JP2021531367A - 二元シリコーン−アクリルポリマー粒子 - Google Patents
二元シリコーン−アクリルポリマー粒子 Download PDFInfo
- Publication number
- JP2021531367A JP2021531367A JP2021500121A JP2021500121A JP2021531367A JP 2021531367 A JP2021531367 A JP 2021531367A JP 2021500121 A JP2021500121 A JP 2021500121A JP 2021500121 A JP2021500121 A JP 2021500121A JP 2021531367 A JP2021531367 A JP 2021531367A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- weight
- acrylic
- particles
- core
- 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
- 239000002245 particle Substances 0.000 title claims abstract description 123
- 229920000058 polyacrylate Polymers 0.000 title claims description 21
- 230000009977 dual effect Effects 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 318
- 239000000178 monomer Substances 0.000 claims abstract description 115
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 72
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims description 84
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010586 diagram Methods 0.000 abstract description 2
- 229910052710 silicon Inorganic materials 0.000 abstract description 2
- 239000010703 silicon Substances 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 41
- 239000000839 emulsion Substances 0.000 description 36
- 238000000034 method Methods 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 239000004816 latex Substances 0.000 description 25
- 229920000126 latex Polymers 0.000 description 25
- 239000011159 matrix material Substances 0.000 description 23
- 125000005907 alkyl ester group Chemical group 0.000 description 22
- 239000004094 surface-active agent Substances 0.000 description 22
- 239000006185 dispersion Substances 0.000 description 21
- 229920002554 vinyl polymer Polymers 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 16
- 229920001296 polysiloxane Polymers 0.000 description 15
- 239000003607 modifier Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 10
- 238000007720 emulsion polymerization reaction Methods 0.000 description 8
- 239000000693 micelle Substances 0.000 description 8
- 239000003599 detergent Substances 0.000 description 7
- 239000012736 aqueous medium Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000004040 coloring Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- -1 polysiloxane Polymers 0.000 description 5
- 239000012966 redox initiator Substances 0.000 description 5
- 241001093575 Alma Species 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 150000001253 acrylic acids Chemical class 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000005395 methacrylic acid group Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920005573 silicon-containing polymer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000009863 impact test Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-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
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- JVXHQHGWBAHSSF-UHFFFAOYSA-L 2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;hydron;iron(2+) Chemical compound [H+].[H+].[Fe+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JVXHQHGWBAHSSF-UHFFFAOYSA-L 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000473391 Archosargus rhomboidalis Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- ILHIHKRJJMKBEE-UHFFFAOYSA-N hydroperoxyethane Chemical compound CCOO ILHIHKRJJMKBEE-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000002609 medium Substances 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
