ZA200104538B - 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
- ZA200104538B ZA200104538B ZA200104538A ZA200104538A ZA200104538B ZA 200104538 B ZA200104538 B ZA 200104538B ZA 200104538 A ZA200104538 A ZA 200104538A ZA 200104538 A ZA200104538 A ZA 200104538A ZA 200104538 B ZA200104538 B ZA 200104538B
- Authority
- ZA
- South Africa
- Prior art keywords
- composition
- cyanoacrylate
- aldehyde
- weight
- substance
- Prior art date
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- 229920001651 Cyanoacrylate Polymers 0.000 title claims description 47
- 150000001299 aldehydes Chemical class 0.000 title claims description 17
- 150000002576 ketones Chemical class 0.000 title claims description 17
- 239000007859 condensation product Substances 0.000 title claims description 13
- 238000007789 sealing Methods 0.000 title claims description 9
- 239000011248 coating agent Substances 0.000 title claims description 7
- 238000000576 coating method Methods 0.000 title claims description 7
- 239000000126 substance Substances 0.000 title claims description 6
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 title description 13
- 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 37
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000003077 polyols Chemical class 0.000 claims description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000594 mannitol Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000000600 sorbitol Substances 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 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 8
- 235000010356 sorbitol Nutrition 0.000 claims description 8
- 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 7
- 239000004830 Super Glue Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229930195725 Mannitol Natural products 0.000 claims description 5
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- 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
- 239000002562 thickening agent Substances 0.000 claims description 5
- 230000008569 process Effects 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
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 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
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 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
- 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 2
- 239000000945 filler Substances 0.000 claims description 2
- -1 aliphatic alcohols Chemical class 0.000 description 29
- 230000001070 adhesive effect Effects 0.000 description 27
- 239000000853 adhesive Substances 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 14
- 125000004432 carbon atom Chemical group C* 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
- 238000006116 polymerization reaction Methods 0.000 description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical group 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
- 239000000499 gel Substances 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
- 239000002253 acid Substances 0.000 description 5
- 239000003054 catalyst 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
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 4
- 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
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 2
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-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
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 2
- IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-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
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-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
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- 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
- 239000011668 ascorbic acid Substances 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 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
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- XPCJYQUUKUVAMI-UHFFFAOYSA-N cyclohex-2-ene-1-carbaldehyde Chemical compound O=CC1CCCC=C1 XPCJYQUUKUVAMI-UHFFFAOYSA-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 group 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
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009974 thixotropic effect Effects 0.000 description 2
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- CIXAYNMKFFQEFU-UHFFFAOYSA-N (4-Methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 description 1
- OPSFCTBBDIDFJM-UHFFFAOYSA-N (4-chlorophenyl)-cyclopropylmethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CC1 OPSFCTBBDIDFJM-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- FUJZJBCWPIOHHN-QHHAFSJGSA-N (e)-1-phenylbut-2-en-1-one Chemical compound C\C=C\C(=O)C1=CC=CC=C1 FUJZJBCWPIOHHN-QHHAFSJGSA-N 0.000 description 1
- LVGUHATVVHIJET-CMDGGOBGSA-N (e)-1-phenylpent-1-en-3-one Chemical compound CCC(=O)\C=C\C1=CC=CC=C1 LVGUHATVVHIJET-CMDGGOBGSA-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
- DBNWBEGCONIRGQ-UHFFFAOYSA-N 1,1-diphenylpropan-2-one Chemical compound C=1C=CC=CC=1C(C(=O)C)C1=CC=CC=C1 DBNWBEGCONIRGQ-UHFFFAOYSA-N 0.000 description 1
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 150000000180 1,2-diols Chemical class 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
- 150000000190 1,4-diols Chemical group 0.000 description 1
- OQBCJXUAQQMTRW-UHFFFAOYSA-N 1-(1-methylcyclopropyl)ethanone Chemical compound CC(=O)C1(C)CC1 OQBCJXUAQQMTRW-UHFFFAOYSA-N 0.000 description 1
- XWCIICLTKWRWCI-UHFFFAOYSA-N 1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC(=O)C1=C(C)C=C(C)C=C1C XWCIICLTKWRWCI-UHFFFAOYSA-N 0.000 description 1
- IQOJTGSBENZIOL-UHFFFAOYSA-N 1-(2-Furanyl)-2-propanone Chemical compound CC(=O)CC1=CC=CO1 IQOJTGSBENZIOL-UHFFFAOYSA-N 0.000 description 1
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 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
- QQXJNLYVPPBERR-UHFFFAOYSA-N 1-phenyldecan-1-one Chemical compound CCCCCCCCCC(=O)C1=CC=CC=C1 QQXJNLYVPPBERR-UHFFFAOYSA-N 0.000 description 1
- DJNJZIFFCJTUDS-UHFFFAOYSA-N 1-phenyldodecan-1-one Chemical compound CCCCCCCCCCCC(=O)C1=CC=CC=C1 DJNJZIFFCJTUDS-UHFFFAOYSA-N 0.000 description 1
- UDEVCZRUNOLVLU-UHFFFAOYSA-N 1-phenyloctan-1-one Chemical compound CCCCCCCC(=O)C1=CC=CC=C1 UDEVCZRUNOLVLU-UHFFFAOYSA-N 0.000 description 1
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- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- RITHLQKJQSKUAO-UHFFFAOYSA-N methyl 9,10-dihydroxyoctadecanoate Chemical compound CCCCCCCCC(O)C(O)CCCCCCCC(=O)OC RITHLQKJQSKUAO-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer 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
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229960001730 nitrous oxide Drugs 0.000 description 1
- 235000013842 nitrous oxide Nutrition 0.000 description 1
- KKVZAVRSVHUSPL-UHFFFAOYSA-N o-methoxycinnamic aldehyde Natural products COC1=CC=CC=C1C=CC=O KKVZAVRSVHUSPL-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-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
- 239000011087 paperboard Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000008096 xylene Substances 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
- 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
-
- 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)
Description
= 20014534
Ce
Substance for Bonding, Coating and Sealing, Consisting of
Cyanoacrylates and Aldehyde or Ketone Condensation Products
This invention relates to a bonding, coating and sealing composition based on a mixture of A) cyanoacrylates and B) condensation products of aldehydes and ketones.
