NL8104346A - PHOTHARDISABLE MATERIALS AND METHOD FOR THE MANUFACTURE OF HARDENED PRODUCTS THEREOF. - Google Patents
PHOTHARDISABLE MATERIALS AND METHOD FOR THE MANUFACTURE OF HARDENED PRODUCTS THEREOF. Download PDFInfo
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- NL8104346A NL8104346A NL8104346A NL8104346A NL8104346A NL 8104346 A NL8104346 A NL 8104346A NL 8104346 A NL8104346 A NL 8104346A NL 8104346 A NL8104346 A NL 8104346A NL 8104346 A NL8104346 A NL 8104346A
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- Netherlands
- Prior art keywords
- curing
- group
- exotherm
- formula
- compound
- Prior art date
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- 239000000463 material Substances 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229920006295 polythiol Polymers 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- -1 azo compound Chemical class 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000001451 organic peroxides Chemical class 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 238000001723 curing Methods 0.000 description 98
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 26
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 20
- PYKCEDJHRUUDRK-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylpropanenitrile Chemical compound CC(C)(C)N=NC(C)(C)C#N PYKCEDJHRUUDRK-UHFFFAOYSA-N 0.000 description 14
- 239000004342 Benzoyl peroxide Substances 0.000 description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 12
- 235000019400 benzoyl peroxide Nutrition 0.000 description 12
- 150000002978 peroxides Chemical class 0.000 description 12
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 8
- 150000004291 polyenes Chemical class 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 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 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 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
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002195 synergetic effect Effects 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
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- 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
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 1
- LXWYWFVEVDLKQM-UHFFFAOYSA-N 1,3-bis[2-(2-phenylpropan-2-ylperoxy)propan-2-yl]benzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C(C=1)=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 LXWYWFVEVDLKQM-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- KAJBSGLXSREIHP-UHFFFAOYSA-N 2,2-bis[(2-sulfanylacetyl)oxymethyl]butyl 2-sulfanylacetate Chemical compound SCC(=O)OCC(CC)(COC(=O)CS)COC(=O)CS KAJBSGLXSREIHP-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- QYXHDJJYVDLECA-UHFFFAOYSA-N 2,5-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=O)C=C1C1=CC=CC=C1 QYXHDJJYVDLECA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-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
- 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
- DNNDHIKCLIZHBH-UHFFFAOYSA-N 2-(oxan-2-yloxy)-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1CCCCO1 DNNDHIKCLIZHBH-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FZUNCODNAAEALR-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1.CC(C)(C)OOC(C)(C)C FZUNCODNAAEALR-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- QLZINFDMOXMCCJ-UHFFFAOYSA-N 7-(7-hydroxyheptylperoxy)heptan-1-ol Chemical compound OCCCCCCCOOCCCCCCCO QLZINFDMOXMCCJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 235000008098 Oxalis acetosella Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002176 Pluracol® Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 244000126309 Trifolium dubium Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- BRHJUILQKFBMTL-UHFFFAOYSA-N [4,4-bis(dimethylamino)cyclohexa-1,5-dien-1-yl]-phenylmethanone Chemical compound C1=CC(N(C)C)(N(C)C)CC=C1C(=O)C1=CC=CC=C1 BRHJUILQKFBMTL-UHFFFAOYSA-N 0.000 description 1
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical compound [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KUXMPPPSUQZGRR-UHFFFAOYSA-N bis(2-ethenylphenyl) carbonate Chemical compound C=CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1C=C KUXMPPPSUQZGRR-UHFFFAOYSA-N 0.000 description 1
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 description 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 1
- CJKWEXMFQPNNTL-UHFFFAOYSA-N bis(prop-2-enyl) 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylate Chemical compound C=CCOC(=O)C1C(C(=O)OCC=C)C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl CJKWEXMFQPNNTL-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- LKFAPHHHWRMPGC-UHFFFAOYSA-N butan-1-ol prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C LKFAPHHHWRMPGC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 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
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
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
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
Description
η - 1 -η - 1 -
Fotohardbare materialen alsmede werkwijze voor de vervaardiging van geharde produkten daaruit.Photo-curable materials as well as a method of manufacturing cured products therefrom.
De uitvinding heeft betrekking op eenThe invention relates to a
i door straling hardhaar materiaal. Meer in het bijzonder heeft deJi by radiation hard hair material. More specifically, deJ
uitvinding betrekking op een door straling geactiveerd materiaal dat vloeibare di- en poly-acryl-getermineerde monomeren, oligo- j ; 5 meren of prepolymeren, hierna aangeduid als ethenisch onver-j zadigde verbinding, in combinatie met een niet-stikstof-bevat- tende foto-initiator en een synergistisch middel uit de groep bestaande uit een azoverbinding en een organisch peroxyde, omvat .invention relates to a radiation activated material comprising liquid di- and poly-acrylic terminated monomers, oligoj; 5 or prepolymers, hereinafter referred to as ethylenically unsaturated compound, in combination with a non-nitrogen-containing photoinitiator and a synergist from the group consisting of an azo compound and an organic peroxide.
10 De uitvinding heeft tevens betrekking op een werkwijze voor het vormen van geharde materialen uit het | voornoemde materiaal, die kunnen worden gebruikt als deklagen, ! pakkingen, afsluitmiddelen, resisten en dergelijke.The invention also relates to a method for forming hardened materials from the the aforementioned material, which may be used as coatings,! gaskets, sealing means, resistances and the like.
Hardbare bekledingen die peroxyden be-15 vatten zijn reeds bekend.Curable coatings containing peroxides are already known.
Het Amerikaanse octrooischrift 3.662.023 ! beschrijft een materiaal dat in hoofdzaak bestaat uit een allyl- ; getermineerd polyeen en een polythiol in combinatie met een j organisch peroxyde of hydroperoxyde dat bij blootstelling aan i 20 warmte geharde polythioëthers vormt.U.S. Patent 3,662,023! describes a material consisting essentially of an allyl; terminated polyene and a polythiol in combination with an organic peroxide or hydroperoxide which forms heat-cured polythioethers upon exposure.
Het Amerikaanse octrooischrift 4.222.835 beschrijft een TJV-hardbaar materiaal, omvattende een vloeibaar vinylmonomeer, een UV-geactiveerde foto-initiator, een thermische initiator, zoals een peroxyde of hydroperoxyde en een 25 versneller die in staat is de temperatuur waarbij de genoemde thermische initiator wordt geactiveerd te verlagen, omvattende een amine of een amide.US Patent 4,222,835 discloses a TJV curable material comprising a liquid vinyl monomer, a UV activated photoinitiator, a thermal initiator such as a peroxide or hydroperoxide and an accelerator capable of temperature at which said thermal initiator is activated, including an amine or an amide.
Het Canadese octrooischrift 1.076.296 beschrijft een fotopolymeriseerbaar materiaal dat geschikt is 30 voor tandbekledingsdoeleinden, omvattende een diacrylaat-ge- termineerd oligomeer, een alifatisch acrylaatmonomeerverdunnings-middel, een organisch peroxyde vrij-radicaal-initiator en een 8104346 - 2 - 4 fotosensibiliseermiddel, dat 4,4,-bis(dimethylamino)-benzofenon omvat. |Canadian Patent 1,076,296 discloses a photopolymerizable material suitable for dental coating purposes, comprising a diacrylate-terminated oligomer, an aliphatic acrylate monomer diluent, an organic peroxide free-radical initiator and a 8104346-2-4 photosensitizer. 4,4 bis (dimethylamino) benzophenone. |
Opgemerkt moet worden dat in de beide laatstgenoemde UV-hardbare materialen volgens de stand van de I 5 techniek een amine aanwezig is, hetzij als zodanig als versnel- ! lingsmiddel, hetzij als groep-gedeelte in het fotosensibiliseer- middel teneinde een kleefvrij oppervlak na harding van het ma teriaal te verkrijgen.It should be noted that in the last two UV curable materials of the prior art mentioned above, an amine is present, either as such as accelerator. release agent, or as a group portion in the photosensitizer to obtain a tack-free surface after curing the material.
Een doel van de onderhavige uitvinding 10 is een materiaal te produceren dat bij blootstelling aan UV-straling resulteert in een door-en-door gehard materiaal met een kleefvrij oppervlak. Een ander doel van de uitvinding is een materiaal te produceren dat bij blootstelling aan UV-straling een versnelde hardingssnelheid heeft. Andere doeleinden zullen 15 duidelijk worden uit het onderstaande.An object of the present invention is to produce a material which, when exposed to UV radiation, results in a thoroughly hardened material with an tack-free surface. Another object of the invention is to produce a material that has an accelerated cure rate when exposed to UV radiation. Other purposes will become apparent from the following.
