JPH01115918A - Coating composition curable with actinic energy radiation - Google Patents
Coating composition curable with actinic energy radiationInfo
- Publication number
- JPH01115918A JPH01115918A JP27335987A JP27335987A JPH01115918A JP H01115918 A JPH01115918 A JP H01115918A JP 27335987 A JP27335987 A JP 27335987A JP 27335987 A JP27335987 A JP 27335987A JP H01115918 A JPH01115918 A JP H01115918A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acrylate
- meth
- parts
- coating composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000008199 coating composition Substances 0.000 title claims description 17
- 230000005855 radiation Effects 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 229920000180 alkyd Polymers 0.000 claims abstract description 6
- DXPLEDYRQHTBDJ-CCEZHUSRSA-N 2-[(E)-pentadec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O DXPLEDYRQHTBDJ-CCEZHUSRSA-N 0.000 claims abstract description 5
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 5
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 13
- 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 abstract description 4
- LNBZWBNYIKPDFQ-UHFFFAOYSA-N [4,4-bis(diethylamino)cyclohexa-1,5-dien-1-yl]-phenylmethanone Chemical compound C1=CC(N(CC)CC)(N(CC)CC)CC=C1C(=O)C1=CC=CC=C1 LNBZWBNYIKPDFQ-UHFFFAOYSA-N 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
- 239000002253 acid Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- -1 pentyl glycol Chemical compound 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 238000007664 blowing Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 3
- BNDWRWFZSMPKQP-UHFFFAOYSA-N 3-pentadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC=CC1CC(=O)OC1=O BNDWRWFZSMPKQP-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229940105990 diglycerin Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-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
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 238000012719 thermal polymerization Methods 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- NIDNOXCRFUCAKQ-RNGGSSJXSA-N (1r,2r,3s,4s)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@@H]2C=C[C@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-RNGGSSJXSA-N 0.000 description 1
- IQVLXQGNLCPZCL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)NCCCCC(NC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O IQVLXQGNLCPZCL-UHFFFAOYSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UMLWXYJZDNNBTD-UHFFFAOYSA-N 2-(dimethylamino)-1-phenylethanone Chemical compound CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical group C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OJVQNVMHJWSOSY-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(O)=O)(C)C2C(O)=O OJVQNVMHJWSOSY-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VNGLVZLEUDIDQH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;2-methyloxirane Chemical compound CC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 VNGLVZLEUDIDQH-UHFFFAOYSA-N 0.000 description 1
- WPSWDCBWMRJJED-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;oxirane Chemical compound C1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WPSWDCBWMRJJED-UHFFFAOYSA-N 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- WDENQIQQYWYTPO-IBGZPJMESA-N acalabrutinib Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C(=O)NC=2N=CC=CC=2)=C2N1C=CN=C2N WDENQIQQYWYTPO-IBGZPJMESA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001336 alkenes 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
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QNSOHXTZPUMONC-UHFFFAOYSA-N benzene pentacarboxylic acid Natural products OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O QNSOHXTZPUMONC-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- KOEVABCENPYWCU-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrachlorophenyl)methanone Chemical compound ClC1=C(Cl)C(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1Cl KOEVABCENPYWCU-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004094 surface-active 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
「発明の目的」
(産業上の利用分野)
本発明は活性エネルギー線硬化性被覆組成物に関するも
のであり、詳しくは紫外線もしくは電子線等の照射によ
り硬化し、しかも、印刷適性等に優れた活性エネルギー
線硬化性被覆組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION Object of the Invention (Field of Industrial Application) The present invention relates to an active energy ray-curable coating composition, and more specifically, it is cured by irradiation with ultraviolet rays or electron beams, and furthermore, The present invention relates to an active energy ray-curable coating composition that has excellent printability and the like.
(従来の技術)
近年、活性エネルギー線による硬化性被覆組成物の研究
はさかんにおこなわれており、その中でも印刷インキ、
クリヤーワニス、塗料、接着剤、フォトレジスト等の分
野では実用化が進められている。これらはラジカル重合
性を有するラジカル重合性モノマーおよびプレポリマー
と、必要に応じてラジカル重合開始剤。(Prior Art) In recent years, research on coating compositions curable with active energy rays has been actively conducted, and among them, printing inks,
Practical applications are progressing in fields such as clear varnishes, paints, adhesives, and photoresists. These are radically polymerizable monomers and prepolymers that have radical polymerizability, and if necessary, a radical polymerization initiator.
顔料からなっており、プレポリマーとしてはアルキッド
アクリレート、ポリエステルアクリレート エポキシア
クリレート ウレタン変性アクリレート等が、またモノ
マーとしては、ビスフェノールAアルキレンオキサイド
付加体ジアクリレート、ネオペンチルグリコールジアク
リレート、トリメチロールプロパントリアクリレート、
テトラメチロールメタンテトラアクリレート、ジペンタ
エリスリトールへキサアクリレート。The prepolymer includes alkyd acrylate, polyester acrylate, epoxy acrylate, urethane-modified acrylate, etc., and the monomer includes bisphenol A alkylene oxide adduct diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate,
Tetramethylolmethanetetraacrylate, dipentaerythritol hexaacrylate.
アルキルフェノールアルキレンオキサイド付加体モノア
クリレート等が用いられていた。Alkylphenol alkylene oxide adduct monoacrylate and the like have been used.
しかし、これらの化合物を用いた硬化性被覆組成物は例
えば、印刷インキに用いた場合、印刷時の汚れ。However, curable coating compositions using these compounds, for example, when used in printing inks, may cause stains during printing.
