CN116284638A - Preparation method of super-toughness polyurethane crosslinked network - Google Patents
Preparation method of super-toughness polyurethane crosslinked network Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229920002635 polyurethane Polymers 0.000 title claims description 19
- 239000004814 polyurethane Substances 0.000 title claims description 19
- 229920003225 polyurethane elastomer Polymers 0.000 claims abstract description 27
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- 239000004417 polycarbonate Substances 0.000 claims abstract description 19
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- MERLDGDYUMSLAY-UHFFFAOYSA-N 4-[(4-aminophenyl)disulfanyl]aniline Chemical compound C1=CC(N)=CC=C1SSC1=CC=C(N)C=C1 MERLDGDYUMSLAY-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000463 material Substances 0.000 claims description 25
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- -1 carbonate diol Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
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- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 14
- 229940113088 dimethylacetamide Drugs 0.000 description 11
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6651—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention relates to a preparation method of a super-toughness polyurethane elastomer, and belongs to the field of polymer preparation. The method comprises the following steps: 4,4 '-dicyclohexylmethane diisocyanate and polycarbonate diol (2000 g/mol and 500 g/mol) and 4,4' -diaminodiphenyl disulfide are used for obtaining the super-toughness-based self-repairing polyurethane elastomer. The preparation method of the self-repairing polyurethane elastomer is novel, and the 4,4' -diaminodiphenyl disulfide provides dynamic disulfide bonds, so that the elastomer can realize rapid dynamic exchange under mild conditions. The prepared elastomer has ultrahigh toughness and quick and efficient self-repairing capability. The invention has moderate cost of the selected raw materials and wide market prospect. Simple steps, convenient operation and strong practicability.
Description
Technical Field
The invention relates to the field of self-repairing of elastomers, in particular to a preparation method for preparing an ultra-tough rapid self-repairing polyurethane elastomer by using a polycarbonate self-assembly strategy.
Background
The disclosure of this background section is only intended to increase the 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 already known to those of ordinary skill in the art.
Polyurethane is widely used as a polymer material in a plurality of fields such as construction, automobile and aviation, and the like, because of being simple and easy to regulate and control, and having excellent stability, chemical resistance, rebound resilience, sound insulation, heat insulation, shock resistance, wear resistance and other excellent performances. However, damage is difficult to avoid in daily or engineering use, which not only brings great potential safety hazard to material application, but also most of damaged materials are treated in a direct discarding way, which is not beneficial to recycling of energy sources, and brings great potential hazard to environment. The self-repairing material is a material capable of self-repairing through external stimulus under the condition of damage, and the appearance 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. The self-repairing performance is combined into the polyurethane material, so that the durability of the polyurethane material is improved, and certain potential safety hazards are effectively avoided. The reversible bond is a dynamic bond which can be mutually exchanged under certain environmental conditions, and the dynamic bond is introduced into the polyurethane elastomer, so that the mechanical property of the polyurethane is deeply influenced, the self-repairing property of the polyurethane material is possibly endowed, and the service life of the polyurethane elastomer is greatly prolonged.
For self-repairing elastomer, the polyurethane elastomer has high toughness, quick rebound, high efficiency and quick self-repairing, polycarbonate is used as a soft domain in the research, and the polyurethane elastomer with super toughness, quick rebound and high self-repairing efficiency is prepared by a simple design strategy, so that the polyurethane elastomer is expected to realize industrial production due to proper raw material price.
