CN104774317A - Preparation method and product of side long chain alkyl polyurethane chain extender - Google Patents
Preparation method and product of side long chain alkyl polyurethane chain extender Download PDFInfo
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- CN104774317A CN104774317A CN201510162219.6A CN201510162219A CN104774317A CN 104774317 A CN104774317 A CN 104774317A CN 201510162219 A CN201510162219 A CN 201510162219A CN 104774317 A CN104774317 A CN 104774317A
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Abstract
The invention relates to a preparation method and product of a side long chain alkyl polyurethane chain extender. The preparation method comprises the following steps: preparing raw materials including diisocyanate, higher aliphatic alcohol, polyhydroxy compounds, a catalyst and an organic solvent; performing dehydration pretreatment on the polyhydroxy compounds; alkylating diisocyanate; and alkylating the polyhydroxy compounds to prepare the side long chain alkyl polyurethane chain extender. The preparation method disclosed by the invention is strong in controllability and simple in equipment; the side long chain alkyl polyurethane chain extender prepared by using the method disclosed by the invention can be used for preparing various polyurethane materials so as to ensure that relatively high content of side long chain alkyl groups can be introduced into polyurethane macromolecules, significant water-repellent and anti-fouling properties can be brought to the polyurethane materials, and good market prospects can be achieved; and the product is safe and environment-friendly, and is convenient to use.
Description
Technical field
The present invention relates to the preparation for various polyurethane high molecule material, to introduce the chainextender of side chain alkyl in polyurethane high molecule, be specifically related to preparation method of a kind of side chain alkyl polyurethane chain extender and products thereof.
Background technology
Polyurethane high molecule material is often used to the coating of all kinds of base material and covers with paint, lacquer, colour wash, etc. processing.For solving the problem of conventional urethane finishing agent low temperature fatiguability and elasticity, extensibility, functional difference, the polyurethane finishing agent through various functional monomer modification becomes the main product covering with paint, lacquer, colour wash, etc. manufacture field just day by day.Various functional monomer or reactive functional molecular are generally introduced polyurethane skeleton and are obtained by chemical reactions such as block copolymerization, grafting and end-blockings by functional urethane finishing agent.But existing various functional monomer mostly is monofuntional molecule structure, be difficult to be facilitated and access among polyurethane high molecule in large quantities, therefore modified effect is undesirable.Meanwhile, current functional monomer lacks waterproofing function, is difficult to obtain waterproof and the polyurethane material of hydrolysis.
At present, the functional urethane chainextender prepared for functional urethane comprises following several:
1, the preparation method of fluorine-containing diamine chainextender and high-strength, high-elastic, high temperature resistant urethane, its raw material comprises vulcabond, polyether glycol, functional chainextender, thinner.
As Kong Fanjia, Yang Xiaohui, the people such as Yao Hongxi show the preparation method that " Synthesis and characterization that fluorine-containing diamine is the polyurethane elastomer of chainextender " (" polyurethane industrial " 23 volumes the 1st phase in 2008) discloses fluorine-containing diamine chainextender and fluorochemical urethane, in its raw material: vulcabond is tolylene diisocyanate, polyether glycol to be molecular weight be 1000 polytetrahydrofuran diol, functional chainextender is for raw material homemade 2 with perfluor dihydroxyphenyl propane, two [4-(4-amino-benzene oxygen) phenyl] HFC-236fa of 2-, thinner is N, dinethylformamide.
The fluorine-containing diamine chainextender that the method obtains can introduce fluorine-containing side chain to polyurethane high molecule effectively, the fluorochemical urethane prepared for chainextender with it is due to firmly intersegmental strong hydrogen bonding effect and dipole effect, moiety segments arrangement in microcell is made to form microlitic structure in order, therefore have heat-resisting and oxidation resistent susceptibility preferably, the tensile strength of material and breaking elongation are also better.But the preparation process of fluorine-containing diamine chainextender is very complicated, and productive rate is lower, cost is higher, in addition, the winter hardiness of the fluorochemical urethane prepared for chainextender with it is also poor.