インキの乳化により転移不良が生じる事が多い。従って
、これらの硬化性被覆剤の適用範囲を狭めているのが実
状であった。Emulsification of ink often causes poor transfer. Therefore, the actual situation is that the scope of application of these curable coating materials has been narrowed.
「発明の構成」
(問題点を解決するための手段)
本発明は、これらの欠点を改良すべく鋭意研究の結果、
印刷適性等に優れた。活性エネルギー線硬化性被覆組成
物を発明するに至った。 すなわち。"Structure of the Invention" (Means for Solving Problems) The present invention has been developed as a result of intensive research to improve these drawbacks.
Excellent printability. This led to the invention of an active energy ray-curable coating composition. Namely.
(A)ペンタデセニルコハク酸またはその無水物を使用
して得られたアルキッド樹脂。(A) Alkyd resin obtained using pentadecenylsuccinic acid or its anhydride.
(B)ラジカル重合性二重結合を存するモノマー。(B) A monomer containing a radically polymerizable double bond.
(C)必要に応じてラジカル重合開始剤。(C) A radical polymerization initiator if necessary.
を含むことを特徴とする活性エネルギー線硬化性被覆組
成物に関するものである。The present invention relates to an active energy ray-curable coating composition comprising:
本発明について詳しく述べると一般にアルキッド樹脂と
は多価アルコールに架橋剤としての多価カルボン酸と変
性剤として一塩基酸をエステル化反応させるものであり
、この多価カルボン酸の一部又は全部にペンタデセニル
無水コハク酸を使用するものである。To explain the present invention in detail, alkyd resin is generally produced by esterifying a polyhydric alcohol with a polyhydric carboxylic acid as a crosslinking agent and a monobasic acid as a modifier. It uses pentadecenyl succinic anhydride.
多価アルコールとして1例えば、エチレングリコール、
ジエチレングリコール、トリエチレングリコール。1 as a polyhydric alcohol, for example, ethylene glycol,
Diethylene glycol, triethylene glycol.
ポリエチレングリコール、プロピレングリコール、ジプ
ロピレングリコール、トリプロピレングリコール。Polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol.
ポリプロピレングリコール、ブチレングリコール、ペン
チル゛グリコール、ネオペンチルグリコール、ヘキサン
ジオール、グリセリン、ジグリセリン1 トリメチロー
ルプロパン、ジトリメチロールプロパン、トリメチロー
ルエタン、ジトリメチロールエタン、テトラメチロール
メタン、ジペンタエリスリトール、ポリシクロペンタジ
ェンジアリルアルコールコポリマー、スピログリコール
、ビスフェノールAエチレンオキサイド付加体、ビスフ
ェノールAプロピレンオキサイド付加体。Polypropylene glycol, butylene glycol, pentyl glycol, neopentyl glycol, hexanediol, glycerin, diglycerin 1, trimethylolpropane, ditrimethylolpropane, trimethylolethane, ditrimethylolethane, tetramethylolmethane, dipentaerythritol, polycyclopentadiene Diallyl alcohol copolymer, spiroglycol, bisphenol A ethylene oxide adduct, bisphenol A propylene oxide adduct.
ビスフェノールFエチレンオキサイド付加体、ビスフェ
ノールFプロピレンオキサイド付加体(アルキレンオキ
サイドの付加モル数はビスフェノールの水酸基1個に対
し1通常1〜2モルである。)、水添加ビスフェノール
A、水添加ビスフェノールF等である。Bisphenol F ethylene oxide adduct, bisphenol F propylene oxide adduct (the number of moles of alkylene oxide added is usually 1 to 2 moles per 1 hydroxyl group of bisphenol), water-added bisphenol A, water-added bisphenol F, etc. be.
なお、ビスフェノール類に対するアルキレンオキサイド
の付加は、オートクレーブ中にビスフェノール類と、触
媒としての水酸化ナトリウム約0.5重量%(アルキレ
ンオキサイドを含めた全仕込み量に対して)を仕込み、
アルキレンオキサイドを徐々に仕込み、160℃、5k
g/cj以下で反応させ、ゲージ圧0.1 kg /
cnt以下で終点とする。To add alkylene oxide to bisphenols, add bisphenols and about 0.5% by weight of sodium hydroxide as a catalyst (based on the total amount charged including alkylene oxide) in an autoclave.
Gradually add alkylene oxide, 160℃, 5k
g/cj or less, with a gauge pressure of 0.1 kg/
The end point is below cnt.
又多塩基酸としてペンタデセニルコハク酸、又はその無
水物とさらに併用する場合は、併用する多価カルボン酸
、すなわち2個以上のカルボキシル基を有する有機化合
物はシュウ酸、マロン酸、コハク酸、ドデセニルコハク
酸、グルタル酸、マレイン酸またはそれらの酸無水物、
フマル酸、アジピン酸、ピメリン酸、スペリン酸、アゼ
ライン酸、セバシン酸、03K−DASL−12,03
K−DASL−20,03K−DASB−12,03K
−DASB−20,03K−DAUL−20,03K−
DAUB−20(O3Kシリーズは間材製油(製)長鎖
二塩基酸)、アマニ油脂肪酸や桐油脂肪酸等のダイマー
酸などの脂肪族ジカルボン酸。In addition, when used in combination with pentadecenylsuccinic acid or its anhydride as a polybasic acid, the polycarboxylic acid used in combination, that is, an organic compound having two or more carboxyl groups, is oxalic acid, malonic acid, or succinic acid. , dodecenylsuccinic acid, glutaric acid, maleic acid or their acid anhydrides,
Fumaric acid, adipic acid, pimelic acid, speric acid, azelaic acid, sebacic acid, 03K-DASL-12,03
K-DASL-20,03K-DASB-12,03K
-DASB-20,03K-DAUL-20,03K-
Aliphatic dicarboxylic acids such as DAUB-20 (O3K series is a long-chain dibasic acid manufactured by Intermediate Oil Co., Ltd.), dimer acids such as linseed oil fatty acids and tung oil fatty acids.
