DE1594209A1 - Klebstoffe und Verbundstoffe - Google Patents
Klebstoffe und VerbundstoffeInfo
- Publication number
- DE1594209A1 DE1594209A1 DE1963P0032441 DEP0032441A DE1594209A1 DE 1594209 A1 DE1594209 A1 DE 1594209A1 DE 1963P0032441 DE1963P0032441 DE 1963P0032441 DE P0032441 A DEP0032441 A DE P0032441A DE 1594209 A1 DE1594209 A1 DE 1594209A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- polymer
- adhesive
- alkyl radical
- carbon
- 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.)
- Pending
Links
- 239000000853 adhesive Substances 0.000 title claims description 111
- 230000001070 adhesive effect Effects 0.000 title claims description 111
- 239000002131 composite material Substances 0.000 title claims description 53
- 229920002620 polyvinyl fluoride Polymers 0.000 claims description 55
- 229920002554 vinyl polymer Polymers 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 229920000647 polyepoxide Polymers 0.000 claims description 27
- 239000003822 epoxy resin Substances 0.000 claims description 26
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000000969 carrier Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229920000768 polyamine Polymers 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims 6
- 229920006222 acrylic ester polymer Polymers 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 aliphatic carbon radical Chemical class 0.000 description 35
- 238000012360 testing method Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 19
- 238000003475 lamination Methods 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 11
- 239000011888 foil Substances 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000011120 plywood Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- 125000000466 oxiranyl group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000010425 asbestos Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052895 riebeckite Inorganic materials 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 2
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229910000680 Aluminized steel Inorganic materials 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229910001335 Galvanized steel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920001079 Thiokol (polymer) Polymers 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000010426 asphalt Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000001539 azetidines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920006332 epoxy adhesive Polymers 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012939 laminating adhesive Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910052572 stoneware Inorganic materials 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GGQRKYMKYMRZTF-UHFFFAOYSA-N 2,2,3,3-tetrakis(prop-1-enyl)butanedioic acid Chemical compound CC=CC(C=CC)(C(O)=O)C(C=CC)(C=CC)C(O)=O GGQRKYMKYMRZTF-UHFFFAOYSA-N 0.000 description 1
- XIPXMPBEPRYQEG-UHFFFAOYSA-N 2,4-dioctylazetidine Chemical compound CCCCCCCCC1CC(CCCCCCCC)N1 XIPXMPBEPRYQEG-UHFFFAOYSA-N 0.000 description 1
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- COTACYJQEIUCHG-UHFFFAOYSA-N 2-(2-methylbutyl)aziridine Chemical compound CCC(C)CC1CN1 COTACYJQEIUCHG-UHFFFAOYSA-N 0.000 description 1
- DJQMDRLOJHSJPB-UHFFFAOYSA-N 2-(2-methylpentyl)aziridine Chemical compound CC(CC1NC1)CCC DJQMDRLOJHSJPB-UHFFFAOYSA-N 0.000 description 1
- ICQBTDMTODKPQU-UHFFFAOYSA-N 2-(2-propan-2-ylpentyl)aziridine Chemical compound CCCC(C(C)C)CC1CN1 ICQBTDMTODKPQU-UHFFFAOYSA-N 0.000 description 1
- BNNYIVSAJJATJE-UHFFFAOYSA-N 2-(3-methylbutyl)aziridine Chemical compound CC(C)CCC1CN1 BNNYIVSAJJATJE-UHFFFAOYSA-N 0.000 description 1