Cyanoacrylates adhesive such as these are known. Thus, DE 43 17 886 describes a cyanoacrylate adhesive which, to reduce adhesion to the skin, contains 1 to 40% by weight of fatty derivatives in the form of certain aliphatic alcohols or certain aliphatic carboxylic acid esters. 10 to 100,000 ppm of an anionic polymerization accelerator are added to this mixture. A large number of substances are mentioned, including inter alia formaldehyde and acetaldehyde condensation products and ethers of polyalkylene oxides, for example with sorbitol as hydroxyi-containing compound. Polyoxyethylene sorbitan esters and polyoxyethylene/sorbitol addition products are specifically mentioned. In order to make the cyanoacrylate - a low-viscosity liquid - more viscous or thixotropic, a thickener, for example polymethyl methacrylate, acrylate rubber, cellulose derivative or silicate, is dissolved or dispersed. According to the Examples, the thickener is added in a quantity of 0 to 10% by weight. The disadvantage of this composition is that, even with a high concentration of thickener, the cyanoacrylate adhesive is liquid and, accordingly, cannot be used as a sealing compound, for example, or is unsuitable for bonding porous substrates and, quite generally, is difficult to apply.
Against the background of this prior art, the problem addressed by the present invention was to provide a cyanoacrylate composition with improved handling behavior which of course would exhibit at least usable, if not outstanding performance properties for bonding, coating and sealing ‘and, above all, adequate stability in storage at room temperature. In addition, production would be simple.
The solution provided by the invention is defined in the claims and consists essentially in the use of a gel former based on a condensation product of aldehydes and ketones with polyols for cyanoacrylates in order to produce compositions dimensionally stable at 20°C.
Dimensionally stable means that the composition does not change shape over a period of 10 days at 20°C solely under the effect of its own weight when the cylindrical composition is stored horizontally at 20°C in an open tube 1.5 cm in diameter and 5 cm in length; at least the stick then projects less than 10 mm and preferably less than 0.1 mm beyond the tube.
On the other hand, however, dimensional stability should also be only so great that, when a light external pressure is applied, the composition rubs off onto paper in the same way as commercially available adhesive sticks.
Suitable gel formers are certain condensation products of aldehydes or ketones with polyols.
Compounds containing at least one acetal or ketal group are used as gel formers. Such compounds can be obtained by condensation reactions and are also typically prepared, for example, by partial or complete dehydration of polyols with aldehydes or ketones in a ratio (OH: =
C =0) of 1:0.5 to 1:0.01 and preferably 1:0.5 to 1:0.1, for example in the presence of an acid as catalyst. The acetals and ketals according to the invention may also be prepared by reaction of the polyols with derivatives of the aldehydes or ketones, for example by reaction of geminal dichlorides with evolution of hydrogen chloride or acetals or ketals with elimination of alcohol. Suitable compounds have a melting point of at least 50°C, more particularly of at least 100°C and preferably of at least 150°C. Mixtures of the acetals and ketals may also be used.
Suitable polyols contain at least one 1,2-diol, 1,3-diol or 1,4-diol group. Other functional groups, for example ether, acid, ester, amide, cyano, hemiacetal and halide groups, may also be present. Examples of
® such polyols are ethane-1,2-diol, propane-1,3-diol, propane-1,2-diol, butane-2,3-diol, butane-1,4-diol, 2,2-dimethylpropane-1,3-diol, 2,2-bis- (hydroxymethy!)-propane-1,3-diol, 2-(bromomethyl)-2-(hydroxymethyl)- propane-1,3-diol, butane-1,3,4-triol, 1-phenylpropane-1,2,3-triol, hexane- 1,2-diol, neopentyl glycol, 1,4-bishydroxymethyl cyclohexane, 2- methylpropane-1,3-diol, hexane-1,2,6-triol, 2-(2-hydroxyethoxy)-butane- 1,3,4-triol, glycerol, di- and polyglycerol, diglycerol diacetate, trimethylol propane, di-(trimethylolpropane), trimethylol ethane, pentaerythritol, bicyclo[2.2.1]heptane-2,3,5,6-tetrol, 2,2,3,3-tetrahydroxybutanedioic acid, dipentaerythritol, sorbitol, formitol, xylitol, inositol, glucitol, glucose, sucrose, starch, cellulose, ascorbic acid, partly or completely hydrolyzed polyvinyl acetate, 9,10-dihydroxystearic acid methyl ester, diacetyl sorbitol and methyl glycoside.
Preferred polyols are sorbitol, xylitol and mannitol, more particularly sorbitol.
Suitable aldehydes or ketones contain at least one substituted or unsubstituted aromatic, heteroaromatic or alicyclic ring. Other functional groups, for example ether, ester, amide, cyano and halide groups, may also be present.