0−フタル酸、水添加0−フタル酸、ハイミック酸。0-phthalic acid, water-added 0-phthalic acid, Himic acid.
メチルハイミック酸、ジフェン酸、トリメリット酸。Methylhimic acid, diphenic acid, trimellitic acid.
ピロメリット酸、ナフタリン酸、ベンゾフェノンテトラ
カルボン酸およびそれらの酸無水物、イソフタル酸。Pyromellitic acid, naphthalic acid, benzophenonetetracarboxylic acid and their acid anhydrides, isophthalic acid.
テレフタル酸、ヘミメリト酸、トリメシン酸、ブレニド
酸、メロファン酸、ベンゼンペンタカルボン酸、ベンゼ
ンヘキサカルボン酸、ホモフタル酸、o、m、pフェニ
レン酢酸、0−フェニレン酢酸−β−プロピオン酸等の
芳香族多価カルボン酸、ロジンのダイマー酸等が挙げら
れる。Aromatic polyesters such as terephthalic acid, hemimellitic acid, trimesic acid, brenidic acid, merophanic acid, benzenepentacarboxylic acid, benzenehexacarboxylic acid, homophthalic acid, o, m, p phenylene acetic acid, 0-phenylene acetic acid-β-propionic acid, etc. Examples include carboxylic acids, rosin dimer acids, and the like.
一個カルボン酸としては、ギ酸、酢酸、プロピオン酸、
酪酸、バレリアン酸、トリメチル酢酸、カプロン酸、n
−へブタン酸、カプリル酸、ペラルゴン酸、メトキシ酢
酸、ヤシ油脂肪酸、バルミチン酸、ステアリン酸、オレ
イン酸、リノール酸、リルン酸等の脂肪族カルボン酸、
安息香酸、アルキル安息香酸、アルキルアミノ安息香酸
、フェニル酢酸、ハロゲン化安息香酸、アニス酸、ベン
ゾイル安息香酸、ナフトエ酸等の芳香族カルボン酸、ロ
ジン、水添加ロジン等がある。Single carboxylic acids include formic acid, acetic acid, propionic acid,
butyric acid, valeric acid, trimethylacetic acid, caproic acid, n
- aliphatic carboxylic acids such as hebutanoic acid, caprylic acid, pelargonic acid, methoxyacetic acid, coconut oil fatty acid, valmitic acid, stearic acid, oleic acid, linoleic acid, lilunic acid, etc.
Examples include aromatic carboxylic acids such as benzoic acid, alkylbenzoic acid, alkylaminobenzoic acid, phenylacetic acid, halogenated benzoic acid, anisic acid, benzoylbenzoic acid, and naphthoic acid, rosin, and water-added rosin.
さらには前述の二価カルボン酸と、−価アルコールまた
は一個のアルコール性水酸基を残したエステル化物と、
のエステル化物がある。Furthermore, the above-mentioned dihydric carboxylic acid and a -hydric alcohol or an esterified product with one alcoholic hydroxyl group remaining,
There are esterified products of
なお、−価アルコールとしては、メチルアルコール。In addition, the -valent alcohol is methyl alcohol.
エチルアルコール、プロピルアルコール、アリルアルコ
ール、ブチルアルコール、アミルアルコール、ヘキシル
アルコール、オクチルアルコール、カプリルアルコール
、デシルアルコール、ラウリルアルコール、ミリスチル
アルコール、セチルアルコール、ステアリルアルコール
等の脂肪族アルコール、ベンジルアルコール、フェノー
ル、アルキルフェノールのアルキレンオキサイド付加物
1等の芳香族アルコール、シクロヘキサノール、ロジン
アルコール、水添加ロジンアルコール等が挙げられる。Aliphatic alcohols such as ethyl alcohol, propyl alcohol, allyl alcohol, butyl alcohol, amyl alcohol, hexyl alcohol, octyl alcohol, caprylic alcohol, decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, benzyl alcohol, phenol, alkyl phenol Examples include aromatic alcohols such as alkylene oxide adduct 1, cyclohexanol, rosin alcohol, and water-added rosin alcohol.
また、1個のアルコール性水酸基を残したエステル化物
とは先に記載されたー価力ルボン酸とのエステル化物で
ある。Furthermore, the esterified product with one alcoholic hydroxyl group remaining is the esterified product with the above-mentioned carboxylic acid.
次にその反応方法について述べる。Next, the reaction method will be described.
攪拌機4つロフラスコに多価アルコールと多塩基酸。Polyhydric alcohol and polybasic acid in a 4-roof flask with a stirrer.
−価カルボン酸を官能基比(OH/C0OH基比)0゜
5〜2.0の間で仕込み、さらに必要に応じて不活性反
応溶媒を入れ、窒素又は炭酸ガス等の不活性ガスを吹き
込みながら、反応温度80〜300℃、好ましくは15
0〜260℃で理論量の90%以上反応させる。-valent carboxylic acid at a functional group ratio (OH/C0OH group ratio) between 0°5 and 2.0, and if necessary, add an inert reaction solvent and blow inert gas such as nitrogen or carbon dioxide gas. while the reaction temperature is 80 to 300°C, preferably 15°C.
