WO2003014248A2 - Adhesion promoting resins with cross-linking properties - Google Patents
Adhesion promoting resins with cross-linking properties Download PDFInfo
- Publication number
- WO2003014248A2 WO2003014248A2 PCT/US2002/020502 US0220502W WO03014248A2 WO 2003014248 A2 WO2003014248 A2 WO 2003014248A2 US 0220502 W US0220502 W US 0220502W WO 03014248 A2 WO03014248 A2 WO 03014248A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- reaction
- carbon
- adhesion promoting
- precursor
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 121
- 239000011347 resin Substances 0.000 title claims abstract description 121
- 230000001737 promoting effect Effects 0.000 title claims description 91
- 238000004132 cross linking Methods 0.000 title abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 50
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000007792 addition Methods 0.000 claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 9
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims abstract description 4
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 175
- 229910000077 silane Inorganic materials 0.000 claims description 32
- 239000002243 precursor Substances 0.000 claims description 28
- 239000012948 isocyanate Substances 0.000 claims description 22
- 150000002513 isocyanates Chemical class 0.000 claims description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- -1 poly(butadiene) Polymers 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 152
- 239000007858 starting material Substances 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- 229920000642 polymer Polymers 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000000853 adhesive Substances 0.000 description 23
- 230000001070 adhesive effect Effects 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 11
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 8
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 8
- 239000008393 encapsulating agent Substances 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- VJJZJBUCDWKPLC-UHFFFAOYSA-N 3-methoxyapigenin Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C=C1 VJJZJBUCDWKPLC-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 4
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 4
- 239000012704 polymeric precursor Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 3
- 230000000712 assembly Effects 0.000 description 3
- 238000000429 assembly Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 238000004377 microelectronic Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
- IUDMXOOVKMKODN-UHFFFAOYSA-N 2-(cyclohexen-1-yl)ethanamine Chemical compound NCCC1=CCCCC1 IUDMXOOVKMKODN-UHFFFAOYSA-N 0.000 description 2
- GLISOBUNKGBQCL-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(C)CCCN GLISOBUNKGBQCL-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SQGBZKZDUMBTIJ-UHFFFAOYSA-N n-prop-2-enylcyclohexanamine Chemical compound C=CCNC1CCCCC1 SQGBZKZDUMBTIJ-UHFFFAOYSA-N 0.000 description 2
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052990 silicon hydride Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- YWWSWEIXJXYQJB-AATRIKPKSA-N (e)-n,n'-diethylbut-2-ene-1,4-diamine Chemical compound CCNC\C=C\CNCC YWWSWEIXJXYQJB-AATRIKPKSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- QMOCHTLIIWRLQV-UHFFFAOYSA-N 2-[methyl(3-trimethoxysilylpropyl)amino]ethanol Chemical compound CO[Si](OC)(OC)CCCN(C)CCO QMOCHTLIIWRLQV-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PYCNXFLQHZMWJL-UHFFFAOYSA-N 3-(2-hydroxyethyl)pyrrole-2,5-dione Chemical compound OCCC1=CC(=O)NC1=O PYCNXFLQHZMWJL-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- GLISZRPOUBOZDL-UHFFFAOYSA-N 3-bromopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCBr GLISZRPOUBOZDL-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- TVTRDGVFIXILMY-UHFFFAOYSA-N 4-triethoxysilylaniline Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(N)C=C1 TVTRDGVFIXILMY-UHFFFAOYSA-N 0.000 description 1
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 description 1
- WOJKKJKETHYEAC-UHFFFAOYSA-N 6-Maleimidocaproic acid Chemical compound OC(=O)CCCCCN1C(=O)C=CC1=O WOJKKJKETHYEAC-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OEFFPHFTOMYCLS-VAWYXSNFSA-N CCC(CC)(CC1OC1CCC(C/C=C/CC(CC)(CC)OC(Nc1cc(Cc2cc(N=C=O)ccc2)ccc1)=O)C=C)OC(Nc1cccc(Cc2cc(N=C=O)ccc2)c1)=O Chemical compound CCC(CC)(CC1OC1CCC(C/C=C/CC(CC)(CC)OC(Nc1cc(Cc2cc(N=C=O)ccc2)ccc1)=O)C=C)OC(Nc1cccc(Cc2cc(N=C=O)ccc2)c1)=O OEFFPHFTOMYCLS-VAWYXSNFSA-N 0.000 description 1
- 0 CCCC#CCC(CCC1CC1)CCC=CCC(CC)(C(C)*)N Chemical compound CCCC#CCC(CCC1CC1)CCC=CCC(CC)(C(C)*)N 0.000 description 1
- XEQNRQBTAKVTJE-UHFFFAOYSA-N CCCNC(NC)=O Chemical compound CCCNC(NC)=O XEQNRQBTAKVTJE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KEJFAGMNOBNFJR-QMTHXVAHSA-N Isophorene Natural products S=C(NC[C@]1(C)C[C@H](NC(=S)NC)CC(C)(C)C1)NC KEJFAGMNOBNFJR-QMTHXVAHSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- GSXJAPJSIVGONK-UHFFFAOYSA-N chloro-ethenyl-methyl-phenylsilane Chemical compound C=C[Si](Cl)(C)C1=CC=CC=C1 GSXJAPJSIVGONK-UHFFFAOYSA-N 0.000 description 1
- AWSNMQUTBVZKHY-UHFFFAOYSA-N chloro-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)Cl AWSNMQUTBVZKHY-UHFFFAOYSA-N 0.000 description 1
- NNKJLYMBVRDUEI-UHFFFAOYSA-N chloro-tris(ethenyl)silane Chemical compound C=C[Si](Cl)(C=C)C=C NNKJLYMBVRDUEI-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical class [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- FZQNBVBLHJXOEA-UHFFFAOYSA-N diethoxy(propyl)silane Chemical compound CCC[SiH](OCC)OCC FZQNBVBLHJXOEA-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CBRIQVFXGOWUJI-UHFFFAOYSA-N ethoxy(ethyl)silicon Chemical compound CCO[Si]CC CBRIQVFXGOWUJI-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 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
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- SPIGUVVOJXSWNX-UHFFFAOYSA-N n-(oxomethylidene)thiohydroxylamine Chemical compound SN=C=O SPIGUVVOJXSWNX-UHFFFAOYSA-N 0.000 description 1
- AXTLFVLHXSDZOW-UHFFFAOYSA-N n-ethyl-2-methylprop-2-en-1-amine Chemical compound CCNCC(C)=C AXTLFVLHXSDZOW-UHFFFAOYSA-N 0.000 description 1
- IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
- CTSIKBGUCQWRIM-UHFFFAOYSA-N n-prop-2-enylcyclopentanamine Chemical compound C=CCNC1CCCC1 CTSIKBGUCQWRIM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 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
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- SLIOYUPLNYLSSR-UHFFFAOYSA-J tetrachloroplatinum;hydrate;dihydrochloride Chemical compound O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl SLIOYUPLNYLSSR-UHFFFAOYSA-J 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
Classifications
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/702—Isocyanates or isothiocyanates containing compounds having carbon-to-carbon double bonds; Telomers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
Definitions
- This invention relates to resins containing silane and cross- linking functionalities.