Examples of suitable ketones are cyclopentanone, cyclohexanone, cycloheptanone, 1-(3,3-dimethylcyciohexyl)-ethanone, 1- cyclopropylethanone, 3-methyl-5-propylcyclohex-2-en-1-one, dicyclopropyl methanone, 4-tert.butyl cyclohexanone, dicyclohexyl methanone, 4-methyl cyclohexanone, 1-(1-methylcyclopropyl)-ethanone, (4-chlorophenyl)- cyclopropyl methanone, 1-(1H-pyrrol-2-yl)-ethanone, 1-(2,4,6- trimethylphenyl)-ethanone, 1-(2-furanyl)-2-propanone, 1-(2-naphthalenyl)- ethanone, 1-(2-thienyl)-1-propanone, 1-(4-bromophenyl)-ethanone, 1-(4- methoxyphenyl)-ethanone, 1-(naphthalenyl}-ethanone, 1,1-diphenyl-2- propanone, 1,2-diphenyl ethanone, 1,3-diphenyl-2-propanone, 1-phenyl-1- butanone, 1-phenyl-1-decanone, 1-phenyl-1-dodecanone, 1-phenyl-1-
hexanone, 1-phenyl-1-octanone, 1-phenyl-1-pentanone, 1-phenyl-1- penten-3-one, 1-phenyl-1-tetradecanone, 1-phenyl-2-butanone, 1-phenyl-2- propanone, 1-pyrazinyl ethanone, 2,2,2-trifluoro-1-phenyl ethanone, 1-(2- furanyl)-ethanone, 1-(2-pyridinyl)-ethanone, 1-(2-thienyl)-ethanone, 4- chloro-1-(4-fluorophenyl)-1-butanone, 4-phenyl-2-butanone, 1-phenyl ethanone, bis-(2-hydroxyphenyl)}-methanone, bis-(4-chlorophenyl)- methanone, cyclopentyl phenyl methanone, cyclopropyl-(4-methoxy- phenyl)-methanone, cyclopropyl-(4-methylphenyl)-methanone, cyclopropyl- 2-thienyl methanone, cyclopropyl phenyl methanone, 1,5-diphenyl-1,4- pentadien-3-one, phenyl-2-pyridinyl methanone, 2-bromo-1-(4-nitrophenyl)- ethanone, 2-napthalenyl phenyl methanone, 3-chloro-1-phenyl-1- propanone, 4-(4-hydroxyphenyl)-2-butanone, 4-(4-methoxyphenyl)-3-buten- 2-one, 1-(4-pyridinyl)-ethanone, 1-(4-hydroxyphenyl)-ethanone, 1-phenyl-1- propanone, 4-phenyl-3-buten-2-one, diphenyl methanone, 1-phenyl-2- butanone, 1-phenyl-2-buten-1-one, bis-(4-methylphenyl)-methanone, 2- methyl-1-phenyl-1-propanone, 2-chloro-1-phenyl ethanone, cyclopropyl-(4- fluorophenyl)-methanone, 1-(p-methoxyphenyl)-2-propanone, cyclohexyl phenyl methanone and phenyl-(2-thienyl)}-methanone.
Examples of suitable aldehydes are benzaldehyde, 3- chlorobenzaldehyde, 4-chlorobenzaldehyde, 2,6-dichlorobenzaldehyde, 2,4-dinitrobenzaldehyde, 3,4-dichlorobenzaldehyde, 3-fluorobenzaldehyde, 4-bromobenzaldehyde, 2-methyi tetrahydrobenzaldehyde, tetrahydrobenzaldehyde, 2-methyl-5-isopropylcyclopentene-1-aldehyde, 2,2 4-trimethylcyclohexa-4,6-diene-1-aldehyde, 3(4)-methyl-1- propylcyclohexene-3-aldehyde, 1,3(4)-dimethyicyclohexene-3-aldehyde, 2- methyl-1-propylcyciohexene-3-aldehyde, 3-cyclohexene-1-aldehyde, 2,3,4,5,6-pentafluorobenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 4-tolyl acetaldehyde, 2-methylbenzaldehyde, 4-hydroxybenzaldehyde, 3-methyl benzaldehyde, 2-hydroxy-1-naphthaldehyde, 4-methylbenzaldehyde, 3,5- dimethoxy-4-hydroxybenzaldehyde, cinnamaldehyde, 3-nitrobenzaldehyde,
® 2-pentyicinnamaldehyde, 4-diethylaminobenzaldehyde, 4-methoxy- benzaldehyde, 2-phenylpropionaldehyde, 2-methoxycinnamaldehyde, 4- methylbenzaldehyde, phenoxyacetaldehyde, methylpyrrole-2-aldehyde, 2,5-dimethoxytetrahydrofuran-3-aldehyde, 2,5-dipropyl-3,4-dihydropyran-2- aldehyde, 2,5-diethyl-3,4-dihydropyran-2-aldehyde, 2,5-diisopropyl-3,4- dihydropyran-2-aldehyde, 2,5-dimethyl-3,4-dihydropyran-2-aldehyde, 2,5- dibutyl-3,4-dihydroypyran-2-aldehyde, thiophene-3-aldehyde, indole-3- aldehyde, thiophene-3-aldehyde, pyridine-3-aldehyde, pyridine-4-aldehyde and N-methylpyrrole-2-aldehyde.
Preferred aldehydes are benzaldehyde, 3-chlorobenzaldehyde and 3-fluorobenzaldehyde, more particularly benzaldehyde.
Examples of acetals and ketals according to the invention are di-O- benzylidene mannitol, di-O-(2-chlorobenzylidene)-mannitol, di-O-(4- nitrobenzylidene)-mannitol, di-O-(3-fluorobenzylidene)-mannitol, O- benzylidene sorbitol, di-O-benzylidene sorbitol diacetate, di-O-(2- chlorobenzylidene)-sorbitan diacetate, tri-O-(4-chlorobenzylidene)-sorbitol,
O-benzylidene threitol, O-benzylidene tartaric acid dimethyl ester, O- cyclohexylidene glycerol, O-cyclohexylidene ascorbic acid and O- benzylidene-9,10-dihydroxystearic acid methyl ester.
