CN1329648A - 用于粘合剂、涂料和密封剂的由氰基丙烯酸酯和醛－或酮－缩合产物组成的物料 - Google Patents
用于粘合剂、涂料和密封剂的由氰基丙烯酸酯和醛－或酮－缩合产物组成的物料 Download PDFInfo
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- CN1329648A CN1329648A CN99813954A CN99813954A CN1329648A CN 1329648 A CN1329648 A CN 1329648A CN 99813954 A CN99813954 A CN 99813954A CN 99813954 A CN99813954 A CN 99813954A CN 1329648 A CN1329648 A CN 1329648A
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- Prior art keywords
- cyanoacrylate
- aldehyde
- alcohol
- weight
- oxygen
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- 229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 53
- 150000002576 ketones Chemical class 0.000 title claims abstract description 17
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 16
- 239000007859 condensation product Substances 0.000 title claims abstract description 14
- 239000011248 coating agent Substances 0.000 title claims abstract description 10
- 238000000576 coating method Methods 0.000 title claims abstract description 10
- 238000007789 sealing Methods 0.000 title claims abstract description 10
- 239000000126 substance Substances 0.000 title abstract description 13
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims description 54
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 48
- -1 phenyl aldehyde Chemical class 0.000 claims description 46
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 235000019441 ethanol Nutrition 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 claims description 15
- 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 10
- 229930195725 Mannitol Natural products 0.000 claims description 10
- 239000000594 mannitol Substances 0.000 claims description 10
- 235000010355 mannitol Nutrition 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000001816 cooling Methods 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
- 239000004902 Softening Agent Substances 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
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- 235000010447 xylitol Nutrition 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
- 229960002675 xylitol Drugs 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000004836 Glue Stick Substances 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000000123 paper Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000003292 glue Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- PCKALOHLBRPFOC-UHFFFAOYSA-N C(C=C)(=O)O.CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N Chemical compound C(C=C)(=O)O.CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N PCKALOHLBRPFOC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 230000008719 thickening Effects 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004830 Super Glue Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 3
- 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
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000004519 grease 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
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
- 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
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical group [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 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
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- DCFDVJPDXYGCOK-UHFFFAOYSA-N cyclohex-3-ene-1-carbaldehyde Chemical compound O=CC1CCC=CC1 DCFDVJPDXYGCOK-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-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
- 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
- JSPVGNGLUOYYBI-UHFFFAOYSA-N 1,5-dibromo-2,4-bis(4-nitrophenyl)pentan-3-one Chemical compound BrCC(C1=CC=C(C=C1)[N+](=O)[O-])C(=O)C(CBr)C1=CC=C(C=C1)[N+](=O)[O-] JSPVGNGLUOYYBI-UHFFFAOYSA-N 0.000 description 1
- ARCQXGKLZMBEBF-UHFFFAOYSA-N 1,5-dichloro-2,4-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1C(CCl)C(=O)C(CCl)C1=CC=CC=C1 ARCQXGKLZMBEBF-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
- JXAVVBPORYWDME-UHFFFAOYSA-N 1-cyclopropylpropan-1-one Chemical compound CCC(=O)C1CC1 JXAVVBPORYWDME-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
- 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
