PT2511355E - Adesivo de cianoacrilato com resistência à água melhorada - Google Patents
Adesivo de cianoacrilato com resistência à água melhorada Download PDFInfo
- Publication number
- PT2511355E PT2511355E PT111620548T PT11162054T PT2511355E PT 2511355 E PT2511355 E PT 2511355E PT 111620548 T PT111620548 T PT 111620548T PT 11162054 T PT11162054 T PT 11162054T PT 2511355 E PT2511355 E PT 2511355E
- Authority
- PT
- Portugal
- Prior art keywords
- bis
- cyanoacrylate
- adhesive
- meth
- substrates
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 21
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 title description 9
- 239000004830 Super Glue Substances 0.000 title description 8
- 230000001070 adhesive effect Effects 0.000 claims description 81
- 239000000853 adhesive Substances 0.000 claims description 80
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical class OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical class [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 33
- -1 1,4-bis (tripropoxysilyl) 1,5-bis (trimethoxysilyl) pentane Chemical compound 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000004825 One-part adhesive Substances 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 239000000919 ceramic Substances 0.000 claims description 11
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- BUJVPKZRXOTBGA-UHFFFAOYSA-N 2-trimethoxysilylethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C=C BUJVPKZRXOTBGA-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 claims description 4
- IQDPHMACOQAPBQ-UHFFFAOYSA-N 2-ethoxyethyl 2-cyanoprop-2-enoate Chemical compound CCOCCOC(=O)C(=C)C#N IQDPHMACOQAPBQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- PYOKTQVLKOAHRM-UHFFFAOYSA-N triethoxy(3-triethoxysilylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC[Si](OCC)(OCC)OCC PYOKTQVLKOAHRM-UHFFFAOYSA-N 0.000 claims description 3
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 claims description 3
- LQASLKRKZDJCBO-UHFFFAOYSA-N trimethoxy(3-trimethoxysilylpropyl)silane Chemical compound CO[Si](OC)(OC)CCC[Si](OC)(OC)OC LQASLKRKZDJCBO-UHFFFAOYSA-N 0.000 claims description 3
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229910052573 porcelain Inorganic materials 0.000 claims description 2
- NRYWFNLVRORSCA-UHFFFAOYSA-N triethoxy(6-triethoxysilylhexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC[Si](OCC)(OCC)OCC NRYWFNLVRORSCA-UHFFFAOYSA-N 0.000 claims description 2
- NIINUVYELHEORX-UHFFFAOYSA-N triethoxy(triethoxysilylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)C[Si](OCC)(OCC)OCC NIINUVYELHEORX-UHFFFAOYSA-N 0.000 claims description 2
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 claims description 2
- DJYGUVIGOGFJOF-UHFFFAOYSA-N trimethoxy(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)OC DJYGUVIGOGFJOF-UHFFFAOYSA-N 0.000 claims description 2
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 2
- QDOHRQCMIFOPEY-UHFFFAOYSA-N tripropoxy(2-tripropoxysilylethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CC[Si](OCCC)(OCCC)OCCC QDOHRQCMIFOPEY-UHFFFAOYSA-N 0.000 claims description 2
- BKBQKRDWRZADLL-UHFFFAOYSA-N tripropoxy(3-tripropoxysilylpropyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CCC[Si](OCCC)(OCCC)OCCC BKBQKRDWRZADLL-UHFFFAOYSA-N 0.000 claims description 2
- BZIXIRYKSIMLOB-UHFFFAOYSA-N tripropoxy(tripropoxysilylmethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C[Si](OCCC)(OCCC)OCCC BZIXIRYKSIMLOB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- JPPHEZSCZWYTOP-UHFFFAOYSA-N trimethoxysilylmethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C=C JPPHEZSCZWYTOP-UHFFFAOYSA-N 0.000 claims 7
- PSLRXNFNXYNXEK-UHFFFAOYSA-N 2-triethoxysilylethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C=C PSLRXNFNXYNXEK-UHFFFAOYSA-N 0.000 claims 4
- HGBFVOSZYVRIHY-UHFFFAOYSA-N 2-cyanoprop-2-enamide Chemical compound NC(=O)C(=C)C#N HGBFVOSZYVRIHY-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 claims 1
- KGJLSJJEKOSBCO-UHFFFAOYSA-N 2-methoxypropylurea Chemical compound COC(C)CNC(N)=O KGJLSJJEKOSBCO-UHFFFAOYSA-N 0.000 claims 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 claims 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- OEYRKUSFKACRRP-UHFFFAOYSA-N benzoyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OC(=O)C1=CC=CC=C1 OEYRKUSFKACRRP-UHFFFAOYSA-N 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims 1
- IAGREDBVCFAKQR-UHFFFAOYSA-N hexyl(tripropoxy)silane Chemical compound CCCCCC[Si](OCCC)(OCCC)OCCC IAGREDBVCFAKQR-UHFFFAOYSA-N 0.000 claims 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 1
- QOZPAYSTKGZHHF-UHFFFAOYSA-N tert-butyl 2-cyanoprop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)C#N QOZPAYSTKGZHHF-UHFFFAOYSA-N 0.000 claims 1
- PQVPWZHUJMEZSA-UHFFFAOYSA-N triethoxy(4-triethoxysilylbutyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCC[Si](OCC)(OCC)OCC PQVPWZHUJMEZSA-UHFFFAOYSA-N 0.000 claims 1
- OTRIBZPALGOVNZ-UHFFFAOYSA-N trimethoxy(4-trimethoxysilylbutyl)silane Chemical compound CO[Si](OC)(OC)CCCC[Si](OC)(OC)OC OTRIBZPALGOVNZ-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 8
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 238000004851 dishwashing Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 150000003983 crown ethers Chemical class 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229940053009 ethyl cyanoacrylate Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 230000000712 assembly Effects 0.000 description 3
- 238000000429 assembly Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- IFGHEEXVAVTLKH-UHFFFAOYSA-N 3,3-dicyanoprop-2-enoic acid Chemical class OC(=O)C=C(C#N)C#N IFGHEEXVAVTLKH-UHFFFAOYSA-N 0.000 description 2
- MDAXRQUXUUOQBR-UHFFFAOYSA-N 3-triethoxysilylpropyl benzoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C1=CC=CC=C1 MDAXRQUXUUOQBR-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical compound CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 2
- 229950010048 enbucrilate Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RPQUGMLCZLGZTG-UHFFFAOYSA-N octyl cyanoacrylate Chemical compound CCCCCCCCOC(=O)C(=C)C#N RPQUGMLCZLGZTG-UHFFFAOYSA-N 0.000 description 2
- SXRFXXNXVPFXDU-UHFFFAOYSA-N pentyl 2-cyanoprop-2-enoate Chemical compound CCCCCOC(=O)C(=C)C#N SXRFXXNXVPFXDU-UHFFFAOYSA-N 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- ZTYMNUBYYQNBFP-UHFFFAOYSA-N propyl 2-cyanoprop-2-enoate Chemical compound CCCOC(=O)C(=C)C#N ZTYMNUBYYQNBFP-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000000196 viscometry Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- AXWCVSOBRFLCJG-UHFFFAOYSA-N 2,5,12,15,22,25-hexaoxatetracyclo[24.4.0.06,11.016,21]triaconta-1(30),6,8,10,16,18,20,26,28-nonaene Chemical compound O1CCOC2=CC=CC=C2OCCOC2=CC=CC=C2OCCOC2=CC=CC=C21 AXWCVSOBRFLCJG-UHFFFAOYSA-N 0.000 description 1
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 1
- ZKPRXIQBIPYAHO-UHFFFAOYSA-N 2-(5-phenylpentoxycarbonyl)benzoic acid;phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(=O)OCCCCCC1=CC=CC=C1 ZKPRXIQBIPYAHO-UHFFFAOYSA-N 0.000 description 1
- WXAFTQJQXYGOKV-UHFFFAOYSA-N 2-ethylhexyl 2-cyanoprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(=C)C#N WXAFTQJQXYGOKV-UHFFFAOYSA-N 0.000 description 1
- JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical compound COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 description 1
- CQVWXNBVRLKXPE-UHFFFAOYSA-N 2-octyl cyanoacrylate Chemical compound CCCCCCC(C)OC(=O)C(=C)C#N CQVWXNBVRLKXPE-UHFFFAOYSA-N 0.000 description 1
- FYAFZVREGWFFHQ-UHFFFAOYSA-N 2-silylethoxysilane Chemical compound [SiH3]CCO[SiH3] FYAFZVREGWFFHQ-UHFFFAOYSA-N 0.000 description 1
- DZFSDWSRRNKLHQ-UHFFFAOYSA-N 2-triethoxysilylethyl benzoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C1=CC=CC=C1 DZFSDWSRRNKLHQ-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- HYFWOBSAALCFRS-UHFFFAOYSA-N 3-trimethoxysilylpropyl benzoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C1=CC=CC=C1 HYFWOBSAALCFRS-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- HFQQYIUTYJVYFZ-UHFFFAOYSA-N 4-methylpentyl 2-cyanoprop-2-enoate Chemical compound CC(C)CCCOC(=O)C(=C)C#N HFQQYIUTYJVYFZ-UHFFFAOYSA-N 0.000 description 1
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- TVVFYODLXMCXMG-UHFFFAOYSA-N C(C=C)(=O)OCCO[Si](OCC)(OCC)C1CCCCC1 Chemical compound C(C=C)(=O)OCCO[Si](OCC)(OCC)C1CCCCC1 TVVFYODLXMCXMG-UHFFFAOYSA-N 0.000 description 1
- KDCKNAMXPYLGIW-UHFFFAOYSA-N CCO[Si]([SiH3])(OCC)OCC Chemical compound CCO[Si]([SiH3])(OCC)OCC KDCKNAMXPYLGIW-UHFFFAOYSA-N 0.000 description 1
- FVFMAKDSUFMFAC-UHFFFAOYSA-N CO[Si](C(C[Si](OC)(OC)OC)[Si](OC)(OC)OC)(OC)OC Chemical compound CO[Si](C(C[Si](OC)(OC)OC)[Si](OC)(OC)OC)(OC)OC FVFMAKDSUFMFAC-UHFFFAOYSA-N 0.000 description 1
- VHEPEMZAFBGZJG-UHFFFAOYSA-N CO[Si](OC)(OC)CCC[SiH3] Chemical compound CO[Si](OC)(OC)CCC[SiH3] VHEPEMZAFBGZJG-UHFFFAOYSA-N 0.000 description 1
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- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 241000760038 Monosis Species 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 description 1
- YIKHYBUYXBUMHZ-UHFFFAOYSA-N [cyclohexyl(dimethoxy)silyl]oxymethyl prop-2-enoate Chemical compound C(C=C)(=O)OCO[Si](OC)(OC)C1CCCCC1 YIKHYBUYXBUMHZ-UHFFFAOYSA-N 0.000 description 1
- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FNEPSTUXZLEUCK-UHFFFAOYSA-N benzo-15-crown-5 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C21 FNEPSTUXZLEUCK-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- KRIJKJDTULGZJO-UHFFFAOYSA-N butan-2-yl 2-cyanoprop-2-enoate Chemical compound CCC(C)OC(=O)C(=C)C#N KRIJKJDTULGZJO-UHFFFAOYSA-N 0.000 description 1
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 1
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002633 crown compound Substances 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical class N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- ILRMPAUJTPZAIQ-UHFFFAOYSA-N cyclohexyl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OC1CCCCC1 ILRMPAUJTPZAIQ-UHFFFAOYSA-N 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- MXCSCGGRLMRZMF-UHFFFAOYSA-N dibenzo-30-crown-10 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C2OCCOCCOCCOCCOC2=CC=CC=C21 MXCSCGGRLMRZMF-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- WVXQYJXDTJWWEA-UHFFFAOYSA-N heptyl 2-cyanoprop-2-enoate Chemical compound CCCCCCCOC(=O)C(=C)C#N WVXQYJXDTJWWEA-UHFFFAOYSA-N 0.000 description 1
- HGBCAGWLIQGSMW-UHFFFAOYSA-N hexanedioic acid;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical class OC(=O)CCCCC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O HGBCAGWLIQGSMW-UHFFFAOYSA-N 0.000 description 1
- XDZLHTBOHLGGCJ-UHFFFAOYSA-N hexyl 2-cyanoprop-2-enoate Chemical compound CCCCCCOC(=O)C(=C)C#N XDZLHTBOHLGGCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- QRWOVIRDHQJFDB-UHFFFAOYSA-N isobutyl cyanoacrylate Chemical compound CC(C)COC(=O)C(=C)C#N QRWOVIRDHQJFDB-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000006060 molten glass Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- HTLUDKXTQGHFHT-UHFFFAOYSA-N oxolan-2-yl 2-cyanoprop-2-enoate Chemical compound N#CC(=C)C(=O)OC1CCCO1 HTLUDKXTQGHFHT-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- MOVRCMBPGBESLI-UHFFFAOYSA-N prop-2-enoyloxysilicon Chemical compound [Si]OC(=O)C=C MOVRCMBPGBESLI-UHFFFAOYSA-N 0.000 description 1
- ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical group C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 description 1
- SQGOMFWCSGKGEP-UHFFFAOYSA-N propan-2-yl 2-cyanoprop-2-enoate Chemical compound CC(C)OC(=O)C(=C)C#N SQGOMFWCSGKGEP-UHFFFAOYSA-N 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
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- OWJVJXSAWUDRAN-UHFFFAOYSA-N silyl benzoate Chemical compound [SiH3]OC(=O)C1=CC=CC=C1 OWJVJXSAWUDRAN-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- 230000035882 stress Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- JGABXROLARSPEN-UHFFFAOYSA-N tri(propan-2-yloxy)silane Chemical group CC(C)O[SiH](OC(C)C)OC(C)C JGABXROLARSPEN-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- MAFPECYMNWKRHR-UHFFFAOYSA-N trimethoxy(5-trimethoxysilylpentyl)silane Chemical compound CO[Si](OC)(OC)CCCCC[Si](OC)(OC)OC MAFPECYMNWKRHR-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AQNKQXPQSSNUBE-UHFFFAOYSA-N tripropoxy(4-tripropoxysilylbutyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CCCC[Si](OCCC)(OCCC)OCCC AQNKQXPQSSNUBE-UHFFFAOYSA-N 0.000 description 1
- BQEMHSFOEDTNEP-UHFFFAOYSA-N tripropoxy(6-tripropoxysilylhexyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CCCCCC[Si](OCCC)(OCCC)OCCC BQEMHSFOEDTNEP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
-
- 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
- C09J183/02—Polysilicates
-
- 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
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11162054.8A EP2511355B1 (en) | 2011-04-12 | 2011-04-12 | Cyanoacrylate adhesive with improved water resistance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT2511355E true PT2511355E (pt) | 2014-01-28 |
Family
ID=44351866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT111620548T PT2511355E (pt) | 2011-04-12 | 2011-04-12 | Adesivo de cianoacrilato com resistência à água melhorada |
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| Country | Link |
|---|---|
| US (1) | US9096778B2 (enExample) |
| EP (1) | EP2511355B1 (enExample) |
| JP (1) | JP5963846B2 (enExample) |
| KR (1) | KR20140021599A (enExample) |
| CN (1) | CN103476885B (enExample) |
| BR (1) | BR112013026068A2 (enExample) |
| CA (1) | CA2821662A1 (enExample) |
| ES (1) | ES2443163T3 (enExample) |
| MX (1) | MX2013011859A (enExample) |
| PT (1) | PT2511355E (enExample) |
| WO (1) | WO2012139965A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103031012B (zh) * | 2012-12-14 | 2016-06-15 | 长沙岱勒新材料科技股份有限公司 | 一种组合物及其用于制备金刚石线锯的方法 |
| US8877868B2 (en) | 2013-02-26 | 2014-11-04 | Henkel IP & Holding GmbH | Hot melt adhesive comprising cyanoacrylate curing compounds |
| US9783714B2 (en) | 2013-03-15 | 2017-10-10 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| ES2651855T3 (es) * | 2013-05-21 | 2018-01-30 | Henkel IP & Holding GmbH | Composiciones de cianoacrilato |
| TWI629327B (zh) * | 2013-09-03 | 2018-07-11 | 東亞合成股份有限公司 | Adhesive composition (1) |
| CN103555212B (zh) * | 2013-10-24 | 2015-03-18 | 北京天山新材料技术有限公司 | 一种耐湿热氰基丙烯酸酯胶粘剂 |
| CN103694903B (zh) * | 2013-12-02 | 2015-07-01 | 南通瑞普埃尔生物工程有限公司 | 一种瞬干胶粘剂及其制备方法 |
| CN103666293B (zh) * | 2013-12-02 | 2015-04-29 | 南通瑞普埃尔生物工程有限公司 | 一种耐热性瞬干粘合剂及其制备方法 |
| TWI664224B (zh) | 2014-12-12 | 2019-07-01 | 日商東亞合成股份有限公司 | Two-liquid type hardening composition |
| GB2544101B (en) * | 2015-11-06 | 2020-07-15 | Henkel IP & Holding GmbH | Rubber toughened cyanoacrylate compositions and uses thereof |
| CN105315933B (zh) * | 2015-11-24 | 2017-08-04 | 金辉 | 一种抗剥离瞬干胶及其制备方法 |
| TWI752043B (zh) * | 2016-06-28 | 2022-01-11 | 日商東亞合成股份有限公司 | 2-氰基丙烯酸酯系接著劑組成物 |
| JP6424868B2 (ja) | 2016-09-07 | 2018-11-21 | 信越化学工業株式会社 | シラン変性共重合体、その製造方法および密着向上剤 |
| CN108930386A (zh) * | 2017-05-26 | 2018-12-04 | 高志明 | 一种天然纤维高强度复合地板 |
| GB2567869B (en) * | 2017-10-27 | 2021-08-11 | Henkel IP & Holding GmbH | Toughened humidity/thermal resistant cyanoacrylate compositions |
| GB2567868B (en) * | 2017-10-27 | 2020-05-06 | Henkel IP & Holding GmbH | Toughened low odour cyanoacrylate compositions |
| US10537509B2 (en) * | 2018-04-03 | 2020-01-21 | Tristar Colors, Llc | Nail glue compositions |
| CN110575561B (zh) * | 2019-09-16 | 2022-04-22 | 浙江派菲特新材料科技有限公司 | 一种高抗冲击性高亲水性的医用正丁酯胶 |
| CN112826976B (zh) * | 2021-03-10 | 2024-01-16 | 江西博恩锐尔生物科技有限公司 | 一种低白化氰基丙烯酸酯医用粘合剂制备 |
| CN114395334B (zh) * | 2022-03-15 | 2023-09-26 | 宁波百仕高联合工业有限公司 | 一种高耐水性瞬间胶的制备方法 |
| EP4567083A1 (en) * | 2023-12-04 | 2025-06-11 | Bostik SA | Use of a composition comprising n-heptylcyanoacrylate in an electric, electronic or optical device |
| CN117567862B (zh) * | 2023-12-27 | 2024-10-18 | 天茂石化江苏有限公司 | 一种疏水的尼龙复合材料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2784127A (en) | 1954-06-02 | 1957-03-05 | Eastman Kodak Co | Plasticized monomeric adhesive compositions and articles prepared therefrom |
| US3262828A (en) | 1962-12-03 | 1966-07-26 | Owens Illinois Glass Co | Method for joining glass parts |
| US3722599A (en) | 1967-12-01 | 1973-03-27 | Minnesota Mining & Mfg | Fluorocyanoacrylates |
| US3527841A (en) | 1968-04-10 | 1970-09-08 | Eastman Kodak Co | Alpha-cyanoacrylate adhesive compositions |
| IE35508B1 (en) * | 1971-08-11 | 1976-03-03 | Intercontinental Chem Co Ltd | Method of forming adhesive bonds between surfaces |
| JPS48103633A (enExample) * | 1972-04-14 | 1973-12-26 | ||
| US3940362A (en) | 1972-05-25 | 1976-02-24 | Johnson & Johnson | Cross-linked cyanoacrylate adhesive compositions |
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| CA1284653C (en) | 1984-01-27 | 1991-06-04 | Loctite (Ireland) Limited | Instant adhesive composition utilizing calixarene accelerators |
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| US4636539A (en) | 1984-01-30 | 1987-01-13 | Loctite (Ireland) Limited | Instant adhesive composition utilizing calixarene accelerators |
| DE3414805A1 (de) * | 1984-04-19 | 1985-10-24 | Bayer Ag, 5090 Leverkusen | Stabilisierte klebstoffe |
| IE59509B1 (en) | 1987-01-21 | 1994-03-09 | Loctite Ireland Ltd | Functionalised oxacalixarenes, their preparation and use in instant adhesive compositions |
| JPH0694548B2 (ja) | 1985-07-19 | 1994-11-24 | 高圧ガス工業株式会社 | α―シアノアクリレート接着剤組成物 |
| SU1328361A1 (ru) | 1986-03-14 | 1987-08-07 | Центральный научно-исследовательский институт бытового обслуживания | Способ склеивани хрустального стекла |
| US4837260A (en) | 1986-05-23 | 1989-06-06 | Toagosei Chemical Industry Co., Ltd. | Cyanoacrylate compositions |
| US4753695A (en) | 1987-03-02 | 1988-06-28 | Alexander George E | Apparatus and a method for repairing a windshield |
| SU1564172A1 (ru) | 1987-12-14 | 1990-05-15 | Центральный Научно-Исследовательский Институт Бытового Обслуживания Населения | Способ склеивани хрустального стекла |
| US5314562A (en) | 1990-11-29 | 1994-05-24 | Loctite Corporation | Consumer polyolefin primer |
| JPH05207634A (ja) | 1992-01-27 | 1993-08-13 | Sumitomo Electric Ind Ltd | 直埋ｏｆケーブル線路の漏油区間検出方法 |
| JPH06100838A (ja) | 1992-09-18 | 1994-04-12 | Three Bond Co Ltd | 接着剤組成物 |
| US5328687A (en) | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
| US5480935A (en) | 1994-09-01 | 1996-01-02 | Medlogic Global Corporation | Cyanoacrylate adhesive compositions |
| ES2189966T3 (es) | 1996-08-16 | 2003-07-16 | Loctite R & D Ltd | Composiciones adhesivas de cianoacrilato para unir vidrio. |
| IES990974A2 (en) | 1998-11-23 | 2000-05-31 | Loctite R & D Ltd | Cyanoacrylate Compositions |
| US6835789B1 (en) | 2003-06-18 | 2004-12-28 | Loctite (R&D) Limited | Cyanoacrylate compositions |
| JP2005162850A (ja) * | 2003-12-02 | 2005-06-23 | Koatsu Gas Kogyo Co Ltd | 熱可塑性エラストマー用接着剤 |
| EP1951831B1 (de) * | 2005-11-10 | 2011-02-23 | Henkel AG & Co. KGaA | Kleb-, dicht- und beschichtungsstoffe mit glaspartikeln als füllstoff |
| US7659423B1 (en) | 2006-04-18 | 2010-02-09 | Loctite (R&D) Limited | Method of preparing electron deficient olefins in polar solvents |
| US7718821B1 (en) | 2006-12-19 | 2010-05-18 | Loctite (R&D) Limited | Method of preparing electron deficient olefins |
-
2011
- 2011-04-12 ES ES11162054.8T patent/ES2443163T3/es active Active
- 2011-04-12 PT PT111620548T patent/PT2511355E/pt unknown
- 2011-04-12 EP EP11162054.8A patent/EP2511355B1/en not_active Not-in-force
-
2012
- 2012-04-05 KR KR1020137026908A patent/KR20140021599A/ko not_active Withdrawn
- 2012-04-05 BR BR112013026068A patent/BR112013026068A2/pt not_active IP Right Cessation
- 2012-04-05 WO PCT/EP2012/056270 patent/WO2012139965A1/en not_active Ceased
- 2012-04-05 CA CA2821662A patent/CA2821662A1/en not_active Abandoned
- 2012-04-05 CN CN201280017465.7A patent/CN103476885B/zh not_active Expired - Fee Related
- 2012-04-05 JP JP2014504259A patent/JP5963846B2/ja not_active Expired - Fee Related
- 2012-04-05 MX MX2013011859A patent/MX2013011859A/es active IP Right Grant
-
2013
- 2013-03-05 US US13/784,968 patent/US9096778B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX2013011859A (es) | 2013-11-01 |
| CN103476885B (zh) | 2015-06-10 |
| ES2443163T3 (es) | 2014-02-18 |
| EP2511355A1 (en) | 2012-10-17 |
| JP5963846B2 (ja) | 2016-08-03 |
| BR112013026068A2 (pt) | 2019-09-24 |
| EP2511355B1 (en) | 2013-10-23 |
| KR20140021599A (ko) | 2014-02-20 |
| WO2012139965A1 (en) | 2012-10-18 |
| JP2014515775A (ja) | 2014-07-03 |
| CN103476885A (zh) | 2013-12-25 |
| US20130174981A1 (en) | 2013-07-11 |
| US9096778B2 (en) | 2015-08-04 |
| CA2821662A1 (en) | 2012-10-18 |
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