CN117186828B - Damping vibration attenuation and sound insulation airtight adhesive and preparation method thereof - Google Patents
Damping vibration attenuation and sound insulation airtight adhesive and preparation method thereof Download PDFInfo
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- CN117186828B CN117186828B CN202311474354.5A CN202311474354A CN117186828B CN 117186828 B CN117186828 B CN 117186828B CN 202311474354 A CN202311474354 A CN 202311474354A CN 117186828 B CN117186828 B CN 117186828B
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- vibration attenuation
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- 238000013016 damping Methods 0.000 title claims abstract description 42
- 238000009413 insulation Methods 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 239000000853 adhesive Substances 0.000 title claims abstract description 7
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 7
- 239000000945 filler Substances 0.000 claims abstract description 34
- 239000003292 glue Substances 0.000 claims abstract description 34
- 238000007789 sealing Methods 0.000 claims abstract description 31
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 9
- 229920000570 polyether Polymers 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000007822 coupling agent Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000004014 plasticizer Substances 0.000 claims abstract description 7
- 239000013008 thixotropic agent Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000565 sealant Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical group CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 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 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical group CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 claims description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 239000006230 acetylene black Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000012945 sealing adhesive Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 230000009467 reduction Effects 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 9
- 230000006355 external stress Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012621 metal-organic framework Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Abstract
The invention belongs to the technical field of sound insulation vibration reduction sealing glue, and in particular relates to damping vibration reduction sound insulation sealing glue and a preparation method thereof, wherein the damping vibration reduction sound insulation sealing glue is prepared from the following raw materials in parts by weight: 80-120 parts of polyether polyol, 20-36 parts of MDI (diphenyl methane diisocyanate), 5-12 parts of modified filler, 20-30 parts of plasticizer, 1-3 parts of coupling agent, 0.3-0.6 part of catalyst and 1-2 parts of thixotropic agent; MOF-HLs and TDI are heated and mixed in a nonpolar organic solvent to react, so that modified filler is obtained, and the damping vibration attenuation and noise reduction performance and the tensile strength and the elongation are improved obviously by introducing the modified filler. The increase of the tensile strength can improve the adhesive force of the sealing glue; the elongation rate is improved, and the sealing glue can bear deformation better when being subjected to external stress, so that a better sealing effect is provided.
Description
Technical Field
The invention belongs to the technical field of sound insulation vibration reduction airtight glue, and particularly relates to damping vibration reduction sound insulation airtight glue and a preparation method thereof.
Background
The harm of noise pollution to the health and daily life of people is increasingly important, and in the environments of people production and life, glass windows of buildings, vehicles and the like are required to use sealing glue with good damping, sound insulation and vibration reduction effects so as to reduce the influence of external noise and body vibration.
The sealing glue is used to bond two surfaces of two objects together or to fill the gap of material, and has sealing effect and strong adhesion.
The existing sealing glue improves the damping, sound-insulating and vibration-reducing effects of the sealing glue by adding solid particle fillers with larger energy-absorbing effect, but the existing solid particle fillers have poor compatibility with a sealing glue system and poor energy-absorbing effect, so that the sealing glue cannot achieve the ideal damping, vibration-reducing and vibration-reducing effects.
Disclosure of Invention
The invention aims to solve the technical problem of providing damping vibration attenuation and sound insulation airtight glue and a preparation method thereof, and the damping vibration attenuation and sound insulation performance is improved.
The invention provides damping vibration attenuation and sound insulation airtight glue which is prepared from the following raw materials in parts by weight:
80-120 parts of polyether polyol, 20-36 parts of MDI (diphenyl methane diisocyanate), 5-12 parts of modified filler, 20-30 parts of plasticizer, 1-3 parts of coupling agent, 0.3-0.6 part of catalyst and 1-2 parts of thixotropic agent; wherein MDI is diphenylmethane diisocyanate;
the modified filler is prepared from the following raw materials in percentage by mass:
the mass ratio of MOF-HLs to TDI is 1 (1-1.2); heating and mixing MOF-HLs and TDI in a nonpolar organic solvent to react to obtain modified filler;
the plasticizer is dioctyl phthalate; the coupling agent is a silane coupling agent; the catalyst is one or two of dibutyl tin dilaurate and triethylamine; the thixotropic agent is fumed silica, acetylene black and modified calcium carbonate.