De uitvinding heeft betrekking op een UV-hardingsproces en op een UV-geactiveerd materiaal dat in hoofdzaak bestaat uit: (1) een vloeibare ethenisch onverzadigde ; 20 verbinding van formule 1, waarin R H of CH^ is, een organi- i sche groep met de waardigheid n is en n tenminste 2 is, (2) een niet-stikstofhoudende foto- initiator en (3) een synergistisch middel uit de 25 groep bestaande uit een azoverbinding en een organisch peroxyde van formule 2, waarin n 0 of 1 is, R en R^ onafhankelijk van elkaar zijn gekozen uit waterstof, aryl, alkyl, arylcarbonyl, alkarylcarbonyl, aralkylcarbonyl en alkylcarbonyl en Rj alkyl of aryl is, waarbij de genoemde alkylgroepen 1 tot 20 koolstofato-30 men bevatten. Bij blootstelling aan UV-straling worden zeer snelle hardingen verkregen.The invention relates to a UV curing process and to a UV-activated material consisting essentially of: (1) a liquid ethylenically unsaturated; Compound of formula 1, wherein RH or CH 2 is an organic group of the value n and n is at least 2, (2) a non-nitrogenous photoinitiator and (3) a synergist from the 25 group consisting of an azo compound and an organic peroxide of formula 2, wherein n is 0 or 1, R and R 4 are independently selected from hydrogen, aryl, alkyl, arylcarbonyl, alkarylcarbonyl, aralkylcarbonyl and alkylcarbonyl and R 1 is alkyl or aryl, wherein said alkyl groups contain 1 to 20 carbon atoms. Very fast cures are obtained when exposed to UV radiation.
Ofschoon de voornoemde materialen als zodanig bruikbaar zijn voor het vormen van nuttige produkten kunnen ze ook worden gebruikt in combinatie met conventionele 35 copolymeriseerbare monomere verbindingen of reactieve verdunnings-middelen. Het mengen van het materiaal volgens de uitvinding met 8104346 Λ Λ - 3 - andere monomeren wordt gewoonlijk toegepast om de viscositeit en andere toepassingsvariabelen zoals de hardingssnelheid als- j mede uiteindelijke film- of deklaag-eigenschappen zoals hardheid | en buigzaamheid te beheersen. Deze reactieve verdunningsmiddelen 5 harden tezamen met de ethenisch onverzadigde verbinding bij blootstelling aan UV-straling en warmte. Voorbeelden van conventionele copolymeriseerbare verbindingen die bruikbaar zijn als reactieve verdunningsmiddelen omvatten, maar zijn niet beperkt tot, monofunctionele acrylesters, monofunctionele methacryl-10 esters, styreen, vinyltolueen, acrylonitril, methacrylonitril, vinylacetaat, vinylpyrrolidon, vinylchloride, vinylideen-chloride, butadieen, isopreen, chloropreen, divinylbenzeen, di(vinylfenyl)carbonaat, diallylftalaat, diallylcarbonaat, di-(allylfenyl)carbonaat, diallylfumaraat, triallyl-isocyanuraat, 15 triallylcyanuraat, diallylchlorendaat, diallylmaleaat en onverzadigde polyesters en mengsels daarvan. Met de term onverzadigde j polyesters wordt hier bedoeld de gebruikelijke polycondensatie- produkten welke bestaan uit esterachtig verknoopte residuen van ] polyvalente, in het bijzonder divalente, alkoholen, alsmede 20 eventueel ook residuen van monovalente alkoholen en/of van monovalente carbonzuren, waarbij de residuen tenminste gedeelte- lijk onverzadigde groepen moeten bevatten. Voorbeelden van zuren omvatten maleïnezuur, fumaarzuur, itaconzuur, mesaconzuur, citraconzuur, barnsteenzuur, glutaarzuur, adipinezuur, ftaalzuur,: 25 tetrachloorftaalzuur, hexachloorendomethyleentetrahydroftaal- zuur, trimellietzuur, benzoëzuur, lijnolievetzuur en ricinus-olie-vetzuur en mengsels daarvan. Voorbeelden van alkoholen omvatten ethyleenglycol, diethyleenglycol, propaan-, butaan- en hexaan-diolen, trimethylolpropaan, pentaerythritol, butanol en 30 tetrahydrofurfurylalkohol.Although the aforementioned materials are useful as such for forming useful products, they can also be used in combination with conventional copolymerizable monomer compounds or reactive diluents. Mixing the material of the invention with 8104346 Λ Λ - 3 - other monomers is commonly used for viscosity and other application variables such as cure speed as well as final film or coating properties such as hardness | and flexibility. These reactive diluents cure together with the ethylenically unsaturated compound upon exposure to UV radiation and heat. Examples of conventional copolymerizable compounds useful as reactive diluents include, but are not limited to, monofunctional acrylic esters, monofunctional methacrylic esters, styrene, vinyl toluene, acrylonitrile, methacrylonitrile, vinyl acetate, vinyl pyrrolidone, vinyl chloride, vinylidene chloride, butadiene, isoprene chloroprene, divinylbenzene, di (vinylphenyl) carbonate, diallyl phthalate, diallyl carbonate, di- (allyl phenyl) carbonate, diallyl fumarate, triallyl isocyanurate, triallyl cyanurate, diallyl chlorendate, diallyl maleate and unsaturated polyesters, and mixtures thereof. By the term unsaturated polyesters is meant here the usual polycondensation products which consist of ester-like cross-linked residues of polyvalent, in particular divalent, alcohols, as well as optionally also residues of monovalent alcohols and / or of monovalent carboxylic acids, the residues being at least must contain partially unsaturated groups. Examples of acids include maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, succinic acid, glutaric acid, adipic acid, phthalic acid, tetrachlorophthalic acid, hexachloromethylene tetrahydrophthalic acid, trimellitic acid, benzoic acid, linseed oil and castor oil fatty acid and mixtures thereof. Examples of alcohols include ethylene glycol, diethylene glycol, propane, butane and hexane diols, trimethylol propane, pentaerythritol, butanol and tetrahydrofurfuryl alcohol.
De reactieve verdunningsmiddelen kunnen aan het systeem worden toegevoegd in hoeveelheden lopend opwaarts tot 90 gew.% van de ethenisch onverzadigde verbinding, bij voorkeur 20 tot 50 gew.% op dezelfde basis.The reactive diluents can be added to the system in amounts up to 90% by weight of the ethylenically unsaturated compound, preferably 20 to 50% by weight on the same basis.
35 Een klasse van niet-stikstofhoudende foto-initiatoren zijn de carbonylverbindingen met tenminste één 8104346 % - 4 - ! aromatische kern rechtstreeks gehecht aan de groepjvan formule 3, ! waarbij eventuele substituenten aan hetzij de aromatische kern j | hetzij de carbonylgroep beperkt zijn tot atomen gekozen uit de ! groep bestaande uit koolstof, zuurstof, waterstof, chloor, 5 fosfor, zwavel en combinaties daarvan. Diverse foto-initiatoren van dit type omvatten, maar zijn niet beperkt tot, benzofenon, acetofenon, o-methoxy-benzofenon, dibenzosuberon, 4*-methoxy-acetofenon, benzaldehyde, 10-thioxanthen-9-on, xanthreen-9-on, 7-H-benz/ de_/anthracen-7-on, 1-nafthaldehyde, 2'-acetonafthon, 10 acetonafthon, benz/ a_7anthraceen-7.12-dion, 2,2,2-trichloor-4-tH butylacetofenon; 2-hydroxy-2-methyl-l-fenyl-propaan-l-on; benzoïne-methylether, benzoïn-ethylether, benzoïne-isopropylether, benzoïne-isobutylether, benzoïne-tetrahydropyranyl-ether, 2.2- dimethoxy-2-fenylacetofenon en benzil-dimethyl-ketal. Meng-15 seis van fotoïnitiatoren zijn bruikbaar. De foto-initiator of mengsels daarvan worden gewoonlijk toegevoegd in een hoeveelheid : lopend van 0,0005 tot 30 gew.% van de ethenisch onverzadigde verbinding.A class of non-nitrogenous photoinitiators are the carbonyl compounds with at least one 8104346% - 4 -! aromatic nucleus directly attached to the group of formula 3! where any substituents on either the aromatic core j | or the carbonyl group is limited to atoms selected from the! group consisting of carbon, oxygen, hydrogen, chlorine, phosphorus, sulfur and combinations thereof. Various photoinitiators of this type include, but are not limited to, benzophenone, acetophenone, o-methoxy-benzophenone, dibenzosuberone, 4-methoxy-acetophenone, benzaldehyde, 10-thioxanthen-9-one, xanthrene-9-one, 7-H-benz / de-anthracen-7-one, 1-naphthaldehyde, 2'-acetone-afthon, acetone-afthon, benz / a-7-anthracene-7,12-dione, 2,2,2-trichloro-4-t-butyl acetophenone; 2-hydroxy-2-methyl-1-phenyl-propan-1-one; benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin tetrahydropyranyl ether, 2,2-dimethoxy-2-phenylacetophenone and benzil dimethyl ketal. Mixing 15 of photoinitiators are useful. The photoinitiator or mixtures thereof are usually added in an amount ranging from 0.0005 to 30% by weight of the ethylenically unsaturated compound.
