CN104945429A - 有机硅化合物、粘合剂组合物和制品 - Google Patents
有机硅化合物、粘合剂组合物和制品 Download PDFInfo
- Publication number
- CN104945429A CN104945429A CN201510131665.0A CN201510131665A CN104945429A CN 104945429 A CN104945429 A CN 104945429A CN 201510131665 A CN201510131665 A CN 201510131665A CN 104945429 A CN104945429 A CN 104945429A
- Authority
- CN
- China
- Prior art keywords
- formula
- group
- integer
- silicoorganic compound
- key
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000000853 adhesive Substances 0.000 title abstract description 3
- 230000001070 adhesive effect Effects 0.000 title abstract description 3
- 150000003961 organosilicon compounds Chemical class 0.000 title abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000011521 glass Substances 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000000463 material Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000011230 binding agent Substances 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003365 glass fiber Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012764 mineral filler Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000011152 fibreglass Substances 0.000 claims description 3
- 239000011086 glassine Substances 0.000 claims description 3
- 238000013507 mapping Methods 0.000 claims description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 22
- 229920005989 resin Polymers 0.000 abstract description 13
- 239000011347 resin Substances 0.000 abstract description 13
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 7
- 239000011147 inorganic material Substances 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 238000004381 surface treatment Methods 0.000 abstract description 2
- 239000004593 Epoxy Substances 0.000 abstract 1
- 230000001464 adherent effect Effects 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 1
- -1 catechol structure compound Chemical class 0.000 description 21
- 239000002585 base Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012756 surface treatment agent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- MTCBLMPRPUTXHZ-UHFFFAOYSA-N n-(oxomethylidene)nitramide Chemical group [O-][N+](=O)N=C=O MTCBLMPRPUTXHZ-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 230000010062 adhesion mechanism Effects 0.000 description 2
