DK157083B - Anvendelse af aromatisk-aliphatiske ketoner som initiatorer til fotopolymerisation af umaettede forbindelser samt til fotokemisk tvaerbinding af polyolefiner, fotopolymeriserbart system indeholdende saadanne ketoner samt fremgangsmaade til fotopolymerisation af umaettede forbindelser - Google Patents
Anvendelse af aromatisk-aliphatiske ketoner som initiatorer til fotopolymerisation af umaettede forbindelser samt til fotokemisk tvaerbinding af polyolefiner, fotopolymeriserbart system indeholdende saadanne ketoner samt fremgangsmaade til fotopolymerisation af umaettede forbindelser Download PDFInfo
- Publication number
- DK157083B DK157083B DK576278AA DK576278A DK157083B DK 157083 B DK157083 B DK 157083B DK 576278A A DK576278A A DK 576278AA DK 576278 A DK576278 A DK 576278A DK 157083 B DK157083 B DK 157083B
- Authority
- DK
- Denmark
- Prior art keywords
- atoms
- alkyl
- compounds
- phenylene
- phenyl
- Prior art date
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- -1 (phenyl) - Chemical class 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 229910003849 O-Si Inorganic materials 0.000 claims description 2
- 229910003872 O—Si Inorganic materials 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920006305 unsaturated polyester Polymers 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-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
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical compound C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- PWLDUQHHMYAKKG-UHFFFAOYSA-N 2-cyclopentyl-2-hydroxy-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(O)(C)C1CCCC1 PWLDUQHHMYAKKG-UHFFFAOYSA-N 0.000 description 1
- DIVXVZXROTWKIH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(O)(C)C(=O)C1=CC=CC=C1 DIVXVZXROTWKIH-UHFFFAOYSA-N 0.000 description 1
- RTIWNILJURRTDS-UHFFFAOYSA-N 2-hydroxy-2-methyl-1,3-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(O)(C)CC1=CC=CC=C1 RTIWNILJURRTDS-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
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- KZHJQBWFGOENGB-UHFFFAOYSA-N 2-methyl-2-(2-methylpiperidin-1-yl)-1-phenylpropan-1-one Chemical compound CC1CCCCN1C(C)(C)C(=O)C1=CC=CC=C1 KZHJQBWFGOENGB-UHFFFAOYSA-N 0.000 description 1
- TUTRUYLBPZSZNM-UHFFFAOYSA-N 2-methyl-2-[4-(2-methyl-1-oxo-1-phenylpropan-2-yl)piperazin-1-yl]-1-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C)(C)N(CC1)CCN1C(C)(C)C(=O)C1=CC=CC=C1 TUTRUYLBPZSZNM-UHFFFAOYSA-N 0.000 description 1
- NWRBWVKDJKJWPD-UHFFFAOYSA-N 2-methyl-2-piperidin-1-yl-1-thiophen-2-ylpropan-1-one Chemical compound C=1C=CSC=1C(=O)C(C)(C)N1CCCCC1 NWRBWVKDJKJWPD-UHFFFAOYSA-N 0.000 description 1
- PXOGBEAGHDNDDM-UHFFFAOYSA-N 2-morpholin-4-yl-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CN1CCOCC1 PXOGBEAGHDNDDM-UHFFFAOYSA-N 0.000 description 1
- CARNFEUGBMWTON-UHFFFAOYSA-N 3-(2-prop-2-enoxyethoxy)prop-1-ene Chemical compound C=CCOCCOCC=C CARNFEUGBMWTON-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004484 Briquette Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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- 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
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Description
DK 157083 B
Den foreliggende opfindelse angâr anvendelsen af aromatisk-aliphatiske ketoner, der er substituerede i a-stilling> som initiatorer til fotopolymerisation af umættede forbindel-ser samt til fotokemisk tværbinding af polyolefiner samt systemer, der kan fotopolymeriseres eller tværbindes og in-deholder sâdarme initiatorer, og en fremgangsmâde til foto-polymerisation af umættede forbindelser.
Potokemiske polymerisationsprocesser har fâet væsentlig be-tydning i teknikken, fremfor ait i sâdanne tilfælde, hvor . tynde lag skal hærdes pâ kort tid,sâsom ved hærdning af lak-overtræk eller ved torring af trykfarver. W-bestrâling un-der tilstedeværelse af fotoinitiatorer viser i sammenligning med traditionelle hærdningsfremgangsmâder en række fordele, hvoraf den vigtigste nok er den hé je hastighed ved fotohærd-ningen. Hastigheden er stærkt afhængig af den anvendte fotoinitiator, og der bar ikke manglet forsog pâ at erstatte de almindelige initiatorer med stadig bedre og mere virksom-me forbindelser. Til de mest virksomme fotoinitiatorer horer derivater af benzoin, fremfor ait benzoinethere, som eksem-pelvis beskrifes i DT-PS nr. 1.694.149, derivater af a-bydroxymetbylbenzoin, som er beskrevet i DT-OS nr. 1.923*266, samt dialkoxyacetophenoner og benzil-monoketaler, som eksem-pelvis er beskrevet i DT-OS nr. 2.261.383 eller nr. 2.232.365. a-Aminoacetophenoner og a-diaminoacetophenoner er for nylig foreslâet i USA-patentskrift nr. 4.048.034 og a-hydroxy-a-alkylolacetophenoner og deres ethere i DT-OS nr. 2.357*866 som fotoinitiatorer.
Ulemper, der er forbundet med disse kendte fotoinitiatorer, er til dels utilstrækkelig lagerstabilitet i morke af de med sâdanne initiatorer blandede fotopolymeriserbare systemer.
ÎTogle benzoinderivater har tilbo jelighed til at fremkalde gulning af de hærdede masser. André initiatorer har util-strækkelig reaktivitet, hvilket ytrer sig ved relativt lange hærdningstider, eller de er for lidt oploselige i de fotopolymeriserbare systemer, eller de inakbiveres hnrtigt af luftens oxygen.
2
DK 15708 3 B
I teknikken er der derfor bebov for fotoinitiatorer, som er letoploselige i substratet, og som ved god lagerstabilitet i m0rke burtigere udleser fotopolynerisation og giver et bojere polymerudbytte pr. tidsenhed end de kendte fotoinitiatorer. Ved anvendelse af sâdanne forbedrede fotoinitiatorer vil de kostbare industrielle W-bestrâlingsanlæg kunne udnyttes bedre.
Det bar vist sig, at forbindelser med de nedenstâende form-ler I, II, III og IV har de krævede egenskaber som fotoinitiatorer, fremfor ait bevirker de en burtig polymérisation, og de bar ikke eller kun i væsentligt ringere grad end de kendte fotoinitiatorer de skildrede ulemper. De egner sig desuden til fotokemisk tværbinding af polyolefiner.