- Adhesive compositions are used in many industries, such as the microelectronics industry, where good adhesion to metal and organic substrates and low viscosity for easy dispensability are important requisites.
- adhesion promoting resins with sufficient molecular weight to give lower volatility than the silanes currently commercially available.
- the adhesion promoting resins disclosed in this specification are curable compositions that are suitable for use as adhesives, encapsulants, or sealants, particularly for applications within the microelectronic industry.
- This invention is an adhesion promoting resin that comprises an oligomeric or polymeric segment and a silane segment.
- the silane segment will be present at the terminus of an oligomeric segment, or at a terminus or the termini of a polymeric segment, or at the terminus or termini and pendant from a polymeric segment.
- the adhesion promoting resin has cross-linking capability.
- the adhesion promoting resin has electron donor or electron acceptor functionality.
- the adhesion promoting resin is combined with a conductive or nonconductive filler, and optionally, an initiator, to provide a curable composition, which can be used, for example, as an adhesive, coating, encapsulant or sealant.
- the oligomeric or polymeric segment of the inventive adhesion promoting resin will contain at least one carbon to carbon double bond, and can be provided by a precursor resin or compound that is commercially available. Alternatively, the precursor resin or compound can be synthesized by the practitioner.
- Suitable oligomeric segment precursors are linear or branched hydrocarbons having 1 to 50 carbon atoms, which contain a reactive functionality for ultimate reaction with a co-reactive functionality on the silane segment precursor.
- Exemplary precursors include N- methylallylamine, N-ethyl-2-methylallyl-amine, diallylamine, N,N'-diethyl-2- butene-1,4-diamine, N-allylcyclopentyl-amine, allylcyclohexylamine, 2-(1- cyclohexenyl)ethylamine, and other compounds such as the alcohols containing unsaturation disclosed later in the Examples in this specification..
- Exemplary suitable polymeric segments are homopolymers of 1,3-butadiene, copolymers of ethylene and propylene, or copolymers of ethylene, propylene and a diene.
- Poly(butadienes) are commercially available, and can contain hydroxyl-, amino-, halo-, isocyanate- and epoxy- functionality.
- the unsaturated oligomeric or polymeric segment may be any molecular weight and structure desired by the practitioner, provided it has at least one carbon to carbon double bond for subsequent cross-linking.
- the oligomeric or polymeric segment may contain heteroatoms, such as, silicon, sulfur, nitrogen, or oxygen; may contain functional groups, such as hydroxyl, urea, carbamate, or ester, (although it is not limited to these functionalities); may contain cyclic or aromatic moieties.
- the at least one carbon to carbon double bond can be located within the oligomeric or polymeric backbone or chain, or pendant from the chain.
- silane segment will have the structure
- n is simultaneously for each position 0, 1, or 2;
- R 1 is a methyl or ethyl group;
- R 2 is a vinyl group, an aromatic group, or a linear or branched alkyl group, preferably of 1 to 4 carbon atoms, and more preferably methyl or ethyl;
- A is a linear or branched alkyl group or a cyclic or aromatic group, and
- L is a linking group resulting from the reaction of a functional group on the silane precursor, and a functional group on the oligomeric or polymeric precursor.
- Examples of commercially available silanes suitable as precursors for the silane segment are gamma-isocyanatopropyltriethoxy- silane, gamma-aminopropyltriethoxy-silane, gamma-aminopropyltrimethoxy- silane, N-beta-(aminoethyl)-ga/7)ma-aminopropyltrimethoxysilane, triamino- functional silane, b/s-(gam/r/a-trimethoxysilylpropyl)amine, N-phenyl-gamma- amino-propyltrimethoxysilane, N-befa-(aminoethyl)-garwr/a-aminopropyl- methyldimethoxysilane, gamma-mercaptopropyl-trimethoxysilane.
- 3-amino- propyldimethylethoxysilane 3-bromopropyltrimethoxysilane, 3-chloro- propylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, dimethylmethoxy-chlorosilane, methyldimethoxysilane, and methyldiethoxysilane.
- the inventive adhesion promoting resin is synthesized through a reaction between the precursor (also, hereinafer, starting material) for the unsaturated segment and the precursor for the silane segment.
- the precursor also, hereinafer, starting material
- suitable synthetic routes are through condensation or addition reactions between co-reactive functionalities on the precursors, or through hydrosilation. Examples of these reactions are illustrated later in this specification.
- the polymeric or oligomeric segment will be connected to the silane segment through a linking group that results from a reaction between the polymeric or oligomeric precursor and the silane precursor.
- the silane segment will be located at the termini of the oligomeric or polymeric segment -and the at least one carbon to carbon double bond will be located within the oligomeric or polymeric chain or pendant from the chain.
- the adhesion promoting resin will have the structure:
- Q is an oligomeric or polymeric group containing at least one carbon to carbon double bond, derived from an oligomeric or polymeric precursor containing carbon to carbon unsaturation; n is simultaneously for each position 0, 1 , or 2; R 1 is a methyl or ethyl group; R 2 is a vinyl group, an aromatic group, or a linear or branched alkyl group; A is a hydrocarbyl group, for example, a linear or branched alkyl group or a cyclic alkyl or alkenyl group, or aromatic group; L is a linking group resulting from the reaction of a functional group on the precursor for the segment containing silane and a functional group on the precursor for the segment containing the at least one carbon to carbon double bond.
- the silane segment will be located at the termini of a polymeric chain and pendant from the polymeric chain.
- the polymeric segment will contain at least one carbon to carbon double bond located within the polymeric chain.
- the degree of substitution of silane onto pendant functionality can be controlled by reaction stoichiometry as desired by the practitioner.
- the adhesion promoting resin will have the structure:
- the silane segment will be located pendant from a polymeric chain, and the polymeric segment will contain electron donor or electron acceptor groups at its termini.
- the adhesion promoting resin will have the structure:
- Exemplary electron donor groups are vinyl ethers, compounds containing carbon to carbon double bonds attached to an aromatic ring and conjugated with the unsaturation in the aromatic ring, such as compounds derived from cinnamyl and styrenic starting compounds.
- Exemplary electron acceptor groups are fumarates, maleates, acrylates, and maleimides.
