CA1066547A - Composes pigmentes photopolymerisables stabilises par des thiocarbamates, retardant la gelification - Google Patents

Composes pigmentes photopolymerisables stabilises par des thiocarbamates, retardant la gelification

Info

Publication number: CA1066547A
Authority: CA; Canada
Prior art keywords: composition; acid; carbon atoms; beta; ethylenically unsaturated
Prior art date: 1975-05-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA239,596A

Other languages

English (en)

Other versions

CA239596S (en

Inventor

Thor Jondahl

George Pasternack

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Continental Can Co Inc

Original Assignee

Continental Can Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-05-29

Filing date

1975-11-10

Publication date

1979-11-20

1975-05-29 Priority claimed from US05/582,000 external-priority patent/US3932346A/en

1975-11-10 Application filed by Continental Can Co Inc filed Critical Continental Can Co Inc

1979-11-20 Application granted granted Critical

1979-11-20 Publication of CA1066547A publication Critical patent/CA1066547A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 11
230000002028 premature Effects 0.000 title abstract description 3
238000001879 gelation Methods 0.000 title description 3
150000003558 thiocarbamic acid derivatives Chemical class 0.000 title description 3
239000000203 mixture Substances 0.000 claims abstract description 44
229910052751 metal Inorganic materials 0.000 claims abstract description 16
239000002184 metal Substances 0.000 claims abstract description 16
150000002148 esters Chemical class 0.000 claims abstract description 14
-1 thiocarbamate compound Chemical class 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
150000001768 cations Chemical class 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
230000000087 stabilizing effect Effects 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 18
239000000049 pigment Substances 0.000 claims description 14
229920000647 polyepoxide Polymers 0.000 claims description 11
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
229920000728 polyester Polymers 0.000 claims description 6
BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 claims description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
150000005846 sugar alcohols Polymers 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 3
WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical group OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 claims description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 3
150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
239000002202 Polyethylene glycol Substances 0.000 claims 1
IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 0.000 claims 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
PVFZKRMYBKEXBN-UHFFFAOYSA-N piperidine;piperidine-1-carbodithioic acid Chemical compound C1CCNCC1.SC(=S)N1CCCCC1 PVFZKRMYBKEXBN-UHFFFAOYSA-N 0.000 claims 1
229920001223 polyethylene glycol Polymers 0.000 claims 1
239000000976 ink Substances 0.000 abstract description 29
238000000576 coating method Methods 0.000 abstract description 11
108010010803 Gelatin Proteins 0.000 abstract 1
229920000159 gelatin Polymers 0.000 abstract 1
239000008273 gelatin Substances 0.000 abstract 1
235000019322 gelatine Nutrition 0.000 abstract 1
235000011852 gelatine desserts Nutrition 0.000 abstract 1
239000000499 gel Substances 0.000 description 34
239000003981 vehicle Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 7
229920006305 unsaturated polyester Polymers 0.000 description 6
230000005855 radiation Effects 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 4
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
SZRLKIKBPASKQH-UHFFFAOYSA-M dibutyldithiocarbamate Chemical compound CCCCN(C([S-])=S)CCCC SZRLKIKBPASKQH-UHFFFAOYSA-M 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
239000000758 substrate Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
125000004386 diacrylate group Chemical group 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
235000013361 beverage Nutrition 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
239000010408 film Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
238000013112 stability test Methods 0.000 description 2
239000010959 steel Substances 0.000 description 2
XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
SYQQWGGBOQFINV-FBWHQHKGSA-N 4-[2-[(2s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-2-yl]ethoxy]-4-oxobutanoic acid Chemical compound C1CC2=CC(=O)[C@H](CCOC(=O)CCC(O)=O)C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 SYQQWGGBOQFINV-FBWHQHKGSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 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
239000004593 Epoxy Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
AKWFCZBRUMZPBI-UHFFFAOYSA-J N,N-diethylcarbamodithioate zirconium(4+) Chemical compound C(C)N(C([S-])=S)CC.[Zr+4].C(C)N(C([S-])=S)CC.C(C)N(C([S-])=S)CC.C(C)N(C([S-])=S)CC AKWFCZBRUMZPBI-UHFFFAOYSA-J 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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 1
GQPVFBDWIUVLHG-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)COC(=O)C(C)=C GQPVFBDWIUVLHG-UHFFFAOYSA-N 0.000 description 1
JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
HSZUHSXXAOWGQY-UHFFFAOYSA-N [2-methyl-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)COC(=O)C=C HSZUHSXXAOWGQY-UHFFFAOYSA-N 0.000 description 1
KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
HYSMCXPFAFAYNG-UHFFFAOYSA-N azanium;n,n-dipropylcarbamodithioate Chemical compound [NH4+].CCCN(C([S-])=S)CCC HYSMCXPFAFAYNG-UHFFFAOYSA-N 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
CEULSLLDFRYXBM-UHFFFAOYSA-L calcium;n,n-dihexylcarbamodithioate Chemical compound [Ca+2].CCCCCCN(C([S-])=S)CCCCCC.CCCCCCN(C([S-])=S)CCCCCC CEULSLLDFRYXBM-UHFFFAOYSA-L 0.000 description 1
DOONUBWPNCVMQW-UHFFFAOYSA-N carbamothioylsulfanyl n-tetradecylcarbamodithioate Chemical compound CCCCCCCCCCCCCCNC(=S)SSC(N)=S DOONUBWPNCVMQW-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
BDCVQFMEJUHADG-UHFFFAOYSA-L cobalt(2+);n,n-dibutylcarbamodithioate Chemical compound [Co+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BDCVQFMEJUHADG-UHFFFAOYSA-L 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
229940116901 diethyldithiocarbamate Drugs 0.000 description 1
LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001056 green pigment Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000007788 liquid Substances 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
235000012054 meals Nutrition 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
238000000034 method Methods 0.000 description 1
RTCUWSIVUIEKSS-UHFFFAOYSA-L n,n-dipropylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CCCN(C([S-])=S)CCC.CCCN(C([S-])=S)CCC RTCUWSIVUIEKSS-UHFFFAOYSA-L 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
ALOYJTJXDYAPIE-UHFFFAOYSA-M potassium;n,n-dihexylcarbamodithioate Chemical compound [K+].CCCCCCN(C([S-])=S)CCCCCC ALOYJTJXDYAPIE-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HUMLQUKVJARKRN-UHFFFAOYSA-M sodium;n,n-dibutylcarbamodithioate Chemical compound [Na+].CCCCN(C([S-])=S)CCCC HUMLQUKVJARKRN-UHFFFAOYSA-M 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
229940113165 trimethylolpropane Drugs 0.000 description 1
VSWBCXJHSLMWFY-UHFFFAOYSA-L zinc;n,n-dihexylcarbamodithioate Chemical compound [Zn+2].CCCCCCN(C([S-])=S)CCCCCC.CCCCCCN(C([S-])=S)CCCCCC VSWBCXJHSLMWFY-UHFFFAOYSA-L 0.000 description 1
SZNCKQHFYDCMLZ-UHFFFAOYSA-L zinc;propan-2-yloxymethanedithioate Chemical compound [Zn+2].CC(C)OC([S-])=S.CC(C)OC([S-])=S SZNCKQHFYDCMLZ-UHFFFAOYSA-L 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1

