CN115873252A - Urethane-based elastomer and preparation method thereof - Google Patents
Urethane-based elastomer and preparation method thereof Download PDFInfo
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- CN115873252A CN115873252A CN202211409354.2A CN202211409354A CN115873252A CN 115873252 A CN115873252 A CN 115873252A CN 202211409354 A CN202211409354 A CN 202211409354A CN 115873252 A CN115873252 A CN 115873252A
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- based elastomer
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 229920001971 elastomer Polymers 0.000 title claims abstract description 47
- 239000000806 elastomer Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 27
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 238000007259 addition reaction Methods 0.000 claims abstract description 17
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 15
- -1 mercapto compound Chemical class 0.000 claims abstract description 15
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 14
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000005770 Eugenol Substances 0.000 claims abstract description 13
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960002217 eugenol Drugs 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000012650 click reaction Methods 0.000 claims abstract description 7
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract description 7
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000001681 protective effect Effects 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims 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 claims description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000012974 tin catalyst Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 230000002441 reversible effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 230000008439 repair process Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002520 smart material Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Polyurethanes Or Polyureas (AREA)
Abstract
The invention belongs to the technical field of elastomer materials, and particularly relates to a urethane-based elastomer and a preparation method thereof. The preparation method comprises the following steps: mixing hexamethylene diisocyanate, eugenol and benzene solvents, and performing addition reaction under the conditions of protective atmosphere and catalyst to obtain a urethane-based compound; mixing the urethane-based compound and a mercapto compound, and carrying out mercapto click reaction under the ultraviolet irradiation condition to obtain a urethane-based elastomer; the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate. The self-healing efficiency of the ester-based elastomer prepared by the preparation method provided by the invention is higher.
Description
Technical Field
The invention belongs to the technical field of elastomer materials, and particularly relates to a urethane-based elastomer and a preparation method thereof.
Background
The elastomer is a very important high polymer material, and has wide application prospect in the fields of adhesives, coatings, electronic and electric appliances, aerospace, tires, clothes, soft robots and the like due to high mechanical toughness and elasticity. Moreover, with the development of soft robot smart materials, elastomers with high mechanical toughness and elasticity are also more and more widely applied in the field of electronic skins. However, when the elastomer bears strong physical and mechanical actions in the service process, the internal structure of the elastomer is easy to generate fatigue and microcracks, which leads to material functional failure, shortens the service life of the elastomer, and cannot fully exert the self-function to cause the waste of global resources, so the elastomer with self-healing performance is urgently needed at present and is a hot spot researched by modern students.
At present, the preparation method reported in the literature can only prepare self-healing elastomers with single reversible bonds (such as single reversible bonds including D-a (Diels-Alder) bonds, disulfide bonds, ester bonds, hydrogen bonds and the like), and realize reversible fluidity of molecular structures under the condition of external stimulation (light, heat and the like), so that the molecular chain structures of microscopically broken parts of the damaged parts of the materials can be crosslinked again, macroscopically cracked planes are refilled, and the self-healing function of the elastomer materials is realized. But the self-healing is realized by the single reversible chemical bond stimulation material, the self-healing efficiency is often low, for example, the self-healing degree can reach 90% to the maximum when the single D-A bond is at a temperature of more than 120 ℃ and the self-healing time is more than 1 h; the single disulfide bond can realize self-healing within 30min at the temperature of between 50 and 60 ℃, and the self-healing degree is generally between 80 and 90 percent.
Disclosure of Invention
In view of the above, the present invention provides a urethane-based elastomer and a preparation method thereof, and the self-healing efficiency of the ester-based elastomer prepared by the preparation method provided by the present invention is high.
In order to solve the problems, the invention provides a preparation method of a urethane-based elastomer, which comprises the steps of mixing hexamethylene diisocyanate, eugenol and benzene solvents, and carrying out addition reaction under the conditions of protective atmosphere and organic tin catalyst to obtain a urethane-based compound; mixing the urethane-based compound and a mercapto compound, and carrying out mercapto click reaction under the ultraviolet irradiation condition to obtain a urethane-based elastomer;
the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate.
Preferably, the organotin catalyst comprises dibutyltin dilaurate.
Preferably, the molar ratio of the hexamethylene diisocyanate to the eugenol is 1.5-2.5.
Preferably, the temperature of the addition reaction is 75-85 ℃, and the holding time is 1.5-2.5 h.
Preferably, the molar ratio of the urethane group in the urethane-based compound to the mercapto group in the mercapto compound is 1:0.95 to 1.05.
Preferably, the power of the ultraviolet irradiation is 95-110W, and the time is 5-15 min.
Preferably, after the addition reaction, the method further comprises the steps of cooling, solid-liquid separation, washing and drying the system obtained by the addition reaction in sequence.
