SE425402C - PHOTOPOLYMERIZABLE TRANSFER - Google Patents
PHOTOPOLYMERIZABLE TRANSFERInfo
- Publication number
- SE425402C SE425402C SE7803474A SE7803474A SE425402C SE 425402 C SE425402 C SE 425402C SE 7803474 A SE7803474 A SE 7803474A SE 7803474 A SE7803474 A SE 7803474A SE 425402 C SE425402 C SE 425402C
- Authority
- SE
- Sweden
- Prior art keywords
- ether
- acid
- photopolymerizable
- benzoin
- acrylate
- Prior art date
Links
- 238000012546 transfer Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229920003180 amino resin Polymers 0.000 claims description 6
- 239000004922 lacquer Substances 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 81
- -1 melamine compound Chemical class 0.000 description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 238000000576 coating method Methods 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 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 description 9
- 239000011248 coating agent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229960002130 benzoin Drugs 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- JJDGTGGQXAAVQX-UHFFFAOYSA-N 6-methyl-1-(6-methylheptoxy)heptane Chemical compound CC(C)CCCCCOCCCCCC(C)C JJDGTGGQXAAVQX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- DEBGMRXCXCOKTA-UHFFFAOYSA-N 1-methoxy-1-(1-methoxyethoxy)ethane Chemical compound COC(C)OC(C)OC DEBGMRXCXCOKTA-UHFFFAOYSA-N 0.000 description 2
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-UHFFFAOYSA-N 0.000 description 2
- ZVNYKZKUBKIIAH-UHFFFAOYSA-N 2-(oxiran-2-yl)acetic acid Chemical class OC(=O)CC1CO1 ZVNYKZKUBKIIAH-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000011111 cardboard Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000004662 dithiols Chemical class 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
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-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
- LHUIQDDXBLROJX-UHFFFAOYSA-N (2-methoxy-2,4-diphenyl-1,3-dioxolan-4-yl)-phenylmethanone Chemical compound C1(=CC=CC=C1)C1(OCC(O1)(C1=CC=CC=C1)C(C1=CC=CC=C1)=O)OC LHUIQDDXBLROJX-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- 125000006091 1,3-dioxolane group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- RYZNARRKSYMPCW-UHFFFAOYSA-N 2-hexoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCCCC)C(=O)C1=CC=CC=C1 RYZNARRKSYMPCW-UHFFFAOYSA-N 0.000 description 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 1
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
Description
7803474-1 r_ - av aminoplasthartserna minska överdragens vattenkänslighet. I jämförel- seförsök i denna Offenlegungsschrift visas att endast den karhoxyl- grupper innehållande polymeren kommer ifråga för uppnående av vidhäft- ningshållfasthet. Dessutom skall pigmentvätningen samt flyt- och ut- flytningsegenskaperna för de fotopolymeriserbara blandningarna för- bättras genom de karboxylgrupper innehållande polymererna. De karboxyl- grupper.innehållande polymererna reagerar dock inte under bestrâlnings- betingelserna varför överdrag med dålig beständighet mot organiska lösningsmedel såsom aceton bildas. 7803474-1 r_ - of the aminoplast resins reduce the water sensitivity of the coatings. Comparative experiments in this Offenlegungsschrift show that only the carhoxyl groups containing the polymer are suitable for achieving adhesion strength. In addition, the pigment wetting as well as the flow and flow properties of the photopolymerizable mixtures are to be improved by the carboxyl groups containing the polymers. However, the carboxyl groups containing the polymers do not react under the irradiation conditions, so coatings with poor resistance to organic solvents such as acetone are formed.
Vidare är genom DT-OS 2 613 098 fotopolymeriserbara bland- ningar kända för framställning av pressmassor, vilka blandningar be- står av en omättad polyester, minst en hydroxylgrupper, olefiniskt omättade fotopolymeriserbara monomerer och en metylolgrupp innehållan- de melaminförening samt en inhibitor och en fotoinitiator. Härdningen av blandningen sker genom fotopolymerisation och samtidig eller efter- följande tillförsel av värme. Härdningen i värme accelereras genom tillsats av p-toluensulfonsyra. En nackdel med sådana blandningar be- står i den otillräckliga lagringsstabiliteten, som gör sig bemärkt speciellt om de beskrivna blandningarna insättes som överdragsmedel.Furthermore, photopolymerizable mixtures are known from DT-OS 2 613 098 for the production of press pulps, which mixtures consist of an unsaturated polyester, at least one hydroxyl group, olefinically unsaturated photopolymerizable monomers and a methylol group containing melamine compound and an inhibitor and a photoinitiator . The curing of the mixture takes place by photopolymerization and simultaneous or subsequent application of heat. The heat curing is accelerated by the addition of p-toluenesulfonic acid. A disadvantage of such mixtures is the insufficient storage stability, which becomes noticeable especially if the described mixtures are used as coating agents.
Till grund för föreliggande uppfinning låg uppgiften att ställa fotopolymeriserbara överdragsmedel till förfogande, vilka inne- håller minst en fotopolymeriserbar monomer med minst en fotopolymeri- serbar C-C/dubbelbindning och minst ett aminoplastharts, vilka över- dragsmedel uppvisar god lagringsstabilitet och efter fotopolymerisa- tion ger väl vidhäftande överdrag, speciellt på metaller. Dessutom skall de härdade överdragen vara lösningsmedelsbeständiga, speciellt mot aceton.The object of the present invention was to provide photopolymerizable coating compositions which contain at least one photopolymerizable monomer with at least one photopolymerizable CC / double bond and at least one aminoplast resin, which coating compositions exhibit good storage stability and after photopolymerization give good adhesive coatings, especially on metals. In addition, the cured coatings must be solvent resistant, especially to acetone.
Uppgiften har enligt uppfinningen lösts genom att fotopoly- merisâšhara blandningar av minst en fotopolymeriserbar monomer och minst/aminoplast polymeriseras i närvaro av en fotoinitiatorkombina- tion av minst två fotoinitiatorer, varvid minst en av fotoinitiatorerna innehåller en eller flera sura grupper, som vid fotopolymerisationen bildar syror, och varvid minst en av fotoinitiatorerna är fri från sådana syragrupper.The object has been solved according to the invention by polymerizing photopolymerizable mixtures of at least one photopolymerizable monomer and at least / aminoplast in the presence of a photoinitiator combination of at least two photoinitiators, at least one of the photoinitiators containing one or more acidic groups which form acids in the photopolymerization , and wherein at least one of the photoinitiators is free of such acid groups.
Uppfinningen hänför sig således till fotopolymeriserbara överdragsmedel, vilka eventuellt innehåller lösningsmedel, färgämnen, pigment och andra vanliga lackhjälpmedel, från blandningar av 7803474-1 A) 70 - 99 vikt-% av minst en fotopolymeriserbar förening med minst en fotopolymeriserbar, eteniskt omättad C-C/dubbelbindning, B) l - 30 vikt-% av minst ett aminoplastharfiæoch C) 0,1 - 20 vikt-%, räknat på summan av A) + B), av minst tvâ foto- initiatorer, vilka överdragsmedel kännetecknas av att minst en av fotoinitiatorerna innehåller en eller flera inbyggda sura grupper, som vid fotopolymeri- sationen bildar syror, och varvid minst en av fotoinitiatorerna är fri från sådana sura grupper.The invention thus relates to photopolymerizable coating compositions, which optionally contain solvents, dyes, pigments and other common lacquers, from mixtures of 7803474-1 A) 70-99% by weight of at least one photopolymerizable compound with at least one photopolymerizable, ethylenically unsaturated CC / double bond , B) 1 to 30% by weight of at least one aminoplastic resin and C) 0,1 to 20% by weight, based on the sum of A) + B), of at least two photoinitiators, which coating compositions are characterized by at least one of the photoinitiators contains one or more built-in acidic groups which during the photopolymerization form acids, and wherein at least one of the photoinitiators is free from such acidic groups.
Företrädosvis består blandningarna av 80 - 97 vikt-% av komponenten A) och 3 - 20 vikt-% av komponenten B).Preferably the mixtures consist of 80 - 97% by weight of component A) and 3 - 20% by weight of component B).
Summan av viktprocenthalterna av A) och B) är 100.The sum of the weight percentages of A) and B) is 100.
Fotoinitiatorerna ingår företrädesvis i en mängd av 0,1 - 5 vikt-%, räknat på summan av A) och B), i blandningen.The photoinitiators are preferably included in the mixture in an amount of 0.1 to 5% by weight, based on the sum of A) and B).
Av de totalt insatta fotoinitiatormängderna faller 10 - 90 vikt-%, företrädesvis 25 - 75 vikt-%, på fotoinitiatorer, vilka innehåller en eller flera sura inbyggda grupper, som vid fotopolyme- risationen frigör syror, och 90 - 10 vikt-%, företrädesvis 75 - 25 vikt-%, på fotoinitiatorer, vilka är fria från sura grupper.Of the total amounts of photoinitiators used, 10 to 90% by weight, preferably 25 to 75% by weight, fall on photoinitiators which contain one or more acidic built-in groups which release acids during the photopolymerization, and 90 to 10% by weight, preferably 75 - 25% by weight, on photoinitiators, which are free of acidic groups.
Som fotopolymeriserbara föreningar med minst en fotopoly- meriserbar eteniskt omättad C-C/dubbelbindning kan som exempel nämnas: I) estrar av akryl- eller metakrylsyra med alifatiska Cl- CS, cyklo- alifatiska C5-C6, aralifatiska C7-C8 monoalkoholer, exempelvis metylakrylat, etylakrylat, n-propylakrylat, isopropylakrylat, n-butylakrylat, tert.-butylakrylat, metylhexylakrylat, 2-etyl- hexylakrylat och motsvarande metakrylsyraestrar; cyklopentyl- akrylat, cyklohexylakrylat eller motsvarande metakrylsyraestrar; bensylakrylat, B-fenyletylakrylat och motsvarande metakrylsyra- estrar.Examples of photopolymerizable compounds having at least one photopolymerizable ethylenically unsaturated CC / double bond are: I) esters of acrylic or methacrylic acid with aliphatic C1-C6, cycloaliphatic C5-C6, araliphatic C7-C8 monoalcohols, for example methyl acrylate, ethyl methyl acrylate , n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, tert-butyl acrylate, methyl hexyl acrylate, 2-ethyl hexyl acrylate and the corresponding methacrylic acid esters; cyclopentyl acrylate, cyclohexyl acrylate or the corresponding methacrylic acid esters; benzyl acrylate, β-phenylethyl acrylate and the corresponding methacrylic acid esters.
