UA73930C2 - Cyanoacrylate bulk for bonding, coating application and sealing - Google Patents

Cyanoacrylate bulk for bonding, coating application and sealing Download PDF

Info

Publication number: UA73930C2
Authority: UA; Ukraine
Prior art keywords: cyanoacrylate; mass; acid; differs; phenyl
Prior art date: 1998-12-02

Application number

UA2001064524A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Henkel Kgaa

Priority date (The priority date 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 date listed.)

1998-12-02

Filing date

1999-11-30

Publication date

2005-10-17

1999-11-30 Application filed by Henkel Kgaa filed Critical Henkel Kgaa

2005-10-17 Publication of UA73930C2 publication Critical patent/UA73930C2/uk

Links

229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 51
238000007789 sealing Methods 0.000 title claims abstract description 7
239000011248 coating agent Substances 0.000 title claims abstract description 5
238000000576 coating method Methods 0.000 title claims abstract description 5
MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims description 42
239000007859 condensation product Substances 0.000 claims abstract description 11
229920005862 polyol Polymers 0.000 claims abstract 4
150000003077 polyols Chemical class 0.000 claims abstract 4
229920000642 polymer Polymers 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 11
238000004026 adhesive bonding Methods 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
239000000047 product Substances 0.000 claims description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
229920001577 copolymer Polymers 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
229920001897 terpolymer Polymers 0.000 claims description 2
150000003934 aromatic aldehydes Chemical class 0.000 claims 3
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 15
230000001070 adhesive effect Effects 0.000 abstract description 13
150000002576 ketones Chemical class 0.000 abstract description 13
150000001299 aldehydes Chemical class 0.000 abstract description 12
239000000853 adhesive Substances 0.000 abstract description 11
NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 abstract description 10
239000000758 substrate Substances 0.000 abstract description 9
239000002023 wood Substances 0.000 abstract description 6
238000003860 storage Methods 0.000 abstract description 4
239000004836 Glue Stick Substances 0.000 abstract 1
-1 aliphatic alcohols Chemical class 0.000 description 31
239000003292 glue Substances 0.000 description 15
150000001875 compounds Chemical class 0.000 description 12
239000002253 acid Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 10
IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 9
238000010539 anionic addition polymerization reaction Methods 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
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 description 7
150000002009 diols Chemical class 0.000 description 7
239000000600 sorbitol Substances 0.000 description 7
235000010356 sorbitol Nutrition 0.000 description 7
150000005846 sugar alcohols Polymers 0.000 description 7
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 description 6
150000001241 acetals Chemical group 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 6
239000002562 thickening agent 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
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 description 5
229930195725 Mannitol Natural products 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000594 mannitol Substances 0.000 description 5
235000010355 mannitol Nutrition 0.000 description 5
238000005809 transesterification reaction Methods 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000003925 fat Substances 0.000 description 4
239000003349 gelling agent Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000001431 2-methylbenzaldehyde Substances 0.000 description 3
241001070947 Fagus Species 0.000 description 3
235000010099 Fagus sylvatica Nutrition 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
239000000654 additive Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000005215 alkyl ethers Chemical class 0.000 description 3