- 125000002009 alkene group Chemical group 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000002924 oxiranes Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- KQEIJFWAXDQUPR-UHFFFAOYSA-N 2,4-diaminophenol;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(O)C(N)=C1 KQEIJFWAXDQUPR-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- AVTLBBWTUPQRAY-BUHFOSPRSA-N V-59 Substances CCC(C)(C#N)\N=N\C(C)(CC)C#N AVTLBBWTUPQRAY-BUHFOSPRSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 125000000373 fatty alcohol group Chemical group 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- JISVIRFOSOKJIU-UHFFFAOYSA-N hexylidene Chemical group [CH2+]CCCC[CH-] JISVIRFOSOKJIU-UHFFFAOYSA-N 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/002—Priming paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/21—Paper; Textile fabrics
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5455—Silicon-containing compounds containing nitrogen containing at least one group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/12—Ceramic
- C09J2400/123—Ceramic in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/14—Glass
- C09J2400/143—Glass in the substrate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/26—Presence of textile or fabric
- C09J2400/263—Presence of textile or fabric in the substrate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
Abstract
分子中具有可水解的甲硅烷基和儿茶酚基团的有机硅化合物是新颖的。当通过用包含所述有机硅化合物的粘合剂组合物表面处理改性时,各种无机材料如玻璃和金属变得与环氧和其它树脂紧密粘合。
Description
相关申请的交叉引用
本非临时申请在美国法典第35卷第119节(a)款下要求2014年3月25日于日本提交的第2014-061196号的专利申请的优先权,所述专利申请的全部内容通过引用并入本文。
技术领域
本发明涉及在分子中具有可水解的甲硅烷基和儿茶酚结构的有机硅化合物、包含所述化合物的粘合剂组合物,和包括用所述组合物处理的基材的制品。
背景技术
由地中海贻贝生产的粘合蛋白是极佳的水下粘合剂。最近的研究致力于该粘合剂蛋白的特殊化学结构和利用所述化学结构的粘合机理。尽管关于所述粘合机理仍然存在许多待了解之处,已知的是粘合剂中的儿茶酚结构化合物具有重要作用。
专利文献1描述了形成聚多巴胺薄膜以改进镀覆引线框与环氧树脂或有机硅树脂之间的粘合性。非专利文献1公开了通过甲硅烷基保护的含乙烯基的儿茶酚化合物与含巯基的有机硅之间的硫醇-烯反应合成甲硅烷基保护的含儿茶酚的有机硅及其在粘合剂组合物中的用途。
在一些实例中,如上文所述,将儿茶酚结构的化合物用作粘合剂组合物的成分。然而,已知的是没有提及在分子中具有可水解的甲硅烷基和儿茶酚基团的有机硅化合物和包含所述有机硅化合物的粘合剂组合物的报道。
引用列表
专利文献1:JP-A 2010-144148
非专利文献1:J.Am.Chem.Soc.2012,134,20139-20145
发明简述
本发明的目的在于提供分子中具有可水解的甲硅烷基和儿茶酚基团的有机硅化合物、包含所述化合物的粘合剂组合物,和包括用所述组合物处理的基材的制品。
在一个方面,本发明提供了式(1)的有机硅化合物:
其中,R1至R4各自独立地选自氢;经取代或未取代的一价烃基,其可以被选自醚键、硫醚键(thioether bond)、羰基键和硫代羰基键中的至少一个键隔开;和式(2)至(5)的有机基团;且R1至R4中的至少一个为式(2)至(5)的有机基团中的任一个:
其中,R5为经取代或未取代的二价烃基,其可以被选自醚键、硫醚键、羰基键、硫代羰基键、氨基键、氨基甲酸酯键和脲键中的至少一个键隔开,R6为1至10个碳原子的烷基或6至10个碳原子的芳基,R7为1至20个碳原子的烷基、2至10个碳原子的烯基、6至10个碳原子的芳基或1至20个碳原子的酰基,n为1至3的整数,并且波浪线表示与苯环的成键位点。
