JP2003049038A - Fine particle dispersion composition - Google Patents
Fine particle dispersion compositionInfo
- Publication number
- JP2003049038A JP2003049038A JP2001237825A JP2001237825A JP2003049038A JP 2003049038 A JP2003049038 A JP 2003049038A JP 2001237825 A JP2001237825 A JP 2001237825A JP 2001237825 A JP2001237825 A JP 2001237825A JP 2003049038 A JP2003049038 A JP 2003049038A
- Authority
- JP
- Japan
- Prior art keywords
- graft
- mass
- fine particles
- fine particle
- particle dispersion
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 239000010419 fine particle Substances 0.000 title claims description 66
- 239000006185 dispersion Substances 0.000 title claims description 36
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 48
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 48
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 33
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 24
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000006229 carbon black Substances 0.000 claims abstract description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002798 polar solvent Substances 0.000 claims abstract description 12
- 239000002270 dispersing agent Substances 0.000 claims abstract description 11
- 230000007613 environmental effect Effects 0.000 abstract description 11
- 238000010559 graft polymerization reaction Methods 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 3
- 239000011859 microparticle Substances 0.000 abstract 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 28
- 229920000642 polymer Polymers 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000178 monomer Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 229940047670 sodium acrylate Drugs 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920001721 polyimide Polymers 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 10
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- -1 acrylic ester Chemical class 0.000 description 9
- 239000011324 bead Substances 0.000 description 9
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 9
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000009719 polyimide resin Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-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
- 230000008859 change Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 2
- XGKKWUNSNDTGDS-UHFFFAOYSA-N 2,5-dimethylheptane-1,7-diamine Chemical compound NCC(C)CCC(C)CCN XGKKWUNSNDTGDS-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 2
- SGEWZUYVXQESSB-UHFFFAOYSA-N 3-methylheptane-1,7-diamine Chemical compound NCCC(C)CCCCN SGEWZUYVXQESSB-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 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 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YOAIGLJIHTWJHL-UHFFFAOYSA-N 1,1'-biphenyl;1,1,1-trifluoropropane Chemical compound CCC(F)(F)F.C1=CC=CC=C1C1=CC=CC=C1 YOAIGLJIHTWJHL-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- DZLUPKIRNOCKJB-UHFFFAOYSA-N 2-methoxy-n,n-dimethylacetamide Chemical compound COCC(=O)N(C)C DZLUPKIRNOCKJB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- YEEIWUUBRYZFEH-UHFFFAOYSA-N 3-methoxyhexane-1,6-diamine Chemical compound NCCC(OC)CCCN YEEIWUUBRYZFEH-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- ZWIBGDOHXGXHEV-UHFFFAOYSA-N 4,4-dimethylheptane-1,7-diamine Chemical compound NCCCC(C)(C)CCCN ZWIBGDOHXGXHEV-UHFFFAOYSA-N 0.000 description 1
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-UHFFFAOYSA-N 0.000 description 1
- XDYLWBWPEDSSLU-UHFFFAOYSA-N 4-(3-carboxyphenyl)benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C(C(O)=O)=CC=2)C(O)=O)=C1 XDYLWBWPEDSSLU-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- AQVOMFPTJXMAQE-UHFFFAOYSA-N 4-propylphthalic acid Chemical compound CCCC1=CC=C(C(O)=O)C(C(O)=O)=C1 AQVOMFPTJXMAQE-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- MBRGOFWKNLPACT-UHFFFAOYSA-N 5-methylnonane-1,9-diamine Chemical compound NCCCCC(C)CCCCN MBRGOFWKNLPACT-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010013642 Drooling Diseases 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- 239000004952 Polyamide Substances 0.000 description 1
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- 208000008630 Sialorrhea Diseases 0.000 description 1
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- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 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 1
- 229930003836 cresol Natural products 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GBASTSRAHRGUAB-UHFFFAOYSA-N ethylenetetracarboxylic dianhydride Chemical compound O=C1OC(=O)C2=C1C(=O)OC2=O GBASTSRAHRGUAB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000002783 friction material Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910001337 iron nitride Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は微粒子分散組成物に
関し、より詳しくは、ポリビニルピロリドンを基幹ポリ
マーとするグラフト重合体を用いて微粒子を分散させて
なる微粒子分散組成物に関する。TECHNICAL FIELD The present invention relates to a fine particle dispersion composition, and more particularly to a fine particle dispersion composition obtained by dispersing fine particles using a graft polymer having polyvinylpyrrolidone as a basic polymer.
【０００２】[0002]
【従来の技術】顔料、磁性粉、セラミックス粉体等の固
体微粒子の多くは、粒子間の凝集力に比べて他の物質、
例えば、水、有機溶剤、有機高分子等との親和力が弱い
ため二次凝集を起こしやすい。このため、液体中に第三
成分として分散剤を加え、安定な懸濁液を形成する技術
が各種開発されている。2. Description of the Related Art Most of solid fine particles such as pigments, magnetic powders, ceramics powders, etc.
For example, it has a weak affinity with water, an organic solvent, an organic polymer, etc., and is likely to cause secondary aggregation. For this reason, various techniques have been developed to form a stable suspension by adding a dispersant as a third component to a liquid.
【０００３】このような分散剤の一つに、ポリビニルピ
ロリドンやポリビニルカプロラクタム等のＮ−ビニル環
状ラクタム構造を有する高分子があり、Ｎ−ビニル環状
ラクタム構造の作用により比較的分散性に優れているこ
とが知られている。しかしながら、全ての点において満
足できる性質を有しているとはいえず、特に環境安定性
および製膜性に関しては更なる改善が求められていた。As one of such dispersants, there are polymers having an N-vinyl cyclic lactam structure such as polyvinylpyrrolidone and polyvinylcaprolactam, which are relatively excellent in dispersibility due to the action of the N-vinyl cyclic lactam structure. It is known. However, it cannot be said that it has satisfactory properties in all respects, and further improvement has been demanded especially with respect to environmental stability and film forming property.
【０００４】一方、本発明において用いられているポリ
ビニルピロリドンに対してアクリル酸がグラフト重合さ
れてなるグラフト重合体は、Ｅｕｒ．ｐｏｌｙｍ．
Ｊ．，４，ｐ３４３−３５４（１９６８）、Ｍａｃｒｏ
ｍｏｌｅｃｕｌｅｓ，２３，ｐ４４７４−４４７６（１
９９０）およびＪ．Ｍａｃｒｏｍｏｌ．Ｓｃｉ．Ｃｈｅ
ｍ．，Ａ１３（６），ｐ７５１−７６６（１９７９）に
おいて存在が示唆されている。すなわち、ポリビニルピ
ロリドン存在下でアクリル酸やマレイン酸を重合させた
時の副反応として、アクリル酸やマレイン酸のポリビニ
ルピロリドンに対するグラフト化が生じる可能性が示唆
されている。On the other hand, the graft polymer obtained by graft-polymerizing acrylic acid to polyvinylpyrrolidone used in the present invention is Eur. polym.
J. , 4, p343-354 (1968), Macro
molecules, 23, p4474-4476 (1
990) and J. et al. Macromol. Sci. Che
m. , A13 (6), p751-766 (1979). That is, it is suggested that acrylic acid or maleic acid may be grafted onto polyvinylpyrrolidone as a side reaction when polymerizing acrylic acid or maleic acid in the presence of polyvinylpyrrolidone.
【０００５】しかしながら、ポリビニルピロリドンを基
幹ポリマーとするグラフト重合体の存在に関しては、副
反応として生じる可能性が示唆されているに過ぎず、明
確な同定はされていない。しかも、これらの文献は、い
ずれもアクリル酸やマレイン酸といったカルボキシル基
含有不飽和単量体の重合を主眼として記載されているも
のであり、ポリビニルピロリドンを基幹ポリマーとする
グラフト重合体の分散剤としての使用に関しては何ら開
示されていない。However, regarding the existence of the graft polymer having polyvinylpyrrolidone as a basic polymer, only the possibility that it may occur as a side reaction has been suggested, and no clear identification has been made. Moreover, all of these documents are described with a focus on the polymerization of a carboxyl group-containing unsaturated monomer such as acrylic acid or maleic acid, and as a dispersant for a graft polymer having polyvinylpyrrolidone as a basic polymer. There is no disclosure regarding the use of.
【０００６】また、特開平２０００−１７８３２３号公
報には、ポリビニルピロリドンに対してアクリル酸およ
びアクリル酸エステルをグラフト重合させてなるグラフ
ト重合体が開示されている。Further, Japanese Patent Application Laid-Open No. 2000-178323 discloses a graft polymer obtained by graft-polymerizing acrylic acid and acrylic ester to polyvinylpyrrolidone.
【０００７】しかしながら、該グラフト重合体において
は、微視的に観察すればアクリル酸がポリビニルピロリ
ドンにグラフト重合した形態が存在していると考えられ
るが、アクリル酸モノマーに加えてアクリル酸エステル
系モノマーをラジカル重合することを必須としており、
ポリビニルピロリドンにアクリル酸のみがラジカル重合
したグラフト重合体とは別物質である。しかも、該グラ
フト重合体はヘアコスメティック用の被膜形成剤、すな
わち毛髪固定剤として用いられた際のグラフトポリマー
自体の耐久性を目的としたものであり、グラフト重合体
の分散剤としての使用に関しては何ら開示されていな
い。However, in the graft polymer, microscopically, it is considered that acrylic acid is graft-polymerized with polyvinylpyrrolidone. However, in addition to the acrylic acid monomer, an acrylic acid ester monomer is used. Radical polymerization is essential,
It is a different substance from the graft polymer obtained by radical polymerization of polyvinyl pyrrolidone only with acrylic acid. Moreover, the graft polymer is intended for the durability of the graft polymer itself when used as a film-forming agent for hair cosmetics, that is, as a hair fixative, and regarding the use of the graft polymer as a dispersant. No disclosure is made.