II) hydroxialkylestrar av akryl- eller metakrylsyra med 2 - 4 C-ato- mer i alkoholkomponenten, exempelvis 2-hydroxietylakrylat, 2- hydroxipropylakrylat, 3-hydroxipropylakrylat, 2-hydroxibutyl- akrylat, 4-hydroxibutylakrylat eller motsvarande metakrylsyra- estrar.II) hydroxyalkyl esters of acrylic or methacrylic acid having 2 to 4 C atoms in the alcohol component, for example 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate or the corresponding methacrylic acid esters.
IEI) di- och polyakrylater samt di- och polymetakrylater av glykoler med 2 - 6 C-atomer och polyoler med 3 - 4 hydroxylgrupper och 3 - 6 C-atomer, exempelvis etylenglykoldiakrylat, propandiol-l,3-di- 7803474-1 »P akrylat, butandiol-1,4-diakrylat, hexandiol-1,6-diakrylat, tri- metylolpropantriakrylat, pentaerytrittri- och -tetraakrylat samt motsvarande metakrylater, vidare di(met)-akrylater av polyeter- glykoler av qlykol, propandiol-1,3 och butandiol-1,4.IEI) di- and polyacrylates and di- and polymethacrylates of glycols having 2 to 6 carbon atoms and polyols having 3 to 4 hydroxyl groups and 3 to 6 carbon atoms, for example ethylene glycol diacrylate, propanediol-1,3-di- 7803474-1 » Acrylate, butanediol-1,4-diacrylate, hexanediol-1,6-diacrylate, trimethylolpropane triacrylate, pentaerythritol tri- and tetrachrylate and corresponding methacrylates, further di (meth) acrylates of polyether glycols of glycol, propanediol-1, 3 and butanediol-1,4.
IV) aromatiska vinyl- och divinylföreningar, såsom styren, metyl- styren och divinylbensen.IV) aromatic vinyl and divinyl compounds, such as styrene, methylstyrene and divinylbenzene.
V) N-metylolakrylamid eller N-metylolmetakrylamid samt motsvarande N-metylolalkyletrar med l - 4 C-atomer i alkyletergruppen res- pektive motsvarande N-metylolallyletrar, speciellt N-metoximetyl- (met)-akrylamid, N-butoxi-metyl(met)akrylamid och N-allyloxi- metyl(met)akrylamid.V) N-methylolacrylamide or N-methylolmethacrylamide and the corresponding N-methylolalkyl ethers having 1 to 4 C atoms in the alkyl ether group or the corresponding N-methylolallyl ethers, in particular N-methoxymethyl- (meth) -acrylamide, N-butoxymethyl (meth) acrylamide and N-allyloxymethyl (meth) acrylamide.
VI) vinylalkyletrar med l - 4 C-atomer i alkylgruppen såsom vinyl- metyleter, vinyletyleter, vinylpropyleter och vinylbutyleter.VI) vinyl alkyl ethers having 1 to 4 C atoms in the alkyl group such as vinyl methyl ether, vinyl ethyl ether, vinylpropyl ether and vinyl butyl ether.
VII) trimetylolpropandiallyletermono(met)akrylat, vinylpyridín, N- vinylkarbazcl, triallylfosfat och triallylisocyanurat.VII) trimethylolpropanedial ether mono (meth) acrylate, vinylpyridine, N-vinylcarbazycl, triallyl phosphate and triallyl isocyanurate.
VIII) omsättningsprodukter av glycidyl(met)akrylat med mättade, alifa- tiska mono- eller dikarbonsyror med 2 - 18 C-atomer eller med eteniskt omättade mono- eller dikarbonsyror med 3 - 10-C-atomer eller omsättningsprodukter av glycidylestrar av rymdförnätade alifatiska monokarbonsyror, speciellt glycidylestrar av grenade alifatiska monokarbonsyror med 9 ~ ll C-atomer med eteniskt omättade mono- eller dikarbonsyror med 3 - 10 C-atomer.VIII) reaction products of glycidyl (meth) acrylate with saturated aliphatic mono- or dicarboxylic acids having 2 to 18 C atoms or with ethylenically unsaturated mono- or dicarboxylic acids having 3 to 10-C atoms or reaction products of glycidyl esters of space-linked aliphatic aliphatic monocarbons , in particular glycidyl esters of branched aliphatic monocarboxylic acids having 9 to 11 carbon atoms with ethylenically unsaturated mono- or dicarboxylic acids having 3 to 10 carbon atoms.
IX) omättade polyesterhartser av ~d,p -omättade dikarbonsyror såsom maleinsyra, furmarsyra, itakonsyra, glutakonsyra, tetrahydro- ftalsyra eller deras anhydrider och dioler såsom etylenglykol, l,2-propandiol, 1,3-propandiol, 1,2-butandiol, l,4~butandiol, 2,2-dimetylpropandiol, hexandiol-2,5, hexandiol-1,6, 4,4'-di- hydroxidicyklohexyl-propan-2,2, cyklohexandiol, dimetylclcyklo- hexan, dietylenglykol och 2,2-bis-Ås-(ß -hydroxietoxi)-fenyl]- propan och pclyoler såsom glycerin, hexantriol, pentaerytrit, sorbit, trimetyloletan, trimetylolpropan och tris-(ß -hydroxi- etyl)~isocyanurat.IX) unsaturated polyester resins of α, β-unsaturated dicarboxylic acids such as maleic acid, furmaric acid, itaconic acid, glutaconic acid, tetrahydrophthalic acid or their anhydrides and diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 2,2-dimethylpropanediol, hexanediol-2,5, hexanediol-1,6, 4,4'-dioxydicyclohexyl-propane-2,2, cyclohexanediol, dimethylcycyclohexane, diethylene glycol and 2,2 -bis-Ås- (ß-hydroxyethoxy) -phenyl] -propane and polyols such as glycerin, hexanetriol, pentaerythritol, sorbitol, trimethylolethane, trimethylolpropane and tris- (ß-hydroxyethyl) -isocyanurate.
I de omättade polyesterhartserna kan upp till 50 mol-% av de omättade inkondenserade dikarbonsyrorna ersättas med andra dikarbon- syraenheter såsom av ftalsyra, isoftalsyra, 3,6-diklorftalsyra, tetra- klorftalsyra, hexahydroftalsyra, bârnsstenssyra och adipinsyra. 7803474-1 X) uretanakrylater, erhållna från: a) diisocyanater (l mol) och 2 mol hydroxialkyl(met)akrylater med 2 - 4 C~atomer i alkylgruppen, b) glykoler eller polyeterglykoler (l mol) och 2 mol av ett di- isocyanat, i efterhand omsatt med 2 mol av ett hydroxialkyl- (met)akrylat med 2 ~ 4 C- tomer i alkylgruppen, c) polyoler eller polyetergïe¥~(n hydroxylgrupper) och n mol av ett diisocyanat, i efterhand omsatt med n mol av ett hydroxi- alky1(met)akrylat med 2 - 4 C-atomer i alkylgruppen (n = 3 - 6), d) mättade eller omättade polyestrar med n fria hydroxylgrupper och n mol av ett diisocyanat, i efterhand omsatt med n mol av ett hydroxialkyl(met)akrylat med 2 - 4 C-atomer i alkyl- gruppen (n = 2 - 6).In the unsaturated polyester resins, up to 50 mol% of the unsaturated incondensed dicarboxylic acids can be replaced by other dicarboxylic acid units such as phthalic acid, isophthalic acid, 3,6-dichlorophthalic acid, tetrachlorophthalic acid, hexahydrophthalic acid, succinic acid and adipic acid. 7803474-1 X) urethane acrylates, obtained from: a) diisocyanates (1 mol) and 2 moles of hydroxyalkyl (meth) acrylates having 2 to 4 C atoms in the alkyl group, b) glycols or polyether glycols (1 mol) and 2 moles of a di isocyanate, subsequently reacted with 2 moles of a hydroxyalkyl (meth) acrylate having 2 to 4 C-tomers in the alkyl group, c) polyols or polyethergyl (n hydroxyl groups) and n moles of a diisocyanate, subsequently reacted with n mol of a hydroxyalkyl (meth) acrylate having 2 to 4 C atoms in the alkyl group (n = 3 - 6), d) saturated or unsaturated polyesters having n free hydroxyl groups and n mol of a diisocyanate, subsequently reacted with n mol of a hydroxyalkyl (meth) acrylate having 2 to 4 C atoms in the alkyl group (n = 2 - 6).
Kolkedjorna hos glykolerna, polyeterglykolerna, polyolerna eller polyeterpolyolerna kan vara avbrutna av l eller flera kväve- atomer.The carbon chains of the glycols, polyether glycols, polyols or polyether polyols may be interrupted by one or more nitrogen atoms.
XI) polyepoxipolyakrylater, d.v.s. omsättningsprodukter av polyepoxi- der och en eteniskt omättad monokarbonsyra såsom (met)akrylsyra, varvid 60 - 100 %, företrädesvis 100 %, av epoxigrupperna har omsatts.XI) polyepoxy polyacrylates, i.e. reaction products of polyepoxides and an ethylenically unsaturated monocarboxylic acid such as (meth) acrylic acid, 60-100%, preferably 100%, of the epoxy groups having been reacted.
Med polyepoxider skall i föreliggande sammanhang förstås föreningar, vilka innehåller mer än en 1,2-epoxigrupp per molekyl, fö- reträdesvis 2 - 6 och speciellt 2 epoxigrupper.In the present context, polyepoxides are to be understood as meaning compounds which contain more than one 1,2-epoxy group per molecule, preferably 2 to 6 and especially 2 epoxy groups.