- the silane segment will be located at the termini of a polymeric chain, and an organic moiety containing a reactive functionality capable of polymerization or capable of an addition, condensation, hydrosilation or ring opening reaction will be pendant from the polymeric chain.
- the organic moiety will contain an electron donor, an electron acceptor, an epoxy, a silicon hydride, or a polar group, such as, hydroxyl, halide, amine, isocyanate, carboxylic acid, acid chloride, vinyl, or mercapto group.
- the adhesion promoting resin will have the structure:
- RF is a reactive functionality capable of polymerization or capable of an addition, condensation, hydrosilation or ring opening reaction.
- the functional groups on the oligomeric or polymeric precursors through which the silane is to be linked include hydroxyl, halide, amine, isocyanate, carboxylic acid, acid chloride, and vinyl double bonds.
- the functional groups on the silane precursor, for reaction with the functional groups on the oligomeric or polymeric precursor include hydroxyl, amine, mercapto, isocyanate, halide, and a hydrosilation reactive hydrogen on a silicon atom. Consequently, it will be understood that the linking group can be a direct bond or an alkyl group, or can have a structure, such as
- the adhesive promoting resins herein may be used as the sole curable resin in an adhesive, coating, sealant or encapsulant formulation.
- the inventive resin can be designed to contain electron donor or electron acceptor functionality, or both, or epoxy functionality.
- the formulations will contain the adhesive promoting resin, optionally a curing initiator, and optionally a conductive or nonconductive filler.
- the adhesive promoting resins herein can be used as an additive to promote adhesion in adhesive, encapsulant, coating, and sealant formulations.
- the amount used in the formulation will be an effective amount to cause adhesion promotion.
- an adhesion promoting amount will range from 0.005 to 20.0 percent by weight of the adhesive, coating, encapsulant or sealant formulation.
- such formulations will contain a curable resin, optionally, a curing initiator, and optionally a conductive or nonconductive filler.
- Suitable curable resins that may be used in the adhesive, coating, encapsulant or sealant formulations are known to practitioners in the those arts.
- examples of such resins include epoxies, electron donor resins (for example, vinyl ethers, and resins that contain carbon to carbon double bonds attached to an aromatic ring and conjugated with the unsaturation in the aromatic ring, such as compounds derived from cinnamyl and styrenic starting compounds), and, electron acceptor resins (for example, fumarates, maleates, acrylates, and maleimides).
- Suitable curing agents are thermal initiators and photoinitiators present in an effective amount to cure the adhesive, coating, encapsulant or sealant formulation. In general, those amounts will range from 0.5% to 30%, preferably 1% to 20%, by weight of the total organic material (that is, excluding any inorganic fillers) in the formulation.
- Preferred thermal initiators include peroxides, such as butyl peroctoates and dicumyl peroxide, and azo compounds, such as 2,2'-azobis(2-methyl-propanenitrile) and 2,2'-azobis(2-methyl-butanenitrile).
- a preferred series of photoinitiators is one sold under the trademark Irgacure by Ciba Specialty Chemicals.
- both thermal initiation and photoinitiation may be desirable: the curing process can be started either by irradiation, followed by heat, or can be started by heat, followed by irradiation.
- the formulations will cure within a temperature range of 70 C C to 250°C, and curing will be effected within a range of ten seconds to three hours. The actual cure profile will vary with the components and can be determined without undue experimentation by the practitioner.
- the formulations may also comprise conductive or nonconductive fillers. Suitable conductive fillers are carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina.
- Suitable nonconductive fillers are particles of vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, and halogenated ethylene polymers, such as tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride. If present, fillers generally will be in amounts of 20% to 90% by weight of the formulation.
- reaction stoichiometry for the syntheses of starting materials and inventive resins is given in molar equivalents per molecule of reactant. It will be understood by those skilled in the art that some of the reactants have more than one functionality per molecule, and that the ratio of molar equivalent per functionality can be varied to give a predetermined degree of reactivity or substitution. For convenience, the depicted structures show full substitution along the polymeric chain, but it should be understood that the level of substitution will depend in practice on the ratio of molar equivalents of functionality that are reacted.
- the level of hydroxyl functionality added to poly(butadiene) through the reaction of mercaptoethanol with the pendant vinyl functionality can be varied by the molar amounts of mercaptoethanol reacted, and can range from one molar equivalent to full substitution of the 20% of the pendant vinyl groups along the poly(butadiene) polymer chain.
- the level of silane functionality added to an adhesion promoting resin can be varied by adjusting the mole equivalents of functionalities to be reacted.
- PROCEDURE 1 Reaction of mercaptoethanol with pendant vinyl functionality on poly(butadiene) (PBD). The synthetic procedure is conducted according Boutevin, G., Ameduri, B., Boutevin, B., Joubert, J-P., Journal of Applied Polymer Science, 75, 1655-1666, 2000, in a ratio of 1:1 mole equivalent of mercapto functionality to vinyl functionality, at the level of substitution of desired.
- PROCEDURE Reaction of isocyanate with alcohol.
- PROCEDURE 3 Reaction of gamma-mercaptopropyl- trimethoxysilane SM-11 with pendant vinyl functionality on poly(butadiene).
- the synthetic procedure is conducted according to Schapman, F., Couvercelle, J.P., and Bunel, C, Polymer, 1998, Vol. 39, No. 20, in a ratio of 1:1 mole equivalent of gamma-mercaptopropyltrimethoxysilane to vinyl functionality, at the level of substitution desired.
- the level of silane functionality added can be varied by the molar amounts of mercaptosilane reacted and can range from one molar equivalent to full substitution of the 20%) of the pendant vinyl groups along the poly(butadiene) polymer chain.
- PROCEDURE 4 Reaction of isocyanate with amine.
- PROCEDURE 6 Reaction of alkyl halide with alcohol.
- PROCEDURE 7 Conversion of alcohol functionality to chloride functionality.
- the synthetic procedure is conducted according to E. W. Collington and A. I. Meyers, J. Org. Chem. 36, 3044 (1971).
- a stirred mixture of one mole equivalent of alcohol and 1.1 mole equivalent of s- collidine under nitrogen is treated with one mole equivalent of lithium chloride dissolved in a minimum amount of dry dimethylformamide.
- On cooling to 0°C a suspension is formed which is treated dropwise with 1.1 mole equivalent of methanesulfonyl chloride. Stirring is continued at 0°C for 1-1.5 hour, when the pale yellow reaction mixture is poured over ice-water.
- the aqueous layer is extracted with cold ether-pentane (1:1) and the combined extracts are washed successively with saturated copper nitrate solution. This is continued until no further intensification of the blue copper solution occurs, indicating complete removal of s-collidine.
- the organic extracts are dried (Na 2 S0 4 ) and concentrated at room temperature, providing a residue of the product.