239000007789 gas 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
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
239000004926 polymethyl methacrylate Substances 0.000 description 3
150000003254 radicals Chemical group 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
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 2
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 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
VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-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
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
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
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
150000007513 acids Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 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
150000001735 carboxylic acids Chemical class 0.000 description 2
239000011111 cardboard Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 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
230000006378 damage Effects 0.000 description 2
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000004820 halides Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000010985 leather Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 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
239000004014 plasticizer Substances 0.000 description 2
229920000233 poly(alkylene oxides) Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003138 primary alcohols Chemical class 0.000 description 2
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 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
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
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
150000000190 1,4-diols Chemical group 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
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
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 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
MAHPVQDVMLWUAG-UHFFFAOYSA-N 1-phenylhexan-1-one Chemical compound CCCCCC(=O)C1=CC=CC=C1 MAHPVQDVMLWUAG-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
CCFAGRVEHSCROQ-UHFFFAOYSA-N 1-phenylpropane-1,2,3-triol Chemical compound OCC(O)C(O)C1=CC=CC=C1 CCFAGRVEHSCROQ-UHFFFAOYSA-N 0.000 description 1
LXUIUVLDNRQBQJ-UHFFFAOYSA-N 1-phenyltetradecan-1-one Chemical compound CCCCCCCCCCCCCC(=O)C1=CC=CC=C1 LXUIUVLDNRQBQJ-UHFFFAOYSA-N 0.000 description 1
WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
QJXCFMJTJYCLFG-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzaldehyde Chemical compound FC1=C(F)C(F)=C(C=O)C(F)=C1F QJXCFMJTJYCLFG-UHFFFAOYSA-N 0.000 description 1
ZILXIZUBLXVYPI-UHFFFAOYSA-N 2,4-dinitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C([N+]([O-])=O)=C1 ZILXIZUBLXVYPI-UHFFFAOYSA-N 0.000 description 1
UIGLVRAGMWMVFU-UHFFFAOYSA-N 2,5-di(propan-2-yl)-3,4-dihydropyran-2-carbaldehyde Chemical compound CC(C)C1=COC(C(C)C)(C=O)CC1 UIGLVRAGMWMVFU-UHFFFAOYSA-N 0.000 description 1
TWEAKWNKZAGMDU-UHFFFAOYSA-N 2,5-dibutyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CCCCC1=COC(CCCC)(C=O)CC1 TWEAKWNKZAGMDU-UHFFFAOYSA-N 0.000 description 1
SQZVYXOKAXPDKY-UHFFFAOYSA-N 2,5-diethyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CCC1=COC(CC)(C=O)CC1 SQZVYXOKAXPDKY-UHFFFAOYSA-N 0.000 description 1
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229920001451 polypropylene glycol Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 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
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
230000001105 regulatory effect 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
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000003756 stirring Methods 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
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
239000004753 textile Substances 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
230000009466 transformation Effects 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
229960002675 xylitol Drugs 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)