【０００８】[0008]
【発明が解決しようとする課題】上記事項に鑑み、本発
明は、環境安定性および製膜性に優れた微粒子分散組成
物を提供することを目的とする。SUMMARY OF THE INVENTION In view of the above matters, an object of the present invention is to provide a fine particle dispersion composition excellent in environmental stability and film-forming property.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、Ｎ−ビニ
ル環状ラクタム構造を有するポリマーの品質向上を目的
として鋭意検討した結果、ポリビニルピロリドンに対し
てアクリル酸またはアクリル酸塩をグラフト重合させて
なるグラフト重合体を分散剤として用いた場合に、優れ
た環境安定性および製膜性が発現することを見出し、本
発明を完成するに至った。Means for Solving the Problems As a result of intensive studies aimed at improving the quality of a polymer having an N-vinyl cyclic lactam structure, the present inventors have found that acrylic acid or an acrylic acid salt is graft-polymerized onto polyvinylpyrrolidone. It was found that excellent environmental stability and film-forming properties are exhibited when the graft polymer obtained from the above is used as a dispersant, and the present invention has been completed.
【００１０】即ち本発明は、ポリビニルピロリドンに対
してアクリル酸またはアクリル酸塩がグラフト重合され
てなるグラフト重合体を分散剤として用い、微粒子を極
性溶媒中に分散させてなる微粒子分散組成物である。That is, the present invention is a fine particle dispersion composition in which fine particles are dispersed in a polar solvent by using a graft polymer obtained by graft polymerization of polyvinyl pyrrolidone with acrylic acid or an acrylic acid salt as a dispersant. .
【００１１】ここで、前記微粒子はカーボンブラックで
あることが好ましい。Here, the fine particles are preferably carbon black.
【００１２】また、微粒子分散組成物は、さらにポリア
ミド酸を含んでなることが好ましい。The fine particle dispersion composition preferably further contains a polyamic acid.
【００１３】[0013]
【発明の実施の形態】本発明は、ポリビニルピロリドン
（以下「ＰＶＰ」とも略記）に対してアクリル酸または
アクリル酸塩がグラフト重合されてなるグラフト重合体
を分散剤として用い、微粒子を極性溶媒中に分散させて
なる微粒子分散組成物である。BEST MODE FOR CARRYING OUT THE INVENTION The present invention uses, as a dispersant, a graft polymer obtained by graft-polymerizing polyvinylpyrrolidone (hereinafter abbreviated as “PVP”) with acrylic acid or an acrylic acid salt, and using fine particles in a polar solvent. It is a fine particle dispersed composition dispersed in
【００１４】ＰＶＰは特に限定されるものではないが、
重量平均分子量が低すぎると微粒子の分散安定性が低下
する恐れがある。この観点からは、重量平均分子量は１
０００以上であることが好ましく、２０００以上である
ことがより好ましく、１００００以上であることが特に
好ましい。一方、高すぎると微粒子分散剤の粘度が高く
なり取扱い上の不便が生じる恐れがある。この観点から
は、重量平均分子量は３００００００以下であることが
好ましく、２００００００以下であることがより好まし
く、５０００００以下であることが特に好ましい。ＰＶ
Ｐは各種公知の方法によって合成してもよく、各種市販
のものを用いてもよい。用いられるＰＶＰは本発明の効
果が制限されない程度の不純物を含んでいてもよいが、
不純物は少ない方が好ましい。The PVP is not particularly limited,
If the weight average molecular weight is too low, the dispersion stability of the fine particles may decrease. From this viewpoint, the weight average molecular weight is 1
It is preferably 000 or more, more preferably 2,000 or more, and particularly preferably 10,000 or more. On the other hand, if it is too high, the viscosity of the fine particle dispersant becomes high, which may cause inconvenience in handling. From this viewpoint, the weight average molecular weight is preferably 3,000,000 or less, more preferably 2,000,000 or less, and particularly preferably 500000 or less. PV
P may be synthesized by various known methods, or various commercially available products may be used. The PVP used may contain impurities to the extent that the effect of the present invention is not limited,
It is preferable that the amount of impurities is small.
【００１５】ＰＶＰには、アクリル酸またはこの塩がグ
ラフト単量体として付加され、ＰＶＰグラフト重合体と
される。塩としては、ナトリウム塩、カリウム塩、リチ
ウム塩、アンモニウム塩、有機アミン塩等が挙げられ
る。Acrylic acid or a salt thereof is added to PVP as a graft monomer to obtain a PVP graft polymer. Examples of the salt include sodium salt, potassium salt, lithium salt, ammonium salt, organic amine salt and the like.
【００１６】以下、ＰＶＰグラフト重合体の合成方法の
一実施形態について説明する。An embodiment of a method for synthesizing a PVP graft polymer will be described below.
【００１７】まず、溶媒中に、基幹ポリマーであるＰＶ
Ｐを添加する。ＰＶＰは逐次添加してもよいが、反応時
間の短縮や、生産性を考慮すると初期に一括して添加す
ることが好ましい。溶媒は、ＰＶＰが溶解するものであ
れば特に限定されるものではなく、例えば、水、アルコ
ール、エーテル、ケトン、エステル、アミド、スルホキ
シド等が挙げられる。これら溶媒中にはカルボン酸の中
和や、ｐＨ制御の目的で有機アミン類やアンモニア等を
添加してもよい。また、水を含む溶媒においてはアルカ
リ金属水酸化物を使用することも可能である。ＰＶＰの
添加量は特に限定されるものではないが、溶液中のＰＶ
Ｐ濃度を１０質量％以上とすることが好ましい。１０質
量％以上の高濃度で溶解させることにより、グラフト重
合させる時のグラフト効率を劇的に高めることができ、
生成物中の不純物含有量を低減することができるからで
ある。具体的にはグラフト鎖として導入されていないグ
ラフト単量体からなる不純物ポリマーの含有量は、グラ
フト鎖質量に対して４０質量％以下であることが好まし
い。不純物ポリマーの含有量が、グラフト鎖質量に対し
て４０質量％を超えるとグラフト重合体の環境安定性が
低下する恐れがあるからである。First, PV, which is a basic polymer, is added to a solvent.
Add P. PVP may be added sequentially, but it is preferable to add them all at once in consideration of shortening the reaction time and productivity. The solvent is not particularly limited as long as it can dissolve PVP, and examples thereof include water, alcohols, ethers, ketones, esters, amides, and sulfoxides. Organic amines, ammonia, etc. may be added to these solvents for the purpose of neutralizing the carboxylic acid and controlling the pH. Further, it is also possible to use an alkali metal hydroxide in the solvent containing water. The amount of PVP added is not particularly limited, but PV in the solution is not limited.
The P concentration is preferably 10% by mass or more. By dissolving at a high concentration of 10% by mass or more, the graft efficiency at the time of graft polymerization can be dramatically increased,
This is because the content of impurities in the product can be reduced. Specifically, the content of the impurity polymer composed of the graft monomer not introduced as the graft chain is preferably 40% by mass or less based on the mass of the graft chain. This is because if the content of the impurity polymer exceeds 40% by mass with respect to the mass of the graft chain, the environmental stability of the graft polymer may decrease.
【００１８】溶媒中にＰＶＰを加え、溶液を撹拌して均
一化した後、上述のグラフト単量体成分および重合開示
剤を加える。グラフト単量体成分の添加方法は特に限定
されるものではないが、グラフト効率および反応制御を
考慮すると、逐次添加することが好ましい。ＰＶＰに対
してグラフト重合される、アクリル酸等のグラフト単量
体の量は、本発明に係る効果が得られるのであれば特に
限定されるものではないが、少なすぎると好適な分散性
が発現されない恐れがある。このため、ＰＶＰ質量に対
して２質量％以上グラフト重合されることが好ましい。
一方、グラフト重合されすぎると基幹ポリマーであるＰ
ＶＰの特性発現が抑制される恐れがある。このため、Ｐ
ＶＰ質量に対して２００質量％以下グラフト重合される
ことが好ましく、１００質量％以下がより好ましい。従
って、ＰＶＰに対して２〜２００質量％のグラフト単量
体を添加することが好ましい。After PVP is added to the solvent and the solution is stirred to homogenize it, the above-mentioned graft monomer component and polymerization disclosing agent are added. The method of adding the graft monomer component is not particularly limited, but it is preferable to add them sequentially in consideration of graft efficiency and reaction control. The amount of the graft monomer such as acrylic acid that is graft-polymerized with respect to PVP is not particularly limited as long as the effects of the present invention can be obtained, but if it is too small, suitable dispersibility is expressed. There is a fear that it will not be done. Therefore, it is preferable that 2% by mass or more of the PVP is graft-polymerized.
On the other hand, if the graft polymerization is excessive, P, which is the basic polymer,
There is a possibility that the expression of VP characteristics may be suppressed. Therefore, P
Graft polymerization is preferably 200% by mass or less, more preferably 100% by mass or less, based on the VP mass. Therefore, it is preferable to add 2 to 200 mass% of the graft monomer to PVP.
