AU770134B2 - Substance for bonding, coating and sealing, consisting of cyanoacrylates and aldehyde or ketone condensation products - Google Patents
Substance for bonding, coating and sealing, consisting of cyanoacrylates and aldehyde or ketone condensation products Download PDFInfo
- Publication number
- AU770134B2 AU770134B2 AU17785/00A AU1778500A AU770134B2 AU 770134 B2 AU770134 B2 AU 770134B2 AU 17785/00 A AU17785/00 A AU 17785/00A AU 1778500 A AU1778500 A AU 1778500A AU 770134 B2 AU770134 B2 AU 770134B2
- Authority
- AU
- Australia
- Prior art keywords
- composition
- cyanoacrylate
- aldehyde
- coating
- sealing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920001651 Cyanoacrylate Polymers 0.000 title claims description 48
- 150000001299 aldehydes Chemical class 0.000 title claims description 15
- 150000002576 ketones Chemical class 0.000 title claims description 15
- 239000007859 condensation product Substances 0.000 title claims description 12
- 238000007789 sealing Methods 0.000 title claims description 12
- 239000011248 coating agent Substances 0.000 title claims description 10
- 238000000576 coating method Methods 0.000 title claims description 10
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 title description 12
- 239000000126 substance Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 61
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 38
- 230000001070 adhesive effect Effects 0.000 claims description 28
- 239000000853 adhesive Substances 0.000 claims description 26
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000600 sorbitol Substances 0.000 claims description 10
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 9
- 239000004830 Super Glue Substances 0.000 claims description 9
- 235000010356 sorbitol Nutrition 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 8
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000594 mannitol Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- 229930195725 Mannitol Natural products 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 claims description 3
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- -1 aliphatic alcohols Chemical class 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000123 paper Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical group 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 3
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-QDNHWIQGSA-N 1,3-dideuteriopropane Chemical compound [2H]CCC[2H] ATUOYWHBWRKTHZ-QDNHWIQGSA-N 0.000 description 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009974 thixotropic effect Effects 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- OPSFCTBBDIDFJM-UHFFFAOYSA-N (4-chlorophenyl)-cyclopropylmethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CC1 OPSFCTBBDIDFJM-UHFFFAOYSA-N 0.000 description 1
- WRRZKDVBPZBNJN-ONEGZZNKSA-N (e)-4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C=C1 WRRZKDVBPZBNJN-ONEGZZNKSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
- 150000000190 1,4-diols Chemical group 0.000 description 1
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 1
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- XHWHHMNORMIBBB-UHFFFAOYSA-N 2,2,3,3-tetrahydroxybutanedioic acid Chemical compound OC(=O)C(O)(O)C(O)(O)C(O)=O XHWHHMNORMIBBB-UHFFFAOYSA-N 0.000 description 1
- QJXCFMJTJYCLFG-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzaldehyde Chemical compound FC1=C(F)C(F)=C(C=O)C(F)=C1F QJXCFMJTJYCLFG-UHFFFAOYSA-N 0.000 description 1
- ZILXIZUBLXVYPI-UHFFFAOYSA-N 2,4-dinitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C([N+]([O-])=O)=C1 ZILXIZUBLXVYPI-UHFFFAOYSA-N 0.000 description 1
- SQZVYXOKAXPDKY-UHFFFAOYSA-N 2,5-diethyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CCC1=COC(CC)(C=O)CC1 SQZVYXOKAXPDKY-UHFFFAOYSA-N 0.000 description 1
- QMIGEDXMDGEZSR-UHFFFAOYSA-N 2,5-dimethoxyoxolane-3-carbaldehyde Chemical compound COC1CC(C=O)C(OC)O1 QMIGEDXMDGEZSR-UHFFFAOYSA-N 0.000 description 1
- DYVJZCIYRQUXBA-UHFFFAOYSA-N 2,5-dimethyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CC1=COC(C)(C=O)CC1 DYVJZCIYRQUXBA-UHFFFAOYSA-N 0.000 description 1
