011531525 A CN 202011531525A CN 112646391 A CN112646391 A CN 112646391A
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- polyurethane dispersion
- acrylate
- dye
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- modified polyurethane
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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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
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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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
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- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The invention belongs to the technical field of dispersant preparation, and particularly relates to a dye dispersant and a preparation method thereof, wherein the dye dispersant comprises the following components in percentage by mass: 2-4, wherein the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate. The dye dispersing agent prepared by the invention greatly increases the fluidity and stability of the dye when dispersing the dye, has good water resistance, low temperature resistance dispersibility and heat resistance stability, has wide compatibility, good dispersibility for various dyes, good dyeing property of the dye, simple process and easy obtainment of products.
Description
Technical Field
The invention relates to the technical field of dispersant preparation, in particular to a dye dispersant and a preparation method thereof.
Background
In recent years, in the world textile market, a plurality of green fibers (such as Tene 1 fibers, polylactic acid fibers and polytrimethylene terephthalate fibers) with special properties and high added value are developed to adapt to new textile fibers, the development of new dyes is a necessary trend, and corresponding dye dispersants are required to be developed synchronously.
The Dispersant (Dispersant) is an aid which can improve and improve the dispersibility of solid or liquid materials. It is a kind of processing aid with large amount, wide range and fast development. It has both lipophilic and hydrophilic groups, and therefore, commonly used dispersants are all surfactants.
The dispersants are mainly of the following three main classes: naphthalene sulfonate formaldehyde condensate dye dispersants, lignosulfonate dispersants and polymer dispersants. The naphthalene sulfonate formaldehyde condensate dye dispersant is used for post-processing of disperse dyes to keep insoluble dyes as a water-dye disperse system, so that the aim of dyeing the disperse dyes is fulfilled. However, when the existing naphthalene sulfonate formaldehyde condensate dye dispersant is applied to disperse dyes, the prepared dyes have poor fluidity and stability and poor water resistance, the expected effects on the aspects of low-temperature resistance dispersibility and heat resistance stability are difficult to achieve, and the comprehensive performance cannot meet the requirements of the disperse dyes.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a dye dispersant and a preparation method thereof, and solves the problems that when the existing naphthalene sulfonate formaldehyde condensate dye dispersant is applied to disperse dyes, the prepared dyes have poor fluidity and stability, poor water resistance, difficult achievement of expected effects in low temperature resistance dispersibility and heat resistance stability, and insufficient comprehensive performance of the dyes can meet the requirements of the disperse dyes.
(II) technical scheme
In order to achieve the purpose, the invention provides the following technical scheme: a dye dispersant comprises 6-8 mass percent of: 2-4, wherein the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
As a preferable technical scheme of the invention, the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
As a preferable technical scheme of the invention, the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organosilicon modified acrylate by using a self-emulsification method.
The invention also provides a preparation method of the dye dispersant, which comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 20-30 min, heating to 85-100 ℃, slowly dropwise adding 0.1-0.5% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and S4, compounding 60-80 parts of the acrylate modified polyurethane dispersion obtained in the S2 step with 20-40 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the S3 step to obtain the dye dispersant.
In a preferred embodiment of the present invention, in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
In a preferred embodiment of the present invention, in the step S2, the initiator is azobisisobutyronitrile.
In the step S3, sulfuric acid is added dropwise to industrial naphthalene for sulfonation reaction at 165 ± 3 ℃ for 2-3 hours.
In a preferred embodiment of the present invention, in the step S3, the PH neutralization reaction is performed by adjusting the PH of the condensation material to 7 to 9 under a stirring condition.
(III) advantageous effects
Compared with the prior art, the invention provides a dye dispersant and a preparation method thereof, and the dye dispersant has the following beneficial effects:
the prepared dye dispersing agent greatly increases the fluidity and stability of the dye when dispersing the dye, has good water resistance, low temperature resistance dispersibility and heat resistance stability, has wide compatibility, good dispersibility for various dyes, good dyeing property of the dye, simple process and easy obtainment of products.
Drawings
FIG. 1 is a schematic diagram of the steps of a method for preparing a dye dispersant according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Referring to fig. 1, the present invention provides the following technical solutions: a dye dispersant comprising, by mass, 7: 3, the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, wherein the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
Specifically, the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
Specifically, the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organosilicon modified acrylate through a self-emulsification method.
