JP7443741B2 - 触媒及び熱膨張剤を内包するポリビニル樹脂微粒子、該微粒子組成物、及びその製造方法 - Google Patents
触媒及び熱膨張剤を内包するポリビニル樹脂微粒子、該微粒子組成物、及びその製造方法 Download PDFInfo
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- JP7443741B2 JP7443741B2 JP2019226166A JP2019226166A JP7443741B2 JP 7443741 B2 JP7443741 B2 JP 7443741B2 JP 2019226166 A JP2019226166 A JP 2019226166A JP 2019226166 A JP2019226166 A JP 2019226166A JP 7443741 B2 JP7443741 B2 JP 7443741B2
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- polyvinyl resin
- fine particles
- resin fine
- meth
- catalyst
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- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-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
- KDUIUFJBNGTBMD-DLMDZQPMSA-N [8]annulene Chemical compound C/1=C/C=C\C=C/C=C\1 KDUIUFJBNGTBMD-DLMDZQPMSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- ROPXFXOUUANXRR-YPKPFQOOSA-N bis(2-ethylhexyl) (z)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-YPKPFQOOSA-N 0.000 description 1
- SFBXYJXNDOJHLL-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;sulfo hydrogen sulfate Chemical compound OS(=O)(=O)OS(O)(=O)=O.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 SFBXYJXNDOJHLL-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- RQTQBQMVIJMUPB-UHFFFAOYSA-N butan-1-ol titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO RQTQBQMVIJMUPB-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- MGFFVSDRCRVHLC-UHFFFAOYSA-N butyl 3-sulfanylpropanoate Chemical compound CCCCOC(=O)CCS MGFFVSDRCRVHLC-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 238000004132 cross linking Methods 0.000 description 1
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- 238000007607 die coating method Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
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- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 description 1
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- 229960000878 docusate sodium Drugs 0.000 description 1
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- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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- 238000002296 dynamic light scattering Methods 0.000 description 1
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- 238000005538 encapsulation Methods 0.000 description 1
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- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
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- UXYBXUYUKHUNOM-UHFFFAOYSA-M ethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(C)C UXYBXUYUKHUNOM-UHFFFAOYSA-M 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 229910052733 gallium Inorganic materials 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- 230000007062 hydrolysis Effects 0.000 description 1