2, siliceous mixed chain extender and low-modulus polyurethane method for producing elastomers, its raw material comprises vulcabond, hydrocarbon hydroxyl polysiloxane, functional chainextender, catalyzer, thinner.
As Wang Yunfang, Guo Zengchang, king you quick show " organosilicon/chain expansion of succinic acid agent ratio of mixture is to the performance impact of the large glycol-based polyurethane elastomer of mixing " (" Chinese tackiness agent " 17 volumes the 5th phase in 2008) disclosed siliceous mixed chain extender and low-modulus polyurethane method for producing elastomers, in its raw material: vulcabond is 4, 4-diphenylmethanediisocyanate, the α of hydrocarbon hydroxyl polysiloxane to be homemade hydroxyl value be 12.07mgKOH/g, ω-bis-(γ-hydroxypropyl) polydimethylsiloxane and hydroxyl value are the polyoxy tetramethylene of 160mgKOH/g, functional chainextender is 1, two (the 4-hydroxyl butyl)-1 of 3-, 1, 3, 3-tetramethyl disiloxane and 1, the mixture of 4-butyleneglycol, catalyzer is stannous octoate, thinner is the mixture of dimethyl formamide and tetrahydrofuran (THF).
The siliceous mixed chain extender that the method is prepared obviously can improve the flexibility of polyurethane elastomer, but little on the ultimate tensile strength impact of material.Except this, thermotolerance is poor.Meanwhile, there is not clear and definite crosslinking structure in polyurethane high molecule material prepared by the method, the microphase separation degree of this macromolecular material is higher in addition, and therefore water tolerance is poor.
3, containing the mixed chain extender of uracil ketone side base and the preparation method of flexible urethane elastomer, its raw material comprises vulcabond, polyether glycol, functional chainextender, catalyzer, thinner.
As Feng Zhicheng, Zhu Bo, the people such as Shi Jinjun to show " synthesis of Quadrupolar hydrogen bond chainextender and the impact on urethane performance thereof " (" polyurethane industrial " 26 volumes the 2nd phase in 2011) disclosed containing the mixed chain extender of uracil ketone side base and the preparation method of flexible urethane elastomer, in its raw material: vulcabond is hexamethylene diisocyanate, polyether glycol to be molecular weight be 1400 polytetrahydrofuran diol, functional chainextender is homemade 2-methyl-2-2-two urea 4 [1H]-pyrimidine ketone group-l, ammediol and 1, the mixture of 4-butyleneglycol, catalyzer is dibutyl tin dilaurate, thinner is dimethyl formamide.
What the method was prepared obviously can improve the flexibility of polyurethane elastomer, breaking elongation and tensile strength containing the mixed chain extender of uracil ketone side base, and high molecular main chain not easily thermo-cracking.But the initial decomposition temperature of the polyurethane elastomer prepared with this mixed chain extender is lower.Meanwhile, the preparation process containing the chainextender of uracil ketone side base is very complicated, and productive rate is lower, cost is higher, and the winter hardiness of the polyurethane elastomer prepared for chainextender with it is also poor.
Summary of the invention
Technical problem to be solved by this invention is: provide preparation method of a kind of side chain alkyl polyurethane chain extender and products thereof.This chainextender can be used for the side chain alkyl introducing high level in polyurethane high molecule, gives the performance that polyurethane material significantly refuses the antifouling and low temperature softness of water, has good market outlook.
The present invention for solving the problems of the technologies described above adopted technical scheme is:
The preparation method of side chain alkyl polyurethane chain extender, is characterized in that: comprise the following steps:
(1) raw material prepares: vulcabond, high fatty alcohol, polyol, catalyzer, organic solvent, by molar fraction, and vulcabond 1, high fatty alcohol 1, polyol 1;
(2) polyol dewaters pretreated step, and polyol is carried out dehydration pre-treatment by this step under vacuum, heating condition, obtained anhydrous polyol;
(3) the alkylating step of vulcabond, vulcabond, high fatty alcohol react by this step under the catalysis of catalyzer, obtained alkylation vulcabond;
(4) the alkylating step of polyol, alkylation vulcabond and anhydrous polyol react by this step in presence of organic solvent, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
By such scheme, the temperature of step (2) vacuum hydro-extraction is 90 ~ 100 DEG C, vacuum tightness-0.100 ~-0.098MPa, dewatering time 40 ~ 80min.