Preferred acetals and ketals are di-O-benzylidene mannitol, di-O-(3- fluorobenzylidene)-mannitol and di-O-benzylidene sorbitol, more particularly di-O-benzylidene sorbitol.
The percentage content of the aldehyde or ketone condensation products is 0.1 to 10% by weight, preferably 0.4 to 6% by weight and more particularly 1 to 3% by weight, based on the cyanoacrylate composition.
The cyanoacrylate composition is essentially based on typical cyanoacrylates, i.e. on monoacrylates and/or biscyanoacrylates. Their percentage content is at least 29.5% by weight and preferably at least 50% by weight, based on the cyanoacrylate compositions as a whole. “Typical monocyanoacrylic acid esters” in the context of the invention are understood to be compounds corresponding to general formula (1):
H.C = C(CN)-CO-O-R 0) where R is an alkyl, alkenyl, cycloalkyl, aryl, alkoxyalkyl, aralkyl or haloalkyl group with up to two conjugated C-C double bonds, with a cycloaliphatic 6- ring, with an aromatic nucleus derived from benzene and preferably with Br or Cl as halogen and containing 1 to 18 and preferably 2, 3 or 4 carbon atoms, more especially a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, pentyl, hexyl, cyclohexyl, heptyl, 2-ethylhexyl, n-octyl, n-nonyl, oxononyl, n-decyl, d-dodecyl, 2,2,2-trifluoroethyl, hexafluoroisopropyl, allyl, methallyl, crotyl, propargyl, benzyl, phenyl, cresyl, 2-chloroethyl, 3- chloropropyi, 2-chlorobutyl, tetrahydrofurfuryl, 2-methoxyethyl, butoxyethoxyethyl, 3-methoxybutyl and 2-ethoxyethyl group. The cyanoacrylates mentioned above are known to the expert on adhesives, cf.
Ullmann’s Encyclopedia of Industrial Chemistry, Vol. A1, page 240,
Verlag Chemie Weinheim (1985), US-PS 3,254,111. Preferred monomers are the allyl, methoxyethyl, ethoxyethyl, methyl, ethyl, propyl, isopropyl or butyl esters of 2-cyanoacrylic acid. “Biscyanoacrylates” are compounds corresponding to general formula (Il): [H2C = C(CN)-CO-OLR’ (an where R'is a branched or unbranched difunctional aikane group containing 2 to 18 and, more particularly, 6 to 12 carbon atoms which may also contain hetero atoms, such as halogens and oxygen, or aliphatic or aromatic rings. However, R' is preferably a pure hydrocarbon. It is important that the biscyanoacrylates be particularly pure. This requirement
@ is satisfied, for example, by the following production and purification . methods: essentially, monocyanoacrylates are transesterified with diols and the reaction mixtures are subsequently worked up by fractional crystallization.
Accordingly, a suitable process for the production of biscyanoacrylates comprises transesterifying 2-cyanoacrylic acid or an alkyl ester thereof corresponding to general formula (lll):
H,C = C(CN)-CO-0-R? (1) where R? is a branched or unbranched alkyl group containing 1 to 6 carbon atoms, with diols corresponding to general formula (IV): [HOLR' (IV) where R' is a branched or unbranched difunctional alkane group containing 2 to 18 carbon atoms, which may also contain hetero atoms, such as halogens and oxygen, or aliphatic or aromatic rings, to form biscyanoacrylates corresponding to general formula Il and then purifying the reaction mixture by fractional crystallization.
Accordingly, one starting product is a monofunctional cyanoacrylic acid corresponding to formula Ill or an alkyl ester thereof. The alkyl group should be selected so that the alcohol formed can be easily removed.
Suitable possibilities are known to the expert from the general transesterification reaction. The alcohol is preferably removed by distillation. Accordingly, R? is a branched or unbranched alcohol radical containing 1 to 6 carbon atoms, preferably 1 or 2 carbon atoms. The monofunctional cyanoacrylate is stabilized in the usual way.
The diols (formula IV) are dihydric primary or secondary alcohols,
® preferably primary alcohols. The hydroxyl groups may be in any position to one another, although they are preferably in the alpha/omega position.
The diols contain 2 to 18 carbon atoms and preferably 6 to 12 carbon atoms. They may be in a linear, branched or cyclic arrangement. The aliphatic radical may also contain an aromatic group or, besides the hydrogen and carbon atoms, hetero atoms such as, for example, chlorine or oxygen atoms, preferably in the form of polyethylene or polypropylene glycol units. Hexane diol, octane diol, decane diol and dodecane diol are specifically mentioned as diols.
The cyanoacrylate is used in excess. Accordingly, the molar ratio of monofunctional cyanoacrylate to diol is at least 2.0:1.0, preferably 2.5:1.0 and, more preferably, 2.2:1.0.
The transesterification is catalyzed by strong acids, more especially sulfonic acids and preferably aromatic sulfonic acids such as, for example, p-toluene sulfonic acid. However, naphthalene sulfonic acid, benzene sulfonic acid and acidic ion exchangers may also be used. The concentration of the transesterification catalyst should be between 1 and 20% by weight, based on the monofunctional cyanoacrylate.
The transesterification reaction is carried out in solution, as is normally the case. Suitable solvents are aromatic hydrocarbons and halogenated hydrocarbons. Preferred solvents are toluene and xylene.
The concentration of the solution is 10 to 50% and preferably 10 to 20%.