De till användning kommande polyepcxiföreningarna kan vara polyglycidyletrar av flervärda fenoler, exempelvis från pyrokatekin, resorcin, hydrokinon, från 4,4'~dihydroxidifenylmetan, från 4,4'-di- hydroxi-3,3'-dimetyldifenylmetan, från 4,4'-dihydroxidifenyldimetyl- metan (Bisfenol A), från 4,4'~dihydroxidifenylmetylmetan, från 4,4'- dihydroxidifenylcyklohexan, från 4,4'-dihydroxi-3,3'-dimetyldifeny1- propan, från 4,4'-dihydroxidifenyl, från 4,4'-dihydroxidifenylsulfon, från tris-(4-hydroxifenyl)-metan, från klorerings- och bromeringspro- dukter av de ovan nämnda difenolerna, speciellt från Bisfenol A, vidare från novolacker (d.v.s. från omsättningsprodukter av envärda eller flervärda fenoler med aldehyder, speciellt formaldehyd, i närvaro av sura katalysatorer), från difenoler, vilka erhållits genom förestring av 2 mol av natriumsaltet av en aromatisk oxikarbonsyra med l mol av en dihalogenalkan eller dihalogendialkyleter (jämför brittiska patent- _--...4,..._-..........__.. ...n -_ . _, man., __... 78034-74-1 l skriften l 017 612), från polyfenoler, vilka erhållits genom konden- sation av fenoler och långkedjiga, åtminstone 2 halogenatomer innehål- lande halogenparaffiner (jämför brittiska patentskriften l 024 288).The polyepxy compounds to be used may be polyglycidyl ethers of polyhydric phenols, for example from pyrocatechin, resorcinol, hydroquinone, from 4,4'-dihydroxydiphenylmethane, from 4,4'-dihydroxy-3,3'-dimethyldiphenylmethane, from 4,4 ' -dihydroxydiphenyldimethylmethane (Bisphenol A), from 4,4'-dihydroxydiphenylmethylmethane, from 4,4'-dihydroxydiphenylcyclohexane, from 4,4'-dihydroxy-3,3'-dimethyldiphenyl-propane, from 4,4'-dihydroxydiphenyl, from 4,4'-dihydroxydiphenylsulfone, from tris- (4-hydroxyphenyl) -methane, from chlorination and bromination products of the abovementioned diphenols, in particular from Bisphenol A, further from novolaks (ie from reaction products of monohydric or polyhydric phenols with aldehydes, especially formaldehyde, in the presence of acid catalysts), from diphenols, which are obtained by esterification of 2 moles of the sodium salt of an aromatic oxycarboxylic acid with 1 mole of a dihaloalkane or dihalo dialkyl ether (compare British patents). .._-..........__ .. ... n -_. _, man., __... 78034-74-1 in the specification l 017 612), from polyphenols obtained by condensation of phenols and long-chain, at least 2 halogen atoms containing halogenated paraffins (see British Patent Specification 1 024 288) .
Vidare kan nämnas glycidyletrar av flervärda alkoholer, exempelvis från 1,4-butandiol, 1,4-butendiol, glycerin, trimetylol- propan, pentaerytrit och polyetylenglykoler.Mention may also be made of glycidyl ethers of polyhydric alcohols, for example from 1,4-butanediol, 1,4-butenediol, glycerin, trimethylolpropane, pentaerythritol and polyethylene glycols.
Av intresse är även triglycidylisocyanurat, N,N'-diepoxi- propyloxiamid, polyglycidyltioetrar från flervärda tioler, exempelvis från bismerkaptometylbensen, diglycidyl-trimetylentrisulfon, epoxide- rad polybutadien, epoxiderad linolja och vinylcyklohexendiepoxid.Also of interest are triglycidyl isocyanurate, N, N'-diepoxypropyloxyamide, polyglycidylthioethers from polyvalent thiols, for example from bismercaptomethylbenzene, diglycidyl-trimethylene trisulfone, epoxidized polybutadiene, epoxidized linseed oil and vinyl epoxy cyclohex.
Dessutom kommer följande föreningar ifråga: glycidylestrar av flervärda aromatiska, alifatiska och cykloalifatiska karbonsyror, exempelvis ftalsyradiglycidylester, tereftalsyradiglycidylester, tetra- hydroftalsyradiglycidylester, adipinsyra-diglycidylester, hexahydro~ ftalsyradiglycidylester, som eventuellt kan vara substituerade med metylgrupper och glydicylestrar av omsättningsprodukter av l mol av en aromatisk eller cykloalifatisk dikarbonsyraanhydrid och en halv mol av en diol respektive l/n mol av en polyol med n hydroxylgrupper, t.ex. glycidylkarbonsyraestrar med den allmänna formeln O n CH C Q-cxaa-cnz-o- / 0 n där A betecknar en åtminstone 2-värd rest av ett eventuellt av syre och/eller cykloalifatiska ringar avbrutet alifatiskt kolväte eller en 2-värd rest av ett cykloalifatiskt kolväte, R betecknar väte eller alkylrester med l - 3 C-atomer och n betecknar ett tal mellan 2 och 6, eller blandningar av glycidylkarbonsyraestrar enligt den angivna all- männa formeln (jämför brittiska patentskriften l 220 702).In addition, the following compounds are possible: glycidyl esters of polyhydric, aliphatic and cycloaliphatic carboxylic acid polyhydric acids, for example phthalic acid diglycidyl ester, terephthalic acid diglycidyl ester, tetrahydrophthalic acid diglycidyl ester, adipic acid diglycidyl ester and hexahydrocyclic acid substituent; or cycloaliphatic dicarboxylic anhydride and half a mole of a diol and 1 / n mole of a polyol having n hydroxyl groups, e.g. glycidyl carboxylic acid esters of the general formula O n CH C Q-cxaa-cnz-o- / 0 n where A represents an at least 2-valent residue of an aliphatic hydrocarbon interrupted by oxygen and / or cycloaliphatic rings or a 2-valent residue of a cycloaliphatic hydrocarbon, R represents hydrogen or alkyl radicals having 1 to 3 carbon atoms and n represents a number between 2 and 6, or mixtures of glycidyl carboxylic acid esters according to the general formula given (compare British Patent Specification 1,220,702).
Föredragna polyepoxiföreningar är polyglycidyletrar av Bisfenol A och polyglycidylestrar av hexahydroftalsyra, som eventuellt på förhand förlängts med en dikarbonsyra, exempelvis adipinsyra, bärn- stenssyra, isoftalsyra eller maleinsyra eller med ammoniak, aminer el- ler H25, ditioler eller polytioler.Preferred polyepoxy compounds are polyglycidyl ethers of Bisphenol A and polyglycidyl esters of hexahydrophthalic acid, which may be pre-extended with a dicarboxylic acid, for example adipic acid, succinic acid, isophthalic acid or maleic acid or with ammonia, amines or polytiol or H25, dithiols.
Förförlängningen kan exempelvis ske med 0,01 - 0,5 NH-ekvi- valenter, räknat på epoxiekvivalent, av ammoniak eller en alifatisk eller cykloalifatisk primär eller sekundär amin eller en blandning av 7803474-1 r de nämnda kväveföreningarna. _ Om förförlängningen företas med hjälp av svavelföreningar kan 0,01 - 0,6 SH-ekvivalenter, räknat per l epoxiekvivalent, svavel- väte, alifatiska eller cykloalifatiska, aromatiska eller aralifatiska ditioler eller polytioler eller av en blandning av de nämnda svavel- föreningarna insättas.The elongation can take place, for example, with 0.01 - 0.5 NH equivalents, calculated on epoxy equivalent, of ammonia or an aliphatic or cycloaliphatic primary or secondary amine or a mixture of the mentioned nitrogen compounds. If the extension is carried out with the aid of sulfur compounds, 0,01 - 0,6 SH equivalents, calculated per epoxy equivalent, hydrogen sulphide, aliphatic or cycloaliphatic, aromatic or araliphatic dithiols or polytioles or of a mixture of the said sulfur compounds .
Om slutligen en förförlängning företas med åikarbonsyror - även tri- och flerfunktionella polykarbonsyror kan-under vissa om- ständigheter insättas - rör sig mängden likaledes mellan 0,01 och 0,6 karboxylekvivalenter per l epoxiekvivalent.Finally, if a pre-extension is carried out with acarboxylic acids - even tri- and multifunctional polycarboxylic acids can - under certain circumstances be used - the amount also ranges between 0.01 and 0.6 carboxyl equivalents per 1 epoxy equivalent.
Denna förförlängning kan ske genom en enkel omsättning vid rumstemperatur eller höjd temperatur då det gäller ammoniak, aminerna och SH-föreningar respektive vid höjd temperatur då det gäller karbon- syran. De förförlängda epoxiföreningarna utgör alltid polyepoxider med mer än en 1,2-epoxigrupp och är kända genom litteraturen.This pre-extension can take place by a simple reaction at room temperature or elevated temperature in the case of ammonia, the amines and SH compounds and at elevated temperature in the case of the carbonic acid. The pre-extended epoxy compounds always constitute polyepoxides with more than one 1,2-epoxy group and are known in the literature.
Speciellt föredragna som fotopolymeriserbara polyepoxipoly- akrylater är omsättningsprodukter av en polyepoxid med mer än en 1,2- epoxigrupp per molekyl vilkas epoxigrupper a) omsatts med 0,01 - 0,5 NH-ekvivalenter, räknat per l epoxiekvi- valent, ammoniak eller av en alifatisk eller cykloalifatisk pri- mär eller sekundär amin eller en aminokarbonsyra eller en bland- ning av de nämnda kväveföreningarna, företrädesvis ammoniak, med efterföljande omsättning med b) 0,40 - 0,90 karboxylekvivalenter, räknat per 1 epoxiekvivalent av akryl- eller metakrylsyra eller av en blandning av akryl- och metakrylsyra, och sedan efterföljande omsättning med c) 0,09 - 0,50 karboxylekvivalenter, räknat per 1 epoxigrupp, av en mättad alifatisk Cl- C12-, eller av en cykloalifatisk eller av en aromatisk C6- C20-karbonsyra, så att minst 80 % av från början befintliga epoxigrupper omsatts vid dessa tre delsteg.Particularly preferred as photopolymerizable polyepoxy polyacrylates are reaction products of a polyepoxide having more than one 1,2-epoxy group per molecule whose epoxy groups are a) reacted with 0.01 - 0.5 NH equivalents, calculated per 1 epoxy equivalent, ammonia or of an aliphatic or cycloaliphatic primary or secondary amine or an aminocarboxylic acid or a mixture of the said nitrogen compounds, preferably ammonia, with subsequent reaction with b) 0.40 - 0.90 carboxyl equivalents, calculated per 1 epoxy equivalent of acrylic or methacrylic acid or of a mixture of acrylic and methacrylic acid, and then subsequent reaction with c) 0,09 - 0,50 carboxyl equivalents, calculated per 1 epoxy group, of a saturated aliphatic C1-C12-, or of a cycloaliphatic or of an aromatic C6- C20 carbonic acid, so that at least 80% of the initially existing epoxy groups are reacted in these three sub-steps.