Wherein the amino alcohol is grafted onto the open metal sites of MOFs, resulting in MOF-HLs (a metal organic framework consisting of hydroxyl ligands), MOF-HLs comprising Ui0-66 (Zr) or MFM-300 (Al).
Optionally, the preparation method of the modified filler comprises the following steps:
weighing MOF-HLs and TDI according to the mass ratio, firstly adding MOF-HLs into a nonpolar organic solvent, then adding TDI under the condition of heating and stirring, keeping the temperature, and continuously stirring for reaction for not less than 2 hours; after the reaction is finished, cooling, filtering, washing, removing unreacted raw materials by using a polar organic solvent, filtering by suction, and drying to obtain the modified filler.
Optionally, the polar organic solvent is DMF, methanol, ethanol, isopropanol, or acetone.
Optionally, the nonpolar organic solvent is benzene, toluene or carbon tetrachloride.
Optionally, the heating temperature in the preparation method of the modified filler is 70-80 ℃.
Alternatively, the TDI is diluted 3-5 times with toluene and added over 5-10 minutes in the preparation method of the modified filler.
Optionally, the polyether polyol is PPG or PTMG.
Optionally, the silane coupling agent is vinyl triethoxysilane or 3-aminopropyl trimethoxysilane.
A preparation method of damping vibration attenuation sound insulation airtight glue comprises the steps of heating and mixing polyether polyol and MDI to obtain a component A; and mixing the modified filler, the plasticizer, the coupling agent, the catalyst and the thixotropic agent to obtain a component B, and heating and uniformly mixing the component A and the component B to obtain the damping vibration attenuation sound insulation sealing adhesive.
Optionally, the polyether polyol and MDI are mixed at a temperature of 50 to 60 ℃; the temperature of the mixture of the component A and the component B is 70-85 ℃.
The damping vibration attenuation and sound insulation airtight glue has the beneficial effects that the damping vibration attenuation and noise reduction performance is obviously improved by introducing the modified filler, and meanwhile, the tensile strength and the elongation are improved. The increase of the tensile strength can improve the adhesive force of the sealing glue; the elongation rate is improved, and the sealing glue can bear deformation better when being subjected to external stress, so that a better sealing effect is provided.
Detailed Description
The present invention will be further described in detail with reference to specific embodiments in order to make the objects, technical solutions and advantages of the present invention more apparent.
Example 1
Preparing a modified filler, comprising the steps of:
weighing the raw materials: adding MOF-HLs into toluene at a mass ratio of Ui0-66 (Zr) to TDI of 1:1.1, heating to 70 ℃, adding TDI under continuous stirring, maintaining the temperature, and continuously stirring for reaction for 2h; after the reaction is finished, cooling to room temperature, filtering, washing twice with ethanol, filtering, and vacuum drying at 50 ℃ for 6 hours to obtain the modified filler.
Preparing damping vibration attenuation and sound insulation sealing glue:
weighing the raw materials in parts by weight, and preparing a component A: mixing 80 parts of PPG and 26 parts of MDI at 55 ℃ under stirring to obtain a component A;
and (3) preparation of a component B: 5.5 parts of modified filler, 25 parts of dioctyl phthalate, 1 part of vinyl triethoxysilane, 0.2 part of dibutyltin dilaurate, 0.2 part of triethylamine and 1.5 parts of aerosil are uniformly mixed to obtain a component B;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Example 2
And (3) preparation of the component A: mixing 80 parts of PPG and 26 parts of MDI at 55 ℃ under stirring to obtain a component A;
and (3) preparation of a component B: 8 parts of modified filler, 25 parts of dioctyl phthalate, 1 part of coupling agent, 0.3 part of catalyst and 1.5 parts of aerosil are uniformly mixed to obtain a component B;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Example 3
And (3) preparation of the component A: mixing 80 parts of PPG and 26 parts of MDI at 55 ℃ under stirring to obtain a component A; and (3) preparation of a component B: 12 parts of modified filler, 25 parts of dioctyl phthalate, 1 part of vinyl triethoxysilane, 0.2 part of dibutyl tin dilaurate, 0.2 part of triethylamine and 1.5 parts of aerosil are uniformly mixed to obtain a component B; and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Example 4
Preparing a modified filler, comprising the steps of:
weighing the raw materials: ui0-66 (Zr) was changed to MFM-300 (Al), and the rest was the same as in example 1.