90% or more of the theoretical amount is reacted at 0 to 260°C.
反応は酸価で追うのがよい。It is best to follow the reaction using the acid value.
又、−塩基酸がラジカル二重結合性をもったー塩基酸2
例えば(メタ)アクリル酸、ソルビン酸、桂皮酸。In addition, - the basic acid has radical double bond properties - the basic acid 2
For example (meth)acrylic acid, sorbic acid, cinnamic acid.
ビニール酢酸、クロトン酸を反応させる場合は多価アル
コールと多価カルボン酸、−価カルボン酸のエステル化
反応させた残OH化合物と80〜120℃で行う。When vinyl acetic acid and crotonic acid are reacted, the reaction is carried out at 80 to 120° C. with the residual OH compound resulting from the esterification reaction of polyhydric alcohol, polycarboxylic acid, and -carboxylic acid.
その際必要に応じて空気吹き込み下で塩酸、硫酸、P−
トルエンスルホン酸等の反応触媒、ハイドロキノン等の
重合禁止剤を用いる。Hydrochloric acid, sulfuric acid, P-
A reaction catalyst such as toluenesulfonic acid and a polymerization inhibitor such as hydroquinone are used.
本発明の被覆組成物は、樹脂(A)の他に、必要に応じ
てラジカル重合性二重結合を有する他のプレポリマーま
たはモノマー(B)の1種または2種以上を含むが、そ
のモノマーとしてはメチル(メタ)アクリレート、エチ
ル(メタ)アクリレート、プロピル(メタ)アクリレー
ト アリル(メタ)アクリレート、ブチル(メタ)アク
リレート、アミル(メタ)アクリレート、ヘキシル(メ
タ)アクリレート、オクチル(メタ)アクリレート、カ
プリル(メタ)アクリレート。The coating composition of the present invention contains, in addition to the resin (A), one or more other prepolymers or monomers (B) having radically polymerizable double bonds as necessary. Examples include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, allyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, octyl (meth)acrylate, caprylic (meth)acrylate.
デシル(メタ)アクリレート、ラウリル(メタ)アクリ
レート、ミリスチル(メタ)アクリレート、セチル(メ
タ)アクリレート、ステアリル(メタ)アクリレート、
ベンジル(メタ)アクリレート アルキルフェノールの
アルキレンオイサイド付加物の(メタ)アクリレート、
シクロヘキシル(メタ)アクリレート等の1官能モノマ
ーが挙げられる。さらに2官能以上の七ツマ−としてエ
チレングリコールジ(メタ)アクリレート、ジエチレン
グリコールジ(メタ)アクリレートトリエチレングリコ
ールジ(メタ)アクリレート、ポリエチレングリコール
ジ(メタ)アクリレート、ブロビレングリコールジ(メ
タ)アクリレート ジプロピレングリコールジ(メタ)
アクリレート、トリプロピレングリコールジ(メタ)ア
クリレート、トリプロピレングリコールジ(メタ)アク
リレート、ブチレングリコールジ(メタ)アクリレート
、ペンチルグリコール(メタ)アクリレート、ネオペン
チルグリコールジ(メタ)アクリレート、ヒドロキシピ
パリルヒドロキシピパレートジ(メタ)アクリレート、
ヘキサンジオールジ(メタ)アクリレート (ジ)グリ
セリントリ(メタ)アクリレート、ジグリセリンアルキ
レンオキサイドテトラ(メタ)アクリレート、トリメチ
ロールプロパントリ (メタ)アクリレート、トリメチ
ロールプロパンアルキレンオキサイドトリ (メタ)ア
クリレート、ジトリメチロールプロパンテトラ(メタ)
アクリレート、ジトリメチロールプロパンアルキレンオ
キサイドテトラ(メタ)アクリレート トリメチロール
エタントリ (メタ)アクリレート ジトリメチロール
エタントリ (メタ)アクリレート、トリメチロールエ
タンアルキレンオキサイドトリ (メタ)アクリレート
。Decyl (meth)acrylate, lauryl (meth)acrylate, myristyl (meth)acrylate, cetyl (meth)acrylate, stearyl (meth)acrylate,
Benzyl (meth)acrylate (meth)acrylate of alkylene oidide adduct of alkylphenol,
Examples include monofunctional monomers such as cyclohexyl (meth)acrylate. Furthermore, as heptadons with more than two functional groups, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, brobylene glycol di(meth)acrylate, dipropylene Glycoldi (meth)
Acrylate, tripropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, pentyl glycol (meth)acrylate, neopentyl glycol di(meth)acrylate, hydroxypiparyl hydroxypiparate di(meth)acrylate,
Hexanediol di(meth)acrylate (di)glycerin tri(meth)acrylate, diglycerin alkylene oxide tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane alkylene oxide tri(meth)acrylate, ditrimethylolpropane Tetra (meta)
Acrylate, ditrimethylolpropane alkylene oxide tetra(meth)acrylate Trimethylolethane tri(meth)acrylate Ditrimethylolethane tri(meth)acrylate, trimethylolethane alkylene oxide tri(meth)acrylate.
ジトリメチロールエタンアルキレンオキサイドテトロ(
メタ)アクリレート、テトラメチロールメタンテトラ(
メタ)アクリレート、ジペンタエリスリトールヘキサ(
メタ)アクリレート、ビスフェノールAアルキレンオキ
サイドラ(メタ)アクリレート ビスフェノールFアル
キレンオキサイドラ(メタ)アクリレート。ditrimethylolethane alkylene oxide tetro(
meth)acrylate, tetramethylolmethanetetra(
meth)acrylate, dipentaerythritol hexa(
meth)acrylate, bisphenol A alkylene oxide dra(meth)acrylate Bisphenol F alkylene oxide dra(meth)acrylate.