在一个优选的实施方案中,式(2)为式(6)至(10)的任一种:
其中,m为1至8的整数,s为1至8的整数,R6、R7、n和波浪线如上文所定义,和Me为甲基。
在一个优选的实施方案中,式(3)为式(11)或(12):
其中,R6、R7、n、m、s和波浪线如上文所定义。
在一个优选的实施方案中,式(4)为式(13)或(14):
其中,R6、R7、n、m、s和波浪线如上文所定义。
在一个优选的实施方案中,式(5)为式(15):
其中,R6、R7、n、m和波浪线如上文所定义。
在另一方面,本发明提供了包含如上文所定义的有机硅化合物的粘合剂组合物。
在另外的方面,本发明提供了包括具有用上文所定义的粘合剂组合物处理的表面的基材的制品。所述基材典型地为玻璃纤维产品,选自玻璃布、玻璃带、玻璃毡和玻璃纸;无机填料;或陶瓷或金属基材。
本发明的有益效果
本发明的有机硅化合物在分子中同时具有可水解的甲硅烷基和儿茶酚基团。当通过用包含所述有机硅化合物的粘合剂组合物表面处理改性时,各种无机材料如玻璃和金属变得与树脂紧密粘合。
优选实施方案的描述
如本文中所使用的术语“硅烷偶联剂”被“有机硅化合物”所包括。
有机硅化合物
本发明的有机硅化合物或硅烷偶联剂的特征在于具有结构(i)和(ii)二者:
(i)可水解的甲硅烷基,和
(ii)儿茶酚基团。
具有结构(i)和(ii)二者的一系列化合物由下式(1)的有机硅化合物表示。
其中,R1至R4各自独立地选自氢;任选取代的一价烃基,其可以被选自醚键、硫醚键、羰基键和硫代羰基键中的至少一个键隔开;和式(2)至(5)的有机基团。R1至R4中的至少一个必须为选自式(2)至(5)的有机基团。
其中,R5为任选取代的二价烃基,其可以被选自醚键、硫醚键、羰基键、硫代羰基键、氨基键、氨基甲酸酯键和脲键中的至少一个键隔开,R6为1至10个碳原子的烷基或6至10个碳原子的芳基,R7为1至20个碳原子的烷基、2至10个碳原子的烯基、6至10个碳原子的芳基或1至20个碳原子的酰基,n为1至3的整数,和波浪线表示与苯环的成键位点。
当R1至R4独立地为1至10个碳原子,优选1至6个碳原子的任选取代的一价烃基,其可以被选自醚键、硫醚键、羰基键和硫代羰基键中的至少一个键隔开时,所述一价烃基的实例包括烷基,如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、新戊基、己基和辛基;环烷基,如环己基;烯基,如乙烯基、烯丙基和丙烯基;芳基,如苯基、甲苯基、二甲苯基和萘基;和芳烷基,如苄基、苯乙基和苯丙基。R1至R4中的每个基团可以具有取代基,如环氧基团、丙烯酸基团、甲基丙烯酸基团、醇(OH)基团、巯基或氨基。如上文所述,醚键、硫醚键、羰基键或硫代羰基键可以***所述基团。
R5为1至10个碳原子、特别是1至8个碳原子的任选取代的二价烃基,其实例包括亚烷基,如亚甲基、亚乙基、亚丙基、亚异丙基、亚丁基、亚异丁基、亚叔丁基、亚戊基、亚新戊基、亚己基和亚辛基;亚环烷基,如亚环己基;亚烯基,如亚乙烯基、亚烯丙基和亚丙烯基;亚芳基,如亚苯基、亚甲苯基、亚二甲苯基和亚萘基;和亚芳烷基,如亚苄基、亚苯乙基和亚苯丙基。当R5为经取代的基团时,羟基是典型的取代基。选自醚键、硫醚键、羰基键、硫代羰基键、氨基(-NR-,其中R为H、C1-C3烷基或苯基)键、氨基甲酸酯键和脲键中的至少一个键同样可以***基团R5。
R6为1至10个碳原子、优选1至6个碳原子的一价烃基,其实例包括烷基,如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、新戊基、己基和辛基;环烷基,如环己基;烯基,如乙烯基、烯丙基和丙烯基;芳基,如苯基、甲苯基、二甲苯基和萘基;和芳烷基,如苄基、苯乙基和苯丙基。在这些基团中,甲基、乙基和苯基是优选的。
R7为1至10个碳原子、优选1至6个碳原子的一价烃基,其实例包括烷基,如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、新戊基、己基和辛基;环烷基,如环己基;烯基,如乙烯基、烯丙基和丙烯基;芳基,如苯基、甲苯基、二甲苯基和萘基;和芳烷基,如苄基、苯乙基和苯丙基。在这些基团中,甲基和乙基是优选的。
具体而言,式(2)可以由下式(6)至(10)表示。
其中,m为1至8的整数,s为1至8的整数,R6、R7、n和波浪线如上文所定义,和Me为甲基。
式(3)可以由下式(11)和(12)表示。
其中,R6、R7、m、n、s和波浪线如上文所定义。
式(4)可以由下式(13)和(14)表示。
其中,R6、R7、m、n、s和波浪线如上文所定义。
式(5)可以由下式(15)表示。
其中,R6、R7、m、n和波浪线如上文所定义。
本发明的有机硅化合物可以通过多种方法制备。其中式(2)由式(6)表示、其中式(3)由式(11)表示和其中式(3)由式(13)表示的那些有机硅化合物可以通过具有儿茶酚基团和末端烯基的化合物与氢有机硅烷化合物在催化剂存在下的氢化硅烷化反应获得。
其中式(2)由式(7)表示、其中式(3)由式(12)表示和其中式(3)由式(14)表示的那些有机硅化合物可以通过具有儿茶酚基团和末端烯基的化合物与具有巯基的有机硅化合物的硫醇-烯反应获得。