- PROCEDURE 8 Reaction of amine with acid chloride.
- PROCEDURE 9 Reaction of alcohol with acid chloride. One mole equivalent of alcohol and triethylamine are mixed in dry methylene chloride at 0°C. One mole equivalent acid chloride dissolved in dry methylene chloride is carefully added. The mixture is allowed to react for four hours. The solvent is evaporated and the crude product is purified by column chromatography using a gradient of hexane / ethyl acetate to give the product.
- PROCEDURE 10 Reaction of alcohol with carboxylic acid. Into a four necked flask is charged one mole equivalent of carboxylic acid solvated in toluene, to which is added one mole equivalent of alcohol, and a catalytic amount of sulfuric acid. The flask is fitted with a Dean Stark apparatus, mercury thermometer, mechanical stirrer, and the organic solution covered with nitrogen. The reaction mixture is raised to reflux (110°C. Reflux is maintained for approximately 4 hours or until theoretical water is obtained in the Dean Stark trap. The condensate trap is emptied to remove the collected water, and allowed to refill with fresh distillate. An equal amount of virgin solvent is charged to the flask to maintain a consistent solvent level.
- the trap is again emptied and allowed to refill; again back charging fresh solvent to replace the distillate that is removed. This process is repeated four more times in an effort to drive maximum water removal from the system.
- the oil bath is removed and the reaction shut down. The solvent is evaporated and the crude product is purified by column chromatography using a gradient of hexane / ethyl acetate to give the product.
- PROCEDURE 11 Reaction of alcohol with vinyl silane.
- PROCEDURE 12 Reaction of isocyanate with mercaptan. One mole equivalent of isocyanate is solvated in toluene in a three-necked flask equipped with a mechanical stirrer, addition funnel and nitrogen inlet/outlet. The reaction is placed under nitrogen and the solution heated to 60°C. The addition funnel is charged with one mole equivalent of mercaptan in toluene. This solution is then added to the isocyanate solution over 10 minutes, and the resulting mixture is heated for an additional 3 hours at 60°C. After the reaction is allowed to cool to room temperature, the solvent is removed in vacuo to give the product. [0041] PROCEDURE 13: Reaction of isothiocyanate with alcohol.
- PROCEDURE 14 Hydrosilation. A solution of one mole equivalent of alkene and toluene is prepared with stirring, to which is added a catalytic amount of hydrogen hexachloroplatinate (IV) hydrate (H 2 PtCI 6 , available from Aldrich). The resulting solution is heated to 80°C and one mole equivalent of silicon hydride is added gradually via a syringe. The resulting mixture is heated for an additional hour at 80°C. After the reaction is allowed to cool to room temperature, the solvent is removed in vacuo to give the product.
- IV hydrogen hexachloroplatinate
- PROCEDURE 15 Reaction of carboxylic acid with isocyanate. The synthetic procedure is conducted according to T. Nishikubo, E. Takehara, and A. Kameyama, Polymer Journal, 25, 421 (1993). A stirred mixture of one mole equivalent of isocyanate and one mole equivalent of carboxylic acid is solvated in toluene in a three-necked flask equipped with a mechanical stirrer and nitrogen inlet/outlet. The mixture is heated for two hours at 80°C. After the reaction is allowed to cool to room temperature, the solvent is removed in vacuo to give the product. [0044] PROCEDURE 16: Reaction of disiloxane with vinyl epoxy.
- a round-bottomed flask is charged with one mole equivalent of disiloxane and one mole equivalent of vinyl epoxy resin.
- the reaction flask is equipped with a magnetic stirrer and a reflux condenser.
- a catalytic amount of tris(triphenylphosphine)rhodium(l) chloride is added to this mixture.
- the reaction is followed using gas chromatography by monitoring the disappearance of the starting materials and the appearance of the products. After the completion of the reaction, pure product is obtained by fractional vacuum distillation.
- PROCEDURE 17 Synthesis of epoxy functional poly(butadiene).
- One mole equivalent of PBD is dissolved in toluene and placed in a two-necked round bottomed flask.
- One mole equivalent of epoxy siloxane adduct is added to the flask, and the reaction mixture is heated to 60°C.
- One drop of Karstedt's catalyst is added , and the hydrosilation reaction is obtained and monitored by following the disappearance of Si-H band at 2117 cm '1 in the infrared spectrum. The reaction is completed in approximately two to three hours.
- the reaction mixture is poured with stirring into methanol to precipitate the grafted PBD polymer.
- the precipitated PBD is washed with methanol and dried in vacuo at 60°C for eight hours.
- SM-1 N-befa-(aminoethyl)-gamma-aminopropyltrimethoxy- silane, available from Witco Corporation.
- SM-2 N-befa-(aminoethyl)-gamma-aminopropyltriethoxy- silane, available from Witco Corporation.
- SM-3 p-Aminophenyltrimethoxysilane, available from
- SM-4 p-Aminophenyltriethoxysilane, available from Wright
- SM-5 3-Aminopropyldimethylethoxysilane, available from
- SM-6 Gamma-aminopropyltriethoxysilane, available from
- SM-7 Bis(2-hydroxyethyl)-3-aminoproplytriethoxysilane, available from Gelest, Inc.
- SM-8 N-(hydroxyethyl)-N-methylaminopropyltrimethoxy- silane, available from Gelest, Inc.
- SM-9 Gamma-isocyanatopropyltriethoxysilane, commercially available from Witco Corp. as Silquest A-1310.
- SM-10 Gamma-isocyanatopropyltrimethoxysilane, available from Wright Corporation.
- SM-11 Gamma-mercaptopropyltrimethoxysilane, commercially available from Witco Corp. as product Silquest A-189.
- SM-12 Tri ethoxysilane, available from Gelest, Inc.
- SM-13 Triethoxysilane, available from Wright Corporation.
- SM-14 Propyldiethoxysilane, available from Wright
- SM-15 Di ethylethoxysilane, available from Gelest, Inc.
- SM-16 PBD, commercially available from Elf Atochem as
- SM-17 PBD, commercially available from Elf Atochem as
- SM-18 Epoxidized PBD, commercially available from Elf
- Atochem as product Poly bd 600 Atochem as product Poly bd 600. According to the manufacturer's literature the predominant microstructure is
- cis vinyl trans in which the cis unsaturation constitutes 20% of the unsaturation in the polymer chain, the trans unsaturation constitutes 20% of the unsaturation in the polymer chain, and the vinyl unsaturation constitutes 60% of the unsaturation in the polymer chain, and in which n is a mixture of 14 and 15 (some of the polymer chains will be the length in which n is 14, and the remainder of the polymer chains will be the length in which n is 15).
- the predominant microstructure is the same as that disclosed for SM-18, with the exception that n is a mixture of 13 and 14 (some of the polymer chains will be the length in which n is 13, and the remainder of the polymer chains will be the length in which n is 14).
