CN114933723A - Preparation method of super-tough polyurethane crosslinked network - Google Patents

Preparation method of super-tough polyurethane crosslinked network Download PDF

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CN114933723A
CN114933723A CN202210630998.8A CN202210630998A CN114933723A CN 114933723 A CN114933723 A CN 114933723A CN 202210630998 A CN202210630998 A CN 202210630998A CN 114933723 A CN114933723 A CN 114933723A
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super
polyurethane
tough
cross
self
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高传慧
高义梁
王彦庆
王日璇
刘月涛
徐环斐
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Qingdao University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Abstract

The invention belongs to the field of polymer preparation, and relates to a preparation method of a super-tough polyurethane cross-linked network. The method comprises the following steps: the self-repairing polyurethane micro-crosslinking network based on multiple hydrogen bonds is obtained by using isophorone diisocyanate and polypropylene glycol as raw materials, carrying out chain extension by using adipic acid dihydrazide and carrying out crosslinking by using diazo alkyl. The preparation method of the self-repairing polyurethane cross-linked network is novel, adipic acid dihydrazide provides multiple hydrogen bonds, and diazo alkyl urea is used as a cross-linking agent to prepare the polyurethane elastomer with the amorphous hard domain structure. The prepared elastomer has ultrahigh toughness and high-efficiency self-repairing capability. The cost of the selected raw materials is low, and the method has wide market prospect. Simple steps, convenient operation and strong practicability.