ジヒドロキシベンゼンアルキレンオキサイドジ(メタ)
アクリレート トリヒドロキシベンゼンアルキレンオキ
サイドジ(メタ)アクリレート、水添加ビスフェノール
Aジ(メタ)アクリレート、水添加ビスフェノールFジ
(メタ)アクリレート、水添加ビスフェノールAアルキ
レンオキサイド付加体ジ(メタ)アクリレ−h、水添加
ビスフェノールFアルキレンオキサイド付加体ジ(メタ
)アクリレート等が挙げられる。さらにその他にラクト
ン付加体の七ツマ−が挙げられる。Dihydroxybenzene alkylene oxide di(meth)
Acrylate Trihydroxybenzene alkylene oxide di(meth)acrylate, water-added bisphenol A di(meth)acrylate, water-added bisphenol F di(meth)acrylate, water-added bisphenol A alkylene oxide adduct di(meth)acrylate-h, water-added Examples include bisphenol F alkylene oxide adduct di(meth)acrylate. In addition, lactone adducts such as lactones may be mentioned.
すなわち、ポリエチレングリコールボリラクトネートジ
(メタ)アクリレート、ポリプロピレングリコールボリ
ラクトネートジ(メタ)アクリレート、アルキレングリ
コールポリラクトネートジ(メタ)アクリレート、グリ
セリンポリラクトネートトリ (メタ)アクリレート
ジグリセリンポリラクトネートテトラ(メタ)アクリレ
ート トリメチロールプロパンポリラクトネートトリ
(メタ)アクリレート、ジトリメチロールプロパンテト
ラ(メタ)アクリレート、ペンタエリスリトールポリラ
クトネートテトラ(メタ)アクリレート、ジペンタエリ
スリトールポリラクトネートへキサアクリレート等の各
ポリオールラクトネートポリアクリレートである。なお
、上記モノマーのラクトンはγ−ブチロラクトン8−バ
レロラクトン、ε−カプロラクトン等のエステルの官能
基−CO−O−を環内に含む化合物である。Namely, polyethylene glycol polylactonate di(meth)acrylate, polypropylene glycol polylactonate di(meth)acrylate, alkylene glycol polylactonate di(meth)acrylate, glycerin polylactonate tri(meth)acrylate.
Diglycerin polylactonate tetra(meth)acrylate Trimethylolpropane polylactonate tri
(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol polylactonate tetra(meth)acrylate, dipentaerythritol polylactonate hexaacrylate, and other polyol lactonate polyacrylates. The lactone monomer is a compound containing an ester functional group -CO-O- in the ring, such as γ-butyrolactone, 8-valerolactone, and ε-caprolactone.
本発明の被覆剤の使用において、活性エネルギー線が紫
外線である場合には、光増感剤、すなわちラジカル重合
開始剤(ラジカル重合促進剤も)(C)を添加する必要
があり、ベンゾイン、ベンゾインメチルエーテル、ベン
ゾインエチルエコチル。ベンゾインイソプロピルエーテ
ル、α−アクリルベンゾイン等のベンゾイン系増感剤、
ベンゾフェノン、p−メチルベンゾフェノン、p−クロ
ロベンゾフェノン、テトラクロロベンゾフェノン、0−
ベンゾイル安息香酸メチル、アセトフェノン等のアリー
ルケトン系増感剤、4,4−ビスジエチルアミノベンゾ
フェノン、p−ジメチルアミノ安息香酸イソアミル、p
−ジメチルアミノアセトフヱノン等のジアルキルアミノ
アリールケトン系増感剤。When using the coating material of the present invention, when the active energy ray is ultraviolet rays, it is necessary to add a photosensitizer, that is, a radical polymerization initiator (also a radical polymerization accelerator) (C), and benzoin, benzoin Methyl ether, benzoin ethyl ecotyl. Benzoin-based sensitizers such as benzoin isopropyl ether and α-acrylic benzoin,
Benzophenone, p-methylbenzophenone, p-chlorobenzophenone, tetrachlorobenzophenone, 0-
Aryl ketone sensitizers such as methyl benzoylbenzoate and acetophenone, 4,4-bisdiethylaminobenzophenone, isoamyl p-dimethylaminobenzoate, p
-Dialkylaminoarylketone sensitizers such as dimethylaminoacetophenone.
チオキサントン、キサントンおよびそのハロゲン置換体
等の多環カルボニル系増感剤が挙げられ、これらの単独
もしくは適宜組み合せにより用いることもできる。Examples include polycyclic carbonyl sensitizers such as thioxanthone, xanthone, and halogen-substituted products thereof, and these can be used alone or in appropriate combinations.
これらの光増感剤は組成物中に1〜30重量%の範囲で
用いることができるが、好ましくは0〜15重量%の範
囲であることが望ましい。These photosensitizers can be used in the composition in an amount of 1 to 30% by weight, preferably in a range of 0 to 15% by weight.
また1本発明(A)の樹脂と乾性油、パラフィン。In addition, the resin of the present invention (A), drying oil, and paraffin.
オレフィン、芳香族ソルベント等の組み合わせで熱重合
、酸化重合型にも使用できる。It can also be used for thermal polymerization and oxidative polymerization in combination with olefins, aromatic solvents, etc.