- SM-20 Starting material prepared according to synthetic procedure 1 by the reaction of mercaptoethanol and SM-16.
- SM-21 Starting material prepared according to synthetic procedure 1 by the reaction of mercaptoethanol and SM-17.
- SM-22 Starting material prepared according to synthetic procedure 1 by the reaction of mercaptoethanol and SM-18.
- SM-23 Starting material prepared according to synthetic procedure 1 by the reaction of mercaptoethanol and SM-19.
- SM-24 Starting material prepared according to synthetic procedure 2 by the reaction of 4,4'-methylene di(phenylisocyanate) (MDI) with SM-16.
- SM-25 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-17.
- SM-26 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-18.
- SM-27 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-19.
- SM-28 Starting material prepared according to synthetic procedure 3 by the reaction of SM-11 with SM-16.
- SM-29 Starting material prepared according to synthetic procedure 3 by the reaction of gamma-mercaptopropyltrimethoxysilane SM- 11 with SM-17.
- SM-30 Starting material prepared according to synthetic procedure 3 by the reaction of SM-11 with SM-18.
- SM-31 Starting material prepared according to synthetic procedure 3 by the reaction of gamma-mercaptopropyltrimethoxysilane SM- 11 with SM-19.
- SM-32 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-28. This material is also an inventive example.
- SM-33 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-29. This material is also an inventive example.
- SM-34 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-30. This material is also an inventive example.
- SM-35 Starting material prepared according to synthetic procedure 2 by the reaction of MDI with SM-31. This material is also an inventive example.
- SM-36 Starting material prepared according to synthetic procedure 6 by the reaction of allyl bromide with SM-16.
- SM-37 Starting material prepared according to synthetic procedure 6 by the reaction of allyl bromide with SM-17.
- SM-38 Starting material prepared according to synthetic procedure 6 by the reaction of allyl bromide with SM-18.
- SM-39 Starting material prepared according to synthetic procedure 6 by the reaction of allyl bromide with SM-19.
- SM-40 Starting material prepared according to synthetic procedure 2 by the reaction of allyl isocyanate with SM-16.
- SM-41 Starting material prepared according to synthetic procedure 2 by the reaction of allyl isocyanate with SM-17.
- SM-42 Starting material prepared according to synthetic procedure 2 by the reaction of allyl isocyanate with SM-18.
- SM-43 Starting material prepared according to synthetic procedure 2 by the reaction of allyl isocyanate with SM-19.
- SM-44 Starting material prepared according to synthetic procedure 2 by the reaction of octanyl isocyanate with SM-16.
- SM-45 Starting material prepared according to synthetic procedure 2 by the reaction of octanyl isocyanate with SM-17.
- SM-46 Starting material prepared according to synthetic procedure 2 by the reaction of octanyl isocyanate with SM-18.
- SM-47 Starting material prepared according to synthetic procedure 2 by the reaction of octanyl isocyanate with SM-19.
- SM-48 Starting material prepared according to synthetic procedure 7 by the reaction of SM-16 with methyl sulfonyl chloride and lithium chloride.
- SM-49 Starting material prepared according to synthetic procedure 7 by the reaction of SM-17 with methyl sulfonyl chloride and lithium chloride.
- SM-50 Starting material prepared according to synthetic procedure 7 by the reaction of SM- 8 with methyl sulfonyl chloride and lithium chloride.
- SM-51 Starting material prepared according to synthetic procedure 7 by the reaction of SM-19 with methyl sulfonyl chloride and lithium chloride.
- SM-52 Starting material prepared according to synthetic procedure 5 by the reaction of SM-48 with NH 3 .
- SM-53 Starting material prepared according to synthetic procedure 5 by the reaction of SM-49 with NH 3 .
- SM-54 Starting material prepared according to synthetic procedure 5 by the reaction of SM-50 with NH 3 .
- SM-55 Starting material prepared according to synthetic procedure 5 by the reaction of SM-51 with NH 3 .
- SM-56 Starting material prepared according to synthetic procedure 4 by the reaction of SM-52 with allyl isocyanate.
- SM-57 Starting material prepared according to synthetic procedure 4 by the reaction of SM-53 with allyl isocyanate.
- SM-58 Starting material prepared according to synthetic procedure 4 by the reaction of SM-54 with allyl isocyanate.
- SM-59 Starting material prepared according to synthetic procedure 4 by the reaction of SM-55 with allyl isocyanate.
- SM-60 Starting material prepared according to synthetic procedure 4 by the reaction of SM-52 with octanyl isocyanate.
- SM-61 Starting material prepared according to synthetic procedure 4 by the reaction of SM-53 with octanyl isocyanate.
- SM-62 Starting material prepared according to synthetic procedure 4 by the reaction of SM-54 with octanyl isocyanate.
- SM-63 Starting material prepared according to synthetic procedure 4 by the reaction of SM-55 with octanyl isocyanate.
- SM-64 Starting material prepared according to synthetic procedure 8 by the reaction of SM-52 with butanoyl chloride.
- SM-65 Starting material prepared according to synthetic procedure 8 by the reaction of SM-53 with butanoyl chloride.
- SM-66 Starting material prepared according to synthetic procedure 8 by the reaction of SM-54 with butanoyl chloride.
- SM-67 Starting material prepared according to synthetic procedure 8 by the reaction of SM-55 with butanoyl chloride.
- SM-68 Starting material prepared according to synthetic procedure 9 by the reaction of 2-isobutenoyl chloride with SM-16.
- SM-69 Starting material prepared according to synthetic procedure 9 by the reaction of 2-isobutenoyl chloride with SM-17.
- SM-70 Starting material prepared according to synthetic procedure 9 by the reaction of 2-isobutenoyl chloride with SM-18.
- SM-71 Starting material prepared according to synthetic procedure 9 by the reaction of 2-isobutenoyl chloride with SM-19.
- SM-72 1,3-Divinyltetramethyldisilazane, available from
- SM-73 Starting material prepared according to synthetic procedure 5 by the reaction of 4-vinyl benzyl chloride with SM-53.
- SM-74 Starting material prepared according to synthetic procedure 5 by the reaction of 4-vinyl benzyl chloride with SM-52.
- SM-75 Starting material prepared according to synthetic procedure 5 by the reaction of 4-vinyl benzyl chloride with SM-54.
- SM-76 Starting material prepared according to synthetic procedure 5 by the reaction of 4-vinyl benzyl chloride with SM-55.
- SM-77 Fumaric acid ethyl ester.
- SM-78 Starting material prepared according to synthetic procedure 10 by the reaction of trimethylolpropane diallyl ether and mercaptoacetic acid.