The monohydric alcohol formed and the water formed are removed in known manner and, preferably, distilled off with the solvent. The conversion of the transesterification reaction is monitored, for example, from NMR spectra. The reaction takes several hours, as is normally the case. Where toluene is used as the solvent and p-toluene sulfonic acid as the catalyst, the reaction is terminated after 10 to 15 hours when there is no further separation of alcohol.
The working up of the reaction mixture is very important. Where
® acidic ion exchangers are used as the catalyst, they may be simply filtered off. Where soluble sulfonic acids, for example p-toluene sulfonic acid, are used as the catalyst, they are removed by solvent substitution: toluene is replaced by a mixture of hexane, heptane or decane. Pure biscyanoacrylate is obtained after two fractional crystallizations. According to NMR spectra, it has a purity of more than 99%.
The biscyanoacrylate obtained is stable in storage with the usual stabilizers and in the usual concentrations, i.e. there is hardly any change in its melting point after storage for 6 months at 20°C.
However, the biscyanoacrylates obtained polymerize very quickly in the presence of bases, preferably at substantially the same rate as the corresponding monocyanoacrylates. As with the monofunctional cyano- acrylates, traces of water are sufficient. A three-dimensionally crosslinked polymer with relatively good thermal properties is formed.
According to the invention, therefore, it is used in known cyanoacrylate adhesives in a quantity of 0.5 to 50% by weight, preferably 1 to 10% by weight and more preferably 2 to 5% by weight, based on the cyanoacrylate composition as a whole.
It is known that cyanoacrylates are accessible both to anionic and to radical chain polymerization so that it is advisable to protect the ester compositions against both types of polymerization in order to prevent premature hardening of the ester, thereby avoiding difficulties in storage.
In order to prevent anionic polymerization, an anionic polymerization inhibitor may be added to the adhesives according to the invention. Any anionic polymerization inhibitors of the type hitherto used in cyanoacrylate adhesives are suitable for this purpose. For example, the anionic polymerization inhibitor may be an acidic gas, a protonic acid or an anhydride thereof. The preferred anionic polymerization inhibitor for the adhesives according to the invention is sulfur dioxide, preferably in a quantity of 0.001 to 0.5%, based on the adhesive. Other suitable anionic polymerization inhibitors are dinitrogen monoxide, hydrogen fluoride, hydrochloric acid, sulfuric acid, phosphoric acid, organic sulfonic and carboxylic acids and anhydrides thereof, phosphorus pentoxide and acid chlorides. In a preferred embodiment, a radical chain polymerization inhibitor is also added to the adhesives according to the invention in a quantity of 0.01 to 0.05% by weight. This radical chain polymerization inhibitor may be any one of the known radical chain polymerization inhibitors for cyanoacrylate compositions. Phenolic compounds, for example hydroquinone, t-butyl catequinone, pyrocatechol and p- methoxyphenol, are normally used. The above-mentioned commercially available ethyl 2-cyanoacrylate preparations are already stabilized. Should it be necessary to adjust the concentration of stabilizer where these commercially available preparations are used, this would present no difficulties to the expert.
In another preferred embodiment, polymers are also added to the cyanoacrylate compositions according to the invention, for example to increase their viscosity (thickeners) or to vary the adhesive properties. The polymers may be used in a quantity of 1 to 60% by weight, more particularly 10 to 50% by weight and preferably 10 to 30% by weight, based on the formulation as a whole. Suitable polymers are, above all, polymers based on vinyl ethers, vinyl esters, esters of acrylic acid and methacrylic acid containing 1 to 22 carbon atoms in the alcohol component, styrene or styrene co- and terpolymers with ethene, butadiene. Vinyl chloride/vinyl acetate copolymers with a vinyl chloride content of 50 to 95% by weight are preferred. The polymers may be present in liquid, resin-like or even in solid form. It is particularly important that the polymers contain no impurities from the polymerization process which could inhibit curing of the cyanoacrylate. If the polymers have too high a water content, they may have to be dried. The molecular weight (Mw) of the polymers may be scattered over a wide range but should be at least 1500 and at most
® 1,000,000 because otherwise the final viscosity of the adhesive formulation would be too high. Mixtures of the above-mentioned polymers may also be used. More particularly, a combination of low molecular weight and high molecular weight products has particular advantages in regard to the final viscosity of the adhesive formulation. Examples of suitable polymers based on vinyl acetate include Mowilith types 20, 30 and 60 and Vinnapas types B1.5, B100, B17, B5, B500/20VL, B60, UW10, UW1, UW30, UwW4 and UW50. Examples of suitable acrylate-based polymers are Acronal 4F and Laromer types 8912, PE5S55F and PO33F. Examples of suitable methacrylate-based polymers include Elvacite 2042, Neocryl types B 724,
B999 731, B 735, B 811, B 813, B 817 and B722, Plexidon MW 134,
Plexigum types M 825, M 527, N 742, N 80, P 24, P28 and PQ 610. An example of a suitable vinyl ether-based polymer is Lutonal A25. Cellulose derivatives and silica gel may aiso be used for thickening. The addition of polycyanoacrylates is particularly emphasized.
In addition, the cyanoacrylate composition according to the invention may contain other auxiliaries to obtain certain effects commensurate with the application envisaged. These other auxiliaries include above all the polymerization accelerators described in DE 43 17 886, i.e. polyalkylene oxides and derivatives thereof, particularly esters and ethers. Other polymerization accelerators are CROWN ETHERS and derivatives thereof, silica-crown compounds and cyclosulfur compounds. These polymerization accelerators are known to be added in a quantity of 10 to 100,000 ppm and more particularly in a quantity of 30 to 10,000 ppm, based on the cyanoacrylate composition. Another accelerator is cyclodextrin.