Omsättningen med kvävekomponenten sker vid 20 ~ 900 C och med (met)akrylsyran respektive karbonsyrorna c) vid 40 - 90°C, alltid i massa eller i inerta organiska lösningsmedel, varvid beträffande kom- ponenterna b) och c) även 0,0l - 3 vikt-%, räknat på utgångsepoxid, av katalysatorer såsom tert.-aminer, alkalisalter av organiska karbon- syror, alkalihydroxider, fosfiner, arsiner eller stibiner kan tillsät- tas. 7803474-1 F De uppräknade fotopolymeriserbara monomererna A) från grupperna I - XI kan blandas med varandra på godtyckligt sätt i varje önskat mängdförhållande, varvid exempelvis monomerer från gruppen IX blandas med monomerer från grupperna I - IV eller monomerer från grup~ pen III med sådana från grupperna I, II och IV. Föredragna är dock polyepoxipolyakrylaterna från grupp XI ensamma eller i kombination med monomerer från minst en av grupperna I - IV och VIII.The reaction with the nitrogen component takes place at 20 DEG-900 DEG C. and with the (meth) acrylic acid and the carboxylic acids, respectively, c) at 40 DEG-90 DEG C., always in bulk or in inert organic solvents, with regard to components b) and c) also 0,01 - 3% by weight, based on starting epoxide, of catalysts such as tert-amines, alkali salts of organic carboxylic acids, alkali hydroxides, phosphines, arsines or stibines can be added. The enumerated photopolymerizable monomers A) from groups I - XI can be mixed with each other in any desired ratio, for example monomers from group IX are mixed with monomers from groups I - IV or monomers from group III with such from groups I, II and IV. Preferred, however, the polyepoxy polyacrylates from group XI alone or in combination with monomers from at least one of groups I - IV and VIII.
Genom mångfald av blandningsmöjligheter kan man beroende av syftet med beläggningen inställa olika fysikaliska egenskaper.Due to the variety of mixing possibilities, different physical properties can be set depending on the purpose of the coating.
Som aminoplasthartser B) insättes exempelvis följande: karbamidaldehydhartser, vilka erhålles på känt sätt genom kondensation av karbamid eller karbamidderivat och aldehyder såsom formaldehyd, acetaldehyd o.s.v., företrädesvis i närvaro av Cl- C5-monoalkoholer.As aminoplast resins B) are used, for example, the following: urea aldehyde resins, which are obtained in a known manner by condensation of urea or urea derivatives and aldehydes such as formaldehyde, acetaldehyde, etc., preferably in the presence of C1-C5 monoalcohols.
Nämnas må aminotriazinaldehydhartser, vilka erhålles på i och för sig känt sätt genom kondensation av aminotriaziner, speciellt melamin, med en aldehyd såsom formaldehyd, acetaldehyd, bensaldehyd och liknande, i synnerhet formaldehyd, företrädesvis i närvaro av en lägre alkohol såsom metanol, etanol, propanol eller butanol. Sådana produkter finns även i handeln, exempelvis hexametoximetylmelamin.Mention may be made of aminotriazinaldehyde resins which are obtained in a manner known per se by condensation of aminotriazines, in particular melamine, with an aldehyde such as formaldehyde, acetaldehyde, benzaldehyde and the like, in particular formaldehyde, preferably in the presence of a lower alcohol such as methanol, ethanol, propanol or butanol. Such products are also commercially available, for example hexamethoxymethylmelamine.
Som fotoinitiatorer, vilka är fria från sura grupper, som vid fotopolymerisationen frigör syror, kan exempelvis nämnas: benso- fenon samt helt allmänt aromatiska ketoföreningar, vilka härledes från bensofenon, exempelvis alkylbensofenoner, halogenmetylerade bensofe- noner enligt tyska Offenlegungsschrift l 949 0lO, Michlers Keton, antron, halogenerade bensofenoner. Likaledes verksamma fotoinitiatorer utgöres av xanton och tioxanton samt antrakinon och talrika av deras derivat, exempelvis ß-metylantrakinon, tert.-butylantrakinon, tert.- butylantrakinon- och antrakinonkarbonsyraestrar, likaså oximestrar en- 7 ligt tyska Offenlegungsschrift l 795 089. Vidare lämpar sig bensoin och dess derivat såsom bensoindimetylketal, :L-hydroximetylbensoin, dl- hydroximetylbensoinmetyleter, ckrhydroxylmetylbensoinetyleter, eC~acetoximetyl-bensoin-metyleter, QL-(2-dietylfosfonetyl)-bensoin- etyleter, bensil-di-(2-dietylfosfonetyl)-ketal, bensiletylenketal, 2- fenyl-2-metoxi-4-bensoyl-4-fenyl-l,3-dioxolan och ytterligare derivat av bensoin, t.ex. enligt tyska Offenlegungsschrifter l 769 168, l 759 853, l 769 854, l 807 297, l 807 301, l 919 678 och tyska ut- läggningsskriften l 694 l49. 7803474-1 r Speciellt föredragna är bensofenon och bensoinderivat med den allmänna formeln 0 ll C Ar / \ 132/ Ar C I O I Rl där Ar = en osubstituerad eller med alkyl, alkoxi, halogen substituerad aromatisk rest; Rl = rakkedjig eller grenad alkylrest med (Cl- C12), aryl såsom fenyl, cykloalkyl såsom cyklohexyl, tetrahydropyranyl, l-metoxietyl; R2 = alkoxi med 1 - 6 C-atomer, allyl, bensyl, som eventuellt är sub- stituerad med halogen, eller resten -CH2-CH2-X, varvid X = CN, CONHZ, COOR3 och PO(OR4)2, varvid R3 = H, lägre alkyl (C1- C10), R4 = alkyl (Cl- C6), eller R1 och R2 kan vara förenade med varandra under bildning av en eventuellt substituerad 1,3-dioxolan-ring.Examples of photoinitiators which are free from acidic groups which release acids during the photopolymerization are benzophenone and, in general, aromatic keto compounds which are derived from benzophenone, for example alkylbenzophenones, halomethylated benzophenones according to German Offenlegungsschrift 1 949 0lO , anthron, halogenated benzophenones. Likewise active photoinitiators consist of xanthone and thioxanthone as well as anthraquinone and numerous of their derivatives, for example β-methylanthraquinone, tert-butylanthraquinone, tert-butylanthraquinone and anthraquinone carboxylic acid esters, as well as oxime esters according to German Offenlegungsenschrift and its derivatives such as benzoindimethyl ketal,: L-hydroxymethylbenzoin, dl-hydroxymethylbenzoin methyl ether, dihydroxylmethylbenzoethyl ether, eC , 2-phenyl-2-methoxy-4-benzoyl-4-phenyl-1,3-dioxolane and further derivatives of benzoin, e.g. according to German Offenlegungsschrifter l 769 168, l 759 853, l 769 854, l 807 297, l 807 301, l 919 678 and the German outsourcing letter l 694 l49. Particularly preferred are benzophenone and benzoin derivatives of the general formula O 11 C Ar / \ 132 / Ar C I O I R 1 where Ar = an unsubstituted or with alkyl, alkoxy, halogen substituted aromatic radical; R 1 = straight-chain or branched alkyl radical with (C 1 -C 12), aryl such as phenyl, cycloalkyl such as cyclohexyl, tetrahydropyranyl, 1-methoxyethyl; R 2 = alkoxy having 1 to 6 C atoms, allyl, benzyl, which is optionally substituted by halogen, or the residue -CH 2 -CH 2 -X, where X = CN, CONH 2, COOR 3 and PO (OR 4) 2, wherein R 3 = H, lower alkyl (C 1 -C 10), R 4 = alkyl (C 1 -C 6), or R 1 and R 2 may be joined together to form an optionally substituted 1,3-dioxolane ring.
Företrädesvis betyder Ar = fenyl, Rl en rakkedjig eller grenad alkylrest med 1 - 4 C-atomer och R2 = allyl eller resten -CH2-CH2-X, där X = CN och COOR3, varvid R3 = Cl- C4-alkyl.Preferably Ar = phenyl, R1 represents a straight chain or branched alkyl radical having 1 to 4 carbon atoms and R2 = allyl or the radical -CH2-CH2-X, where X = CN and COOR3, where R3 = C1-C4-alkyl.