Preferably, the cooling temperature is-5 to 0 ℃; the drying temperature is 75-85 ℃, and the drying time is 4-5 h.
The invention also provides the urethane-based elastomer prepared by the preparation method, which is characterized in that chemical bonds in the urethane-based elastomer comprise urethane bonds and hydrogen bonds.
Preferably, the molar ratio of the urethane bonds to the hydrogen bonds is 1:0.5.
the invention provides a preparation method of a urethane-based elastomer, which comprises the following steps: mixing hexamethylene diisocyanate, eugenol and benzene solvents, and carrying out addition reaction under the conditions of protective atmosphere and organic tin catalyst to obtain a urethane-based compound; mixing the urethane-based compound and a mercapto compound, and carrying out mercapto click reaction under the ultraviolet irradiation condition to obtain a urethane-based elastomer; the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate. The invention adopts hexamethylene diisocyanate with high reaction activity as a reaction site, and eugenol is utilized to seal the reaction site under the catalysis of dibutyltin dilaurate to generate a urethane-based compound, so that a characteristic group urethane group is introduced, and then the urethane-based elastomer is prepared through mercapto click reaction. The invention utilizes the thermoreversible characteristic that the urethane groups can be deblocked at high temperature and then resealed at low temperature, and the urethane bond molecular chains in the elastomer network can form a large number of hydrogen bonds due to the action of the urethane bonds, and the hydrogen bonds are dynamically converted along with the change of temperature, thereby improving the self-healing efficiency of the obtained urethane-based elastomer through the construction of two reversible chemical bonds (hydrogen bonds and urethane bonds).
Drawings
FIG. 1 is a schematic representation of the products EUHDI/3SH and EUHDI/4SH obtained in examples 1 and 2;
FIG. 2 is a scratch repair test chart of the products EUHDI/3SH and EUHDI/4SH obtained in example 1 and example 2;
FIG. 3 is a graph showing tensile strength tests carried out on the products EUHDI/3SH and EUHDI/4SH obtained in examples 1 and 2.
Detailed Description
The invention provides a preparation method of a urethane-based elastomer, which comprises the following steps:
mixing hexamethylene diisocyanate, eugenol and benzene solvents, and carrying out addition reaction under the conditions of protective atmosphere and organic tin catalyst to obtain a urethane-based compound;
mixing the urethane-based compound and a mercapto compound, and carrying out mercapto click reaction on the mixture under ultraviolet to obtain a urethane-based elastomer;
the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate.
The invention mixes hexamethylene diisocyanate, eugenol and benzene solvent, and carries out addition reaction under the conditions of protective atmosphere and organic tin catalyst to obtain the urethane-based compound.
In the present invention, the benzene-based solvent preferably includes toluene. In the present invention, the organotin catalyst preferably comprises dibutyltin dilaurate. In the present invention, the molar ratio of the hexamethylene diisocyanate to the eugenol is preferably 1.5 to 2.5, more preferably 1. In the present invention, the hexamethylene diisocyanate and the benzene-based solvent are preferably used in a ratio of 1g:12.5 to 14mL, more preferably 1g:13mL. In the present invention, the mass of the organotin catalyst is 0.04 to 0.06%, more preferably 0.05%, of the sum of the mass of hexamethylene diisocyanate and eugenol.
In the present invention, the temperature of the addition reaction is preferably 75 to 85 ℃, more preferably 80 ℃, and the time is preferably 1.5 to 2.5 hours, more preferably 2 hours. In the present invention, the addition reaction is preferably carried out under heating in a water bath. In the present invention, the atmosphere for protection of the addition reaction is preferably high-purity nitrogen gas, and the purity of the high-purity nitrogen gas is preferably 99.99%.
In the invention, the molecular chain structure of the urethane-based compound is highly symmetrical and has higher rigidity. Therefore, the urethane-based compound prepared by the invention has excellent mechanical properties.
In the present invention, after the addition reaction, it is preferable to further include cooling, solid-liquid separation, washing, and drying the system obtained by the addition reaction in this order.
In the present invention, the temperature of the cooling is preferably-5 to 0 ℃, more preferably 0 ℃. In the present invention, the cooling rate of the cooling is preferably 5 ℃/min. In the invention, white crystals are separated out in the cooling process, namely the urethane-based compound crude product. In the present invention, the solid-liquid separation is preferably performed by suction filtration, and the suction filtration is not particularly limited in the present invention, and may be performed by an operation known to those skilled in the art. In the present invention, the washing detergent is preferably absolute ethyl alcohol, the number of washing is preferably 2 to 3, and in the present invention, the washing is preferably carried out until no benzene-based solvent is present. In the present invention, the drying temperature is preferably 75 to 85 ℃, more preferably 80 ℃, and the time is preferably 4 to 5 hours, more preferably 4.5 hours.