活性エネルギー線硬化性インキ組成物とするには上記希
釈ワニスに通常は顔料を分散させるが、この方法は特に
限定されることなく、三本ロール、ボールミル等の常法
の分散方法において行うことができる。また。To prepare an active energy ray-curable ink composition, pigments are usually dispersed in the above-mentioned diluted varnish, but this method is not particularly limited and can be carried out by a conventional dispersion method such as a three-roll mill or a ball mill. can. Also.
有機、無機1体質顔料の他に、必要に応じて可塑剤。In addition to organic and inorganic basic pigments, plasticizers are used as needed.
界面活性剤、熱重合禁止剤等を添加することができる。Surfactants, thermal polymerization inhibitors, etc. can be added.
勿論、R料を使用していないインキ組成物があってもよ
い。さらに本発明の効果を阻害しない範囲で他の樹脂を
併用することも可能である。Of course, there may be ink compositions that do not use the R material. Furthermore, it is also possible to use other resins in combination within a range that does not impede the effects of the present invention.
以下、具体例により本発明を説明する。例中の部は全て
重量部を示す。The present invention will be explained below using specific examples. All parts in the examples indicate parts by weight.
製造例−1
トリメチロールプロパン 268部無水
フタル酸 148部トルエ
ン 20部を攪拌機4
つロフラスコに仕込み窒素ガス気流下で200℃で5時
間反応させ酸価4.8になったので冷却しハイドロキノ
ン0.6部、p−トルエンスルホン酸6部を仕込み空気
を吹き込みながらアクリル酸260部を仕込み、100
℃で10時間後、酸価が9゜9になったので脱溶媒し、
くみ出した。Production Example-1 268 parts of trimethylolpropane 148 parts of phthalic anhydride 20 parts of toluene were added to the stirrer 4
The mixture was charged into a double-bottomed flask and reacted at 200°C for 5 hours under a stream of nitrogen gas until the acid value reached 4.8. After cooling, 0.6 parts of hydroquinone and 6 parts of p-toluenesulfonic acid were added and 260 parts of acrylic acid was added while blowing air. Prepare 100
After 10 hours at °C, the acid value reached 9°9, so the solvent was removed.
I pumped it out.
これを樹脂aとする。This will be referred to as resin a.
製造例−2
トリメチロールプロパン 268部ペン
タデセニル無水コハク酸 310部トルエン
25部を攪拌a4つ
目フラスコに仕込み窒素ガス気流下で200℃で5時間
反応させ、酸価4.9になったので冷却し、ハイドロキ
ノン0.7部、p−1−ルエンスルホン酸7部を仕込み
空気を吹き込みながらアクリル酸260部を仕込み、1
00℃で10時間後酸価が9.8になったので脱溶媒し
、くみ出した。Production Example-2 268 parts of trimethylolpropane 310 parts of pentadecenyl succinic anhydride 25 parts of toluene were stirred into a fourth flask and reacted at 200°C for 5 hours under a stream of nitrogen gas. When the acid value reached 4.9, the mixture was cooled. , 0.7 parts of hydroquinone and 7 parts of p-1-luenesulfonic acid were charged, and while blowing air, 260 parts of acrylic acid was added.
After 10 hours at 00°C, the acid value reached 9.8, so the solvent was removed and pumped out.
これを樹脂すとする。Let's call this a resin.
製造例−3
グリセリン 148部コハク
酸 118部0−ベンゾイ
ル安息香酸 813部トルエン
75部を攪拌機4つロフラス
コに仕込み窒素ガス気流下で200℃で11時間反応さ
せ酸価4.7になったので脱溶媒し、くみ出した。Production Example-3 Glycerin 148 parts Succinic acid 118 parts 0-benzoylbenzoic acid 813 parts Toluene
75 parts were placed in a flask equipped with four stirrers and reacted at 200°C for 11 hours under a stream of nitrogen gas. When the acid value reached 4.7, the solvent was removed and pumped out.
これを樹脂Cとする。This will be referred to as resin C.
製造例−4
グリセリン 184部ペンタ
デセニルコハク酸328 部
0−ベンゾイル安息香酸 813部トル
エン 75部を攪拌機
4つロフラスコに仕込み窒素ガス気流下で200℃で1
1時間反応させ酸価4.8になったので脱溶媒し、くみ
出した。Production Example-4 Glycerin 184 parts Pentadecenyl succinic acid 328 parts O-benzoylbenzoic acid 813 parts Toluene 75 parts were placed in a flask equipped with four stirrers and heated at 200°C under a nitrogen gas stream.
After reacting for 1 hour, the acid value reached 4.8, so the solvent was removed and pumped out.
これを樹脂dとする。This will be referred to as resin d.
製造例−5
ペンタエリスリトール 272部イ
ソフタル酸 166部水添加
ロジン 990部トルエン
70部を攪拌機4つロ
フラスコに仕込み窒素ガス気流下で200℃で10時間
反応させ酸価4.0になったので冷却シ、ハイドロキノ
ン1.3部、P−トルエンスルホン酸13部を仕込み空
気を吹き込みながらアクリル酸194部を仕込み100
℃で9時間酸酢価が9゜8になったので脱溶媒し、くみ
出した。Production example-5 Pentaerythritol 272 parts Isophthalic acid 166 parts Water-added rosin 990 parts Toluene
70 parts were placed in a flask equipped with four stirrers and reacted at 200°C for 10 hours under a stream of nitrogen gas until the acid value reached 4.0. After cooling, 1.3 parts of hydroquinone and 13 parts of P-toluenesulfonic acid were added and air was introduced. While blowing, add 194 parts of acrylic acid to 100 parts.