Lämpade föreningar av denna typ (jämför tyska Offenle- gunsschrift l 769 854) är exempelvis följande: cL~allylbensoinmetyleter, Ckrallylbensoinisopropyleter, 0\-allyl- bensøinetyleter, cL-allylbensoinbutyleter, Ck-allylbensoinpropyleter, Ckfallylbensoinoktyleter, U,-allylbensoindodecyleter, cL-bensyl- bensoinmetyleter, CL-bensylbensoinetyleter, bL-bensylbensoinpropyl- eter, DL-bensylbensoinisopropyleter, Ck-bensylbensoinbutyleter, <$-42-cyanetyl)-bensoinmetyleter, :L-(2~cyanetyl)-bensoinetyleter, GL-(2-cyanetyl)-bensoinpropyleter, Ck-(2-byanetyl)-bensoinbutyleter, ¿g-(2-cyanetyl)-bensoinisopropyleter, ck-(2-cyanetyl)-bensoinisobuty1- eter, ot-(2-cyanetyl)-bensoinhexyleter, C4-(2-cyanetyl)-bensoinokty1- eter, go-(2-cyanetyl)-bensoindodecyleter, =(-(2-cyanetyl)-bensoin- isooktyleter, ed-(2-karboxietyl)-bensoinmetyleter, fiß-(2-karboxietyl)- bensoinetyleter, Cá-(2-karboxietyl)-bensoinpropyleter, n&-(2-karboxi- 7803474-1 10 r etyl)-bensoinisopropyleter, ={;(2-karboxietyl)-bensoinbutyleter, Ck-(2-karboxietyl)-bensoinisobutyleter, :L-(2-karboxietyl)-bensoin- hexyleter,' GL-(2-karboxietyl)-bensoinøktyleter, üb-(2-karboxietyl)- bensoindodecyleter, Gå-(2¥karboxiety1)-bensoinisooktyleter, CXr(2- karbometoxietyl)-bensoinmetyleter, UQ-(2-karbometoxietyl)-bensoin- etyleter, ck-(2-karbometóxietyl)-bensoinpropyleter, Ch-(2-karbo- metoxietyl)-bensoinisopropyleter} cb-(2-karbometoxietyl)-bensoinbuty1- eter, vk-(2-karbometoxietyl)-bensoiniscbutyleter, °§-(2-karbometoxi- etyl)-bensoinhexyleter, Gh-(2-karbometoxietyl)-bensoinoktyleter, WL-(2-karbometoxietyl)-bensoindodecyleter, n&-(2-karbcmetQxietyl)- bensoinisooktyleter, Ci-(2-karboetoxietyl)-bensoinmetyleter, EL-(2- karboetoxietyl)-bensoinetyleter, cä-(2-karboetoxietyl)-bensoinpropyl- eter, EL-(2-karboetoxietyl)-bensoinisopropyleter, .c\;(2-karboetoxi- etyl)-bensoinbutyleter, ok-(2-karboetoxietyl)-bensoinisobutyleter, DL-(2-karboetoxietyl)-bensoinhexyleter, CL;(2-karboetoxietyl)-bensoin- oktyleter, Qi-(2-karboetoxietyl)~bensoindodecyleter, DÅ-(2-karboetoxi- etyl)~bensoinisooktyleter, GL-(2-karbopropoxietyl)-bensoinmetyleter, Ck-(2-karbopropoxietyl)-bensoinetyleter, <Å;(2-karbopropoxietyl)~ bensoinpropyletér, QR-(2-karbopropoxietyl)-bensoinisopropyleter, =&-(2-karbopropoxietyl)-bensoinbutyleter, \L-(2-karbopropoxietyl)- bensoinisobutyleter, karbopropoxietyl)-bensoinoktyleter, Oi-(2-karbcpropoxietyl)-bensoin- dodecyleter, =L-(2-karbopropoxietyl)-bensoinisooktyleter, °k-(2-karbo- n-butoxietyl)-bensoinmetyleter, Uk~(2-karbo-n-butoxietyl)-bensoin- etyleter, EL-(2-karbo-n-butoxietyl)-bensoinpropyleter, Qh-(2~karbo-n- butoxietyl)-bensoinisopropyleter, Ck-(2-karbo4n~butoxietyl)-bens0in- butyleter, Qi-(2-karbo-n-butoxietyl)-bensoinisobutyleter, C&-(2-karbo- n-butoxietyl)-bensoinhexyleter, “i-(2-karbo-n-butoxietyl)-bensoinokty1- eter, Ci:(2-karbo-n-butoxietyl)-bensoindodecyleter, =Lr(2-karbo-n- butoxietyl)-bensoinisooktyleter, ak-(2-karboisooktoxietyl)-bensoin- metyleter, Ck-(2-karboisooktoxietyl)-bensoinetyleter, 0<-(2-karboiso- oktoxietyl)-bensoinpropyleter, Ck-(2-karboixcoktoxietyl)-benscinisc- propyleter, ck-(2-karboisooktoxietyl)-bensoinbutyleter, %L-(2-karbo- isooktoxietyl)-bensoinisobutyleter, Uk-(2-karboisooktoxietyl)-bensoin- hexyleter, Ck-(2-karboisooktoxietyl)-bensoinoktyleter, cN-(2-karboiso- oktoxietyl)-bensoinäodecyleter, 51-(2-karboisooktoxietyl)-bensoin iso- oktyleter, GÅ-(2-karbonamidoetyl)-bensoinmetyleter, DL-(2-cyanetyl)- 7803474-1 ll F bensointetrahydropyranyleter, Ck-(2-cyanety1)-bensoin-(l-metoxietyl- eter, tå-(2~karbometoxiety1)-bensointetrahydropyranyleter, Ci-(2- karbetoxietyl)-bensoin-(1-metoxietyleter)-, Cß-(2-karbo-n-butoxietyl)- bensointetrahydropyranyleter, CK-(2-karbo-isooktoxietyl)-bensointetra- hydropyranyleter.Suitable compounds of this type (cf. German Offenlegunsschrift 1,769,854) are, for example, the following: C 1-6 allylbenzoin methyl ether, C 1-6 allylbenzoin isopropyl ether, C 1-4 allylbenzoylethyl ether, C 1-6 allylbenzoinbutyl ether, C benzoin methyl ether, CL-benzylbenzoethyl methyl ether, bL-benzylbenzoinpropyl ether, DL-benzylbenzoinisopropyl ether, C 1-4 benzylbenzoinbutyl ether, $- (42-cyanethyl) -benzoinomethyl ether, L- (2-cyanoethyl) -benzoethylethyl ether, GL- (2-cyanoethyl) - benzoinpropyl ether, C 1- (2-byanethyl) -benzoin butyl ether, α- (2-cyanethyl) -benzoinisopropyl ether, ck- (2-cyanethyl) -benzoin isobutyl ether, ot- (2-cyanethyl) -benzoinhexyl ether, C 4- (2- cyanethyl) -benzoinoxyethyl ether, go- (2-cyanethyl) -benzoindodecyl ether, = (- (2-cyanethyl) -benzoin-isooctyl ether, ed- (2-carboxyethyl) -benzoin methyl ether, ß ß- (2-carboxyethyl) -benzoethyl ether, C 1- (2-carboxyethyl) -benzoinpropyl ether, n & - (2-carboxyethyl) -benzoinisopropyl ether, = {; (2-carboxyethyl) -benzoinbutyl ether, C 1- (2-carboxyethyl) -benzoin isobutyl ether, L- (2-carboxyethyl) -benzoene-hexyl ether, GL- (2-carboxyethyl) -benzoinoctyl ether, β- (2-carboxyethyl) -benzoindodecyl ether, Ga- (2 ¥ carboxyethyl) ) -benzoin isooctyl ether, CXr (2-carbomethoxyethyl) -benzoinomethyl ether, UQ- (2-carbomethoxyethyl) -benzoin-ethyl ether, ck- (2-carbomethoxyethyl) -benzoinpropyl ether, Ch- (2-carbomethoxyethyl) -benzoinisopropyl ether} cb- ( 2-Carbomethoxyethyl) -benzoinobutyl ether, vk- (2-carbomethoxyethyl) -benzoiniscbutyl ether, N- (2-carbomethoxyethyl) -benzoinhexyl ether, Gh- (2-carbomethoxyethyl) -benzoin octyl ether, WL- (2-carbomethoxyethyl) - benzoindodecyl ether, n- - (2-carbomethoxyethyl) benzoin isoctyl ether, C1- (2-carboethoxyethyl) benzoethyl methyl ether, EL- (2-carboethoxyethyl) benzoethyl methyl ether, ca- (2-carboethoxyethyl) benzoin propyl ether, EL- (2-carboethoxyethyl) ) -benzoinisopropyl ether, (C- (2-carboethoxyethyl) -benzoinbutyl ether, ok- (2-carboethoxyethyl) -benzoin isobutyl ether, DL- (2-carboethoxyethyl) -benzoinhexyl ether, CL; (2-carboethoxyethyl) -benzoic octyl ether, Q- (2-carboethoxyethyl) -benzoindodecyl ether, DÅ- (2-carboethoxyethyl) -benzoinisooctyl ether, GL- (2-carbopropoxyethyl) -benzoinomethyl ether, Ck- (2-carbopropoxyethyl) -benzoethylethyl ether, <Å; (2-carbopropoxyethyl) -benzoinpropyl ether, QR- (2- carbopropoxyethyl) -benzoinisopropyl ether, = & - (2-carbopropoxyethyl) -benzoinbutyl ether, \ L- (2-carbopropoxyethyl) -benzoin isobutyl ether, carbopropoxyethyl) -benzoin octyl ether, O- (2-carbopropoxyethyl) -benzoin-dodecyl carbopropoxyethyl) -benzoin isooctyl ether, ° k- (2-carbon-n-butoxyethyl) -benzoin methyl ether, Uk- (2-carbon-n-butoxyethyl) -benzoyl ethyl ether, EL- (2-carbo-n-butoxyethyl) -benzoin propyl ether, Qh- (2-Carbo-n-butoxyethyl) -benzoinisopropyl ether, Ck- (2-carbonyl-butoxyethyl) -benzoin-butyl ether, Q- (2-carbon-n-butoxyethyl) -benzoinisobutyl ether, C1- (2-carbonyl) -butoxyethyl) -benzohexyl ether, “i- (2-carbo-n-butoxyethyl) -benzooxyethyl ether, C1: (2-carbo-n-butoxyethyl) -benzoindodecyl ether, = Lr (2-carbo-n-butoxyethyl) -benzoin isooctyl ether , α- (2-carboisooctoxyethyl) -benzoin-methyl ether, Ck- (2-carboisooctoxyethyl) -benzoethylethyl ether oiso-octoxyethyl) -benzoinpropyl ether, Ck- (2-carboisococtoxyethyl) -benzincisc-propyl ether, ck- (2-carboisooctoxyethyl) -benzoin butyl ether,% L- (2-carboisooctoxyethyl) -benzoin isobutyl ether, Uk- (2-carboisloxy) benzoin-hexyl ether, C 1- (2-carboisooctoxyethyl) -benzoin octyl ether, cN- (2-carboisooctoxyethyl) -benzoeneodecyl ether, 51- (2-carboisooctoxyethyl) -benzoin isooctyl ether, GÅ- (2-carbonamidoethyl) -benzoinomethyl ether - (2-cyanethyl) - 7803474-1 II F benzointetrahydropyranyl ether, C 1- (2-cyanoethyl) -benzoene- (1-methoxyethyl ether, toe- (2-carbomethoxyethyl) -benzoentetrahydropyranyl ether, C 1- (2-carbethoxyethyl) benzo - (1-methoxyethyl ether) -, Cβ- (2-carbo-n-butoxyethyl) -benzoentetrahydropyranyl ether, CK- (2-carbo-isooctoxyethyl) -benzointetetrahydropyranyl ether.
Som fotoinitiatorer, vilka frigör syror under inverkan av energirik strålning, kan exempelvis nämnas: QL-metylol-bensoin-sulfonsyraestrar med den allmänna formeln m (EHZ-O-SOZ R Ar-C-C-Ar ll I J' O ORl n där R = lägre alkyl eller aryl eller alkylen eller tvåvärd arømatisk rest, Rl = H eller lägre alkylrest, Ar och Arl = lika eller olika, eventuellt alkyl-, alkoxi~ eller halogensub- stituerade aromatiska rester och n = l eller 2.As photoinitiators, which release acids under the influence of energy-rich radiation, there can be mentioned, for example: QL-methylol-benzoin-sulfonic acid esters of the general formula m (EHZ-O-SOZ R Ar-CC-Ar ll IJ 'O ORl n where R = lower alkyl or aryl or alkylene or divalent aromatic radical, R 1 = H or lower alkyl radical, Ar and Ar 1 = the same or different, optionally alkyl-, alkoxy- or halogen-substituted aromatic radicals and n = 1 or 2.
Sådana fotoinitiatorer är kända genom DT-OS l 919 678.Such photoinitiators are known from DT-OS 1 919 678.
