CN115785887B - High-temperature-resistant heat-conducting polyurethane structural adhesive and preparation method thereof - Google Patents
High-temperature-resistant heat-conducting polyurethane structural adhesive and preparation method thereof Download PDFInfo
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- CN115785887B CN115785887B CN202211536743.1A CN202211536743A CN115785887B CN 115785887 B CN115785887 B CN 115785887B CN 202211536743 A CN202211536743 A CN 202211536743A CN 115785887 B CN115785887 B CN 115785887B
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 36
- 239000000853 adhesive Substances 0.000 title claims abstract description 34
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 27
- 239000004814 polyurethane Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 229920005862 polyol Polymers 0.000 claims abstract description 26
- 150000003077 polyols Chemical class 0.000 claims abstract description 25
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 16
- 239000000945 filler Substances 0.000 claims abstract description 15
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 13
- 239000004359 castor oil Substances 0.000 claims abstract description 13
- 235000019438 castor oil Nutrition 0.000 claims abstract description 13
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004970 Chain extender Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000012948 isocyanate Substances 0.000 claims abstract description 10
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 10
- 239000013008 thixotropic agent 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
- 230000002745 absorbent Effects 0.000 claims abstract description 8
- 239000002250 absorbent Substances 0.000 claims abstract description 8
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- YPACMOORZSDQDQ-UHFFFAOYSA-N 3-(4-aminobenzoyl)oxypropyl 4-aminobenzoate Chemical group C1=CC(N)=CC=C1C(=O)OCCCOC(=O)C1=CC=C(N)C=C1 YPACMOORZSDQDQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- MTEZSDOQASFMDI-UHFFFAOYSA-N 1-trimethoxysilylpropan-1-ol Chemical compound CCC(O)[Si](OC)(OC)OC MTEZSDOQASFMDI-UHFFFAOYSA-N 0.000 claims description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical class C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 229960004063 propylene glycol Drugs 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 claims description 2
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 claims description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 claims description 2
- LJAGLQVRUZWQGK-UHFFFAOYSA-N oxecane-2,10-dione Chemical compound O=C1CCCCCCCC(=O)O1 LJAGLQVRUZWQGK-UHFFFAOYSA-N 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 11
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical group CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 238000004806 packaging method and process Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 238000010008 shearing Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- SPAUYKHQVLTCOL-UHFFFAOYSA-N C1(=CC=CC=C1)OP(OC1=CC=CC=C1)(O)=O.C1(=CC=CC=C1)C Chemical compound C1(=CC=CC=C1)OP(OC1=CC=CC=C1)(O)=O.C1(=CC=CC=C1)C SPAUYKHQVLTCOL-UHFFFAOYSA-N 0.000 description 1
- 244000119298 Emblica officinalis Species 0.000 description 1
- 235000015489 Emblica officinalis Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- -1 small molecule polyol Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention belongs to the technical field of polyurethane adhesives, and particularly relates to a high-temperature-resistant heat-conducting polyurethane structural adhesive and a preparation method thereof. The component A comprises the following components in percentage by mass: 5.0 to 15.0 percent of polyether polyol, 3.0 to 7.0 percent of chain extender, 3.5 to 16.0 percent of modified castor oil, 0 to 5.0 percent of diluent, 65.0 to 80.0 percent of heat conducting filler, 0.1 to 2.0 percent of thixotropic agent, 0.5 to 1.0 percent of silane coupling agent, 0.5 to 4.0 percent of first water absorbent and 0.01 to 0.3 percent of catalyst; and the component B comprises the following components: 12.0% -25.0% of isocyanate, 5.0% -12.0% of polyester polyol, 0.1% -0.3% of second water absorbent, 65.0% -80.0% of heat conducting filler, 0.1% -2.0% of thixotropic agent and 0.5% -1.0% of silane coupling agent. It has good thermal conductivity, excellent high temperature resistance, good adhesion and toughness.
Description
Technical Field
The invention belongs to the technical field of polyurethane adhesives, and particularly relates to a high-temperature-resistant heat-conducting polyurethane structural adhesive and a preparation method thereof.