After 9 hours at °C, the acid acetic acid value reached 9.8, so the solvent was removed and the mixture was pumped out.
これを樹脂eとする。This will be referred to as resin e.
製造例−5
ペンタエリスリトール 272部イ
ソフタル酸 166部水添
加ロジン 990部トルエン
70部を攪拌機4つ
ロフラスコに仕込み窒素ガス気流下で200℃で10時
間反応させ酸価4.0になったので冷却し、ハイドロキ
ノン1.3部、p−トルエンスルホン酸13部を仕込み
、空気を吹き込みながらアクリル酸194部を仕込み、
100℃で9時間酸酢価が9.8になったので脱溶媒し
、くみ出した。Production Example-5 Pentaerythritol 272 parts Isophthalic acid 166 parts Water-added rosin 990 parts Toluene 70 parts were placed in a flask with four stirrers and reacted at 200°C for 10 hours under a stream of nitrogen gas. When the acid value reached 4.0, the mixture was cooled. , 1.3 parts of hydroquinone and 13 parts of p-toluenesulfonic acid were charged, and 194 parts of acrylic acid was charged while blowing air.
After 9 hours at 100°C, the acid acetic acid value reached 9.8, so the solvent was removed and pumped out.
これを樹脂eとする。This will be referred to as resin e.
製造例−6
ペンタエリスリトール 272部ペ
ンタデセニル無水コハク酸 310部水添加
ロジン 990部トルエン
75部を攪拌機4つロ
フラスコに仕込み窒素ガス気流下で200℃で10時間
反応させ酸価4.5以下になったので冷却し、ハイドロ
キノン1.6部、P−トルエンスルホン酸16部を仕込
み空気を吹き込みながらアクリル酸194部を仕込み1
00.℃で9時間酸酢価が9.7になったので脱溶媒し
、くみ出した。Production Example-6 Pentaerythritol 272 parts Pentadecenyl succinic anhydride 310 parts Water-added rosin 990 parts Toluene
75 parts were placed in a flask equipped with four stirrers and reacted at 200°C for 10 hours under a stream of nitrogen gas. When the acid value became 4.5 or less, the mixture was cooled, and 1.6 parts of hydroquinone and 16 parts of P-toluenesulfonic acid were placed in the air. Add 194 parts of acrylic acid while blowing in 1
00. After 9 hours at °C, the acid acetic acid value reached 9.7, so the solvent was removed and the mixture was pumped out.
これを樹脂fとする。This is referred to as resin f.
次に上記樹脂とモノマー等を用い活性エネルギー線硬化
性被覆組成物を作製した。Next, an active energy ray-curable coating composition was prepared using the above resin, monomer, etc.
以下重量平均分子量とその組成物の処方を表に示す。The weight average molecular weight and the formulation of the composition are shown in the table below.
(注−1)モノマー
ABPE−47ビスフ工ノールAモルエチレンオキサイ
ド付加体ジアクリレート
TMPTA : トリメチロールプロパントリアクリレ
ート
TMPEOA : トリメチロールプロパン3モルエチ
レンオキサイド付加体トリアクリレ
ート
光増感剤:4,4−ビス(ジエチルアミノ)ベンゾフェ
ノン/ベンゾフェノン−215
顔料:ファイネスレッドF2BW:東洋インキ製造側製
紅顔料
実施例1
表−1に示す被覆組成物(印刷インキ)、すなわち、比
較例サンプル1〜4.実施例サンプル5〜8をKORD
ハイデルベルグで印刷し、印刷時の非画線部への汚れ、
水中(注−2)を測定した(表−2)。(Note-1) Monomer ABPE-47 bisphenol A mole ethylene oxide adduct diacrylate TMPTA: Trimethylolpropane triacrylate TMPEOA: Trimethylolpropane 3 mole ethylene oxide adduct triacrylate Photosensitizer: 4,4-bis (Diethylamino)benzophenone/benzophenone-215 Pigment: Fines Red F2BW: Red pigment manufactured by Toyo Ink Manufacturing Company Example 1 The coating composition (printing ink) shown in Table 1, that is, Comparative Example Samples 1 to 4. KORD example samples 5 to 8
Printed with Heidelberg, stains on non-printing areas during printing,
In water (Note-2) was measured (Table-2).
表−2
(注−2)水中:印刷機に湿し水の量をコントロールす
る装置を設けて測定した。数字は湿し水の量を表す目盛
りで特に単位はない。Table 2 (Note 2) Underwater: Measured by installing a device to control the amount of dampening water in the printing press. The numbers are scales that represent the amount of dampening water, and there is no specific unit.
表中下限の数字は水の量を少なくしていった時の汚れの
発生した水の量を表す。また、上限の数字は水の量を多
くしていった場合にインキが乳化して転移不良になった
水の量を表す。The lower limit number in the table represents the amount of water in which stains were generated when the amount of water was decreased. Further, the upper limit number represents the amount of water at which the ink becomes emulsified and poor transfer occurs when the amount of water is increased.
実施例−2
実施例−1で印刷した被覆組成物を比較例サンプル1〜
3.実施例サンプル5/7について80W/口の強度を
有する高圧水銀灯2灯の下10cmのところをコンベヤ
ーにのせ100m/分照射した。又比較例サンプル4.
実施例サンプル8についてはカーテンビーム型電子線照
射装置を用い3Mr a dで照射した。いずれも硬化
していた。Example-2 The coating composition printed in Example-1 was used as comparative sample 1 to
3. Example samples 5/7 were placed on a conveyor and irradiated at a distance of 10 cm from two high-pressure mercury lamps having an intensity of 80 W/mouth at a rate of 100 m/min. Comparative example sample 4.