After the urethane-based compound is obtained, the urethane-based compound and the mercapto compound are mixed, and mercapto click reaction is carried out under ultraviolet to obtain the urethane-based elastomer.
In the present invention, the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate. In the present invention, the molar ratio of the urethane group in the urethane-based compound to the mercapto group in the mercapto compound is preferably 1.
In the present invention, the power of the ultraviolet irradiation is preferably 95 to 110W, more preferably 100W; the time is preferably 5 to 15min, more preferably 10min.
The invention also provides the urethane-based elastomer prepared by the preparation method, and chemical bonds in the urethane-based elastomer comprise urethane bonds and hydrogen bonds.
In the present invention, the molar ratio of the urethane bond and the hydrogen bond in the urethane-based elastomer is preferably 1.
The repair method of the urethane-based elastomer of the invention preferably realizes self-healing of the urethane-based elastomer under certain temperature conditions. In the present invention, the temperature is preferably 25 to 150 ℃, more preferably 150 ℃.
In order to further illustrate the present invention, the following embodiments are provided to describe the technical solutions of the present invention in detail, but they should not be construed as limiting the scope of the present invention.
Example 1
Adding 118.9mmol of hexamethylene diisocyanate, 237.8mmol of eugenol, 0.5g of dibutyltin dilaurate and 260mL of toluene into a three-necked flask in an inert gas (99.99% high-purity nitrogen) atmosphere, heating to 80 ℃, heating in a water bath for 2 hours for reaction, changing the solution into milk white, cooling to 0 ℃, precipitating white crystals, performing suction filtration, washing the obtained crystals for 3 times with absolute ethyl alcohol, and drying in an oven at 80 ℃ for 4 hours to obtain 56.68g of urethane-based compound, wherein the yield is 96%;
the thus-obtained 3g of urethane-based compound was mixed with 6.017mmol of trimethylolpropane tris (3-mercaptopropionate), and irradiated under ultraviolet irradiation at a power of 100W for 10 minutes for crosslinking reaction to obtain a urethane-based elastomer, which was designated as EUHDI/3SH.
Example 2
Adding 59.45mol of hexamethylene diisocyanate, 118.9mol of eugenol, 0.25g of dibutyltin dilaurate and 130mL of toluene into a three-neck flask in an inert gas (99.99% high-purity nitrogen) atmosphere, heating to 80 ℃, heating in a water bath for 2 hours to react, wherein the solution is milky, cooling to 0 ℃, precipitating white crystals, performing suction filtration, washing the obtained crystals for 3 times with absolute ethyl alcohol, and drying in an oven at 80 ℃ for 4 hours to obtain 28.34g of urethane-based compound, wherein the yield is 96%;
3g of the urethane-based compound obtained and 9.025mol of pentaerythritol tetra-3-mercaptopropionate were mixed and irradiated under the ultraviolet irradiation condition of 100W for 10min for crosslinking reaction to obtain a urethane-based elastomer, which was recorded as EUHDI/4SH.
FIG. 1 is a schematic diagram of the products EUHDI/3SH and EUHDI/4SH obtained in examples 1 and 2, wherein FIG. 1A is a schematic diagram of EUHDI/3SH, and FIG. 1B is a schematic diagram of EUHDI/4SH, and it can be seen from FIG. 1 that: the crosslinking density of the EUHDI/3SH polymer network is higher than that of the EUHDI/4SH polymer.
The invention carries out scratch repair test on the products EUHDI/3SH and EUHDI/4SH prepared in the embodiment 1 and the embodiment 2, and the test method comprises the following steps: heating the urethane-based elastomer to 150 ℃ to achieve self-healing, and obtaining the result shown in FIG. 2, wherein FIG. 2 (A) is a state diagram before EUHDI/3SH repair; FIG. 2 (A) ， ) Is EUA state diagram after HDI/3SH repair; FIG. 2 (B) is a diagram showing the state before EUHDI/4SH repair; FIG. 2 (B) ， ) Is a state diagram after EUHDI/4SH repair. As can be seen from fig. 2: after the EUHDI/3SH is repaired, the self-healing degree is close to 100%, and after the EUHDI/4SH is repaired, the self-healing degree can reach more than 90%, wherein the repairing time of the EUHDI/3SH is 30min, and the repairing time of the EUHDI/4SH is 30min.
