CN102898611B - Preparation method for organic silicon polyurethane adhesive - Google Patents
Preparation method for organic silicon polyurethane adhesive Download PDFInfo
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- CN102898611B CN102898611B CN201210334026.0A CN201210334026A CN102898611B CN 102898611 B CN102898611 B CN 102898611B CN 201210334026 A CN201210334026 A CN 201210334026A CN 102898611 B CN102898611 B CN 102898611B
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- organic silicon
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- epoxy resin
- reacts
- polyethers
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 42
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 42
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 34
- 239000010703 silicon Substances 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000001070 adhesive effect Effects 0.000 title abstract description 16
- 239000000853 adhesive Substances 0.000 title abstract description 13
- 229920000570 polyether Polymers 0.000 claims abstract description 21
- 239000003822 epoxy resin Substances 0.000 claims abstract description 19
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229920005906 polyester polyol Polymers 0.000 claims description 9
- -1 polysiloxane Polymers 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 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 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 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 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 230000035939 shock Effects 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000010358 mechanical oscillation Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000005050 vinyl trichlorosilane Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- UNIYDALVXFPINL-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propylsilicon Chemical compound CC(=C)C(=O)OCCC[Si] UNIYDALVXFPINL-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000004826 Synthetic adhesive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- FHTQCUNSKSWOHF-UHFFFAOYSA-N ethyl carbamate;silicon Chemical compound [Si].CCOC(N)=O FHTQCUNSKSWOHF-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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CN201210334026.0A CN102898611B (en) | 2012-09-11 | 2012-09-11 | Preparation method for organic silicon polyurethane adhesive |
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CN201210334026.0A CN102898611B (en) | 2012-09-11 | 2012-09-11 | Preparation method for organic silicon polyurethane adhesive |
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CN102898611A CN102898611A (en) | 2013-01-30 |
CN102898611B true CN102898611B (en) | 2014-03-26 |
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Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105238326A (en) * | 2015-09-21 | 2016-01-13 | 太仓市金锚新材料科技有限公司 | Polyurethane adhesive and preparation method thereof |
CN107151307A (en) * | 2017-04-24 | 2017-09-12 | 苏州金枪新材料股份有限公司 | A kind of organic silicon modified polyurethane sealant |
CN109868104B (en) * | 2019-02-28 | 2021-06-29 | 苏州金枪新材料股份有限公司 | Flexible epoxy adhesive and preparation method thereof |
CN112358842A (en) * | 2020-09-29 | 2021-02-12 | 无锡市佳盛高新改性材料有限公司 | Preparation method of organic silicon polyurethane adhesive |
CN113583616A (en) * | 2021-06-28 | 2021-11-02 | 美国Wefv技术控股集团有限公司 | Adhesive with high polymerization, strong adhesion and good weather resistance and preparation method thereof |
CN113845623A (en) * | 2021-09-28 | 2021-12-28 | 泉州师范学院 | Low-temperature-resistant flexible polyurethane photosensitive resin composition containing silicon chain for photocuring 3D printing and preparation method thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092547A (en) * | 2007-07-17 | 2007-12-26 | 金坛市胶粘剂厂 | Dedicated adhesive for bagging liquid pesticide |
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2012
- 2012-09-11 CN CN201210334026.0A patent/CN102898611B/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092547A (en) * | 2007-07-17 | 2007-12-26 | 金坛市胶粘剂厂 | Dedicated adhesive for bagging liquid pesticide |
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C53 | Correction of patent of invention or patent application | ||
C56 | Change in the name or address of the patentee |
Owner name: SUZHOU GOLDEN GUN NEW MATERIALS CO., LTD. Free format text: FORMER NAME: SUZHOU ADHESIVE FACTORY CO., LTD. |
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CB03 | Change of inventor or designer information |
Inventor after: Cao Jianqiang Inventor after: Lu Jianming Inventor after: Zhang Jun Inventor before: Cao Jianqiang |
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Free format text: CORRECT: INVENTOR; FROM: CAO JIANQIANG TO: CAO JIANQIANG LU JIANMING ZHANG JUN |
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CP03 | Change of name, title or address |
Address after: 215000 Jiangsu city in Suzhou Province town of Xiangcheng District Wong Tai Pan Yang Industrial Park Road No. 10 spring Patentee after: SUZHOU JINQIANG NEW MATERIALS Co.,Ltd. Address before: 215143 Jiangsu city in Suzhou Province town of Xiangcheng District Wong Tai Pan Yang Industrial Park and Suzhou Road, adhesive factory Co. Ltd. Patentee before: SUZHOU ADHESIVE FACTORY Co.,Ltd. |
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EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20130130 Assignee: Suzhou ronghua Leasing Co.,Ltd. Assignor: SUZHOU JINQIANG NEW MATERIALS Co.,Ltd. Contract record no.: X2020320010027 Denomination of invention: Preparation of silicone polyurethane adhesive Granted publication date: 20140326 License type: Exclusive License Record date: 20201203 |
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Denomination of invention: Preparation of silicone polyurethane adhesive Effective date of registration: 20201207 Granted publication date: 20140326 Pledgee: Suzhou ronghua Leasing Co.,Ltd. Pledgor: SUZHOU JINQIANG NEW MATERIALS Co.,Ltd. Registration number: Y2020320010218 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Suzhou ronghua Leasing Co.,Ltd. Assignor: SUZHOU JINQIANG NEW MATERIALS Co.,Ltd. Contract record no.: X2020320010027 Date of cancellation: 20231210 |
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Date of cancellation: 20231211 Granted publication date: 20140326 Pledgee: Suzhou ronghua Leasing Co.,Ltd. Pledgor: SUZHOU JINQIANG NEW MATERIALS Co.,Ltd. Registration number: Y2020320010218 |
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