Background
In recent years, the new energy automobile industry has been developed at a high speed, the corresponding power battery installation amount has also been increased rapidly, the heat conduction structural adhesive is used as the necessary adhesive between the liquid cooling plate and the battery core of the battery, and the demand thereof will also be increased greatly.
The existing power battery has rapid development speed, but the safety and the cruising performance of the existing power battery are still to be improved. In addition, along with the transition evolution of the original module of the assembly structure of the power battery into the current battery core which is directly integrated on the chassis, the requirement of the heat conduction structural adhesive used in the power battery is also continuously increased. The heat-conducting structural adhesive needs to meet the requirements of main indexes such as heat conductivity coefficient, adhesiveness, flexibility and the like, and also needs to meet the performance at high temperature, for example, the tensile strength of the heat-conducting structural adhesive needs to reach more than 5MPa under the typical high-temperature condition of 60 ℃. In the past, the adhesive property of the heat-conducting structural adhesive under the high temperature condition is insufficient and the toughness is poor, which is a great pain point in the industry.
Disclosure of Invention
The technical problem to be solved by the invention is to provide the high-temperature-resistant heat-conducting polyurethane structural adhesive which has good heat-conducting property, excellent high-temperature resistance and good bonding property and toughness at high temperature; the invention also provides a scientific, reasonable, simple and feasible preparation method.
The high-temperature-resistant heat-conducting polyurethane structural adhesive is prepared from a component A and a component B, wherein:
the component A consists of the following raw materials in percentage by mass:
5.0-15.0% of polyether polyol
3.0 to 7.0 percent of chain extender
3.5 to 16.0 percent of modified castor oil
0 to 5.0% of diluent
65.0 to 80.0 percent of heat conducting filler
Thixotropic agent 0.1-2.0%
Silane coupling agent 0.5-1.0%
0.5-4.0% of a first water absorbent
0.01% -0.3% of catalyst;
the component B comprises the following raw materials in percentage by mass:
isocyanate 12.0-25.0%
5.0-12.0% of polyester polyol
0.1-0.3% of a second water absorbent
65.0 to 80.0 percent of heat conducting filler
Thixotropic agent 0.1-2.0%
0.5% -1.0% of silane coupling agent.
The polyether polyol is one or more of polyol with 3 functionality or polyol with 4-5 functionality, wherein the number average molecular weight of the polyol with 3 functionality is 300-800; the number average molecular weight of the polyol with 4-5 functionality is 500-1000.
The chain extender is 1, 3-propanediol bis (4-aminobenzoate).
The modified castor oil is H-368 of Earthway oil Co.
The diluent is one or more of phthalate, aliphatic dibasic acid ester and phosphate.
The heat conducting filler is one or more of aluminum oxide, magnesium oxide, aluminum nitride, boron nitride, aluminum hydroxide, magnesium hydroxide and silicon carbide.
The thixotropic agent is hydrophobic fumed silica.
The silane coupling agent is one or more of beta- (3, 4-epoxycyclohexyl) ethyl trimethoxy silane, gamma-glycidic acid oxypropyl trimethoxy silane and gamma-hydrophobic propyl trimethoxy silane.
The first water absorbing agent is a molecular sieve.
The catalyst is one or more of bismuth catalysts, zinc catalysts, amine catalysts and tin catalysts.
The isocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, carbodiimide modified isocyanate, dicyclohexylmethane diisocyanate and polymethylene polyphenyl isocyanate.
The polyester polyol is prepared by condensation reaction of small molecular dibasic acid and small molecular polyol, the number average molecular weight is 1000-3000, and the functionality is 2.01-2.1.
The small molecular dibasic acid is a mixture of aliphatic dibasic acid or anhydride and aromatic dibasic acid or anhydride, wherein the aliphatic dibasic acid or anhydride is selected from one or more of adipic acid, azelaic acid, sebacic acid, adipic anhydride, azelaic anhydride and sebacic anhydride; the aromatic dibasic acid or anhydride is selected from one or more of phthalic acid, isophthalic acid, terephthalic acid and phthalic anhydride.