- ZOYJUTCFGXEJDP-UHFFFAOYSA-N 2,4-bis(4-bromophenyl)pentan-3-one Chemical compound C=1C=C(Br)C=CC=1C(C)C(=O)C(C)C1=CC=C(Br)C=C1 ZOYJUTCFGXEJDP-UHFFFAOYSA-N 0.000 description 1
- OPKKOAIXCNEIED-UHFFFAOYSA-N 2,4-bis(4-hydroxyphenyl)pentan-3-one Chemical compound C=1C=C(O)C=CC=1C(C)C(=O)C(C)C1=CC=C(O)C=C1 OPKKOAIXCNEIED-UHFFFAOYSA-N 0.000 description 1
- PFWNJNNEVPAKSN-UHFFFAOYSA-N 2,4-bis(furan-2-yl)pentan-3-one Chemical compound O1C(=CC=C1)C(C)C(=O)C(C)C=1OC=CC=1 PFWNJNNEVPAKSN-UHFFFAOYSA-N 0.000 description 1
- JMEXQRPUGKCOLI-UHFFFAOYSA-N 2,4-di(pyrazin-2-yl)pentan-3-one Chemical compound N1=C(C=NC=C1)C(C)C(=O)C(C)C1=NC=CN=C1 JMEXQRPUGKCOLI-UHFFFAOYSA-N 0.000 description 1
- BXVKRKAHHQYFHB-UHFFFAOYSA-N 2,4-dinaphthalen-1-ylpentan-3-one Chemical compound C1(=CC=CC2=CC=CC=C12)C(C)C(=O)C(C)C1=CC=CC2=CC=CC=C12 BXVKRKAHHQYFHB-UHFFFAOYSA-N 0.000 description 1
- OWDHNYUHCPSQFR-UHFFFAOYSA-N 2,4-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1C(C)C(=O)C(C)C1=CC=CC=C1 OWDHNYUHCPSQFR-UHFFFAOYSA-N 0.000 description 1
- YIJQZATYZRLEEA-UHFFFAOYSA-N 2,4-dipyridin-2-ylpentan-3-one Chemical compound N1=C(C=CC=C1)C(C)C(=O)C(C1=NC=CC=C1)C YIJQZATYZRLEEA-UHFFFAOYSA-N 0.000 description 1
- DTSSHTYFJUJZOH-UHFFFAOYSA-N 2,4-dipyridin-4-ylpentan-3-one Chemical compound C=1C=NC=CC=1C(C)C(=O)C(C)C1=CC=NC=C1 DTSSHTYFJUJZOH-UHFFFAOYSA-N 0.000 description 1
- ZLLNHIWLSFAHDR-UHFFFAOYSA-N 2,4-dithiophen-2-ylpentan-3-one Chemical compound S1C(=CC=C1)C(C)C(=O)C(C)C=1SC=CC1 ZLLNHIWLSFAHDR-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
- QMIGEDXMDGEZSR-UHFFFAOYSA-N 2,5-dimethoxyoxolane-3-carbaldehyde Chemical compound COC1CC(C=O)C(OC)O1 QMIGEDXMDGEZSR-UHFFFAOYSA-N 0.000 description 1
- DYVJZCIYRQUXBA-UHFFFAOYSA-N 2,5-dimethyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CC1=COC(C)(C=O)CC1 DYVJZCIYRQUXBA-UHFFFAOYSA-N 0.000 description 1
- UDVDQPMLLBOKKZ-UHFFFAOYSA-N 2,5-dipropyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CCCC1=COC(CCC)(C=O)CC1 UDVDQPMLLBOKKZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J159/00—Adhesives based on polyacetals; Adhesives based on derivatives of polyacetals
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19855272 | 1998-12-02 | ||
| DE19855272.6 | 1998-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1329648A true CN1329648A (zh) | 2002-01-02 |
Family
ID=7889544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99813954A Pending CN1329648A (zh) | 1998-12-02 | 1999-11-30 | 用于粘合剂、涂料和密封剂的由氰基丙烯酸酯和醛－或酮－缩合产物组成的物料 |
Country Status (19)
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| EP (1) | EP1159362A1 (de) |
| JP (1) | JP2002531629A (de) |
| KR (1) | KR20010107993A (de) |
| CN (1) | CN1329648A (de) |
| AU (1) | AU770134B2 (de) |
| BR (1) | BR9915814A (de) |
| CA (1) | CA2353605A1 (de) |
| CZ (1) | CZ20011972A3 (de) |
| DE (1) | DE19957677A1 (de) |
| HU (1) | HUP0104526A3 (de) |
| ID (1) | ID30447A (de) |
| NO (1) | NO20012717L (de) |
| PL (1) | PL348719A1 (de) |
| RU (1) | RU2238292C2 (de) |
| SK (1) | SK7432001A3 (de) |
| TR (1) | TR200101471T2 (de) |
| UA (1) | UA73930C2 (de) |
| WO (1) | WO2000032709A1 (de) |
| ZA (1) | ZA200104538B (de) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102197102A (zh) * | 2008-09-26 | 2011-09-21 | 汉高公司 | 不可流动形式的氰基丙烯酸酯组合物 |
| CN101765620B (zh) * | 2007-06-15 | 2012-06-27 | 马克斯-普郎克科学促进学会 | 有机多孔性固体的制备方法以及通过该方法可获得的固体 |
| CN103083718A (zh) * | 2011-11-02 | 2013-05-08 | 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 |
| CN107442381A (zh) * | 2017-09-01 | 2017-12-08 | 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 |
| CN112279999A (zh) * | 2020-11-09 | 2021-01-29 | 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 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE20000441A1 (en) | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid composition for removing cured product |
| IE20000440A1 (en) * | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid one- or two-part compositions |
| DE102004001493A1 (de) * | 2004-01-09 | 2005-08-04 | Henkel Kgaa | Spaltüberbrückender Cyanacrylat-Klebstoff |
| US8192731B2 (en) | 2005-10-25 | 2012-06-05 | Loctite (R&D) Limited | Thickened cyanoacrylate compositions |
| GB2463065B (en) * | 2008-09-01 | 2012-11-07 | Loctite R & D Ltd | Transferable curable non-liquid film on a release substrate |