I ovan angivna formel betyder R företrädesvis alkyl med 1 - 6 C-atomer, fenyl, fenyl som är substituerad med Cl- C4-alkyl, naftyl, alkylen med 2 - 6 C-atomer, vidare resten Ü Q, , varvid A A1 betecknar ÉHB E' .. -c- , -c-, -s-, -oc-o-, -cH2-, -cn-, -Cn- í ll II I I CH3 o o CH3 C235 Rl = H eller alkyl med l - 4 C-atomer; Ar och/eller Arl = fenyl, fenyl substituerad med alkyl med l - 4 C-atomer, med alkoxi med l - 4 C-at0- mer, med klor och/eller brom. 78054"4-1 12 F Som specifika exempel kan nämnas: ß«-hydroximetylbensoin- metansulfonsyraester, -bensensulfonsyraester, -p-toluensulfonsyraester *och -'P-naftalensulfonsyraester, Ck-hydroximetyl-4,4'-dimetylbensoin- bensensulfonsyraester, QL-hydroximetyl-4,4'-diklorbensoinbensensulfon~ syraester, Ckrhydroximetylbensoin-isopropyleter-bensensulfonsyraester och bis-(QL-hydroximetylbensoin)-difenylmetan-4,4'-disulfonat. Även om det är möjligt att applicera beläggningsmedlen en- ligt uppfinningen även utan ytterligare utspädning med lösningsmedel är det givetvis i och för inställning av önskad viskositet möjligt att göra en blandning med inerta lösningsmedel såsom butylacetat, etyl- acetat, etanol, isopropanol, butanol, aceton, etylmetylketon, dietyl- keton, cyklohexan, cyklohexanon, cyklopentan, cyklopentanon, n-heptan, n-hexan, n-oktan, isooktan, toluen, xylen, metylenklorid, kloroform, l,1+dikloretan, 1,2-dikloretan, l,l,2-trikloretan, koltetraklorid.In the above formula, R preferably represents alkyl having 1 to 6 C atoms, phenyl, phenyl substituted with C 1 -C 4 alkyl, naphthyl, alkylene having 2 to 6 C atoms, further the residue Ü Q 1, wherein A represents A 1 EHB E '.. -c-, -c-, -s-, -oc-o-, -cH2-, -cn-, -Cn- II II II CH3 oo CH3 C235 R1 = H or alkyl with 1- 4 C atoms; Ar and / or Ar 1 = phenyl, phenyl substituted by alkyl having 1 to 4 C atoms, with alkoxy having 1 to 4 C atoms, with chlorine and / or bromine. 78054 "4-1 12 F Specific examples may be mentioned: β« -hydroxymethylbenzoin-methanesulfonic acid ester, -benzenesulfonic acid ester, -p-toluenesulfonic acid ester * and -'P-naphthalenesulfonic acid ester, Ck-hydroxymethyl-4,4'-dimethylbenzoene-benzenesulfonic acid ester, hydroxymethyl-4,4'-dichlorobenzoinbenzenesulfonic acid ester, C-hydroxymethylbenzoin-isopropylether-benzenesulfonic acid ester and bis- (QL-hydroxymethylbenzoin) -diphenylmethane-4,4'-disulfonate Although it is possible to apply the coating compositions according to the invention even without further dilution with solvents it is of course possible to make a mixture with inert solvents such as butyl acetate, ethyl acetate, ethanol, isopropanol, butanol, acetone, ethyl methyl ketone, diethyl ketone, cyclohexane, cyclohexanone, cyclopentane, n cyclopentane, for the adjustment of the desired viscosity -heptane, n-hexane, n-octane, isooctane, toluene, xylene, methylene chloride, chloroform, 1,1 + dichloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, carbon tetrachloride.
För erhållande av för bearbetning lämplig viskositet kan man tillsätta 0-- 50 vikt-%, företrädesvis 2 - 40 vikt-%, lösningsmedel, räknat på blandningen-av A)-+ B) + C) och lösningsmedel.To obtain a viscosity suitable for processing, it is possible to add 0-50% by weight, preferably 2 to 40% by weight, of solvents, based on the mixture of A) - + B) + C) and solvents.
Fördelaktiga tillsatser, som kan leda till en höjning av reaktiviteten, är vissa tertiära aminer såsom trietylamin och tri- etanolamin. Pâ liknande sätt verksam är en tillsats av merkaptoföre- ningar såsom dodecylmerkaptan, tioglykolsyraester, tiofenol eller mer- kaptoetanol. De nämnda substanserna insättes företrädesvis i mängder av 0 - 5 vikt-%, räknat på polymeriserbara komponenter.Advantageous additives which can lead to an increase in reactivity are certain tertiary amines such as triethylamine and triethanolamine. Similarly effective is an addition of mercapto compounds such as dodecyl mercaptan, thioglycolic acid ester, thiophenol or mercaptoethanol. The substances mentioned are preferably used in amounts of 0 to 5% by weight, based on polymerizable components.
Som bestrâlningskälla för genomföringen av fotopolymerisa- tionen kan man använda konstgjord bestrålning, vars emission ligger inom området 2500 - 5000 Ä,:företrädesvis 3000 - 4000 Å. Fördelaktiga är kvicksilverånglampor, xenonlampor och wolframlampor, speciellt kvicksilverhögtrycksbestrâlare. Fotopolymerisationen kan genomföras vid rumstemperatur eller vid höjda temperaturer (cirka 20 - l20° C).As a radiation source for carrying out the photopolymerization, artificial radiation can be used, the emission of which is in the range 2500 - 5000 Å, preferably 3000 - 4000 Å. Mercury vapor lamps, xenon lamps and tungsten lamps, especially mercury high-pressure radiators, are advantageous. The photopolymerization can be carried out at room temperature or at elevated temperatures (about 20 - 120 ° C).
Som regel kan skikten av blandningarna enligt uppfinningen med en tjocklek av mellan 1 fun och 0,1 mm (1 /nu = l0_3mm) härdas till en film, om de bestrålas med ljuset från en cirka 8 om avlägsen kvicksilverhögtryckslampa, exempelvis av typen HTQ-7 från Philips.As a rule, the layers of the mixtures according to the invention with a thickness of between 1 fun and 0.1 mm (1 / nu = 10_3mm) can be cured to a film, if they are irradiated with the light from an approximately 8 if distant mercury high pressure lamp, for example of the type HTQ- 7 from Philips.
Beroende av användningsändamâl kan beläggningarna efter genomförd bestrålning underkastas ytterligare värmebehandling vid tem- peraturer mellnn 80 och 1500 C i syfte att exempelvis uppnå större hårdhet eller bättre lösningsmedelsbeständighet.Depending on the purpose of use, the coatings can be subjected to further heat treatment after irradiation at temperatures between 80 and 1500 C in order, for example, to achieve greater hardness or better solvent resistance.
Om fyllmedel medanvänds vid tillämpningen av hartsmassorna 7803474-1 13 enligt uppfinningen som UV-ljus-härdande överdrag är deras insats be- gränsad till sådana, som genom sin absorptionsförmâga inte begränsar polymerisationsförloppet. Exempelvis kan man använda talk, tungspat, krita, gips, kiselsyror, asbestmjöl och lättspat som ljusgenomsläpp- liga fyllmedel. I mycket tunna skikt kan även TiO2 och kulörpigment medanvändas.If fillers are co-used in the application of the resin compositions according to the invention as UV light-curing coatings, their use is limited to those which, due to their absorbency, do not limit the polymerization process. For example, talc, tongue spatula, chalk, gypsum, silicic acids, asbestos flour and light spatula can be used as light-transmitting fillers. In very thin layers, TiO2 and color pigments can also be used together.
Appliceringen av överdragsmedlen på lämpade substrat kan ske medelst inom lackindustrin vanliga metoder såsom besprutning, valsning, rakling, tryckning, doppning, flödning, besprutning eller påpensling.The application of the coating agents to suitable substrates can take place by means of methods common in the paint industry, such as spraying, rolling, squeegeeing, printing, dipping, flowing, spraying or brushing.
Lämpade substrat är papper, kartong, läder, trä, plaster, textilier, keramiska material, metaller, företrädesvis dock papper och kartong samt trä och metall. Eftersom överdragsmedlen under UV- ljus under en tid av från bråkdelar av en sekund till några sekunder härdar till filmer med utmärkta mekaniska egenskaper är det exempelf vis möjligt att anpassa ett pappersbeläggningsförlopp till de inom tryckeribranschen vanliga bearbetningshastigheterna.Suitable substrates are paper, cardboard, leather, wood, plastics, textiles, ceramic materials, metals, preferably paper and cardboard as well as wood and metal. Since the coating compositions under UV light cure for a period of from fractions of a second to a few seconds into films with excellent mechanical properties, it is possible, for example, to adapt a paper coating process to the processing speeds common in the printing industry.
De i exemplen angivna viskositeterna fastställdes medelst DIN-4-bägare (4 mm dysa) enligt DIN 53 211 och definieras genom den i sekunder fastställda utströmningstiden. Procentuppgifter och delar hänför sig till vikten, såvida inte annat anges specifikt.The viscosities given in the examples were determined by means of DIN-4 cups (4 mm nozzle) according to DIN 53 211 and are defined by the outflow time determined in seconds. Percentages and parts are by weight unless otherwise indicated.
Utgångsmaterial 1 6800 g Bisfenol A-bisglycideter (epoxiekvivalent 190) värmdes i en 10 liters trehalskolv, försedd med omrörare, dropptratt och återloppskylare, till 600 C. Vid denna temperatur infördes 42,5 g (2,5 mol) gasformig ammoniak under loppet av 20 timmar i reaktionslös- ningen. Därefter tillsatte man 68,4 g tiodiglykol (katalysator) och 1386 g (l9,25 mol) akrylsyra vid 60° C under loppet av 2 timmar och i anslutning därtill 340 g (5,66 mol) ättiksyra droppvis under loppet av 30 minuter. Man efterrörde blandningen vid 600 C tills man uppnått ett syratal av 0 (titrering med n/10 Na0H/bromtymolblått), stabilise- rade med 0,05 vikt-% p-metoxifenol, räknat på erhållet harts, och kylda sedan till rumstemperatur.Starting material 1,6800 g of bisphenol A bisglycidates (epoxy equivalent 190) were heated in a 10 liter three-necked flask equipped with a stirrer, dropping funnel and reflux condenser to 600 DEG C. At this temperature 42.5 g (2.5 moles) of gaseous ammonia were introduced during the course of 20 hours in the reaction solution. Then 68.4 g of thiodiglycol (catalyst) and 1386 g (19.25 mol) of acrylic acid were added at 60 ° C over a period of 2 hours, followed by 340 g (5.66 mol) of acetic acid dropwise over the course of 30 minutes. The mixture was stirred at 60 DEG C. until an acid value of 0 was obtained (titration with n / 10 NaOH / bromothymol blue), stabilized with 0.05% by weight of p-methoxyphenol, based on the obtained resin, and then cooled to room temperature.