Opfindelsen angâr anvendelsen af aromatisk-aliphatiske ke-. to-ner med formlen O R1 r H i -
Ar--G - C - Σ i (I) - lo J n ΙΓ
Ο Σ Σ O
« I , ! Il
Ar-G-C-R^-C-C-Ar (II) l2 l2 ΈΓ Έτ O R1 R1 o
II I I II
Ar-C-G-Σ' - C - C - Ar (III)
1 p I
R2 e2 eller
O
R1
AV
I Γ\χ an 3
DK 157083 B
hvori n er 1 eller 2,
Ar, nâr n er 1, betyder aryl med 6 til 14 C-atomer, med Cl,
Br, CN, OH, alk, -Oalk, -Salk, -S02alk, -S02phenyl, -COOalk, -SO2NH2/ -SQ2NHalk eller -S02N(alk)2 substitueret phenyl eller thienyl, pyridyl eller furyl, hvori alk betyder en alkylgruppe med 1 til 4 C-atomer, og nâr n er 2, arylen med 6-12 C-atomer eller en gruppe phenylen-T-phenylen-, hvori T betyder -O-, -S-, -S02~, -CH2- eller -CH=CH-, X er en af grupperne -NR^R^, -OR^ eller -O-Si(R^)(R®)9, 10 _ λ X* er en af grupperne -NR -, -N(phenyl)-, -N^ SN- eller -N<R10)-R11-N(R10)-, "-' Y er en direkte binding eller -CH2-, Z er -O-, -S-, “S02-, -CH2" eller -C(CH3)2-, R"*" betyder alkyl med 1-8 C-atomer, der kan være substitueret med OH, C-^^-alkoxy, C2-Cg-acyloxy, -COO-(C^-C^)-alkyl eller -CN, cycloalkyl med 5-6 C-atomer eller phenylalkyl med 7 til 9 C-atomer,
2 1 12 R har en af de for R angivne betydninger, eller R og R
betyder sammen alkylen med 4 til 6 C-atomer eller oxa- eller azaalkylen med 3 til 4 C-atomer, 3 R betyder en.direkte binding, alkylen med 1 til 6 C-atomer, oxaalkylen med 2 til 6 C-atomer, phenylen, diphenylen, en gruppe 2 -phenylen-T-phenylen-, eller de to substituenter R sammen med 3 R og de to C-atomer, hvortil disse substituenter er bundet, danner en cyclopentan- eller cyclohexanring, 4 R betyder alkyl med 1 til 12 C-atomer, med -OH eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl, phenylalkyl med 7 til 9 C-atomer, phenyl eller med Cl, alk, OH, -Oalk eller -COOalk substitueret phenyl, 5 R betyder alkyl med 1 til 12 C-atomer, med -OH eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl 4
eller phenylalkyl med 7 til 9 C-atomer, eller sammen med R
betyder alkylen med 4 til 5 C-atomer, der kan være afbrudt af -O-, -NH- eller -Nalk-, eller i tilfælde af forbindelser med 2 formlen I sammen med R alkylen eller phenylalkylen med 1 til 9 C-atomer eller oxa- eller azaalkylen med 2 til 3 C-atomer,
R^ betyder hydrogen, alkyl med 1 til 12 C-atomer, med -OH
DK 157083 B
4 eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl, benzyl, phenyl eller med Cl eller alk substitue- 2 ret phenyl, eller sammen med R danner alkylen med 3 til 4 C-atomer, 7 8 R og R er ens eller forskellige og betyder alkyl med 1 til 4 C-atomer eller phenyl, R10 alkyl med 1 til 8 C-atomer, cyclohexyl eller benzyl, og R^ er alkylen med 2 til 8 C-atomer, xylylen, phenylen eller en gruppe -phenylen-T-phenylen-, med undtagelse af de forbin- delser med formlen I, hvori n er 1, Ar er phenyl eller med
Cl, Br, alkyl, alkoxy eller dialkylamino substitueret pheiiyl, 1 2 X er hydroxy eller alkoxy, og R og R er usubstitueret alkyl, som initiatorer til fotopolymerisation af umættede forbindel-ser samt til fotokemisk tværbinding af polyolefiner.
Det drejer sig ved disse forbindelser altsâ om aromatisk-aliphatiske ketoner, hvis α-C-atom er tertiært og substitueret med en hydroxyl- eller aminogruppe eller deres for-etherings- eller silyleringsprodukt. Derved kan den alipha-tiske gruppe ogsâ være cycloaliphatisk eller araliphatisk, eller være forbundet med den aromatiske gruppe under ring-slutning, hvilket svarer til de benzocycliske ketoner med formlen IV.
Af de ovenfor angivne substituenter kan R1, R^ og R10 være alkyl med 1 til 8 C-atomer, f.eks. metbyl, ethyl, h tr g propyl, butyl, hexyl eller octyl. R , Έ/ og R som alkyl kan være uforgrenet eller forgrenet alkyl med 1 til 12 C-atomer, sâsom metbyl, ethyl, isopropyl, tert.butyl, iso-amyl, n-hexyl, 2-ethylh.exyl, n-decyl eller n-dodecyl. Alk betyder en lavalkylgruppe med 1 til 4 C-atomer, sâsom metbyl, ethyl, isopropyl, n-butyl eller tert.butyl.
5
DK 157083 B
12 6 R, R og R° i betydning af hydroxyalkyl, alkoxyalkyl eller acyloxyalkyl kan f.eks. være hydroxymethyl, 1-hydroxyetîiyl, 2-hydroxyethyl, 2-isopropoxyeth.yl, 1-hydroxyisobutyl, l-acetyloxybutyl, 1-acryloyloxyîiexyl, 1-hydroxyoctyl, 3- benzoyloxypropyl, methoxymethyl eller isobutoxymethyl.
Acylgruppen kan derved være en rest af en alipbatisk eller
aromatisk carboxylsyre. Rortrinsvis drejer det sig om ΙΑ S
hydro^çyalkylgrupper og deres ethere eller estere. R og Έ/ som hydroxyallyl eller alkoxyalkyl kan f.eks. være 2-hydroxyethyl, 2-butoxyeth.yl, 2-methoxypr opyl, 3-hydroxy-propyl eller 2-etboxybutyl. Rortrinsvis drejer det sig derved om 2-h.ydroxyalkylgrnpper og deres ethere.
1 2
Med CN substitueret alkyl kan i tilfældet af R eller R , f.eks. være 2-cyanoethyl, 2-cyanopropyl eller 4-cyanobutyl, 12 4 i tilfælde af R , R og R ogsâ cyanomethyl, 2-cyanhexyl eller 4-cyanoctyl. Foretrukket er en 2-cyanethylgruppe.
1 2
Med -COQalk substitueret alkyl kan i tilfælde af R og R f.eks. være -CH2COOC2H5, -CH2CH2COOCH3, -(CH2)3-COOCH3 eller -ch2ch(c2h5)-cooc4h9.
1 2 R og R i betydning af cycloalkyl kan være cyclopentyl el- 12 4 5 1er cyclohexyl. R , R , R og R i betydning af phenylalkyl kan f.eks. være benzyl, phenylethyl eller dimethylbenzyl.
Ar sont ary.l eller substitueret phenyl kan f.eks. være phenyl, naphthyl, phenanthryl, anthracyl, diphenylyl, chlorphenyl, bromphenyl, dichlorphenyl, mesityl, isopropylphenyl, cyan-phenyl, hydroxyphenyl, tolyl, tert.butylphenyl, xylyl, iso-propyl-chlorphenyl, methoxyphenyl, ethoxyphenyl, chlortolyl, bromxylyl, methylthiophenyl, butylsulfophenyl, phenylsulfo-phenyl, ethoxycarbonylphenyl, tert-butoxycarbonylphenyl, methylaminosulfophenyl eller dipropylaminosulfophenyl.
1 2 R og R sammen kan betyde alkylen eller oxa- eller aza- 1 2 alkylen. I dette tilfælde danner R og R sammen med carbon-atomet, hvortil de er bundet, en cyclopropan-, cyclobutan-, nvr·.! r>r>i»rvt-3n— _ nvpl nhpYan- . pvp! nhpnf an- . +-<=.-(-'r^hTrr1r,iTFnT'^n— _ 6
DK 157083 B
tetrahydropyran-, pyrrolidin- eller piperidinring.
2 5 R og R kan sammen betyde alkylen eller phenylalkylen med 1 til 9 carbonatomer eller oxa- eller azaalkylen. I dette 2 5 2
tilfælde danner R oq· R sammen med carbonatomet, hvortil R
5 er bundet, og N-atomet, hvortil R er bundet, en 3- til 6-leddet ring, sâsom en aziridin-, azetidin-, pyrrolidin-, imidazolidin-, piperidin, piperazin- eller morpholinring.
4 5 R og. R kan sammen betyde alkylen med 4 til 5 C-atomer, der kan være afbrudt af -O-, -NH- eller -Nalk-. I dette tilfælde 4 5 danner R og R . sammen med N-atomet, hvortil de er bundet, en pyrrolidin-, piperidin-, morpholin- eller 4-alkylpiperazinring.
3 11 R kan være alkylen med 1 til 6 C-atomer, R alkylen med 2 til 8 C-atomer. Eksempler herpâ er, indenfor det angivne antal C-atomer, methylen, 1,2-ethylen, 1,3-propylen, 1,4-butylen, 2,2-dimethyl-l,3-propylen, 1,6-hexylen, 2-methyl-3~ethyl-l,4- 3 butylen eller 1,8-octylen. R kan ogsâ være oxaalkylen med 2 til 6 C-atomer, sâsom 2-oxa-l,3-propylen, 3-oxa-2,4-pentylen eller 3-oxa-l,5-pentylen.
Ar kan betyde arylen med 6 til 12 C-atomer, sâsom phenylen, naphthylen eller diphenylen.
Forbindelserne med formlen 17 er, sâfremt Y er en direkte binding, derivater af indanon, cumaranon eller thioeumara-non. ITâr Y er CB^, drejer det sig om derivater af tetralon, chromanon eller thiochromanon.
Opfindelsen angâr især anvendelsen af forbindelser med formlen I eller II, hvori X er en gruppe -ER^R^. Disse forbindelser er ved α-C-atomet forgrenede og med aminogrupper substituerede aryl-allyl-ketoner.
Opfindelsen angâr endvidere især anvendelsen af forbindelser med formlen I eller II, hvori X betyder en gruppe -QR^.
Disse forbindelser er i α-stilling forgrenede og med hydroxyl- eller ethergrupper substituerede aryl-alkyl-keton-
7 DK 157083 B
Opfindelsen angâr endvidere især anvendelsen af f orMndel-ser med formlen I eller II, hvori X betyder an grappe -OSiR^CR^^· Disse forDindelser er i a-stilling forgrenede og med silyloxygrupper saistituerede aryl-alkyl-ketoner.
7 8
Eksempler pâ gruppen -OSiR'(R'©r f.eks. grupperne tri-methylsiloxy, dimethylplienylsiloxy, me t hy 1 dipheny1s i1oxy eller triplienylsiloxy.
Eksempler pâ ifolge opfindelsen anvendelige forbindelser med formlen I, livori n er 1, er folgende: 2-Bydroxy-2-metliyl-propiopîienon 2-Hydroxy-2-eth.yl-propiopli.enon 2-Hydroxy-2-’butyl-propioph.enon 2-Metlioxy-2-metliyl-propioplienon 2-Hydroxy-2-methyl-(p-acetylaminopropioplienon) 2-Hy dr oxy- 2-me tny 1- ( p-me thy 1 thi o-propi ophenon) 2-Hydroxy-2-metliyl-(p-car'betlioxy-propioplienon) 2-Ph.eno xy- 2-me t hy 1 -propi ophenon 2-Allyloxy-2-meth.yl-propioplienon 2-Benzyl oxy- 2-me thy 1-pr opi ophenon 2- ( 2-Meth.oxycarbonyl etb.oxy) -2-metliyl-propioplienon 2- ( 2-Cyane tlioxy ) -2-me tlhyl-pr opiophenon 2-Metlioxyethoxy-2-methyl-propiop]ienon 2-Hydr oxyme th.oxy-2-me thy 1-pr opi oplienon 2-HydroxyetllOxy-2-metL·yl-propiopllenon a-Hydroxy-a, a-bis- ( cyanetHyl ) -acetopHenon Y-Hydroxy-Y-benzoylpimelinsyre-diethylester 2-Di- ( 2-hydr oxye thyl ) -amino-2-me thyl- 3-phenyl-propiopiienon 2-Dimeth.ylamino-2-metliyl-propiop]ienon 2-ΰίβΐ^ΐ3Πΐίηο-2-ιαβΉ^·1-ρΓορΐορΙΐ6ηοη 2-Di~butylamino-2-metliyl-propioplienon 2-Di-llydroxyetL·ylamino-2-metllyl-propiopllenon 2-Piperidino-2-meth.yl-propiop]ienon
s DK 157083B
2- ( 2-Me thy lp iperi dino )-2-methyl-propioph.enon 2-Morpb.olino-2-methyl-propiopbenon 2-Piperazino-2-metliyl-propiopbenon 2- (4-Methylpiperazino ) -2-methyl-propi opbenon 2-Pyrrolidino-2-meth.yl-propioph.enon 2- Methylphenylamino-2-methyl-propiophenon 1-Benzoyl-cyclohexanol 1-Benzoyl-cyclopentanol 1- Benzoyl-cyelopropanol 3- p-Me thoxybenz oyl- 3-dîme thy 1 aminohep t an 6- ( 2-Bydroxyisobutyryl )-tetralin 5- ( 2-Hydr oxyisobutyry 1 ) -indan 6- ( 2-Dimetl]ylam.ino-is obutyryl ) -tetralin 6- (2-Morpholino-isobutyryl)-tetralin 6- ( 2-Piperidino-isobutyryl) -tetralin 6-(2-Piperazino-isobutyryl)-tetralin 2- ( 2-Me thoxybenzoyl ) -2-diallylaminopropan 2- ( 2-Thenoyl ) -2-piperidinopropan 2- ( 2 -U aphthoy 1 ) -2-ae e t oxybut an 2-p-Phenylbenzoyl-2-di-(2-hydroxyet]^l)-aminopropan 1- Methyl-2-o-cblorbenzoyl-piperidin 2- o-Toluyl-2-(trimethylsiloxy)-propan 2-ïïydroxymethoxy-2-methyl-propiophenon 2-Hydroxyme tboxy-2-metliyl- ( 2,5-dimethylpropiophenon) 2-Hydroxym.ethoxy-2-metliyl-(p-isopropylpropiophenon) 2-Hydroxy-2-benzyl-propiophenon 2-Bydroxy-2-(p-metbylbenzyl )-propiopbenon 2-Hydroxy-2-cyc 1 ohexy 1-propi ophenon 2-Hydroxy-2-cyclûpentyl-propiophenon 2- ( 2-Eydr oxyethoxy) -2-methyl-propi ophenon 2-ïïydroxy-2-allyl-propiopbenon
Eksempler pâ forbindelser med formlen I, hvori n er 2, er: 4,4-' -Bis- (α-hydroxy-is obutyryl ) -diphenyloxid 4,4’ -Bis-(a-bydroxy-isobutyryl)-dipnenyl 4,4' -Bis-(a-hydroxy-isobutyryl)-diphenylsulf id 4,4’ -Bis-(a-hydroxy-isobutyryl)-diphenylmethan 4,4' -Bis- (a-piperidino-is obutyryl) -diplienyloxid
9 DK 157083 B
4-,4-1 -Bis-[ oc- (isopropylamino ) -isobutyryl] -diphenyl 4-, 4- ' -Bis- ( α-b enz oyl oxy-i s obutyryl ) - diphenyl oxi d
Eksempler pâ forbindelser med formlen II er: 1.4— Diphenyl-2,3-dimethyl-2,3-dihydroxy-bu.tandion- 1,4 2.4— Dibenzoyl-2,4— dihydroxy-pentan 2,9-Dibenzoyl-2,9-dimethyl-3,8-dioxadecan 2,7-dibenzoyl-2,7-dimethyl-3,6-dioxaoctan 1,6-Diphenyl-2,5-dimethyl-2,5-dihydroxy-hexandion- 1,6 1.4— Diphenyl-2,3-dimetliyl-2,3-bis- ( dime thylamino ) -but an-dion-1 , 4- 1.4— Diphenyl-2,3-dim.etb.yl-2,3-dipiperidyl-but andion-1,4- 1.2- Bis-hydroxy-l, 2-bis-benzoyl-cyclohexan 1.2- Bis-dimethylamino-l, 2-bis-benzoyl-cyclonexan 1.2- Bi s -mo rpbo 1 ino -1,2-bis-benzoyl-cyclohexan
Eksempler pâ forbindelser med formlen III er: 1.4— Bis-(l-benzoyl-isopropyl)-piperazin N,K-Bi s-(α-benzoy1-isopropyl)-butylamin H ,N'-Dimethyl-Ν,ΙΓ -bis-(a-benzoyl-isopropyl)-ethylendiamin.
Eksempler pâ forbindelser med formlen IY er: l-0xo-2-dimethylamino~2-methyl-l ,2,3,4~tetrahydronaphthalen l-0xo-2-hydroxy-2-methyl-l ,2,3,4-tetrahydronaphthalen l-0xo-2-hydroxy-2-methylindan.
Eorbindelserne med formlerne I, II, III og IY er til dels kendte forbindelser, til dels drejer det sig om nye forbindelser.
DK 157083B
10
Disse nye forhindelser kan fremstilles analogt med de kendte forhindelser, hvortil forskellige metoder kommer pâ taie.
Sâledes kan forhindelser med formlen I fremstilles ud fra aromatisk-alipîiatiske ketoner ved felgende reaktionstrin: i o tj 2 -i p CEUONa
Ar--CO-GHRTr __> Ar--CO-CBrE E^ —> J η I— _ln ~ Ό E1 ~f Γ 0 E1
Ar--0-C -Ar--C—C—X
I \ 2 >2 L0CH3 R Jn ]_ E Jn
Som HX kan derved anvendes aminer [C. L. Stevens, Ch. Hung Chang, J. Org. Chem. 27 (1962), 4392] eller vand [C. L.
Stevens, E. Earkas, J. Am. Chem. Soc. 74 (1952), 618,og C. L. Stevens, S. J. IDykstra, J. Am. Chem. Soc. 75 (1953)5 5976].
I mange tilfælde lykkes ogsâ den direkte omsætning af a-hromketoner til forhindelser med formlen Γθ l1 1 ? TTY 11 1
Ar— CO— CBrE j± - > Ar--C — C — X (I) ‘2 — n 1_ — n eksempelvis med aminer, alkalimetalliydroxider eller alkali-phenoxider. I stedet for bromforhindelser kan ogsâ anvendes de tilsvarende chlorforhindelser.
De sâledes opnâede hydroxyketoner med formlen I (X=0H) kan foretheres eller O-silyleres ved de sædvanlige metoder.
Anvender man ved de ovenfor angivne reaktioner i stedet for den monofunktionelle forhindelse HX en difunktionel forhin-delse H-X’-H, opnâc man forhindelser med formlen III.
11 DK 157083 B
Rorbindelser meà formlen II kan fremstilles analogt med dem med formlen I, idet man som udgangsmateriale an vende r di-ketoner med den almene formel R2 R2
I 7 I
Ar - CO - CH - Έ? - CH - CO - Ar
Ligeledes pâ analog mâde opnâr man forbindelserne med formlen IY ud fra cycliske ketoner med formlen 0 1 crÿ som udgangsmateriale.
Eorbindelser med formlen I, hvori R^ er en substitueret alkylgruppe, kan opnâs ud fra forbindelser med formlen
Ar-0 GO-GÏÏ(R2) -X] ^ ved reaktion med aldehyder (R^ = hydroxy- alkyl) eller med en additionsdygtig vinylforbindelse, f.eks.
1 2 med acrylsyreestere eller acrylonitril. Uâr sâvel R som R er substitueret alkyl, kan begge substituenter indfores sam-men ved reaktion mellem en forbindelse Ar-Ë-C0-CH2-Xln og mindst 2 mol af et aldehyd eller en viny 1 fortinde 1 se. Ud fra bydroxyalkylgrupperne R og/eller R kan der ved forethe-ring eller forestering opnâs de tilsvarende alkoxyalkyl-og acyloxyalkylgrupper. Analogt kan ogsâ fremstilles forbindelser med formlen II, III eller IY med substituerede 1 2 alkylgrupper som R eller R .
Kedens aile disse omtalte syntesemetoder gâr ud fra en aro-matisk-aliphatisk keton, hvori en substituent X indfores pâ forskellige mâder, er det i bestemte tilfælde ogsâ mu-ligt at indfore substituenten X allerede under keton-synte-sen ifolge Rriedel-Crafts efter reaktionsligningen: R1 R1
I A1C1, I
X - C - C0C1 + Arïï -*·> Ar - GO - C - X
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12
Dette fomdsætter, at substituenten Σ ikke angribes imder reaktionsbetingelserne ved Priedel-Crafts-reaktion. Pâ den-ne mâde kan der f.eks. ved anvendelse af heterocycliske carboxylsyrecblorider fremstilles forbindelser med formlen I, hvori X og R1 sammen med G-atomet, hvortil de er bundet, danner en beteroring.
Det fotopolymeriserbare System if0lge opfindelsen er ejen-dommeligt ved, at det bestâr af mindst én umættet fotopoly-meriserbar forbindelse og 0,1 til 20 vægtprocent, fortrins-vis 0,5 til 5 vægtprocent, af en af forbindelserne med den ovenfor anf0rte formel I, II, III eller IV som fotoinitiator samt eventuelt yderligere kendte og almindelige tilsætnings-stoffer.
Fremgangsmâden if0lge opfindelsen til fotopolymerisation af umættede forbindelser er ejendommelig ved, at man som fotoinitiator anvender en forbindelse med den ovenfor anf0rte formel I, “II, III eller IV.
Sâdanne forbindelser er eksempelvis nmættede monomère, sâsom estere af acryl- eller methacrylsyre, f.eks. metbyl-, etbyl-, n- eller tert.butyl-, isooctyl- eller bydroxyetbyl-acrylat, metbyl- eller ethylmetbacrylat, ethylendiaerylat, neopentyl-diacrylat, trimetbylolpropantrisacrylat, penta-erytbrito 1-tetraacrylat eller pentaerytbritoltrisacrylat, acrylonitril, methacrylonitril, acrylamid, metbacrylamid, ÏT-substituerede (metb)acrylamider, vinylestere, sâsom vinyl-acetat, -propionat, -acrylat eller -snccinat, andre vinyl-forbindelser, sâsom vinyletbere, styren, -altylstyrener, ' balogenstyrener, divinylbenzen, vinylnaphthalen, R-vinyl-pyrrolidon, vinylcblorid eller vinylidenchlorid, allylfor-bindelser, sâsom diallylplitbalat, diallylmaleat, triallyl-isocyanurat, triallylpbospbat eller etbylenglycol-diallyl-ether,og blandinger af sâdanne nmættede monomère.
Potopolymeriserbare forbindelser er desnden nmættede oligo- mere eller polymère og deres blandinger med nmættede mono-
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mere. ïïertil 3i0rer termoplastiske barpikser, der indeholder umættede grupper, sâsom fumarsyreestere, allylgrupper eller acrylat- aller methacrylatgrupper. For det meste er disse umættede grupper bundet via funktionelle grupper til hoved-kæden i disse lineære polymère. Stor betydning bar blan-dinger af oligomere med mono- og polyumættede monomère.
Eksempler pâ sâdanne oligomere er umættede polyestere, umættede acrylharpikser og isocyanat- eller epoxid-modifi-cerede acrylatoligomere samt polyetheracrylatoligomere.
Eksempler pâ polyumættede forbindelser er fremfor ait acrylater af dioler og polyoler, f.eks. hexamethylen-di-acrylat eller pentaerythritol-tetracrylat. Ogsâ som mono-umættede monomère foretræfckes acrylater, sâsom. butylacrylat, plienylacrylat, benzylacrylat, 2-eth.yl-h.exylacrylat eller 2-h.ydroxypropylacrylat. Man kan ved valg blandt de forskel-lige repræs entant er for de tre komponenter variere konsi-stensen af den upolymeriserede blanding samt plasticiteten af den polymeriserede barpiks.
Ved siden af disse tre komponentblandinger spiller ved polyesterharpikser fremfor ait to komponentblandinger en stor rolle. Disse bestâr for det meste af en umættet polyester og en vinylforbindelse. De umættede polyestere er oligomere foresteringsprodukter af mindst én umættet di-carboxylsyre, sâsom malein-, fumar- eller citraconsyre, og for det meste mindst én mættet dicarboxylsyre, sâsom pbthal-syre, ravsyre, sebacinsyre eller isoph-tbalsyre, med glycoler, sâsom etbylenglycol, propandiol-1,2, di- eller triethylen-glycol eller tetrametbylenglycol, idet der til modificering for det meste ogsâ medanvendes monocarboxylsyrer og mono-alkoiioler. Disse umættede polyestere oploses sædvanligvis i en vinyl- eller allylforbindelse, fortrinsvis anvendes hertil styren.
Fotopolymeriserbare systemer, som anvendes til de forskel-lige formâl, indebolder for det meste udover de fotopolymeriserbare forbindelser og fotoinitiatoren en række andre tilsætninger.Sâledes er· det i mange tilfælde almindeligt at tilsætte termiske inbibitorer,der fremfor ait skal beskytte mod
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for tidlig polymérisation ved fremstilling af systemerne ved blanding af komponenterne. ïïertil anvendes eksempelvis hydroquinon, bydro çjuinonderivater, p-metboxypbenyl, β-napbthylamin eller β-napbtholer. Endvidere kan der tilsæt-tes mindre mængder W-absorbere, f.eks. sâdanne af benz-triazol- eller benzopbenontypen.
. . Œil forhojelse af lagerstabiliteten i morke kan tilsættes kobberforbindelser, sâsom kobbernapb.tb.enat, -stearat eller -octoat, phosphorforbindelser, sâsom tripbenylpbospbin, tributylpbospbin, trietbylphoSphit, tripbenylpbospbit eller tribenzylpbosphat, kvaternære ammonium!orbinde 1ser, sâsom tetramethylammoniumcblorid eller trimetbyl-benzylammonium-chlorid, eller bydroxylaminderivater, sâsom U-diethyl-hydroxylamin. Endvidere kan de fotopolymeriserbare systemer indeholde kædeoverforingsmidler, sâsom ΪΓ-methy 1 dietbano 1-amin, trietbanolamin eller cyclohexen.
For at udelukke den inbiberende virkning af luftens oxygen sætter man hyppigt paraffin eller lignende voksagtige stof-fer til fotobærdelige systemer. Disse stoffer svommer oven-pâ ved polymerisationens begyndelse pâ grund af manglende oploseligbed i den polymère og damier et transparent over-fladelag, der forhindrer luftens adgang. Ogsâ ved indforing af autooxiderbare grupper, eksempelvis allylgrupper, i barpiksen, der skal bærdes, kan luftens oxygen desaktiveres.
Fotoinitiatorerne kan ogsâ anvendes i kombination med radikalinitiatorer, sâsom peroxider, bydroperoxider, keton-peroxider eller percarboxylsyreestere.
Fotopolymeriserbare systemer indeholder endvidere ait ef-ter anvendelsesformâlet fyldstoffer, sâsom kiselsyre, tal-kum eller gips, pigmenter, farvestoffer, fibre, tbixotropi-midler eller flydehjælpemidler.
Eadvidere kan der ogsâ anvendes kombinationer med kendte fotoinitiatorer, sâsom benzoinetbere, dialkoxyacetopbenoner eller benzilketaler.
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15
Især til f otopolymerisationen af tyn.de lag og trykfarver kan anvendes kombinationer af de omhandlede fotoinitiatorer med aminer og/eller aromatiske ketoner. Eksempler pâ aminer er triethylamin, N-methyldiethanolamin, N-dimethylethanol-amin eller p-dimethylaminobenzoesyreester. Eksempler pâ ketoner er benzophenon, substituerede benzophenonderivater,
Miobier's keton, antraquinon og antbraquinonderivater samt thioxantbon og dets derivater.
Stor betydning har fotohærdningen ved trykfarver, da binde-midlets torringstid er en afgorende faktor for produktions-bastigheden for grafiske produkter og skal vasre af storrel-sesordenen brokdele af sekonder. De omhandlede initiatorer er ogsâ velegnede til fotohærdelige systemer til fremstil-ling af trykplader. Herved anvendes f.eks. blandinger af oploselige lineære polyamider med fotopolymeriserbare monomère, eksempelvis acrylamider, og en fotoinitiator. Eilm eller plader af disse systemer belyses over negativet (eller positivet) af trykforlaget, og de uhærdede bestanddele elueres derefter med et oplesningsmiddel.
Et andet anvendelsesomrâde for W-bærdningen er metalbelæg-ningen, eksempelvis ved lakering af blik til tnber, dâser eller flaskekapsler samt W-hærdning af kunststofbelægnin-ger, eksempelvis af gulv- eller vægbelægninger pâ FVO-basis.
Eksempler pâ UV-hærdning af papirbelœgninger er den farve-lese lakering af etiketter, pladeomslag eller bogomslag.
Ifolge opfindelsen kan forbindelserne med formleme I, II, III og IV ogsâ anvendes som initiatorer til fotokemisk tværbinding af polyolefiner. Pâ taie bertil konmer f.eks. polypropylen, polybuten, polyisobutylen samt copolymerisa-ter, sâsom ethylen-propylen-copolymere, dog fortrinsvis polyetbylen med lav, mellemliggende eller hoj vægtfylde.
Eotoinitiatoreme anvendes til de angivne anvendelsesomrâ-
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cent, fortrinsvis ca. 0,5 til 5 vægtprocent, beregnet pâ systemet, der kan fotopolymeriseres eller tværbindes. Ved System menes herved blandingen af den forbindelse, der kan fotopolymeriseres eller t’værtiindes, fotoinitiatoren og de evrige fyld- og tilsætningsstoffer, som anvendes i den pâ-gældende applikation.
Tilsætningen af fotoinitiatorerne til de fotopolymeriser-bare systemer sker i almndelighed ved simpel ire ring, da , de fleste af disse systemer er flydende eller letoploselige.
For det meste dames en oplesning af de ombandlede initia-torer, ivorved deres ensartede fordeling samt transparensen af polymerisaterne er sikret.
Polymerisationen sker ved de kendte fotopolymerisationsme-toder ved bestrâling med lys, der er rigt pâ kortbelget strâling. Egnede som lyskilder er f.eks. kviksolvmiddel-tryk-, -hejtryk- og -lavtrykstrâlere samt superaktiniske lysstofrer, bvis emissiônsmaksima ligger i omrâdet mellem 250 og 400 nm.
Fremstillingen og anvendelsen af de omhandlede fotoinitia-torer er beskrevet nærmere i de felgende eksempler. Heri betyder dele vægtdele og procenter vægtprocenter.
Fremstilling og egenskaber af de i eksemplerne 1 til 6 anvendte forbindelser.
Fremstillingen af de i tabel 1 anferte forbindelser sker ifelge en eller flere af meto-deme A til L.
Metode A. Cblorering af aromatisk-aliphatiske ketoner
Ar-^00-0^½¾] n + n Cl2 —^ Ar-4C0-CE1E2Cl3;a + n HCl
Til gememforelse oploses ketonen i et inert oplosningsmid- del, fortrinsvis i tetrachlormethan, og ved 40-80°C tille-
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17 des den beregnede mængde cHlor til oplosningen. Derefter til-ledes nitrogen til fjernelse af det opl0ste HCl. Til slut afdestilleres oplosningsmidlet. Eu rensning af den opnâede chlorketon er for det meste ikke nedvendig; produktet kan derefter omsættes ifolge metode D, Τ' eller H.
Metode B. Bromering af aromatisk-alipliatiske ketoner
Ar-tCO-CE1B2H3n + n Br2 —> Ar-tC0-CE1R2Br]n + n HBr
Til germemforelse drypper man ved stuetemperatur den bereg-nede mængde brom til en oplesning af ketonen, eksempelvis i CCl^. Opar"bejdningen og videreforarbejdningen sker som i metode A.
Metode C. Chlorering med sulfurylchlorid
Ar-£-G0-GE1E2H]n + n S02 Cl2 Ar-tGO-CR1E2-Gl]n + n S02 + n HCl
Sulfurylchloridet dryppes ved 40°0 til CCl^-oplesningen af ketonen. Oparbejdning og videreforarbe jdning som ved metode A.
Metode H. Eremstilling af epoxid-mellemprodukterne
Ar-E G0-CE1E2Hal] n + n NaOCH^ Ar-tG^'OE1R23I1 + MaHal OGH-z
O
Hal = Cl eller Br ïïalogenketonen oploses i metlianol, og en oplosning af den stekiometriske mængde natriummetîioxid i metlianol tildryppes ved tilbagesvalingstemperatur. Derefter afdestilleres metbanolet, og remanensen bældes pâ isvand og ekstraberes med etber. Etheroplosningen vaskes med vand, terres over og inddampes. Eemanensen renses ved omkiystallisation
DK 157083B
18 eller vakaumdestillation. Epoxidet kan derefter omsættes ved metode E eller G.
Met ode E. Hydrolyse af epoxiderne ir— 0—(æV + n HgO H > Ar-fCO-CE^OHl + n CH,OH
lAch, Ja 0
Epoxidet overhældes med den 2-til 5-dobbelte vægtmæagde vand og koges under tilsætning af en katalytisk mængde mineral-syre i 1 til 2 timer under tilbagesvaling. Efter afkoling ekstraberes med etber, og etheroplesningen vaskes med vand, torres over og inddampes. Remanensen (râ hydrosy- keton) rens es ved destination eller krystallisation eller se glekromatografi.
Egenskaberne af de rene α-hydroxyketoner er angivet i tabel 1.
Metode E. α-Hydroxyketoner nd fra halogenketoner
Ar-t G0-GE1R2Hal]n + n HaOH Ar-f G0-CR1R20H]n + n NaHal α-Halogenketonen koges i fortyndet eller koncentreret natri-umhydroxidoplosning (20% overskud af NaOH) under tilbagesvaling. Efter endt hydrolyse (kontrol ved kromatografi) isole-res og rens es den râ hydroxyketon som beskrevet i E.
De rene hydroxyketoner er opfert i tabel 1.
Metode G. α-Aminoketoner ud fra epoxiderne
Ar-fd^GR1R2]n + n R^R^NE —> Ar~i 00-011½2^¾¾ n + n CH^OH
OOH-.
y
Epoxidet tvserbindes enten uden oplosningsmiddel eller under 19
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tilsætning af liât toluen eller xylen me à den stekiometri-ske mængde af aminen, og man lader blandingen reagere i ca.
10-20 timer ved 100-200°0. Yed lavtkogende aminer, sâsom dimethylamin eller diethylamin,udf0res reaktionen i auto-klav. Reaktionsblandingen fortyndes med benzen og ekstraheres med fortyndet saltsyre. Den vandige, sure oplosning g0res alkalisk med NaOH og ekstraheres med etlier, og ether-oplosningen vaskes med vand, terres over ïïa^SO^ og inddam-pes. Det opnâede râprodukt renses ved destination eller krystallisation.
α-Aminoketonerne er opfert i tabel 1.
Metode H. α-Aminoketoner ud fra a-halogenketoner
Ar-tC0-0R1E2Hal]n + 2n Ar-0 C0-CR1E2-Ee\^] + n R^E^M^al α-Halogenketonen blandes ufortyndet eller fortyndet med toluen med 2 molækvivalenter af aminen og opvarmes i 10-20 timer til 100-200°C. I tilfælde af lavtkogende aminer, sâsom dimethylamin eller diethylamin ,gennemfores omsætningen i autoklav. Isolering og rensning sker som ved metode G.
Metode I. Indfering af en carbalkoxyethylgruppe CH2CH2C00Alk
Ar-E-00-CHE1-X]n + n 0¾ = CÏÏ-COOAlk-^Ar-E-CO-OE1-^ 3n
Eetonen opleses i dimethylsulfoxid, dertil sætter man 1,1 molækvivalent EaOH i form af 4 K natriumhydroxidoplesning og tildrypper ved stuetemperatur under afkeling 1,1 molækvivalent acrylester. Reaktionsblandingen fortyndes med is-vand og ekstraheres med toluen. Toluenoplesningen vaskes neutral med vand, terres over Es^SO^ og inddampes. Râpro-duktet renses ved sejlekromatografi eller krystallisation.
20
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Netode K. Forethering af hydroxyketoner
Ar-tC0-CR1E2-0H]n + n R6Hal + n RaOÏÏ -> Âr^ C0-CR1R2-0R6]n + n RaHal α-Eydroxyketonen opl0ses i den ca. 4-dobbelte ‘TOsgtmærLgde dimetRylsulf oxid, og under afk0ling til 10-20°G og omrering tildryppes fra to tildrypningstragte samtidig 1 molækvivalent af alkylhalogenidet R^îal og 1 molækvivalent koncentre-ret natrinmRydroxidoplesning. Der omrores derefter i J ti-mer ved stuetemperatur, Rvorefter det udskilte natrium-halogenld frafiltreres, og filtratet fortyndes med etRer, vaskes med vand, terres over og inddampes. Det resul- terende râprodukt renses ved sejlekromatografi, krystalli-sation eller vakuumdestillation. Eksempler pâ anvendelige RalogenforRindelser er metbyliodid, isopropylRromid, allyl-Rromid, cycloRexyrbromid, RenzylcRlorid eller cRloreddike-syreetbylester. I stedet for et aRkylRalogenid kan ogsâ et dialkylsulfat eller alkyl-arylsulfonat anvendes som for-.etReringsreagens.
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0 = 0 · ·· · WW
I //\ ^ / //\ OO
H · · · · ·· \ /
Φ // \ I II I I II X
Ph III I / \ o * · · · · O =· ·
Cq / I //\ I \ / • o · · CO ·=· I I I II I / \ o o · · o · · CO 00 N\ / CO ^ // __3__^_W_ V W__·—· 1 d
•rl CD
,û 01 " "
f-i H
Ο Φ CM CO ^ in MD
fn rd co co ro co co
26 DK 157083 B
!
- J
; i ü Φ « ^ t-i Φ CO ^ MM 7 ra ra - '
•rl ri Φ m ® S
ra φ ·Η ·α -H Π i>a bû H H H n.
fq Φ O O ° g
CQ
bO · ?H * · · •d +> - +i -p 5 «j ni 2 B S S ë
m 0 O O
Φ Sj Jj M
6 Μ Μ M
ra
bD
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i—1 •h d
40 φ U O
ω S « £§ |_*. .. * “ “ . 3 ra φ >d ra
U
f4 Φ
iH
^ m: μ n cm ri w s as a Y ^ ü y y 2: 'd O <n O £ /\ φ o —> O a · * > ü tn O U 1 , mm n _p» ; , 43 K U . K s V / Φ _l O Ο Π O ro Z n rd
Vj m Z ro MO m ro O 00 æ 1 M d § K 1 as Μ 1 M a I a g_—g p
jq u——ο o—-\—ο o——o u j w -P
£ o = i o = u 0 = 0 o = u y
I I I · H
//\ /y \ 'H
• · ·· · · 111 CO
I II I H 1 II i il ·· ·· · · s\ / &
Ns. / d • · · ____43
-- CO
I ^ b g
•H Φ B
rQ ra 5 f-l H ® Ο Φ r-4 I-1 ü, irj r* CO O r^· ^ ü en _ co__^_ _ λ 27
DK 157083 B
Eksempel 1.
En harpiksblanding af 80 dele "Plex 6616" (acrylatharpiks fra firmaet Rohm, Darmstadt), 20 dele trimetbylolpropan-tris-acrylat og 2 dele fotoinitiator udstryges med et filmtrækningsapparat i en tykkelse pâ 40 /im pâ glasplader.
Risse film afluîtes i ca. 20 sekunder og bestrâles derefter med en ïïg-midde11rykbrænder (ïïanovia-Gerat, model 45080).
Derved bevæges provenue pâ et transportbând forbi under en UV-lampe med en sâdan bastigbed, at der resulterer en effektiv belysningstid pâ 0,16 sekunder pr. gennemlob.
I den folgende tabel 2 er der i den anden spalte angivet det antal gennemlob (D), der er nedvendig for at opnâ klæ-befri film.
I den tredie spalte angives nârdlieden af filmene efter for-skellige antal gennemlob, mâlt med et pendulapparat ifpige Konig.
Den sidste spalte viser lagerstabiliteten af barpiks-foto-initiator-blandingen i morke ved 60°C.
28 DK 157083B
Îabel 2
PendulMrdliecL if0lge
Anvendt Kesd-vendig Eonig efter antal lagerstabili-· fotoinitiator genneml0b genneml^b (D)_tet i dage
Nr. 1 4 78 (4D) 94 (6D) 98(8D) >30
Nr. 2 4 . 101(4D) 114(4D) L16(8D) >30
Nr. 24 3 73(5D)
Nr. 26 3 95(3D) 102(4D) L07(5D) >30
Nr. 37 4 47 (3D) 72 (4D) 88(5D) >30 a-Hydroxypro= 3 68(3D) 75(4D) 87(5D) 1 piophenon (sammenlig-ning) a-Méthylbenzoin 5 49(3D) 69(4D) 91(5D) (sammenlig- ning)
Benzoin-tert.- 5 93(5D) 106(7D) L13(9D) -£30 butyl'ther (sammenlig- ning) 2-Phenyl-di- 6 . 112 (6D) 121(80) L30(10D) ? 30 methoxyaceto- phenon (sammenlig- nmg) o-Methyl-α,a-di- 8 92 (8D) lOO(LOd) 1O9 0.2D) ^5 morpholinoace- tophenon (sammenlig- ning) α,α-DimoipholinQ- 17 84CL7D) 98CL9D) <1 acetophenon (sammenlig- ning)______
29 DK 157083 B
Eksempel 2.
Harpiksb 1 andinger af 60 dele "Uvimer DY-530" (uretban-acrylat fra fa. Polycbrom), 37 dele bexandioldiacrylat og 3 dele fotoinitiator udstryges i en filmtykkelse pâ 30 pâ glasplader og belyses som beskrevet i eksempel 1. Derved opnâ felgende resultater.
Babel 3«
Anvendt foto- Eedvendige Pendulh.ârdh.ed if0lge Konig
initiator germemleb til i affteengiglied af D
gnidefasthed
Er. 1 3 129 (3D)
Kr. 2 3 157 (7D)
Diethoxy- acetopbenon 10 136 (10D) (sammenlig- ning)
Benz o in-1 ert.
butyletber 12 136 (12D) (sammenlig- ning) 2-Phenyldi- methoxyaceto- pbenon 8 155 (8D) (sammenlig- ning)
Eksempel 5.
2% fotoinitiator oploses i en umættet polyesterharpiks ("Orystic PEE 306", fa. Maeder, Eillwangen, Schweiz). Disse barpiksblandinger pâfores i en filmtykkelse pâ 60 jLum pâ glasplader. Disse film belyses som beskrevet i eksempel 1.
Den folgende tabel 4- gengiver antallet af gennemlob gennem belysningsapparatet til gnidefasthed af filmene samt pen-dulbârdheden i afhængighed af D.
, DK 157083 B
30 label 4-,
Anvendt Eodvendige Pendulhâr dhed ifelge Konig
fotoinitia- gennemlob i afhængiglied af D
tor til gnide- fastïLed
Er. 1 13 21 (13D) 34- (15D) 62 (17D)
Nr. 2 8 20 (8D) 31 (10D) 89 (12D)
Eksempel 4.
En LarpiEsblanding af 90 dele "Laromer IR 84-96" (acrylat-harpiks fra firmaet EASP, BRD), 10 dele hexandioldiacrylat, 0,5 dele "Bÿk 300" (fly delg ælpemidde 1 fra firmaet ByK-Mallinckrodt, BRD) og 3 dele fotoinitiator til iiærdning un-der luft eller 0,5 dele fotoinitiator til hærdning under nitrogen pâfores med en 15 μ-spiral elektromotorisk pâ karton. Efter en kort afluftningstid udbœrdes med et TTV-ap-parat (model PPG-QC-Pro zessor) med en W-lampe pâ 80 Watt/ cm. I den folgende tabel 5 er angivet den maksimale trans-porthastighed i m/min., hvorved der under lnft, henholdsvis •under nitrogen, opnâs klæbefri film.
label 5»
Anvendt foto- Transporthastighed (m/min.) initiator Lnft Nitrogen
Nr. 5 20 100
Nr. 29 10 90
Nr. 30 _20__ 90_
31 DK 157083 B
Eksempel 5»
En harpiksblanding af 70 dele "Ebecryl 593" (polyester-acrylat fra firmaet UCB, Belgien), 30 dele trimethylol-propantrisacrylat, 0,5 dele "ByK 500" (flydehgælpemiddel fra firmaet ByK-Mallinckrodt, BED) og 3 dele fotoinitiator pâfores med en pâstrygningsramme i en lagtykkelse pâ 30-40 yU/pâ glasplader. Efter en kort afluftningstid udhærdes med et UV-laboratorieapparat (model PPG/Q.C-Prozessor) med en W-lampe pâ 80 ¥att/cm. Efter UY-hærdningen lagres i 1/2 time i normalklima, og derefter bestemmes pendulbârd-beden ifolge Konig. I den fzlgende tabel 6 er angivet de mâlte pendulbârdbeder i afhængigbed af transporthastigbe-den under lampen.
Tabel 6.
Anvendt foto- Pendulhârdbed i sek. initiator 10 m/min. 25 m/min.
Er. 15 150 132
Er. 17 160 144
Er. 21 155 143
Er. 27 162 154
Er. 30 129 98
Nr. 32 146 129
Nr. 35 134 108
Nr. 38 139 " 116
Nr. 40 153 131
Nr. 41 164 152
Claims (5)
1. Anvendelse af aromatisk-aliphatiske ketoner med formlen
0 R1 r 11 I “f Ar—C - C - Z (I) -^2 J n O Z Z 0 fl I , I II Ar-C-G-R^-C-C-Ar (II) *2 *2 & ΈΓ OR1 R1 O Il I lu , Ar - G - C - Σ' -C-C-Ar (III) *2 *2 eller î e1 I (iy) hvori n er 1 eller 2, Ar, nâr n er 1, betyder aryl med 6 til 14 C-atomer, med Cl, Br, CN, OH, alk, -Oalk, -Salk, -S02alk, -S02phenyl, -COOalk, -S02NH2, -S02NHalk eller -S02N(alk)2 substitueret phenyl eller thienyl, pyridyl eller furyl, hvori alk betyder en alkylgruppe med 1 til 4 C-atomer, og nâr n er 2, ' arylen med 6-12 C-atomer eller en gruppe phenylen-T-phenylen-, hvori T betyder -O-, -S-, -SO,-, -CH,- aller -CH=CH-, “ a c ^ ç. IR X er en af grupperne -NR R , -OR eller -0-Si(R )(R°),, in ^ XI er en af grupperne -NR -, -N(phenyl)-, -N-' ^N- eller -N(R10)-R11-N(R10)-, Y er en direkte binding eller -CH2~,
53 DK 15708 3 B Z er -O-, -S-, -SO^-, -CH2“ eller R·*" betyder alkyl med 1-8 C-atomer, der kan være substitueret med OH, C^_^-alkoxy, C2~Cg-acyloxy, -COO-(C^-C^)-alkyl eller -CN, cycloalkyl med 5-6 C-atomer eller phenylalkyl med 7 til 9 C-atomer, 2 1 12 R har en af de for R angivne betydninger, eller R og R betyder sammen alkylen med 4 til 6 C-atomer eller oxa- eller azaalkylen med 3 til 4 C-atomer, 3 R betyder en.direkte binding, alkylen med 1 til 6 C-atomer, oxaalkylen med 2 til 6 C-atomer, phenylen, diphenylen, en gruppe 2 -phenylen-T-phenylen-, eller de to substituenter R sammen med 3 R og de to C-atomer, hvortil disse substituenter er bundet, danner en cyclopentan- eller cyclohexanring, 4 R betyder alkyl med 1 til 12 C-atomer, med -OH eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl, phenylalkyl med 7 til 9 C-atomer, phenyl eller med Cl, alk, OH, -Oalk eller -COOalk substitueret phenyl, 5 R betyder alkyl med 1 til 12 C-atomer, med -OH eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl 4 eller phenylalkyl med 7 til 9 C-atomer, eller sammen med R betyder alkylen med 4 til 5 C-atomer, der kan være afbrudt af -O-, -NH- eller -Nalk-, eller i tilfælde af forbindelser med 2 formlen I sammen med R alkylen eller phenylalkylen med 1 til
9 C-atomer eller oxa- eller azaallylen med 2 til 3 C-atomer, R^ betyder hydrogen, alkyl med 1 til 12 C-atomer, med -OH eller -Oalk substitueret alkyl med 2 til 4 C-atomer, allyl, cyclohexyl, benzyl, phenyl eller med Cl eller alk substitue- 2 ret phenyl, eller sammen med R danner alkylen med 4 til 4 C-atomer, 7 8 R og R er ens eller forskellige og betyder alkyl med 1 til 4 C-atomer eller phenyl, R^ alkyl med 1 til 8.C-atomer, cyclohexyl eller benzyl, og R^ er allylen med 2 til 8 C-atomer, xylylen, phenylen eller en gruppe -phenylen-T-phenylen-, med undtagelse af de forbindelser med formlen I, hvori n er 1, Ar er phenyl eller med Cl, Br, alkyl, alkoxy eller dialkylamino substitueret phenyl, 1 2 X er hydroxy eller alkoxy, og R og R er usubstitueret alkyl, som initiatorer til fotopolymerisation af umasttede forbindel- DK 157083 B
2. Fotopolymeriserbart System, kendetegnet ved, at det bestâr af mindst ên umættet fotopolymeriserbar for-bindelse og 0,1 til 20 vægtprocent, fortrinsvis 0,5 til 5 vægtprocent, af en af de i krav 1 nævnte forbindelser med formlen I, II, III eller IV som fotoinltiator samt even-tuelt yderligere kendte og almindelige tilsætningsstoffer.