The invention also provides a preparation method of the dye dispersant, which comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 25min, heating to 95 ℃, slowly dripping 0.3% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and step S4, compounding 70 parts of the acrylate modified polyurethane dispersion obtained in the step S2 with 30 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the step S3 to obtain the dye dispersant.
Specifically, in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
Specifically, in the step S2, the initiator is azobisisobutyronitrile.
Specifically, in the step S3, sulfuric acid is dropwise added into industrial naphthalene for sulfonation reaction, the reaction temperature is 165 ℃, and the reaction time is 2.5 hours.
Specifically, in the step S3, the PH neutralization reaction is performed by adjusting the PH of the condensation product to 8 under stirring.
Example 2
Referring to fig. 1, the present invention provides the following technical solutions: a dye dispersant comprising, by mass, 6:4, the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, wherein the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
Specifically, the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
Specifically, the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organosilicon modified acrylate through a self-emulsification method.
The invention also provides a preparation method of the dye dispersant, which comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 20min, heating to 85 ℃, slowly dripping 0.1% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and S4, compounding 60 parts of the acrylate modified polyurethane dispersion obtained in the S2 step with 40 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the S3 step to obtain the dye dispersant.
Specifically, in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
Specifically, in the step S2, the initiator is azobisisobutyronitrile.
Specifically, in the step S3, the sulfonation is carried out by dropping sulfuric acid into industrial naphthalene, the reaction temperature is 167 ℃, and the reaction time is 2 hours.
Specifically, in the step S3, the PH neutralization reaction is performed by adjusting the PH of the condensation product to 7 with stirring.
Example 3
Referring to fig. 1, the present invention provides the following technical solutions: a dye dispersant comprising, by mass, 8: 2, the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, wherein the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
Specifically, the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
Specifically, the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organosilicon modified acrylate through a self-emulsification method.
The invention also provides a preparation method of the dye dispersant, which comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 30min, heating to 100 ℃, slowly dripping 0.5% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and S4, compounding 80 parts of the acrylate modified polyurethane dispersion obtained in the S2 step with 20 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the S3 step to obtain the dye dispersant.
Specifically, in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
Specifically, in the step S2, the initiator is azobisisobutyronitrile.
Specifically, in the step S3, the sulfonation is carried out by adding sulfuric acid dropwise to industrial naphthalene, wherein the reaction temperature is 162 ℃ and the reaction time is 3 hours.
Specifically, in the step S3, the PH neutralization reaction is performed by adjusting the PH of the condensation product to 9 with stirring.
Example 4
Referring to fig. 1, the present invention provides the following technical solutions: a dye dispersant comprising, by mass, 7.5: 2.5, the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, wherein the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
Specifically, the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
Specifically, the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organosilicon modified acrylate through a self-emulsification method.
The invention also provides a preparation method of the dye dispersant, which comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 28min, heating to 90 ℃, slowly dripping 0.4% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and S4, compounding 75 parts of the acrylate modified polyurethane dispersion obtained in the S2 step with 25 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the S3 step to obtain the dye dispersant.
Specifically, in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
Specifically, in the step S2, the initiator is azobisisobutyronitrile.
Specifically, in the step S3, the sulfonation reaction is to drop sulfuric acid into the industrial naphthalene, the reaction temperature is 166 ℃, and the reaction time is 3 hours.
Specifically, in the step S3, the PH neutralization reaction is performed by adjusting the PH of the condensation product to 9 with stirring.
Comparative example 1
The comparative example is a comparative example of example 1, and the main differences between the comparative example and example 1 are as follows: a dye dispersant comprising, by mass, 6: 5, the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, wherein the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
Comparative example 2
The comparative examples are methyl zeityl sulfonic acid formaldehyde condensate (dispersant MF) or benzyl zeityl sulfonic acid formaldehyde condensate (dispersant CNF) in the prior art.
According to the industrial standard HG/T2499-2006, the dye dispersants prepared in the embodiments 1-4 and the comparative example 1 and the dispersant MF and the dispersant CNF provided by the proportion 2 are subjected to performance tests, and the test results show that the dye dispersant prepared by the invention has better dye fluidity and stability, good water resistance, low temperature resistance dispersibility and heat resistance stability and various performances meeting the requirements of disperse dyes compared with the prior art (the dispersant MF and the dispersant CNF provided by the comparative example 1 and the prior art).