Utgångsmaterial 2 245 g glydicylester av grenade monokarbonsyror med 9 - ll C-atomer (epoxiekvivalent 245), 72 g (1 mol) akrylsyra och 3,2 q tri- etylbensylammoniumklorid rördes under överledning av luft under 12 timmar vid 90° C. Efter denna tid uppgick syratalet till värdet 2. 7803474-1 Exemoel l Man framställde en blandning från de i nedanstående ta- bell l angivna komponenterna och applicerade det erhållna beläggnings- medlet medelst en filmdragare med en tjocklek av 180 /1 på avfettade stålplåtar och bestrålade därefter på 6 cm avstånd med en UV-lampa (typ: Hanau Qu 500) under 60 sekunder. Därefter bestämde man klibb- frihet, acetonbeständighet, färg och vidhäftning. Resultaten har sam- manställts i tabell l.Starting material 2,245 g of glydicyl ester of branched monocarboxylic acids having 9 to 11 carbon atoms (epoxy equivalent 245), 72 g (1 mol) of acrylic acid and 3.2 g of triethylbenzylammonium chloride were stirred under air conduction for 12 hours at 90 ° C. time, the acid number was 2. 2.803474-1 Exemoel l A mixture was prepared from the components listed in Table 1 below and the resulting coating agent was applied by means of a film puller having a thickness of 180/1 on degreased steel sheets and then irradiated on 6 cm distance with a UV lamp (type: Hanau Qu 500) for 60 seconds. Then, freedom of tack, acetone resistance, color and adhesion were determined. The results have been compiled in Table 1.
Jämförelseförsök l - 5 Analogt med exempel 1 framställde man filmer från ett be- läggningsmedel utgående från de i tabell l angivna komponenterna och undersökta resultatet med avseende på klibbfrihet, acetonbeständighet, färg och vidhäftning.Comparative Experiments 1 - 5 In analogy to Example 1, films were prepared from a coating agent based on the components listed in Table 1 and the results were examined with respect to tack-freeness, acetone resistance, color and adhesion.
Eftersom jämförelseförsöken 2 och 3 efter 120 sekunder varaktighet UV-bestrålning fortfarande uppvisade klibbiga filmer av- stod man från fortsatt provning (se tabell 1).Since comparative experiments 2 and 3 after 120 seconds duration of UV radiation still showed sticky films, further testing was omitted (see Table 1).
Jämförelseförsök 4 och 5 ledde efter en bestrålningstid av 60 sekunder visserligen till klibbfria beläggningar med tämligen god acetonbeständighet och med jämförelseförsök 4 erhölls till och med färglösa filmer men dock uppvisade beläggningarna på basis av jämfö- relseförsöken 4 och 5 en dålig vidhäftning till underlaget.Comparative experiments 4 and 5, after an irradiation time of 60 seconds, admittedly led to tack-free coatings with fairly good acetone resistance and with comparative experiments 4 even colorless films were obtained, but the coatings on the basis of comparative experiments 4 and 5 showed poor adhesion to the substrate.
Av tabell l framgår att endast kombinationerna enligt upp- finningen av minst en fotopolymeriserbar- monomer, ett aminoplastharts och en fotoinitiatorkombination, av vilken en fotoinitiator under in- verkan av bestrålningen vid fotopolymerisationen bildade en syra, här- dade till beläggningar med goda egenskaper.Table 1 shows that only the combinations according to the invention of at least one photopolymerizable monomer, an aminoplastic resin and a photoinitiator combination, of which a photoinitiator under the influence of the irradiation during the photopolymerization formed an acid, cured to coatings with good properties.
Förklaring till tabellen: Klibbfrihet: Underlaget placerades med lackskiktet uppåt på en tarerad våg, som belastades med en motvikt av l kg. På lack- skiktet lades en liten fettfri vaddtuss med diameter 2 --3 cm och på denna placerades en liten metallskiva med diameter 2 cm. Man tryckte sedan med fingret mot skivan, tills vågen befann sig i jämvikt och vågen hölls i detta jämviktsläge under 10 sekunder. Efter avlägsnande av metallskivan försökte man avlägsna vaddtussen genom en försiktig blåsning. Lackskiktet var klibbfritt om tussen inte längre häftade vid lackskiktet och heller inga hår kvarblev på detsamma 7803474-1 15 Bestämning av acetonbeständighet: g På beläggningarna placerades 0,5 ml aceton och under sam- tidig ingnidning med fingret bragtes acetonet att förångas under lop- pet av cirka 5 sekunder. Om beläggningarna efter denna behandling fortfarande var klibbfria betecknades acetonbeständigheten som god.Explanation of the table: Non-sticking: The substrate was placed with the lacquer layer upwards on a tared scale, which was loaded with a counterweight of 1 kg. A small grease-free cotton ball with a diameter of 2 --3 cm was placed on the lacquer layer and a small metal plate with a diameter of 2 cm was placed on it. You then pressed your finger against the disc until the scale was in equilibrium and the scale was kept in this equilibrium position for 10 seconds. After removing the metal plate, an attempt was made to remove the wadding by a gentle blow. The lacquer layer was tack-free if in between no longer adhered to the lacquer layer and no hair remained on the same 7803474-1 15 Determination of acetone resistance: g 0.5 ml of acetone was placed on the coatings and the acetone was caused to evaporate during the run during simultaneous rubbing with the finger. of about 5 seconds. If the coatings after this treatment were still tack-free, the acetone resistance was described as good.
Om man däremot erhöll klibbande beläggningar betecknades acetonbe- ständigheten som dålig.On the other hand, if sticky coatings were obtained, the acetone resistance was described as poor.
Bestämning av vidhäftning: Den belagda plåtytan ritsades medelst en skarp kniv till ett X-formigt märke och därefter pressades en bit cellofan-klister- remsa mot detta X~formiga inristade märke och avdrogs sedan i syfte att bestämma om beläggningsfilmen kunde avlyftas från metallskikt- bäraren. Vidhäftningen betecknades som dålig om praktiskt taget hela filmen kunde avlägsnas, som godtagbar om en liten del av filmen och som god om en mycket mindre del av filmen samt som utmärkt om ingen film alls kunde avlägsnas. 7803474-1 16 HOSMMSA M umflaGo00HmvMfi>|ow .aoflmvdn Uwfi umuumumw _muhmsflæflwwamânomwflñmnumx flm mu>wflouH5mdßuwE|fifi0m:mQHMumEfiX0n@æn|Jv fifl | >m.H I mm.m «~.«~ ~m.«m m «o_m >m.H 1 mm.m «~.«~ >m.«m « | 7 | ¶ »m.H @m.m «~.«N >m.«m M «o.m | ßm.H @m.m «~.«~ ßm.«m N 1 >m.H >m.H mm.m «~.«~ >m.«m H Mflwhßwuüw , |HwHw«swfi «o.m >m.H @m.H mm.m «N.@~ >m_«m H .xm NH Hmmmfluw umamnxm N a AN MUHMS .mHDm UQE .MOP .GOQQH lmflQIHOflU .Hmflhüvdfi HNHHÜDME luflëmnnmx imfluflcflouow lomflwn |w.H|flmxm: xmmflmmuø lmmdmmub Mmwnmm H Hflwßmfi 7803474-1 17 mflww wmfiøm uvwfi vom ammflam» fiuanzäx m. mflfl. mfimnww wow nwmïaw» fiwnnflfix w umnnflfix m umnnflflx N mflww »måna mfiwø flünfiflx H Mmwumw åfimuwmsmfl uøm mwflmnmm vom Huunafiflx H Hwmäøwm mflHfluwmflUfi> mumh vwnmfiwmwßwwmflüwwud uwsfiuwnßflflfi Mwmußß fmnruOuv .H HHwnøB 7805474-1 18 Exemgel 2 14 delar av ett pigmentfärgämne med formeln ~ Ho-c-cH3 ll i -N=N-c-co-NHNH-co-c1¶3_ CO-NH 2 och B6 delar av en blandning av 69,5 delar utgångsmaterial l, 17,3 delar hydrcxipropylakrylat, 4,34 delar cirhydroximetylbensoinmetan- sulfonsyraester och 8,86 delar hexametoximetylmelamin revs i treva1s~ kalander på vanligt sätt till en blecktrycksfärg och bearbetades där- efter till ett blecktryck.Determination of adhesion: The coated sheet surface was scratched with a sharp knife into an X-shaped mark and then a piece of cellophane adhesive strip was pressed against this X-shaped engraved mark and then peeled off in order to determine if the coating film could be lifted from the metal layer carrier. . The adhesion was described as bad if practically the entire film could be removed, as acceptable for a small part of the film and as good for a much smaller part of the film and as excellent if no film could be removed at all. 7803474-1 16 HOSMMSA M um fl aGo00HmvM fi> | ow .ao fl mvdn Uw fi umuumumw _muhms fl æ fl wwamânomw fl ñmnumx fl m mu> w fl ouH5mdßuwE | fifi0 m: mQHMumE fi X0n @ J0n > m.H I mm.m «~.« ~ ~ m. «m m« o_m> m.H 1 mm.m «~.« ~> m. «m« | 7 | ¶ »m.H @ m.m« ~. «N> m.« M M «o.m | ßm.H @mm «~.« ~ ßm. «m N 1> mH> mH mm.m« ~. «~> m.« m H M fl whßwuüw, | HwHw «sw fi« om> mH @mH mm.m « N. @ ~> m_ «m H .xm NH Hmm al uw umamnxm N A than MUHMS .mHDm UQE .MOP .GOQQH ch al QIHO fl U .Hm al hüvd fi HNHHÜDME Iu al ëmnnmx im fl u al c al ouow lom al wn | wH | fl mxm: XMM al mmuø lmmdmmub Mmwnmm H H fl wßm fi 7803474-1 17 etc. ww wm Fi if uvw fi vom amm fl am »fi uanzäx m. m flfl. m fi mnww wow nwmïaw »f wnn flfi x w umnn flfi x m umnn flfl * N et al ww» degree m f WØ al Ün fifl x H Mmwumw the access muwmsm al UOM mw al mnmm vom Huuna fifl x H Hwmäøwm others H fl UWM fl U f> mumh vwnm fi wmwßwwm al üwwud uws fi uwnß flflfi Mwmußß fmnruOuv .H HHwnøB 7805474-1 18 Exemgel 2:14 a.m. parts of a pigment dye of formula ~ Ho- c-cH3 II in -N = Nc-co-NHNH-co-c1¶3-CO-NH 2 and B6 parts of a mixture of 69.5 parts of starting material 1, 17.3 parts of hydroxypropyl acrylate, 4.34 parts of cirhydroxymethylbenzoin methanesulfonic acid ester and 8.86 parts of hexamethoxymethylmelamine were ground in a three-calender in the usual manner to an inkjet ink and then processed to an inkjet.