The small molecular polyol consists of small molecular triol and small molecular dihydric alcohol containing branched chains, wherein the small molecular triol is selected from one or more of trimethylolpropane, trimethylolethane and glycerol, and the small molecular dihydric alcohol containing branched chains is selected from one or more of 1, 2-propanediol, 2-methyl-1, 3-propanediol, 3-methyl-1, 5-pentanediol, neopentyl glycol and trimethylpentanediol.
The second water-absorbing agent is p-Toluenesulfonyl Isocyanate (TI).
The preparation method of the high-temperature-resistant heat-conducting polyurethane structural adhesive comprises the following steps:
(1) Preparation of component A
Adding polyether polyol, a chain extender, modified castor oil, a diluent, a heat-conducting filler and a silane coupling agent into a reactor according to a proportion, heating to 100-120 ℃, vacuumizing and dehydrating for 2 hours, cooling to normal temperature, adding the rest components, vacuumizing and stirring uniformly to obtain a component A;
(2) Preparation of component B
Adding polyester polyol and isocyanate into a reactor, heating to 80-100 ℃, preserving heat for 2-5 hours, cooling to room temperature, and adding a second water absorbent to prepare a prepolymer; adding the heat conducting filler, the thixotropic agent and the silane coupling agent into the prepolymer, and vacuumizing and stirring uniformly to obtain a component B;
(3) And mixing the component A and the component B to obtain the high-temperature-resistant heat-conducting polyurethane structural adhesive.
When in use, the component A and the component B are generally filled into a 1:1 plastic double-tube package for sealing and preservation, and are matched with each other according to the volume ratio of 1:1.
Compared with the prior art, the invention has the beneficial effects that:
1. according to the invention, by introducing the diamine chain extender 1, 3-propylene glycol bis (4-aminobenzoate), the bonding performance of the heat-conducting polyurethane structural adhesive at high temperature can be remarkably improved, and the high temperature resistance of the heat-conducting polyurethane structural adhesive is further improved by matching the modified castor oil with high temperature resistance and the aromatic polyester polyol.
2. The high-temperature-resistant heat-conducting polyurethane structural adhesive has good heat-conducting performance, products with different heat-conducting coefficients can be obtained by adjusting the formula, the high-temperature-resistant heat-conducting polyurethane structural adhesive has excellent high-temperature resistance under different heat-conducting coefficients, and good bonding performance and toughness can be maintained at high temperature.
3. The preparation method has simple and reasonable process, easily obtained raw materials and convenient industrialized production.
Detailed Description
The technical scheme of the present invention will be clearly and completely described in the following examples.
All materials used in the examples are commercially available, except as specified.
The parameters of the raw materials used are as follows:
DV125: polyether polyol, number average molecular weight 375, functionality 3, shandong blue Star Dong Co., ltd;
NJ-6209: polyether polyol, number average molecular weight 675, functionality 4-5, sentence-Ningwu New Material Co., ltd;
740M: chain extender, 1, 3-propanediol bis (4-aminobenzoate), new material stock, inc. Of xiangyuan, su;
h-368: modified castor oil, number average molecular weight 720, functionality 2.5, embrane oil company;
LAV: unmodified castor oil, number average molecular weight 940, functionality 2.7, emblic oil company;
CDP: a diluent, toluene diphenyl phosphate, isman technologies Co., ltd;
GD-U151: the heat-conducting filler is a heat-conducting filler compounded by aluminum oxide and aluminum hydroxide, and is available from Guangdong Jin Ge New Material Co., ltd;