- UDVDQPMLLBOKKZ-UHFFFAOYSA-N 2,5-dipropyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CCCC1=COC(CCC)(C=O)CC1 UDVDQPMLLBOKKZ-UHFFFAOYSA-N 0.000 description 1
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- DBZAKQWXICEWNW-UHFFFAOYSA-N 2-acetylpyrazine Chemical compound CC(=O)C1=CN=CC=N1 DBZAKQWXICEWNW-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- NDYPMNCLXBBUQQ-UHFFFAOYSA-N 2-methyl-5-propan-2-ylcyclopentene-1-carbaldehyde Chemical compound CC(C)C1CCC(C)=C1C=O NDYPMNCLXBBUQQ-UHFFFAOYSA-N 0.000 description 1
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- NJOZATCIDWVFLW-UHFFFAOYSA-N 3-(2-pentylphenyl)prop-2-enal Chemical compound CCCCCC1=CC=CC=C1C=CC=O NJOZATCIDWVFLW-UHFFFAOYSA-N 0.000 description 1
- URQMEZRQHLCJKR-UHFFFAOYSA-N 3-Methyl-5-propyl-2-cyclohexen-1-one Chemical compound CCCC1CC(C)=CC(=O)C1 URQMEZRQHLCJKR-UHFFFAOYSA-N 0.000 description 1
- WBMRBLKBBVYQSD-UHFFFAOYSA-N 3-methyl-1h-pyrrole-2-carbaldehyde Chemical compound CC=1C=CNC=1C=O WBMRBLKBBVYQSD-UHFFFAOYSA-N 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
- 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
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C09J159/00—Adhesives based on polyacetals; Adhesives based on derivatives of polyacetals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
-
- 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
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/005—Glue sticks
Landscapes
- 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)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19855272 | 1998-12-02 | ||
| DE19855272 | 1998-12-02 | ||
| PCT/EP1999/009287 WO2000032709A1 (de) | 1998-12-02 | 1999-11-30 | Masse zum verkleben, beschichten und dichten aus cyanacrylaten und aldehyd- bzw. keton-kondensationsprodukten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1778500A AU1778500A (en) | 2000-06-19 |
| AU770134B2 true AU770134B2 (en) | 2004-02-12 |
Family
ID=7889544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU17785/00A Ceased AU770134B2 (en) | 1998-12-02 | 1999-11-30 | Substance for bonding, coating and sealing, consisting of cyanoacrylates and aldehyde or ketone condensation products |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1159362A1 (cs) |
| JP (1) | JP2002531629A (cs) |
| KR (1) | KR20010107993A (cs) |
| CN (1) | CN1329648A (cs) |
| AU (1) | AU770134B2 (cs) |
| BR (1) | BR9915814A (cs) |
| CA (1) | CA2353605A1 (cs) |
| CZ (1) | CZ20011972A3 (cs) |
| DE (1) | DE19957677A1 (cs) |
| HU (1) | HUP0104526A3 (cs) |
| ID (1) | ID30447A (cs) |
| NO (1) | NO20012717L (cs) |
| PL (1) | PL348719A1 (cs) |
| RU (1) | RU2238292C2 (cs) |
| SK (1) | SK7432001A3 (cs) |
| TR (1) | TR200101471T2 (cs) |
| UA (1) | UA73930C2 (cs) |
| WO (1) | WO2000032709A1 (cs) |
| ZA (1) | ZA200104538B (cs) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE20000441A1 (en) | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid composition for removing cured product |
| IE20000440A1 (en) * | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid one- or two-part compositions |
| DE102004001493A1 (de) * | 2004-01-09 | 2005-08-04 | Henkel Kgaa | Spaltüberbrückender Cyanacrylat-Klebstoff |
| US8192731B2 (en) | 2005-10-25 | 2012-06-05 | Loctite (R&D) Limited | Thickened cyanoacrylate compositions |
| ATE441685T1 (de) * | 2007-06-15 | 2009-09-15 | Max Planck Ges Zur Firderung D | Verfahren zur herstellung organischer poríser festkírper und mit diesem verfahren herstellbare festkírper |
| GB2463065B (en) * | 2008-09-01 | 2012-11-07 | Loctite R & D Ltd | Transferable curable non-liquid film on a release substrate |
| EP2337825B1 (en) * | 2008-09-26 | 2016-12-21 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| US9457613B2 (en) | 2008-09-26 | 2016-10-04 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| CN103083718B (zh) * | 2011-11-02 | 2015-06-10 | 中国人民解放军军事医学科学院毒物药物研究所 | 一种可生物降解的医用粘合剂及其制备方法和用途 |
| CN105419430A (zh) * | 2015-11-24 | 2016-03-23 | 丹阳镇威汽配有限公司 | 雨刮片刮雨接触面表面涂层及其制备方法 |
| 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 |
| CN109475903B (zh) | 2016-07-26 | 2021-11-26 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物产物的多层可固化组合物及相关工艺 |