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 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
- 229920002545 silicone oil Polymers 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/12—Copolymers of styrene with unsaturated nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
(I)複数のアクリル粒子(I)であって、各々が、
(a)アクリルコアポリマー(Ia)であって、
(i)1つ以上のモノビニルアクリルモノマー(Iai)の重合単位、
(ii)1つ以上のSi不含グラフトリンカー(Iaii)の重合単位、を含む、アクリルコアポリマー(Ia)と、
(b)1つ以上のアクリルモノマー(Ib)の重合単位を含む、シェルポリマー(Ib)と、を含む、複数のアクリル粒子(I)と、
(II)複数のハイブリッドポリマー粒子(II)であって、各々が、
(a)コアポリマー(IIa)であって、
(i)構造(Y)のモノマー、構造(Z)のモノマー、及びこれらの混合物から選択される、1つ以上のモノマー(IIai)の重合単位、
(ii)任意選択で、1つ以上のモノビニルアクリルモノマー(IIaii)の重合単位、及び
(iii)1つ以上のSi不含グラフトリンカー(IIaiii)の重合単位、を含む、コアポリマー(IIa)と、
(b)1つ以上のアクリルモノマー(IIb)の重合単位を含む、シェルポリマー(IIb)と、を含む、複数のハイブリッドポリマー粒子(II)と、を含む、ポリマー粒子の集合体である。
(A)コアポリマー(IIa)の粒子の分散液(D1)を水性媒体中で準備することであって、コアポリマー(IIa)が、
(i)構造(Y)のモノマー、構造(Z)のモノマー、及びこれらの混合物から選択される、1つ以上のシリコーンモノマー(IIai)の重合単位、
(ii)任意選択で、1つ以上のモノビニルアクリルモノマー(IIaii)の重合単位、及び
(iii)1つ以上のSi不含グラフトリンカー(IIaiii)の重合単位、を含み、
分散液(D1)が、1つ以上の界面活性剤のミセルを含む、準備することと、
(B)モノマーエマルジョン(E2)を分散液(D1)に添加すること、を含む、プロセスによって乳化重合プロセス(B)を行うことにより、ラテックス(L1)を生成することであって、エマルジョン(E2)が、
(i)1つ以上のモノビニルアクリルモノマー(Iai)、及び
(ii)1つ以上のSi不含グラフトリンカー(Iaii)、を含み、
重合プロセス(B)が、コアポリマー(Ia)の分散粒子を水性媒体中で生成するものであり、
ラテックス(L1)が、水性媒体中のコアポリマー(Ia)の分散粒子と、コアポリマー(IIa)の分散粒子と、を含む、ラテックス(L1)を生成することと、
(C)モノマーエマルジョン(E3)をラテックス(L1)に添加すること、を含む、プロセスによって乳化重合プロセス(C)を行うことにより、ラテックス(L2)を生成することであって、エマルジョン(E3)が、1つ以上のアクリルモノマー(Ib)を含む、ラテックス(L2)を生成することと、を含む、方法である。
2=100*WS1/WP2
(界面活性剤の最小量、%)
=282/(液滴の体積平均半径(nm))
好ましくは、エマルジョン(E1)中の界面活性剤の量は、界面活性剤の最小量以上である。
%GS=100*(WPS−WSS)/WPS
[式中、%GSは、グラフト化シェルポリマーの重量%であり、WPSは、全ての重合したシェルポリマーの総重量であり、WSSは可溶性シェルポリマーの重量である]。
TSO−1=テレキーレックシリコーン油、以下の構造を有し、式中、p=198である。
ALMA=アリルメタクリレート。
MMA=メチルメタクリレート。
DS−4=RHODOCAL DS−4(商標)ドデシルベンゼンスルホン酸ナトリウム(Rhodia製)。
NaPS=過硫酸ナトリウム。
pbw=重量部。
10重量%のハイブリッドコアポリマー(IIa)
75重量%のアクリルコアポリマー(Ia)
合計15重量%の全てのシェルポリマー(IbとIIb)
20重量%のハイブリッドコアポリマー(IIa)
65重量%のアクリルコアポリマー(Ia)
合計15%の全てのシェルポリマー(IbとIIb)
実施例1及び2の組成を表1にまとめる。「シェル」とは、シェルポリマー(Ib)とシェルポリマー(IIb)との合計を意味する。
Claims (5)
- (I)複数のアクリル粒子(I)であって、各々が、
(a)アクリルコアポリマー(Ia)であって、
(i)1つ以上のモノビニルアクリルモノマー(Iai)の重合単位、
(ii)1つ以上のSi不含グラフトリンカー(Iaii)の重合単位、を含む、アクリルコアポリマー(Ia)と、
(b)1つ以上のアクリルモノマー(Ib)の重合単位を含む、シェルポリマー(Ib)と、を含む、複数のアクリル粒子(I)と、
(II)複数のハイブリッドポリマー粒子(II)であって、各々が、
(a)コアポリマー(IIa)であって、
(i)構造(Y)のモノマー、構造(Z)のモノマー、及びこれらの混合物から選択される、1つ以上のモノマー(IIai)の重合単位、
(ii)任意選択で、1つ以上のモノビニルアクリルモノマー(IIaii)の重合単位、及び
(iii)1つ以上のSi不含グラフトリンカー(IIaiii)の重合単位、を含む、コアポリマー(IIa)と、
(b)1つ以上のアクリルモノマー(IIb)の重合単位を含む、シェルポリマー(IIb)と、を含む、複数のハイブリッドポリマー粒子(II)と、を含む、ポリマー粒子の集合体。 - コアポリマー(IIa)が、アクリルポリマー粒子(I)の重量とハイブリッドポリマー粒子(II)の重量との合計に基づいて、30重量%〜90重量%の量で存在し、
コアポリマー(Ia)が、アクリルポリマー粒子(I)の重量とハイブリッドポリマー粒子(II)の重量との合計に基づいて、5重量%〜50重量%の量で存在し、
シェルポリマー(Ib)の重量と前記シェルポリマー(IIb)の重量との合計が、アクリルポリマー粒子(I)の重量とハイブリッドポリマー粒子(II)の重量との合計に基づいて、4重量%〜20重量%の量で存在する、請求項1に記載のポリマー粒子の集合体。 - コアポリマー(Ia)の計算Tgが、−80℃〜0℃であり、
コアポリマー(IIa)の計算Tgが、−150℃〜−81℃であり、
シェルポリマー(Ib)の計算Tgが、40℃〜120℃であり、
シェルポリマー(IIb)の計算Tgが、40℃〜120℃である、請求項1に記載のポリマー粒子の集合体。 - シェルポリマー(Ib)の組成が、シェルポリマー(IIb)の組成と同じである、請求項1に記載のポリマー粒子の集合体。
- スチレン/アクリロニトリルと、請求項1に記載の複数のポリマー粒子と、を含む、ポリマー組成物であって、請求項1に記載のポリマー粒子が、前記ポリマー組成物の重量に基づいて、10重量%〜50重量%の量で存在する、ポリマー組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862711147P | 2018-07-27 | 2018-07-27 | |
US62/711,147 | 2018-07-27 | ||
PCT/US2019/043554 WO2020023818A1 (en) | 2018-07-27 | 2019-07-26 | Bimodal silicone-acrylic polymer particles |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021531367A true JP2021531367A (ja) | 2021-11-18 |