【００１９】重合開始剤としてはラジカル開始剤を用い
ることができ、加熱等によってラジカルが発生するもの
であれば特に限定されるものではない。具体的には、過
硫酸アンモニウム、過硫酸ナトリウム、過硫酸カリウム
等の過硫酸塩；過酸化水素；メチルエチルケトンパーオ
キサイド、シクロヘキサノンパーオキサイド等のケトン
パーオキサイド類；ｔ−ブチルハイドロパーオキサイ
ド、クメンハイドロパーオキサイド等のハイドロパーオ
キサイド類；ジ−ｔ−ブチルパーオキサイド、ｔ−ブチ
ルクミルパーオキサイド等のジアルキルパーオキサイド
類；ｔ−ブチルパーオキシアセテート、ｔ−ブチルパー
オキシラウレート等のパーオキシエステル類；ｎ−ブチ
ル−４，４−ビス（ｔ−ブチルパーオキシ）パレエート
等のパーオキシケタール類；ジベンゾイルパーオキサイ
ド等のジアシルパーオキサイド類；等が挙げられる。こ
れらは、１種を単独で用いてもよいし、２種以上を併用
してもよい。また、上記過酸化物系開始剤と還元剤とを
併用するレドックス系開始剤を用いてもよい。このとき
用いることができる還元剤としては、鉄（II）塩、亜ジ
チオン酸ナトリウム、亜硫酸水素ナトリウム、亜硫酸ナ
トリウム等が挙げられる。開始剤の使用量は、グラフト
単量体に対して０．１〜１００ｍｏｌ％であることが好
ましく、１〜２０ｍｏｌ％であることがより好ましい。
添加方法についても特に限定されるものではないが、残
留モノマーの低減のためには数回〜数十回に分けて逐次
添加することが好ましい。A radical initiator can be used as the polymerization initiator, and is not particularly limited as long as radicals are generated by heating or the like. Specifically, persulfates such as ammonium persulfate, sodium persulfate and potassium persulfate; hydrogen peroxide; ketone peroxides such as methyl ethyl ketone peroxide and cyclohexanone peroxide; t-butyl hydroperoxide, cumene hydroperoxide. And the like; dialkyl peroxides such as di-t-butylperoxide and t-butylcumyl peroxide; peroxyesters such as t-butylperoxyacetate and t-butylperoxylaurate; n -Butyl-4,4-bis (t-butylperoxy) paleate and other peroxyketals; dibenzoyl peroxide and other diacyl peroxides; and the like. These may be used alone or in combination of two or more. In addition, a redox initiator that uses the peroxide initiator and a reducing agent together may be used. Examples of the reducing agent that can be used at this time include iron (II) salts, sodium dithionite, sodium hydrogen sulfite, sodium sulfite, and the like. The amount of the initiator used is preferably 0.1 to 100 mol% with respect to the graft monomer, and more preferably 1 to 20 mol%.
The addition method is also not particularly limited, but it is preferable to add them several times to several tens of times in order to reduce the residual monomer.
【００２０】上記グラフト単量体および開始剤を添加し
た後、数十分〜数時間反応温度を維持することにより反
応を完結させることができる。After adding the above-mentioned graft monomer and initiator, the reaction can be completed by maintaining the reaction temperature for several tens of minutes to several hours.
【００２１】グラフト単量体の重合方法、反応温度、反
応圧力については特に限定されるものではなく、一般的
な重合条件を用いることができる。具体的には、重合方
法としては溶液重合、乳化重合、懸濁重合、沈殿重合等
が挙げられる。反応温度は、０〜２００℃、好ましくは
５０〜１５０℃とするのがよい。反応圧力は常圧下、減
圧下、加圧下のいずれで反応させてもよく、効果的な除
熱のためには常圧下または減圧下で溶媒を沸騰させなが
ら反応させるとよい。反応雰囲気に関しては、窒素ガ
ス、アルゴンガス、二酸化炭素ガス等の不活性ガス雰囲
気下とするのがよい。The method of polymerizing the graft monomer, the reaction temperature and the reaction pressure are not particularly limited, and general polymerization conditions can be used. Specific examples of the polymerization method include solution polymerization, emulsion polymerization, suspension polymerization, and precipitation polymerization. The reaction temperature is 0 to 200 ° C, preferably 50 to 150 ° C. The reaction pressure may be normal pressure, reduced pressure, or increased pressure. For effective heat removal, the reaction may be performed while boiling the solvent under normal pressure or reduced pressure. The reaction atmosphere is preferably an inert gas atmosphere such as nitrogen gas, argon gas or carbon dioxide gas.
【００２２】得られたＰＶＰグラフト重合体は、極性溶
媒中において微粒子分散に用いられる。このとき分散さ
れる微粒子としては、絶縁性微粒子、半導電性微粒子、
導電性微粒子を用いることができる。これらの微粒子分
散方法としては、各種公知の分散技術を用いることがで
き、ビーズミル、ボールミル、ロールミル、バスケット
タイプミル、超音波分散、高圧分散などが挙げられる。The PVP graft polymer obtained is used for dispersing fine particles in a polar solvent. The fine particles dispersed at this time include insulating fine particles, semiconductive fine particles,
Conductive fine particles can be used. As a method for dispersing these fine particles, various known dispersion techniques can be used, and examples thereof include a bead mill, a ball mill, a roll mill, a basket type mill, ultrasonic dispersion, and high pressure dispersion.
【００２３】絶縁性微粒子としては、シリカ、アルミ
ナ、ジルコニア、チタニア、酸化マグネシウム、炭酸マ
グネシウム、炭酸カルシウム、硫酸カルシウム、硫酸バ
リウム、酸化アルミニウム等が挙げられる。Examples of the insulating fine particles include silica, alumina, zirconia, titania, magnesium oxide, magnesium carbonate, calcium carbonate, calcium sulfate, barium sulfate and aluminum oxide.
【００２４】半導電性微粒子としては、鉄窒化物、酸化
クロム、酸化亜鉛、チタンブラック、チタンイエロー、
コバルトブルー等の複合酸化物微粒子が挙げられる。The semiconductive fine particles include iron nitride, chromium oxide, zinc oxide, titanium black, titanium yellow,
Examples include complex oxide fine particles such as cobalt blue.
【００２５】導電性微粒子としては、カーボンブラッ
ク、黒鉛、金、銀、白金、アルミニウム、チタン、バナ
ジウム、クロム、マンガン、鉄、コバルト、ニッケル、
亜鉛、タングステン、ゲルマニウム、パラジウム、酸化
鉄、酸化ルテニウム、酸化モリブデン、フタロシアニン
ブルー、フタロシアニングリーンなどが挙げられる。The conductive fine particles include carbon black, graphite, gold, silver, platinum, aluminum, titanium, vanadium, chromium, manganese, iron, cobalt, nickel,
Examples thereof include zinc, tungsten, germanium, palladium, iron oxide, ruthenium oxide, molybdenum oxide, phthalocyanine blue, and phthalocyanine green.
【００２６】上記微粒子の他にも必要に応じて例えば、
有機シラン、顔料、充填剤、摩滅剤、誘電体、潤滑剤等
の各種公知の添加物微粒子を本発明の効果が損なわれな
い範囲で加えることができる。また、有機顔料、無機顔
料、カーボンブラック、金属粒子などの表面をシリカ、
アルミナ、ジルコニア、チタニア等で表面処理した微粒
子の分散にも有効である。In addition to the above fine particles, if necessary, for example,
Fine particles of various known additives such as organic silanes, pigments, fillers, abrasives, dielectrics and lubricants can be added within a range that does not impair the effects of the present invention. In addition, the surface of organic pigments, inorganic pigments, carbon black, metal particles, etc. is silica,
It is also effective for dispersing fine particles surface-treated with alumina, zirconia, titania or the like.
【００２７】微粒子の大きさは使用用途によって適宜選
択すればよく、特に限定されるものではない。例えば、
各種導電材料に使用する場合においては、電気特性のば
らつきを制御するためには、一次粒子に基づく平均粒径
が１μｍ以下であることが好ましく、０．００１〜０．
５μｍであることが好ましい。The size of the fine particles may be appropriately selected depending on the intended use and is not particularly limited. For example,
When used in various conductive materials, the average particle diameter based on the primary particles is preferably 1 μm or less in order to control variations in electrical characteristics, and 0.001 to 0.
It is preferably 5 μm.
【００２８】微粒子をＰＶＰに分散させて微粒子分散組
成物（微粒子分散液）を製造する際には、まずＰＶＰを
極性溶媒に溶解させた後、これに微粒子を添加・分散さ
せて微粒子分散組成物を調製することが好ましい。ま
た、微粒子の分散は、加熱しながら行うことが好まし
い。具体的には、室温以上、溶媒の沸点以下で分散させ
ることが好ましく、４０〜２００℃程度が適切である。
ＰＶＰが微粒子と反応可能な官能基を有している場合、
この加熱により微粒子の官能基とＰＶＰの官能基との反
応が進行し、微粒子の再凝集を抑制することができる。
即ち、粘度や電気抵抗率の経時変化を抑制でき、微粒子
分散組成物を適用した各種用途における環境安定性を向
上させることができる。なお機構は定かではないが、微
粒子がカーボンブラックである場合には、カーボンブラ
ックが反応可能な官能基を有さなくてもこの効果が得ら
れる。例えば一定の電気抵抗率を保持することが求めら
れる材料にカーボンブラックを含む微粒子分散組成物を
適用した場合には、好適に周辺環境に対する安定性を向
上させることができ、長期使用による劣化を抑制でき
る。When the fine particles are dispersed in PVP to produce a fine particle dispersion composition (fine particle dispersion liquid), PVP is first dissolved in a polar solvent, and then the fine particles are added / dispersed to the fine particle dispersion composition. Is preferably prepared. Further, it is preferable to disperse the fine particles while heating. Specifically, it is preferable to disperse at room temperature or higher and not higher than the boiling point of the solvent, and about 40 to 200 ° C. is suitable.