Landscapes

Inks, Pencil-Leads, Or Crayons (AREA)

CA239,596A 1975-05-29 1975-11-10 Composes pigmentes photopolymerisables stabilises par des thiocarbamates, retardant la gelification Expired CA1066547A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/582,000 US3932346A (en)	1974-03-18	1975-05-29	Pigmented photopolymerizable compounds stabilized against premature gelation with thiocarbamates

Publications (1)

Publication Number	Publication Date
CA1066547A true CA1066547A (fr)	1979-11-20

Family

ID=24327437

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA239,596A Expired CA1066547A (fr)	1975-05-29	1975-11-10	Composes pigmentes photopolymerisables stabilises par des thiocarbamates, retardant la gelification

Country Status (1)

Country	Link
CA (1)	CA1066547A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119614888A (zh) *	2025-02-17	2025-03-14	山东黄金矿业科技有限公司选冶实验室分公司	一种降低黄金冶炼贵液中汞含量的方法

1975
- 1975-11-10 CA CA239,596A patent/CA1066547A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119614888A (zh) *	2025-02-17	2025-03-14	山东黄金矿业科技有限公司选冶实验室分公司	一种降低黄金冶炼贵液中汞含量的方法
CN119614888B (zh) *	2025-02-17	2025-04-25	山东黄金矿业科技有限公司选冶实验室分公司	一种降低黄金冶炼贵液中汞含量的方法

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US3903322A (en)	1975-09-02	Photopolymerizable ethylenically unsaturated compounds photoinitiated with benzoyl derivatives of diphenyl sulfide and an organic amine compound
US3956235A (en)	1976-05-11	Photopolymerizable compounds stabilized against premature gelation with copper compounds and thiocarbamates
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US4428807A (en)	1984-01-31	Composition containing polymerizable entities having oxirane groups and terminal olefinic unsaturation in combination with free-radical and cationic photopolymerizations means
US3926641A (en)	1975-12-16	Photopolymerizable compositions comprising polycarboxysubstituted benzophenone reaction products
US4004998A (en)	1977-01-25	Photopolymerizable compounds and compositions comprising the product of the reaction of a hydroxy-containing ester and a monocarboxy-substituted benzophenone
US4022674A (en)	1977-05-10	Photopolymerizable compounds and compositions comprising the product of the reaction of a monomeric ester and a polycarboxy-substituted benzophenone
US4447520A (en)	1984-05-08	Acylphosphine oxides and their use
US5889076A (en)	1999-03-30	Radiation curable rheology modifiers
EP0280222A2 (fr)	1988-08-31	Produits d'addition à partir d'acrylates et d'amines et leur utilisation dans des masses durcissables par rayons
US4253918A (en)	1981-03-03	Air-drying coating compositions
US4038084A (en)	1977-07-26	Photo-setting composition
DE2534012A1 (de)	1977-02-17	Haertbare ueberzugsmittel
CA1057997A (fr)	1979-07-10	Produit radiodurcissable contenant un prepolymere comportant un ester de type hydroxyalkyle et un anhydride halogene
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US4085018A (en)	1978-04-18	Photocurable resin compositions
US3932346A (en)	1976-01-13	Pigmented photopolymerizable compounds stabilized against premature gelation with thiocarbamates
US4221892A (en)	1980-09-09	Photocurable partially esterified polyepoxides
EP0037152B1 (fr)	1984-08-15	Système initiateur pour compositions durcissables par radiations, compositions durcissables par radiations contenant un tel système initiateur, procédé pour durcir lesdites compositions et produits recouverts par celle-ci
CA1066547A (fr)	1979-11-20	Composes pigmentes photopolymerisables stabilises par des thiocarbamates, retardant la gelification
US5212271A (en)	1993-05-18	Process for obtaining textured coatings from photo-curable urea-containing compositions
US4179478A (en)	1979-12-18	Process for the production of binders
US3926640A (en)	1975-12-16	Photopolymerizable compositions comprising benzophenone reaction products
GB1590414A (en)	1981-06-03	Radiation curable coating compositions