De organische peroxyden die bruikbaar 20 zijn als synergistische middelen voldoen aan de algemene formule ; 2, waarinn 0 of 1 is, R en onafhankelijk van elkaar gekozen zijn uit waterstof, aryl, alkyl, arylcarbonyl, alkarylcarbonyl, aralkylcarbonyl en alkylcarbonyl en Rj alkyl of aryl is, waarbij de genoemde alkylgroepen 1 tot 20 koolstofatomen bevatten.The organic peroxides useful as synergists meet the general formula; 2, wherein 0 is 1 or 1, R and are independently selected from hydrogen, aryl, alkyl, arylcarbonyl, alkarylcarbonyl, aralkylcarbonyl and alkylcarbonyl, and R 1 is alkyl or aryl, said alkyl groups containing 1 to 20 carbon atoms.
25 Voorbeelden van bruikbare organische peroxyden omvatten, maar zijn niet beperkt tot, 2,5-dimethyl- 2,5-di(t-butylperoxy)hexaan, 1,3-bis(t-butylperoxyisopropyl)benzéen, 1.3- bis(cumylperoxyisopropyl)benzeen, 2,4-dichloorbenzoylperoxyde, caprylyl-peroxyde, lauroylperoxyde, t-butylperoxyisobutyraat, 30 benzoylperoxyde, p-chloorbenzoylperoxyde, hydroxyheptyl-per-oxyde, di-t-butyl-diperftalaat, t-butyl-peracetaat, t-butyl-perbenzoaat, dicumylperoxyde, t-butyl-hydroperoxyde en di-t-butylperoxyde.Examples of useful organic peroxides include, but are not limited to, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane, 1,3-bis (t-butylperoxyisopropyl) benzene, 1,3-bis (cumylperoxyisopropyl) benzene, 2,4-dichlorobenzoyl peroxide, caprylyl peroxide, lauroyl peroxide, t-butyl peroxyisobutyrate, benzoyl peroxide, p-chlorobenzoyl peroxide, hydroxyheptyl peroxide, di-t-butyl diperphthalate, t-butyl peracylate, , dicumyl peroxide, t-butyl hydroperoxide and di-t-butyl peroxide.
Het organische peroxyde wordt toegevoegd : 35 aan het materiaal in een hoeveelheid lopend van 0,001 tot 5,0, bij voorkeur 0,01 tot 2 gew.%, betrokken op het gewicht van de 8104346 - 5 - I ethenisch onverzadigde verbinding.The organic peroxide is added: 35 to the material in an amount ranging from 0.001 to 5.0, preferably 0.01 to 2% by weight, based on the weight of the 8104346-5 ethylenically unsaturated compound.
i I Voorbeelden van azoverbindingen die bruikbaar zijn als synergistische middelen omvatten, maar zijn ! | niet beperkt tot, in de handel verkrijgbare verbindingen, zoals 5 2-t-butylazo-2-cyaanpropaan; 2,2,-azobis(2,4-dimethyl-4-methoxy- valeronitril); 2,2'-azobis(isobutyronitril); 2,2T-azobis(2,4-dimethylvaleronitril) en 1,1’-azobis(cyclohexaancarbonitril).Examples of azo compounds useful as synergists include, but are not limited to! | not limited to commercially available compounds, such as 5 2-t-butylazo-2-cyanopropane; 2,2,1-azobis (2,4-dimethyl-4-methoxyvaleronitrile); 2,2'-azobis (isobutyronitrile); 2,2T-azobis (2,4-dimethylvaleronitrile) and 1,1'-azobis (cyclohexane carbonitrile).
De azoverbinding wordt aan het materiaal toegevoegd in een hoeveelheid lopend van 0,001 tot 5, bij voor-10 keur 0,01 tot 2 gew.%, betrokken op het gewicht van de ethenisch onverzadigde verbinding.The azo compound is added to the material in an amount ranging from 0.001 to 5, preferably 0.01 to 2% by weight, based on the weight of the ethylenically unsaturated compound.
Het synergistische middel kan aan het systeem worden toegevoegd op diverse wijzen. Dat wil zeggen het synergistische middel als zodanig kan worden gemengd met de 15 ethenische onverzadigde verbinding. Verder kan het worden ge mengd met een foto-initiator en worden toegevoegd aan de ethenisch onverzadigde verbinding. Verder kan het organische peroxyde wor- ; j den opgelost of gesuspendeerd in algemeen bekende in de handel i verkrijgbare oplosmiddelen, zoals dibutylftalaat; ketonen, bij-20 voorbeeld aceton en methylethylketon; of gechloreerde koolwaterstoffen, zoals methyleenchloride, en daarna worden toegevoegd aan het systeem.The synergistic agent can be added to the system in various ways. That is, the synergist as such can be mixed with the ethylenically unsaturated compound. Furthermore, it can be mixed with a photoinitiator and added to the ethylenically unsaturated compound. Furthermore, the organic peroxide can be; dissolved or suspended in well known commercially available solvents such as dibutyl phthalate; ketones, for example, acetone and methyl ethyl ketone; or chlorinated hydrocarbons, such as methylene chloride, and then added to the system.
Bij het in de praktijk brengen van de onderhavige uitvinding is het soms wenselijk een polythiol aan 25 het materiaal toe te voegen voorafgaand aan de harding. Een der-I gelijke toevoeging van een polythiol aan het systeem helpt het optreden van een kleverig oppervlak ten gevolge van luchtinhibitie van de harding te voorkomen.In practicing the present invention, it is sometimes desirable to add a polythiol to the material prior to curing. Such addition of a polythiol to the system helps prevent the appearance of a tacky surface due to air inhibition of the curing.
Zoals hier gebruikt heeft de term poly-30 thiolen betrekking op eenvoudige of complexe organische verbindingen met meerdere zijstandige of eindstandig gesitueerde functionele SH-groepen per gemiddeld molecuul.As used herein, the term poly-thiols refers to simple or complex organic compounds with multiple SH side-chain or terminal functional groups per average molecule.
Gemiddeld moeten de polythiolen twee of meer SH-groepen per molecuul bevatten en gewoonlijk hebben de 1 | 35 polythiolen een viscositeitstraject van iets meer dan nul tot 20 miljoen cP bij 70°C, als gemeten door een Brookfield Visco- 8104346 ♦ - 6 - meter. Binnen de term "polythiolen" als hier gebruikt vallen die materialen welke in aanwezigheid van een inert oplosmiddel, waterige dispersie of weekmaker binnen het hierboven aangegeven viscositeitstraject vallen bij 70°C. Bruikbare polythiolen in 5 de onderhavige uitvinding hebben gewoonlijk molecuulgewichten in het traject van 94 tot 20.000, bij voorkeur 100 tot 10.000.On average, the polythiols must have two or more SH groups per molecule and usually have the 1 | Polythiols have a viscosity range of just over zero to 20 million cP at 70 ° C, as measured by a Brookfield Visco 8104346-6 meter. Within the term "polythiols" as used herein are those materials which, in the presence of an inert solvent, aqueous dispersion or plasticizer, fall within the above viscosity range at 70 ° C. Polythiols useful in the present invention usually have molecular weights in the range of from 94 to 20,000, preferably from 100 to 10,000.
De in de onderhavige uitvinding bruikbare polythiolen kunnen bijvoorbeeld worden weergegeven door de algemene formule 4, waarin n tenminste 2 is en Rg een polyvalente 10 organische groep is die vrij is van reactieve koolstof-koolstof-onverzadigdheid. Zo kan Rg cyclische groeperingen en kleine hoe-; veelheden heteroatomen zoals S, P of 0 bevatten, maar op de eer ste plaats bevat Rg koolstof-waterstof-, koolstof-zuurstof- of silicium-zuurstof-bevattende ketenverknopingen, vrij van elke 15 reactieve koolstof-koolstof-onverzadigdheid.For example, the polythiols useful in the present invention may be represented by the general formula 4, wherein n is at least 2 and Rg is a polyvalent organic group free of reactive carbon-carbon unsaturation. For example, Rg can form cyclic groupings and small how; contain many heteroatoms such as S, P or O, but first of all Rg contains carbon-hydrogen, carbon-oxygen or silicon-oxygen-containing chain cross-links, free from any reactive carbon-carbon unsaturation.
Een klasse van polythiolen die bruikbaar is in de onderhavige uitvinding voor het verkrijgen van nagenoeg' geurloze polythioëtherprodukten zijn esters van thiolhoudende zuren van de algemene formule 5, waarin RQ een organische groep y 20 is die geen "reactieve" koolstof-koolstof-onverzadigdheid bevat, met polyhydroxyverbindingen van de algemene formule 6, waarin Rjq een organische groep is die geen "reactieve" koolstof-kool- ! stof-onverzadigdheid bevat en n 2 of meer is. Deze componenten zullen onder geschikte omstandigheden reageren onder verschaf-25 fing van een polythiol van formule 7, waarin R^ en Rjq organische groepen zijn die geen "reactieve" koolstof-koolstof-onverzadigd-' heid bevatten en n 2 of meer is.A class of polythiols useful in the present invention for obtaining substantially odorless polythioether products are esters of thiol-containing acids of the general Formula 5 wherein RQ is an organic group y 20 which contains no "reactive" carbon-carbon unsaturation, with polyhydroxy compounds of the general formula 6, wherein R iq is an organic group which is not "reactive" carbon-carbon! contains material unsaturation and n is 2 or more. These components will react under suitable conditions to provide a polythiol of formula 7, wherein R 1 and R 8 are organic groups that do not contain "reactive" carbon-carbon unsaturation and n is 2 or more.