When PVP has a functional group capable of reacting with fine particles,
By this heating, the reaction between the functional group of the fine particles and the functional group of PVP proceeds, and the reaggregation of the fine particles can be suppressed.
That is, it is possible to suppress changes in viscosity and electric resistivity with time, and to improve environmental stability in various applications to which the fine particle dispersion composition is applied. Although the mechanism is not clear, when the fine particles are carbon black, this effect can be obtained even if the carbon black does not have a reactive functional group. For example, when a fine particle dispersion composition containing carbon black is applied to a material that is required to maintain a certain electric resistivity, stability to the surrounding environment can be improved, and deterioration due to long-term use can be suppressed. it can.
【００２９】極性溶媒中にＰＶＰグラフト重合体および
微粒子が含まれる場合の組成としては、微粒子分散組成
物全質量に対して、微粒子量が１〜５０質量％、ＰＶＰ
量が０．１〜３０質量％であることが好ましく、微粒子
量が５〜３０質量％、ＰＶＰ量が１〜２０質量％である
ことがより好ましい。When the PVP graft polymer and the fine particles are contained in the polar solvent, the amount of the fine particles is 1 to 50% by mass based on the total mass of the fine particle dispersion composition.
The amount is preferably 0.1 to 30% by mass, more preferably 5 to 30% by mass of fine particles and 1 to 20% by mass of PVP.
【００３０】極性溶媒としては、水性溶媒および有機溶
媒の双方を用いることができ、水性溶媒の例としては、
水、メタノール、エタノール、ｎ−プロパノール、ｉ−
プロパノール、ｎ−ブタノール、ｉ−ブタノール、ｔ−
ブタノール、グリセリン、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、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、へキシレングリコール等が挙げられる。有
機溶媒としては、Ｎ−メチル−２−ピロリドン、Ｎ，Ｎ
−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミ
ド、Ｎ，Ｎ−ジエチルホルムアミド、Ｎ，Ｎ−ジエチル
アセトアミド、Ｎ，Ｎ−ジメチルメトキシアセトアミ
ド、ジメチルホルムアミド、ジメチルスルホキシド、ヘ
キサメチルホスホルトリアミド、ピリジン、ジメチルス
ルホキシド、テトラメチレンスルホン、ジメチルテトラ
メチレンスルホン等が挙げられる。これらは単独で使用
してもよいし、互いに溶解するのであれば併用してもよ
い。有機溶媒にはクレゾール、フェノール、ベンゾニト
リル、ジオキサン、ブチロラクトン、キシレン、シクロ
ヘキサン、ヘキサン、ベンゼン、トルエン等を混合する
こともできる。ただし、ポリアミド酸をさらに含む微粒
子分散組成物においては、ポリイミド酸が加水分解して
低分子量化する恐れがあるため、極性溶媒として水を使
用する場合にはこの点に留意する必要がある。As the polar solvent, both an aqueous solvent and an organic solvent can be used, and examples of the aqueous solvent include:
Water, methanol, ethanol, n-propanol, i-
Propanol, n-butanol, i-butanol, t-
Examples thereof include butanol, glycerin, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol and hexylene glycol. As the organic solvent, N-methyl-2-pyrrolidone, N, N
-Dimethylformamide, N, N-dimethylacetamide, N, N-diethylformamide, N, N-diethylacetamide, N, N-dimethylmethoxyacetamide, dimethylformamide, dimethylsulfoxide, hexamethylphosphortriamide, pyridine, dimethylsulfoxide, Examples thereof include tetramethylene sulfone and dimethyl tetramethylene sulfone. These may be used alone or in combination as long as they dissolve each other. The organic solvent may be mixed with cresol, phenol, benzonitrile, dioxane, butyrolactone, xylene, cyclohexane, hexane, benzene, toluene and the like. However, in a fine particle dispersion composition further containing a polyamic acid, the polyimide acid may be hydrolyzed to lower the molecular weight, and therefore it is necessary to pay attention to this point when water is used as the polar solvent.
【００３１】本発明に係る微粒子分散組成物には、さら
にポリアミド酸が含まれてなることが好ましい。ポリア
ミド酸としては、特に制限されるべきものではなく、従
来公知のポリアミド酸を使用でき、市販のものも使用で
きる。ポリアミド酸の中では、下記式（１）：The fine particle dispersion composition according to the present invention preferably further contains a polyamic acid. The polyamic acid is not particularly limited, and conventionally known polyamic acids can be used, and commercially available products can also be used. Among the polyamic acids, the following formula (1):
【００３２】[0032]
【化１】 [Chemical 1]
【００３３】で表されるポリアミド酸が含まれることが
好ましい。ポリアミド酸はホモポリマーであっても、コ
ポリマー、ターポリマー等であってもよい。It is preferable that the polyamic acid represented by The polyamic acid may be a homopolymer, a copolymer, a terpolymer or the like.
【００３４】式（１）中のＲ1は少なくとも２個の炭素
原子を有する３価または４価の有機基である。耐熱性を
考慮すると環状炭化水素、芳香族環または芳香族複素環
を含有し、かつ、炭素数６〜３０であることが好まし
い。具体的には、ベンゼン、ビフェニル、ｏ−ターフェ
ニル、ｍ−ターフェニル、ｐ−ターフェニル、ナフタレ
ン、ペリレン、ジフェニルエーテル、ジフェニルスルホ
ン、ジフェニルプロパン、ベンゾフェノン、ビフェニル
トリフルオロプロパン、シクロブタン、シクロペンタン
に由来する３価または４価の有機基が挙げられる。R 1 in the formula (1) is a trivalent or tetravalent organic group having at least 2 carbon atoms. In consideration of heat resistance, it is preferable that the cyclic hydrocarbon, the aromatic ring or the aromatic heterocycle is contained and the carbon number is 6 to 30. Specifically, it is derived from benzene, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthalene, perylene, diphenyl ether, diphenyl sulfone, diphenyl propane, benzophenone, biphenyl trifluoropropane, cyclobutane, cyclopentane. Trivalent or tetravalent organic groups may be mentioned.
【００３５】式（１）中のＲ2は少なくとも２個の炭素
原子を有する２価の有機基である。耐熱性を考慮する
と、環状炭化水素、芳香族環または芳香族複素環を含有
し、かつ、炭素数６〜３０であることが好ましい。具体
的には、フェニル、ビフェニル、ターフェニル、ナフタ
レン、ペリレン、ジフェニルエーテル、ジフェニルスル
ホン、ジフェニルプロパン、ベンゾフェノン、ビフェニ
ルトリフルオロプロパン、ジフェニルメタン、ジシクロ
ヘキシルメタンなどの基が挙げられる。R 2 in the formula (1) is a divalent organic group having at least 2 carbon atoms. In consideration of heat resistance, it is preferable that the cyclic hydrocarbon, the aromatic ring or the aromatic heterocycle is contained and the carbon number is 6 to 30. Specific examples include groups such as phenyl, biphenyl, terphenyl, naphthalene, perylene, diphenyl ether, diphenyl sulfone, diphenylpropane, benzophenone, biphenyltrifluoropropane, diphenylmethane and dicyclohexylmethane.
【００３６】ｍは１または２であり、加熱後にポリイミ
ドとなるポリアミド酸（ｍ＝１）の具体例としては、ピ
ロメリット酸二無水物と４，４’−ジアミノジフェニル
エーテル、３，３’，４，４’−ベンゾフェノンテトラ
カルボン酸二無水物と４，４’−ジアミノジフェニルエ
ーテル、３，３’，４，４’−ビフェニルテトラカルボ
ン酸二無水物と４，４’−ジアミノジフェニルエーテル
などから合成されたポリアミド酸が挙げられる。また、
加熱後にポリアミドイミドとなるポリアミド酸（ｍ＝
２）は、例えば、上記のモノマーと類似の構造をもつト
リカルボン酸誘導体とジアミン、テトラカルボン酸二無
水物とジカルボン酸誘導体とジアミン、トリメリット酸
無水物とジイソシアネートとから得ることができる。M is 1 or 2, and specific examples of the polyamic acid (m = 1) which becomes a polyimide after heating include pyromellitic dianhydride and 4,4'-diaminodiphenyl ether, 3,3 ', 4. , 4'-benzophenone tetracarboxylic dianhydride and 4,4'-diaminodiphenyl ether, 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride and 4,4'-diaminodiphenyl ether Polyamic acid may be mentioned. Also,
Polyamic acid that becomes polyamide-imide after heating (m =
2) can be obtained, for example, from a tricarboxylic acid derivative and a diamine, a tetracarboxylic dianhydride and a dicarboxylic acid derivative and a diamine, and a trimellitic anhydride and a diisocyanate, which have a structure similar to that of the above-mentioned monomer.
