CN105219125B - A kind of preparation method of cold curing non-isocyanate water polyurethane base high molecular dye - Google Patents
A kind of preparation method of cold curing non-isocyanate water polyurethane base high molecular dye Download PDFInfo
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- CN105219125B CN105219125B CN201510702930.6A CN201510702930A CN105219125B CN 105219125 B CN105219125 B CN 105219125B CN 201510702930 A CN201510702930 A CN 201510702930A CN 105219125 B CN105219125 B CN 105219125B
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Abstract
The invention discloses a kind of preparation method of cold curing non-isocyanate water polyurethane base high molecular dye, belong to technical field of textile chemical engineering.The present invention prepares non-isocyanate aqueous polyurethane by cyclic carbonate ester oligomer and hydrophilic polyamines ring-opening reaction；It is again that chromogen introduces polyurethane molecular chain by the dye matrix containing amino, and with silane coupler or titanate coupling agent as end-capping reagent, cold curing non-isocyanate water polyurethane base high molecular dye is obtained.The preparation method journey environmental protection, and common water borne polyurethane-base high molecular dye water resistance, heat endurance and mechanical property are improved, its coating or PRINTED FABRIC washing, dry and wet crock fastness are up to more than 45 grades.
Description
Technical field
The invention belongs to technical field of textile chemical engineering, and in particular to a kind of cold curing non-isocyanate water polyurethane base
The preparation method of high molecular dye.
Background technology
Water polyurethane base high molecular dye is to be introduced in polyurethane backbone or side chain dye molecule by chemically reacting
And the coloured macromolecule polymer for being formed.It is the combination on a molecular scale of polyurethane high molecule material and dye molecule, and
There is the film forming of dyestuff chromaticity and polyurethane, be promising functional high molecule material.Due to dyestuff with chemical bond with
Polyurethane molecular chain is connected, and water polyurethane base high molecular dye has excellent solvent resistance and resistance to migration.Additionally, aqueous
Polyurethane-base high molecular dye molecular dimension is big, and chemical stability is good, is difficult to be less readily available for absorption by the skin, with spies such as safety and low toxicity
Property, bonding of textiles agent, colouring agent, color fixing agent, finishing agent etc. are widely used as, with good development and application values.
But, the introducing of hydrophilic chain extender and linear molecule chain structure make polyurethane water resistance not good, seriously limit
Its range of application.Other common water borne polyurethane-base high molecular dye treatment still needed to after on fabric by high temperature bake with
The purpose of fixation is reached, this not only influences the mechanical property of fabric, wearability etc., and consumption mass energy, does not meet green
Colour circle is protected, the requirement of the theory of energy-saving and emission-reduction.
Conventional urethane is usually to be obtained by two XOR polyisocyanates and dihydroxy or polyol reaction.But
Isocyanates has toxicity very big and sensitive to environmental condition in itself, big with environmental hazard to human body.Non-isocyanate polyurethane
Do not use the polyisocyanates of high toxicity and moisture-sensitive material in preparation process not only, and compensate for passing from molecular structure
Weak bonding structure in system polyurethane, chemical resistance, hydrolytic resistance and permeability resistance are more excellent.With " clean manufacturing work
The promotion of skill ", non-isocyanate polyurethane has broad application prospects, and reduces its production cost, and Simplified flowsheet is extremely urgent.
The content of the invention
It is of the invention with silane coupler or titanate coupling agent as end-capping reagent in order to solve the above problems, using non-isocyanide
Acid esters route, prepares a kind of cold curing watersoluble polyurethane-base high molecular dye, to improve common water borne polyurethane-base macromolecule
Dyestuff water resistance, heat endurance and mechanical property, for fabric coating or stamp, improve textile fastness to wet rubbing.Specifically
Processing step is as follows：
The amount fraction 30- of material is added in the four-hole boiling flask equipped with condenser pipe, agitator, thermometer and dropping funel
50% cyclic carbonate ester, is then added dropwise amount fraction 10-30% polyhydric amine compounds, the 1-2 drop Triethylamine catalysts of material, in 65-
Anti- 5-10h at 80 DEG C, adds the amount fraction 5-15% dyestuff chromogens of material, and the anti-5-10h at 65-80 DEG C, is cooled to 25-
30 DEG C of amount fraction 10-30% coupling agents of addition material, react 5-10h, are eventually adding deionized water, at a high speed emulsification 0.5-1h,
The centrifugation 10-30min under 1000-3000rpm rotating speeds, removes unreacted dyestuff chromogen, prepared solid content about 30- again
50% cold curing non-isocyanate water polyurethane base high molecular dye dispersion liquid；
By 20-40wt% cold curing non-isocyanate polyurethane based high moleculars dye dispersion liquid, 10-30wt% thickeners
PFL, 30-70wt% deionized water are well mixed, and coating or stamp, drying at room temperature 6-24h are carried out to bafta.
