DE19957677A1 - Masse zum Verkleben, Beschichten und Dichten aus Cyanacrylaten und Aldehyd- bzw. Keton-Kondensationsprodukten - Google Patents
Masse zum Verkleben, Beschichten und Dichten aus Cyanacrylaten und Aldehyd- bzw. Keton-KondensationsproduktenInfo
- Publication number
- DE19957677A1 DE19957677A1 DE19957677A DE19957677A DE19957677A1 DE 19957677 A1 DE19957677 A1 DE 19957677A1 DE 19957677 A DE19957677 A DE 19957677A DE 19957677 A DE19957677 A DE 19957677A DE 19957677 A1 DE19957677 A1 DE 19957677A1
- Authority
- DE
- Germany
- Prior art keywords
- cyanoacrylate
- aldehyde
- mass
- polyol
- coating
- 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 abstract description 40
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 17
- 150000002576 ketones Chemical class 0.000 title claims abstract description 17
- 229920005862 polyol Polymers 0.000 title claims abstract description 14
- 150000003077 polyols Chemical class 0.000 title claims abstract description 14
- 239000007859 condensation product Substances 0.000 title claims abstract description 13
- 239000011248 coating agent Substances 0.000 title claims abstract description 7
- 238000000576 coating method Methods 0.000 title claims abstract description 7
- 239000000758 substrate Substances 0.000 title claims description 9
- 239000003566 sealing material Substances 0.000 title abstract 2
- 239000004830 Super Glue Substances 0.000 title description 5
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- -1 3-fluorobenzylidene Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 29
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 12
- 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 10
- 239000000600 sorbitol Substances 0.000 claims description 10
- 235000010356 sorbitol Nutrition 0.000 claims description 10
- 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 9
- 239000002904 solvent Substances 0.000 claims description 9
- 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 7
- 229930195725 Mannitol Natural products 0.000 claims description 7
- 238000004026 adhesive bonding Methods 0.000 claims description 7
- 239000000594 mannitol Substances 0.000 claims description 7
- 235000010355 mannitol Nutrition 0.000 claims description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 4
- 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
- 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
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 abstract description 17
- 239000000853 adhesive Substances 0.000 abstract description 15
- 238000001816 cooling Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 13
- 239000004836 Glue Stick Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000123 paper Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N Anisaldehyde Natural products COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 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
- 241001070947 Fagus Species 0.000 description 3
- 235000010099 Fagus sylvatica Nutrition 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
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 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
- 238000002360 preparation method Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000012360 testing method Methods 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
- 239000001431 2-methylbenzaldehyde Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-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
- 238000005299 abrasion Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 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
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [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
- 239000011111 cardboard Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 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
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- 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
- FDGCNGPUZIIRQI-UHFFFAOYSA-N (4-methoxyphenyl)methanone Chemical compound O(C1=CC=C([C-]=O)C=C1)C FDGCNGPUZIIRQI-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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- 229940015975 1,2-hexanediol Drugs 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 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
- DXIWBWIDAYBUDF-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanone Chemical compound CC(=O)C1CCCC(C)(C)C1 DXIWBWIDAYBUDF-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
- BNKHRJHKRBYDTL-UHFFFAOYSA-N 1-ethylcyclohex-2-ene-1-carbaldehyde Chemical compound CCC1(C=O)CCCC=C1 BNKHRJHKRBYDTL-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
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 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
- 238000011835 investigation Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- SJNXJRVDSTZUFB-UHFFFAOYSA-N naphthalen-2-yl(phenyl)methanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C1=CC=CC=C1 SJNXJRVDSTZUFB-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 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
- 239000003960 organic solvent Substances 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 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
- DWYFUJJWTRPARQ-UHFFFAOYSA-N phenyl(thiophen-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CS1 DWYFUJJWTRPARQ-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
- 229920000166 polytrimethylene carbonate 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
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 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
- 150000003254 radicals Chemical group 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
- 230000008439 repair process 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
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 230000007306 turnover Effects 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