【００３７】上記式（１）で表されるポリアミド酸を、
例えば目的物上に製膜後、１８０〜３５０℃程度に加熱
することによって、環境安定性に優れたポリイミド系樹
脂（ポリイミド、ポリイミドアミド）を得ることができ
る。ポリイミド系樹脂は耐熱性、機械特性、耐薬品性、
耐放射線性などに優れた樹脂であり、ポリイミド系樹脂
に微粒子を添加することによって各種特性の向上が図ら
れていたが、従来技術においては、ポリイミド系樹脂と
微粒子との親和性が低いため、微粒子の凝集が問題とな
っていた。この点、本発明に係るＰＶＰグラフト重合体
を用いた場合には、ＰＶＰグラフト重合体の優れた分散
性によって、合成されるポリイミド系樹脂と微粒子との
親和性を向上させることができ、環境安定性が向上す
る。ポリアミド酸の含有量は、本発明の効果を損なうこ
となく、かつ、ポリアミド酸含有による効果を有効に発
現させることができる範囲内であれば特に限定されるも
のではないが、微粒子分散組成物全量に対して、１〜５
０質量％含まれることが好ましく、５〜３０質量％含ま
れることがより好ましい。尚、ポリアミド酸が含まれる
場合の組成としては、また、本発明に係る微粒子分散組
成物における、微粒子とポリアミド酸との質量比（微粒
子：ポリアミド酸）は、１００：１〜１：１００である
ことが好ましく、１０：１〜１：１０であることがより
好ましい。The polyamic acid represented by the above formula (1) is
For example, a polyimide resin (polyimide, polyimide amide) having excellent environmental stability can be obtained by forming a film on an object and then heating the film to about 180 to 350 ° C. Polyimide resin has heat resistance, mechanical properties, chemical resistance,
It is a resin excellent in radiation resistance, etc., and was improved in various characteristics by adding fine particles to the polyimide resin, but in the prior art, since the affinity between the polyimide resin and the fine particles is low, Agglomeration of fine particles was a problem. In this respect, when the PVP graft polymer according to the present invention is used, the affinity between the polyimide resin to be synthesized and the fine particles can be improved due to the excellent dispersibility of the PVP graft polymer, and the environmental stability is improved. The property is improved. The content of the polyamic acid is not particularly limited as long as it does not impair the effect of the present invention, and is within the range in which the effect of the polyamic acid content can be effectively expressed, but the total amount of the fine particle dispersion composition For 1-5
The content is preferably 0% by mass, more preferably 5 to 30% by mass. In addition, as a composition when a polyamic acid is contained, the mass ratio of fine particles to polyamic acid (fine particles: polyamic acid) in the fine particle dispersion composition of the present invention is 100: 1 to 1: 100. It is preferable and it is more preferable that it is 10: 1 to 1:10.
【００３８】微粒子分散組成物（特に、ポリアミドを含
む微粒子分散組成物）の具体的な用途としては以下の用
途が挙げられる。即ち、導電性用途としては、複写機や
プリンターの帯電防止コーティング剤、電荷保持体、ト
ナー転写用部材、定着ベルト、中間転写ベルト、被膜型
抵抗体、導電ペースト、電池用電極材料、帯電防止性樹
脂、コンデンサ用導電性接着層、導電性摺動部材、回路
基板用基材、耐熱半導電性材料、自己温度制御通電発熱
体、サーマルヘッド用発熱抵抗体、記録用通電発熱シー
ト、電線ケーブルの被覆体、面状発熱体などが挙げられ
る。電磁波吸収用途としては、電磁波遮蔽シート、フレ
キシブル配線シート、電磁波吸収シート、熱線吸収シー
ト、紫外線吸収シートなどが挙げられる。遮光用途とし
ては、紫外線遮光性材料、カラーフィルター用ブラック
マトリックスなどが挙げられる。摺動用途として、低騒
音歯車の表面処理剤、摩擦材用成型体などが挙げられ
る。その他にも、太陽電池用基板、光センサー用基板、
光スイッチ用基板等の光変換装置の基板、プリント配線
用基板、サーマルヘッド基板などの電子機器の基板、イ
ンクジェットインクなど種々の用途に適用できるもので
あり、上記用途に限定されるものではない。The specific uses of the fine particle dispersion composition (particularly, the fine particle dispersion composition containing polyamide) are as follows. That is, as conductive uses, antistatic coating agents for copying machines and printers, charge carriers, toner transfer members, fixing belts, intermediate transfer belts, film type resistors, conductive pastes, battery electrode materials, antistatic properties. Resin, conductive adhesive layer for capacitors, conductive sliding member, substrate for circuit board, heat-resistant semi-conductive material, self-temperature controlled energization heating element, heating resistor for thermal head, recording energization heating sheet, wire cable Examples thereof include a coated body and a sheet heating element. Examples of applications for electromagnetic wave absorption include electromagnetic wave shielding sheets, flexible wiring sheets, electromagnetic wave absorbing sheets, heat ray absorbing sheets, and ultraviolet ray absorbing sheets. Examples of light-shielding uses include ultraviolet light-shielding materials and black matrices for color filters. Examples of sliding applications include surface treatment agents for low-noise gears and molded products for friction materials. In addition, solar cell substrates, photosensor substrates,
The present invention can be applied to various applications such as a substrate for an optical conversion device such as a substrate for an optical switch, a substrate for a printed wiring, a substrate for an electronic device such as a thermal head substrate, and an inkjet ink, and is not limited to the above applications.
【００３９】以下、本発明の効果を、プリンターの中間
転写ベルトに適用した場合を例にとり説明する。The effects of the present invention will be described below by taking the case of being applied to an intermediate transfer belt of a printer as an example.
【００４０】装置寿命の向上などを目的として、プリン
ターには感光ドラム等の像担持体にトナー等の記録剤に
よって形成された像を、一端中間転写ベルトに転写し、
それを印刷シート上に定着させる方式が考案されてい
る。この中間転写ベルトとしてポリイミド系樹脂を用い
た場合、強度、耐摩擦性、耐磨耗性を向上させることが
でき、ベルトにクラックが発生したり、駆動時の負荷で
変形して転写画像が歪んだりする問題を克服することが
できる。しかしながら、温度や湿度等の外部環境の変化
や長期間使用による劣化によって、電気抵抗率が大きく
変動し、転写される像が不鮮明になる問題があった。こ
の点本発明に係る微粒子分散組成物を用いて中間転写ベ
ルトを作製した場合には、上述したように環境安定性に
優れるものが得られるため、外部環境が変動した場合
や、長期間使用した場合であっても、中間転写ベルト表
面の電気抵抗率の変動を抑制することができる。その結
果、転写画像に生じる歪みを抑制でき、ひいてはプリン
ターの耐久性や、品質向上にも寄与するものとなる。ま
た、本発明に係る微粒子分散組成物は、製膜性に優れた
ものとなり、製膜後の剥離や亀裂などが生じにくいもの
となる。以上、プリンターの中間転写ベルトに適用した
場合について例示したが、本発明の効果は他の用途に適
用した場合も得られることは勿論である。For the purpose of improving the life of the apparatus, an image formed by a recording material such as toner on an image bearing member such as a photosensitive drum is transferred to the intermediate transfer belt in the printer.
A method of fixing it on a printing sheet has been devised. When a polyimide resin is used for this intermediate transfer belt, the strength, abrasion resistance, and abrasion resistance can be improved, and the transfer image is distorted due to cracks in the belt or deformation due to the load during driving. You can overcome the problems of drooling. However, there is a problem that the transferred image becomes unclear due to a large change in electrical resistivity due to changes in the external environment such as temperature and humidity and deterioration due to long-term use. In this respect, when an intermediate transfer belt is produced by using the fine particle dispersion composition according to the present invention, it is possible to obtain the one excellent in environmental stability as described above. Even in this case, it is possible to suppress the fluctuation of the electrical resistivity of the surface of the intermediate transfer belt. As a result, distortion that occurs in the transferred image can be suppressed, which in turn contributes to the durability and quality of the printer. Further, the fine particle-dispersed composition according to the present invention has excellent film-forming properties and is less likely to cause peeling or cracks after film-forming. The case where the invention is applied to the intermediate transfer belt of the printer has been described above, but it goes without saying that the effects of the present invention can be obtained when applied to other applications.
【００４１】次にポリアミド酸の合成方法の一実施形態
について説明する。ポリアミド酸は、テトラカルボン酸
二無水物またはその誘導体と、ジアミンとを反応させる
ことによって得ることができる。Next, one embodiment of a method for synthesizing a polyamic acid will be described. Polyamic acid can be obtained by reacting tetracarboxylic dianhydride or its derivative with diamine.
【００４２】テトラカルボン酸二無水物としては、ピロ
メリット酸二無水物、３，３’，４，４’−ベンゾフェ
ノンテトラカルボン酸二無水物、３，３’，４，４’−
ビフェニルテトラカルボン酸二無水物、２，３，３’，
４−ビフェニルテトラカルボン酸二無水物、２，３，
６，７−ナフタレンテトラカルボン酸二無水物、１，
２，５，６−ナフタレンテトラカルボン酸二無水物、
１，４，５，８−ナフタレンテトラカルボン酸二無水
物、２，２’−ビス（３，４−ジカルボキシフェニル）
プロパン二無水物、ビス（３，４−ジカルボキシフェニ
ル）スルホン二無水物、ペリレン−３，４，９，１０−
テトラカルボン酸二無水物、ビス（３，４−ジカルボキ
シフェニル）エーテル二無水物、エチレンテトラカルボ
ン酸二無水物等が挙げられる。As the tetracarboxylic dianhydride, pyromellitic dianhydride, 3,3 ', 4,4'-benzophenone tetracarboxylic dianhydride, 3,3', 4,4'-
Biphenyltetracarboxylic dianhydride, 2,3,3 ',
4-biphenyltetracarboxylic dianhydride, 2,3
6,7-naphthalenetetracarboxylic dianhydride, 1,
2,5,6-naphthalenetetracarboxylic dianhydride,
1,4,5,8-naphthalenetetracarboxylic dianhydride, 2,2'-bis (3,4-dicarboxyphenyl)
Propane dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, perylene-3,4,9,10-
Examples thereof include tetracarboxylic dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, and ethylenetetracarboxylic dianhydride.