- SM-79 Starting material prepared according to synthetic procedure 2 by the reaction of trimethylolpropane diallyl ether and isophorene diisocyanate.
- Examples 1 to 7 show adhesion-promoting resins with a polymeric chain of poly(butadiene) (hereinafter "PBD"), and silane segments located at the termini of the polymeric chain.
- PBD poly(butadiene)
- EXAMPLE 1 Adhesion-promoting resin prepared according to synthetic procedure 2 by the reaction of PBD SM-16 and SM-9.
- EXAMPLE 5 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of SM-26 and SM-3.
- EXAMPLE 6 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of SM-24 and SM-2.
- EXAMPLE 7 Adhesion promoting resin prepared according to synthetic procedure 12 by the reaction of SM-25 with SM-11.
- Examples 8 to 16 show adhesion-promoting resins having silane functionality at the termini of, and pendant from, the polymeric segment.
- EXAMPLE 8 Adhesion promoting resin prepared by the reaction of SM-9 and SM-20 according to synthetic procedure 2.
- EXAMPLE 9 Adhesion promoting resin prepared from the reaction of SM-10 and SM-23 according to synthetic procedure 2.
- EXAMPLE 10 Adhesion promoting resin prepared from the reaction of SM-34 with SM-4 according to synthetic procedure 4.
- EXAMPLE 11 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of SM-32 and SM-4.
- EXAMPLE 12 Adhesion promoting resin prepared according to synthetic procedure 12 by the reaction of SM-34 with SM-11.
- EXAMPLE 13 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-59 and SM-13.
- EXAMPLE 14 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-41 and SM-13.
- EXAMPLE 15 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-36 and SM-13.
- EXAMPLE 16 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-38 and SM-12.
- Examples 17 to 36 show oligomeric adhesion-promoting resins in which the Tg is greater than 0°C.
- EXAMPLE 17 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (£)-2,6,10-trimethyl-5, 9-undecadien-2-ol (Nakamura, S.; Ishihara, K.; Yamamoto, H.; J. Am. Chem. Soc. 2000, 22, 8131) with SM-9.
- EXAMPLE 18 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (E)-homogeraniol (Nakamura, S.; Ishihara, K.; Yamamoto, H.; J. Am. Chem. Soc. 2000, 122, 8131) with SM-10.
- EXAMPLE 19 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (E,£)-4,8,12-trimethyl- 3,7,11-tridecadien-1-ol (Nakamura, S.; Ishihara, K.; Yamamoto, H.; J. Am. Chem. Soc. 2000, 722, 8131) with SM-9.
- EXAMPLE 20 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (-)-c/s-carveol (Buchi, G.; Cushman, M.; Wuest, H.; J. Am. Chem. Soc. 1974, 96, 5563) with SM-10.
- EXAMPLE 21 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of 3-methyl-5-(2',6' 1 6'- trimethylcyclohex-1'-enyl)-1-penten-3-ol (Barrero, A. F.; Altarejos, J.; Alvarez- Manzaneda, E. J.; Ramos, J. M.; Salido, S.; J. Org. Chem. 1996, 61, 2215) with SM-9.
- EXAMPLE 22 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (£)-4-methyl-6-(2',6',6'- trimethyl-cyclohex-1'-enyl)-3-hexen-1-ol (Barrero, A. F.; Altarejos, J.; Alvarez- Manzaneda, E. J.; Ramos, J. M.; Salido, S.; J. Org. Chem. 1996, 67, 2215) with SM-9.
- EXAMPLE 23 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (Z)-4-methyl-6-(2',6',6'- trimethylcyclohex-1'-enyl)-3-hexen-1-ol (Barrero, A. F.; Altarejos, J.; Alvarez- Manzaneda, E. J.; Ramos, J. M.; Salido, S.; J. Org. Chem. 1996, 67, 2215) with SM-10.
- EXAMPLE 24 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (all-Z)-icosa- 2,5,8,11 ,14,17-hexanenol (Flock, S.; Skattebol, L; J. Chem. Soc, Perkin Trans. 1, 2000, 3071) with SM-10.
- EXAMPLE 25 Adhesion promoting resin prepared according to synthetic procedure 2 by the reaction of (3E,7E,11E)-4,8, 12,16- tetramethyl-heptadeca-3,7,11 ,15-tetraen-1-ol (Kocienski, P.; Wadman, S.; J. Org. Chem. 1989, 54, 1215) with SM-9.
- EXAMPLE 26 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of ⁇ /,W-diethyl-2-butene- 1 ,4-diamine with SM-9.
- EXAMPLE 27 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of diallyl amine with SM-9.
- EXAMPLE 28 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of allylcyclohexylamine with SM-9.
- EXAMPLE 29 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of 2-(1-cyclohexenyl) ethylamine with SM-9.
- EXAMPLE 30 Adhesion promoting resin prepared according to synthetic procedure 4 by the reaction of SM-79 and SM-6.
- EXAMPLE 31 Adhesion promoting resin prepared according to synthetic procedure 6 by the reaction of (E)-homogeraniol and allyl bromide, followed by synthetic procedure 14, reaction with SM-12.
- EXAMPLE 32 Adhesion promoting resin prepared according to synthetic procedure 6. by the reaction of (Z)-4-methyl-6-(2',6',6'- trimethylcyclohex-1'-enyl)-3-hexen-1-ol with allyl bromide, followed by synthetic procedure 14, reaction with SM-14.
- EXAMPLE 33 Adhesion promoting resin prepared according to synthetic procedure 12 by the reaction of SM-78 with SM-9.
- EXAMPLE 34 Adhesion promoting resin prepared according to synthetic procedure 12 by the reaction of SM-79 and SM-11.
- EXAMPLE 35 Adhesion promoting resin prepared according to synthetic procedure 13 by the reaction of allylisothiocyanate and SM-6.
- EXAMPLE 36 Adhesion promoting resin prepared according to synthetic procedure 13 by the reaction of allylisothiocyanate and SM-7.
- Examples 37 to 53 show adhesion promoting resins in which the unsaturated polymeric segment is terminated with an electron donor or electron acceptor functionality, and the silane segment is pendant from the polymeric segment.
- EXAMPLE 37 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 2 by the reaction of SM-32 with cinnamyl alcohol.
- EXAMPLE 38 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 4 by the reaction of SM-34 and 3-isopropenyl- ⁇ , ⁇ - methylbenzyl amine.
- EXAMPLE 39 Adhesion promoting resin containing electron acceptor functionality prepared according to synthetic procedure 14 by the reaction of SM-26 and SM-13, followed by synthetic procedure 2, reaction with hydroxyethyl maleimide.
- EXAMPLE 40 Adhesion promoting resin containing electron acceptor functionality prepared according to synthetic procedure 14 by the reaction of SM-25 and SM-13, followed by synthetic procedure 2, reaction with hydroxyethyl acrylate.