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A dye dispersant, characterized by: the method comprises the following steps of (by mass ratio) 6-8: 2-4, wherein the dye dispersant is obtained by compounding the acrylate modified polyurethane dispersion and a naphthalene dispersant, the acrylate modified polyurethane dispersion is a water-dispersed acrylate modified polyurethane dispersion generated by reacting modified acrylate with a polyurethane dispersion with an active functional group, and the naphthalene dispersant is a naphthalene sulfonic acid formaldehyde condensate.
2. A dye dispersant according to claim 1, characterized in that: the mass ratio of polyurethane to acrylate in the acrylate modified polyurethane dispersion is 6: 4.
3. A dye dispersant according to claim 1, characterized in that: the modification method of the acrylate modified polyurethane dispersion is to modify the polyurethane dispersion by using organic silicon modified acrylate through a self-emulsifying method.
4. A method for preparing a dye dispersant according to any one of claims 1 to 3, characterized in that: the method comprises the following steps:
step S1, synthesizing an organic silicon prepolymer by using a vinyl organic silicon monomer and a cyclic organic silicon monomer under the base catalysis, and copolymerizing the organic silicon prepolymer and acrylate to obtain a silicone-acrylate emulsion;
step S2, adding the polyurethane prepolymer into the silicone-acrylic emulsion obtained in the step S1, ultrasonically dispersing for 20-30 min, heating to 85-100 ℃, slowly dropwise adding 0.1-0.5% of initiator, and standing to obtain the acrylate modified polyurethane dispersion;
s3, synthesizing a naphthalenesulfonic acid-formaldehyde condensate by using industrial naphthalene as a raw material and sequentially performing sulfonation, hydrolysis, condensation and PH neutralization;
and S4, compounding 60-80 parts of the acrylate modified polyurethane dispersion obtained in the S2 step with 20-40 parts of the naphthalenesulfonic acid-formaldehyde condensate obtained in the S3 step to obtain the dye dispersant.
5. The method for preparing a dye dispersant according to claim 4, characterized in that: in the step S1, the mass ratio of the vinyl silicone monomer to the cyclic silicone monomer is 5: 5.
6. The method for preparing a dye dispersant according to claim 4, characterized in that: in the step S2, the initiator is azobisisobutyronitrile.
7. The method for preparing a dye dispersant according to claim 4, characterized in that: in the step S3, sulfuric acid is dropwise added into industrial naphthalene in the sulfonation reaction, the reaction temperature is 165 +/-3 ℃, and the reaction time is 2-3 hours.
8. The method for preparing a dye dispersant according to claim 4, characterized in that: in the step S3, PH neutralization reaction is to adjust the PH of the condensation material to 7-9 under the stirring condition.
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Citations (5)
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| CN102464784A (en) * | 2010-11-19 | 2012-05-23 | 北京佳盛世纪科技有限公司 | Synthesis method of organic silicon modified acrylate copolymer |
| CN102559031A (en) * | 2011-12-30 | 2012-07-11 | 江苏创基新材料有限公司 | Organosilicon-modified aqueous polyurethane-acrylate composite coating agent and preparation method thereof |
| CN106349432A (en) * | 2016-09-05 | 2017-01-25 | 华南理工大学 | Polyurethane modified silicone-acrylic emulsion and preparation method and application thereof |
| CN109593467A (en) * | 2017-09-30 | 2019-04-09 | 陶富名 | A kind of preparation method of modified organic silicone resin |
| CN110862699A (en) * | 2019-11-29 | 2020-03-06 | 海宁绿宇纺织科技有限公司 | Anhydrous dyeing disperse dye color paste, preparation method and application |
-
2020
- 2020-12-22 CN CN202011531525.XA patent/CN112646391A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464784A (en) * | 2010-11-19 | 2012-05-23 | 北京佳盛世纪科技有限公司 | Synthesis method of organic silicon modified acrylate copolymer |
| CN102559031A (en) * | 2011-12-30 | 2012-07-11 | 江苏创基新材料有限公司 | Organosilicon-modified aqueous polyurethane-acrylate composite coating agent and preparation method thereof |
| CN106349432A (en) * | 2016-09-05 | 2017-01-25 | 华南理工大学 | Polyurethane modified silicone-acrylic emulsion and preparation method and application thereof |
| CN109593467A (en) * | 2017-09-30 | 2019-04-09 | 陶富名 | A kind of preparation method of modified organic silicone resin |
| CN110862699A (en) * | 2019-11-29 | 2020-03-06 | 海宁绿宇纺织科技有限公司 | Anhydrous dyeing disperse dye color paste, preparation method and application |
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Application publication date: 20210413 |