【００４３】一方ジアミンの例としては、４，４’−ジ
アミノジフェニルエーテル、４，４’−ジアミノジフェ
ニルメタン、３，３’−ジアミノジフェニルメタン、
３，３’−ジクロロベンジジン、４，４−ジアミノジフ
ェニルスルフィド−３，３’−ジアミノジフェニルスル
ホン、１，５−ジアミノナフタレン、ｍ−フェニレンジ
アミン、ｐ−フェニレンジアミン、３，３’−ジメチル
−４，４’−ビフェニルジアミン、ベンジジン、３，
３’−ジメチルベンジジン、３，３’−ジメトキシベン
ジジン、４，４’−ジアミノフェニルスルホン、４，
４’−ジアミノフェニルスルホン、４，４’−ジアミノ
ジフェニルスルフィド、４，４’−ジアミノジフェニル
プロパン、２，４−ビス（β−アミノ−第三ブチル）ト
ルエン、ビス（ｐ−β−アミノ−第三ブチルフェニル）
エーテル、ビス（ｐ−β−メチル−δ−アミノフェニ
ル）ベンゼン、ビス−ｐ−（１，１−ジメチル−５−ア
ミノ−ペンチル）ベンゼン、１−イソプロピル−２，４
−ｍ−フェニレンジアミン、ｍ−キシリレンジアミン、
ｐ−キシリレンジアミン、ジ（ｐ−アミノシクロヘキシ
ル）メタン、ヘキサメチレンジアミン、ヘプタメチレン
ジアミン、オクタメチレンジアミン、ノナメチレンジア
ミン、デカメチレンジアミン、ジアミノプロピルテトラ
メチレン、３−メチルヘプタメチレンジアミン、４，４
−ジメチルヘプタメチレンジアミン、２，１１−ジアミ
ノドデカン、１，２−ビス−３−アミノプロポキシエタ
ン、２，２−ジメチルプロピレンジアミン、３−メトキ
シヘキサメチレンジアミン、２，５−ジメチルヘキサメ
チレンジアミン、２，５−ジメチルヘプタメチレンジア
ミン、２，５−ジメチルヘプタメチレンジアミン、３−
メチルヘプタメチレンジアミン、５−メチルノナメチレ
ンジアミン、２，１１−ジアミノドデカン、２，１７−
ジアミノエイコサデカン、１，４−ジアミノシクロヘキ
サン、１，１０−ジアミノ−１，１０−ジメチルデカ
ン、１，１２−ジアミノオクタデカン、２，２−ビス
〔４−（４−アミノフェノキシ）フェニル〕プロパン、
ピペラジン、Ｈ2Ｎ（ＣＨ2）3Ｏ（ＣＨ2）2Ｏ（ＣＨ2）
ＮＨ2、Ｈ2Ｎ（ＣＨ2）3Ｓ（ＣＨ2）3ＮＨ2、Ｈ2Ｎ（Ｃ
Ｈ2）3Ｎ（ＣＨ3）2（ＣＨ2）3ＮＨ2等が挙げられる。On the other hand, examples of the diamine include 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane,
3,3′-dichlorobenzidine, 4,4-diaminodiphenyl sulfide-3,3′-diaminodiphenyl sulfone, 1,5-diaminonaphthalene, m-phenylenediamine, p-phenylenediamine, 3,3′-dimethyl-4 , 4'-biphenyldiamine, benzidine, 3,
3'-dimethylbenzidine, 3,3'-dimethoxybenzidine, 4,4'-diaminophenyl sulfone, 4,
4'-diaminophenyl sulfone, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl propane, 2,4-bis (β-amino-tert-butyl) toluene, bis (p-β-amino-secondary Tributylphenyl)
Ether, bis (p-β-methyl-δ-aminophenyl) benzene, bis-p- (1,1-dimethyl-5-amino-pentyl) benzene, 1-isopropyl-2,4
-M-phenylenediamine, m-xylylenediamine,
p-xylylenediamine, di (p-aminocyclohexyl) methane, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, diaminopropyltetramethylene, 3-methylheptamethylenediamine, 4,4
-Dimethylheptamethylenediamine, 2,11-diaminododecane, 1,2-bis-3-aminopropoxyethane, 2,2-dimethylpropylenediamine, 3-methoxyhexamethylenediamine, 2,5-dimethylhexamethylenediamine, 2 , 5-dimethylheptamethylenediamine, 2,5-dimethylheptamethylenediamine, 3-
Methylheptamethylenediamine, 5-methylnonamethylenediamine, 2,11-diaminododecane, 2,17-
Diaminoeicosadecane, 1,4-diaminocyclohexane, 1,10-diamino-1,10-dimethyldecane, 1,12-diaminooctadecane, 2,2-bis [4- (4-aminophenoxy) phenyl] propane,
Piperazine, H 2 N (CH 2) 3 O (CH 2) 2 O (CH 2)
NH 2, H 2 N (CH 2) 3 S (CH 2) 3 NH 2, H 2 N (C
H 2) 3 N (CH 3 ) 2 (CH 2) 3 NH 2 and the like.
【００４４】テトラカルボン酸二無水物とジアミンと
は、極性溶媒中で重合させることができ、これらが溶解
し得るのであれば、ＰＶＰおよび微粒子が含まれる極性
溶媒中において合成することも可能である。しかしなが
ら、上述したように水の存在下においてはポリイミド酸
が加水分解して低分子量化するため、極性溶媒として水
を使用する場合にはこの点に留意する必要がある。重合
したポリアミド酸と微粒子が分散されたＰＶＰグラフト
重合体とを混合してもよい。なお、重合時に使用される
テトラカルボン酸二無水物とジアミンとの濃度は、ポリ
アミド酸の含有量が上記記載した範囲に含まれるように
適宜設定すればよく、特に限定されるものではないが５
〜３０質量％であることが好ましい。反応は８０℃以下
の温度で、０．５〜１０時間程度反応させることが一般
的である。The tetracarboxylic dianhydride and diamine can be polymerized in a polar solvent, and if they can be dissolved, they can also be synthesized in a polar solvent containing PVP and fine particles. . However, as described above, in the presence of water, the polyimide acid is hydrolyzed to have a low molecular weight, and therefore it is necessary to pay attention to this point when water is used as the polar solvent. The polymerized polyamic acid and the PVP graft polymer in which the fine particles are dispersed may be mixed. The concentrations of the tetracarboxylic acid dianhydride and the diamine used during the polymerization may be appropriately set so that the polyamic acid content falls within the range described above, and are not particularly limited.
It is preferably ˜30% by mass. The reaction is generally carried out at a temperature of 80 ° C. or lower for about 0.5 to 10 hours.
【００４５】[0045]
【実施例】以下、本発明にかかる実施例および比較例に
ついて記載するが、本発明は下記実施例に限定されるも
のでないことは勿論である。なお、測定方法は以下の通
りである。EXAMPLES Examples and comparative examples according to the present invention will be described below, but it goes without saying that the present invention is not limited to the following examples. The measuring method is as follows.
【００４６】１．Ｋ値
ポリビニルピロリドンを水に１質量％の濃度で溶解さ
せ、その溶液の粘度を２５℃において毛細管粘度計によ
って測定し、この測定値を用いて下記式（２）：1. K value Polyvinylpyrrolidone was dissolved in water at a concentration of 1% by mass, and the viscosity of the solution was measured at 25 ° C. by a capillary viscometer. Using this measured value, the following formula (2):
【００４７】[0047]
【数１】 [Equation 1]
【００４８】（式中、ηrelは溶媒に対する溶液の粘度
を表し、Ｃは溶液１００ｍｌ中のポリビニルピロリドン
の質量（ｇ）を表し、Ｋ＝１０００Ｋ0である）で表さ
れるフィケンチャー式から求めた。(Wherein η rel represents the viscosity of the solution with respect to the solvent, C represents the mass (g) of polyvinylpyrrolidone in 100 ml of the solution, and K = 1000K 0 ). .
【００４９】２．粘度 Ｂ型粘度計を用いて２５℃で測定した。2. viscosity It measured at 25 degreeC using the Brookfield viscometer.
【００５０】３．塗膜強度 鉛筆（Ｈ）で引き掻いた後の様子を目視で確認した。3. Coating strength The state after scratching with a pencil (H) was visually confirmed.
【００５１】＜合成例１＞温度計、撹拌機、滴下ロート
および冷却管を備えた２００ｍｌセパラブルフラスコ
に、ポリビニルピロリドン（Ｋ値３０；３８．９ｇ）お
よび蒸留水（３８．９ｇ）を仕込み、フラスコ内部を窒
素置換した後、撹拌溶解して均一溶液とした。その後、
さらに、この溶液が還流状態となるまで昇温した。フラ
スコ内温は１０３℃であった。Synthesis Example 1 A 200 ml separable flask equipped with a thermometer, a stirrer, a dropping funnel and a condenser was charged with polyvinylpyrrolidone (K value 30; 38.9 g) and distilled water (38.9 g). After substituting the inside of the flask with nitrogen, the flask was dissolved with stirring to obtain a uniform solution. afterwards,
Furthermore, the temperature was raised until the solution reached a reflux state. The temperature inside the flask was 103 ° C.