Bepaalde polythiolen, zoals de alifa-tische monomere thiolen (ethaan-dithiol, hexamethyleen-dithiol, 30 decamethyleen-dithiol, tolyleen-2,4-dithiol, etc.) en enige polymere polythiolen, zoals een thiol-getermineerd ethylcyclo-hexyldimercaptanpolymeer, enz., en soortgelijke polythiolen welke op geschikte wijze en gewoonlijk worden gesynthetiseerd op commerciële basis, ofschoon ze onaangename geuren hebben, 35 zijn bruikbaar in de onderhavige uitvinding, maar veel van de eindprodukten worden niet algemeen aanvaard uit praktisch com- 8104346 - 7 - I mercieel oogpunt. Voorbeelden van de voor de onderhavige uitvin- | ding geprefereerde polythiolverbïndingen in verband met hun | relatief lage geurniveau omvatten, maar zijn niet beperkt tot, esters van thioglycolzuur (HS-Cï^COOH), a-mercaptopropionzuur 5 (HS-CHCCH^-COOH) en g-mercaptopropionzuur (HS-CI^Cl^COOH) met polyhydroxy-verbindingen zoals glycolen, triolen, tetraolen, pentaolen, hexaolen, enz. Specifieke voorbeelden van de voorkeur verdienende polythiolen omvatten, maar zijn niet beperkt tot, ethyleen-glycol-bis-(thioglycolaat), ethyleenglycol-10 bis(g-mercaptopropionaat), trimethylolpropaan-tris(thio-glyco-laat), trimethylolpropaan-tris(g-mercapto-propionaat), penta-erythritol-tetrakis(thioglycolaat) en pentaërythritol-tetrakis-(g-mercaptopropionaat), welke alle in de handel verkrijgbaar zijn. Een specifiek voorbeeld van een geprefereerde polymere 15 polythiol is polypropyleen-ether-glycol-bis(g-mercaptopropionaat) die wordt bereid uit polypropyleenetherglycol (bijvoorbeeld Pluracol P2010, Wyandotte Chemical Corp.) en g-mercapto-propionzuur door verestering.Certain polythiols, such as the aliphatic monomeric thiols (ethane-dithiol, hexamethylene-dithiol, decamethylene-dithiol, tolylene-2,4-dithiol, etc.) and some polymeric polythiols, such as a thiol-terminated ethylcyclohexyl dimercaptan polymer, etc. ., and similar polythiols which are suitably and usually synthesized on a commercial basis, although they have unpleasant odors, are useful in the present invention, but many of the end products are not generally accepted from practical commercial practice. point of view. Examples of the for the present invention thing preferred polythiol compounds in connection with their relatively low odor levels include, but are not limited to, esters of thioglycolic acid (HS-Cl 2 COOH), α-mercaptopropionic acid (HS-CHCCH 1 -COOH) and g-mercaptopropionic acid (HS-C 1 Cl 2 COOH) with polyhydroxy- compounds such as glycols, triols, tetraols, pentaols, hexaols, etc. Specific examples of preferred polythiols include, but are not limited to, ethylene glycol bis (thioglycolate), ethylene glycol 10 bis (g-mercaptopropionate), trimethylol propane tris (thio-glycolate), trimethylolpropane-tris (g-mercapto-propionate), pentaerythritol-tetrakis (thioglycolate) and pentaerythritol-tetrakis (g-mercaptopropionate), all of which are commercially available. A specific example of a preferred polymeric polythiol is polypropylene ether glycol bis (g-mercaptopropionate) prepared from polypropylene ether glycol (eg Pluracol P2010, Wyandotte Chemical Corp.) and g-mercapto-propionic acid by esterification.
Voorts omvatten polythiolen die hier 20 bruikbaar zijn ter verschaffing van geharde vaste polythio- etherprodukten met de ethenisch onverzadigde verbinding (polyeen) de mercapto-esterderivaten van styreen-allylalkohol-copolymeren, beschreven in het Amerikaanse octrooischrift 3.904.499 en de isocyanuraat-bevattende polythiolen beschreven in het Amerikaanse 25 octrooischrift 3.676.440 en vloeibare thiol-getermineerde polymeren bereid in overeenstemming met het Amerikaanse octrooischrift 3.258.495. Een voorbeeld van een vloeibaar thiol-getermineerd polymeer van het laatstgenoemde type is CAPCURE 3-800, commercieel verkrijgbaar bij Diamond Shamrock Chemical Company.Furthermore, polythiols useful herein to provide cured solid polythioether products with the ethylenically unsaturated compound (polyene) include the mercapto ester derivatives of styrene-allyl alcohol copolymers described in U.S. Patent 3,904,499 and the isocyanurate-containing polythiols. in U.S. Patent 3,676,440 and liquid thiol-terminated polymers prepared in accordance with U.S. Patent 3,258,495. An example of a liquid thiol-terminated polymer of the latter type is CAPCURE 3-800, commercially available from Diamond Shamrock Chemical Company.
30 De voorkeur verdienende polythiolverbin- dingen worden gekenmerkt door een laag niveau van mercaptan-achtige geur aanvankelijk en na reactie geven ze nagenoeg geurloze polythioëther-eindprodukten welke commercieel aantrekkelijk zijn en in de praktijk bruikbare harsen of elastomeren voor 35 toepassingen zowel binnen- als buitenshuis.Preferred polythiol compounds are characterized by a low level of mercaptan-like odor initially and upon reaction give substantially odorless polythioether end products which are commercially attractive and practical resins or elastomers for both indoor and outdoor applications.
Opgemerkt dient te worden dat teneinde 8104346 - 8 - de maximale sterkte, oplosmiddelbestendigheid, kruipweerstand, ! i warmtebestendigheid en vrijheid van kleverigheid te verkrijgen jIt should be noted that in order 8104346 - 8 - the maximum strength, solvent resistance, creep resistance,! i obtain heat resistance and freedom from stickiness j
j Ij I
| de reactiecomponenten, bestaande uit de polyeen en polythiol van deze uitvinding opzodanige wijze worden samengesteld dat 5 vaste, verknoopte, driedimensionele netwerkpolythioëtherpoly-meersystemen worden verkregen bij harding. Teneinde zulke oneindige netwerkvorming te verwezenlijken moeten de individuele | polyenen en polythiolen een functionaliteit van tenminste 2 heb- ; ben en moet de som van de functionaliteiten van de polyeen- en 10 polythiol-componenten steeds groter dan 4 zijn. Hengsels van de polyenen en de polythiolen die de genoemde functionaliteit bevatten zijn ook bruikbaar in de onderhavige uitvinding.| the reactants consisting of the polyene and polythiol of this invention are formulated in such a way that 5 solid, cross-linked, three-dimensional network polythioether polymer systems are obtained upon curing. In order to achieve such infinite networking, individual | polyenes and polythiols have a functionality of at least 2; the sum of the functionalities of the polyene and polythiol components must always be greater than 4. Handles of the polyenes and polythiols containing said functionality are also useful in the present invention.
Wanneer een polythiol wordt gebruik in | | combinatie met de ethenisch onverzadigde verbinding kan de hoe- 15 veelheid polythiol gebruikt voor het bereiden van het hardbare materiaal variëren opwaarts tot een stoechiometrische hoeveelheid vereist om te reageren met alle in de verbinding aanwezige ethenisch onverzadigde groepen.When a polythiol is used in | | in combination with the ethylenically unsaturated compound, the amount of polythiol used to prepare the curable material may vary up to a stoichiometric amount required to react with all ethylenically unsaturated groups present in the compound.
Voorafgaand aan het harden worden de 20 polyeen- en polythiol-componenten gemengd op een geschikte wijze teneinde een homogeen vloeibaar hardhaar mengsel te vormen.Before curing, the polyene and polythiol components are mixed in an appropriate manner to form a homogeneous liquid hard hair mixture.
Zo kunnen de polyeen- en polythiol-reagentia worden gemengd zon- , der dat het nodig is een oplosmiddel.te gebruiken bij kamertemperatuur of iets verhoogde temperatuur opwaarts tot onge-25 veer 40°C wanneer een van de componenten een vaste stof is of, desgewenst kunnen de reagentia worden opgelost in een geschikt oplosmiddel en daarna kan het oplosmiddel worden verwijderd door geschikte middelen zoals verdamping.For example, the polyene and polythiol reagents can be mixed without the need to use a solvent at room temperature or slightly elevated temperature up to about 40 ° C when one of the components is a solid or, if desired, the reagents can be dissolved in a suitable solvent and then the solvent can be removed by suitable means such as evaporation.