- EXAMPLE 41 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 14 by the reaction of SM-24 and SM-13, followed by synthetic procedure 2, reaction with propylamine vinyl ether.
- EXAMPLE 42 Adhesion promoting resin containing electron acceptor functionality prepared according to synthetic procedure 15 by the reaction of SM-32 and fu marie acid SM-77.
- Example 43 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 2 by the reaction of SM-28 and 3-isopropenyl- ⁇ , ⁇ -methylbenzyl isocyanate.
- Example 44 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 6 by the reaction of SM-16 and cinnamyl chloride, followed by synthetic procedure 14, reaction with SM-13.
- EXAMPLE 45 Adhesion promoting resin containing electron acceptor functionality prepared according to synthetic procedure 10 by the reaction of SM-28 and SM-77.
- Example 46 Adhesion promoting resin containing electron acceptor functionality prepared according to procedure 9 by the reaction of SM-28 and 2-isobutanoylchloride.
- Example 47 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 3 by the reaction of SM-53 and SM-11 , followed by synthetic procedure 4, reaction with 3-isopropenyl- ⁇ , ⁇ - methylbenzyl amine.
- Example 48 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 5 by the reaction of SM-53 with cinnamyl chloride, followed by synthetic procedure 3, reaction with SM-11.
- Example 49 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 2 by the reaction of SM-17 and 3-isopropenyl- ⁇ , ⁇ - methylbenzyl isocyanate, followed by synthetic procedure 14, reaction with SM-13.
- EXAMPLE 50 Adhesion promoting resin containing electron donor functionality prepared according to synthetic procedure 4 by the reaction of SM-53 and 4-vinyl benzyl chloride, followed by synthetic procedure 14, reaction with SM-13.
- EXAMPLE 51 Adhesion promoting resin containing vinyl silane as electron donor functionality, prepared according to synthetic procedure 4 by the reaction of SM-72 and SM-32.
- EXAMPLE 52 Adhesion promoting resin containing vinyl silane as electron donor functionality prepared according to synthetic procedure 11 by the reaction of SM-29 with trivinylchlorosilane.
- EXAMPLE 53 Adhesion promoting resin containing vinyl silane as electron donor functionality formed by the reaction of SM-28 with methylphenyl vinylchlorosilane
- EXAMPLES 54 to 56 [0183] Examples 54 to 56 show adhesion promoting resins containing pendant silane functionality added to a polymeric chain through a hydrosilation reaction. [0184] EXAMPLE 54: Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-45 and SM-13.
- EXAMPLE 55 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-61 and SM-13.
- EXAMPLE 56 Adhesion promoting resin prepared according to synthetic procedure 14 by the reaction of SM-64 and SM-13.
- Examples 57 to 59 show adhesion promoting resins in which epoxy, electron acceptor, or electron donor functionality is pendant from the polymeric chain, and the silane segment is on the termini of the polymeric chain.
- EXAMPLE 57 Reaction of 3-vinyl-7-oxabicyclo [4.1.0] heptane (prepared according to Procedure 16) with 1 ,1,3,3- tetramethyldisiloxane to give 1-[2-(3-[7-oxabicyclo[4.1.0]heptyl])ethyl]- 1,1,3,3-tetramethyldisiloxane (prepared according to synthetic procedure 17), further reacted with the adhesion promoting resin from Example 1 according to synthetic procedure 14. Similar adhesion promoting resins can be made using the adhesion promoting resins from Examples 2, 3, and 4.
- EXAMPLE 58 Reaction of the adhesion promoting resin from Example 1 with mercaptoethanol according to procedure 1 , followed by reaction with acryloyl chloride according to procedure 9.
- EXAMPLE 59 Reaction of the adhesion promoting resin from Example 1 with mercaptoethanol according to procedure 1 , followed by reaction with cinnamyl chloride according to procedure 6.
- EXAMPLE 60 The volatilities of the neat resins from
- Examples 1 to 4 were determined by TGA (thermogravimetric analysis) with a rpm rate of 10°C/minute with measurement at 200°C. Results are reported in Table !
- EXAMPLE 61 In this example, the volatility of the resins in a curable formulation was measured by TGA during curing. Each of the adhesion promoter resins from Examples 1 through 4 was formulated into an adhesive composition with the components shown in Table 2. [0196]
- the electron donor resin had the following structure:
- C 36 represents a mixture of iso ers of a linear or branched alkyl chain having 36 carbon atoms, resulting from the dimerization of linoleic acid and oleic acid.
- the dimer acid is converted to the alcohol and reacted with 6- maleimido caproic acid to form the bismaleimide electron acceptor resin, or the alcohol is reacted with 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate to form the electron donor resin.
- TGA was performed on the adhesive compositions using an rpm rate of 10°C/minute. Measurement was taken at 200°C. The results are reported in Table 3.
- EXAMPLE 62 The adhesive formulations from Example 61 were tested for adhesive strength to Ag coated Cu and Cu leadframes and compared to a control formulation.
- the control formulation was prepared with the same components and weights of components in Table 2, except that a commercially available polybutadiene containing maleic anhydride (Ricon Corp., Ricon 130, 8%MA) was substituted in place of the inventive adhesion-promoting resin.
- Two sets of leadframe assemblies were prepared for each of the adhesive formulations.
- One set consisted of the adhesive formulation disposed between a 120 X 120 mil silicon die on a Cu leadframe, and the second, of the adhesive formulation disposed between a 120 X 120 mil silicon die on a Ag coated Cu leadframe.
- Sufficient assemblies were prepared for testing at room temperature and at 240°C.
- Each die and leadframe assembly was placed on a hot plate at 200°C for one minute to cure the adhesive.
- Die Shear tests were performed on each assembly using a Royer Instruments, System 552, 100K ; half of the assemblies were tested at room temperature, the other half, at 240°C.
- the 240°C temperature was chosen because that is the temperature at which many current wire-bonding operations are conducted. The results are reported in Table 4 and show that at the critical temperature of 240°C the die shear results are comparable or better than those with the commercially available material.
- the viscosities of the neat resins are considerably lower than the control formulation, making dispensability easier.