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- 239000005453 ketone based solvent Substances 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
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- 239000000693 micelle Substances 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
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- MEIFYCBWNZYXKW-UHFFFAOYSA-N n-[1,5-dihydroxy-3-(hydroxymethyl)pentan-3-yl]-2-[[1-[[1,5-dihydroxy-3-(hydroxymethyl)pentan-3-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCC(CO)(CCO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CCO)CCO MEIFYCBWNZYXKW-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- KQJBQMSCFSJABN-UHFFFAOYSA-N octadecan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-] KQJBQMSCFSJABN-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 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
- RCMHUQGSSVZPDG-UHFFFAOYSA-N phenoxybenzene;phosphoric acid Chemical class OP(O)(O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 RCMHUQGSSVZPDG-UHFFFAOYSA-N 0.000 description 1
- FURYAADUZGZUGQ-UHFFFAOYSA-N phenoxybenzene;sulfuric acid Chemical class OS(O)(=O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 FURYAADUZGZUGQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LPBNNQBYFCZCTA-UHFFFAOYSA-N sulfuric acid;1-tridecoxytridecane Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCOCCCCCCCCCCCCC LPBNNQBYFCZCTA-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- VCZQFJFZMMALHB-UHFFFAOYSA-N tetraethylsilane Chemical compound CC[Si](CC)(CC)CC VCZQFJFZMMALHB-UHFFFAOYSA-N 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Colloid Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Description
エチレン誘導体類としては、例えばエチレンおよび酢酸ビニル、塩化ビニル、プロピレン、1,3-ブタジエン、1-ブテン、イソプレン、スチレン、1-ヘプテン、アクリロニトリル、アクロレイン、アクロレインジメチルアセタール等が挙げられる。
ビニルエーテル類としては、例えばメチルビニルエーテル、エチルビニルエーテル、プロピルビニルエーテル、イソプロピルビニルエーテル、ブチルビニルエーテル、イソブチルビニルエーテル、2-エチルへキシルビニルエーテル、シクロへキシルビニルエーテル、シクロヘキサンジメタノールジビニルエーテル、2-ヒドロキシエチルビニルエーテル、4-ヒドロキシブチルビニルエーテル、1,4-ブタンジオールビニルエーテル、シクロヘキサンジメタノールモノビニルエーテル、ジエチレングリコールモノビニルエーテル、ジエチレングリコールジビニルエーテル、トリエチレングリコールジビニルエーテル等が挙げられる。
マレイン酸類としては、例えば無水マレイン酸、マレイン酸ジメチル、マレイン酸ジエチル、マレイン酸ジプロピル、マレイン酸ジブチル、マレイン酸ジペンチル、マレイン酸ジへキシル、マレイン酸ジ(2-エチルへキシル)等が挙げられる。
エステル基中に脂肪族骨格を有する(メタ)アクリル酸エステル類としては、例えばメチル(メタ)アクリレート、エチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert-ブチル(メタ)アクリレート、2-エチル-ヘキシル(メタ)アクリレート、ノルマルオクチル(メタ)アクリレート、イソノニル(メタ)アクリレート、イソデシル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、イソステアリル(メタ)アクリレート、イソボルニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、tert-ブチルシクロヘキシル(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,4-ブタンジオールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリペンタエリスリトール(メタ)アクリレート、ポリブタジエン末端ジアクリレート等が挙げられる。