Description

Preparation method of super-tough polyurethane crosslinked network
Technical Field
The invention relates to the field of elastomer self-repair, in particular to a preparation method of a super-tough polyurethane cross-linked network with multiple hydrogen bonds.
Background
The information in this background section is only for enhancement of understanding of the general background of the invention and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art that is already known to a person of ordinary skill in the art.
The self-repairing material is a material capable of self-recovering under the condition of damage, the emergence of the self-repairing material not only increases the durability of the material, but also has great influence on the service life of the material, polyurethane as a novel organic high polymer material is known as 'fifth plastic' which is widely applied to a plurality of fields such as buildings, automobiles and aviation due to the excellent performances such as stability, chemical resistance, rebound resilience, sound insulation, heat insulation, shock resistance and wear resistance, but certain damage can be inevitably caused to the material working in a malignant environment, a reversible bond is a dynamic bond which can be exchanged mutually under certain environmental conditions, the bond can be broken and assembled due to the dynamic characteristics of the bond, the dynamic bond is introduced into a polyurethane elastomer, and the mechanical property of the polyurethane is influenced profoundly, therefore, the self-repairing performance of the polyurethane material is possibly endowed, and the service life of the polyurethane elastomer is greatly prolonged. The polyurethane is a polymer prepared by carrying out end capping and chain extension on isocyanate groups and polyol or polyamine, and the design of a soft domain and a hard domain and a spatial structure in the material is reasonably controlled, so that the material is endowed with more excellent performance and function, and multiple hydrogen bonds are introduced into the polyurethane elastomer material.
For the self-repairing elastomer, the combination of high toughness, quick rebound and high efficiency self-repairing is still a challenge.
Disclosure of Invention
In order to prepare the elastomer with high toughness, quick rebound and high self-repairing efficiency, the invention provides a design and a preparation method of a super-tough polyurethane crosslinking network based on multiple hydrogen bonds, the number of the hydrogen bonds and the spatial structure of a polymer are reasonably regulated so as to simultaneously endow the material with ultrahigh toughness, rebound resilience and self-repairing performance, in order to prepare the self-repairing polyurethane elastomer with high comprehensive performance, polypropylene glycol is specially selected as a soft segment in the test, because the polypropylene glycol is not easy to crystallize and has excellent fluidity, the side chain methyl increases the entanglement between chain segments and is beneficial to energy dissipation, adipic dihydrazide is selected as a chain extender, rich carbonyl structures and formed ureido structures can greatly enhance the dissipation of energy, diazoalkyl urea is finally selected as a crosslinking agent, and the covalent network structure enhances the external force resistance of the elastomer, the carbonyl structure of the side chain can form a hydrogen bond effect, the elastomer is endowed with excellent resilience, free hydroxyl forms weak hydrogen bonds, the self-repairing capability of the elastomer is improved, the number of the hydrogen bonds and the spatial structure of the polymer are controlled by controlling the proportion of adipic acid dihydrazide and diazoalkane, the combined action of the physical bond and the chemical bond and the mutual entanglement of the soft segment endow the material with super-strong toughness, quick resilience and excellent self-repairing performance, and the elastomer with super-strong toughness, quick resilience and high self-repairing efficiency is prepared by reasonably regulating and controlling multiple hydrogen bonds and a network structure.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
in a first aspect of the present invention, a method for preparing a super-tough polyurethane crosslinked network is provided, which comprises:
uniformly mixing isocyanate, polypropylene glycol and a catalyst in a solvent, and reacting to obtain a prepolymer;
carrying out chain extension on the prepolymer and adipic acid dihydrazide to obtain a polymer;
and (3) crosslinking the polymer with diazoalkyl urea to obtain the product.
The polyurethane elastomer with super toughness, quick rebound and high-efficiency self-repairing efficiency is prepared by reasonably adjusting the spatial structure and the number of hydrogen bonds, and is expected to realize industrial production due to cheap and easily available raw materials.
In a second aspect of the invention, there is provided a cross-linked network of a super-tough polyurethane prepared by the above process.
In a third aspect of the invention, the application of the super-tough polyurethane crosslinked network in the fields of building, automobile and aviation is provided.
The invention has the beneficial effects that:
(1) compared with most of self-repairing polyurethane elastomers at present, the self-repairing polyurethane elastomer has excellent mechanical property of 24-40 MPa, and simultaneously has super-strong toughness of 240-630 MJ/m 3 And a self-healing efficiency of up to 102%.
(2) Compared with most of self-repairing polyurethane elastomers at present, the self-repairing polyurethane elastomer has excellent resilience, the material is stretched to 1000% cyclically, and the dissipated energy can be almost completely recovered after 3h of maintenance at 20 ℃.
(3) Compared with most of the current self-repairing polyurethane elastomers, the self-repairing polyurethane elastomer has better thermal stability.
(4) Compared with most of the existing self-repairing polyurethane elastomers, the raw materials involved in the invention are cheaper, and the industrial production is easy to realize.
(5) The preparation method is simple, convenient to operate and high in practicability.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a polymer formula of the present invention.
FIG. 2 is a cyclic stretch diagram of example 4 of the present invention.
FIG. 3 is a thermogram of example 4 of the present invention.
FIG. 4 is a stress-strain diagram before and after self-healing of the material of example 4 of the present invention.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
Interpretation of terms
"DMAC" in this application means: dimethylacetamide;
"PPG" means: a polypropylene glycol;
"IPDI" means: isophorone diisocyanate;
"DBTDL" means: dibutyl tin dilaurate.
A preparation method of a super-tough polyurethane cross-linked network with multiple hydrogen bonds is characterized in that isophorone diisocyanate, polypropylene glycol, adipic acid dihydrazide and diazo alkyl are used as raw materials, and a polyurethane elastomer network is generated through a polymerization reaction under the catalysis condition of a catalyst dibutyltin dilaurate.
A polyurethane network.
A preparation method of a multi-hydrogen bond super-tough polyurethane crosslinking network takes isophorone diisocyanate, polypropylene glycol, adipic acid dihydrazide and diazoalkane as raw materials, and generates the polyurethane network through polymerization reaction in the presence of a catalyst, wherein the molecular formula of the polyurethane network is as follows:
Figure RE-GDA0003757060990000041
the tensile strength of the composite material is 24.8-38.7 MPa; the toughness is 240-625 MJ/m 3 The material can show self-repairing efficiency of 102% at 100 ℃.
The polyether with the side chain methyl is selected as the soft segment, and the material is not easy to crystallize.
The molecular weight of the polyether adopted by the invention is 400-2000 g/mol of polypropylene glycol soft segment.