其中式(2)由式(8)表示的有机硅化合物可以通过具有儿茶酚基团和脂族醇基团的化合物与具有异氰酸酯基团的有机硅化合物的反应获得。
其中式(2)由式(9)表示的有机硅化合物可以通过具有儿茶酚基团和仲氨基的化合物与具有异氰酸酯基团的有机硅化合物的反应获得。
其中式(2)由式(10)表示的有机硅化合物可以通过具有儿茶酚基团和仲氨基的化合物与具有环氧基团的有机硅化合物的反应获得。
其中式(5)由式(15)表示的有机硅化合物可以通过具有儿茶酚基团和芳族醇基团的化合物与具有异氰酸酯基团的有机硅化合物的反应获得。
另一种实施方案是包含由通式(1)表示的具有儿茶酚基团的有机硅化合物的粘合剂组合物。所述粘合剂组合物的实例包括所述有机硅化合物与无机材料的组合、所述有机硅化合物与低分子量材料的组合、所述有机硅化合物与高分子量材料的组合、和所述有机硅化合物与溶剂的组合,其可以单独或以混合物使用。所述有机硅化合物可以通过反应结合至前述材料或溶剂的任一种中。
所述粘合剂组合物中的式(1)化合物的含量没有特别限定。所述化合物的含量优选为0.001至50重量%,更优选0.1至10重量%。过低的化合物含量可能不那么有效,而过高的含量可能不经济。
优选地,在使用前将式(1)的有机硅化合物溶于溶剂中。合适的溶剂包括,但不限于烃溶剂,如戊烷、己烷、环己烷、庚烷、异辛烷、苯、甲苯和二甲苯;醚溶剂,如***、四氢呋喃和二氧六环;酯溶剂,如乙酸乙酯和乙酸丁酯;非质子极性溶剂,如乙腈和N,N-二甲基甲酰胺;质子极性溶剂,如甲醇、乙醇和水;和卤化烃溶剂,如二氯甲烷和氯仿。这些之中,质子极性溶剂是优选的,因为它们能够稳定化所述儿茶酚基团。这些溶剂可以单独或以两种或更多种的混合物使用。
对于粘合性改进和成本降低而言优选的是将式(1)的有机硅化合物以0.001至50重量%,特别是0.1至10重量%的浓度溶于所述溶剂中。
可以将酸或碱用作pH控制剂。优选地,所述组合物在pH 2至13,更优选pH 3至12。
所述粘合剂组合物可以进一步包含无机材料,例如氧化钛、氧化硅、氧化铝或氧化锆。所述无机材料的含量可以为所述组合物的0至80重量%。
所述粘合剂组合物可以进一步包含所述有机硅化合物是可溶于其中和/或其在所述溶剂中是可溶的可聚合的单体(低分子量材料)。所述低分子量材料典型地具有最多至1,000的分子量,但没有特别限定。当所述材料具有官能团时,所述官能团的实例包括可自由基聚合的基团,如羟基、羰基、羧基、氨基、硫醇基团、氰基、磺酰基、硝基、异氰酸酯基团、异硫氰酸酯基团、甲硅烷基、硫化物键(sulfide bond)、酰胺键、脲键、酯键、硅氧烷键、乙烯基和丙烯酸系基团;可阳离子聚合的基团,如环状醚和乙烯基醚;和可开环复分解聚合的基团,如降冰片烯基和二环戊二烯基。官能团的数目没有特别限制。所述低分子量材料可以单独或以两种或更多种的混合物使用。
具体而言,合适的低分子量材料为1至50个碳原子的烃并且可以包含直链、支化或环状结构或芳族基团。所述烃的一些或全部氢原子可以被取代。合适的取代基包括可自由基聚合的基团,如羟基、羰基、羧基、氨基、硫醇基团、氰基、磺酰基、硝基、异氰酸酯基团、异硫氰酸酯基团、烷基甲硅烷基、烷氧基甲硅烷基、乙烯基和丙烯酸系基团;可阳离子聚合的基团,如环状醚和乙烯基醚;和可开环复分解聚合的基团,如降冰片烯基和二环戊二烯基。所述烃可以具有一个或多个取代基。所述烃可以包含硫化物键(sulfide bond)、酰胺键、脲键、酯键或硅氧烷键。
所述低分子量材料的含量优选为最多99重量%,更优选最多50重量%,且最优选1至30重量%,基于所述粘合剂组合物计。
除所述溶剂以外,所述粘合剂组合物可以进一步包含聚合物(高分子量材料),其可溶于所述溶剂。所述高分子量材料典型地为通过凝胶渗透色谱法(GPC)相对于聚苯乙烯标样测量的重均分子量大于1,000,优选大于1,000至100,000,且更优选2,000至50,000的聚合物,但没有特别限定。当所述材料具有官能团时,所述官能团的实例包括可自由基聚合的基团,如羟基、羰基、羧基、氨基、硫醇基团、氰基、磺酰基、硝基、异氰酸酯基团、异硫氰酸酯基团、甲硅烷基、硫化物键(sulfide bond)、酰胺键、脲键、酯键、硅氧烷键、乙烯基和丙烯酸系基团;可阳离子聚合的基团,如环状醚和乙烯基醚;和可开环复分解聚合的基团,如降冰片烯基和二环戊二烯基。官能团的数目没有特别限制。还包括由这样的官能团的反应获得的高分子量材料。所述高分子量材料可以单独或以两种或更多种的混合物使用。
示例性的高分子量材料包括天然高分子量材料,如蛋白质、核酸、脂质、多糖和天然橡胶;和合成高分子量材料,如酚醛树脂、环氧树脂、蜜胺树脂、脲醛树脂、聚氨酯、聚酰亚胺、聚酰胺酰亚胺、聚乙烯、聚丙烯、聚氯乙烯、聚苯乙烯、聚乙酸乙烯酯、丙烯酸系树脂、腈类树脂、异戊二烯树脂、聚氨酯树脂、乙烯-丙烯树脂、环氧氯丙烷树脂、氯丁二烯树脂、丁二烯树脂、苯乙烯-丁二烯树脂、聚酰胺、聚缩醛、聚碳酸酯、聚苯醚、聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、环状聚烯烃、聚苯硫醚、聚四氟乙烯、聚砜、聚醚砜、和聚醚醚酮,以及共聚物和前述两种或更多种的聚合物的合金。
所述高分子量材料的含量优选为最多99重量%,更优选最多50重量%,且最优选1至30重量%,基于所述粘合剂组合物计。
只要本发明的目的不受影响,所述粘合剂组合物可以进一步包含添加剂,如表面活性剂、防腐剂、防变色剂和抗氧化剂。