- the viscosities of the neat resins were determined on a Brookfield viscometer, spindle # 51 , 10 rpm at ambient temperature and are reported in Table 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92349401A | 2001-08-07 | 2001-08-07 | |
US09/923,494 | 2001-08-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003014248A2 true WO2003014248A2 (en) | 2003-02-20 |
Family
ID=25448775
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2002/020502 WO2003014248A2 (en) | 2001-08-07 | 2002-06-28 | Adhesion promoting resins with cross-linking properties |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2003014248A2 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1422279A1 (en) * | 2002-11-20 | 2004-05-26 | National Starch and Chemical Investment Holding Corporation | Semiconductor package with a die attach adhesive having silane functionality |
EP1422251A2 (en) * | 2002-11-20 | 2004-05-26 | National Starch and Chemical Investment Holding Corporation | Unsaturated compounds containing silane, electron donor and electron acceptor functionality |
WO2006118766A1 (en) * | 2005-04-29 | 2006-11-09 | General Electric Company | Silylated polymer derived from butadiene and solvent-resistant pressure sensitive adhesive composition containing same |
EP2813510A1 (en) * | 2013-06-12 | 2014-12-17 | Shin-Etsu Chemical Co., Ltd. | Thiocarbamatoalky-silanoles as adhesion improvers |
JP2016027044A (en) * | 2015-08-25 | 2016-02-18 | 信越化学工業株式会社 | Novel organic silicon compound, method for producing the same and adhesion improver |
JP2016028047A (en) * | 2015-08-25 | 2016-02-25 | 信越化学工業株式会社 | Novel organic silicon compound, method for producing the same and adhesion improver |
CN105418844A (en) * | 2015-12-31 | 2016-03-23 | 山东大学 | Novel preparation method for hydroxide radical containing liquid rubber |
JP2020515675A (en) * | 2017-07-31 | 2020-05-28 | エルジー・ケム・リミテッド | Modifier, method for producing the same, and modified conjugated diene polymer containing the same |
CN112955332A (en) * | 2018-09-03 | 2021-06-11 | 西索斯公司 | Amino silyl functionalized conjugated dienes, their preparation and use in the manufacture of rubber |
-
2002
- 2002-06-28 WO PCT/US2002/020502 patent/WO2003014248A2/en unknown
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1422279A1 (en) * | 2002-11-20 | 2004-05-26 | National Starch and Chemical Investment Holding Corporation | Semiconductor package with a die attach adhesive having silane functionality |
EP1422251A2 (en) * | 2002-11-20 | 2004-05-26 | National Starch and Chemical Investment Holding Corporation | Unsaturated compounds containing silane, electron donor and electron acceptor functionality |
US6784025B2 (en) | 2002-11-20 | 2004-08-31 | National Starch And Chemical Investment Holding Corporation | Semiconductor package with a die attach adhesive having silane functionality |
EP1422251A3 (en) * | 2002-11-20 | 2005-04-13 | National Starch and Chemical Investment Holding Corporation | Unsaturated compounds containing silane, electron donor and electron acceptor functionality |
WO2006118766A1 (en) * | 2005-04-29 | 2006-11-09 | General Electric Company | Silylated polymer derived from butadiene and solvent-resistant pressure sensitive adhesive composition containing same |
US9238663B2 (en) | 2013-06-12 | 2016-01-19 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compounds, making methods, and adhesion improver |
KR102111629B1 (en) | 2013-06-12 | 2020-05-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Novel organosilicon compound, method for preparing the same and adhesion improver |
US9120828B2 (en) | 2013-06-12 | 2015-09-01 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compounds, making methods, and adhesion improver |
EP2813510A1 (en) * | 2013-06-12 | 2014-12-17 | Shin-Etsu Chemical Co., Ltd. | Thiocarbamatoalky-silanoles as adhesion improvers |
US9243005B2 (en) | 2013-06-12 | 2016-01-26 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compounds, making methods, and adhesion improver |
JP2014240367A (en) * | 2013-06-12 | 2014-12-25 | 信越化学工業株式会社 | Novel organosilicon compound, method for producing the same, and adhesion improver |
KR20200024812A (en) * | 2013-06-12 | 2020-03-09 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Novel organosilicon compound, method for preparing the same and adhesion improver |
EP3428172A1 (en) * | 2013-06-12 | 2019-01-16 | Shin-Etsu Chemical Co., Ltd. | Thiocarbamatoalkyl-silanoles as adhesion improvers |
JP2016028047A (en) * | 2015-08-25 | 2016-02-25 | 信越化学工業株式会社 | Novel organic silicon compound, method for producing the same and adhesion improver |
JP2016027044A (en) * | 2015-08-25 | 2016-02-18 | 信越化学工業株式会社 | Novel organic silicon compound, method for producing the same and adhesion improver |
CN105418844A (en) * | 2015-12-31 | 2016-03-23 | 山东大学 | Novel preparation method for hydroxide radical containing liquid rubber |
JP2020515675A (en) * | 2017-07-31 | 2020-05-28 | エルジー・ケム・リミテッド | Modifier, method for producing the same, and modified conjugated diene polymer containing the same |
US10913805B2 (en) | 2017-07-31 | 2021-02-09 | Lg Chem, Ltd. | Modifier, method for preparing the same, and modified conjugated diene-based polymer including the same |
CN112955332A (en) * | 2018-09-03 | 2021-06-11 | 西索斯公司 | Amino silyl functionalized conjugated dienes, their preparation and use in the manufacture of rubber |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4577745B2 (en) | Adhesion promoter containing silane, carbamate or urea and donor or acceptor functional groups | |
US6699929B2 (en) | Die attach adhesives with vinyl ether and carbamate or urea functionality | |
US6809155B2 (en) | Unsaturated compounds containing silane, electron donor and electron acceptor functionality | |
US20030191270A1 (en) | Electron donors, electron acceptors and adhesion promoters containing disulfide | |
WO2003014248A2 (en) | Adhesion promoting resins with cross-linking properties | |
EP1422279B1 (en) | Semiconductor package with a die attach adhesive having silane functionality | |
US6307001B1 (en) | Curable hybrid electron donor compounds containing vinyl ether | |
US6590018B2 (en) | Vinyl silane compounds containing epoxy functionality | |
US6441121B1 (en) | Epoxy compounds containing styrenic or cinnamyl functionality | |
US6570032B1 (en) | Compounds containing vinyl silane and electron donor or acceptor functionality | |
JP3993518B2 (en) | Compounds containing vinyl silane and electron donor or electron acceptor functionality | |
KR20040069402A (en) | Compounds containing vinyl silane and electron donor or acceptor functionality |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BY BZ CA CH CN CO CR CU CZ DE DM DZ EC EE ES FI GB GD GE GH HR HU ID IL IN IS JP KE KG KP KR LC LK LR LS LT LU LV MA MD MG MN MW MX MZ NO NZ OM PH PL PT RU SD SE SG SI SK SL TJ TM TN TR TZ UA UG UZ VN YU ZA ZM Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ OM PH PL PT RO RU SD SE SG SI SK SL TJ TM TN TR TT TZ UA UG UZ VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR Kind code of ref document: A2 Designated state(s): AT BE CH CY DE DK ES FI FR GB IE IT LU MC NL PT SE TR |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |