JP2012046727A - ポリビニルアセタール・ポリエステルグラフト共重合体および分散剤 - Google Patents
ポリビニルアセタール・ポリエステルグラフト共重合体および分散剤 Download PDFInfo
- Publication number
- JP2012046727A JP2012046727A JP2011125386A JP2011125386A JP2012046727A JP 2012046727 A JP2012046727 A JP 2012046727A JP 2011125386 A JP2011125386 A JP 2011125386A JP 2011125386 A JP2011125386 A JP 2011125386A JP 2012046727 A JP2012046727 A JP 2012046727A
- Authority
- JP
- Japan
- Prior art keywords
- polyvinyl acetal
- polyester
- dispersant
- acid
- graft copolymer
- 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
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- 229920000728 polyester Polymers 0.000 title claims abstract description 63
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title claims abstract description 44
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 42
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 39
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 28
- 239000007787 solid Substances 0.000 claims abstract description 51
- 239000002245 particle Substances 0.000 claims abstract description 43
- 239000006185 dispersion Substances 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 239000011342 resin composition Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000008199 coating composition Substances 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 24
- 239000000976 ink Substances 0.000 description 17
- -1 copying toners Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 150000001412 amines Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000003606 tin compounds Chemical class 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000002612 dispersion medium Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- ADKSBPBFSJYPDY-UHFFFAOYSA-N OCCCCOCCCCO.C(CCC)[Sn] Chemical compound OCCCCOCCCCO.C(CCC)[Sn] ADKSBPBFSJYPDY-UHFFFAOYSA-N 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- NXMOWTFIUDDXIT-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dioctyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCC(C)(C)C NXMOWTFIUDDXIT-UHFFFAOYSA-L 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
- 239000004632 polycaprolactone Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- 239000001119 stannous chloride Substances 0.000 description 4
- 235000011150 stannous chloride Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LBZZJNPUANNABV-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)phenyl]ethanol Chemical compound OCCC1=CC=C(CCO)C=C1 LBZZJNPUANNABV-UHFFFAOYSA-N 0.000 description 2
- ILRRKELLBSRKLA-UHFFFAOYSA-N 2-[6-(2-hydroxyethoxy)hexoxy]ethanol Chemical compound OCCOCCCCCCOCCO ILRRKELLBSRKLA-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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Landscapes
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- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
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Abstract
【解決手段】下記一般式(1)の構成単位、ビニルアルコール構成単位、ビニルエステル構成単位をそれぞれ1個以上有し、重量平均分子量が100〜100,000であるポリビニルアセタールと、重量平均分子量が100〜50,000であるポリエステルとを反応させて得られ、前記ポリビニルアセタールが有する水酸基の1〜95モル%が、ポリエステルとのエステル交換反応により結合を形成したポリビニルアセタール・ポリエステルグラフト共重合体を分散剤として用いる。
(ただし、R1、水素原子、あるいは炭素数1〜20の直鎖状若しくは分岐のアルキル基又はアリール基を表し、これらは置換基を有していてもよい。)
【選択図】なし
Description
本発明のポリビニルアセタール・ポリエステルグラフト共重合体は、ポリビニルアセタールとポリエステルとの反応生成物であり、ポリビニルアセタールが有する水酸基の1〜95モル%が、ポリエステルとのエステル交換反応により結合を形成しているものである。
上記した本発明のポリビニルアセタール・ポリエステルグラフト共重合体は、分散剤として好適に使用することができ、無機および有機の双方の固体粒子に対して有効である。具体的には、塗料、印刷インキ、複写用トナー、プラスチック、顔料捺染剤、インクジェット記録用インキ、熱転写記録用インキ、カラーフィルター用レジスト、筆記具用インキ等の各分野で通常用いられる分散媒体中に、高濃度かつ低粘度で安定に固体粒子を分散させることができる。
[製造例1:ポリエステルの合成]
窒素導入管、温度計、還流管を取り付けた反応容器に、メタノール10.0部、ε−カプロラクトン800.0部、テトラブチルチタネート0.1部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、残存するε−カプロラクトンが1%以下になるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は3100であった。
窒素導入管、温度計、還流管を取り付けた反応容器に、ジエチレングリコール50.0部、ε−カプロラクトン800.0部、テトラブチルチタネート0.1部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、残存するε−カプロラクトンが1%以下になるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は2000であった。
窒素導入管、温度計、還流管を取り付けた反応容器に、ジエチレングリコール10.0部、ε−カプロラクトン800.0部、テトラブチルチタネート0.1部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、残存するε−カプロラクトンが1%以下になるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は8,500であった。
窒素導入管、温度計、還流管を取り付けた反応容器に、2−ヒドロキシエチルメタクリレート100.0部、ε−カプロラクトン800.0部、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、残存するε−カプロラクトンが1%以下になるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は1,200であった。
窒素導入管、温度計、還流管、水分離器を取り付けた反応容器に、1,6−ヘキサンジオール400.0部、アジピン酸436.0部、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、酸価が1mgKOH/gになるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は4,200であった。
窒素導入管、温度計、還流管、水分離器を取り付けた反応容器に、12−ヒドロキシステアリン酸800.0部、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、酸価が 31mgKOH/gになるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は1,800であった。
窒素導入管、温度計、還流管、水分離器を取り付けた反応容器に、3−メチル−1,5−ペンタンジオール100.0部、アジピン酸109.0部、ε−カプロラクトン359.0部、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で160℃まで4時間かけて昇温し、酸価が1mgKOH/gになるまで160℃で加熱を行った。反応生成物は黄色固体で、重量平均分子量は12,500であった。
窒素導入管、温度計、還流管を取り付けた反応容器に、ポリビニルブチラール(商品名「エスレックBL−1」平均分子量約19,000、水酸基約36モル%、アセチル基3モル%以下、ブチラール化度63±3モル%、積水化学工業株式会社製)49.7部、製造例1で得られたポリエステル50.3部(4モル%/対水酸基)、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で200℃まで昇温し、6時間加熱を行った。反応生成物は黄色粘調液体で、重量平均分子量は67,500、ポリエステルの導入率は65.2%であった。分子量の測定及びポリエステル導入率の測定は下記方法に従った。
下記表1に示す配合および反応条件に従い、製造例8と同様にしてポリビニルブチラール・ポリエステルグラフトポリマーを製造し、分子量の測定及びポリエステル導入率の測定を行った。
窒素導入管、温度計、還流管、検水管を取り付けた反応容器に、ポリエチレンイミン(商品名「Lupasol PR8515」、重量平均分子量2000)8.1部、製造例1のポリエステル91.9部、テトラブチルチタネート0.05部を仕込み、窒素雰囲気下で200℃まで昇温し、6時間加熱を行った。
ポリビニルアセタール・ポリエステルグラフト共重合体の平均分子量は、テトラヒドロフランを溶媒に用いて、ゲルパーミエーションクロマトグラフィー(GPC)により測定した。
※2:商品名「プラクセルH1P」ダイセル化学工業株式会社製、ポリカプロラクトン、分子量10,000