待用所述粘合剂组合物处理的基材可以为:能够与可水解的甲硅烷基反应以形成键的任意无机材料,和任意有机材料如能够与儿茶酚基团相互作用的有机树脂。所述基材的形状没有特别限制。典型的无机材料包括硅、钛、锆、镁、铝、铟、锡和它们的单个或复合氧化物的无机填料;玻璃纤维产品,如玻璃纤维、玻璃布、玻璃带、玻璃毡和玻璃纸;陶瓷;和金属基材,如铁、铝、铜、银、金和镁。典型的有机材料为环氧树脂、酚醛树脂、聚酰亚胺树脂、不饱和聚酯树脂、重磅纸、木材、实木、和刨花板。所述基材并不限制于本文中列出的那些。
所述粘合剂组合物的处理方法和固化条件并没有特别限制。例如,所述基材可以通过流涂、浸涂或旋涂采用所述粘合剂组合物直接处理。或者,可以通过将所述粘合剂组合物添加至由未处理的无机填料和作为分散介质的树脂组成的基础复合物并将它们混合而进行捏合处理。典型的固化程序为加热和干燥。具体而言,将表面处理的所述基材在60至180℃,优选80至150℃加热和干燥5分钟至2小时,由此同时完成溶剂去除和在所述表面处理剂中作为活性成分的所述硅烷偶联剂与所述基材表面之间的化学反应二者。
实施例
在下文以阐释的方式而非限制的方式给出本发明的实施例。Me表示甲基。
[有机硅化合物(16)至(18)的合成]
合成例1
向配备搅拌器、回流冷凝器、滴液漏斗和温度计的2-L可分式烧瓶中装入150g(1摩尔)4-烯丙基儿茶酚和一定量(1×10-4摩尔铂原子)的铂-1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷络合物的甲苯溶液。在2小时内向内部温度保持在75-85℃的所述烧瓶中滴加122g(1摩尔)的三甲氧基硅烷。将内容物在80℃搅拌1小时,接着冷却至室温。向反应混合物中添加1,088g甲醇。将产生的含有机硅化合物(16)的溶液命名为硅烷溶液A。
合成例2
向配备搅拌器、回流冷凝器、滴液漏斗和温度计的2-L可分式烧瓶中装入150g(1摩尔)4-烯丙基儿茶酚和3.5g以V-59可获自WakoPure Chemical Industries,Ltd的2,2'-偶氮双(2-甲基丁腈)。在1小时内向内部温度保持在75-85℃的所述烧瓶中滴加196g(1摩尔)3-巯基丙基三乙氧基硅烷。将内容物在80℃搅拌1小时,接着冷却至室温。向反应混合物中添加1,384g甲醇。将产生的含有机硅化合物(17)的溶液命名为硅烷溶液B。
合成例3
向配备搅拌器、回流冷凝器、滴液漏斗和温度计的2-L可分式烧瓶中装入126g(1摩尔)邻苯三酚、0.25g二辛基氧化锡和662gMIBK。在1小时内向内部温度保持在90℃的所述烧瓶中滴加205g(1摩尔)3-异氰酸酯基丙基三乙氧基硅烷。将内容物在90℃搅拌1小时,接着冷却至室温。向反应混合物中添加662g甲醇。将产生的含有机硅化合物(18)的溶液命名为硅烷溶液C。
[玻璃纤维与环氧树脂之间的粘合性测试]
实施例1至3和比较例1和2
将上文获得的硅烷溶液A至C和3-氨基丙基三乙氧基硅烷(KBE-903,Shin-Etsu Chemical Co.,Ltd.)在水和甲醇中的1重量%溶液用作表面处理剂。将各表面处理剂施涂至直径为20μm的玻璃纤维并在100℃干燥30分钟,产生经表面处理的玻璃纤维。向所述经表面处理的玻璃纤维施加呈直径为几十至几百微米(μm)的液滴形式的由环氧树脂(JER828,Japan Epoxy Resins Co.,Ltd.)和作为固化剂的三亚乙基四胺组成的热固性组合物,使得液滴保持分开。所述液滴在80℃热固化1.5小时并在100℃后固化2小时,产生球状树脂珠。所述经表面处理的玻璃纤维与所述环氧树脂之间的剪切强度使用用于复合材料的界面性质的评价设备(HM410,Tohei Sangyo Co.,Ltd.)通过微液滴测试测量。根据方程τ=F/πDL测定每单位面积的剪切强度(τ,MPa),其中D为纤维直径(μm),L为包埋于所述球状树脂珠中的纤维部分的长度(μm),和F为将所述球状树脂珠沿纤维轴向从纤维中拉出所需的负荷(mN)。所述表面处理剂的活性成分连同剪切强度的结果示于表1中。
表1
表面处理剂的活性成分 | 剪切强度(MPa) | |
实施例1 | 硅烷溶液A | 42.1 |
实施例2 | 硅烷溶液B | 42.2 |
实施例3 | 硅烷溶液C | 43.6 |
比较例1 | KBE-903 | 40.7 |
比较例2 | 未处理的 | 33.7 |
实施例和比较例的结果证实,用所述粘合剂组合物改性的基材表面紧密地粘合至环氧树脂。
通过引用将日本专利申请第2014-061196号引入本文。
尽管已描述了一些优选的实施方案,但是根据上述教导对其可以做出许多改变和变型。因此应理解的是本发明可以不同于具体描述那样实施而不脱离所附的权利要求的范围。
Claims (10)
1.式(1)的有机硅化合物:
其中,R1至R4各自独立地选自氢;经取代或未取代的一价烃基,其可以被选自醚键、硫醚键、羰基键和硫代羰基键中的至少一个键隔开;和式(2)至(5)的有机基团;且R1至R4中的至少一个为式(2)至(5)的有机基团中的任一个:
其中,R5为经取代或未取代的二价烃基,其可以被选自醚键、硫醚键、羰基键、硫代羰基键、氨基键、氨基甲酸酯键和脲键中的至少一个键隔开,R6为1至10个碳原子的烷基或6至10个碳原子的芳基,R7为1至20个碳原子的烷基、2至10个碳原子的烯基、6至10个碳原子的芳基或1至20个碳原子的酰基,n为1至3的整数,和波浪线表示与苯环的成键位点。
2.权利要求1所述的有机硅化合物,其中,式(2)为式(6)至(10)中的任一种:
其中,m为1至8的整数,s为1至8的整数,R6、R7、n和波浪线如上文所定义,和Me为甲基。
3.权利要求1所述的有机硅化合物,其中,式(3)为式(11)或(12):
其中,m为1至8的整数,s为1至8的整数,和R6、R7、n和波浪线如上文所定义。
4.权利要求1所述的有机硅化合物,其中,式(4)为式(13)或(14):
其中,m为1至8的整数,s为1至8的整数,和R6、R7、n和波浪线如上文所定义。
5.权利要求1所述的有机硅化合物,其中,式(5)为式(15):
其中,m为1至8的整数,和R6、R7、n和波浪线如上文所定义。
6.粘合剂组合物,其包含权利要求1的有机硅化合物。
7.制品,其包括具有用权利要求6的粘合剂组合物处理的表面的基材。
8.权利要求7所述的制品,其中所述基材为选自玻璃布、玻璃带、玻璃毡和玻璃纸的玻璃纤维产品。
9.权利要求7所述的制品,其中,所述基材为无机填料。
10.权利要求7所述的制品,其中,所述基材为陶瓷或金属。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2014-061196 | 2014-03-25 | ||
JP2014061196A JP6176163B2 (ja) | 2014-03-25 | 2014-03-25 | 有機ケイ素化合物及び接着性組成物並びに物品 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104945429A true CN104945429A (zh) | 2015-09-30 |
Family
ID=52477735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510131665.0A Pending CN104945429A (zh) | 2014-03-25 | 2015-03-25 | 有机硅化合物、粘合剂组合物和制品 |
Country Status (4)
Country | Link |
---|---|
US (2) | US9303048B2 (zh) |
EP (1) | EP2924043B1 (zh) |
JP (1) | JP6176163B2 (zh) |
CN (1) | CN104945429A (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108794042A (zh) * | 2018-07-13 | 2018-11-13 | 航天材料及工艺研究所 | 一种用于多孔陶瓷的粘结剂及其制备方法和使用方法 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019511561A (ja) | 2016-01-28 | 2019-04-25 | アカテコール・インコーポレイテッドACatechol, Inc. | 光開裂性プライマー組成物および使用方法 |
CN108699090A (zh) | 2016-01-28 | 2018-10-23 | 阿卡特肖勒公司 | 表面底漆组合物和使用方法 |
WO2019198598A1 (ja) * | 2018-04-13 | 2019-10-17 | 国立研究開発法人産業技術総合研究所 | オイゲノール誘導体 |
JP7327284B2 (ja) | 2020-06-01 | 2023-08-16 | 信越化学工業株式会社 | カテコール官能性オルガノポリシロキサン、その製造方法及び粉体処理剤 |
CN112480863B (zh) * | 2020-12-04 | 2023-01-17 | 江苏晟大元通新材料科技有限公司 | 一种有机硅灌封胶的制备方法 |
US11643574B2 (en) | 2021-05-28 | 2023-05-09 | Cohesys Inc. | Adhesive devices and uses thereof |
CN117965068B (zh) * | 2024-01-17 | 2024-07-12 | 惠州市德泰士达科技有限公司 | 一种高粘结强度的防水防腐涂料的制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06345847A (ja) * | 1993-06-07 | 1994-12-20 | Shin Etsu Chem Co Ltd | エポキシ樹脂組成物及び半導体装置 |
US20020106581A1 (en) * | 1999-09-28 | 2002-08-08 | Fuji Photo Film Co., Ltd. | Positive photoresist composition |
JP2009084318A (ja) * | 2007-09-27 | 2009-04-23 | Fujifilm Corp | 親水性樹脂組成物及びそれを用いた親水性部材 |
US20110288252A1 (en) * | 2008-11-17 | 2011-11-24 | Thomas Ballweg | Dialkoxy- or dihydroxyphenyl radicals containing silanes, adhesives produced therefrom and method for producing silanes and adhesives |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61100587A (ja) * | 1984-10-22 | 1986-05-19 | Chisso Corp | 有機珪素化合物 |