UA2001064524A 1998-12-02 1999-11-30 Cyanoacrylate bulk for bonding, coating application and sealing UA73930C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19855272		1998-12-02
PCT/EP1999/009287 WO2000032709A1 (de)	1998-12-02	1999-11-30	Masse zum verkleben, beschichten und dichten aus cyanacrylaten und aldehyd- bzw. keton-kondensationsprodukten

Publications (1)

Publication Number	Publication Date
UA73930C2 true UA73930C2 (en)	2005-10-17

Family

ID=7889544

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2001064524A UA73930C2 (en)	1998-12-02	1999-11-30	Cyanoacrylate bulk for bonding, coating application and sealing

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)	NO20012717D0 (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)

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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 (de) *	2004-01-09	2005-08-04	Henkel Kgaa	Spaltüberbrückender Cyanacrylat-Klebstoff
US8192731B2 (en)	2005-10-25	2012-06-05	Loctite (R&D) Limited	Thickened cyanoacrylate compositions
ATE441685T1 (de) *	2007-06-15	2009-09-15	Max Planck Ges Zur Firderung D	Verfahren zur herstellung organischer poríser festkírper und mit diesem verfahren herstellbare festkírper
GB2463065B (en)	2008-09-01	2012-11-07	Loctite R & D Ltd	Transferable curable non-liquid film on a release substrate
JP6242564B2 (ja) *	2008-09-26	2017-12-06	ヘンケルアイピーアンドホールディングゲゼルシャフトミットベシュレンクテルハフツング	非流動性シアノアクリレート組成物
US9457613B2 (en)	2008-09-26	2016-10-04	Henkel IP & Holding GmbH	Cyanoacrylate compositions in non-flowable forms
CN103083718B (zh)	2011-11-02	2015-06-10	中国人民解放军军事医学科学院毒物药物研究所	一种可生物降解的医用粘合剂及其制备方法和用途
CN105419430A (zh) *	2015-11-24	2016-03-23	丹阳镇威汽配有限公司	雨刮片刮雨接触面表面涂层及其制备方法
US11634524B2 (en)	2016-07-26	2023-04-25	Ppg Industries Ohio, Inc.	Acid-catalyzed curable coating compositions containing 1,1 di-activated vinyl compounds and related coatings and processes
US11466159B2 (en)	2016-07-26	2022-10-11	Ppg Industries Ohio, Inc.	Particles having surfaces functionalized with 1,1-di-activated vinyl compounds
WO2018022785A1 (en)	2016-07-26	2018-02-01	Ppg Industries Ohio, Inc.	Three-dimensional printing processes using 1,1-di-activated vinyl compounds
US11078376B2 (en)	2016-07-26	2021-08-03	Ppg Industries Ohio, Inc.	Polyurethane coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes
ES2930756T3 (es)	2016-07-26	2022-12-21	Ppg Ind Ohio Inc	Composiciones de recubrimiento curables catalizadas por ácido que contienen compuestos vinílicos 1,1-diactivado y recubrimientos y procesos relacionados
US10961403B2 (en)	2016-07-26	2021-03-30	Ppg Industries Ohio, Inc.	Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds
JP6770633B2 (ja)	2016-07-26	2020-10-14	ピーピージー・インダストリーズ・オハイオ・インコーポレイテッドＰＰＧＩｎｄｕｓｔｒｉｅｓＯｈｉｏ，Ｉｎｃ．	１，１−二活性化ビニル化合物生成物を含有する複数層硬化性組成物および関連方法
JP7498561B2 (ja) *	2016-07-26	2024-06-12	ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド	１，１－二活性化ビニル化合物を含有する硬化性組成物ならびに関連のコーティングおよび方法
US10934411B2 (en)	2016-09-30	2021-03-02	Ppg Industries Ohio, Inc.	Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms
CN107442381B (zh) *	2017-09-01	2021-03-30	山东华成中德传动设备有限公司	一种木质模具的表面处理方法
GB2567220B (en)	2017-10-06	2021-01-27	Henkel IP & Holding GmbH	Solid cyanoacrylate compositions comprising thermoplastic polyurethane
CN112279999B (zh) *	2020-11-09	2022-03-11	广东石油化工学院	一种生物降解性可辐射固化的氨酯(甲基)丙烯酸酯及其制备方法
CN112322196A (zh) *	2020-11-24	2021-02-05	山东禹王和天下新材料有限公司	一种用于聚苯乙烯发泡材料快速粘接的胶黏剂及其制备方法