The fatty derivatives described in DE 197 52 893 and in DE 43 17 886 may also be used as plasticizers. These are fats and fatty derivatives, more particularly aliphatic alcohols, aliphatic carboxylic acid esters and carboxylic acid esters of a carbocyclic compound. Further information can be found in the patents cited above. The usual plasticizers, for example phthalates, citric acid esters, chloroparaffin and trimellitic acid esters, may of course also be used.
Solvents may also be added, in particular to increase the solubility of the aldehyde or ketone condensation product or to enable this product to be incorporated more easily in the form of a solution. Suitable organic solvents are, for example, alcohols, ethers, ketones and alkyl esters of low molecular weight. Particularly suitable organic solvents are isopropanol, methoxypropanol, ethoxypropanol, ethoxyethanol, propoxyethanol, butoxy- ethanol, methyl ethyl ketone and N-methyl-2-pyrrolidone. However, the content of solvents in the cyanoacrylate composition should be low in order not to jeopardize dimensional stability and is preferably less than 20% by weight.
Other auxiliaries are activators, dyes, pigments, fragrances, preservatives, antiseptics and fillers.
The cyanoacrylate composition according to the invention is produced essentially by dissolving the cyanoacrylates and the aldehyde or ketone condensation products with a polyol by heating and then hardening the resulting solution by cooling. In general, a stabilized cyanoacrylate composition is first prepared from an acrylate and an anionic polymerization inhibitor under nitrogen as an inert gas and is then heated to 50 to 90°C. The required components are then dissolved or suspended with intensive stirring untii a homogeneous mixture is obtained. The condensation product is then added in portions at 80 to 95°C and largely dissolved at 90 to 95°C. The mixture is then cooled, preferably to ca. 80°C, and poured into the required molds. After ca. 1 hour, the composition is generally hard and, after ca. 24 hours, is dimensionally stable enough for use as an adhesive stick. Despite its dimensional stability, the cyanoacrylate composition can be rubbed under light pressure onto a substrate, for example paper.
By virtue of its dimensional stability, the cyanoacrylate composition is suitable for conversion into a geometric shape, above all into a stick.
Adhesive sticks are preferably produced in cylindrical form. The particular shape is preferably adapted to the application envisaged. However, any shapes are possible, particularly geometric shapes with at least one plane or axis of symmetry, for example spheres, squares, pyramids, cones, cylinders, sticks, tapes, flakes, films and “pillows”. The shape is preferably smaller in two dimensions than in the third. Such shapes are, for example, sticks (hotmelt sticks) or “refills” in the form of wax sticks. The base or the geometric element may be angular, especially triangular, rectangular or hexagonal, or round (for example circular or elliptical). The diameter may be from 2 to 100 mm and the length up to 150 mm. Accordingly, the shape and quantity of the cyanoacrylate compositions according to the invention are highly variable and are largely determined by what is convenient for the particular application envisaged.
Liquid cyanoacrylate compositions with highly thixotropic properties can be produced by shearing of the ready-to-use cyanoacrylate composition at high rotational speeds. The cyanoacrylate compositions according to the invention are suitable for bonding, coating and sealing, more particularly for bonding porous substrates such as, for example, leather, textiles, paper, paperboard, cardboard, wood and skin. By virtue of their stick form, the cyanoacrylate compositions according to the invention may be used with particular advantage as an adhesive for repairing shoes, for PVC pipes and for artificial finger nails. The “gluing” of wounds, particularly where relatively long-chain cyanoacrylates are used, is also possible. In conjunction with primers, for example aliphatic amines, polyolefins can also be firmly bonded. The primers can also be converted into stick form with the gel formers according to the invention. Coloring and correcting sticks can also be produced by adding covering pigments and/or dyes. Through the absence of solvents, such sticks are particularly environment-friendly. In portioned form, the cyanoacrylate compositions according to the invention may also be used as filling material for filling cracks and holes in various materials. Both substrates are preferably coated with the adhesive, for example by rubbing with an adhesive stick.
Gap-filling bonds are also possible.
Where the cyanoacrylate compositions are used for sealing, their rapid curing rate is worth mentioning.
Surprisingly, the cyanoacrylate composition according to the invention is extremely stable in storage. For example, in conventional adhesive stick tubes, it could be stored and handled for many weeks at room temperature without any reduction in its adhesive strength.
Other advantages of the cyanoacrylate composition according to the invention include simple application, safe handling (no spattering, for example into the eyes or onto the skin), application over large areas, bonding of vertical substrates.
The invention is illustrated by the following Examples.
After 6 months at 2 to 5°C, the adhesive sticks were still usable, i.e. their consistency and adhesive properties were good. After 9 months at -18°C, the adhesive sticks were again still usable, i.e. no destruction of the gel structure and no polymer formation were observed. After heating to 20°C, the closure caps were easy to remove from the tubes. In tests with paper, the setting time and adhesive strength were virtually unchanged (paper tears). The stability in storage at -18°C of more than 9 months is important above all for medical applications.
Examples 1. Production of cyanoacrylate compositions
The stabilized cyanoacrylate was introduced under nitrogen into a three-necked flask and polymethacrylate was added in portions with intensive stirring at 50°C. After 10 minutes, the solution was clear and
EE homogeneous.
To form a gel, the temperature was increased to 85°C and dibenzylidene sorbital was added in portions to avoid the formation of lumps. After 10 minutes, the gelling agent was largely dissolved. After cooling to around 80°C, undissolved particles were removed by filtration.
The solution was poured while still hot into conventional adhesive stick tubes and then cooled. After ca. 1 hour, the consistency was solid. The next day the adhesive stick was ready-to-use and remained stable for several weeks despite repeated closing and opening. 2. Tests a) To test stability in storage, a cyanoacrylate composition in an adhesive stick tube was tested weekly for its adhesiveness on paper at 23°C/50% relative air humidity. b) To determine setting time, the cyanoacrylate composition was applied to one side of a 30 cm long paper strip and, immediately afterwards, a second strip of paper was applied and pressed down.
