JP5332141B2 - ポリマーエマルジョン及びその製造法 - Google Patents
ポリマーエマルジョン及びその製造法 Download PDFInfo
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- JP5332141B2 JP5332141B2 JP2007168485A JP2007168485A JP5332141B2 JP 5332141 B2 JP5332141 B2 JP 5332141B2 JP 2007168485 A JP2007168485 A JP 2007168485A JP 2007168485 A JP2007168485 A JP 2007168485A JP 5332141 B2 JP5332141 B2 JP 5332141B2
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- 239000012986 chain transfer agent Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 1
- TWSCTWISFSVDKR-UHFFFAOYSA-N dichloromethane;1,1,2-trichloroethane Chemical compound ClCCl.ClCC(Cl)Cl TWSCTWISFSVDKR-UHFFFAOYSA-N 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- OWMBTIRJFMGPAC-UHFFFAOYSA-N dimethylamino 2-methylprop-2-enoate Chemical compound CN(C)OC(=O)C(C)=C OWMBTIRJFMGPAC-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229960002377 dixanthogen Drugs 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000011883 electrode binding agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AMFIBVNSEBYBAM-UHFFFAOYSA-N ethylcarbamothioylsulfanyl n-ethylcarbamodithioate Chemical compound CCNC(=S)SSC(=S)NCC AMFIBVNSEBYBAM-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000005817 fluorobutyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000013615 primer Substances 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- XJAJNAQBHCNNBM-UHFFFAOYSA-N sulfo hydrogen sulfate dihydrate Chemical compound O.O.OS(=O)(=O)OS(O)(=O)=O XJAJNAQBHCNNBM-UHFFFAOYSA-N 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Developing Agents For Electrophotography (AREA)
- Sealing Material Composition (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
(式中、Xはカルボキシル基又はその塩、Rはアルキル基、アリール基、置換アルキル基又は置換アリール基を表す。)
X−R−S−S−R−X (2)
(式中、Xはカルボキシル基又はその塩、Rはアルキル基、アリール基、置換アルキル基又は置換アリール基を表す。)
上記酸性基含有チオール化合物としては、チオグリコール酸、チオリンゴ酸、2−メルカプトプロピオン酸、3−メルカプトプロピオン酸、チオサリチル酸、3−メルカプト安息香酸、4−メルカプト安息香酸、チオマロン酸、ジチオコハク酸、チオマレイン酸、チオマレイン酸無水物、ジチオマレイン酸、チオグルタール酸、システイン、ホモシステイン、5−メルカプトテトラゾール酢酸、3−メルカプト−1−プロパンスルホン酸等が挙げられ、酸性基含有ジスルフィド化合物としては、2,2’−ジチオジプロピオン酸、3,3’−ジチオジプロピオン酸、4,4’−ジチオジブタン酸、2,2’−ジチオビス安息香酸、6,6’−ジチオジニコチン酸等が挙げられる。即ち、本発明の特徴の1つは、エマルジョンを構成するポリマーのベースになる疎水性モノマー及び酸性官能基含有モノマーとの共重合工程を必要としない点にある。
三方コックを備えた200mlガラスフラスコに、チオリンゴ酸5.28g、2,2‘−アゾビスイソブチロニトリル0.35g、ベンゼン0.50g及びアセトン50.00gを仕込んで溶解後、メタクリル酸メチル35.37gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱して重合し、末端酸性基含有ポリメタクリル酸メチルのアセトン溶液を得た。27時間後のメタクリル酸メチルの重合転化率は89.3%だった。