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19957677A DE19957677A1 (de) | 1998-12-02 | 1999-11-30 | Masse zum Verkleben, Beschichten und Dichten aus Cyanacrylaten und Aldehyd- bzw. Keton-Kondensationsprodukten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19855272 | 1998-12-02 | ||
| DE19957677A DE19957677A1 (de) | 1998-12-02 | 1999-11-30 | Masse zum Verkleben, Beschichten und Dichten aus Cyanacrylaten und Aldehyd- bzw. Keton-Kondensationsprodukten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19957677A1 true DE19957677A1 (de) | 2000-06-08 |
Family
ID=7889544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19957677A Ceased DE19957677A1 (de) | 1998-12-02 | 1999-11-30 | Masse zum Verkleben, Beschichten und Dichten aus Cyanacrylaten und Aldehyd- bzw. Keton-Kondensationsprodukten |
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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828291B2 (en) | 2000-05-31 | 2004-12-07 | Loctite (R&D) Limited | Semi-solid compositions for removing cured product |
| US8192731B2 (en) | 2005-10-25 | 2012-06-05 | Loctite (R&D) Limited | Thickened cyanoacrylate compositions |
| US9457613B2 (en) | 2008-09-26 | 2016-10-04 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| US11066507B2 (en) | 2017-10-06 | 2021-07-20 | Henkel IP & Holding GmbH | Solid cyanoacrylate compositions |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE602007002294D1 (de) * | 2007-06-15 | 2009-10-15 | Max Planck Gesellschaft | Verfahren zur Herstellung organischer poröser Festkörper und mit diesem Verfahren herstellbare Festkörper |
| GB2463065B (en) | 2008-09-01 | 2012-11-07 | Loctite R & D Ltd | Transferable curable non-liquid film on a release substrate |
| CN102197102B (zh) * | 2008-09-26 | 2014-11-26 | 汉高公司 | 不可流动形式的氰基丙烯酸酯组合物 |
| 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 |
| WO2018022804A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Multi-layer curable compositions containing 1,1-di-activated vinyl compound products and related processes |
| WO2018022792A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds |
| ES2957658T3 (es) | 2016-07-26 | 2024-01-23 | Ppg Ind Ohio Inc | Composiciones de recubrimiento de poliuretano que contienen compuestos vinílicos 1,1-diactivados y recubrimientos y procesos relacionados |
| 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 |
| US11613076B2 (en) | 2016-07-26 | 2023-03-28 | Ppg Industries Ohio, Inc. | Three-dimensional printing processes using 1,1-di-activated vinyl compounds |
| US11466159B2 (en) | 2016-07-26 | 2022-10-11 | Ppg Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
| ES2932518T3 (es) * | 2016-07-26 | 2023-01-20 | Ppg Ind Ohio Inc | Composiciones curables que contienen compuestos vinílicos 1,1-diactivados y recubrimientos y procesos relacionados |
| 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 |
| 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 |
| 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 |
Family Cites Families (5)
| 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 |
| JPS49104931A (cs) * | 1973-02-05 | 1974-10-04 | ||
| JPS54107993A (en) * | 1978-02-10 | 1979-08-24 | Matsumoto Seiyaku Kogyo Kk | Alphaacyanoacrylate composition |
| 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 CZ CZ20011972A patent/CZ20011972A3/cs unknown
- 1999-11-30 CN CN99813954A patent/CN1329648A/zh active Pending
- 1999-11-30 KR KR1020017006731A patent/KR20010107993A/ko not_active Abandoned
- 1999-11-30 ID IDW00200101450A patent/ID30447A/id unknown
- 1999-11-30 SK SK743-2001A patent/SK7432001A3/sk unknown
- 1999-11-30 PL PL99348719A patent/PL348719A1/xx not_active Application Discontinuation
- 1999-11-30 HU HU0104526A patent/HUP0104526A3/hu unknown
- 1999-11-30 CA CA002353605A patent/CA2353605A1/en not_active Abandoned
- 1999-11-30 EP EP99961028A patent/EP1159362A1/de not_active Withdrawn
- 1999-11-30 DE DE19957677A patent/DE19957677A1/de not_active Ceased
- 1999-11-30 RU RU2001118044/04A patent/RU2238292C2/ru not_active IP Right Cessation
- 1999-11-30 WO PCT/EP1999/009287 patent/WO2000032709A1/de not_active Ceased
- 1999-11-30 BR BR9915814-0A patent/BR9915814A/pt not_active Application Discontinuation
- 1999-11-30 JP JP2000585342A patent/JP2002531629A/ja active Pending
- 1999-11-30 UA UA2001064524A patent/UA73930C2/uk unknown
- 1999-11-30 TR TR2001/01471T patent/TR200101471T2/xx unknown
- 1999-11-30 AU AU17785/00A patent/AU770134B2/en not_active Ceased
-
2001
- 2001-06-01 NO NO20012717A patent/NO20012717L/no not_active Application Discontinuation
- 2001-06-01 ZA ZA200104538A patent/ZA200104538B/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828291B2 (en) | 2000-05-31 | 2004-12-07 | Loctite (R&D) Limited | Semi-solid compositions for removing cured product |
| US8192731B2 (en) | 2005-10-25 | 2012-06-05 | Loctite (R&D) Limited | Thickened cyanoacrylate compositions |
| US9457613B2 (en) | 2008-09-26 | 2016-10-04 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| US9828529B2 (en) | 2008-09-26 | 2017-11-28 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| US11066507B2 (en) | 2017-10-06 | 2021-07-20 | Henkel IP & Holding GmbH | Solid cyanoacrylate compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2353605A1 (en) | 2000-06-08 |
| ZA200104538B (en) | 2002-09-02 |
| SK7432001A3 (en) | 2002-01-07 |
| EP1159362A1 (de) | 2001-12-05 |
| JP2002531629A (ja) | 2002-09-24 |
| TR200101471T2 (tr) | 2001-11-21 |
| WO2000032709A1 (de) | 2000-06-08 |
| PL348719A1 (en) | 2002-06-03 |
| ID30447A (id) | 2001-12-06 |
| BR9915814A (pt) | 2001-08-21 |
| NO20012717D0 (no) | 2001-06-01 |
| AU1778500A (en) | 2000-06-19 |
| HUP0104526A3 (en) | 2003-07-28 |
| RU2238292C2 (ru) | 2004-10-20 |
| CZ20011972A3 (cs) | 2001-11-14 |
| AU770134B2 (en) | 2004-02-12 |
| UA73930C2 (en) | 2005-10-17 |
| KR20010107993A (ko) | 2001-12-07 |
| NO20012717L (no) | 2001-06-01 |
| CN1329648A (zh) | 2002-01-02 |
| HUP0104526A2 (hu) | 2002-03-28 |
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| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: HENKEL AG & CO. KGAA, 40589 DUESSELDORF, DE |
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| 8131 | Rejection |