The time elapsing before the paper tore on separation of the adhesive bond was measured. «c©) To determine the tensile shear strength of longitudinal bonds, a) two drops of the liquid adhesive were applied to a 10 x 25 mm area of the substrate or b) a comparable quantity was applied to one side by rubbing with the adhesive stick. Immediately afterwards, the second substrate was lightly pressed on. After 2 days at 23°C/50% relative air humidity, the beechwood and also the non-wood specimens were tested for tensile shear strength (rate: 10 mm/min.) in accordance with EN 205.
The results were expressed as the averages of 5 measurements.
The substrates were pretreated as follows: - beechwood, untreated
. @ = A - PMMA: degreased - ABS plastic: degreased - PVC: degreased and - Alu: sandblasted and degreased. 3. Results
The test results are set out in Table 1. They show that useful strengths were obtained in every case, exceeding the strengths of conventional cyanoacrylate adhesives in the case of beechwood.
Table 1. Composition (in parts by weight) and properties of cyanoacrylate compositions 0 EE
Compositions Li. 1. Ethyl cyanoacrylate 100 100 2. SOz + + 3. Phosphoric acid, methanesulfonic acid + + 4. Polymethacylate 5 5 5. Dibenzylidene sorbital 0 1.8
Il Properties a) Storage stability [weeks] - >10 b) Setting time [seconds] No bond 20 c) Tensile shear strength [MP3] - beechwood 7.33 TA 7.75 - PMMA 7.01 MF 6.11 MF - ABS plastic 8.10 MF 6.21 part. MF - aluminium 14.75 7.08 -PVC 14.59 MF 4.90 MF v WO 00/32709 17 PCT/EP99/09287
TA = tearing of material
MF = material failure part. MF = material failure in some test specimens
Claims (13)
1. A cyanoacrylate adhesive, coating and sealing composition based on a mixture of A) at least one cyanoacrylate and B) at least one aldehyde or ketone condensation product with a polyol.
2. A composition as claimed in claim 1, characterized by at least one substance from the following group of aldehydes or ketones: benzaldehyde, 3-chlorobenzaldehyde and 3-fluorobenzaldehyde, more particularly benzaldehyde.
3. A composition as claimed in claim 1, characterized by at least one substance from the following group of polyols: sorbitol, xylitol and mannitol, more particularly sorbitol.
4. A composition as claimed in claim 1, characterized by at least one substance from the following group of aldehyde or ketone condensation products with polyols: di-O-benzylidene mannitol, di-O-(3- fluorobenzylidene)-mannitol and di-O-benzylidene sorbitol, more particularly di-O-benzylidene sorbitol.
5. A composition as claimed in claim 1, characterized by the following composition (based on the cyanoacrylate composition as a whole): A) 99.8 to 29.5% by weight of at least one cyanoacrylate and B) 0.1 to 10% by weight of at least one aldehyde or ketone condensation product with a polyol and C) 0.001 to 0.5% by weight of stabilizers, D) 0 to 60% by weight of thickeners, solvents, plasticizers, fillers and other auxiliaries.
6. A composition as claimed in claim 1, characterized by a geometric form, more particularly a stick form.
7. A process for the production of the composition claimed in at least one of claims 1 to 6, characterized in that a solution is first prepared from components A) and B) by heating and is then cooled.
PCT/EP99/09287
8. The use of the compositions claimed in at least one of claims 1 to 6 for bonding, coating and sealing.
9. The use claimed in claim 8 for bonding porous substrates.
10. A composition as claimed in claim 1, substantially as herein described and illustrated.
11. A process as claimed in claim 7, substantially as herein described and illustrated.
12. A use as claimed in claim 8, substantially as herein described and illustrated.
13. A new composition, a new process for the production of a composition, or a new use of a composition as claimed in any one of claims 1 to 6, substantially as herein described. AMENDED SHEET
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19855272 | 1998-12-02 |
Publications (1)
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ZA200104538B true ZA200104538B (en) | 2002-09-02 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200104538A ZA200104538B (en) | 1998-12-02 | 2001-06-01 | Substance for bonding, coating and sealing, consisting of cyanoacrylates and aldehyde or ketone condensation products. |
Country Status (19)
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EP (1) | EP1159362A1 (en) |
JP (1) | JP2002531629A (en) |
KR (1) | KR20010107993A (en) |
CN (1) | CN1329648A (en) |
AU (1) | AU770134B2 (en) |
BR (1) | BR9915814A (en) |
CA (1) | CA2353605A1 (en) |
CZ (1) | CZ20011972A3 (en) |
DE (1) | DE19957677A1 (en) |
HU (1) | HUP0104526A3 (en) |
ID (1) | ID30447A (en) |
NO (1) | NO20012717D0 (en) |
PL (1) | PL348719A1 (en) |
RU (1) | RU2238292C2 (en) |
SK (1) | SK7432001A3 (en) |
TR (1) | TR200101471T2 (en) |
UA (1) | UA73930C2 (en) |
WO (1) | WO2000032709A1 (en) |
ZA (1) | ZA200104538B (en) |