エステル基中にヘテロ原子を有する(メタ)アクリル酸エステル類としては、例えばテトラヒドロフルフリル(メタ)アクリレート、2-メトキシエチル(メタ)アクリレート、エチルカルビトール(メタ)アクリレート、メトキシトリエチレングリコール(メタ)アクリレート、メトキシポリエチレングリコール(メタ)アクリレート、エチレングリコール(メタ)アクリレート、ポリエチレングリコール(メタ)アクリレート、プロピレン(メタ)アクリレート、ポリプロピレン(メタ)アクリレート、(2-メチル-2-エチル-1,3-ジオキソラン-4-イル)メチル(メタ)アクリレート、グリセリンモノ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、環状トリメチロールプロパンホルマール(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、2,2,2-トリフルオロエチル(メタ)アクリレート、2,2,3,3-テトラフルオロプロピル(メタ)アクリレート、リン酸-2-(メタ)アクリロイルオキシエチル、トリス(メタ)アクリロイルオキシエチルフォスフェート、2-((メタ)アクリロイルオキシ)エチルトリメチルアンモニウムクロリド、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート等が挙げられる。
エステル基中に芳香環を有する(メタ)アクリル酸エステル類としては、例えばベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート等が挙げられる。
エステル基中に金属原子を含む(メタ)アクリル酸エステル類としては、例えばジンクモノ(メタ)アクリレート等が挙げられる。
エステル基中に官能基を有する(メタ)アクリル酸エステル類としては、例えばグリシジル(メタ)アクリレート、4―ヒドロキシブチル(メタ)アクリレートグリシジルエーテル、3-エチル-3-オキセタニルメチル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、2-(メタ)アクリロイロキシエチルコハク酸、N,N’-ジメチルアミノエチル(メタ)アクリレート等が挙げられる。
アミド基中に脂肪族骨格を有する(メタ)アクリルアミド類としては、例えばN’,N-ジメチル(メタ)アクリルアミド、N’,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、N-tert-ブチル(メタ)アクリルアミド等が挙げられる。
アミド基中に官能基を有する(メタ)アクリルアミド類としては、例えばN’,N-ジヒドロキシルエチル(メタ)アクリルアミド、N’,N-ジメチルアミノプロピル(メタ)アクリルアミド、N-tert-ブチル(メタ)アクリルアミドスルホン酸、アクリルアミド-tert-ブチルスルホン酸等が挙げられる。
アミド基中にヘテロ原子を有する(メタ)アクリルアミド類としては、例えばアクリロイルモルホリン等が挙げられる。
以下の方法でポリビニル樹脂微粒子およびポリビニル樹脂微粒子組成物の製造、物性評価を行った。結果を表1に示す。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水を1172g、ポリオキシエチレンアルキルエーテル硫酸ナトリウムを58.2g、炭酸水素ナトリウムを2.4g、それぞれ25℃条件下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで水層を得た。500mLのビーカーにメチルメタクリレートを256.0g、ノルマルヘプタンを32.0g、ジオクチル錫ジラウレートを32.0g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで有機層を得た。有機層を水層の入ったセパラブルフラスコへ移し、250rpmの撹拌速度で10分間撹拌することで、プレエマルションを得た。
撹拌機、温度計、加熱装置、還流管、滴下ロートを備えた容量10Lの四口セパラブルフラスコに、メタノールを6400g、室温下で仕込んだ後、100rpmの撹拌速度で撹拌しながら、滴下ロートを用いてポリビニル樹脂組成物を30分かけて全量滴下した。滴下完了後、同様の撹拌速度のまま30分間25℃条件下で撹拌した後、30分間静置することで固液分離をおこなった。デカンテーションにより液を取り除いた後、メタノールを6400g室温下で加え、100rpmの撹拌速度で30分間撹拌した。得られた懸濁液をブフナーロートを用いてろ過した後、ろ過物を真空乾燥器内で-0.1MPa条件下、40℃で2時間乾燥させることで粉体状の触媒内包ポリビニル樹脂微粒子を得た。以下に記載の方法により算出される設計Tgを得られたポリビニル樹脂微粒子のガラス転移温度とした。
動的光散乱法により求めた。条件は以下の通りである。装置として粒径測定装置(大塚電子社製ELSZ-2000)、セルとしてポリスチレン製プラスチックセル(SARSTEDT AG社製)をそれぞれ用いた。
ゲル浸透クロマトグラフィー(GPC)により求めた。条件は以下の通りである。装置として高速GPC装置(東ソー社製HLC-8320GPC)、カラムとしてTSKgel GMHHR-H(いずれも東ソー社製)を2本直列に接続したものを用い、移動相としてテトラヒドロフランを使用し、移動相速度を1.0mL/分とした。カラム温度は40℃とし、検出器は示差屈折率計を用い、ポリメチルメタクリレート換算分子量として分子量を求めた。サンプル溶液は濃度0.10%のTHF溶液を調製して用いた。
ガラス転移温度(Tg)は下記に示すFOX式を用いて算出した。
1/Tg=m1/Tg1+m2/Tg2+m3/Tg3+・・・mn/Tgn (式)
ここで、m1、m2、m3およびmnは用いた各モノマーの質量部、Tg1、Tg2、Tg3およびTgnは用いた各モノマーのホモポリマーのTg(K)を表す。
イソシアネート硬化剤(商品名:C-2612T05、東ソー社製)とポリオール樹脂(商品名:PKN-1082、東ソー社製)とを官能基当量比がイソシアネート基/水酸基=1.0/1.0となる様に混合した。得られた混合樹脂に触媒を加え、均一に分散あるいは溶解するまで混合し、液状のゲルタイム測定用試料を得た。ここで、用いた触媒の量は、触媒内包ポリビニル樹脂微粒子の場合は混合樹脂100質量部に対して10質量部、触媒単体の場合は0.50質量部とした。加熱した金属カップに前記の試料を1mL加え、30分間加熱した。加熱の間、1分毎に試料の性状を目視で確認し、液状からゲル状に変化した際の時間をゲルタイムとして記録した。30分の時点で液状のものは未硬化とした。加熱温度は60℃および140℃の2水準でおこない、それぞれのゲルタイムを測定した。60℃におけるゲルタイムが30分以上であり、かつ140℃におけるゲルタイムが10分未満であれば良好と言える。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水を1172g、ポリオキシエチレンアルキルエーテル硫酸ナトリウムを58.2g、炭酸水素ナトリウムを2.4g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで水層を得た。