Disclosure of Invention
In order to prepare the high-toughness, quick rebound, high-efficiency and quick self-repairing elastomer, the invention provides a design synthesis and preparation method based on a non-covalent cross-linked network of polycarbonate, and the ultrahigh toughness, rebound resilience and quick self-repairing performance of a material are endowed through the transformation from static amorphous to dynamic orientation structure. Meanwhile, 4-diaminodiphenyl disulfide is selected as a chain extender, and ureido bonds formed by an amino structure can form strong hydrogen bond interaction, so that the dissipation capacity of the material to external energy is greatly improved, and the dynamic exchange effect of disulfide bonds enables the molecular network of the material to be rearranged rapidly, and the material is convenient to self-repair rapidly. By means of the symmetrical structure of the 4, 4-dicyclohexylmethane diisocyanate, the material is favorable to excellent mechanical performance and has important influence on rebound resilience. The invention prepares the super-strong toughness, quick rebound, high-efficiency and quick self-repairing elastomer by reasonably designing the polymer.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a preparation method of super-toughness and rapid self-healing polyurethane elastomer takes 4,4 '-dicyclohexylmethane diisocyanate, polycarbonate (2000 g/mol and 500 g/mol) and 4,4' -diaminodiphenyl sulfide as raw materials, and the super-toughness polyurethane elastomer is generated in the presence of a catalyst, and the molecular formula of the super-toughness polyurethane elastomer is as follows:
the composite of the inventionThe tensile strength of the material is 32-50MPa; toughness is 420-740 MJ/m 3 The material can show a self-repairing efficiency of 95% when repaired for 100min at 60 ℃.
The invention selects a crystalline soft segment polycarbonate.
The molecular weight of the polycarbonate used in the invention is 500-2000 g/mol.
The isocyanate selected by the invention is isocyanate with symmetrical structure.
The diisocyanate selected by the invention is 4,4' -dicyclohexylmethane diisocyanate, and the isocyanate is characterized by having a symmetrical structure, and the symmetrical structure of the isocyanate endows the material with stronger mechanical properties.
The chain extender selected by the invention is an amine-terminated chain extender.
The chain extender selected by the invention is amino-terminated 4,4' -diaminodiphenyl sulfide, and the monomer contains more benzene ring structures, so that the micro-separation structure is more favorable, the mechanical property of the material is enhanced, urea groups formed by amino groups can form more hydrogen bond sites, and the dissipation capacity and rebound resilience of the material are enhanced.
The invention also provides a preparation method of the excellent super-toughness polyurethane material, which comprises the following steps:
first, a symmetrical 4,4' -dicyclohexylmethane diisocyanate and a molar amount of polycarbonate diol (2000 g/mol and 500 g/mol) were reacted in a one-pot process in dimethylacetamide solvent in the presence of a catalyst (dibutyltin dilaurate) according to 1:0.5 to 0.7: 0.5-0.7, then adding 4,4' -diaminodiphenyl sulfide (4, 4' -dicyclohexylmethane diisocyanate: 4,4' -diaminodiphenyl sulfide=3.2-4:1.2-2.2), reacting for 4-17 hours at 30-90 ℃ to obtain a polyurethane elastomer, and finally placing the synthesized polymer in an oven at 80 ℃ to obtain the elastomer with the tensile strength of 32-50MPa, the elongation at break of 2100-5000% and the self-repairing efficiency of 95%.
Notice that: the elastomer needs to be in nitrogen atmosphere in the whole process of preparation, and is mechanically stirred at 200-300 r/min.
The invention has the beneficial effects that:
1. compared with the existing self-repairing polyurethane elastomer, the self-repairing polyurethane elastomer has excellent mechanical property of 32-50MPa and super-strong toughness of 420-740 MJ/m 3 And a self-healing efficiency of up to 95% within 100 min.
2. Compared with most of self-repairing polyurethane elastomers at present, the self-repairing polyurethane elastomer has excellent rebound resilience, the material is circularly stretched to 1000%, and the dissipation energy is almost completely recovered after the material is kept at 20 ℃ for 15 min.
3. The invention has excellent thermal stability.
4. Compared with most of self-repairing polyurethane elastomers at present, the invention can realize multiple recycling.
5. The preparation method is simple, convenient to operate, has the characteristic of excellent recovery, and has strong practicability.
Drawings
FIG. 1 shows the polymer synthesis of the present invention.
FIG. 2 is a mechanical property test of the present invention.
Fig. 3 is a self-healing test of the present invention.
FIG. 4 is a recyclability test of the present invention.
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the invention. 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.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present invention. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof. The invention will be further described with reference to specific examples.
In the following examples, the following test methods were employed:
the tensile test is carried out according to national standard GB/T1024.2-2006 with the test speed of 100mm/min at room temperature.