- BICJYSTYIAPCAR-UHFFFAOYSA-N 2-(3-methylpentyl)aziridine Chemical compound CC(CCC1NC1)CC BICJYSTYIAPCAR-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- DQFZABLNCLNVBZ-UHFFFAOYSA-N 2-(4-methylpentyl)aziridine Chemical compound CC(C)CCCC1CN1 DQFZABLNCLNVBZ-UHFFFAOYSA-N 0.000 description 1
- LKYCAAULXGRNFC-UHFFFAOYSA-N 2-(bromomethyl)-3-ethyloxirane Chemical compound CCC1OC1CBr LKYCAAULXGRNFC-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical class CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GQDYKYGFCJNFOU-UHFFFAOYSA-N 2-butylaziridine Chemical compound CCCCC1CN1 GQDYKYGFCJNFOU-UHFFFAOYSA-N 0.000 description 1
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 description 1
- GUPVQIMZTOGWBH-UHFFFAOYSA-N 2-hexan-2-ylaziridine Chemical compound CCCCC(C)C1CN1 GUPVQIMZTOGWBH-UHFFFAOYSA-N 0.000 description 1
- NKGPSOBDVMBRSX-UHFFFAOYSA-N 2-hexylaziridine Chemical compound CCCCCCC1CN1 NKGPSOBDVMBRSX-UHFFFAOYSA-N 0.000 description 1
- DLBWPRNUXWYLRN-UHFFFAOYSA-N 2-methylazetidine Chemical compound CC1CCN1 DLBWPRNUXWYLRN-UHFFFAOYSA-N 0.000 description 1
- RRDVZSARKGXBQW-UHFFFAOYSA-N 2-pentan-2-ylaziridine Chemical compound CCCC(C)C1CN1 RRDVZSARKGXBQW-UHFFFAOYSA-N 0.000 description 1
- OQPVYUGOKGJCGN-UHFFFAOYSA-N 2-pentylaziridine Chemical compound CCCCCC1CN1 OQPVYUGOKGJCGN-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
- C09J157/00—Adhesives based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09J157/04—Copolymers in which only the monomer in minority is defined
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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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31515—As intermediate layer
- Y10T428/31522—Next to metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US218102A US3228823A (en) | 1962-08-20 | 1962-08-20 | Polyvinyl fluoride film surfaced substrates and process of making same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1594209A1 true DE1594209A1 (de) | 1969-08-28 |
Family
ID=22813754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1963P0032441 Pending DE1594209A1 (de) | 1962-08-20 | 1963-08-20 | Klebstoffe und Verbundstoffe |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3228823A (en:Method) |
| BE (1) | BE636357A (en:Method) |
| DE (1) | DE1594209A1 (en:Method) |
| GB (1) | GB1002231A (en:Method) |
| NL (1) | NL296849A (en:Method) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300927A (en) * | 1963-01-21 | 1967-01-31 | Ruberoid Company | Laminated sheet material |
| US3369959A (en) * | 1963-10-25 | 1968-02-20 | Du Pont | Laminate of polyvinyl fluoride |
| US3340137A (en) * | 1964-01-23 | 1967-09-05 | Formica Corp | Unitary weather-resistant decorative laminate and method of making same |
| US3364049A (en) * | 1964-04-27 | 1968-01-16 | Du Pont | Self-destructible decal with adhesive on one surface and indicia covered by a vinyl addition polymer on the other |
| US3475261A (en) * | 1964-06-02 | 1969-10-28 | Us Plywood Champ Papers Inc | Plastic covered laminate,and method,and apparatus for manufacturing the same |
| US3390704A (en) * | 1964-11-19 | 1968-07-02 | Du Pont | Polyolefin fluid conduit laminates |
| US3399248A (en) * | 1964-12-01 | 1968-08-27 | Du Pont | Reaction of amino-ester modified vinyl polymer and epoxide resins to form an adhesive composition |
| US3454457A (en) * | 1965-02-10 | 1969-07-08 | Domtar Ltd | Fabricated caul plate |
| US3397108A (en) * | 1965-02-17 | 1968-08-13 | Du Pont | Deglossed polyvinyl fluoride film structures |
| US3475248A (en) * | 1965-12-06 | 1969-10-28 | Du Pont | Method of thermoplastic film manufacture |
| US3421973A (en) * | 1965-12-20 | 1969-01-14 | Formica Corp | Protection of plastic materials |
