BR112015023457B1 - Composição curável de duas partes - Google Patents
Composição curável de duas partes Download PDFInfo
- Publication number
- BR112015023457B1 BR112015023457B1 BR112015023457-7A BR112015023457A BR112015023457B1 BR 112015023457 B1 BR112015023457 B1 BR 112015023457B1 BR 112015023457 A BR112015023457 A BR 112015023457A BR 112015023457 B1 BR112015023457 B1 BR 112015023457B1
- Authority
- BR
- Brazil
- Prior art keywords
- epoxy
- composition according
- cyanoacrylate
- component
- salts
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 103
- 229920001651 Cyanoacrylate Polymers 0.000 claims abstract description 74
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims abstract description 59
- 239000004593 Epoxy Substances 0.000 claims description 66
- -1 lithium tetrafluoroborate Chemical compound 0.000 claims description 65
- 239000000178 monomer Substances 0.000 claims description 34
- 229920001577 copolymer Polymers 0.000 claims description 25
- 125000002091 cationic group Chemical group 0.000 claims description 17
- 239000011951 cationic catalyst Substances 0.000 claims description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- WPGHPGAUFIJVJF-UHFFFAOYSA-N 3,5-dichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1 WPGHPGAUFIJVJF-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 5
- 150000003553 thiiranes Chemical class 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 claims description 4
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 4
- 239000011118 polyvinyl acetate Substances 0.000 claims description 4
- UTBVIMLZIRIFFR-UHFFFAOYSA-N 2-methylthio-1,3-benzothiazole Chemical compound C1=CC=C2SC(SC)=NC2=C1 UTBVIMLZIRIFFR-UHFFFAOYSA-N 0.000 claims description 3
- WIWGQFIYDDVABV-UHFFFAOYSA-N 4-tert-butyl-1,3-benzothiazole-2-sulfonamide Chemical compound CC(C)(C)C1=CC=CC2=C1N=C(S(N)(=O)=O)S2 WIWGQFIYDDVABV-UHFFFAOYSA-N 0.000 claims description 3
- XCALAYIRFYALSX-UHFFFAOYSA-N 5-chloro-2-methyl-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(C)=NC2=C1 XCALAYIRFYALSX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 235000013824 polyphenols Nutrition 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 claims description 2
- ZFMOJHVRFMOIGF-UHFFFAOYSA-N 2,4,6-trimethoxy-1,3,5,2,4,6-trioxatriborinane Chemical compound COB1OB(OC)OB(OC)O1 ZFMOJHVRFMOIGF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 239000012954 diazonium Chemical group 0.000 claims description 2
- 150000001989 diazonium salts Chemical group 0.000 claims description 2
- VUFLKUMKDWHEMK-UHFFFAOYSA-N fluoroarsenic Chemical compound [As]F VUFLKUMKDWHEMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011967 lanthanide triflate Chemical class 0.000 claims description 2
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000004992 toluidines Chemical class 0.000 claims description 2
- 150000008648 triflates Chemical class 0.000 claims description 2
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005410 aryl sulfonium group Chemical group 0.000 claims 1
- 125000005520 diaryliodonium group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000005409 triarylsulfonium group Chemical group 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 66
- 230000001070 adhesive effect Effects 0.000 abstract description 66
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 abstract description 9
- 239000004830 Super Glue Substances 0.000 abstract description 7
- 239000002245 particle Substances 0.000 description 88
- 229920001971 elastomer Polymers 0.000 description 83
- 239000005060 rubber Substances 0.000 description 80
- 229920000647 polyepoxide Polymers 0.000 description 39
- 239000000758 substrate Substances 0.000 description 39
- 239000003822 epoxy resin Substances 0.000 description 32
- 239000002775 capsule Substances 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 239000000463 material Substances 0.000 description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 19
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 18
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 14
- 231100000647 material safety data sheet Toxicity 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 13
- 230000032683 aging Effects 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229920003023 plastic Polymers 0.000 description 11
- 239000004033 plastic Substances 0.000 description 11