3. Fotopolymeriserbart System if0lge krav 2, kendetegnet ved, at det som umættet forbindelse indeholder en eller flere estere af acryl- eller methacrylsyre.
4. Fotopolymeriserbart System if0lge krav 2, kendetegnet ved, at det drejer sig om en trykfarve.
5. Fremgangsmâde til fotopolymerisation af umættede forbindelser, kendetegnet ved, at man som fotoini-tiator anvender en af de i krav 1 nævnte forbindelser med formlen I, II, ni eller IV.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1588477 | 1977-12-22 | ||
CH1588477 | 1977-12-22 | ||
CH251878 | 1978-03-08 | ||
CH251878 | 1978-03-08 | ||
CH972378 | 1978-09-18 | ||
CH972378 | 1978-09-18 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK576278A DK576278A (da) | 1979-06-23 |
DK157083B true DK157083B (da) | 1989-11-06 |
DK157083C DK157083C (da) | 1990-03-19 |
Family
ID=27173751
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK576278A DK157083C (da) | 1977-12-22 | 1978-12-21 | Anvendelse af aromatisk-aliphatiske ketoner som initiatorer til fotopolymerisation af umaettede forbindelser samt til fotokemisk tvaerbinding af polyolefiner, fotopolymeriserbart system indeholdende saadanne ketoner samt fremgangsmaade til fotopolymerisation af umaettede forbindelser |
Country Status (15)
Country | Link |
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US (4) | US4318791A (da) |
EP (1) | EP0003002B1 (da) |
JP (3) | JPS5499185A (da) |
AR (1) | AR226169A1 (da) |
AT (1) | AT369392B (da) |
AU (1) | AU529495B2 (da) |
BR (1) | BR7808406A (da) |
CA (1) | CA1234242A (da) |
DD (1) | DD141320A5 (da) |
DK (1) | DK157083C (da) |
FI (1) | FI64169C (da) |
GR (1) | GR71655B (da) |
HU (1) | HU181680B (da) |
PL (1) | PL117576B1 (da) |
SU (1) | SU948300A3 (da) |
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- 1978-12-18 US US05/970,016 patent/US4318791A/en not_active Expired - Lifetime
- 1978-12-20 GR GR57938A patent/GR71655B/el unknown
- 1978-12-20 FI FI783919A patent/FI64169C/fi not_active IP Right Cessation
- 1978-12-20 CA CA000318328A patent/CA1234242A/en not_active Expired
- 1978-12-21 AT AT0917678A patent/AT369392B/de not_active IP Right Cessation
- 1978-12-21 DK DK576278A patent/DK157083C/da active
- 1978-12-21 AU AU42775/78A patent/AU529495B2/en not_active Expired
- 1978-12-21 BR BR7808406A patent/BR7808406A/pt unknown
- 1978-12-21 SU SU782702501A patent/SU948300A3/ru active
- 1978-12-21 DD DD78210060A patent/DD141320A5/de not_active IP Right Cessation
- 1978-12-21 HU HU78CI1885A patent/HU181680B/hu not_active IP Right Cessation
- 1978-12-22 JP JP16090978A patent/JPS5499185A/ja active Granted
- 1978-12-22 PL PL1978212042A patent/PL117576B1/pl unknown
-
1979
- 1979-12-19 US US06/105,744 patent/US4321118A/en not_active Expired - Lifetime
- 1979-12-28 US US06/108,277 patent/US4308400A/en not_active Expired - Lifetime
- 1979-12-28 US US06/108,276 patent/US4315807A/en not_active Expired - Lifetime
-
1980
- 1980-01-24 AR AR279736A patent/AR226169A1/es active
-
1988
- 1988-10-04 JP JP63250739A patent/JPH01139554A/ja active Granted
-
1989
- 1989-03-15 JP JP1061101A patent/JPH01308404A/ja active Granted
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH459750A (fr) * | 1964-01-29 | 1968-07-15 | Horizons Inc | Procédé de préparation d'un matériel photosensible, matériel photosensible obtenu et utilisation de ce matériel |
FR2013828A1 (da) * | 1968-07-26 | 1970-04-10 | Bayer Ag | |
FR2022723A1 (da) * | 1968-11-06 | 1970-08-07 | Bayer Ag | |
FR2028477A1 (da) * | 1969-01-16 | 1970-10-09 | Bayer Ag | |
US3657088A (en) * | 1969-12-17 | 1972-04-18 | Bayer Ag | Moulding and coating masses hardenable by uv irradiation |
FR2156760A1 (da) * | 1971-10-18 | 1973-06-01 | Ici Ltd | |
FR2162609A1 (en) * | 1971-12-09 | 1973-07-20 | Basf Ag | Printing colour binders - with uv-light hardenable component |
FR2209789A1 (en) * | 1972-12-06 | 1974-07-05 | Sun Chemical Corp | Photosensitive coating composition - contg ethylenically unsatd ester monomer and acyloin deriv as photosensitiser |
Also Published As
Publication number | Publication date |
---|---|
SU948300A3 (ru) | 1982-07-30 |
JPH0257081B2 (da) | 1990-12-04 |
AU4277578A (en) | 1979-06-28 |
FI64169C (fi) | 1983-10-10 |
US4321118A (en) | 1982-03-23 |
BR7808406A (pt) | 1980-05-20 |
JPH0248536B2 (da) | 1990-10-25 |
AT369392B (de) | 1982-12-27 |
DD141320A5 (de) | 1980-04-23 |
PL212042A1 (pl) | 1979-09-10 |
US4308400A (en) | 1981-12-29 |
FI64169B (fi) | 1983-06-30 |
JPH01308404A (ja) | 1989-12-13 |
GR71655B (da) | 1983-06-20 |
EP0003002B1 (de) | 1984-06-13 |
EP0003002A2 (de) | 1979-07-11 |
FI783919A (fi) | 1979-06-23 |
US4315807A (en) | 1982-02-16 |
EP0003002A3 (en) | 1980-01-09 |
ATA917678A (de) | 1982-05-15 |
JPH0134242B2 (da) | 1989-07-18 |
DK157083C (da) | 1990-03-19 |
JPS5499185A (en) | 1979-08-04 |
AR226169A1 (es) | 1982-06-15 |
PL117576B1 (en) | 1981-08-31 |
AU529495B2 (en) | 1983-06-09 |
DK576278A (da) | 1979-06-23 |
CA1234242A (en) | 1988-03-15 |
HU181680B (en) | 1983-11-28 |
US4318791A (en) | 1982-03-09 |
JPH01139554A (ja) | 1989-06-01 |
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