The cyclic carbonate ester contains two or polycyclic carbonate oligomers for end group.
The polyhydric amine compounds are ethane diamine double-2-hyolroxy propane sulfonic acid sodium, 2,4- diamino benzene sulfonic acid sodium.
The dyestuff chromogen is the dyestuff chromogen containing diaminourea, for example Isosorbide-5-Nitrae-diamino-anthraquinone, 1,5- diaminoanthraquinone-s
One kind of quinone, 1,8- diamino-anthraquinones.
The coupling agent is silane coupler or titanate coupling agent containing amino or epoxy radicals, such as γ-aminopropyl
Triethoxysilane, γ-glycidyl ether oxygen propyl trimethoxy silicane, 4- aminobenzenes sulphonyl two (12 benzene sulfonyl) metatitanic acid are different
Propyl ester etc..
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
Embodiment one：
The acid of 4mmol binary ring carbon is added in the four-hole boiling flask equipped with condenser pipe, agitator, thermometer and dropping funel
Ester, is then added dropwise anti-10h at 2mmol ethane diamine double-2-hyolroxy propane sulfonic acids sodium, 2 70 DEG C of catalyst of triethylamine of drop, adds
Anti- 5h at 70 DEG C of 1mmol1,4- diamino-anthraquinone material chromogen, adds 2mmol gamma-aminopropyl-triethoxys after being cooled to 30 DEG C
Silane coupler, reacts 5h, is eventually adding a certain amount of deionized water, at a high speed emulsification 0.5h, then the centrifugation point under 3000rpm rotating speeds
From 30min, unreacted dye matrix, the cold curing non-isocyanate polyurethane based high molecular of prepared solid content about 30% are removed
Dye dispersion liquid.
By 20wt% cold curing non-isocyanate polyurethane based high moleculars dye dispersion liquid, 20wt% thickeners PFL,
60wt% deionized waters are well mixed, and stamp, drying at room temperature 12h are carried out to bafta.
Embodiment two：
The acid of 4mmol binary ring carbon is added in the four-hole boiling flask equipped with condenser pipe, agitator, thermometer and dropping funel
Ester, is then added dropwise 1mmol 2, anti-10h at 4- diamino benzene sulfonic acids sodium, 2 70 DEG C of catalyst of triethylamine of drop, adds 2mmol 1,8-
Anti- 5h at 70 DEG C of diamino-anthraquinone material chromogen, adds 2mmol 4- aminobenzenes sulphonyl two (12 benzene sulfonyl) after being cooled to 30 DEG C
Isopropyl titanate, reacts 5h, is eventually adding a certain amount of deionized water, at a high speed emulsification 0.5h, then the centrifugation point under 3000rpm rotating speeds
From 30min, unreacted dye matrix, the cold curing non-isocyanate polyurethane based high molecular of prepared solid content about 50% are removed
Dye dispersion liquid.
By 40wt% cold curing non-isocyanate polyurethane based high moleculars dye dispersion liquid, 10wt% thickeners PFL,
50wt% deionized waters are well mixed, and coating, drying at room temperature 12h are carried out to bafta.
Claims (5)
1. a kind of preparation method of cold curing non-isocyanate water polyurethane base high molecular dye, it is characterized in that using following
Processing step：
(1) the amount fraction 30- of material is added in the four-hole boiling flask equipped with condenser pipe, agitator, thermometer and dropping funel
50% cyclic carbonate ester, is then added dropwise amount fraction 10-30% polyhydric amine compounds, the 1-2 drop Triethylamine catalysts of material, in 65-
5-10h is reacted at 80 DEG C, the amount fraction for adding material is 5-15% diamino radical dye chromogens, and reacts 5- at 65-80 DEG C
10h, is cooled to the 25-30 DEG C of amount fraction 10-30% coupling agent of addition material, reacts 5-10h, is eventually adding deionized water, high
Speed emulsification 0.5-1h, then the centrifugation 10-30min under 1000-3000rpm rotating speeds, remove unreacted dyestuff chromogen, system
Obtain solid content 30-50% cold curing non-isocyanate water polyurethane base high molecular dye dispersion liquids；
(2) by 20-40wt% cold curing non-isocyanate polyurethane based high moleculars dye dispersion liquid, 10-30wt% thickeners
PFL, 30-70wt% deionized water are well mixed, and coating or stamp, drying at room temperature 6-12h are carried out to bafta.