JP4232276B2 (ja) * | 1999-05-26 | 2009-03-04 | Jsr株式会社 | 加水分解性シラン化合物およびその製造方法 |
JP3967047B2 (ja) * | 1999-09-28 | 2007-08-29 | 富士フイルム株式会社 | ポジ型フォトレジスト組成物 |
JP2001100418A (ja) * | 1999-09-28 | 2001-04-13 | Fuji Photo Film Co Ltd | ポジ型フォトレジスト組成物 |
JP4543577B2 (ja) * | 2001-05-22 | 2010-09-15 | 東亞合成株式会社 | 保護されたカテコール基を有する有機ケイ素化合物及びその製造方法 |
JP4156858B2 (ja) * | 2002-04-03 | 2008-09-24 | 岡本化学工業株式会社 | シランカップリング剤 |
JP4844768B2 (ja) * | 2008-11-04 | 2011-12-28 | 信越化学工業株式会社 | 反応性紫外線吸収剤及び硬化性紫外線遮蔽膜形成用塗布液、紫外線遮蔽膜並びに該紫外線遮蔽膜が形成された紫外線遮蔽機能を有する基材 |
JP5317677B2 (ja) | 2008-12-22 | 2013-10-16 | 株式会社デンソー | メッキ基板の接着方法、表面改質メッキ基板および複合成型体 |
JP5981818B2 (ja) | 2012-09-21 | 2016-08-31 | 株式会社ソフイア | 遊技システム |
-
2014
- 2014-03-25 JP JP2014061196A patent/JP6176163B2/ja active Active
-
2015
- 2015-02-20 EP EP15155933.3A patent/EP2924043B1/en active Active
- 2015-02-26 US US14/632,182 patent/US9303048B2/en not_active Expired - Fee Related
- 2015-03-25 CN CN201510131665.0A patent/CN104945429A/zh active Pending
- 2015-10-23 US US14/921,268 patent/US9464100B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06345847A (ja) * | 1993-06-07 | 1994-12-20 | Shin Etsu Chem Co Ltd | エポキシ樹脂組成物及び半導体装置 |
US20020106581A1 (en) * | 1999-09-28 | 2002-08-08 | Fuji Photo Film Co., Ltd. | Positive photoresist composition |
JP2009084318A (ja) * | 2007-09-27 | 2009-04-23 | Fujifilm Corp | 親水性樹脂組成物及びそれを用いた親水性部材 |
US20110288252A1 (en) * | 2008-11-17 | 2011-11-24 | Thomas Ballweg | Dialkoxy- or dihydroxyphenyl radicals containing silanes, adhesives produced therefrom and method for producing silanes and adhesives |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACT SERVICE: "RN:121105-19-9D", 《CA网络版-STN数据库》 * |
MAHMOOD K.等: "Electrochemical Preparation Of New Organosilicone Compounds For Functionalizing Of Mesoporous Silica", 《FUNCTIONAL MATERIALS LETTERS》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108794042A (zh) * | 2018-07-13 | 2018-11-13 | 航天材料及工艺研究所 | 一种用于多孔陶瓷的粘结剂及其制备方法和使用方法 |
CN108794042B (zh) * | 2018-07-13 | 2020-11-10 | 航天材料及工艺研究所 | 一种用于多孔陶瓷的粘结剂及其制备方法和使用方法 |
Also Published As
Publication number | Publication date |
---|---|
US20160039849A1 (en) | 2016-02-11 |
EP2924043A1 (en) | 2015-09-30 |