Example sample 8 was irradiated at 3 Mr ad using a curtain beam type electron beam irradiation device. Both were hardened.
本発明の活性エネルギー線硬化性被覆組成物は従来知ら
れている被覆剤に比べ、実施例1.実施例2に示されて
いるように印刷効果がよく、活性エネルギー線効果性被
覆組成物の適用範囲を広めることができる。The active energy ray-curable coating composition of the present invention was compared with the conventionally known coating composition in Example 1. As shown in Example 2, the printing effect is good and the range of application of the active energy ray effective coating composition can be expanded.
手続補正書(自発)
昭和し年l>月】7日
1、事件の表示 昭和62年特許願第273359号2
、発明の名称 活性エネルギー線硬化性被覆組成物3、
補正をする者
事件との関係 特許出願人
住所 東京都中央区京橋二丁目3番13号4、補正の
対象
明細書の「発明の詳細な説明」の欄
(1)明細書第2頁第17行の「被覆剤」を「被覆組成
物」に訂正する。Procedural amendment (spontaneous) Showa year 1 > month] 7th 1, case description 1988 Patent Application No. 273359 2
, Title of the invention Active energy ray curable coating composition 3,
Relationship with the case of the person making the amendment Patent applicant address: 2-3-13-4 Kyobashi, Chuo-ku, Tokyo, “Detailed description of the invention” column (1) of the specification to be amended, page 2, number 17 of the specification Correct the line "Coating agent" to "Coating composition".
(2)明細書第3頁第11行の「−塩基酸」を「−価カ
ルボン酸」に訂正する。(2) "-Basic acid" on page 3, line 11 of the specification is corrected to "-valent carboxylic acid."
(3)明細書第4頁第18行の「多塩基酸」を「多価カ
ルボン酸」に訂正する。(3) "Polybasic acid" on page 4, line 18 of the specification is corrected to "polycarboxylic acid."
(4)明細書第7頁第10行の「−塩基酸」を「−価カ
ルボン酸」に訂正する。(4) "-Basic acid" on page 7, line 10 of the specification is corrected to "-valent carboxylic acid."
(5)明細書第7頁第10〜11行の「−塩基酸」を「
−価カルボン酸」に訂正する。(5) “-Basic acid” on page 7, lines 10-11 of the specification is replaced with “
-Corrected to "carboxylic acid".
(6)明細書第15頁第5〜16行の「製造例−5・・
・・・・これを樹脂eとする。」を削除する。(6) "Production Example-5..." on page 15, lines 5 to 16 of the specification.
...This is referred to as resin e. ” to be deleted.
(7)明細書第19頁の表−2において、実施例サンプ
ル7の「汚れ発生開始枚数」の欄がr20,000枚で
発生」となっているのをr20,000枚で発生なし」
に訂正する。(7) In Table 2 on page 19 of the specification, the column ``Number of sheets where stains start to occur'' for Example Sample 7 indicates that stains occur at 20,000 sheets, but no stains occur at 20,000 sheets.''
Correct to.
(8)明細書第19頁の表−2において、実施例サンプ
ル8の「汚れ発生開始枚数」の欄がr20.000枚で
発生」となっているのをr20,000枚で発生なし」
に訂正する。(8) In Table 2 on page 19 of the specification, the column ``Number of sheets where stains start to occur'' for example sample 8 indicates that stains occur at r20,000 sheets, but no stains occur at r20,000 sheets.''
Correct to.
(9)明細書第20頁第8行のr5/7Jを「5〜7」
に訂正する。(9) r5/7J on page 20, line 8 of the specification is “5-7”
Correct to.
Claims (1)
使用して得られたアルキッド樹脂、 (B)ラジカル重合性二重結合を有するモノマー、 (C)必要に応じてラジカル重合開始剤、 を含むことを特徴とする活性エネルギー線硬化性被覆組
成物。[Claims] 1. (A) an alkyd resin obtained using pentadecenylsuccinic acid or its anhydride, (B) a monomer having a radically polymerizable double bond, (C) as necessary. An active energy ray-curable coating composition comprising: a radical polymerization initiator;
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27335987A JPH0813953B2 (en) | 1987-10-30 | 1987-10-30 | Active energy ray curable coating composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27335987A JPH0813953B2 (en) | 1987-10-30 | 1987-10-30 | Active energy ray curable coating composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01115918A true JPH01115918A (en) | 1989-05-09 |
JPH0813953B2 JPH0813953B2 (en) | 1996-02-14 |
Family
ID=17526799
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP27335987A Expired - Lifetime JPH0813953B2 (en) | 1987-10-30 | 1987-10-30 | Active energy ray curable coating composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0813953B2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11999920B2 (en) | 2020-09-14 | 2024-06-04 | Ecolab Usa Inc. | Cold flow additives for plastic-derived synthetic feedstock |
US12031097B2 (en) | 2021-10-14 | 2024-07-09 | Ecolab Usa Inc. | Antifouling agents for plastic-derived synthetic feedstocks |
-
1987
- 1987-10-30 JP JP27335987A patent/JPH0813953B2/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11999920B2 (en) | 2020-09-14 | 2024-06-04 | Ecolab Usa Inc. | Cold flow additives for plastic-derived synthetic feedstock |
US12031097B2 (en) | 2021-10-14 | 2024-07-09 | Ecolab Usa Inc. | Antifouling agents for plastic-derived synthetic feedstocks |
Also Published As
Publication number | Publication date |
---|---|
JPH0813953B2 (en) | 1996-02-14 |
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