JP7523423B2 JP7523423B2 (ja) | 2024-07-26 |
Family
ID=
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0525228A (ja) * | 1990-10-30 | 1993-02-02 | Mitsubishi Rayon Co Ltd | 着色性に優れた熱可塑性樹脂組成物 |
JPH1095911A (ja) * | 1996-09-26 | 1998-04-14 | Mitsubishi Rayon Co Ltd | 熱可塑性樹脂組成物 |
JPH11199642A (ja) * | 1998-01-16 | 1999-07-27 | Mitsubishi Rayon Co Ltd | グラフト共重合体およびそれを含む樹脂組成物 |
WO2009011280A1 (ja) * | 2007-07-13 | 2009-01-22 | Mitsubishi Rayon Co., Ltd. | グラフト共重合体、熱可塑性樹脂組成物及び成形物 |
WO2016158342A1 (ja) * | 2015-03-27 | 2016-10-06 | ユーエムジー・エービーエス株式会社 | 強化熱可塑性樹脂組成物および成形品 |
JP2018090692A (ja) * | 2016-12-02 | 2018-06-14 | 三菱ケミカル株式会社 | ゴム含有グラフト重合体、熱可塑性樹脂組成物および成形体 |
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0525228A (ja) * | 1990-10-30 | 1993-02-02 | Mitsubishi Rayon Co Ltd | 着色性に優れた熱可塑性樹脂組成物 |
JPH1095911A (ja) * | 1996-09-26 | 1998-04-14 | Mitsubishi Rayon Co Ltd | 熱可塑性樹脂組成物 |
JPH11199642A (ja) * | 1998-01-16 | 1999-07-27 | Mitsubishi Rayon Co Ltd | グラフト共重合体およびそれを含む樹脂組成物 |
WO2009011280A1 (ja) * | 2007-07-13 | 2009-01-22 | Mitsubishi Rayon Co., Ltd. | グラフト共重合体、熱可塑性樹脂組成物及び成形物 |
WO2016158342A1 (ja) * | 2015-03-27 | 2016-10-06 | ユーエムジー・エービーエス株式会社 | 強化熱可塑性樹脂組成物および成形品 |
JP2018090692A (ja) * | 2016-12-02 | 2018-06-14 | 三菱ケミカル株式会社 | ゴム含有グラフト重合体、熱可塑性樹脂組成物および成形体 |
Also Published As
Publication number | Publication date |
---|---|
CN112384544B (zh) | 2024-03-12 |
CN112384544A (zh) | 2021-02-19 |
KR20210040376A (ko) | 2021-04-13 |
EP3830149A1 (en) | 2021-06-09 |
BR112020026732A2 (pt) | 2021-04-06 |
US20210324187A1 (en) | 2021-10-21 |
WO2020023818A1 (en) | 2020-01-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2530334B2 (ja) | 高い切欠き衝撃強度を有するグラフト重合体類 | |
CZ199492A3 (en) | Graft copolymers and process for preparing thereof | |
JP7333380B2 (ja) | シリコーン-アクリルポリマー粒子 | |
JP7433283B2 (ja) | シリコーンモノマー及びアクリルモノマーの重合プロセス | |
Zhu et al. | Core–shell particles of poly (methyl methacrylate)‐block‐poly (n‐butyl acrylate) synthesized via reversible addition–fragmentation chain‐transfer emulsion polymerization and the polymer's application in toughening polycarbonate | |
JP2021531367A (ja) | 二元シリコーン−アクリルポリマー粒子 | |
JP7523423B2 (ja) | 二元シリコーン-アクリルポリマー粒子 | |
Ruckenstein et al. | Self-compatibilization of polymer blends via concentrated emulsions | |
JP7422123B2 (ja) | シリコーンとアクリルモノマーとの重合 | |
Zhang et al. | Morphology and mechanical properties of ABS blends prepared from emulsion‐polymerized PB‐g‐SAN impact modifier with AIBN as initiator | |
JP7273816B2 (ja) | グラフトコポリマー組成物 | |
JP7507689B2 (ja) | 改変スチレンアクリロニトリル | |
JP2021024981A (ja) | コア−シェル型粒子、グラフト共重合体、熱可塑性樹脂組成物およびその成形品 | |
JPH0670142B2 (ja) | ポリフェニレンエーテルとシリコーン/有機重合体耐衝撃性向上剤との配合物から得られる成形品の鏡面光沢を調節する方法 | |
KR20240115928A (ko) | 3-단계 중합체 입자 | |
KR20200138269A (ko) | 3-단계 중합체 입자 | |
JPH09136926A (ja) | 透明なゴム強化熱可塑性樹脂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20210108 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20210507 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220719 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230720 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230728 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231027 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20240126 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20240425 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240621 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240705 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240716 |