Families Citing this family (23)
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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 (en) * | 2004-01-09 | 2005-08-04 | Henkel Kgaa | Gap bridging cyanoacrylate adhesive |
US8192731B2 (en) | 2005-10-25 | 2012-06-05 | Loctite (R&D) Limited | Thickened cyanoacrylate compositions |
ATE441685T1 (en) * | 2007-06-15 | 2009-09-15 | Max Planck Ges Zur Firderung D | METHOD FOR PRODUCING ORGANIC POROUS SOLID BODY AND SOLID BODY THAT CAN BE PRODUCED BY THIS METHOD |
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 (en) | 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 | Biodegradable medical adhesive, and preparation method and purpose thereof |
CN105419430A (en) * | 2015-11-24 | 2016-03-23 | 丹阳镇威汽配有限公司 | Coating for rain wiper contact surface of wiper blade and preparing method thereof |
WO2018022788A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
EP3491079B1 (en) | 2016-07-26 | 2023-06-07 | PPG Industries Ohio, Inc. | Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds |
EP4151689A1 (en) * | 2016-07-26 | 2023-03-22 | PPG Industries Ohio, Inc. | Curable 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 |
ES2957658T3 (en) | 2016-07-26 | 2024-01-23 | Ppg Ind Ohio Inc | Polyurethane coating compositions containing 1,1-diactivated vinyl compounds and related coatings and processes |
CN109476081B (en) | 2016-07-26 | 2021-11-23 | Ppg工业俄亥俄公司 | Three-dimensional printing method using 1,1-di activated vinyl compound |
ES2930531T3 (en) | 2016-07-26 | 2022-12-16 | Ppg Ind Ohio Inc | Particles having surfaces functionalized with 1,1-diactivated vinyl compounds |
CN109475903B (en) | 2016-07-26 | 2021-11-26 | Ppg工业俄亥俄公司 | Multilayer curable compositions containing 1, 1-di activated vinyl compound products and related 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 |
CN107442381B (en) * | 2017-09-01 | 2021-03-30 | 山东华成中德传动设备有限公司 | Surface treatment method of wood mold |
GB2567220B (en) | 2017-10-06 | 2021-01-27 | Henkel IP & Holding GmbH | Solid cyanoacrylate compositions comprising thermoplastic polyurethane |
CN112279999B (en) * | 2020-11-09 | 2022-03-11 | 广东石油化工学院 | Biodegradable radiation-curable urethane (meth) acrylate and preparation method thereof |
CN112322196A (en) * | 2020-11-24 | 2021-02-05 | 山东禹王和天下新材料有限公司 | Adhesive for rapid bonding of polystyrene foam material and preparation method thereof |
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US3846363A (en) * | 1971-02-03 | 1974-11-05 | Nippon Synthetic Chem Ind | Adhesive crayon composition containing sorbitol-benzaldehyde reaction product as additive |
JPS49104931A (en) * | 1973-02-05 | 1974-10-04 | ||
JPS54107993A (en) * | 1978-02-10 | 1979-08-24 | Matsumoto Seiyaku Kogyo Kk | Alphaacyanoacrylate composition |
-
1999
- 1999-11-30 BR BR9915814-0A patent/BR9915814A/en not_active Application Discontinuation
- 1999-11-30 DE DE19957677A patent/DE19957677A1/en not_active Ceased
- 1999-11-30 CN CN99813954A patent/CN1329648A/en active Pending
- 1999-11-30 CZ CZ20011972A patent/CZ20011972A3/en unknown
- 1999-11-30 TR TR2001/01471T patent/TR200101471T2/en unknown
- 1999-11-30 HU HU0104526A patent/HUP0104526A3/en unknown
- 1999-11-30 WO PCT/EP1999/009287 patent/WO2000032709A1/en not_active Application Discontinuation
- 1999-11-30 SK SK743-2001A patent/SK7432001A3/en unknown
- 1999-11-30 ID IDW00200101450A patent/ID30447A/en unknown
- 1999-11-30 RU RU2001118044/04A patent/RU2238292C2/en not_active IP Right Cessation
- 1999-11-30 KR KR1020017006731A patent/KR20010107993A/en active IP Right Grant
- 1999-11-30 UA UA2001064524A patent/UA73930C2/en unknown
- 1999-11-30 JP JP2000585342A patent/JP2002531629A/en active Pending
- 1999-11-30 AU AU17785/00A patent/AU770134B2/en not_active Ceased
- 1999-11-30 PL PL99348719A patent/PL348719A1/en not_active Application Discontinuation
- 1999-11-30 CA CA002353605A patent/CA2353605A1/en not_active Abandoned
- 1999-11-30 EP EP99961028A patent/EP1159362A1/en not_active Withdrawn
-
2001
- 2001-06-01 ZA ZA200104538A patent/ZA200104538B/en unknown
- 2001-06-01 NO NO20012717A patent/NO20012717D0/en not_active Application Discontinuation
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NO20012717L (en) | 2001-06-01 |
RU2238292C2 (en) | 2004-10-20 |
SK7432001A3 (en) | 2002-01-07 |
CN1329648A (en) | 2002-01-02 |
PL348719A1 (en) | 2002-06-03 |
KR20010107993A (en) | 2001-12-07 |
TR200101471T2 (en) | 2001-11-21 |
HUP0104526A3 (en) | 2003-07-28 |
AU1778500A (en) | 2000-06-19 |
HUP0104526A2 (en) | 2002-03-28 |
BR9915814A (en) | 2001-08-21 |
ID30447A (en) | 2001-12-06 |
DE19957677A1 (en) | 2000-06-08 |
CA2353605A1 (en) | 2000-06-08 |
WO2000032709A1 (en) | 2000-06-08 |
EP1159362A1 (en) | 2001-12-05 |
CZ20011972A3 (en) | 2001-11-14 |
JP2002531629A (en) | 2002-09-24 |
UA73930C2 (en) | 2005-10-17 |
NO20012717D0 (en) | 2001-06-01 |
AU770134B2 (en) | 2004-02-12 |
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