US20150274759A1 (en) | 2015-10-01 |
EP2924043B1 (en) | 2017-12-20 |
JP6176163B2 (ja) | 2017-08-09 |
JP2015182977A (ja) | 2015-10-22 |
US9464100B2 (en) | 2016-10-11 |
US9303048B2 (en) | 2016-04-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104945429A (zh) | 有机硅化合物、粘合剂组合物和制品 | |
US5120810A (en) | Adhesive composition | |
US8513342B2 (en) | Durable superhydrophobic coatings | |
US9562163B2 (en) | Optically clear biofouling resistant compositions and methods for marine instruments | |
CN105474018B (zh) | 微量化学芯片和反应装置 | |
CN102272232B (zh) | 聚有机硅氧烷组合物及其制造方法、该组合物的固化体、该组合物在制备粘接剂中的用途 | |
SE462800B (sv) | Foerfarande foer framstaellning av aaterreflekterande material samt enligt foerfarandet framstaellt material | |
Moon et al. | Adhesion behavior of catechol-incorporated silicone elastomer on metal surface | |
BR112014012199B1 (pt) | composição de oligômeros de siloxanos olefinicamente funcionalizados à base de alcoxissilanos, seu processo de preparação e uso | |
Bajpai et al. | Development of a high performance hybrid epoxy silicone resin for coatings | |
CN105384766A (zh) | 水性硅烷偶联剂组合物、制备方法和表面处理剂 | |
Zhang et al. | Epoxy-silicone copolymer synthesis via efficient hydrosilylation reaction catalyzed by high-activity platinum and its effect on structure and performance of silicone rubber coatings | |
Wang et al. | Silicone-epoxy block hybrid network to achieve high-performance and transparent polydimethylsiloxane materials | |
CN105940068A (zh) | 可交联有机硅组合物 | |
CN101934623B (zh) | 热压合用硅橡胶片材 | |
CN109863218A (zh) | 包含胍催化剂和增粘剂的可交联硅树脂混合物 | |
WO2018092592A1 (ja) | 有機ケイ素化合物を含む組成物並びにこれを含む塗料および接着剤 | |
CN108367548A (zh) | 层叠体及其制造方法 | |
JP5699462B2 (ja) | ピペラジニル基を有する有機ケイ素化合物を含有する接着性組成物 | |
Chiang et al. | Methacrylate silatrane: new building block for development of functional polymeric coatings through controlled silanization | |
CN107793500A (zh) | 硅烷改性的共聚物、制备方法和粘合性改进剂 | |
JP2015034097A (ja) | 水性シランカップリング剤組成物及びその製造方法、表面処理剤並びに物品 | |
Wu et al. | Promoters for improved adhesion strength between Addition-Cured liquid silicone rubber and Low-Melting-Point thermoplastic polyurethanes | |
CN115678419A (zh) | 一种季铵盐抗菌的拒水有机-无机杂化图层及合成方法 | |
Liu et al. | Bioinspired High-Performance Silicone Elastomers by Catalyst-Free Dopamine Cross-Linking |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150930 |