The tensile strength of the products EUHDI/3SH and EUHDI/4SH prepared in examples 1 and 2 is tested by the method of mechanical tensile test, the test result is shown in FIG. 3, and the following results can be seen in FIG. 3: the tensile strength of the EUHDI/3SH original sample strip is 4.20MPa, the tensile strength of the sample strip after the heat treatment of the cut sample strip is 3.8MPa, the mechanical property can be recovered to 90.5 percent of that of the original sample strip, and the self-healing effect is relatively ideal. The tensile strength of the EUHDI/4SH original sample strip is 19.95MPa, the tensile strength of the sample strip subjected to heat treatment after cutting is 15.11MPa, the mechanical strength can be recovered to 75.7% of that of the original sample strip, and the reversible collision of a dynamic bond is influenced because the crosslinking density of the EUHDI/4SH elastomer is greater than that of the EUHDI/3SH elastomer, so that the self-healing efficiency of the EUHDI/4SH elastomer is lower than that of the EUHDI/3SH elastomer. In summary, the crosslinking density of the polymer structure affects the occurrence of reversible reactions of reversible bonds, and thus affects the self-healing efficiency.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and improvements can be made without departing from the principle of the present invention, and these modifications and improvements should also be considered as the protection scope of the present invention.
Claims (10)
1. A method for preparing a urethane-based elastomer, comprising the steps of:
mixing hexamethylene diisocyanate, eugenol and benzene solvents, and carrying out addition reaction under the conditions of protective atmosphere and organic tin catalyst to obtain a urethane-based compound;
mixing the urethane-based compound and a mercapto compound, and carrying out mercapto click reaction under the ultraviolet irradiation condition to obtain a urethane-based elastomer;
the mercapto compound includes trimethylolpropane tris (3-mercaptopropionate) or pentaerythritol tetrakis-3-mercaptopropionate.
2. The method of claim 1, wherein the organotin catalyst comprises dibutyltin dilaurate.
3. The method according to claim 1, wherein the molar ratio of the hexamethylene diisocyanate to the eugenol is 1.5 to 2.5.
4. The process according to any one of claims 1 to 3, wherein the temperature of the addition reaction is 75 to 85 ℃ and the holding time is 1.5 to 2.5 hours.
5. The method according to claim 1, wherein the molar ratio of the urethane group in the urethane-based compound to the mercapto group in the mercapto compound is 1:0.95 to 1.05.
6. The method according to claim 1, wherein the power of the ultraviolet irradiation is 95 to 110W and the time is 5 to 15min.
7. The method according to claim 1, wherein after the addition reaction, the method further comprises cooling, separating solid from liquid, washing and drying the system obtained by the addition reaction in this order.
8. The method of claim 7, wherein the cooling temperature is-5 to 0 ℃; the drying temperature is 75-85 ℃, and the drying time is 4-5 h.
9. The urethane-based elastomer obtained by the production process according to any one of claims 1 to 8, wherein the chemical bonds in the urethane-based elastomer include urethane bonds and hydrogen bonds.
10. The urethane-based elastomer according to claim 9, wherein the molar ratio of the urethane bonds to the hydrogen bonds is 1:0.5.
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| FR2163872A5 (en) * | 1971-12-03 | 1973-07-27 | Grace W R Ltd | Polyenes prodn - for reacting with polythiols to yield curable resins |
| US6008296A (en) * | 1995-04-19 | 1999-12-28 | Optima, Inc. | Optical terpolymer of polyisocyanate, polythiol and polyene monomers |
| US20040254258A1 (en) * | 2002-07-08 | 2004-12-16 | Hiroshi Horikoshi | Polymerizable composition, optical material comprising the composition and method for producing the material |
| CN108484912A (en) * | 2018-03-14 | 2018-09-04 | 江西科技师范大学 | A kind of eugenol based high-temp-resistant self-healing polymers and preparation method thereof |
| CN109942773A (en) * | 2019-03-18 | 2019-06-28 | 四川大学 | A kind of selfreparing polyurethane and preparation method thereof of the key of thiourethane containing dynamic |
| CN114163598A (en) * | 2021-12-24 | 2022-03-11 | 中国林业科学研究院林产化学工业研究所 | Self-repairing polyurethane derived from bio-based polyol and preparation method thereof |
-
2022
- 2022-11-11 CN CN202211409354.2A patent/CN115873252B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2163872A5 (en) * | 1971-12-03 | 1973-07-27 | Grace W R Ltd | Polyenes prodn - for reacting with polythiols to yield curable resins |
| US6008296A (en) * | 1995-04-19 | 1999-12-28 | Optima, Inc. | Optical terpolymer of polyisocyanate, polythiol and polyene monomers |
| US20040254258A1 (en) * | 2002-07-08 | 2004-12-16 | Hiroshi Horikoshi | Polymerizable composition, optical material comprising the composition and method for producing the material |
| CN108484912A (en) * | 2018-03-14 | 2018-09-04 | 江西科技师范大学 | A kind of eugenol based high-temp-resistant self-healing polymers and preparation method thereof |
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| CN114163598A (en) * | 2021-12-24 | 2022-03-11 | 中国林业科学研究院林产化学工业研究所 | Self-repairing polyurethane derived from bio-based polyol and preparation method thereof |
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