By such scheme, step (3) temperature of reaction is 70 ~ 90 DEG C, reaction times 80 ~ 120min.
By such scheme, step (4) temperature of reaction is 50 ~ 70 DEG C, reaction 70 ~ 100min.
By such scheme, described vulcabond is the one in tolylene diisocyanate, isophorone diisocyanate, 1,6-di-isocyanate.
By such scheme, described high fatty alcohol is carbon length is 8 ~ 12 (C
8~ C
12) saturated monohydroxy alcohol in one.
By such scheme, polyol to be molecular weight be 90 ~ 150 trivalent alcohol or ternary hydramine in one.
By such scheme, described catalyzer is stannous octoate or dibutyl tin laurate, and the quality of catalyzer is 0.02 ~ 0.05% of vulcabond, high fatty alcohol and polyol three gross weight.
By such scheme, the organic solvent of described step (4) is the one in acetone, methylethylketone, vinyl acetic monomer, N-BUTYL ACETATE, and the consumption of organic solvent normally carries out for making reaction process.
By such scheme, the preparation method of above-mentioned side chain alkyl polyurethane chain extender specifically comprises the following steps:
(1) raw material is prepared according to the requirement in such scheme;
(2) polyol is dropped into dewatering unit; Be heated to 90 ~ 100 DEG C, under the vacuum tightness of-0.100 ~-0.098MPa, process 40 ~ 80min; Be cooled to less than 50 DEG C, remove vacuum, sealing is preserved, obtained anhydrous polyol;
(3) vulcabond is dropped into reaction unit, be warming up to 50 ~ 70 DEG C, in 30 ~ 60min, drip high fatty alcohol and control temperature is 50 ~ 70 DEG C, then catalyzer is added, controlling temperature of reaction is 70 ~ 90 DEG C, reaction 80 ~ 120min, obtained alkylation vulcabond;
(4) above-mentioned reaction system is cooled to 50 ~ 70 DEG C; In reaction system, drop into anhydrous polyol, maintaining and stirring also control temperature is 50 ~ 70 DEG C, reaction 70 ~ 100min, period adds organic solvent several times in right amount, to control the viscosity of reaction system, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
According to the side chain alkyl polyurethane chain extender product that the preparation method of above-mentioned side chain alkyl polyurethane chain extender obtains.
Compared with prior art, the inventive method has the following advantages and feature:
1, the present invention utilizes the highly selective and high reactivity of reacting between isocyanate groups and hydroxyl, is connected by high fatty alcohol by vulcabond with multifunctional hydroxy compounds, obtains the polyurethane chain extender containing side chain alkyl.Preparation method is by force handling, and technological process is simple, with short production cycle, and to production unit without particular requirement, desired raw material is easy to get.
2, the present invention is by the design of reactant ratio, feeding sequence and control, effectively control the structure of product, product structure is clear and definite, by product is few, productive rate is high, the side chain alkyl polyurethane chain extender of preparation is water white transparency thick liquid, safety and environmental protection, easy to use.
3, the side chain alkyl polyurethane chain extender that prepared by the present invention can facilitate and in various negatively charged ion, positively charged ion and non-ionic polyurethane macromolecular scaffold, introduce chain alkyl side chain in large quantities, and reaction process steadily, is easily controlled; For polyurethane high molecule material prepared by chainextender, there is low temperature softness, deep drawing quality with it and refuse the good characteristics such as water is antifouling significantly.
Embodiment
The preparation method of embodiment 1 side of the present invention chain alkyl polyurethane chain extender
The raw material of this preparation method comprises:
Vulcabond: tolylene diisocyanate 1mol (174.2g)
High fatty alcohol: n-Octanol 1mol (130.2g)
Polyol: glycerol 1mol (92.1g)
Catalyzer: stannous octoate 0.12g
Organic solvent: acetone 40g
The concrete steps of this preparation method:
(1) polyol dewaters pretreated step, and polyol is carried out dehydration pre-treatment by this step under vacuum, heating condition, obtained anhydrous polyol; Be specially:
(1.1) polyol is dropped into dewatering unit;
(1.2) be heated to 95 ~ 100 DEG C, under the vacuum tightness of-0.099MPa, process 60min;
(1.3) be cooled to less than 50 DEG C, remove vacuum, sealing is preserved, obtained anhydrous polyol.