| US9457613B2 (en) | 2008-09-26 | 2016-10-04 | Henkel IP & Holding GmbH | Cyanoacrylate compositions in non-flowable forms |
| CN109642098B (zh) | 2016-07-26 | 2022-02-11 | Ppg工业俄亥俄公司 | 包含1,1-二活化的乙烯基化合物的可电沉积的涂料组合物 |
| 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 |
| 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 |
| EP4151689A1 (de) | 2016-07-26 | 2023-03-22 | PPG Industries Ohio, Inc. | Härtbare zusammensetzungen mit 1,1-diaktivierten vinylverbindungen und verwandte beschichtungen und verfahren |
| CN109476081B (zh) | 2016-07-26 | 2021-11-23 | Ppg工业俄亥俄公司 | 使用1,1-二活化的乙烯基化合物的三维印刷方法 |
| CN109642099B (zh) | 2016-07-26 | 2021-11-30 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物的聚氨酯涂料组合物和相关的涂料和方法 |
| US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| EP3491057B1 (de) | 2016-07-26 | 2022-11-09 | PPG Industries Ohio, Inc. | Partikel mit oberflächen, die mit 1,1-di-aktivierten vinylverbindungen funktionalisiert sind |
| 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 |
| GB2567220B (en) | 2017-10-06 | 2021-01-27 | Henkel IP & Holding GmbH | Solid cyanoacrylate compositions comprising thermoplastic polyurethane |
Family Cites Families (3)
| 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 (de) * | 1973-02-05 | 1974-10-04 | ||
| JPS54107993A (en) * | 1978-02-10 | 1979-08-24 | Matsumoto Seiyaku Kogyo Kk | Alphaacyanoacrylate composition |
-
1999
- 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 DE DE19957677A patent/DE19957677A1/de not_active Ceased
- 1999-11-30 SK SK743-2001A patent/SK7432001A3/sk unknown
- 1999-11-30 CN CN99813954A patent/CN1329648A/zh active Pending
- 1999-11-30 HU HU0104526A patent/HUP0104526A3/hu unknown
- 1999-11-30 BR BR9915814-0A patent/BR9915814A/pt not_active Application Discontinuation
- 1999-11-30 ID IDW00200101450A patent/ID30447A/id unknown
- 1999-11-30 JP JP2000585342A patent/JP2002531629A/ja active Pending
- 1999-11-30 WO PCT/EP1999/009287 patent/WO2000032709A1/de not_active Application Discontinuation
- 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 RU RU2001118044/04A patent/RU2238292C2/ru not_active IP Right Cessation
- 1999-11-30 PL PL99348719A patent/PL348719A1/xx not_active Application Discontinuation
- 1999-11-30 KR KR1020017006731A patent/KR20010107993A/ko active IP Right Grant
- 1999-11-30 UA UA2001064524A patent/UA73930C2/uk unknown
- 1999-11-30 CZ CZ20011972A patent/CZ20011972A3/cs unknown
-
2001
- 2001-06-01 NO NO20012717A patent/NO20012717L/no not_active Application Discontinuation
- 2001-06-01 ZA ZA200104538A patent/ZA200104538B/en unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101765620B (zh) * | 2007-06-15 | 2012-06-27 | 马克斯-普郎克科学促进学会 | 有机多孔性固体的制备方法以及通过该方法可获得的固体 |
| CN102197102A (zh) * | 2008-09-26 | 2011-09-21 | 汉高公司 | 不可流动形式的氰基丙烯酸酯组合物 |
| 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 |
| CN103083718A (zh) * | 2011-11-02 | 2013-05-08 | 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 |
| US9750841B2 (en) | 2011-11-02 | 2017-09-05 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. | Biodegradable medical adhesive and preparation method and use thereof |
| 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 |
| CN107442381A (zh) * | 2017-09-01 | 2017-12-08 | 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 |
| 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 |
| CN112279999A (zh) * | 2020-11-09 | 2021-01-29 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| UA73930C2 (en) | 2005-10-17 |
| RU2238292C2 (ru) | 2004-10-20 |
| NO20012717D0 (no) | 2001-06-01 |
| HUP0104526A2 (hu) | 2002-03-28 |
| ZA200104538B (en) | 2002-09-02 |
| TR200101471T2 (tr) | 2001-11-21 |
| DE19957677A1 (de) | 2000-06-08 |
| SK7432001A3 (en) | 2002-01-07 |
| CZ20011972A3 (cs) | 2001-11-14 |
| AU770134B2 (en) | 2004-02-12 |
| HUP0104526A3 (en) | 2003-07-28 |
| KR20010107993A (ko) | 2001-12-07 |
| AU1778500A (en) | 2000-06-19 |
| NO20012717L (no) | 2001-06-01 |
| BR9915814A (pt) | 2001-08-21 |
| CA2353605A1 (en) | 2000-06-08 |
| WO2000032709A1 (de) | 2000-06-08 |
| ID30447A (id) | 2001-12-06 |
| PL348719A1 (en) | 2002-06-03 |
| EP1159362A1 (de) | 2001-12-05 |
| JP2002531629A (ja) | 2002-09-24 |
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