RU2335517C2 - Инициируемые органоборан-аминным комплексом полимеризующиеся композиции, содержащие силоксановые полимеризующиеся компоненты, способы их полимеризации, клеевые композиции на их основе и способ склеивания двух подложек с их использованием - Google Patents
Инициируемые органоборан-аминным комплексом полимеризующиеся композиции, содержащие силоксановые полимеризующиеся компоненты, способы их полимеризации, клеевые композиции на их основе и способ склеивания двух подложек с их использованием Download PDFInfo
- Publication number
- RU2335517C2 RU2335517C2 RU2005130177/04A RU2005130177A RU2335517C2 RU 2335517 C2 RU2335517 C2 RU 2335517C2 RU 2005130177/04 A RU2005130177/04 A RU 2005130177/04A RU 2005130177 A RU2005130177 A RU 2005130177A RU 2335517 C2 RU2335517 C2 RU 2335517C2
- Authority
- RU
- Russia
- Prior art keywords
- oligomers
- composition
- compounds
- siloxane
- adhesive
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 218
- 239000000758 substrate Substances 0.000 title claims abstract description 83
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 95
- 238000000034 method Methods 0.000 title claims description 21
- 150000001412 amines Chemical class 0.000 title abstract description 68
- 239000003292 glue Substances 0.000 title abstract description 20
- 238000004026 adhesive bonding Methods 0.000 title abstract description 12
- -1 siloxane chain Chemical group 0.000 claims abstract description 120
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 229920000642 polymer Polymers 0.000 claims abstract description 69
- 239000003054 catalyst Substances 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 8
- 230000005593 dissociations Effects 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 239000000853 adhesive Substances 0.000 claims description 138
- 230000001070 adhesive effect Effects 0.000 claims description 138
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 238000006116 polymerization reaction Methods 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 238000010526 radical polymerization reaction Methods 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 21
- 239000004925 Acrylic resin Substances 0.000 claims description 15
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000003141 primary amines Chemical class 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 10
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910000085 borane Inorganic materials 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 7
- 239000002685 polymerization catalyst Substances 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 11
- 150000001336 alkenes Chemical class 0.000 abstract description 9
- 230000000977 initiatory effect Effects 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 45
- 239000000463 material Substances 0.000 description 33
- 229920000139 polyethylene terephthalate Polymers 0.000 description 28
- 239000005020 polyethylene terephthalate Substances 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 230000006378 damage Effects 0.000 description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 20
- 239000005058 Isophorone diisocyanate Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 19
- 239000004205 dimethyl polysiloxane Substances 0.000 description 19
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 19
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 18
- 229920002554 vinyl polymer Polymers 0.000 description 18
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000003431 cross linking reagent Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 13
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 13
- 239000004926 polymethyl methacrylate Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 150000004678 hydrides Chemical class 0.000 description 11
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 229920000768 polyamine Polymers 0.000 description 10
- 229920000178 Acrylic resin Polymers 0.000 description 9
- 239000004677 Nylon Substances 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 150000002466 imines Chemical class 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229920001778 nylon Polymers 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000013008 moisture curing Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000002841 Lewis acid Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 150000001334 alicyclic compounds Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 229920000307 polymer substrate Polymers 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000012205 single-component adhesive Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920010524 Syndiotactic polystyrene Polymers 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 150000001409 amidines Chemical group 0.000 description 4
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 3
- ZHLSOSXEBSWGDW-UHFFFAOYSA-N 3-aminopropyl triethyl silicate Chemical compound CCO[Si](OCC)(OCC)OCCCN ZHLSOSXEBSWGDW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 150000004819 silanols Chemical class 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000013464 silicone adhesive Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
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- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- 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
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08K5/55—Boron-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
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| US10/377,440 US6777512B1 (en) | 2003-02-28 | 2003-02-28 | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| US10/377,440 | 2003-02-28 |
Publications (2)
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|---|---|
| RU2005130177A RU2005130177A (ru) | 2006-03-20 |
| RU2335517C2 true RU2335517C2 (ru) | 2008-10-10 |