| US11078376B2 (en) | 2016-07-26 | 2021-08-03 | 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 |
| CN109804025B (zh) * | 2016-07-26 | 2022-01-11 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物的可固化组合物和相关的涂料和方法 |
| 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 |
| ES2930531T3 (es) | 2016-07-26 | 2022-12-16 | Ppg Ind Ohio Inc | Partículas que tienen superficies funcionalizadas con compuestos de vinilo 1,1-diactivado |
| ES2928648T3 (es) | 2016-07-26 | 2022-11-21 | Ppg Ind Ohio Inc | Procesos de impresión tridimensional mediante el uso de compuestos vinílicos 1,1-di-activados |
| 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 |
| CN107442381B (zh) * | 2017-09-01 | 2021-03-30 | 山东华成中德传动设备有限公司 | 一种木质模具的表面处理方法 |
| GB2567220B (en) | 2017-10-06 | 2021-01-27 | Henkel IP & Holding GmbH | Solid cyanoacrylate compositions comprising thermoplastic polyurethane |
| CN112279999B (zh) * | 2020-11-09 | 2022-03-11 | 广东石油化工学院 | 一种生物降解性可辐射固化的氨酯(甲基)丙烯酸酯及其制备方法 |
| CN112322196A (zh) * | 2020-11-24 | 2021-02-05 | 山东禹王和天下新材料有限公司 | 一种用于聚苯乙烯发泡材料快速粘接的胶黏剂及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846363A (en) * | 1971-02-03 | 1974-11-05 | Nippon Synthetic Chem Ind | Adhesive crayon composition containing sorbitol-benzaldehyde reaction product as additive |
| JPS54107993A (en) * | 1978-02-10 | 1979-08-24 | Matsumoto Seiyaku Kogyo Kk | Alphaacyanoacrylate composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49104931A (cs) * | 1973-02-05 | 1974-10-04 | ||
| RU2112002C1 (ru) * | 1996-04-02 | 1998-05-27 | Акционерное общество закрытого типа "Автоконинвест" | Стабилизированная клеевая композиция |
| RU2193586C1 (ru) * | 2001-04-12 | 2002-11-27 | Институт элементоорганических соединений РАН | Клеевая композиция |
-
1999
- 1999-11-30 AU AU17785/00A patent/AU770134B2/en not_active Ceased
- 1999-11-30 CA CA002353605A patent/CA2353605A1/en not_active Abandoned
- 1999-11-30 BR BR9915814-0A patent/BR9915814A/pt not_active Application Discontinuation
- 1999-11-30 CZ CZ20011972A patent/CZ20011972A3/cs unknown
- 1999-11-30 RU RU2001118044/04A patent/RU2238292C2/ru not_active IP Right Cessation
- 1999-11-30 PL PL99348719A patent/PL348719A1/xx not_active Application Discontinuation
- 1999-11-30 HU HU0104526A patent/HUP0104526A3/hu unknown
- 1999-11-30 TR TR2001/01471T patent/TR200101471T2/xx unknown
- 1999-11-30 UA UA2001064524A patent/UA73930C2/uk unknown
- 1999-11-30 JP JP2000585342A patent/JP2002531629A/ja active Pending
- 1999-11-30 KR KR1020017006731A patent/KR20010107993A/ko not_active Abandoned
- 1999-11-30 DE DE19957677A patent/DE19957677A1/de not_active Ceased
- 1999-11-30 ID IDW00200101450A patent/ID30447A/id unknown
- 1999-11-30 WO PCT/EP1999/009287 patent/WO2000032709A1/de not_active Ceased
- 1999-11-30 CN CN99813954A patent/CN1329648A/zh active Pending
- 1999-11-30 SK SK743-2001A patent/SK7432001A3/sk unknown
- 1999-11-30 EP EP99961028A patent/EP1159362A1/de not_active Withdrawn
-
2001
- 2001-06-01 ZA ZA200104538A patent/ZA200104538B/en unknown
- 2001-06-01 NO NO20012717A patent/NO20012717L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846363A (en) * | 1971-02-03 | 1974-11-05 | Nippon Synthetic Chem Ind | Adhesive crayon composition containing sorbitol-benzaldehyde reaction product as additive |
| JPS54107993A (en) * | 1978-02-10 | 1979-08-24 | Matsumoto Seiyaku Kogyo Kk | Alphaacyanoacrylate composition |
Also Published As
| Publication number | Publication date |
|---|---|
| TR200101471T2 (tr) | 2001-11-21 |
| BR9915814A (pt) | 2001-08-21 |
| CN1329648A (zh) | 2002-01-02 |
| RU2238292C2 (ru) | 2004-10-20 |
| PL348719A1 (en) | 2002-06-03 |
| ZA200104538B (en) | 2002-09-02 |
| SK7432001A3 (en) | 2002-01-07 |
| WO2000032709A1 (de) | 2000-06-08 |
| JP2002531629A (ja) | 2002-09-24 |
| HUP0104526A3 (en) | 2003-07-28 |
| KR20010107993A (ko) | 2001-12-07 |
| UA73930C2 (en) | 2005-10-17 |
| NO20012717D0 (no) | 2001-06-01 |
| NO20012717L (no) | 2001-06-01 |
| CZ20011972A3 (cs) | 2001-11-14 |
| ID30447A (id) | 2001-12-06 |
| DE19957677A1 (de) | 2000-06-08 |
| CA2353605A1 (en) | 2000-06-08 |
| EP1159362A1 (de) | 2001-12-05 |
| HUP0104526A2 (hu) | 2002-03-28 |
| AU1778500A (en) | 2000-06-19 |
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