GD-U206: the heat-conducting filler is a heat-conducting filler compounded by aluminum oxide and aluminum hydroxide, and is available from Guangdong Jin Ge New Material Co., ltd;
XH-202: thixotropic agents, hydrophobic fumed silica, win the creation of chemical engineering, inc;
KH560: silane coupling agent, gamma-glycidic acid oxypropyl trimethoxysilane, isman technology Co;
HX-G103: a first water-absorbing agent, molecular sieve, large Lian Haixin chemical company, inc;
CB-18: a catalyst, bismuth neodecanoate, available from taixing city Cheng Ling, inc;
t-12: catalyst, dibutyl tin dilaurate, a winning chemical company, inc;
CD-C: carbodiimide-modified isocyanate, number average molecular weight 300, kechuang polymer chinese limited;
MDI-100: diphenylmethane diisocyanate, number average molecular weight 250, smoke counter Wanhua chemical group Co., ltd;
HMDI: dicyclohexylmethane diisocyanate, number average molecular weight 262, bayer, germany;
PE-1103: self-made polyester polyol with a molecular weight of 3000 and a functionality of 2.01, wherein small molecular dibasic acid is adipic acid and terephthalic acid with a molar ratio of 1:1, and small molecular polyol is trimethylolpropane and 1, 2-propylene glycol;
PE-1104: self-made polyester polyol with a molecular weight of 2000 and a functionality of 2.04, wherein small molecule dibasic acid is azelaic acid and isophthalic acid with a molar ratio of 1:1, and small molecule polyol is trimethylolethane and 2-methyl-1, 3-propanediol;
PE-1105: self-made polyester polyol with the molecular weight of 1000 and the functionality of 2.1, wherein small molecular dibasic acid is sebacic acid and phthalic anhydride with the molar ratio of 1:1, and small molecular polyol is glycerin and neopentyl glycol;
PE-1106: the self-made polyester polyol has a molecular weight of 3000 and a functionality of 2.01, wherein the micromolecular dibasic acid is adipic acid, and the micromolecular polyol is trimethylolpropane and 1, 3-propylene glycol.
The preparation process of the self-made polyester polyol comprises the following steps:
putting small molecular polyol and small molecular dibasic acid into a reaction kettle, heating to 130 ℃ to start esterification reaction of the system, controlling the top temperature of the reaction kettle not to exceed 101 ℃, heating the system to 180-200 ℃, adding tetrabutyl titanate serving as a catalyst, continuously heating to perform esterification dehydration reaction, and vacuumizing the system when the water yield of the system reaches 90-95% of the theoretical water yield to 220-250 ℃, and performing polycondensation dealcoholization reaction; and after the reaction is finished, cooling to 100-140 ℃ and discharging to obtain the self-made polyester polyol.
Example 1
The preparation step of the component A comprises the following steps:
the total weight of the component A is 100 parts, 5 parts of DV125, 5 parts of NJ-6209, 3 parts of 740M, 12.3 parts of H-368, 70 parts of GD-U151 and 0.8 part of KH560 are added into a reactor, the temperature is raised to 100 ℃, the mixture is vacuumized and dehydrated for 2 hours and then cooled to normal temperature, then 1.6 parts of XH-202, 2 parts of HX-G103 and 0.3 part of CB-18 are added, and the mixture is vacuumized and stirred uniformly to obtain the component A;
the preparation step of the component B comprises the following steps:
the total weight of the component B is 100 parts, 5.6 parts of PE-1103 and 21.8 parts of CD-C are put into a reactor, the temperature is raised to 80 ℃ and kept for 2 hours, 0.2 part of TI is added after the temperature is reduced to room temperature, and the prepolymer is prepared for standby after stirring and barreling; then 70 parts of GD-U151, 1.6 parts of XH-202 and 0.8 part of KH560 are added into the prepolymer, and the mixture is vacuumized and stirred uniformly to obtain a component B;
and (3) packaging the component A and the component B into a 1:1 plastic double-tube package for sealing and storing, and matching the components according to the volume ratio of 1:1.