De materialen van de onderhavige uitvin- i 30 ding kunnen desgewenst toevoegsels zoals antioxydantia, kleurstoffen, inhibitoren, vulstoffen, pigmenten, antistatisohe middelen, vlamvertragende middelen, verdikkingsmiddelen, thixo-trope middelen, oppervlakte-actieve middelen, visocistatsmodi-ficeermiddelen, aanlengende oliën, weekmaker, kleverigmakers 35 en dergelijke omvatten binnen het kader van de uitvinding. Zulke toevoegsels worden gewoonlijk voorgemengd met de ethenisch onver- 8104346 9 - 9 - zadigde verbinding voorafgaand aan of tijdens het compounderen. Bruikbare vulstoffen omvatten natuurlijke en synthetische har- ! i | sen, glasvezels, zaagmeel, klei, siliciumdioxyde, aluminium- j oxyde, carbonaten, oxyden, hydroxyden, silicaten, glasvlokken, 5 boraten, fosfaten, diatomeeënaarde, talk, kaolien, bariumsulfaat, calciumsulfaat, calciumcarbonaat, antimoonoxyde en dergelijke.The materials of the present invention may optionally include additives such as antioxidants, dyes, inhibitors, fillers, pigments, antistatic agents, flame retardants, thickeners, thixotropic agents, surfactants, viscosity modifiers, additive oils, plasticizers , tackifiers 35 and the like include within the scope of the invention. Such additives are usually premixed with the ethylenically unsaturated compound prior to or during compounding. Useful fillers include natural and synthetic resins. i | glass fibers, sawdust, clay, silicon dioxide, alumina, carbonates, oxides, hydroxides, silicates, glass flakes, borates, phosphates, diatomaceous earth, talc, kaolin, barium sulfate, calcium sulfate, calcium carbonate, antimony oxide and the like.
i ji j
De voornoemde toevoegsels kunnen aanwezig zijn in hoeveelheden opwaarts tot 500 delen of meer per 100 delen van de ethenisch onverzadigde verbinding, naar gewicht, ; 10 en bij voorkeur ongeveer 0,005 tot ongeveer 300 delen op dezelfde basis.The aforementioned additives may be present in amounts up to 500 parts or more per 100 parts of the ethylenically unsaturated compound, by weight; 10 and preferably about 0.005 to about 300 parts on the same basis.
Verder worden conventionele UV-stabili-seermiddelen en antioxydantia, zoals hydrochinon, tert-butyl-i hydrochinon, tert-butylcatechol, p-benzochinon, 2,5-difenyl- 15 benzochinon, 2,6-di-tert-butyl-p-cresol, gesubstitueerde acrylonitrilen, zoals ethyl-2-cyaan-2,3-difenylacrylaat, 2-ethylhexyl-2-cyaan-3,3-difenylacrylaat, enz. aan het systeem toegevoegd. 'Furthermore, conventional UV stabilizers and antioxidants, such as hydroquinone, tert-butyl hydroquinone, tert-butyl catechol, p-benzoquinone, 2,5-diphenyl-benzoquinone, 2,6-di-tert-butyl-p- cresol, substituted acrylonitriles such as ethyl 2-cyano-2,3-diphenyl acrylate, 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, etc. are added to the system. '
Een type straling dat hier bruikbaar is 20 voor de harding is ultraviolet licht en andere vormen van acti-nische straling welke normaliter worden aangetroffen in straling die wordt uitgezonden door de zon of door kunstmatige bron- ! nen, zoals zonnelampen van het type RS, koolstofbooglampen, i xenonbooglampen, kwikdamplampen, wolfraamhalogenidelampen en j 25 dergelijke. Ultraviolette straling kan het meest doeltreffend worden gebruikt indien het fotohardbare materiaal een geschikte foto-initiator bevat. Hardingsperioden kunnen worden ingesteld op zeer kort en derhalve commercieel economisch door de juiste keuze van de ultravioletbron, de foto-initiator en de concen-30 tratie daarvan, het organische peroxyde of de azoverbinding en de concentratie daarvan, de temperatuur en het molecuulgewicht en de reactieve groep functionaliteit van de ethenisch onverzadigde verbinding. Hardingsperioden van ongeveer 1 tot 80 seconden duur zijn mogelijk, in het bijzonder in foelie- en deklaag-35 toepassingen.One type of radiation useful here for curing is ultraviolet light and other forms of active radiation normally found in radiation emitted from the sun or from artificial source. such as RS type solar lamps, carbon arc lamps, xenon arc lamps, mercury vapor lamps, tungsten halide lamps and the like. Ultraviolet radiation can be used most effectively if the photo-curable material contains a suitable photo-initiator. Curing periods can be set to very short and therefore commercially economical by the proper selection of the ultraviolet source, the photoinitiator and its concentration, the organic peroxide or azo compound and its concentration, temperature and molecular weight and reactive group functionality of the ethylenically unsaturated compound. Curing periods of from about 1 to 80 seconds are possible, especially in film and coating applications.
Wanneer UV-straling wordt gebruikt wordt 8104346 - 10 - ..................................... · . . 2 gewoonlijk een intensiteit van 0,004 tot 60,0 W per cm in het gebied van 200 tot 400 nm gebruikt.When UV radiation is used, 8104346 - 10 - ..................................... ·. . 2 usually uses an intensity of 0.004 to 60.0 W per cm in the range of 200 to 400 nm.
| i| i
Bij het in de praktijk brengen van de onderhavige uitvinding wordt het UV-hardbare materiaal in wille-5 keurige volgorde gemengd en aangebracht op het substraat door diverse conventionele middelen, zoals sproeien, aanbrengen met j een rol of dompelen. Na aanbrenging wordt het materiaal bloot gesteld aan UV-straling gedurende een korte tijd, bijvoorbeeld ongeveer 1 seconde tot 10 minuten.In practicing the present invention, the UV curable material is mixed in any order and applied to the substrate by various conventional means, such as spraying, roller application, or dipping. After application, the material is exposed to UV radiation for a short time, for example about 1 second to 10 minutes.
10 De volgende voorbeelden zullen de onder havige uitvinding toelichten, maar uitdrukkelijk niet beperken. Tenzij anders aangegeven zijn alle delen en percentages naar ge- | wicht.The following examples will illustrate, but expressly not limit, the present invention. Unless otherwise specified, all parts and percentages are by weight weight.
VOOrbeeld IExample I
15 100 dln in de handel verkrijbaar trime- thylolpropaantriacrylaat werd gemengd met 1 dl 2,2-dimethoxy- 2-fenylacetofenon, in de handel gebracht door Ciba-Geigy onder de; merknaam "IRGACURE"-651 in een aluminium weegschaal. Het mengsel werd blootgesteld aan UV-licht uit een kwiklamp van matige druk; i 20 Ascor Addalux Model 1415-42, geplaatst op 61 cm vanaf het mengsel. Een totale harding door het gehele ongeveer 2 mm dikke mengsel werd verkregen in 9 seconden.100 parts of commercially available trimethylolpropane triacrylate was mixed with 1 part of 2,2-dimethoxy-2-phenylacetophenone, sold by Ciba-Geigy under the; brand name "IRGACURE" -651 in an aluminum scale. The mixture was exposed to UV light from a medium pressure mercury lamp; 20 Ascor Addalux Model 1415-42 placed 61 cm from the mixture. Total curing through the entire about 2 mm thick mixture was obtained in 9 seconds.
Vóorbéeld IIExample II
i 100 dln in de handel verkrijgbaar tri- 25 methylolpropaantriacrylaat werd gemengd met 0,5 dln benzoylper-oxyde in een aluminium weegschaal. Het mengsel werd blootgesteld als in voorbeeld I aan UV-straling. Doorharding van het 2 mm dikke mengsel werd verkregen in 66 seconden.100 parts of commercially available trimethylol propane triacrylate was mixed with 0.5 parts of benzoyl peroxide in an aluminum scale. The mixture was exposed to UV radiation as in Example I. Curing of the 2 mm thick mixture was obtained in 66 seconds.
Voorbeeld IIIExample III
30 100 dln trimethylolpropaantriacrylaat werd gemengd met 1 dl ,,IRGACURE"-651 en 0,5 dln benzoylperoxyde in een aluminium weegschaal. Na blootstelling aan UV-straling als in voorbeeld I werd doorharding van het 2 mm dikke mengsel verkregen in 2 seconden.100 parts of trimethylolpropane triacrylate was mixed with 1 part of "IRGACURE" -651 and 0.5 parts of benzoyl peroxide in an aluminum scale After exposure to UV radiation as in Example 1, the 2 mm thick mixture was cured in 2 seconds.
35 Voorbeeld IVExample IV
.100 dln in de handel verkrijgbaar tri- 8104346 - η - methylolpropaantriacrylaat werd gemengd met 1 dl "IRGACURE"-651 : en 5 dln pentaerythritoltetrakis-3-mercaptopropionaat, in de handel verkrijgbaar bij Cincinnati Milacron onder de merknaam j "Q-43" in een aluminium weegschaal. Het mengsel werd blootge-5 steld aan UV-licht uit een kwiklamp van matige druk Ascor100 parts of commercially available tri-8104346-η-methylolpropane triacrylate was mixed with 1 part of "IRGACURE" -651: and 5 parts of pentaerythritoltetrakis-3-mercaptopropionate, commercially available from Cincinnati Milacron under the trade mark j "Q-43" in an aluminum scale. The mixture was exposed to UV light from a medium pressure Ascor mercury lamp
Addalux Model 1415-42 op een afstand van 61 cm van het mengsel. : Doorharding werd verkregen in 7 seconden.Addalux Model 1415-42 at a distance of 61 cm from the mixture. : Curing was obtained in 7 seconds.
Voorbeeld VExample V
100 dln in de handel verkrijgbaar tri-10 methylolpropaantriacrylaat werd gemengd met 0,5 dln benzoylper- : oxyde en 5 dln "Q-43". Na belichting als in voorbeeld IV hardde i het mengsel helder door in 18 seconden. I100 parts of commercially available tri-10 methylol propane triacrylate was mixed with 0.5 parts of benzoyl peroxide and 5 parts of "Q-43". After exposure as in Example IV, the mixture hardened clear in 18 seconds. I
Voorbeeld VIExample VI
100 dln in de handel verkrijgbaar 15 trimethylolpropaantriacrylaat werd gemengd in een aluminium ! weegschaal met 1 dl "IRGACURE"-651, 5 dln "Q-43" en 0,5 dln benzoylperoxyde. Na belichting als in voorbeeld IV werd doorharding verkregen in 1,5 seconden.100 parts of commercially available trimethylolpropane triacrylate was mixed in an aluminum! scale with 1 part "IRGACURE" -651, 5 parts "Q-43" and 0.5 parts benzoyl peroxide. After exposure as in Example IV, curing was achieved in 1.5 seconds.
Als getoond in tabel A werd trimethylol-; 20 propaantriacrylaat met of zonder een polythiol gemengd met het- j zij foto-initiator hetzij een synergistisch middel hetzij beide j in een aluminium weegschaal. De diverse mengsels werden alle blootgesteld aan UV-licht op een afstand van 61 cm van een kwiklamp van matige druk (Ascor Addalux Model 1415-42). De 25 diverse combinaties en de UV-belichtingstijden worden getoond in tabel A.As shown in Table A, trimethylol; Propane triacrylate with or without a polythiol mixed with either photoinitiator either a synergist or both in an aluminum scale. The various mixtures were all exposed to UV light at a distance of 61 cm from a medium pressure mercury lamp (Ascor Addalux Model 1415-42). The 25 various combinations and the UV exposure times are shown in Table A.
30 8104346 - 12 -30 8104346 - 12 -
Synergistisch effect met gemengde foto-initiatoren en synergistische middelen in acrylaat- en thioacrylaat- |Synergistic effect with mixed photoinitiators and synergists in acrylate and thioacrylate
samenstellingen._ Icompositions. I
Tabel ATable A
5 Vb. No. Samenstelling Bloot- Opmer- stellings- kingen tijd aan UV (sec) (a's VII TMOP-TAv ’!\ % Irgacure. 9 Harding 10 651 VIII w/0,5 % benzoylperoxyde 2 Harding en exotherm (c) IX w/0,1 % benzoylperoxyde 3 Harding en exotherm 15 X w/0,01 % benzoylperoxyde 7 Harding XI TM0P-TA/0,5% benzoyl- 66 Harding en peroxyde exotherm XII TMOP-TA/1% Irgacure 651/ 7 Harding 20 5% Q-43 (d) XIII w/0,5% benzoylperoxyde 1,5 Harding en exotherm ; XIV w/0,1% benzopylperoxyde 1,5 Harding en exotherm 25 XV w/0,01% benzoylperoxyde 5 Harding XVI w/0,005% benzoylperoxyde 5 Harding XVII TMOP-TA/0,5% benzoyl- 18 Harding en peroxyde/5% Q-43 exotherm 30 XVIII TM0P-TA/1% benzofenon/ 42 Harding 5% Q-43 XIX w/0,5% benzoylperoxyde 14 Harding en exotherm XX TM0P-TA/0,5% benzoyl- 18 Harding en 35 peroxyde/5% Q-43 exotherm XXI TMOP-TA/1% Irgacure 651 9 Harding5 Ex. No. Composition Exposure Notes Time to UV (sec) (a's VII TMOP-TAv '! \% Irgacure. 9 Cure 10 651 VIII w / 0.5% Benzoyl Peroxide 2 Cure and Exotherm (c) IX w / 0, 1% Benzoyl Peroxide 3 Curing and Exotherm 15 X w / 0.01% Benzoyl Peroxide 7 Curing XI TM0P-TA / 0.5% Benzoyl- 66 Curing and Peroxide Exotherm XII TMOP-TA / 1% Irgacure 651/7 Curing 20 5% Q -43 (d) XIII w / 0.5% Benzoyl Peroxide 1.5 Curing and Exotherm; XIV w / 0.1% Benzopyl Peroxide 1.5 Curing and Exotherm 25 XV w / 0.01% Benzoyl Peroxide 5 Curing XVI w / 0.005% Benzoyl Peroxide 5 Curing XVII TMOP-TA / 0.5% Benzoyl- 18 Curing and Peroxide / 5% Q-43 Exotherm 30 XVIII TM0P-TA / 1% Benzophenone / 42 Curing 5% Q-43 XIX w / 0.5% Benzoyl Peroxide 14 Curing and exotherm XX TM0P-TA / 0.5% benzoyl- 18 Curing and 35 peroxide / 5% Q-43 exotherm XXI TMOP-TA / 1% Irgacure 651 9 Curing
CeV .CeV.
XXII w/1% CADOX-TDPv ’ 2,5 Harding en exo therm 40 XXIII w/0,2% CADOX-TDP 3 Harding en exotherm XXIV TMOP-TA/1% CADOX-TDP 13 Harding en exotherm 8104346 ψ - 13 -XXII w / 1% CADOX-TDPv '2.5 Curing and exo therm 40 XXIII w / 0.2% CADOX-TDP 3 Curing and exotherm XXIV TMOP-TA / 1% CADOX-TDP 13 Curing and exotherm 8104346 13 - 13 -
Vervolg van tabel A IContinued from Table A I.
Vb. No. Samenstelling Bloot- Opmerkin- stellings- gen tijd aan 5 __ UV (sec)_: XXV TMOP-TA/1% Irgacure 651 9 Harding XXVI w/0,5% t-butylperben- 3 Harding en zoaat Exotherm XXVII w/0,1% t-butyl- 4 Harding en : 10 perbenzoaat Exotherm XXVIII w/0,01% t-butyl- 7 Harding en perbenzoaat Exotherm XXIX TMOP-TA/0,5% t-butyl- 110 Harding en perbenzoaat Exotherm 15 XXX TMOP-TA/1% Irgacure 651/ 7 Harding 5 % Q-43 XXXI w/0,5% t-butyl- 1,5 Harding en perbenzoaat Exotherm 20 XXXII 2/0,1% t-butyl- 2 Harding en perbenzoaat Exotherm XXXIII w/0,01 % butyl- 5 Harding perbenzoaat XXXIV w/0,005% t-butyl- 5 Harding 25 perbenzoaat XXXV TMOP-TA/0,5 % t-butyl- 38 Harding en perbenzoaat Exotherm XXXVI TMOP-TA/1% benzofenon/ 42 Harding 30 5% Q-43 XXXVII w/0,5% t-butyl- 42 Harding en perbenzoaat Exotherm XXXVIII w/0,1% t-butyl- 27 Harding en perbenzoaat Exotherm 35 XXXIX w/0,01% t-butyl- 31 Harding perbenzoaat XL TMOP-TA/0,5% t-butyl- 38 Harding en perbenzoaat/5% Q-43 Exotherm 8104346 « - 14 - ψEx. No. Composition Exposure Notes time at 5 __ UV (sec) _: XXV TMOP-TA / 1% Irgacure 651 9 Cure XXVI w / 0.5% t-butyl perben- 3 Cure and sweeten Exotherm XXVII w / 0, 1% t-butyl- 4 Curing and: 10 perbenzoate Exotherm XXVIII w / 0.01% t-butyl- 7 Curing and perbenzoate Exotherm XXIX TMOP-TA / 0.5% t-butyl- 110 Curing and perbenzoate Exotherm 15 XXX TMOP -TA / 1% Irgacure 651/7 Curing 5% Q-43 XXXI w / 0.5% t-butyl- 1.5 Curing and perbenzoate Exotherm 20 XXXII 2 / 0.1% t-butyl- 2 Curing and perbenzoate Exotherm XXXIII w / 0.01% butyl-5 Curing perbenzoate XXXIV w / 0.005% t-butyl- 5 Curing 25 perbenzoate XXXV TMOP-TA / 0.5% t-butyl- 38 Curing and perbenzoate Exotherm XXXVI TMOP-TA / 1% benzophenone / 42 Curing 30 5% Q-43 XXXVII w / 0.5% t-butyl- 42 Curing and perbenzoate Exotherm XXXVIII w / 0.1% t-butyl- 27 Curing and perbenzoate Exotherm 35 XXXIX w / 0.01% t-butyl- 31 Curing perbenzoate XL TMOP-TA / 0.5% t-butyl- 38 Curing and perbenzoate / 5% Q-43 Exotherm 8104346 «- 14 - ψ
Vervolg van tabel AContinued from Table A.
Vb.No. Samenstelling Bloot- Opmerkingen stellings-tijd aan 5 _UV (sec) _; XLI TMOP-TA/1% Irgacure 651 9 Harding XLII w/0,5% di-t-butyl- 4,5 Harding en peroxyde Exotherm XLIII w/0,1% di-t-butyl- 7 Harding en 10 peroxyde Exotherm XLIV TMOP-TA/0,5% di-t-butyl- 420 Gedeeltelijke peroxyde harding XLV TMOP-TA/1% Irgacure 651/ 7 Harding 15 5% 0-43 XLVI w/0,5% di-t-butyl- 2 Harding en peroxyde Exotherm XLVII w/0,1% di-t-butyl- 2 Harding en peroxyde Exotherm 20 XLVIII TMOP-TA/0,5% di-t-butyl- 65 Harding en peroxyde/5% Q-43 Exotherm XLIX TMOP-TA/1% Irgacure 651 9 Harding L w/0,5% Lupersol 231^ 2,5 Harding en 25 Exotherm LI w/0,1% Lupersol 231 3,5 Harding enEx No. Composition Exposure Notes exposure time at 5 _UV (sec) _; XLI TMOP-TA / 1% Irgacure 651 9 Curing XLII w / 0.5% di-t-butyl- 4.5 Curing and peroxide Exotherm XLIII w / 0.1% di-t-butyl- 7 Curing and 10 peroxide Exotherm XLIV TMOP-TA / 0.5% di-t-butyl- 420 Partial peroxide cure XLV TMOP-TA / 1% Irgacure 651/7 Cure 15 5% 0-43 XLVI w / 0.5% di-t-butyl- 2 Curing and peroxide Exotherm XLVII w / 0.1% di-t-butyl- 2 Curing and peroxide Exotherm 20 XLVIII TMOP-TA / 0.5% di-t-butyl- 65 Curing and peroxide / 5% Q-43 Exotherm XLIX TMOP-TA / 1% Irgacure 651 9 Curing L w / 0.5% Lupersol 231 ^ 2.5 Curing and 25 Exotherm LI w / 0.1% Lupersol 231 3.5 Curing and
ExothermExothermic
Lil TMOP-TA/0,5% Lupersol 231 196 Harding enLil TMOP-TA / 0.5% Lupersol 231 196 Curing and
Exotherm 30 LUI TMOP-TA/1% Irgacure 651/ 7 Harding 5% Q-43 LIV w/0,5% Lupersol 231 1,4 Harding enExotherm 30 LUI TMOP-TA / 1% Irgacure 651/7 Curing 5% Q-43 LIV w / 0.5% Lupersol 231 1.4 Curing and
Exotherm 35 LV w/0,1% Lupersol 231 1,8 Harding enExotherm 35 LV w / 0.1% Lupersol 231 1.8 Curing and
Exotherm LVI TMOP-TA/0,5% Lupersol 231/ 58 Harding en 5% Q-43 Exotherm 8104346 - 15 -Exotherm LVI TMOP-TA / 0.5% Lupersol 231/58 Curing and 5% Q-43 Exotherm 8104346 - 15 -
Vervolg van tabel AContinued from Table A.
I Vb.No. Samenstelling Bloot- Opmerkingen stellings-tijd aan 5 _UV (sec)__ LVII TMOP-TA/1% benzofenon 240 Gedeeltelijke harding LVIII w/0,5% Lupersol 231 183 Harding enI Ex No. Composition Exposure Notes exposure time at 5 _UV (sec) __ LVII TMOP-TA / 1% benzophenone 240 Partial curing LVIII w / 0.5% Lupersol 231 183 Curing and
Exotherm 10 LIX TMOP-TA/0,5% Lupersol 231 196 Harding enExotherm 10 LIX TMOP-TA / 0.5% Lupersol 231 196 Curing and
Exotherm LX TMOP-TA/1% Irgacure 651 9 Harding LXI w/0,5% t-butyl- 8 Harding en 15 hydroperoxyde Exotherm LXII TMOP-TA/0,5% t-butyl- 300 Enige gelering hydroperoxyde LXIII TMOP-TA/1% Irgacure 651/ 7 Harding 20 5% Q-43 LXIV w/0,5% t-butyl- 5 Harding en hydroperoxyde Exotherm LXV TMOP-TA/0,5% t-butyl- 71 Harding en hydroperoxyde/5% Q-43 Exotherm 25 LXVI TMOP-TA/1% benzofenon/ 42 Harding 5% Q-43 LXVII w/0,5% t-butyl- 28 Harding en hydroperoxyde Exotherm 30 LXVIII 0,1% t-butyl- 35 Harding hydroperoxyde LXIX TMOP-TA/0,5% t-butyl- 71 Harding en hydroperoxyde Exotherm 35 LXX TMOP-TA/1% benzofenon/ 42 Harding 5% Q-43 LXXI w/0,5% Lupersol 231 25 Harding enExotherm LX TMOP-TA / 1% Irgacure 651 9 Curing LXI w / 0.5% t-butyl- 8 Curing and 15 hydroperoxide Exotherm LXII TMOP-TA / 0.5% t-butyl- 300 Single gelling hydroperoxide LXIII TMOP-TA / 1% Irgacure 651/7 Curing 20 5% Q-43 LXIV w / 0.5% t-butyl- 5 Curing and hydroperoxide Exotherm LXV TMOP-TA / 0.5% t-butyl- 71 Curing and hydroperoxide / 5% Q-43 Exotherm 25 LXVI TMOP-TA / 1% Benzophenone / 42 Curing 5% Q-43 LXVII w / 0.5% t-butyl- 28 Curing and Hydroperoxide Exotherm 30 LXVIII 0.1% t-butyl- 35 Curing Hydroperoxide LXIX TMOP-TA / 0.5% t-butyl- 71 Curing and hydroperoxide Exotherm 35 LXX TMOP-TA / 1% Benzophenone / 42 Curing 5% Q-43 LXXI w / 0.5% Lupersol 231 25 Curing and
Exotherm LXXII w/0,1% Lupersol 231 27 Harding en 40 Exotherm LXXIII TMOP-TA/0,5% Lupersol 231/ 58 Harding en 5% Q-43 Exotherm 8104346 - 16 -Exotherm LXXII w / 0.1% Lupersol 231 27 Curing and 40 Exotherm LXXIII TMOP-TA / 0.5% Lupersol 231/58 Curing and 5% Q-43 Exotherm 8104346 - 16 -
Vervolg van tabel AContinued from Table A.
Vb.No. Samenstelling Bloot- Opmerkingen stellings-tijd aanEx No. Composition Exposure Notes on exposure time
5 __UV (sec)_I5 __UV (sec) _I
LXXIV TMOP-TA/1% Irgacure 651 9 Harding LXXV w/0,5% Luazo 79^ 2,5 Harding enLXXIV TMOP-TA / 1% Irgacure 651 9 Curing LXXV w / 0.5% Luazo 79 ^ 2.5 Curing and
Exotherm LXXVI w/0,1% Luazo 79 4 Harding en 10 Exotherm LXXVII TMOP-TA/O,5% Luazo 79 149 Harding enExotherm LXXVI w / 0.1% Luazo 79 4 Curing and 10 Exotherm LXXVII TMOP-TA / O, 5% Luazo 79 149 Curing and
Exotherm LXXVIII TMOP-TA/1% Irgacure 651/ 7 Harding 5% Q-43 15 LXXIX w/0,5% Luazo 79 1,5 Harding enExotherm LXXVIII TMOP-TA / 1% Irgacure 651/7 Curing 5% Q-43 15 LXXIX w / 0.5% Luazo 79 1.5 Curing and
Exotherm LXXX w/0,1% Luazo 79 2 Harding enExotherm LXXX w / 0.1% Luazo 79 2 Curing and
Exotherm LXXXI TMOP-TA/O,5% Luazo 79/ 33 Harding en 20 5% Q-43 Exotherm LXXXII TMOP-TA/1% benzofenon 240 Gedeeltelijke harding LXXXIII w/0,5% Luazo 79 74 Harding enExotherm LXXXI TMOP-TA / O, 5% Luazo 79/33 Curing and 20 5% Q-43 Exotherm LXXXII TMOP-TA / 1% Benzophenone 240 Partial Curing LXXXIII w / 0.5% Luazo 79 74 Curing and
Exotherm 25 LXXXIV TMOP-TA/O,5% Luazo 79 149 Harding enExotherm 25 LXXXIV TMOP-TA / O, 5% Luazo 79 149 Curing and
Exotherm LXXXV TMOP-TA/1% benzofenon/ 42 Harding 5% Q-43 30 LXXXVI w/0,5% Luazo 79 16 Harding enExotherm LXXXV TMOP-TA / 1% Benzophenone / 42 Curing 5% Q-43 30 LXXXVI w / 0.5% Luazo 79 16 Curing and
Exotherm LXXXVII w/0,1% Luazo 79 26 Harding enExotherm LXXXVII w / 0.1% Luazo 79 26 Curing and
Exotherm LXXXVIII TMOP-TA/O,5% Luazo 79/ 33 Harding en 35 5% Q-43 Exotherm LXXXIX TMOP-TA/1% Irgacure 651 9 Harding XC w/0,5% VAZO-64^ 2 Harding enExotherm LXXXVIII TMOP-TA / O, 5% Luazo 79/33 Curing and 35 5% Q-43 Exotherm LXXXIX TMOP-TA / 1% Irgacure 651 9 Curing XC w / 0.5% VAZO-64 ^ 2 Curing and
Exotherm 40 XCI TMOP-TA/0,5% VAZO-64 99 Harding enExotherm 40 XCI TMOP-TA / 0.5% VAZO-64 99 Curing and
Exotherm 8104346 \ - 17 -Exotherm 8104346 \ - 17 -
Vervolg van tabel AContinued from Table A.
