JP5672706B2

JP5672706B2 - 硬化性分散剤、及びそれを用いた顔料組成物並びに顔料分散体

硬化性分散剤、及びそれを用いた顔料組成物並びに顔料分散体 Download PDF

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Publication number: JP5672706B2
Authority: JP; Japan
Prior art keywords: group; meth; pigment; general formula; isocyanate
Prior art date: 2010-01-29
Legal status : Active

Application number

JP2010017896A

Other languages

English (en)

Japanese (ja)

Other versions

JP2011157416A5 (zh

JP2011157416A (ja

Inventor

友子鈴木

三上　譲司

譲司三上

奈津子松下

睦中里

努廣嶋

Current Assignee

Toyo Ink SC Holdings Co Ltd

Original Assignee

Toyo Ink SC Holdings Co Ltd

Priority date

2010-01-29

Filing date

2010-01-29

Publication date

2015-02-18

2010-01-29 Application filed by Toyo Ink SC Holdings Co Ltd filed Critical Toyo Ink SC Holdings Co Ltd

2010-01-29 Priority to JP2010017896A priority Critical patent/JP5672706B2/ja

2011-08-18 Publication of JP2011157416A publication Critical patent/JP2011157416A/ja

2012-10-11 Publication of JP2011157416A5 publication Critical patent/JP2011157416A5/ja

2015-02-18 Application granted granted Critical

2015-02-18 Publication of JP5672706B2 publication Critical patent/JP5672706B2/ja

Status Active legal-status Critical Current

2030-01-29 Anticipated expiration legal-status Critical

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239000000049 pigment Substances 0.000 title claims description 114
239000002270 dispersing agent Substances 0.000 title claims description 92
239000006185 dispersion Substances 0.000 title claims description 36
239000000203 mixture Substances 0.000 title claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
150000001875 compounds Chemical class 0.000 claims description 70
-1 tetracarboxylic anhydride Chemical class 0.000 claims description 64
239000000178 monomer Substances 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 40
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 30
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 27
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 25
125000003396 thiol group Chemical group [H]S* 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 18
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 15
229920002554 vinyl polymer Polymers 0.000 claims description 15
RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 13
150000008064 anhydrides Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000010526 radical polymerization reaction Methods 0.000 claims description 9
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
150000003918 triazines Chemical class 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
150000002596 lactones Chemical class 0.000 claims description 7
DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 claims description 6
QASBHTCRFDZQAM-UHFFFAOYSA-N (2-isocyanato-2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)N=C=O QASBHTCRFDZQAM-UHFFFAOYSA-N 0.000 claims description 5
125000004018 acid anhydride group Chemical group 0.000 claims description 5
239000002966 varnish Substances 0.000 claims description 5
RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 4
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 4
LJINGTWAETUGOX-UHFFFAOYSA-N 1-sulfanylethane-1,1-diol Chemical compound CC(O)(O)S LJINGTWAETUGOX-UHFFFAOYSA-N 0.000 claims description 3
VZXNRJVUNRHUSP-UHFFFAOYSA-N 1-sulfanylpropane-2,2-diol Chemical compound CC(O)(O)CS VZXNRJVUNRHUSP-UHFFFAOYSA-N 0.000 claims description 3
MFXVAKLSFXZTJU-UHFFFAOYSA-N 2-methyl-5-sulfanylpentane-1,3-diol Chemical compound OCC(C)C(O)CCS MFXVAKLSFXZTJU-UHFFFAOYSA-N 0.000 claims description 3
VYSBIWBURKYGPB-UHFFFAOYSA-N 2-sulfanylpropane-1,2-diol Chemical compound CC(O)(S)CO VYSBIWBURKYGPB-UHFFFAOYSA-N 0.000 claims description 3
NBUVVXNTRSKQSQ-UHFFFAOYSA-N 2-sulfanylpropane-1,3-diol Chemical compound OCC(S)CO NBUVVXNTRSKQSQ-UHFFFAOYSA-N 0.000 claims description 3
125000002723 alicyclic group Chemical group 0.000 claims description 3
RRCCWYJNLXYHMI-UHFFFAOYSA-N sulfanylmethanediol Chemical group OC(O)S RRCCWYJNLXYHMI-UHFFFAOYSA-N 0.000 claims description 3
HBRWZBNIICOSLD-UHFFFAOYSA-N 2-ethyl-5-sulfanylpentane-1,3-diol Chemical compound CCC(CO)C(O)CCS HBRWZBNIICOSLD-UHFFFAOYSA-N 0.000 claims description 2
NIXYDPFNCYWPLH-UHFFFAOYSA-N 2-methyl-2-sulfanylpropane-1,3-diol Chemical compound OCC(S)(C)CO NIXYDPFNCYWPLH-UHFFFAOYSA-N 0.000 claims description 2
150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 25
125000001424 substituent group Chemical group 0.000 description 20
239000000976 ink Substances 0.000 description 18
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229910052757 nitrogen Inorganic materials 0.000 description 14
239000000126 substance Substances 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
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239000007787 solid Substances 0.000 description 12
150000003628 tricarboxylic acids Chemical class 0.000 description 12
238000003860 storage Methods 0.000 description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 9
230000008859 change Effects 0.000 description 9
230000000052 comparative effect Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
150000000000 tetracarboxylic acids Chemical class 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
239000000460 chlorine Chemical group 0.000 description 7
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
229920000570 polyether Polymers 0.000 description 7
229920005862 polyol Polymers 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000004721 Polyphenylene oxide Substances 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000008065 acid anhydrides Chemical class 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 6
150000004056 anthraquinones Chemical class 0.000 description 6
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
125000002843 carboxylic acid group Chemical group 0.000 description 6
238000005259 measurement Methods 0.000 description 6
150000005846 sugar alcohols Polymers 0.000 description 6
125000000542 sulfonic acid group Chemical group 0.000 description 6
SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
239000011324 bead Substances 0.000 description 5
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 5
235000019441 ethanol Nutrition 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000011521 glass Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
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229920005906 polyester polyol Polymers 0.000 description 5
150000003077 polyols Chemical class 0.000 description 5
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 4
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
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150000007513 acids Chemical class 0.000 description 4
238000004220 aggregation Methods 0.000 description 4
230000002776 aggregation Effects 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
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 4
230000015572 biosynthetic process Effects 0.000 description 4
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125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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125000003282 alkyl amino group Chemical group 0.000 description 3
WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 3
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
239000006229 carbon black Substances 0.000 description 3
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
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125000000547 substituted alkyl group Chemical group 0.000 description 3
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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