(2) the alkylating step of vulcabond, vulcabond, high fatty alcohol react by this step under the catalysis of catalyzer, obtained alkylation vulcabond; Be specially:
(2.1) vulcabond is dropped into reaction unit,
Be warming up to 55 ~ 60 DEG C, in 40min, drip high fatty alcohol and control temperature is 55 ~ 60 DEG C;
(2.2) in the reaction system of step (2.1), add catalyzer, controlling temperature of reaction is 75 ~ 80 DEG C, reaction 100min, obtained alkylation vulcabond.
(3) the alkylating step of polyol, alkylation vulcabond and anhydrous polyol react by this step, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.Be specially:
(3.1) reaction system of step (2.2) is cooled to 50 ~ 55 DEG C;
(3.2) in the reaction system of (3.1), anhydrous polyol is dropped into, maintaining and stirring also control temperature is 55 ~ 60 DEG C, reaction 80min, period adds organic solvent several times in right amount, to control the viscosity of reaction system, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
End-use usage prepared by the inventive method: side chain alkyl polyurethane chain extender prepared by the inventive method is water white transparency thick liquid, can be used for the side chain alkyl introducing high level in various polyurethane high molecule, and it is compared with current various conventional non-ionic polyurethane chainextender, that significantly can improve polyurethane material refuses that water is antifouling, low temperature is soft and the performance of anti-complications, gives polyurethane material and significantly refuses that water is antifouling, low temperature is soft and the performance of anti-complications.
Product stock prepared by the inventive method: finished product must be preserved in the sealing of shady and cool, dry place.
The preparation method of embodiment 2 side of the present invention chain alkyl polyurethane chain extender
The raw material of this preparation method comprises:
Vulcabond: isoflurane chalcone diisocyanate 1mol (222.3g)
High fatty alcohol: nonylcarbinol 1mol (158.3g)
Polyol: trihydroxybutane 1mol (106.1g)
Catalyzer: dibutyl tin laurate 0.20g
Organic solvent: methylethylketone 50g
The concrete steps of this preparation method:
(1) polyol dewaters pretreated step, and polyol is carried out dehydration pre-treatment by this step under vacuum, heating condition, obtained anhydrous polyol; Be specially:
(1.1) polyol is dropped into dewatering unit;
(1.2) be heated to 100 DEG C, under the vacuum tightness of-0.098MPa, process 80min;
(1.3) be cooled to less than 50 DEG C, remove vacuum, sealing is preserved, obtained anhydrous polyol.
(2) the alkylating step of vulcabond, vulcabond, high fatty alcohol react by this step under the catalytic condition of catalyzer, obtained alkylation vulcabond; Be specially:
(2.1) vulcabond is dropped into reaction unit,
Be warming up to 60 ~ 65 DEG C, in 30min, drip high fatty alcohol and control temperature is 60 ~ 65 DEG C;
(2.2) in the reaction system of step (2.1), add catalyzer, controlling temperature of reaction is 80 ± 2 DEG C, reaction 110min, obtained alkylation vulcabond.
(3) the alkylating step of polyol, alkylation vulcabond and anhydrous polyol react by this step, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.Be specially:
(3.1) reaction system of step (2.2) is cooled to 55 ~ 60 DEG C;
(3.2) in the reaction system of (3.1), anhydrous polyol is dropped into, maintaining and stirring also control temperature is 65 ~ 70 DEG C, reaction 90min, period adds organic solvent several times in right amount, to control the viscosity of reaction system, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
End-use usage prepared by the inventive method: side chain alkyl polyurethane chain extender prepared by the inventive method is water white transparency thick liquid, can be used for the side chain alkyl introducing high level in various polyurethane high molecule.It is compared with current various conventional non-ionic polyurethane chainextender, and that significantly can improve polyurethane material refuses that water is antifouling, low temperature is soft and the performance of anti-complications, gives polyurethane material and significantly refuses that water is antifouling, low temperature is soft and the performance of anti-complications.