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229920006332 epoxy adhesive Polymers 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- 230000000712 assembly Effects 0.000 description 7
- 238000000429 assembly Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- DFPOZTRSOAQFIK-UHFFFAOYSA-N S,S-dimethyl-beta-propiothetin Chemical compound C[S+](C)CCC([O-])=O DFPOZTRSOAQFIK-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000004930 VINNOL Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 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 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 230000002250 progressing effect Effects 0.000 description 5
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 4
- 239000004594 Masterbatch (MB) Substances 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 229920004482 WACKER® Polymers 0.000 description 3
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 150000002921 oxetanes Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- SLMHHOVQRSSRCV-UHFFFAOYSA-N 2,3-dibromopyridine Chemical compound BrC1=CC=CN=C1Br SLMHHOVQRSSRCV-UHFFFAOYSA-N 0.000 description 2
- MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 2
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 description 2
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 2
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 2
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 2
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 2
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/30—Nitriles
- C08F222/32—Alpha-cyano-acrylic acid; Esters thereof
- C08F222/322—Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
-
- 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
- C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/04—Homopolymers or copolymers of nitriles
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Polyethers (AREA)
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| PCT/IB2014/000771 WO2014140804A2 (en) | 2013-03-15 | 2014-02-21 | Two-part, cyanoacrylate/cationically curable adhesive systems |
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| US7751907B2 (en) | 2007-05-24 | 2010-07-06 | Smiths Medical Asd, Inc. | Expert system for insulin pump therapy |
| US8221345B2 (en) | 2007-05-30 | 2012-07-17 | Smiths Medical Asd, Inc. | Insulin pump based expert system |
| US20090177147A1 (en) | 2008-01-07 | 2009-07-09 | Michael Blomquist | Insulin pump with insulin therapy coaching |
| US8882701B2 (en) | 2009-12-04 | 2014-11-11 | Smiths Medical Asd, Inc. | Advanced step therapy delivery for an ambulatory infusion pump and system |
| US9238100B2 (en) | 2012-06-07 | 2016-01-19 | Tandem Diabetes Care, Inc. | Device and method for training users of ambulatory medical devices |
| US10357606B2 (en) | 2013-03-13 | 2019-07-23 | Tandem Diabetes Care, Inc. | System and method for integration of insulin pumps and continuous glucose monitoring |
| US10016561B2 (en) | 2013-03-15 | 2018-07-10 | Tandem Diabetes Care, Inc. | Clinical variable determination |
| WO2016019133A1 (en) | 2014-07-30 | 2016-02-04 | Tandem Diabetes Care, Inc. | Temporary suspension for closed-loop medicament therapy |
| EP2995663A1 (en) * | 2014-09-12 | 2016-03-16 | Afinitica Technologies, S. L. | Fast and elastic adhesive |
| CN105585879B (zh) * | 2015-12-18 | 2018-05-11 | 杭州福斯特应用材料股份有限公司 | 一种可快速固化的丙烯酸树脂涂料 |
| US10569016B2 (en) | 2015-12-29 | 2020-02-25 | Tandem Diabetes Care, Inc. | System and method for switching between closed loop and open loop control of an ambulatory infusion pump |
| GB2550846B (en) * | 2016-05-23 | 2021-01-13 | Henkel IP & Holding GmbH | Two-part Cyanoacrylate curable adhesive system |
| EP3490725B1 (en) * | 2016-07-26 | 2022-11-09 | PPG Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| US11634524B2 (en) | 2016-07-26 | 2023-04-25 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1 di-activated vinyl compounds and related coatings and processes |
| CN109476081B (zh) | 2016-07-26 | 2021-11-23 | Ppg工业俄亥俄公司 | 使用1,1-二活化的乙烯基化合物的三维印刷方法 |
| EP3491057B1 (en) * | 2016-07-26 | 2022-11-09 | PPG Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
| EP3490724B1 (en) | 2016-07-26 | 2023-09-20 | PPG Industries Ohio, Inc. | Polyurethane coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| WO2018022792A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds |
| JP6770633B2 (ja) | 2016-07-26 | 2020-10-14 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッドPPG Industries Ohio,Inc. | 1,1−二活性化ビニル化合物生成物を含有する複数層硬化性組成物および関連方法 |
| EP4151689B1 (en) * | 2016-07-26 | 2024-09-04 | PPG Industries Ohio, Inc. | Curable compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| US10934411B2 (en) | 2016-09-30 | 2021-03-02 | Ppg Industries Ohio, Inc. | Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms |
| CN106519995A (zh) * | 2016-10-26 | 2017-03-22 | 三友(天津)高分子技术有限公司 | 一种增韧型α‑氰基丙烯酸酯胶粘剂 |
| GB2562107B (en) | 2017-05-05 | 2021-08-11 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| GB2567868B (en) * | 2017-10-27 | 2020-05-06 | Henkel IP & Holding GmbH | Toughened low odour cyanoacrylate compositions |
| CN108641606A (zh) * | 2018-05-16 | 2018-10-12 | 烟台长盈电子科技有限公司 | 一种双组份快干胶及其制备方法 |
| WO2019231694A1 (en) * | 2018-05-29 | 2019-12-05 | Dow Global Technologies Llc | Method for bonding using one-component epoxy adhesive mixtures |
| MX2021000873A (es) | 2018-07-25 | 2021-03-29 | Henkel IP & Holding GmbH | Calce liquido de acrilico epoxico de curado rapido. |
| GB2576791B (en) * | 2018-08-13 | 2022-09-14 | Henkel Ag & Co Kgaa | A two-part cyanoacrylate curable adhesive system |
| GB2576792B (en) * | 2018-08-13 | 2022-09-14 | Henkel Ag & Co Kgaa | A two-part cyanoacrylate curable adhesive system |
| GB2576704B (en) * | 2018-08-16 | 2022-01-12 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| JP7582938B2 (ja) | 2018-10-18 | 2024-11-13 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | 2パートシアノアクリレート/フリーラジカル硬化性接着剤系 |
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| EP3946913B1 (en) * | 2019-03-29 | 2023-10-25 | Compagnie Generale Des Etablissements Michelin | Bonding rubber and plastic surfaces during injection molding |
| KR102295023B1 (ko) * | 2019-07-17 | 2021-08-26 | (주) 이에스은성산업 | 액세서리용 접착제 및 이 액세서리용 접착제를 이용한 스톤타입 액세서리 부재 접착방법 |
| US20220380615A1 (en) * | 2019-09-10 | 2022-12-01 | Toagosei Co., Ltd. | Curable composition, two-liquid type curable composition set, and method for manufacturing adhered product |
| CN114729230A (zh) * | 2019-10-01 | 2022-07-08 | 汉高股份有限及两合公司 | 两部分氰基丙烯酸酯/自由基可固化的粘合剂体系 |
| EP3943521A1 (en) | 2020-07-22 | 2022-01-26 | Bostik SA | Curable two-part adhesive composition |
| CN112040387B (zh) * | 2020-09-01 | 2022-12-06 | 昆山联滔电子有限公司 | 受话器及其制备方法、扬声器及其制备方法 |
| CN114316240B (zh) * | 2020-09-27 | 2023-09-22 | 常州正洁智造科技有限公司 | 一种阳离子型可固化组合物 |
| CN114478978B (zh) * | 2020-11-13 | 2023-05-26 | 万华化学(烟台)容威聚氨酯有限公司 | 一种低膨胀聚氨酯硬泡及其制备方法 |
| WO2022241772A1 (en) * | 2021-05-21 | 2022-11-24 | Henkel Ag & Co. Kgaa | Curable composition and use thereof |
| CN114561154B (zh) * | 2022-02-28 | 2022-10-28 | 浙江久而久化学有限公司 | 一种uv、湿气双固瞬干胶及其制备方法 |
| KR20250026849A (ko) * | 2022-06-28 | 2025-02-25 | 헨켈 아게 운트 코. 카게아아 | 수중 결합 방법 |
| GB202209486D0 (en) * | 2022-06-28 | 2022-08-10 | Henkel Ag & Co Kgaa | Method of underwater bonding |
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| JP5629009B2 (ja) * | 2010-09-15 | 2014-11-19 | ヘンケル アイルランド リミテッド | 二成分系シアノアクリレート/カチオン硬化性接着剤システム |
-
2013
- 2013-03-15 US US13/833,494 patent/US8981027B2/en active Active
-
2014
- 2014-02-21 PL PL14731774T patent/PL2970718T3/pl unknown
- 2014-02-21 WO PCT/IB2014/000771 patent/WO2014140804A2/en not_active Ceased
- 2014-02-21 CN CN201480022829.XA patent/CN105143375B/zh active Active
- 2014-02-21 ES ES14731774T patent/ES2806269T3/es active Active
- 2014-02-21 JP JP2015562375A patent/JP6284959B2/ja active Active
- 2014-02-21 HU HUE14731774A patent/HUE051434T2/hu unknown
- 2014-02-21 BR BR112015023457-7A patent/BR112015023457B1/pt active IP Right Grant
- 2014-02-21 KR KR1020157025893A patent/KR101612243B1/ko active Active
- 2014-02-21 EP EP14731774.7A patent/EP2970718B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| PL2970718T3 (pl) | 2020-09-07 |
| WO2014140804A2 (en) | 2014-09-18 |
| JP2016515153A (ja) | 2016-05-26 |
| WO2014140804A3 (en) | 2014-12-04 |
| JP6284959B2 (ja) | 2018-02-28 |
| KR101612243B1 (ko) | 2016-04-12 |
| EP2970718A2 (en) | 2016-01-20 |
| CN105143375A (zh) | 2015-12-09 |
| EP2970718B1 (en) | 2020-04-22 |
| HUE051434T2 (hu) | 2021-03-01 |
| US8981027B2 (en) | 2015-03-17 |
| ES2806269T3 (es) | 2021-02-17 |
| KR20150119940A (ko) | 2015-10-26 |
| BR112015023457A2 (pt) | 2017-07-18 |
| CN105143375B (zh) | 2017-06-09 |
| US20140275419A1 (en) | 2014-09-18 |
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| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 21/02/2014, OBSERVADAS AS CONDICOES LEGAIS. |
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| B25A | Requested transfer of rights approved |
Owner name: HENKEL AG AND CO. KGAA (DE) |