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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 SK SK743-2001A patent/SK7432001A3/sk unknown
- 1999-11-30 CN CN99813954A patent/CN1329648A/zh active Pending
- 1999-11-30 AU AU17785/00A patent/AU770134B2/en not_active Ceased
- 1999-11-30 TR TR2001/01471T patent/TR200101471T2/xx unknown
- 1999-11-30 UA UA2001064524A patent/UA73930C2/uk unknown
- 1999-11-30 EP EP99961028A patent/EP1159362A1/de not_active Withdrawn
- 1999-11-30 CZ CZ20011972A patent/CZ20011972A3/cs unknown
- 1999-11-30 HU HU0104526A patent/HUP0104526A3/hu unknown
- 1999-11-30 ID IDW00200101450A patent/ID30447A/id unknown
- 1999-11-30 CA CA002353605A patent/CA2353605A1/en not_active Abandoned
- 1999-11-30 PL PL99348719A patent/PL348719A1/xx not_active Application Discontinuation
- 1999-11-30 RU RU2001118044/04A patent/RU2238292C2/ru not_active IP Right Cessation
- 1999-11-30 KR KR1020017006731A patent/KR20010107993A/ko not_active Abandoned
- 1999-11-30 JP JP2000585342A patent/JP2002531629A/ja active Pending
- 1999-11-30 WO PCT/EP1999/009287 patent/WO2000032709A1/de not_active Ceased
- 1999-11-30 DE DE19957677A patent/DE19957677A1/de not_active Ceased
- 1999-11-30 BR BR9915814-0A patent/BR9915814A/pt not_active Application Discontinuation
2001
- 2001-06-01 ZA ZA200104538A patent/ZA200104538B/en unknown
- 2001-06-01 NO NO20012717A patent/NO20012717D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
TR200101471T2 (tr)	2001-11-21
HUP0104526A2 (hu)	2002-03-28
CA2353605A1 (en)	2000-06-08
RU2238292C2 (ru)	2004-10-20
JP2002531629A (ja)	2002-09-24
SK7432001A3 (en)	2002-01-07
KR20010107993A (ko)	2001-12-07
BR9915814A (pt)	2001-08-21
EP1159362A1 (de)	2001-12-05
CZ20011972A3 (cs)	2001-11-14
AU1778500A (en)	2000-06-19
ID30447A (id)	2001-12-06
HUP0104526A3 (en)	2003-07-28
DE19957677A1 (de)	2000-06-08
AU770134B2 (en)	2004-02-12
NO20012717L (no)	2001-06-01
NO20012717D0 (no)	2001-06-01
PL348719A1 (en)	2002-06-03
ZA200104538B (en)	2002-09-02
WO2000032709A1 (de)	2000-06-08
CN1329648A (zh)	2002-01-02

Publication	Publication Date	Title
RU2238292C2 (ru)	2004-10-20	Цианоакрилатная масса для склеивания на основе смеси из цианакрилатов и продуктов конденсации альдегидов и кетонов
US4042442A (en)	1977-08-16	2-Cyanoacrylate adhesive composition
US6852193B2 (en)	2005-02-08	Semi-solid one- or two-part compositions
EP2044137B1 (fr)	2015-03-04	Composition polymerisable et/ou reticulable sous irradiation par voie cationique et/ou radicalaire
JPS60231606A (ja)	1985-11-18	光重合性歯科接着剤ラツカー
RU2017107528A (ru)	2018-09-07	Отверждаемая композиция чернил с гелеобразующим агентом
EP1465958B1 (en)	2007-01-17	Alpha-cyanoacrylate adhesive systems
WO2008016057A1 (fr)	2008-02-07	Composition de résine durcissable
US6828291B2 (en)	2004-12-07	Semi-solid compositions for removing cured product
MXPA01005588A (en)	2002-03-26	Substance for bonding, coating and sealing, consisting of cyanoacrylates and aldehyde or ketone condensation products
Zhu et al.	2019	Preparation of polymerizable thermal initiator and its application in photo-induced thermal frontal polymerization
Ghaemy et al.	2012	Thermal and photocuring of an acrylate-based coating resin reinforced with nanosilica particles
CN109852202A (zh)	2019-06-07	含有苯并杂环骨架的硫酯作为紫外光吸收剂的应用
JP4329561B2 (ja)	2009-09-09	２−シアノアクリレート系組成物
JP2022526281A (ja)	2022-05-24	二液硬化性組成物
JPS58131940A (ja)	1983-08-06	新規化合物及びそれを用いた嫌気性接着剤
PT1369463E (pt)	2007-10-22	Composição adesiva
RU2193586C1 (ru)	2002-11-27	Клеевая композиция
JPH11106372A (ja)	1999-04-20	新規な２−シアノアクリレート
SU668332A1 (ru)	1983-11-15	Клеева композици
JPS61281174A (ja)	1986-12-11	粘着テ−プ用紫外線硬化組成物
JPS6015661B2 (ja)	1985-04-20	接着剤およびその製造法
EP4504844A1 (en)	2025-02-12	Two-part curable composition
JPH04217905A (ja)	1992-08-07	歯質接着用前処理剤
SU840290A1 (ru)	1981-06-23	Полимерный тампонажный состав