【００５２】次いで、このフラスコ内に、３７％アクリ
ル酸ナトリウム水溶液（３８．１ｇ；アクリル酸ナトリ
ウム１５０ｍｍｏｌ）を９０分かけて滴下し、滴下中
に、重合開始剤として１５％過硫酸ナトリウム水溶液
（１１．９ｇ；過硫酸ナトリウム７．５ｍｍｏｌ）を１
０回に分けて添加した。Then, a 37% sodium acrylate aqueous solution (38.1 g; sodium acrylate 150 mmol) was dropped into this flask over 90 minutes, and during the dropping, a 15% sodium persulfate aqueous solution (11 1.9 g; sodium persulfate 7.5 mmol) 1
It was added in batches of 0.
【００５３】アクリル酸ナトリウム水溶液滴下終了後、
引き続き同温度で２時間熟成を行なった。熟成中に、さ
らに１５％過硫酸ナトリウム水溶液（２．４ｇ；過硫酸
ナトリウム１．５ｍｍｏｌ）を２回に分けて添加した。
反応開始から終了までの間、反応液は均一であり、不溶
物の生成はなかった。反応後、反応液中のアクリル酸ナ
トリウムモノマーの残存量を液体クロマトグラフィーに
て分析したことろ、固形分に対して０．１質量％以下と
なっていた。After the dropping of the aqueous solution of sodium acrylate,
Then, aging was carried out at the same temperature for 2 hours. During the aging, 15% aqueous sodium persulfate solution (2.4 g; sodium persulfate 1.5 mmol) was further added in two portions.
From the start to the end of the reaction, the reaction solution was uniform and no insoluble matter was formed. After the reaction, the residual amount of the sodium acrylate monomer in the reaction liquid was analyzed by liquid chromatography to find that it was 0.1% by mass or less based on the solid content.
【００５４】得られたポリマー水溶液について、キャピ
ラリー電気泳動分析装置（ミリポリ株式会社製、Ｗａｔ
ｅｒｓＱｕａｎｔａ４０００）を用いて組成分析を行っ
た。その結果、アクリル酸ナトリウムホモポリマーの量
は、固形分に対して０質量％であった。The obtained aqueous polymer solution was analyzed by a capillary electrophoresis analyzer (Wat manufactured by Millipoly Co., Ltd.).
ersQuanta 4000) was used for composition analysis. As a result, the amount of sodium acrylate homopolymer was 0% by mass based on the solid content.
【００５５】以上の結果より、得られたポリマーは、基
幹ポリマーであるビニルピロリドンに、アクリル酸ナト
リウムからなるグラフト鎖が導入されたグラフト重合体
であり、原料ＰＶＰ質量に対して、グラフト鎖導入量が
３６質量％、グラフト重合体中のアクリル酸ナトリウム
ホモポリマーの含有量が０質量％であることが判った。
このグラフト重合体水溶液を重合体水溶液（１）とす
る。重合体水溶液（１）の固形分は４２質量％であっ
た。From the above results, the obtained polymer is a graft polymer in which a graft chain composed of sodium acrylate is introduced into vinylpyrrolidone which is a basic polymer, and the amount of the graft chain introduced is based on the mass of the raw material PVP. Was 36% by mass, and the content of the sodium acrylate homopolymer in the graft polymer was 0% by mass.
This graft polymer aqueous solution is referred to as a polymer aqueous solution (1). The solid content of the polymer aqueous solution (1) was 42% by mass.
【００５６】＜合成例２＞合成例１で得られた重合体水
溶液（１）に対して減圧乾燥を実施し、水分がほとんど
除去されたグラフト重合体を得た。これを、グラフト重
合体（２）とする。<Synthesis Example 2> The aqueous polymer solution (1) obtained in Synthesis Example 1 was dried under reduced pressure to obtain a graft polymer from which most of the water was removed. This is designated as a graft polymer (2).
【００５７】＜合成例３＞温度計、撹拌機、滴下ロート
および冷却管を備えた２００ｍｌセパラブルフラスコ
に、ポリビニルピロリドン（Ｋ値１５；２２．２ｇ）お
よび蒸留水（５．６ｇ）を仕込み、フラスコ内部を窒素
置換した後、撹拌溶解して均一溶液とした。その後、さ
らに、この溶液が還流状態となるまで昇温した。フラス
コ内温は１０３℃であった。<Synthesis Example 3> Polyvinylpyrrolidone (K value 15; 22.2 g) and distilled water (5.6 g) were charged in a 200 ml separable flask equipped with a thermometer, a stirrer, a dropping funnel and a condenser. After substituting the inside of the flask with nitrogen, the flask was dissolved with stirring to obtain a uniform solution. After that, the temperature was further raised until the solution reached a reflux state. The temperature inside the flask was 103 ° C.
【００５８】次いで、このフラスコ内に、３７％アクリ
ル酸ナトリウム水溶液（５０．８ｇ；アクリル酸ナトリ
ウム２００ｍｍｏｌ）を９０分かけて滴下し、滴下中
に、重合開始剤として１５％過硫酸ナトリウム水溶液
（１５．９ｇ；過硫酸ナトリウム１０．０ｍｍｏｌ）を
１０回に分けて添加した。Then, a 37% sodium acrylate aqueous solution (50.8 g; sodium acrylate 200 mmol) was dropped into the flask over 90 minutes, and a 15% sodium persulfate aqueous solution (15% as a polymerization initiator (15 1.9 g; sodium persulfate 10.0 mmol) was added in 10 batches.
【００５９】アクリル酸ナトリウム水溶液滴下終了後、
引き続き同温度で２時間熟成を行なった。熟成中に、さ
らに１５％過硫酸ナトリウム水溶液（３．２ｇ；過硫酸
ナトリウム２．０ｍｍｏｌ）を２回に分けて添加した。
反応開始から終了までの間、反応液は均一であり、不溶
物の生成はなかった。反応後、反応液中のアクリル酸ナ
トリウムモノマーの残存量を液体クロマトグラフィーに
て分析したことろ、固形分に対して０．１質量％以下と
なっていた。After the completion of dropping the aqueous solution of sodium acrylate,
Then, aging was carried out at the same temperature for 2 hours. During the aging, 15% aqueous sodium persulfate solution (3.2 g; sodium persulfate 2.0 mmol) was further added in two portions.
From the start to the end of the reaction, the reaction solution was uniform and no insoluble matter was formed. After the reaction, the residual amount of the sodium acrylate monomer in the reaction liquid was analyzed by liquid chromatography to find that it was 0.1% by mass or less based on the solid content.
【００６０】得られたポリマー水溶液について、キャピ
ラリー電気泳動分析装置（ミリポリ株式会社製、Ｗａｔ
ｅｒｓＱｕａｎｔａ４０００）を用いて組成分析を行っ
た。その結果、アクリル酸ナトリウムホモポリマーの量
は、固形分に対して１３質量％であった。The obtained polymer aqueous solution was analyzed by a capillary electrophoresis analyzer (Wat manufactured by Millipoly Co., Ltd.).
ersQuanta 4000) was used for composition analysis. As a result, the amount of sodium acrylate homopolymer was 13% by mass based on the solid content.
【００６１】以上の結果より、得られたポリマーは、基
幹ポリマーであるビニルピロリドンに、アクリル酸ナト
リウムからなるグラフト鎖が導入されたグラフト重合体
であり、原料ＰＶＰ質量に対して、グラフト鎖導入量が
７５質量％、グラフト重合体中のアクリル酸ナトリウム
ホモポリマーの含有量が１３質量％であることが判っ
た。このグラフト重合体水溶液を重合体水溶液（３）と
する。重合体水溶液（３）の固形分は４５質量％であっ
た。From the above results, the obtained polymer is a graft polymer in which a graft chain consisting of sodium acrylate is introduced into the basic polymer vinylpyrrolidone, and the amount of the graft chain introduced is based on the mass of the raw material PVP. Was 75% by mass, and the content of the sodium acrylate homopolymer in the graft polymer was 13% by mass. This graft polymer aqueous solution is referred to as a polymer aqueous solution (3). The solid content of the polymer aqueous solution (3) was 45% by mass.
【００６２】＜合成例４＞ピロメリット酸二無水物（２
１．８１質量部）と、４，４’−ジアミノジフェニルメ
タン（１９．８３質量部）を、Ｎ−メチル−２−ピロリ
ドン（１６６．５６質量部）中において、常温で３時間
重縮合反応させ、固形分２０質量％のポリアミド酸のワ
ニス（２０８．２質量部）を得た。<Synthesis Example 4> Pyromellitic dianhydride (2
1.81 parts by mass) and 4,4′-diaminodiphenylmethane (19.83 parts by mass) in N-methyl-2-pyrrolidone (166.56 parts by mass) at room temperature for 3 hours for polycondensation reaction, A polyamic acid varnish (208.2 parts by mass) having a solid content of 20% by mass was obtained.
【００６３】＜実施例１＞温度計、撹拌機、滴下ロート
および冷却管を備えたセパラブルフラスコに、合成例１
で得られた重合体水溶液（１）（２８．５７ｇ）および
水（９１．４３ｇ）を加え、さらにカーボンブラック
（三菱化学株式会社製ＭＡ１００Ｒ株式会社製；３０
ｇ）を加えた後、ジルコニア製ビーズ（８００ｇ）を投
入し、７００ｒｐｍで撹拌しながら１００℃で１時間、
続いて５０℃で１時間分散を行ない、ビーズを分離し、
カーボンブラック分散液を得た。得られたカーボンブラ
ック分散液の環境安定性を評価するために、粘度および
その経時変化を調査した。結果を表１に示す。Example 1 A synthetic example 1 was placed in a separable flask equipped with a thermometer, a stirrer, a dropping funnel, and a cooling tube.