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| RU2005130177/04A RU2335517C2 (ru) | 2003-02-28 | 2004-02-20 | Инициируемые органоборан-аминным комплексом полимеризующиеся композиции, содержащие силоксановые полимеризующиеся компоненты, способы их полимеризации, клеевые композиции на их основе и способ склеивания двух подложек с их использованием |
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| EP (1) | EP1599559B1 (enExample) |
| JP (1) | JP2006522206A (enExample) |
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| AT (1) | ATE535585T1 (enExample) |
| BR (1) | BRPI0407666A (enExample) |
| CA (1) | CA2517364A1 (enExample) |
| MX (1) | MXPA05009154A (enExample) |
| RU (1) | RU2335517C2 (enExample) |
| WO (1) | WO2004078871A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2682587C1 (ru) * | 2013-12-11 | 2019-03-19 | Сикэ Текнолоджи Аг | Предварительная обработка подложек, содержащих ненасыщенные звенья |
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| US6777512B1 (en) * | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| BRPI0411378A (pt) * | 2003-06-09 | 2006-08-01 | Dow Global Technologies Inc | composição polimerizável de duas partes, método de polimerização, método para ligar dois ou mais componentes entre si, método para modificar a superfìcie de um polìmero de energia superficial baixa, método para revestir um substrato, composição de revestimento, laminado e composição polimerizável de uma parte |
| MXPA06001639A (es) | 2003-08-13 | 2006-05-12 | Dow Global Technologies Inc | Metodo para unir sistemas de tuberia y tuberia a equipo, accesorios, dispositivos, estructuras e instrumentos. |
| KR20060063945A (ko) * | 2003-08-13 | 2006-06-12 | 다우 글로벌 테크놀로지스 인크. | 기질과 물체를 접합시키는 방법 |
| GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
| KR20060118559A (ko) * | 2003-12-22 | 2006-11-23 | 다우 글로벌 테크놀로지스 인크. | 촉진된 유기보란 아민 착물 개시 중합 조성물 |
| US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
| US8746747B2 (en) | 2004-03-24 | 2014-06-10 | IPS Corporation—Weld-On Division | Pipe joints |
| US7341285B2 (en) | 2004-03-24 | 2008-03-11 | Ips Corporation Weld-On Division | Chemical fusion of non-metallic pipe joints |
| US7850870B2 (en) * | 2004-10-28 | 2010-12-14 | Dow Corning Corporation | Conductive curable compositions |
| US8202932B2 (en) * | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| EP1866344B1 (en) * | 2005-01-04 | 2009-07-29 | Dow Corning Corporation | Organosillicon functional boron amine catalyst complexes and curable compositions made therefrom |
| EP1833864B1 (en) * | 2005-01-04 | 2013-06-12 | Dow Corning Corporation | Siloxanes and silanes cured by organoborane amine complexes |
| JP5039567B2 (ja) | 2005-02-16 | 2012-10-03 | ダウ・コーニング・コーポレイション | ポリマー粒子、および、有機ボランアミン錯体を用いた封入（ｅｎｃａｐｓｕｌａｔｅｄ）組成物 |
| BRPI0607170A2 (pt) | 2005-02-25 | 2009-08-11 | Dow Global Technologies Inc | método para formar uma estrutura e método para formar um componente estrutural de um veìculo automotivo |
| US7408012B1 (en) * | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| JP2009509026A (ja) * | 2005-09-21 | 2009-03-05 | ダウ・コーニング・コーポレイション | 有機ボランアミン錯体を使用しての、常温リトグラフィー方法 |
| CN101278023A (zh) * | 2005-10-07 | 2008-10-01 | 陶氏环球技术公司 | 酰氨基-有机硼酸盐引发剂体系 |
| US7682663B2 (en) * | 2006-02-23 | 2010-03-23 | Bowling Green State University | Remote curing of polymer coating by gaseous, vaporous or aerosol initiating agent |
| EP2012996A2 (en) * | 2006-04-19 | 2009-01-14 | Dow Global Technologies Inc. | Method for blending materials in an extruder, the manufactured article and material pre-mix |
| US20070261224A1 (en) * | 2006-05-11 | 2007-11-15 | Dow Global Technologies Inc. | Methods and articles in having a fringed microprotrusion surface structure |
| KR101409252B1 (ko) * | 2006-05-23 | 2014-07-03 | 다우 코닝 코포레이션 | 아마이드 작용성 중합체와의 보레인 촉매 착물 및 이로부터제조된 경화성 조성물 |
| US7926870B2 (en) * | 2006-05-26 | 2011-04-19 | Dow Global Technologies Llc | Modular assembly for a vehicle |
| US8097689B2 (en) * | 2006-06-20 | 2012-01-17 | Dow Corning Corporation | Curable organosilicon composition |
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| US20080103274A1 (en) * | 2006-10-12 | 2008-05-01 | Jialanella Gary L | Accelerated organoborane initiated polymerizable compositions |
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| CN101720339B (zh) * | 2007-07-02 | 2013-03-27 | 三菱丽阳株式会社 | 热塑性树脂组合物及成型品 |
| US8377852B2 (en) * | 2007-10-26 | 2013-02-19 | Dow Corning Corporation | Method of preparing a substrate with a composition including an organoborane initiator |
| US8742050B2 (en) | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
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| GB0905488D0 (en) * | 2009-03-31 | 2009-05-13 | Dow Corning | Organopolysiloxane compositions and their production |
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| JP6151639B2 (ja) | 2010-06-30 | 2017-06-21 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性ポリシロキサンコーティング組成物 |
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- 2004-02-20 RU RU2005130177/04A patent/RU2335517C2/ru not_active IP Right Cessation
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| US20040220363A1 (en) | 2004-11-04 |
| US20040210015A1 (en) | 2004-10-21 |
| BRPI0407666A (pt) | 2006-03-01 |
| EP1599559B1 (en) | 2011-11-30 |
| US6949603B2 (en) | 2005-09-27 |
| MXPA05009154A (es) | 2005-10-20 |
| RU2005130177A (ru) | 2006-03-20 |
| US20040242812A1 (en) | 2004-12-02 |
| CN1931904A (zh) | 2007-03-21 |
| KR20050107466A (ko) | 2005-11-11 |
| US6825298B2 (en) | 2004-11-30 |
| US7157399B2 (en) | 2007-01-02 |
| ATE535585T1 (de) | 2011-12-15 |
| CA2517364A1 (en) | 2004-09-16 |
| EP1599559A1 (en) | 2005-11-30 |
| WO2004078871A1 (en) | 2004-09-16 |
| US6777512B1 (en) | 2004-08-17 |
| CN1756821A (zh) | 2006-04-05 |
| CN1931904B (zh) | 2011-04-06 |
| JP2006522206A (ja) | 2006-09-28 |
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