得られたポリメタクリル酸メチルエマルジョンの耐水性の判定は○、即ち、塗膜の白化及び水脹れは殆ど見られなかった。接着性,付着性評価の結果は100%、即ち、塗膜の剥離は見られなかった。
三方コックを備えた200mlガラスフラスコに、チオグリコール酸6.70g、4,4‘−アゾビス(4−シアノペンタン酸)0.35g、ベンゼン0.50g及びアセトン50.00gを仕込んで溶解後、メタクリル酸メチル35.37gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱して重合し、末端酸性基含有ポリメタクリル酸メチルのアセトン溶液を得た。27時間後のメタクリル酸メチルの重合転化率は90.5%だった。
得られたポリメタクリル酸メチルエマルジョンの耐水性の判定は○、即ち、塗膜の白化及び水脹れは殆ど見られなかった。接着性,付着性評価の結果は100%、即ち、塗膜の剥離は見られなかった。
三方コックを備えた200mlガラスフラスコに、2,2’-ジチオビス安息香酸9.00g、4,4‘−アゾビス(4−シアノペンタン酸)0.35g、ベンゼン0.50g及びテトラヒドロフラン50.00gを仕込んで溶解後、メタクリル酸メチル35.00gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱し、末端酸性基含有ポリメタクリル酸メチルのテトラヒドロフラン溶液を得た。27時間後のメタクリル酸メチルの重合転化率は92.0%だった。
得られたポリメタクリル酸メチルエマルジョンの耐水性の判定は○、即ち、塗膜の白化及び水脹れは殆ど見られなかった。接着性,付着性評価の結果は100%、即ち、塗膜の剥離は見られなかった。
三方コックを備えた200mlガラスフラスコに、チオリンゴ酸5.28g、4,4‘−アゾビス(4−シアノペンタン酸)0.69g、ベンゼン0.52g及びテトラヒドロフラン50.00gを仕込んで溶解後、メタクリル酸メチル25.00g、アクリル酸ブチル10.00gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱し、末端酸性基含有ポリメタクリル酸メチル/アクリル酸ブチル共重合体のアセトン溶液を得た。24時間後のメタクリル酸メチル及びアクリル酸ブチルの重合転化率は91.0%及び98.5%だった。
三方コックを備えた200mlガラスフラスコに、チオリンゴ酸7.00g、4,4‘−アゾビス(4−シアノペンタン酸)0.40g、ベンゼン0.52g及びアセトン50.00gを仕込んで溶解後、メタクリル酸メチル20.00g及びスチレン15.50を添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱し、末端酸性基含有ポリメタクリル酸メチル/スチレン共重合体のアセトン溶液を得た。65時間後のメタクリル酸メチル及びスチレンの重合転化率は95.6%及び65.2%だった。
攪拌機を備えた500ml耐圧容器にチオリンゴ酸10.60g及び4,4‘−アゾビス(4−シアノペンタン酸)0.70gを仕込んだ後、内部を窒素置換し、窒素雰囲気下、ベンゼン1.00g及びテトラヒドロフラン100.00gを仕込んで溶解後、スチレン20.60g及び1,3−ブタジエン51.40gを仕込んで攪拌を開始し、系内を70℃に昇温した。70℃で72時間重合し、末端酸性基含有ポリスチレン/1,3−ブタジエン共重合体のテトラヒドロフラン溶液を得た。72時間後のスチレン及重合転化率は75.4%、1,3−ブタジエンはほぼ100%消費されていた。
三方コックを備えた200mlガラスフラスコに、3,3‘−ジチオジプロピオン酸7.90g、4,4‘−アゾビス(4−シアノペンタン酸)0.35g、ベンゼン0.50g及びアセトン50.00gを仕込んで溶解後、メタクリル酸メチル35.00gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱し、末端酸性基含有ポリメタクリル酸メチルのアセトン溶液を得た。27時間後のメタクリル酸メチルの重合転化率は80.3%だった。
三方コックを備えた200mlガラスフラスコに、チオリンゴ酸4.00g、2,2‘−ジチオビス安息香酸2.00g、4,4‘−アゾビス(4−シアノペンタン酸)0.35g、ベンゼン0.50g及びアセトン50.00gを仕込んで溶解後、メタクリル酸メチル20.00g及びアクリル酸ブチル15.50gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱し、末端酸性基含有ポリメタクリル酸メチル/アクリルサンブチル共重合体のアセトン溶液を得た。27時間後のメタクリル酸メチル及びアクリル酸ブチルの重合転化率は88.6%及び97.2%だった。
三方コック及び冷却管を備えた300mlガラスフラスコに、チオリンゴ酸20.00g、4,4‘−アゾビス(4−シアノペンタン酸)0.70g、ベンゼン0.70g及びアセトン75.00gを仕込んで溶解後、スチレン35.00gを添加し、凍結−脱気−融解を2回繰返して十分脱気した後、窒素雰囲気下、マグネチックスターラーで攪拌しながら、65℃のオイルバスで加熱して重合し、末端酸性基含有ポリスチレンのアセトン溶液を得た。72時間後のスチレンの重合転化率は81.0%だった。