| US3421971A (en) * | 1966-01-07 | 1969-01-14 | Formica Corp | Weatherable plastic laminates |
| US3454461A (en) * | 1966-04-15 | 1969-07-08 | Du Pont | Polyethylene-polyvinyl fluoride film laminated structure and process of making same |
| US3492194A (en) * | 1966-07-06 | 1970-01-27 | Us Plywood Champ Papers Inc | Textured plastic overlay panel |
| US3522125A (en) * | 1967-01-31 | 1970-07-28 | Mobil Oil Corp | Process of bonding a wood substrate and an etched surface of a polyvinylfluoride film |
| US3538185A (en) * | 1967-08-10 | 1970-11-03 | Dow Chemical Co | Coating compositions containing vinyl polymers with pendant alkylenimine group and epoxy resins |
| BE756111A (fr) * | 1969-09-15 | 1971-02-15 | Dynamit Nobel Ag | Procede de fabrication de feuilles de fluorure de polyvinyle aptes au collage |
| US4095760A (en) * | 1975-10-10 | 1978-06-20 | James A. Black | Structural skin construction materials and method |
| GB1563502A (en) * | 1976-06-03 | 1980-03-26 | Redland Claddings Ltd | Building products and methods of manufacturing same |
| US4272621A (en) * | 1978-10-24 | 1981-06-09 | The Dow Chemical Company | Water thinnable coating compositions from aminoalkylated interpolymers |
| DE2934086A1 (de) * | 1979-08-23 | 1981-04-09 | Röhm GmbH, 6100 Darmstadt | Emulsionspolymerisat mit verdickungswirkung im sauren bereich |
| US4353819A (en) * | 1981-03-13 | 1982-10-12 | The Dow Chemical Company | Fast curing polyepoxide coating compositions with good pot life |
| US4598522A (en) * | 1984-06-22 | 1986-07-08 | Hoofe William J Iii | Interlocking panels |
| US4806577A (en) * | 1986-11-18 | 1989-02-21 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Adhesive composition |
| CA2030062A1 (en) * | 1989-11-20 | 1991-05-21 | Koichiro Saeki | Curable resin composition |
| US5225260A (en) * | 1991-03-28 | 1993-07-06 | Brady Coated Products Co. | Subsurface printable laminate with carrier and application tape |
| US5209959A (en) * | 1991-03-28 | 1993-05-11 | Brady Coated Products Co. | Surface printable polyvinyl chloride laminate with carrier and application tape |
| US20020169271A1 (en) * | 2000-10-26 | 2002-11-14 | Weiling Peng | Adhesive mixture for bonding fluorohydrocarbon film to fibrous cementitious materials |
| NZ525391A (en) * | 2000-10-26 | 2004-11-26 | James Hardie Res Pty Ltd | Building panel assembly having a protective film, method of making same and adhesive system for bonding the protective film |
| US8281535B2 (en) * | 2002-07-16 | 2012-10-09 | James Hardie Technology Limited | Packaging prefinished fiber cement articles |
| CN1668458A (zh) * | 2002-07-16 | 2005-09-14 | 詹姆斯哈迪国际财金公司 | 对预处理纤维增强水泥产品的包装 |
| NZ536867A (en) * | 2003-11-28 | 2006-04-28 | James Hardie Int Finance Bv | Eave lining system for buildings |
| CN106009528A (zh) * | 2016-05-26 | 2016-10-12 | 苏州之诺新材料科技有限公司 | 一种用于树脂传递模塑成型的低粘度韧性环氧树脂基体及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776951A (en) * | 1954-12-08 | 1957-01-08 | Rohm & Haas | Amides of vinyl ethers containing hydroxyl groups and polymers thereof |
| NL271330A (en:Method) * | 1960-11-15 | 1900-01-01 |
-
0
- NL NL296849D patent/NL296849A/xx unknown
- BE BE636357D patent/BE636357A/xx unknown
-
1962
- 1962-08-20 US US218102A patent/US3228823A/en not_active Expired - Lifetime
-
1963
- 1963-08-20 DE DE1963P0032441 patent/DE1594209A1/de active Pending
- 1963-08-20 GB GB32930/63A patent/GB1002231A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1002231A (en) | 1965-08-25 |
| US3228823A (en) | 1966-01-11 |
| BE636357A (en:Method) | 1900-01-01 |
| NL296849A (en:Method) | 1900-01-01 |
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