The cyclic stretching experiments were carried out according to GB/T1024.2-2006 test at a speed of 100mm/min at room temperature.
Example 1
Into a 100ml three-necked flask, polycarbonate diol (2000 g/mol and 500 g/mol) (4 g), 4' -dicyclohexylmethane diisocyanate (1.30 g), DBTDL (0.02 g) and N at 80℃were charged with dimethylacetamide as a solvent 2 Under the atmosphere, the mixture was mechanically stirred for 1 hour to obtain a colorless viscous prepolymer. 4,4 '-diaminodiphenyl sulfide (0.25 g) was dispersed in a DMAC solvent, and 4,4' -diaminodiphenyl sulfide dispersed in DMAC (10 ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 9 hours. After the reaction is finished, placing the mixture in a three-neck flask for 9 hours to obtain a dimethyl acetamide solution of viscous self-repairing polyurethane, pouring the solvent into a tetrafluoro mold, and drying the mixture at 80 ℃, wherein the high-toughness polyurethane has stress of 32MPa and strain of 4720%.
Experimental example 2
Polycarbonate diol (2000 g/mol and 500 g/mol) (4 g), 4' -dicyclohexylmethane diisocyanate (1.56 g), DBTDL (0.02 g) were added to a 100ml three-necked flask with dimethylacetamide as a solvent, and the mixture was mechanically stirred at 80℃under N2 for 1 hour to obtain a colorless viscous prepolymer. 4,4 '-diaminodiphenyl sulfide (0.50 g) was dispersed in a DMAC solvent, and 4,4' -diaminodiphenyl sulfide dispersed in DMAC (10 ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 9 hours. After the reaction is finished, placing the mixture in a three-neck flask for 9 hours to obtain a viscous dimethylacetamide solution of self-repairing polyurethane, pouring the solvent into a tetrafluoro mold, and drying the mixture at 80 ℃, wherein the high-toughness polyurethane has stress of 39MPa and strain of 4230%.
Experimental example 3
Polycarbonate diol (2000 g/mol and 500 g/mol) (4 g), 4' -dicyclohexylmethane diisocyanate (1.82 g), DBTDL (0.02 g) were added to a 100ml three-necked flask with dimethylacetamide as a solvent, and the mixture was mechanically stirred at 80℃under N2 for 1 hour to obtain a colorless viscous prepolymer. 4,4 '-diaminodiphenyl sulfide (0.74 g) was dispersed in a DMAC solvent, and 4,4' -diaminodiphenyl sulfide dispersed in DMAC (10 ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 9 hours. After the reaction is finished, placing the mixture in a three-neck flask for 9 hours to obtain a dimethyl acetamide solution of viscous self-repairing polyurethane, pouring the solvent into a tetrafluoro mold, and drying the mixture at 80 ℃, wherein the high-toughness polyurethane has stress of 47MPa and strain of 3901%.
Comparative example 1
Into a 100ml three-necked flask, polycarbonate diol (2000 g/mol and 500 g/mol) (4 g), hexamethylene diisocyanate (1.04 g), DBTDL (0.02 g) were added using dimethylacetamide as a solvent, and the mixture was mechanically stirred for 1 hour at 80℃under an N2 atmosphere to obtain a colorless viscous solution prepolymer. 4,4 '-diaminodiphenyl sulfide (0.40 g) was dispersed in a DMAC (10 ml) solvent, and the 4,4' -diaminodiphenyl sulfide dispersed in DMAC (10 ml) was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 9 hours. After the reaction is finished, placing the mixture in a three-neck flask for 9 hours to obtain a viscous dimethylacetamide solution of self-repairing polyurethane, pouring the solvent into a tetrafluoro mold, and drying the mixture at 80 ℃, wherein the high-toughness polyurethane has 49MPa and strain 3450%.