Vb. No. Samenstelling Bloot- Opmerkingen stellings- | tijd aan jEx. No. Composition Exposure Comments statement | time to j
| 5 ______UV (sec)_ I| 5 ______UV (sec) _ I
XCII 75% TMOP-TA/25% TAIC(l)/ 12 Harding 1% Irgacure 651 XCIII w/5% Q-43 6,5 Harding ' XCIV w/0,5% VAZO-64 3 Harding en 10 Exotherm XCV w/0,5% VAZO-64/5% Q-43 2 Harding en jXCII 75% TMOP-TA / 25% TAIC (l) / 12 Curing 1% Irgacure 651 XCIII w / 5% Q-43 6.5 Curing 'XCIV w / 0.5% VAZO-64 3 Curing and 10 Exotherm XCV w / 0.5% VAZO-64/5% Q-43 2 Curing and j
Exotherm i XCVI 50% TMOP-TA/5’% TAIC/ 25 Harding 15 1 % Irgacure 651 XCVII w/5% Q-43 10 Harding XCVIII w/0,5% VAZO-64 8 Harding | XCIX w/0,5% VAZO-64/5% 0-43 6,5 Harding 20 Voetnoten i (a) TMOP-TA = trimethylolpropaan-triacrylaat (b) Irgacure 651 = 2,2-dimethoxy-2-fenylacetofenon, in de handel gebracht door Ciba-Geigy.Exotherm i XCVI 50% TMOP-TA / 5% TAIC / 25 Curing 15 1% Irgacure 651 XCVII w / 5% Q-43 10 Curing XCVIII w / 0.5% VAZO-64 8 Curing | XCIX w / 0.5% VAZO-64/5% 0-43 6.5 Curing 20 Footnotes i (a) TMOP-TA = trimethylolpropane triacrylate (b) Irgacure 651 = 2,2-dimethoxy-2-phenylacetophenone, in marketed by Ciba-Geigy.
(c) Materiaal begon normaal aan het oppervlak te harden, maar 25 begon vervolgens heftig warmte te ontwikkelen op welk punt het licht werd uigeschakeld: het materiaal ging verder met warmte ontwikkelen en harden.(c) Material normally started to harden on the surface, but then began to violently develop heat at which point the light was turned off: the material continued to heat and cure.
(d) Q-43 = pentaërythritol-tetrakis-(B-mercapto-propionaat), in de handel gebracht door Cincinnati Milacron.(d) Q-43 = pentaerythritol tetrakis- (B-mercapto-propionate) sold by Cincinnati Milacron.
30 (e) CADOX-TDP = 50% 2,4-dichloorbenzoylperoxyde in dibutyl- ftalaat, in de handel gebracht door Noury Chemical Co.(E) CADOX-TDP = 50% 2,4-dichlorobenzoyl peroxide in dibutyl phthalate, sold by Noury Chemical Co.
(f) Lupersol 231 - 1,1—bis(t-butylperoxyde-3,3,5-trimethyl-cyclohexaan, in de handel gebracht door Pennwalt Corp.(f) Lupersol 231-1,1-bis (t-butylperoxide-3,3,5-trimethyl-cyclohexane, marketed by Pennwalt Corp.
(g) Luazo-79 = 2-t-butylazo-2-cyanopropaan, in de handel 35 gebracht door Pennwalt Corp.(g) Luazo-79 = 2-t-butylazo-2-cyanopropane, marketed by Pennwalt Corp.
(h) VAZO-64 = 2,2’-azobis(isobutyronitril), in de handel gebracht door DuPont Company.(h) VAZO-64 = 2,2'-azobis (isobutyronitrile) marketed by DuPont Company.
(i) TAIC = Triallyl-isocyanuraat.(i) TAIC = Triallyl isocyanurate.
8104346 * - 18 - i Zoals duidelijk blijkt uit de resulta ten in tabel A treedt een synergistiscb effect van een verminderde hardingstijd op wanneer de niet-stikstofhoudende foto-initiator wordt gebruikt in combinatie met hetzij een organisch 5 peroxyde hetzij een azoverbinding, in vergelijking met elk lid van de combinatie op zichzelf.8104346 * - 18 - i As is clear from the results in Table A, a synergistic effect of a reduced cure time occurs when the non-nitrogenous photoinitiator is used in combination with either an organic peroxide or an azo compound, as compared to each member of the combination alone.
i 81043468104346
Claims (11)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21903480A | 1980-12-22 | 1980-12-22 | |
| US21903480 | 1980-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8104346A true NL8104346A (en) | 1982-07-16 |
Family
ID=22817548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8104346A NL8104346A (en) | 1980-12-22 | 1981-09-22 | PHOTHARDISABLE MATERIALS AND METHOD FOR THE MANUFACTURE OF HARDENED PRODUCTS THEREOF. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS57125205A (en) |
| BR (1) | BR8105837A (en) |
| DE (1) | DE3137358A1 (en) |
| FR (1) | FR2496672A1 (en) |
| GB (1) | GB2089818B (en) |
| IT (1) | IT1139492B (en) |
| NL (1) | NL8104346A (en) |
| SE (1) | SE8107242L (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2165255A (en) * | 1984-10-03 | 1986-04-09 | Peter Joseph Carr | Production of ear mouldings and other moulded articles of acrylic polymers |
| US5017406A (en) * | 1988-12-08 | 1991-05-21 | Dow Corning Corporation | UV curable compositions cured with polysilane and peroxide initiators |
| US5565499A (en) * | 1993-03-24 | 1996-10-15 | Loctite Corporation | Filament-winding compositions for fiber/resin composites |
| JP7081486B2 (en) * | 2016-08-22 | 2022-06-07 | 株式会社大阪ソーダ | Photocurable resin compositions, inks and paints |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB817343A (en) * | 1956-02-07 | 1959-07-29 | Swedlow Plastics Company | Improvements in or relating to process for preparing continuous plastic sheets |
| DE2118685C3 (en) * | 1971-04-17 | 1980-07-17 | Roehm Gmbh, 6100 Darmstadt | Process for polymerizing unsaturated compounds in a thick layer |
| JPS6027686B2 (en) * | 1976-02-17 | 1985-07-01 | 東洋インキ製造株式会社 | Protective coating formation method |
| US4222835A (en) * | 1978-05-25 | 1980-09-16 | Westinghouse Electric Corp. | In depth curing of resins induced by UV radiation |
-
1981
- 1981-09-14 BR BR8105837A patent/BR8105837A/en unknown
- 1981-09-19 DE DE19813137358 patent/DE3137358A1/en not_active Withdrawn
- 1981-09-22 NL NL8104346A patent/NL8104346A/en unknown
- 1981-09-25 IT IT24166/81A patent/IT1139492B/en active
- 1981-12-03 SE SE8107242A patent/SE8107242L/en not_active Application Discontinuation
- 1981-12-04 GB GB8136643A patent/GB2089818B/en not_active Expired
- 1981-12-11 JP JP56198742A patent/JPS57125205A/en active Pending
- 1981-12-21 FR FR8123843A patent/FR2496672A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BR8105837A (en) | 1982-09-08 |
| JPS57125205A (en) | 1982-08-04 |
| GB2089818B (en) | 1984-07-18 |
| IT8124166A0 (en) | 1981-09-25 |
| FR2496672A1 (en) | 1982-06-25 |
| DE3137358A1 (en) | 1982-08-19 |
| SE8107242L (en) | 1982-06-23 |
| GB2089818A (en) | 1982-06-30 |
| IT1139492B (en) | 1986-09-24 |
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