Product stock prepared by the inventive method: finished product must be preserved in the sealing of shady and cool, dry place.
The preparation method of embodiment 3 side of the present invention chain alkyl polyurethane chain extender
The raw material of this preparation method comprises:
Vulcabond: hexamethylene diisocyanate 1mol (168.0g)
High fatty alcohol: lauryl alcohol 1mol (186.3g)
Polyol: trolamine 1mol (149.2g)
Catalyzer: stannous octoate 0.19g
Organic solvent: N-BUTYL ACETATE 60g
The concrete steps of this preparation method:
(1) polyol dewaters pretreated step, and polyol is carried out dehydration pre-treatment by this step under vacuum, heating condition, obtained anhydrous polyol; Be specially:
(1.1) polyol is dropped into dewatering unit;
(1.2) be heated to 100 DEG C, under the vacuum tightness of-0.099MPa, process 70min;
(1.3) be cooled to less than 50 DEG C, remove vacuum, sealing is preserved, obtained anhydrous polyol.
(2) the alkylating step of vulcabond, vulcabond, high fatty alcohol react by this step under the catalysis of catalyzer, obtained alkylation vulcabond; Be specially:
(2.1) vulcabond is dropped into reaction unit,
Be warming up to 65 ~ 70 DEG C, in 40min, drip high fatty alcohol and control temperature is 65 ~ 70 DEG C;
(2.2) in the reaction system of step (2.1), add catalyzer, controlling temperature of reaction is 85 ± 2 DEG C, reaction 120min, obtained alkylation vulcabond.
(3) the alkylating step of polyol, alkylation vulcabond and anhydrous polyol react by this step, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.Be specially:
(3.1) reaction system of step (2.2) is cooled to 50 ~ 55 DEG C;
(3.2) in the reaction system of (3.1), anhydrous polyol is dropped into, maintaining and stirring also control temperature is 50 ~ 55 DEG C, reaction 70min, period adds organic solvent several times in right amount, to control the viscosity of reaction system, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
End-use usage prepared by the inventive method: side chain alkyl polyurethane chain extender prepared by the inventive method is water white transparency thick liquid, can be used for the side chain alkyl introducing high level in various polyurethane high molecule.It is compared with current various conventional non-ionic polyurethane chainextender, and that significantly can improve polyurethane material refuses that water is antifouling, low temperature is soft and the performance of anti-complications, gives polyurethane material and significantly refuses that water is antifouling, low temperature is soft and the performance of anti-complications.
Product stock prepared by the inventive method: finished product must be preserved in the sealing of shady and cool, dry place.
The foregoing is only preferred embodiments of the present invention, in fact each concrete raw material cited by the present invention, and the bound of each raw material, interval value, and the bound of processing parameter (as temperature, time etc.), interval value can realize the present invention, do not enumerate embodiment at this.
Therefore, above embodiment is not in order to limit the present invention, and the usual change that those skilled in the art carries out within the scope of technical solution of the present invention and replacement all should be included in protection scope of the present invention.
Claims (10)
1. the preparation method of side chain alkyl polyurethane chain extender, is characterized in that: comprise the following steps:
(1) raw material prepares: vulcabond, high fatty alcohol, polyol, catalyzer, organic solvent, by molar fraction, and vulcabond 1, high fatty alcohol 1, polyol 1;
(2) polyol dewaters pretreated step, and polyol is carried out dehydration pre-treatment by this step under vacuum, heating condition, obtained anhydrous polyol;
(3) the alkylating step of vulcabond, vulcabond, high fatty alcohol react by this step under the catalysis of catalyzer, obtained alkylation vulcabond;
(4) the alkylating step of polyol, alkylation vulcabond and anhydrous polyol react by this step in presence of organic solvent, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
2. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: the temperature of step (2) vacuum hydro-extraction is 90 ~ 100 DEG C, vacuum tightness-0.100 ~-0.098MPa, dewatering time 40 ~ 80min.
3. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: step (3) temperature of reaction is 70 ~ 90 DEG C, reaction times 80 ~ 120min.
4. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: step (4) temperature of reaction is 50 ~ 70 DEG C, reaction 70 ~ 100min.
5. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: described vulcabond is the one in tolylene diisocyanate, isophorone diisocyanate, 1,6-di-isocyanate.
6. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: the described high fatty alcohol one that to be carbon length be in the saturated monohydroxy alcohol of 8 ~ 12.
7. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: polyol to be molecular weight be 90 ~ 150 trivalent alcohol or ternary hydramine in one.
8. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, it is characterized in that: described catalyzer is stannous octoate or dibutyl tin laurate, the quality of catalyzer is 0.02 ~ 0.05% of vulcabond, high fatty alcohol and polyol three gross weight;
The organic solvent of described step (4) is the one in acetone, methylethylketone, vinyl acetic monomer, N-BUTYL ACETATE, and the consumption of organic solvent normally carries out for making reaction process.
9. the preparation method of side according to claim 1 chain alkyl polyurethane chain extender, is characterized in that: it specifically comprises the following steps:
(1) raw material is prepared according to claim 1;
(2) polyol is dropped into dewatering unit; Be heated to 90 ~ 100 DEG C, under the vacuum tightness of-0.100 ~-0.098MPa, process 40 ~ 80min; Be cooled to less than 50 DEG C, remove vacuum, sealing is preserved, obtained anhydrous polyol;
(3) vulcabond is dropped into reaction unit, be warming up to 40 ~ 50 DEG C, continue to be warming up to 50 ~ 70 DEG C, high fatty alcohol is dripped and control temperature is 50 ~ 70 DEG C in 30 ~ 60min, then catalyzer is added, controlling temperature of reaction is 70 ~ 90 DEG C, reaction 80 ~ 120min, obtained alkylation vulcabond;
(4) above-mentioned reaction system is cooled to 50 ~ 70 DEG C; In reaction system, drop into anhydrous polyol, maintaining and stirring also control temperature is 50 ~ 70 DEG C, reaction 70 ~ 100min, period adds organic solvent several times in right amount, to control the viscosity of reaction system, obtained alkylation polyol, i.e. side chain alkyl polyurethane chain extender.
10. the side chain alkyl polyurethane chain extender product that the preparation method of the side chain alkyl polyurethane chain extender according to any one of claim 1-9 obtains.
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| CN108047419A (en) * | 2017-12-15 | 2018-05-18 | 淄博鲁瑞精细化工有限公司 | The preparation method of the polyurethane-modified silicone softening agent of fluff type |
| CN114621416A (en) * | 2020-12-09 | 2022-06-14 | 万华化学集团股份有限公司 | Aqueous polyurethane dispersion, preparation method and application thereof in two-component spray glue |
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| CN1687172A (en) * | 2005-04-06 | 2005-10-26 | 华南理工大学 | Method for preparing aqueous dispersoid of comb type polyurethane |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105045249A (en) * | 2015-09-10 | 2015-11-11 | 蓝星（北京）技术中心有限公司 | Automatic control method and device for realizing safe production load adjustment in chemical industry production |
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| CN108047419A (en) * | 2017-12-15 | 2018-05-18 | 淄博鲁瑞精细化工有限公司 | The preparation method of the polyurethane-modified silicone softening agent of fluff type |
| CN108047419B (en) * | 2017-12-15 | 2020-05-22 | 淄博鲁瑞精细化工有限公司 | Preparation method of fluffy polyurethane modified organic silicon softening agent |
| CN114621416A (en) * | 2020-12-09 | 2022-06-14 | 万华化学集团股份有限公司 | Aqueous polyurethane dispersion, preparation method and application thereof in two-component spray glue |
| CN114621416B (en) * | 2020-12-09 | 2023-08-11 | 万华化学集团股份有限公司 | Aqueous polyurethane dispersion, preparation method and application thereof in double-component spray adhesive |
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