The isocyanate selected in the present invention is an asymmetric diisocyanate.
The selected diisocyanate is isophorone diisocyanate, and the isocyanate has the characteristics of asymmetric structure and flexible cyclic structure to endow soft segment with better fluidity.
The chain extender selected by the invention is an amine-terminated chain extender.
The chain extender selected by the invention is terminal amino adipic acid dihydrazide, and because the chain extender has rich carbonyl structures, more hydrogen bond sites are formed, and the high toughness of the material is greatly promoted.
The cross-linking agent selected by the invention is a tetrahydroxy monomer with broad-spectrum antibacterial property.
The cross-linking agent selected by the invention is diazo alkyl urea, and provides a covalent cross-linking network and a hydrogen bond site.
The invention also provides a preparation method of the better super-tough polyurethane material, which comprises the following steps:
first, an asymmetric cycloaliphatic isophorone diisocyanate was mixed with a certain molar amount of polypropylene glycol in the presence of a catalyst (dibutyltin dilaurate) in a ratio of 1: 0.4-0.8, reacting to generate a prepolymer, adding adipic dihydrazide (IPDI: adipic dihydrazide is 1: 0.1-0.6, reacting at 30-100 ℃ for 2-15 h to produce a polymer, finally adding diazolyl urea (IPDI: diazolyl urea is 1: 0.1-0.8, reacting at 30-100 ℃ for 1-10 h, and finally placing the synthesized polymer in an oven at 80 ℃ to obtain the elastomer with 24-40 MPa tensile strength, 2100-0% elongation at break and 85% self-repairing efficiency.
Note that: the elastomer is required to be in a nitrogen atmosphere in the whole preparation process, and is mechanically stirred at the speed of 100-400 r/min.
The elastomer prepared by the method has high transparency which is up to 80-90%.
The present invention is described in further detail below with reference to specific examples, which are intended to be illustrative of the invention and not limiting.
In the following examples, the following test methods were employed:
the tensile test is carried out according to the national standard GB/T1024.2-2006 with the test speed of 100mm/min at room temperature.
The cyclic stretching experiment was carried out at room temperature at a speed of 100mm/min, according to the test of GB/T1024.2-2006.
Example 1
PPG (4g), IPDI (1.77g) and DBTDL (0.02g) were charged in a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 And mechanically stirring for 2 hours in the atmosphere to obtain a colorless viscous solution which is a prepolymer. After the prepolymer was obtained, adipic acid dihydrazide (0.34g) was dispersed in DMAC (10ml) solvent, and the adipic acid dihydrazide dispersed in DMAC (10ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 h. Slowly adding diazo alkyl urea (0.3g) dissolved in (5ml) DMAC into a container for further reaction for 5h after the reaction is finished, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a viscous self-repairing polyurethane DMAC solution, pouring a solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has the stress of 24.5MPa and the strain of 2173%.
Example 2
PPG (4g), IPDI (1.77g) and DBTDL (0.02g) were charged in a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 And mechanically stirring for 2 hours in the atmosphere to obtain a colorless viscous solution which is a prepolymer. After the prepolymer was obtained, adipic dihydrazide (0.41g) was dispersed in DMAC (10ml) solvent, and the adipic dihydrazide dispersed in DMAC (10ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 hours. Slowly adding diazoalkyl urea (0.25g) dissolved in DMAC (5ml) into a container after the reaction is finished for further reaction for 5h, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a viscous self-repairing polyurethane DMAC solution, pouring a solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has 28.4MPa and 2845% of strain.
Example 3
PPG (4g), IPDI (1.77g) and DBTDL (0.02g) were charged in a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 In atmosphere, machineryStirring for 2h to obtain a colorless viscous solution as a prepolymer. After the prepolymer was obtained, adipic acid dihydrazide (0.49g) was dispersed in DMAC (10ml) solvent, and the adipic acid dihydrazide dispersed in DMAC (10ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 hours. Slowly adding diazoalkyl urea (0.17g) dissolved in DMAC (5ml) into a container after the reaction is finished, further reacting for 5h, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a viscous self-repairing polyurethane DMAC solution, pouring the solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has 33.8MPa and strain of 3350.
Example 4
PPG (4g), IPDI (1.77g) and DBTDL (0.02g) were charged in a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 And mechanically stirring for 2 hours in the atmosphere to obtain a colorless viscous solution which is a prepolymer. After the prepolymer was obtained, adipic acid dihydrazide (0.56g) was dispersed in DMAC (10ml) solvent, and the adipic acid dihydrazide dispersed in 10ml solvent was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 hours. Slowly adding diazoalkyl urea (0.14g) dissolved in DMAC (5ml) into a container after the reaction is finished, further reacting for 5h, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a viscous self-repairing polyurethane DMAC solution, pouring the solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has 38.8MPa and strain of 3760%. The specific test results are shown in fig. 2, 3, and 4.
Example 5
PPG (4g), IPDI (1.77g) and DBTDL (0.02g) were charged in a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 And mechanically stirring for 2 hours in the atmosphere to obtain a colorless viscous solution which is a prepolymer. After the prepolymer was obtained, adipic acid dihydrazide (0.63g) was dispersed in DMAC (10ml) solvent, and the adipic acid dihydrazide dispersed in DMAC (10ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 hours. Slowly adding diazoalkyl urea (0.08g) dissolved in DMAC (5ml) into a container after the reaction is finished, further reacting for 5h, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a viscous self-repairing polyurethane DMAC solution, pouring the solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has 35.4MPa, strain 3556%.
Comparative example 1
PPG (4g), IPDI (1.77g), DBTDL (0.02g) were charged into a 100ml three-necked flask using DMAC as a solvent at 80 ℃ under N 2 And mechanically stirring for 2 hours in the atmosphere to obtain a colorless viscous solution which is a prepolymer. After the prepolymer was obtained, adipic acid dihydrazide (0.56g) was dispersed in DMAC (25ml) solvent, and the adipic acid dihydrazide dispersed in DMAC (10ml) solvent was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 7 h. Slowly adding pentaerythritol (0.08g) dissolved in DMAC (5ml) into a container after the reaction is finished, further reacting for 5h, placing the container in a three-neck flask for 12h after the reaction is finished to obtain a DMAC solution of viscous self-repairing polyurethane, pouring a solvent into a tetrafluoro mold, and drying at 80 ℃, wherein the high-toughness polyurethane has 21MPa and strain of 2057%.
Detailed data are shown in Table I
Figure RE-GDA0003757060990000081
The polyurethane elastomer prepared by the invention has excellent tensile strength, elongation at break and self-repairing performance, and the price of the required raw materials is low, so that the industrial production is expected to be realized.
It should be noted that the above-mentioned embodiments are only preferred embodiments of the present invention, and the present invention is not limited thereto, and 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 modifications and equivalents can be made in the technical solutions described in the foregoing embodiments, or equivalents thereof. 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 (10)