500mLのビーカーにメチルメタクリレートを224.0g、ノルマルヘプタンを64.0g、ジオクチル錫ジラウレートを32.0g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで有機層を得た。有機層を水層の入ったセパラブルフラスコへ移し、250rpmの撹拌速度で10分間撹拌することで、プレエマルションを得た。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水を1172g、ポリオキシエチレンアルキルエーテル硫酸ナトリウムを58.2g、炭酸水素ナトリウムを2.4g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで水層を得た。500mLのビーカーにメチルメタクリレートを160.0g、ノルマルヘプタンを32.0g、ジオクチル錫ジラウレートを32.0g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで有機層を得た。有機層を水層の入ったセパラブルフラスコへ移し、250rpmの撹拌速度で10分間撹拌することで、プレエマルションを得た。
触媒としてジオクチル錫ジラウレートを用いてゲルタイムを評価した。結果を表1に示す。
触媒を用いない条件でゲルタイムを評価した。結果を表1に示す。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水を1201g、ポリオキシエチレンアルキルエーテル硫酸ナトリウムを54.0g、炭酸水素ナトリウムを1.8g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで水層を得た。500mLのビーカーにメチルメタクリレートを236.0g、ベンジルアクリレートを32.0g、ジオクチル錫ジラウレートを30.0g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで有機層を得た。有機層を水層の入ったセパラブルフラスコへ移し、250rpmの撹拌速度で10分間撹拌することで、プレエマルションを得た。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水を1201g、ポリオキシエチレンアルキルエーテル硫酸ナトリウムを54.0g、炭酸水素ナトリウムを1.8g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで水層を得た。500mLのビーカーにメチルメタクリレートを236.0g、ベンジルアクリレートを32.0g、ヘキサデカンを30.0g、ジオクチル錫ジラウレートを30.0g、それぞれ室温下で仕込んだ。これらを25℃条件下で10分間撹拌し均一にすることで有機層を得た。有機層を水層の入ったセパラブルフラスコへ移し、250rpmの撹拌速度で10分間撹拌することで、プレエマルションを得た。
・ベンジルアクリレート:商品名 ビスコート#160、大阪有機化学工業社製、分配係数LogPow 2.11、ホモポリマーTg 279K
・ジオクチル錫ジラウレート:キシダ化学社製
・ノルマルヘプタン:富士フィルム和光純薬社製 試薬1級
・ヘキサデカン:東京化成工業社製、試薬1級
・ポリオキシエチレンアルキルエーテル硫酸ナトリウム:商品名 ラムテルE-118B、花王社製、cmc 0.55%、
・過硫酸カリウム:富士フィルム和光純薬社製、試薬1級
・炭酸水素ナトリウム:富士フィルム和光純薬社製、食品添加物級。
Claims (19)
- ポリビニル樹脂から成る微粒子中にウレタン樹脂用触媒及び熱膨張剤を内包するポリビニル樹脂微粒子であって、
前記熱膨張剤の沸点が35℃~260℃であり、
塗料用樹脂組成物、接着剤用樹脂組成物または人造皮革用樹脂組成物に用いられることを特徴とするポリビニル樹脂微粒子。 - 前記ポリビニル樹脂が(メタ)アクリルモノマーから得られるポリビニル樹脂を構成成分とすることを特徴とする請求項1に記載のポリビニル樹脂微粒子。
- 前記(メタ)アクリルモノマーの分配係数LogPowが1.00以上であることを特徴とする請求項1又は2に記載のポリビニル樹脂微粒子。
- 前記触媒がスズ、チタン、およびジルコニウムから選ばれる少なくとも1種を含むことを特徴とする請求項1乃至3のいずれかに記載のポリビニル樹脂微粒子。
- 前記熱膨張剤が炭化水素であることを特徴とする請求項1乃至4のいずれかに記載の炭化水素。
- 前記熱膨張剤が脂肪族炭化水素であることを特徴とする請求項1乃至5のいずれかに記載のポリビニル樹脂微粒子。
- ポリビニル樹脂微粒子において、前記触媒及び前記熱膨張剤の合計量(A)と、前記ポリビニル樹脂の質量(B)との質量比が、(A)/(B)として20/80~90/10であり、
前記触媒の質量(a1)と前記熱膨張剤の質量(a2)の質量比が、(a1)/(a2)として10/90~90/10であることを特徴とする請求項1乃至6のいずれかに記載のポリビニル樹脂微粒子。 - 前記ポリビニル樹脂微粒子の平均粒径が30~2,000nmであることを特徴とする請求項1乃至7のいずれかに記載のポリビニル樹脂微粒子。
- 前記ポリビニル樹脂のガラス転移温度が40~200℃であることを特徴とする請求項1乃至8のいずれかに記載のポリビニル樹脂微粒子。
- 前記ポリビニル樹脂の重量平均分子量が500,000~1,500,000であることを特徴とする請求項1乃至9のいずれかに記載のポリビニル樹脂微粒子。
- 請求項1乃至10のいずれかに記載のポリビニル樹脂微粒子を分散溶剤中に分散したポリビニル樹脂微粒子組成物。
- 前記ポリビニル樹脂微粒子を分散する分散溶剤が水であることを特徴とする請求項11に記載のポリビニル樹脂微粒子組成物。
- 請求項1乃至12のいずれかに記載のポリビニル樹脂微粒子又はポリビニル樹脂微粒子組成物を含み、
塗料用、接着剤用または人造皮革用である樹脂組成物。 - 請求項1乃至10のいずれかに記載のポリビニル樹脂微粒子が膜乳化法を用いたミニエマルション重合法により得られることを特徴とする、ポリビニル樹脂微粒子の製造方法。
- 請求項13に記載の樹脂組成物を含む塗料組成物。
- 請求項13に記載の樹脂組成物を含む接着剤組成物。
- 請求項13に記載の樹脂組成物を含む人造皮革用組成物。
- 請求項15乃至17のいずれかに記載の組成物から得られる塗膜。
- 請求項18に記載の塗膜を有する物品。
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