Preparing damping vibration attenuation and sound insulation sealing glue:
and (3) preparation of the component A: stirring and mixing 110 parts of PTMG and 35 parts of MDI at 55 ℃ to obtain a component A;
and (3) preparation of a component B: 8 parts of modified filler, 25 parts of dioctyl phthalate, 1 part of 3-aminopropyl trimethoxy silane, 0.2 part of dibutyltin dilaurate, 0.2 part of triethylamine and 1.5 parts of aerosil are uniformly mixed to obtain a component B;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Comparative example 1
And (3) preparation of the component A: the same as in example 1;
and (3) preparation of a component B: the remainder was the same as in example 1, except that no modified filler was added;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Comparative example 2
And (3) preparation of the component A: the same as in example 1;
and (3) preparation of a component B: the modified filler was changed to 8 parts of Ui0-66 (Zr) and the rest was the same as in example 1;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Comparative example 3
And (3) preparation of the component A: the same as in example 1;
and (3) preparation of a component B: the modified filler was changed to 8 parts of MFM-300 (Al), and the rest was the same as in example 1;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
Comparative example 4
And (3) preparation of the component A: the same as in example 1;
and (3) preparation of a component B: the modified filler is replaced by 8 parts of talcum powder, and the rest is the same as in example 1;
and uniformly mixing the component A and the component B at 70 ℃ to obtain the damping vibration attenuation sound insulation sealing glue.
The damping vibration attenuation and sound insulation airtight glue obtained in the embodiment and the comparative example is subjected to adhesion, tensile strength, elongation and noise reduction performance test, and the damping vibration attenuation performance is tested according to GBT 16406-1996 standard; noise reduction performance test: and (3) adhering 6 pieces of toughened glass which are the same with the damping vibration attenuation and sound insulation sealant obtained in each embodiment and the comparative example to form a square box, manufacturing noise at a distance of 2 meters from the square box, detecting a decibel value by a noise meter in the square box, and detecting a reference decibel value of the noise meter, which is 2 meters away from a noise source, outside the square box, wherein the difference value between the reference decibel value and the in-vehicle detection decibel value is the noise reduction performance. The results are shown in Table 1.
TABLE 1
As shown by the test results in Table 1, the damping vibration attenuation and noise reduction performance of the damping vibration attenuation and noise reduction airtight adhesive provided by the invention is obviously improved by introducing the modified filler, and meanwhile, the tensile strength and the elongation are improved. The increase of the tensile strength can improve the adhesive force of the sealing glue; the elongation rate is improved, and the sealing glue can bear deformation better when being subjected to external stress, so that a better sealing effect is provided.
Those of ordinary skill in the art will appreciate that: the discussion of any of the embodiments above is merely exemplary and is not intended to imply that the scope of the present application is limited to such examples; combinations of features of the above embodiments or in different embodiments are also possible within the spirit of the application, steps may be implemented in any order, and there are many other variations of the different aspects of one or more embodiments described above which are not provided in detail for the sake of brevity.
One or more embodiments herein are intended to embrace all such alternatives, modifications and variations that fall within the broad scope of the present application. Any omissions, modifications, equivalents, improvements, and the like, which are within the spirit and principles of the one or more embodiments in the present application, are therefore intended to be included within the scope of the present application.
Claims (10)
1. The damping vibration attenuation and sound insulation airtight adhesive is characterized by comprising the following raw materials in parts by weight:
80-120 parts of polyether polyol, 20-36 parts of MDI (diphenyl methane diisocyanate), 5-12 parts of modified filler, 20-30 parts of plasticizer, 1-3 parts of coupling agent, 0.3-0.6 part of catalyst and 1-2 parts of thixotropic agent;
the modified filler is prepared from the following raw materials in percentage by mass:
the mass ratio of MOF-HLs to TDI is 1 (1-1.2); heating and mixing MOF-HLs and TDI in a nonpolar organic solvent to react to obtain modified filler;
the plasticizer is dioctyl phthalate;
the coupling agent is a silane coupling agent;
the catalyst is one or two of dibutyl tin dilaurate and triethylamine;
the thixotropic agent is any one or more of fumed silica, acetylene black and modified calcium carbonate.
2. The damping vibration attenuation and sound insulation sealant according to claim 1, wherein the preparation method of the modified filler comprises the following steps:
weighing MOF-HLs and TDI according to the mass ratio, firstly adding MOF-HLs into a nonpolar organic solvent, then adding TDI under the condition of heating and stirring, keeping the temperature, and continuously stirring for reaction for not less than 2 hours; after the reaction is finished, cooling, filtering, washing, removing unreacted raw materials by using a polar organic solvent, filtering by suction, and drying to obtain the modified filler.
3. Damping vibration attenuation and sound insulation sealant according to claim 1 or 2, characterized in that the MOF-HLs is uo-66 (Zr) or MFM-300 (Al).
4. The damping vibration attenuation and sound insulation sealant according to claim 2, wherein the polar organic solvent is DMF, methanol, ethanol, isopropanol or acetone; the nonpolar organic solvent is benzene, toluene or carbon tetrachloride.
5. The damping vibration attenuation and sound insulation sealing glue according to claim 2, wherein the heating temperature in the preparation method of the modified filler is 70-80 ℃.
6. The damping vibration attenuation and sound insulation sealing glue according to claim 2, wherein in the preparation method of the modified filler, TDI is diluted 3-5 times by toluene and added for 5-10 min.
7. The damping vibration attenuation and sound insulation sealant according to claim 1, wherein the polyether polyol is PPG or PTMG.
8. The damping vibration attenuation and sound insulation sealant according to claim 1, wherein the silane coupling agent is vinyl triethoxysilane or 3-aminopropyl trimethoxysilane.
9. A method for preparing the damping vibration attenuation and sound insulation sealant according to any one of claims 1 to 8, wherein polyether polyol and MDI are heated and mixed to obtain a component a; and mixing the modified filler, the plasticizer, the coupling agent, the catalyst and the thixotropic agent to obtain a component B, and heating and uniformly mixing the component A and the component B to obtain the damping vibration attenuation sound insulation sealing adhesive.
10. The method for preparing the damping vibration attenuation and sound insulation sealant according to claim 9, wherein the mixing temperature of the polyether polyol and the MDI is 50-60 ℃; the temperature of the mixture of the component A and the component B is 70-85 ℃.
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| CN202311474354.5A CN117186828B (en) | 2023-11-08 | 2023-11-08 | Damping vibration attenuation and sound insulation airtight adhesive and preparation method thereof |
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| CN202311474354.5A CN117186828B (en) | 2023-11-08 | 2023-11-08 | Damping vibration attenuation and sound insulation airtight adhesive and preparation method thereof |
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| CN117186828B true CN117186828B (en) | 2024-01-12 |
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| KR20160095229A (en) * | 2015-02-02 | 2016-08-11 | 주식회사 우레아텍 | Poly-urethane manufacturing method using n_2 adsorbent |
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| CN114350300A (en) * | 2022-02-22 | 2022-04-15 | 江苏特丽亮镀膜科技有限公司 | Novel low-VOC conductive adhesive for chip packaging and preparation method thereof |
| WO2022171564A1 (en) * | 2021-02-11 | 2022-08-18 | Basf Se | Reduction of monomeric isocyanates by porous material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US11074899B2 (en) * | 2018-03-15 | 2021-07-27 | International Business Machines Corporation | VOC sequestering acoustic foam |
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- 2023-11-08 CN CN202311474354.5A patent/CN117186828B/en active Active
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| KR20160095229A (en) * | 2015-02-02 | 2016-08-11 | 주식회사 우레아텍 | Poly-urethane manufacturing method using n_2 adsorbent |
| CN109206577A (en) * | 2017-06-30 | 2019-01-15 | 翁秋梅 | A kind of energy-absorbing method based on dynamic aggregation object |
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