1. A method for preparing a super-tough polyurethane crosslinked network is characterized by comprising the following steps:
uniformly mixing isocyanate, polypropylene glycol and a catalyst in a solvent, and reacting to obtain a prepolymer;
chain extension is carried out on the prepolymer and adipic dihydrazide to obtain a polymer;
and (3) crosslinking the polymer with diazoalkyl urea to obtain the product.
2. The method for preparing the cross-linked network of the super-tough polyurethane according to claim 1, wherein the molar ratio of the isocyanate, the polypropylene glycol, the adipic dihydrazide and the diazolidinyl urea is 1: 0.4-0.8: 0.1-0.6: 0.1 to 0.8.
3. The process for preparing crosslinked networks of super-tough polyurethanes according to claim 1, wherein the isocyanate is an asymmetric diisocyanate, preferably isophorone diisocyanate.
4. The method of preparing a crosslinked network of a super tough polyurethane according to claim 1 wherein the catalyst is dibutyltin dilaurate;
or, the solvent is dimethylacetamide.
5. The process for preparing a crosslinked network of a supertough polyurethane according to claim 1, wherein the molar ratio of isocyanate to catalyst is 1: 0.4 to 0.8.
6. The method for preparing the cross-linked network of the super-tough polyurethane according to claim 1, wherein the whole preparation process is in an inert atmosphere, preferably, the mechanical stirring is carried out at 100 to 400 r/min.
7. A cross-linked network of super-tough polyurethane prepared by the process of any one of claims 1 to 6.
8. The cross-linked network of super tough polyurethane according to claim 7, wherein the composite has a tensile strength of 24.8 to 38.7 MPa; the toughness is 240-625 MJ/m 3 The material having a temperature of 102% at 100 DEG CSelf-repairing efficiency, and the transparency reaches 80-90%.
9. Use of the crosslinked network of polyurethane according to claim 7 or 8 in the fields of architecture, automotive, aeronautics.
10. The use of claim 9, wherein the cross-linked network of super-tough polyurethane is used to make a corrosion-resistant coating, a wound dressing, an ion battery, or electronic skin.
CN202210630998.8A 2022-06-06 2022-06-06 Preparation method of super-tough polyurethane crosslinked network Pending CN114933723A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116284638A (en) * 2022-11-16 2023-06-23 威海市泓淋电力技术股份有限公司 Preparation method of super-toughness polyurethane crosslinked network

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116284638A (en) * 2022-11-16 2023-06-23 威海市泓淋电力技术股份有限公司 Preparation method of super-toughness polyurethane crosslinked network

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