The polymer aqueous solution (1) (28.57 g) and water (91.43 g) obtained in Step 3 were added, and carbon black (Mitsubishi Chemical Co., Ltd., MA100R Co., Ltd .; 30) was added.
g), zirconia beads (800 g) were added, and the mixture was stirred at 700 rpm at 100 ° C. for 1 hour.
Then, disperse at 50 ° C. for 1 hour to separate the beads,
A carbon black dispersion was obtained. To evaluate the environmental stability of the resulting carbon black dispersion, the viscosity and its change with time were investigated. The results are shown in Table 1.
【００６４】＜比較例１＞温度計、撹拌機、滴下ロート
および冷却管を備えたセパラブルフラスコに、ポリビニ
ルピロリドン（和光純薬工業株式会社製；Ｋ値３０；６
ｇ）および水（２２．５７ｇ）を加え、さらにカーボン
ブラック（三菱化学株式会社製ＭＡ１００Ｒ；３０ｇ）
を加えた後、ジルコニア製ビーズ（８００ｇ）を投入
し、７００ｒｐｍで撹拌しながら１００℃で１時間、続
いて５０℃で１時間分散を行ない、ビーズを分離し、カ
ーボンブラック分散液を得た。得られたカーボンブラッ
ク分散液の環境安定性を評価するために、粘度およびそ
の経時変化を調査した。結果を表１に示す。Comparative Example 1 Polyvinylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd .; K value: 30; 6) was placed in a separable flask equipped with a thermometer, a stirrer, a dropping funnel and a cooling tube.
g) and water (22.57 g) were added, and carbon black (MA100R manufactured by Mitsubishi Chemical Corporation; 30 g) was further added.
Then, beads made of zirconia (800 g) were added, and the mixture was dispersed at 100 ° C. for 1 hour with stirring at 700 rpm and then at 50 ° C. for 1 hour to separate the beads to obtain a carbon black dispersion liquid. To evaluate the environmental stability of the resulting carbon black dispersion, the viscosity and its change with time were investigated. The results are shown in Table 1.
【００６５】[0065]
【表１】 [Table 1]
【００６６】表１に示すように、本発明の微粒子分散組
成物は、経時変化に伴う組成物の劣化が生じにくく、種
々の製品に適用したときに優れた性能を発現しうること
が示された。As shown in Table 1, it is shown that the fine particle dispersion composition of the present invention hardly causes deterioration of the composition with the passage of time, and can exhibit excellent performance when applied to various products. It was
【００６７】＜実施例２＞温度計、撹拌機、滴下ロート
および冷却管を備えたセパラブルフラスコに、合成例２
で得られたグラフト重合体（２）（６ｇ）、Ｎ−メチル
−２−ピロリドン（和光純薬工業株式会社製；１２９
ｇ）およびカーボンブラック（三菱化学株式会社製ＭＡ
１００Ｒ１５ｇ）を加えた後、ジルコニア製ビーズ（８
００ｇ）を投入し、７００ｒｐｍで撹拌しながら１００
℃で１時間、続いて５０℃で１時間分散を行ない、ビー
ズを分離し、カーボンブラック分散液を得た。得られた
分散液（１００質量部）に合成例４で合成したワニス
（７０質量部）を添加し、スピンコートにより製膜、乾
燥、４００℃キュアを施し、塗膜強度を調べた。結果を
表２に示す。Example 2 A synthetic example 2 was placed in a separable flask equipped with a thermometer, a stirrer, a dropping funnel and a cooling tube.
Graft polymer (2) (6 g) obtained in 1., N-methyl-2-pyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd .; 129)
g) and carbon black (MA manufactured by Mitsubishi Chemical Corporation)
After adding 100R15g), beads made of zirconia (8
00g) and 100 with stirring at 700 rpm.
The beads were separated by performing dispersion at 1 ° C. for 1 hour and then at 50 ° C. for 1 hour to obtain a carbon black dispersion liquid. The varnish (70 parts by mass) synthesized in Synthesis Example 4 was added to the obtained dispersion liquid (100 parts by mass), spin coating was performed to form a film, drying and curing at 400 ° C., and the coating film strength was examined. The results are shown in Table 2.
【００６８】＜比較例２＞温度計、撹拌機、滴下ロート
および冷却管を備えたセパラブルフラスコに、ポリビニ
ルピロリドン（和光純薬工業株式会社製；Ｋ値３０；６
ｇ）、水（２２．５７ｇ）およびカーボンブラック（３
０ｇ）を加えた後、ジルコニア製ビーズ（８００ｇ）を
投入し、７００ｒｐｍで撹拌しながら１００℃で１時
間、続いて５０℃で１時間分散を行ない、ビーズを分離
し、カーボンブラック分散液を得た。得られた分散液
（１００質量部）に合成例４で合成したワニス（７０質
量部）を添加し、スピンコートにより製膜、乾燥、４０
０℃キュアを施し、塗膜強度を調べた。結果を表２に示
す。Comparative Example 2 Polyvinylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd .; K value: 30; 6) was placed in a separable flask equipped with a thermometer, a stirrer, a dropping funnel and a cooling tube.
g), water (22.57 g) and carbon black (3
0 g), zirconia beads (800 g) were added, and the mixture was dispersed at 100 ° C. for 1 hour with stirring at 700 rpm and then at 50 ° C. for 1 hour to separate the beads to obtain a carbon black dispersion. It was The varnish synthesized in Synthesis Example 4 (70 parts by mass) was added to the obtained dispersion liquid (100 parts by mass), and spin-coating was performed to form a film, followed by drying.
Curing was performed at 0 ° C. and the strength of the coating film was examined. The results are shown in Table 2.
【００６９】[0069]
【表２】 [Table 2]
【００７０】[0070]
【発明の効果】ポリビニルピロリドンを主幹ポリマーと
してアクリル酸やアクリル酸塩をグラフト重合させたグ
ラフト重合体を分散剤として用いることにより、周辺環
境に対する安定性や、長期使用による劣化を抑制でき
る。このため、本発明に係る微粒子分散組成物が適用さ
れた各種材料は、一定の遮光率、電気抵抗率、電磁波吸
収率等を発現することができ、製品品質の向上が実現で
きる。By using a graft polymer obtained by graft-polymerizing acrylic acid or an acrylic acid salt with polyvinylpyrrolidone as a main polymer as a dispersant, it is possible to suppress stability to the surrounding environment and suppress deterioration due to long-term use. Therefore, various materials to which the fine particle dispersion composition according to the present invention is applied can exhibit a certain light-shielding rate, electric resistivity, electromagnetic wave absorption rate, etc., and improvement of product quality can be realized.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 伊藤 広一 大阪府吹田市西御旅町５番８号 株式会社 日本触媒内 (72)発明者 池田 勇人 大阪府吹田市西御旅町５番８号 株式会社 日本触媒内 Ｆターム(参考） 4J002 BN201 CM042 DA026 DA036 DA076 DA086 DA096 DA106 DA116 DE076 DE096 DE106 DE116 DE136 DE146 DE236 DF016 DG046 DG056 DJ016 EU026 GH01 GM01 GQ02 HA08 4J026 AA61 BA25 DB02 DB03 DB04 DB14 DB15 DB16 GA01 ─────────────────────────────────────────────────── ─── Continued front page (72) Inventor Koichi Ito 5-8 Nishiomitabicho, Suita City, Osaka Prefecture Within Nippon Shokubai (72) Inventor Hayato Ikeda 5-8 Nishiomitabicho, Suita City, Osaka Prefecture Within Nippon Shokubai F-term (reference) 4J002 BN201 CM042 DA026 DA036 DA076 DA086 DA096 DA106 DA116 DE076 DE096 DE106 DE116 DE136 DE146 DE236 DF016 DG046 DG056 DJ016 EU026 GH01 GM01 GQ02 HA08 4J026 AA61 BA25 DB02 DB03 DB04 DB14 DB15 DB16 GA01
Claims (3)
酸またはアクリル酸塩がグラフト重合されてなるグラフ
ト重合体を分散剤として用い、微粒子を極性溶媒中に分
散させてなる微粒子分散組成物。1. A fine particle dispersion composition in which fine particles are dispersed in a polar solvent using a graft polymer obtained by graft-polymerizing acrylic acid or an acrylic acid salt with respect to polyvinylpyrrolidone as a dispersant.
とを特徴とする請求項１に記載の微粒子分散組成物。2. The fine particle dispersion composition according to claim 1, wherein the fine particles are carbon black.
特徴とする請求項１または２に記載の微粒子分散組成
物。3. The fine particle dispersion composition according to claim 1, further comprising a polyamic acid.
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| JP2005229109A (en) * | 2004-02-10 | 2005-08-25 | E I Du Pont De Nemours & Co | Thick-film ink composite possible to be printed in ink jet, and method therefor |
| WO2007037376A1 (en) * | 2005-09-30 | 2007-04-05 | Nippon Shokubai Co., Ltd. | Process for producing n-pyrrolidone graft polymer composition and n-pyrrolidone graft polymer composition |
| JP2008542448A (en) * | 2005-05-27 | 2008-11-27 | 株式会社日本触媒 | N-vinyl cyclic lactam polymer, its production method and use |
| US20150279505A1 (en) * | 2012-10-15 | 2015-10-01 | Dai Nippon Printing Co., Ltd. | Metal particle dispersion for electroconductive substrates, method for producing the same, and method for producing an electroconductive substrate |
| US20150299364A1 (en) * | 2012-10-18 | 2015-10-22 | Dai Nippon Printing Co., Ltd | Dispersant, metal particle dispersion for electroconductive substrates, and method for producing electroconductive substrate |
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