300mlガラスフラスコに、実施例9で合成した末端酸性基含有ポリスチレンのアセトン溶液3.00g、ベンゼン0.15g、及びジエチルアミノエタノール0.82g(上記溶液に含まれるカルボキシル基の1.02当量)を仕込んで混合後、攪拌下ゆっくり純水35.00gを添加し、混合した後、ロータリーエバポレーターでアセトンを留去した。三方コックを備えた200mlガラスフラスコに、上記の水溶液を移液し、スチレン30.00g、n−ドデシルメルカプタン0.10g及び3.40wt%過硫酸カリウム水溶液0.2mlを添加した(仕込モノマーに対する末端カルボキシル基含有ポリスチレンの添加量は約2.0wt%)。1L/分の流量で窒素を15分流して十分脱気した後、マグネチックスターラーで攪拌しながら、60℃のオイルバスで加熱を開始した。2時間毎に上記過硫酸カリウム水溶液を0.2ml添加しながら9時間重合した。スチレンの重合転化率は84.1%であり、塊状のスケールが発生した。エマルジョン部分を回収し、ロータリーエバポレーターで未反応モノマー、及び水分を留去し、ポリスチレンエマルジョンを得た(固形分45wt%)。平均粒径は176nmであり、500nm以上の大粒子も存在し、エマルジョン安定性は実施例よりも劣った。エマルジョン安定性が悪かったため、耐水性を評価するに値しなかった。
三方コックを備えた200mlガラスフラスコに、ドデシルベンゼンスルホン酸ナトリウム1.00g及び純水35.00gを仕込、溶解した後、メタクリル酸メチル28.00g、n−ドデシルメルカプタン0.10g及び3.40wt%過硫酸カリウム水溶液0.2mlを添加した。1L/分の流量で窒素を15分流して十分脱気した後、マグネチックスターラーで攪拌しながら、40℃のオイルバスで加熱を開始した。2時間毎に上記過硫酸カリウム水溶液を0.2ml添加しながら5時間重合した。メタクリル酸メチルの重合転化率は98.1%であり、スケールの発生は見られなかった。ロータリーエバポレーターで未反応モノマー、及び水分を留去し、ポリメタクリル酸メチルエマルジョンを得た(固形分45wt%、エマルジョン中のポリマーに対する従来型乳化剤の含量は約3.5wt%)。
三方コックを備えた200mlガラスフラスコに、実施例1で合成した末端酸性基含有ポリメタクリル酸メチルのアセトン溶液5.71g、ベンゼン0.15g、及びジエチルアミノエタノール0.54g(上記溶液に含まれるカルボキシル基の1.02当量)を仕込んだ後、攪拌下、ラウリル硫酸ナトリウム1.40wt%水溶液35.60gをゆっくり添加し、混合した。これに、メタクリル酸メチル28.00g、n−ドデシルメルカプタン0.10g及び3.40wt%過硫酸カリウム水溶液0.2mlを添加し、1L/分の流量で窒素を15分流して十分脱気した後、マグネチックスターラーで攪拌しながら、40℃のオイルバスで加熱を開始した。2時間毎に上記過硫酸カリウム水溶液を0.2ml添加しながら5時間重合した。メタクリル酸メチルの重合転化率は98.6%であり、スケールの発生は見られなかった。ロータリーエバポレーターで未反応モノマー、及び水分を留去し、ポリメタクリル酸メチルエマルジョンを得た(固形分45wt%、エマルジョン中のポリマーに対する従来型乳化剤の含量は約4.3wt%)。
Claims (5)
- 親水性溶剤の存在下、末端に酸性官能基を有する水不溶性ポリマーを用いてラジカル重合性モノマーを水中に乳化させ、ラジカル開始剤を加えて乳化重合するポリマーエマルジョンの製造法であって、該末端に酸性官能基を有する水不溶性ポリマーが、下記一般式(1)で表される酸性官能基含有チオール化合物、下記一般式(2)で表される酸性官能基含有ジスルフィド化合物、又は、下記一般式(1)で表される酸性官能基含有チオール化合物及び下記一般式(2)で表される酸性官能基含有ジスルフィド化合物の存在下で、ラジカル重合性モノマーをラジカル重合して得られた水不溶性ポリマーであることを特徴とする、末端に酸性官能基を有する水不溶性ポリマー、及び2wt%以下のアニオン性乳化剤、ノニオン性乳化剤、カチオン性乳化剤又は両性乳化剤を含有するポリマーエマルジョンの製造法。
H−S−R−X (1)
(式中、Xはカルボキシル基又はその塩、Rはアルキル基、アリール基、置換アルキル基又は置換アリール基を表す。)
X−R−S−S−R−X (2)
(式中、Xはカルボキシル基又はその塩、Rはアルキル基、アリール基、置換アルキル基又は置換アリール基を表す。) - 親水性溶剤が、アセトン、メチルエチルケトン、テトラヒドロフラン、イソプロパノール、メトキシエタノール、エタノール、メタノールから選択される少なくとも1種以上の溶剤であることを特徴とする請求項1に記載のポリマーエマルジョンの製造法。
- 末端に酸性官能基を有する水不溶性ポリマーのゲル浸透クロマトグラフィー(GPC)で求めた数平均分子量が500〜30000であることを特徴とする請求項1又は請求項2記載のポリマーエマルジョンの製造法。
- ラジカル重合性モノマーが、メタクリル酸エステル系モノマー、アクリル酸エステル系モノマー、スチレン系モノマー、1,3−ブタジエン系モノマーであることを特徴とする請求項1〜請求項3のいずれかの項に記載のポリマーエマルジョンの製造法。
- 請求項1〜請求項4のいずれかの項に記載のポリマーエマルジョンの製造法で得られたポリマーエマルジョンを含むことを特徴とする塗料、コーティング剤、バインダー、トナー、接着剤、プライマー、シーリング剤。
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