Efter en bestrålningstid av 1,5 sekunder (HTQ-4-strålare från Philips, effekt, l KW, avstånd mellan UV-lampan och beläggnings- trycket: 4 cm) erhölls torkningsbeständiga blecktryck, som uppvisade mycket god vidhäftning till underlaget. Filmtjockleken av 2 /u.After an irradiation time of 1.5 seconds (HTQ-4 radiator from Philips, power, 1 KW, distance between the UV lamp and the coating pressure: 4 cm), drying-resistant ink pressures were obtained, which showed very good adhesion to the substrate. The film thickness of 2 / u.
Utgångsmaterial 3 122,5 g glycidylester av grenade monokarbonsyrcr med 9 - ll C-atomer (epoxiekvivalent 245), 36 g (0,5 mol) akrylsyra, 1,6 g trietylbensylammoniumklorid och 0,016 g toluhydrokinon sammanrördes under 10 timmar vid 90° C under överledning av kväve. Därefter uppgick syratalet till l.Starting material 3 122.5 g of glycidyl ester of branched monocarboxylic acids having 9 to 11 carbon atoms (epoxy equivalent 245), 36 g (0.5 mol) of acrylic acid, 1.6 g of triethylbenzylammonium chloride and 0.016 g of toluhydroquinone were stirred for 10 hours at 90 ° C under nitrogen transfer. Thereafter, the acid number was l.
Exemgel 3 - 5 Från de i nedanstående tabell 2 angivna komponenterna fram- ställdes blandningar och de således erhållna beläggningsmedlen anbrag- tes medelst en filmdragare med en tjocklek av 150 /u på avfettade stålplåtar. De således belagda stålplåtarna transporterades medelst en transportanordning på 6 cm avstånd från en UV-lampa (typ: Hanau Q 500) med sådan hastighet, att belysningstiden uppgick till cirka l sekund.Examples 3 - 5 Mixtures were prepared from the components listed in Table 2 below and the coating agents thus obtained were applied by means of a film puller with a thickness of 150 .mu.m to degreased steel sheets. The steel sheets thus coated were transported by means of a transport device at a distance of 6 cm from a UV lamp (type: Hanau Q 500) at such a speed that the illumination time amounted to about 1 second.
Detta förlopp upprepades tills beläggningarna var klibbfria, Antalet erforderliga förbipassager har angivits i tabell 2. 7803474-1 19 Jämförelseförsök 6 - 13 t Analogt med exemplen 3 - 5 framställdes filmer från be- läggningsmedlen från de i tabell 2 angivna komponenterna och man fast- ställde antalet erforderliga förbipassager för erhållande av klibb- frihet.This process was repeated until the coatings were tack-free. The number of required by-passes has been given in Table 2. 7803474-1 19 Comparative experiments 6 - 13 h In analogy to Examples 3 - 5, films were prepared from the coating agents from the components listed in Table 2 and determined. the number of bypasses required to obtain tack freedom.
Av tabell 2 framgår att kombinationerna enligt uppfin- ningen av minst en fotopolymeriserbar monomer, ett aminoplastharts och en fotoinitiatorkombination, hos vilken en fotoinitiator under inverkan av bestrålning bildar en syra, erfordrar det lägsta antalet förbipassager för erhållande av klibbfrihet. _ -..___ .....__....._..___. __ 7803474-1 20 Hm»mwmuhmcoufiflmøøumëlnwOwnmnawßmñfixonwmslá AH W : «>.N I @@.H~ H.~H >m_«m MH w «°.m «>_~ | mw.H~ H.~H >m_«m NH w | | «>.~ @w.H~ H.NH ßm.«m HH w wo.m 1 «>.~ mw.H~ ~.~H >m.«m OH OH | ßm_H | m@.H~ H_~H >m.«m m NH «°.m >m.H | @w.H~ H.~H >m.«m w wí | | ßm.H mw.»~ H.~H ~m.«m ß m «o.@ | >m.H mw.H~ H.NH >m.«m w xæmumw |.«smfi Q «o.m o.~ «>.= mw.H~ H.Nfl >m.«m m .xm m «0.m «>.° ø.~ mw_- H.~H ßm_«m w .xw m «o.@ >m_H >m.H @w.H~ H.~H >m_«m m .xw pmflflgm .H lnaflfix >w wøcmfl muumfl Hwmmdum mudm Hwßmflhmouß m A |HmnHm www nmmmm uflfiëm wmñ uoß. xomfl ßwflhnxmmfin amflnwumñ Hmflnwumä smwmfinnmw fløunm nnumx lwfiuwnflouow xnflomflwn nfloflucøxwm |mmcmmuD Immømmvb xßmuwm N HflwnmñTable 2 shows that the combinations according to the invention of at least one photopolymerizable monomer, an aminoplast resin and a photoinitiator combination, in which a photoinitiator forms an acid under the influence of radiation, require the lowest number of by-passes to obtain tack-free. _ -..___ .....__....._..___. __ 7803474-1 20 Hm »mwmuhmcou fifl møøumëlnwOwnmnawßmñ fi xonwmslá AH W:«> .N I @@. H ~ H. ~ H> m_ «m MH w« ° .m «> _ ~ | mw.H ~ H. ~ H> m_ «m NH w | | «>. ~ @ W.H ~ H.NH ßm.« M HH w wo.m 1 «>. ~ Mw.H ~ ~. ~ H> m.« M OH OH | ßm_H | m @ .H ~ H_ ~ H> m. «m m NH« ° .m> m.H | @ w.H ~ H. ~ H> m. «m w wí | | ßm.H mw. »~ H. ~ H ~ m.« m ß m «o. @ | > mH mw.H ~ H.NH> m. «mw xæmumw |.« sm fi Q «om o. ~«>. = mw.H ~ H.N fl> m. «mm .xm m« 0.m «> . ° ø. ~ Mw_- H. ~ H ßm_ «mw .xw m« o. @> M_H> mH @ wH ~ H. ~ H> m_ «mm .xw pm flfl gm .H lna flfi x> w wøcm fl muum fl Hwmmdum mudm Hwßm fl hmouß m A | HmnHm www nmmmm u flfi ëm wmñ uoß. xom fl ßw fl hnxmm fi n am fl nwumñ Hm fl nwumä smwm fi nnmw fl øunm nnumx lw fi uwn fl ouow xn fl om fl wn n fl o fl ucøxwm | mmcmmuD Immømmvb xßmuwm N H fl H
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2713797A DE2713797C3 (en) | 1977-03-29 | 1977-03-29 | Photopolymerizable coating agents |
Publications (3)
Publication Number | Publication Date |
---|---|
SE7803474L SE7803474L (en) | 1978-09-30 |
SE425402B SE425402B (en) | 1982-09-27 |
SE425402C true SE425402C (en) | 1984-07-16 |
Family
ID=6004974
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE7803474A SE425402C (en) | 1977-03-29 | 1978-03-28 | PHOTOPOLYMERIZABLE TRANSFER |
Country Status (9)
Country | Link |
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JP (1) | JPS53121831A (en) |
AT (1) | AT356781B (en) |
DE (1) | DE2713797C3 (en) |
ES (1) | ES468294A1 (en) |
FR (1) | FR2385778A1 (en) |
GB (1) | GB1587349A (en) |
IT (1) | IT7848618A0 (en) |
NL (1) | NL7803324A (en) |
SE (1) | SE425402C (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2120263B (en) * | 1982-05-17 | 1985-07-31 | Ciba Geigy Ag | A process for curing acid-curable abrasive compositions |
JPH03121154A (en) * | 1989-10-03 | 1991-05-23 | Asahi Chem Res Lab Ltd | Photosensitive thermoset resin composition and method for forming solder resist pattern therewith |
DE19709560C1 (en) * | 1997-03-07 | 1998-05-07 | Herberts Gmbh | Clearcoat paint composition for wet-in-wet application before stoving |
DE19748153A1 (en) * | 1997-10-31 | 1999-05-06 | Stockhausen Chem Fab Gmbh | Process for the production of cationic polyelectrolytes |
CN115677958A (en) * | 2022-11-03 | 2023-02-03 | 重庆市化工研究院有限公司 | Etherified amino resin esterified substance with ultraviolet curing characteristic and preparation method thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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DE1919678A1 (en) * | 1969-04-18 | 1970-11-05 | Bayer Ag | Alpha-methylol-benzoin-sulfonic acid ester |
DE2610437A1 (en) * | 1975-03-13 | 1976-09-16 | Continental Can Co | Photopolymerisable unsatd. ester mixture - with good adhesion to metal substrates contains acrylic polymer as adhesion promoter |
JPS592018B2 (en) * | 1975-03-26 | 1984-01-17 | 住友化学工業株式会社 | KARIYOSARETAKANKOSEIJIYUSHISOSAIBUTSUKARANARUGENKEI |
-
1977
- 1977-03-29 DE DE2713797A patent/DE2713797C3/en not_active Expired
-
1978
- 1978-03-27 JP JP3427178A patent/JPS53121831A/en active Pending
- 1978-03-28 ES ES468294A patent/ES468294A1/en not_active Expired
- 1978-03-28 IT IT7848618A patent/IT7848618A0/en unknown
- 1978-03-28 AT AT216778A patent/AT356781B/en active
- 1978-03-28 SE SE7803474A patent/SE425402C/en unknown
- 1978-03-29 FR FR7809106A patent/FR2385778A1/en active Granted
- 1978-03-29 NL NL7803324A patent/NL7803324A/en not_active Application Discontinuation
- 1978-03-29 GB GB12224/78A patent/GB1587349A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
SE425402B (en) | 1982-09-27 |
ATA216778A (en) | 1979-10-15 |
JPS53121831A (en) | 1978-10-24 |
AT356781B (en) | 1980-05-27 |
SE7803474L (en) | 1978-09-30 |
NL7803324A (en) | 1978-10-03 |
DE2713797C3 (en) | 1982-04-01 |
ES468294A1 (en) | 1978-11-16 |
DE2713797B2 (en) | 1981-06-25 |
DE2713797A1 (en) | 1978-10-19 |
GB1587349A (en) | 1981-04-01 |
FR2385778A1 (en) | 1978-10-27 |
IT7848618A0 (en) | 1978-03-28 |
FR2385778B1 (en) | 1983-09-23 |
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