Example 2
The preparation step of the component A comprises the following steps:
the total weight of the component A is 100 parts, 4 parts of DV125, 1 part of NJ-6209, 7 parts of 740M, 7.5 parts of H-368, 4 parts of CDP, 70 parts of GD-U151 and 0.8 part of KH560 are added into a reactor, the temperature is raised to 110 ℃, the mixture is vacuumized and dehydrated for 2 hours and then cooled to normal temperature, 1.6 parts of XH-202, 4 parts of HX-G103 and 0.1 part of T-12 are added, and the mixture is vacuumized and stirred uniformly to obtain the component A;
the preparation step of the component B comprises the following steps:
the total weight of the component B is 100 parts, 11.5 parts of PE-1104 and 16 parts of MDI-100 are put into a reactor, the temperature is raised to 90 ℃ and kept for 3 hours, 0.1 part of TI is added after the temperature is reduced to the room temperature, and a prepolymer is prepared for standby; then 70 parts of GD-U151, 1.6 parts of XH-202 and 0.8 part of KH560 are added into a reactor, and the mixture is vacuumized and stirred uniformly to obtain a component B;
and (3) packaging the component A and the component B into a 1:1 plastic double-tube package for sealing and storing, and matching the components according to the volume ratio of 1:1.
Example 3
The preparation step of the component A comprises the following steps:
the total weight of the component A is 100 parts, 9 parts of DV125, 3 parts of NJ-6209, 3 parts of 740M, 6.45 parts of H-368, 1 part of CDP, 74 parts of GD-U206 and 1 part of KH560 are added into a reactor, the temperature is raised to 120 ℃, the mixture is vacuumized and dehydrated for 2 hours and then cooled to normal temperature, then 0.4 part of XH-202, 2 parts of HX-G103, 0.1 part of CB-18 and 0.05 part of T-12 are added, and the mixture is vacuumized and stirred uniformly to obtain the component A;
the preparation step of the component B comprises the following steps:
the total weight of the component B is 100 parts, 5.6 parts of PE-1103 and 18.8 parts of MDI-100 are put into a reactor, the temperature is raised to 100 ℃ and kept for 3 hours, 0.2 part of TI is added after the temperature is reduced to the room temperature, and a prepolymer is prepared for standby; then 74 parts of GD-U206, 0.4 part of XH-202 and 1 part of KH560 are added into the prepolymer, and the mixture is vacuumized and stirred uniformly to obtain a component B;
and (3) packaging the component A and the component B into a 1:1 plastic double-tube package for sealing and storing, and matching the components according to the volume ratio of 1:1.
Example 4
The preparation step of the component A comprises the following steps:
the total weight of the component A is 100 parts, 5 parts of DV125, 2 parts of NJ-6209, 7 parts of 740M, 3.5 parts of H-368, 5 parts of CDP, 74 parts of GD-U206 and 1 part of KH560 are added into a reactor, the temperature is raised to 100 ℃, the mixture is vacuumized and dehydrated for 2 hours and then cooled to normal temperature, then 0.4 part of XH-202, 2 parts of HX-G103 and 0.1 part of CB-18 are added, and the mixture is vacuumized and stirred uniformly to obtain the component A;
the preparation step of the component B comprises the following steps:
the total weight of the component B is 100 parts, 6.8 parts of PE-1105 and 17.6 parts of HMDI are firstly put into a reactor, the temperature is raised to 90 ℃ and kept for 5 hours, 0.2 part of TI is added after the temperature is reduced to room temperature, and a prepolymer is prepared for standby; then 74 parts of GD-U206, 0.4 part of XH-202 and 1 part of KH560 are added into the prepolymer, and the mixture is vacuumized and stirred uniformly to obtain a component B;
and (3) packaging the component A and the component B into a 1:1 plastic double-tube package for sealing and storing, and matching the components according to the volume ratio of 1:1.
Example 5
The preparation step of the component A comprises the following steps:
the total weight of the component A is 100 parts, 7 parts of DV125, 1 part of NJ-6209, 5 parts of 740M, 15.97 parts of H-368, 3 parts of CDP, 65 parts of GD-U151 and 0.5 part of KH560 are added into a reactor, the temperature is raised to 100 ℃, the mixture is vacuumized and dehydrated for 2 hours and then cooled to normal temperature, 2 parts of XH-202, 0.5 part of HX-G103 and 0.03 part of T-12 are added, and the mixture is vacuumized and stirred uniformly to obtain the component A;
the preparation step of the component B comprises the following steps:
the total weight of the component B is 100 parts, 8.2 parts of PE-1105, 14 parts of MDI-100 and 10 parts of CD-C are firstly put into a reactor, the temperature is raised to 80 ℃ for 3 hours, 0.3 part of TI is added after the temperature is reduced to the room temperature, and a prepolymer is prepared for standby; adding 65 parts of GD-U151, 2 parts of XH-202 and 0.5 part of KH560 into the prepolymer, vacuumizing and stirring uniformly to obtain a component B;
and (3) packaging the component A and the component B into a 1:1 plastic double-tube package for sealing and storing, and matching the components according to the volume ratio of 1:1.
Comparative example 1
This comparative example 1 was different from example 1 in that 740M in the A-component was replaced with an equivalent weight part of H-368, i.e., the amount of H-368 added in the A-component was 15.3 parts, CD-C in the B-component was changed to 20.5 parts, and PE-1103 was changed to 6.9 parts, which was the same as in example 1.
Comparative example 2
This comparative example 2 differs from example 1 in that the polyester polyol in the B component was replaced with PE-1106 in the same parts by weight as PE-1103, and was the same as example 1.
Comparative example 3
This comparative example 3 differs from example 1 in that the modified castor oil in the a-component was replaced by an equivalent weight fraction of unmodified castor oil LAV from H-368, all in the same way as example 1.
Performance test:
tensile strength and tensile modulus are tested in reference to GB/T528-2009 test for tensile stress Strain Performance of vulcanized rubber or thermoplastic rubber;
the heat conductivity coefficient is tested by referring to GB/T10294-2008 standard test of heat insulation material steady state thermal resistance and related characteristic measurement protection hot plate method;
the shear strength is tested by referring to GB/T7124-2008 "determination of tensile shear Strength of adhesive", wherein the preparation method of the shear test piece comprises the following steps: a, B components are uniformly mixed according to a volume ratio of 1:1, a PET blue film which is not subjected to prime coating and surface treatment and 3003 aluminum materials are mutually adhered to prepare a shearing test piece, the thickness of adhesive layers on two sides of the PET blue film is controlled to be 0.2mm, the shearing test piece is cured for 7 days under the environment of temperature (23+/-2) DEG C and relative humidity (50+/-5)% RH, and the shearing strength is tested.
Specific performance indices are shown in table 1 below.
Table 1 Performance index of polyurethane structural adhesives prepared in examples 1 to 5 and comparative examples 1 to 3
As can be seen from table 1, the polyurethane structural adhesive with different heat conductivity coefficients can be prepared by adjusting the proportion of the raw materials, so that the requirement of the heat conductivity coefficient grade of the product is met;
the tensile modulus at 23 ℃ is lower than 1000MPa, and the polyurethane structural adhesive meets the industry requirements and has good toughness.
By comparing example 1 with comparative example 1, the thermal conductivity is at the same level, and the shear strength and the tensile strength of example 1 at 60 ℃ are both higher than those of comparative example 1, which demonstrates that the addition of the chain extender 1, 3-propanediol bis (4-aminobenzoate) can significantly improve the adhesive properties of the thermally conductive polyurethane structural adhesive at high temperatures.
By comparing example 1 with comparative examples 2 and 3, the thermal conductivity is at the same level, and the shear strength and tensile strength of example 1 at 60 ℃ are higher than those of comparative examples 2 and 3, which demonstrates that the addition of the aromatic polyester polyol and the modified castor oil H-368 is beneficial to improving the bonding performance of the thermally conductive polyurethane structural adhesive at high temperature.
Claims (7)
1. The utility model provides a high temperature resistant heat conduction polyurethane structural adhesive which characterized in that: is prepared from a component A and a component B, wherein:
the component A consists of the following raw materials in percentage by mass:
5.0-15.0% of polyether polyol
3.0 to 7.0 percent of chain extender
3.5 to 16.0 percent of modified castor oil
0 to 5.0% of diluent
65.0 to 80.0 percent of heat conducting filler
Thixotropic agent 0.1-2.0%
Silane coupling agent 0.5-1.0%
0.5-4.0% of a first water absorbent
0.01% -0.3% of catalyst;
the component B comprises the following raw materials in percentage by mass:
isocyanate 12.0-25.0%
5.0-12.0% of polyester polyol
0.1-0.3% of a second water absorbent
65.0 to 80.0 percent of heat conducting filler
Thixotropic agent 0.1-2.0%
0.5% -1.0% of silane coupling agent;
the chain extender is 1, 3-propylene glycol bis (4-aminobenzoate);
modified castor oil is H-368;
the polyester polyol is prepared by condensation reaction of small molecular dibasic acid and small molecular polyol, the number average molecular weight is 1000-3000, and the functionality is 2.01-2.1;
the small molecular dibasic acid is a mixture of aliphatic dibasic acid or anhydride and aromatic dibasic acid or anhydride.
2. The high temperature resistant, thermally conductive polyurethane structural adhesive of claim 1, wherein: the polyether polyol is one or more of polyol with 3 functionality or polyol with 4-5 functionality, wherein the polyol with 3 functionality has a number average molecular weight of 300-800, and the polyol with 4-5 functionality has a number average molecular weight of 500-1000.
3. The high temperature resistant, thermally conductive polyurethane structural adhesive of claim 1, wherein: the silane coupling agent is one or more of beta- (3, 4-epoxycyclohexyl) ethyl trimethoxy silane, gamma-glycidic acid oxypropyl trimethoxy silane and gamma-hydrophobic propyl trimethoxy silane.
4. The high temperature resistant, thermally conductive polyurethane structural adhesive of claim 1, wherein: the isocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, carbodiimide modified isocyanate, dicyclohexylmethane diisocyanate and polymethylene polyphenyl isocyanate.
5. The high temperature resistant, thermally conductive polyurethane structural adhesive of claim 1, wherein: the aliphatic dibasic acid or anhydride is selected from one or more of adipic acid, azelaic acid, sebacic acid, adipic anhydride, azelaic anhydride and sebacic anhydride; the aromatic dibasic acid or anhydride is selected from one or more of phthalic acid, isophthalic acid, terephthalic acid and phthalic anhydride.
6. The high temperature resistant, thermally conductive polyurethane structural adhesive of claim 1, wherein: the small molecular polyol consists of small molecular triol and small molecular dihydric alcohol containing branched chains, wherein the small molecular triol is selected from one or more of trimethylolpropane, trimethylolethane and glycerol, and the small molecular dihydric alcohol containing branched chains is selected from one or more of 1, 2-propanediol, 2-methyl-1, 3-propanediol, 3-methyl-1, 5-pentanediol, neopentyl glycol and trimethylpentanediol.
7. A method for preparing the high-temperature-resistant heat-conducting polyurethane structural adhesive according to any one of claims 1 to 6, which is characterized by comprising the following steps:
(1) Preparation of component A
Adding polyether polyol, a chain extender, modified castor oil, a diluent, a heat-conducting filler and a silane coupling agent into a reactor, heating to 100-120 ℃, vacuumizing for dehydration, cooling to normal temperature, adding the rest components, vacuumizing and stirring uniformly to obtain a component A;
(2) Preparation of component B
Adding polyester polyol and isocyanate into a reactor, heating to 80-100 ℃, preserving heat for 2-5 hours, cooling to room temperature, and adding a second water absorbent to prepare a prepolymer; adding the heat conducting filler, the thixotropic agent and the silane coupling agent into the prepolymer, and vacuumizing and stirring uniformly to obtain a component B;
(3) And mixing the component A and the component B to obtain the high-temperature-resistant heat-conducting polyurethane structural adhesive.
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| KR20120118657A (en) * | 2011-04-19 | 2012-10-29 | 주식회사 화승티엔씨 | Polyurethane adhesive composition in improving bonding strength for nylon shoe material |
| KR101248479B1 (en) * | 2012-03-20 | 2013-04-02 | (주)엠텍스 | Hot melt type urethane adhesives resin composition |
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