Comparative example 2
To a 100ml three-necked flask, polycarbonate diol (2000 g/mol) (6 g), 4' -dicyclohexylmethane diisocyanate (1.56 g g) and DBTDL (0.02 g) were added with dimethylacetamide as a solvent, and the mixture was mechanically stirred at 80℃under an N2 atmosphere for 2 hours to obtain a colorless viscous solution prepolymer. 4,4 '-diaminodiphenyl sulfide (0.40 g) was dispersed in DMAC (10 ml) solvent, and 4,4' -diaminodiphenyl sulfide dispersed in 10ml solvent was slowly added to the vessel and mechanically stirred under nitrogen atmosphere for 9 hours. After the reaction is finished, placing the mixture in a three-neck flask for 9 hours to obtain a viscous dimethylacetamide solution of self-repairing polyurethane, pouring the solvent into a tetrafluoro mold, and drying the mixture at 80 ℃, wherein the high-toughness polyurethane has 42MPa and 3760% strain.
Detailed data are shown in Table I
The polyurethane elastomer prepared by the invention has excellent tensile strength, elongation at break and quick self-repairing performance, and the price of the required raw materials is moderate, so that the polyurethane elastomer is expected to realize industrial production.
While the foregoing description of the embodiments of the present invention has been presented in conjunction with the drawings, it should be understood that it is not intended to limit the scope of the invention, but rather, it is intended to cover all modifications or variations within the scope of the invention as defined by the claims of the present invention.
Claims (7)
1. The preparation of the super-toughness polyurethane elastomer is characterized in that the super-toughness polyurethane elastomer is synthesized by taking polycarbonate diols with different molecular weights as soft segments and 4,4' -diaminodiphenyl disulfide as chain extension in the presence of a catalyst.
2. The material of claim 1, wherein the composite has a tensile strength of 32 to 50MPa; the toughness is 420-740 MJ/m3.
3. The material of claim 1, wherein the molar ratio of 4,4 '-dicyclohexylmethane diisocyanate, polycarbonate diol (2000 g/mol), polycarbonate diol (500 g/mol), 4' -diaminodiphenyl disulfide is 6:1 to 3:1 to 3:1 to 4.
4. A preparation method of a super-toughness polyurethane crosslinked network is characterized in that 4,4' -dicyclohexylmethane diisocyanate, polycarbonate diol (2000 g/mol) and polycarbonate diol (500 g/mol) are used as starting materials, and end capping reaction is completed in a dimethylacetamide solvent. 4,4' -diaminodiphenyl disulfide is used for chain extension to prepare the super-toughness polyurethane elastomer.
5. The process for preparing a super tough polyurethane elastomer as claimed in claim 4The structural formula of the polyurethane elastomer is as follows:
6. the process for preparing a super tough polyurethane elastomer according to claim 5, wherein the polycarbonate diol (2000 g/mol and 500 g/mol) accounts for 25 to 40% of the total content of the elastomer.
7. The polyurethane elastomer according to claim 6, wherein the carbonate diol (2000 g/mol and 500 g/mol) molar ratio is from 1 to 3:1 to 4.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180312623A1 (en) * | 2017-04-28 | 2018-11-01 | Liang Wang | Polyurethane Elastomer with High Ultimate Elongation |
| KR20190083551A (en) * | 2018-01-04 | 2019-07-12 | 한국과학기술연구원 | Self healing elastomer, self healing complex and self healing film |
| CN111303377A (en) * | 2020-02-18 | 2020-06-19 | 中国科学院化学研究所 | High-strength self-repairing polyurethane urea elastomer and preparation method thereof |
| WO2022169317A1 (en) * | 2021-02-08 | 2022-08-11 | 한국화학연구원 | High-strength self-healing polyurethane polymer having room-temperature self-healing function |
| CN114933723A (en) * | 2022-06-06 | 2022-08-23 | 青岛科技大学 | Preparation method of super-tough polyurethane crosslinked network |
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- 2022-11-16 CN CN202211434398.0A patent/CN116284638A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180312623A1 (en) * | 2017-04-28 | 2018-11-01 | Liang Wang | Polyurethane Elastomer with High Ultimate Elongation |
| KR20190083551A (en) * | 2018-01-04 | 2019-07-12 | 한국과학기술연구원 | Self healing elastomer, self healing complex and self healing film |
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