※3:商品名「プラクセル240」ダイセル化学工業株式会社製、ポリカプロラクトンジオール、分子量4,000
※4:商品名「プラクセル230」ダイセル化学工業株式会社製、ポリカプロラクトンジオール、分子量3,000
<耐熱性試験>
上記製造例8〜28で得られたポリビニルアセタール・ポリエステルグラフト共重合体、及び比較製造例1で得られたポリエチレンイミン・ポリエステルグラフト共重合体等の耐熱性試験を以下の通り行った。結果を表2に示す。
○:色差(ΔE)0〜5、△:色差(ΔE)5〜10、×:色差(ΔE)10以上
※2:商品名「エスレックBL−1」、積水化学工業株式会社製、ポリビニルブチラール、重量平均分子量約19000、水酸基約36モル%、アセチル基3モル%以下、ブチラール化度63±3モル%
上記製造例により得られたポリビニルアセタール・ポリエステルグラフトポリマー、比較対象の分散剤を表3に示した分散媒に溶解し、表3に示した固体粒子、直径0.3mmのジルコニアビーズ(規格品)をそれぞれ加え、ペイントシェーカーを用いて4時間分散した。
上記分散終了直後に、分散性を目視にて観察し、以下の基準で評価した。結果を表3に示す。
◎:すべての粉末が液中に分散し、まったく底部に沈澱が発生していない。
○:ほとんどの粉末が液中に分散しているが、わずかに底部に沈澱が発生する。
△:半分程度の粉末が液中に沈澱する。
×:ほとんどの粉末が底部に沈澱する。
分散試験後の分散体10.0部にアクリル樹脂(商品名「アクリペットMD」、三菱レイヨン製)を0.4部添加し、攪拌して溶解させた。得られた混合液をガラス基板に平均膜厚が1.8μmになるようにスピンコートし、120℃のオーブンで1時間加熱した。得られた塗膜を目視にて観察し、以下の基準により評価した。結果を表3に示す。
○:得られた塗膜が透明である。
△:得られた塗膜に曇りが見られる。
×:粒子が凝集し、透明性がない。
塗膜状態試験で作製した試験板と、さらにそれを230℃で1時間加熱した試験板との色差を測定し、以下の基準により評価した。結果を表3に示す。
○:色差(ΔE)0〜1 △:色差(ΔE)1〜2.5 ×:色差(ΔE)2.5以上
メタクリル酸/ベンジルメタクリレート共重合体(25/75重量%比、重量平均分子量約30000)40.0部、ピグメントブルー15:6 23.0部、製造例7のポリビニルアセタール−ポリエステルのグラフト共重合物 7.0部、ジペンタエリスリトールヘキサアクリレート 10.0部、2,4−ビス(トリクロロメチル)−6−(2−エトキシスチリル)−s−トリアジン 3.0部、PGMEA 200部を混合し、0.3mmジルコニアビーズを加え、ペイントシェーカーにより分散を行った。
Claims (6)
- 下記一般式(1)〜(3)で表される構成単位をそれぞれ1個以上有し、重量平均分子量が100〜100,000であるポリビニルアセタールと、重量平均分子量が100〜50,000であるポリエステルとを反応させて得られ、
前記ポリビニルアセタールが有する水酸基の1〜95モル%が、前記ポリエステルとのエステル交換反応により結合を形成した
ことを特徴とするポリビニルアセタール・ポリエステルグラフト共重合体。
- 請求項1に記載のポリビニルアセタール・ポリエステルグラフト共重合体を含有してなる分散剤。
- 請求項2に記載の分散剤により固体粒子を非水系液体に分散させてなる固体粒子分散体。
- 塗料組成物又はインキ組成物であることを特徴とする、請求項3に記載の固体粒子分散体。
- 請求項2に記載の分散剤、樹脂及び固体粒子を含有してなる固体粒子含有樹脂組成物。
- 請求項2に記載の分散剤で処理したことを特徴とする表面処理固体粒子。
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JP2014079691A (ja) * | 2012-10-16 | 2014-05-08 | Dai Ichi Kogyo Seiyaku Co Ltd | 固体粒子分散剤、これを用いた固体粒子分散体及び表面処理固体粒子 |
JP2016124975A (ja) * | 2014-12-26 | 2016-07-11 | 花王株式会社 | 水系インク |
WO2024080375A1 (ja) * | 2022-10-14 | 2024-04-18 | 三菱鉛筆株式会社 | 非焼成鉛筆芯 |
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JPH0881547A (ja) * | 1994-09-12 | 1996-03-26 | Daicel Chem Ind Ltd | カルボキシル基含有ラクトン変性ポリビニルアセタ−ル樹脂、その製造方法および硬化性樹脂組成物 |
WO2011067889A1 (ja) * | 2009-12-04 | 2011-06-09 | 第一工業製薬株式会社 | ポリビニルアセタール・ポリエステルグラフト共重合体および分散剤 |
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JPH07238199A (ja) * | 1994-01-10 | 1995-09-12 | Daicel Chem Ind Ltd | 硬化性樹脂組成物 |
JPH0881547A (ja) * | 1994-09-12 | 1996-03-26 | Daicel Chem Ind Ltd | カルボキシル基含有ラクトン変性ポリビニルアセタ−ル樹脂、その製造方法および硬化性樹脂組成物 |
WO2011067889A1 (ja) * | 2009-12-04 | 2011-06-09 | 第一工業製薬株式会社 | ポリビニルアセタール・ポリエステルグラフト共重合体および分散剤 |
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JP2014079691A (ja) * | 2012-10-16 | 2014-05-08 | Dai Ichi Kogyo Seiyaku Co Ltd | 固体粒子分散剤、これを用いた固体粒子分散体及び表面処理固体粒子 |
JP2016124975A (ja) * | 2014-12-26 | 2016-07-11 | 花王株式会社 | 水系インク |
WO2024080375A1 (ja) * | 2022-10-14 | 2024-04-18 | 三菱鉛筆株式会社 | 非焼成鉛筆芯 |
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