2. a kind of preparation side of cold curing non-isocyanate water polyurethane base high molecular dye as claimed in claim 1
Method, it is characterised in that the cyclic carbonate ester is that end group contains two or polycyclic carbonate oligomers.
3. a kind of preparation side of cold curing non-isocyanate water polyurethane base high molecular dye as claimed in claim 1
Method, it is characterised in that the polyhydric amine compounds are ethane diamine double-2-hyolroxy propane sulfonic acid sodium, 2,4- diamino benzene sulfonic acid sodium.
4. a kind of preparation side of cold curing non-isocyanate water polyurethane base high molecular dye as claimed in claim 1
Method, it is characterised in that the diamino radical dye chromogen is Isosorbide-5-Nitrae-diamino-anthraquinone, 1,5- diamino-anthraquinones, 1,8- diaminoanthraquinone-s
One kind of quinone.
5. a kind of preparation side of cold curing non-isocyanate water polyurethane base high molecular dye as claimed in claim 1
Method, it is characterised in that the coupling agent is silane coupler or titanate coupling agent containing amino or epoxy radicals, wherein containing
The silane coupler of amino or epoxy radicals is gamma-aminopropyl-triethoxy-silane, γ-glycidyl ether oxygen propyl trimethoxy silicon
One kind in alkane；Titanate coupling agent containing amino is 4- aminobenzenes sulphonyl two (12 benzene sulfonyl) isopropyl titanate.
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| WO2018042030A1 (en) * | 2016-09-05 | 2018-03-08 | Merz+Benteli Ag | Use of an organocarbonate-modified prepolymer as reactant for preparation of isocyanate-free and isothiocyanate-free alkoxysilane polymers |
| CN106758421A (en) * | 2017-01-18 | 2017-05-31 | 江南大学 | A kind of method of the imitative tie dyeing style treatment of utilization polyurethane-base high molecular dye |
| CN108531088A (en) * | 2018-04-25 | 2018-09-14 | 姜凤艳 | A kind of water-fast environment-friendly type polyurethane adhesive agent |
| ES2948888T3 (en) * | 2019-02-08 | 2023-09-21 | Basf Se | Preparation of a cured polymer comprising urethane groups and silicon atoms |
| CN110358039B (en) * | 2019-08-28 | 2021-05-04 | 盐城工学院 | Preparation method of self-coloring polyurethane based on zwitterion, product and application thereof |
| CN115260827B (en) * | 2022-04-15 | 2023-05-12 | 中国科学院理化技术研究所 | Colorant suitable for water-based ink, preparation method of colorant and water-based ink containing colorant |
| CN114773828A (en) * | 2022-05-06 | 2022-07-22 | 盛鼎高新材料有限公司 | Corrosion-resistant polyurethane elastomer and preparation method thereof |
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| DE3723782A1 (en) * | 1987-07-16 | 1989-01-26 | Dainippon Ink & Chemicals | METHOD FOR PRODUCING CYCLOCARBONATE COMPOUNDS |
| CN101775137B (en) * | 2010-03-15 | 2012-06-13 | 华中科技大学 | Water-based non-isocyanate polyurethane and preparation method thereof |
| CN102731779B (en) * | 2011-12-29 | 2014-02-26 | 湖北航天化学技术研究所 | Synthetic method of hybrid non-isocyanate polyurethane |
| CN102746714A (en) * | 2012-05-02 | 2012-10-24 | 中国皮革和制鞋工业研究院 | Preparation method for transference resistance leather dye |
| CN104212201B (en) * | 2014-08-06 | 2017-04-05 | 京东方科技集团股份有限公司 | Polymeric dye and preparation method thereof, light resistance composition and display device |
| CN104262570B (en) * | 2014-09-16 | 2016-08-17 | 中国科学技术大学 | A kind of preparation method of black water polyurethane dyestuff |
| CN104311779B (en) * | 2014-10-11 | 2017-06-16 | 江南大学 | A kind of synthetic method of aqueous polyurethane high molecular dye |
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