JP5904345B2 - 高機能性重合用添加剤、及びそれを用いた塩化ビニル系シードの製造方法 - Google Patents
高機能性重合用添加剤、及びそれを用いた塩化ビニル系シードの製造方法 Download PDFInfo
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 164
- 238000006116 polymerization reaction Methods 0.000 title claims description 94
- 238000004519 manufacturing process Methods 0.000 title claims description 32
- 239000000654 additive Substances 0.000 title description 2
- 230000000996 additive effect Effects 0.000 title 1
- 239000000178 monomer Substances 0.000 claims description 134
- 239000002245 particle Substances 0.000 claims description 74
- 239000004816 latex Substances 0.000 claims description 56
- 229920000126 latex Polymers 0.000 claims description 56
- 239000011347 resin Substances 0.000 claims description 56
- 229920005989 resin Polymers 0.000 claims description 56
- 239000003655 absorption accelerator Substances 0.000 claims description 54
- 125000001931 aliphatic group Chemical group 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 239000003995 emulsifying agent Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000000265 homogenisation Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 230000004087 circulation Effects 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- -1 sodium dodecyl alkylsulfate Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 230000008961 swelling Effects 0.000 claims description 10
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 9
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 9
- 239000012736 aqueous medium Substances 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 7
- 239000011342 resin composition Substances 0.000 claims description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 229940124532 absorption promoter Drugs 0.000 claims description 5
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 claims description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- QGLITUFXHVRMGV-UHFFFAOYSA-M sodium;tetratriacontyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOS([O-])(=O)=O QGLITUFXHVRMGV-UHFFFAOYSA-M 0.000 claims description 2
- 229940074404 sodium succinate Drugs 0.000 claims 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 25
- 238000002474 experimental method Methods 0.000 description 20
- 230000000694 effects Effects 0.000 description 13
- 238000004904 shortening Methods 0.000 description 10
- 230000036541 health Effects 0.000 description 8
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000012188 paraffin wax Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 239000012875 nonionic emulsifier Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000012874 anionic emulsifier Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920001944 Plastisol Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000004999 plastisol Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 241000212346 Spermolepis Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000012934 organic peroxide initiator Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08F114/00—Homopolymers 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 a halogen
- C08F114/02—Monomers containing chlorine
- C08F114/04—Monomers containing two carbon atoms
- C08F114/06—Vinyl chloride
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- 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
- C08F14/00—Homopolymers and 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 a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- C08F14/06—Vinyl chloride
-
- 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
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
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- 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
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
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- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/003—Removal of residual monomers by physical means from polymer solutions, suspensions, dispersions or emulsions without recovery of the polymer therefrom
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- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/006—Removal of residual monomers by chemical reaction, e.g. scavenging
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
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- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/24—Polymer with special particle form or size
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Claims (14)
- 前記モノマー吸収促進剤は、10000〜0.001mg/1Lの水に対する溶解度を有する脂肪族高級アルコールであることを特徴とする、請求項1に記載の塩化ビニル系シードの製造方法。
- 前記モノマー吸収促進剤は、塩化ビニル系重合体の製造時に0.1〜10phmで使用することを特徴とする、請求項1に記載の塩化ビニル系シードの製造方法。
- 前記重合は、40〜50℃の温度で、9〜12時間の間行うことを特徴とする、請求項1に記載の塩化ビニル系シードの製造方法。
- 前記塩化ビニル系シードの製造方法は、
重合水、塩化ビニル単量体、乳化剤及び前記モノマー吸収促進剤をプレミキシングタンクに投入し、撹拌して混合物を得る膨潤促進段階と、
前記混合物を回転型ホモジナイザーを通過させる均質化段階と、
前記均質化された混合物を反応器で重合させる重合段階と、を含んでなることを特徴とする、請求項1に記載の塩化ビニル系シードの製造方法。 - 前記塩化ビニル単量体100重量部を基準として、前記重合水は20〜150重量部、前記乳化剤は0.1〜10重量部及び前記モノマー吸収促進剤は0.1〜10重量部を投入することを特徴とする、請求項5に記載の塩化ビニル系シードの製造方法。
- 前記乳化剤は、ラウリル硫酸ナトリウム(sodium lauryl sulfate、SLS)、ドデシルベンゼンスルホン酸ナトリウム(sodium dodecyl benzene sulfonate、SDBS)、ドデシルアルキル硫酸ナトリウム(sodium dodecyl alkylsulfate、SDS)、ラウリル硫酸アンモニウム(ammonium lauryl sulfate、ALS)、セチルステアリル硫酸ナトリウム(sodium cetyl stearyl sulfate)、ラウリルエーテル硫酸ナトリウム(sodium lauryl ether sulfate、SLES)及びナトリウムスクシナート(succinate)からなる群から1種以上選択されることを特徴とする、請求項1に記載の塩化ビニル系シードの製造方法。
- 前記膨潤促進段階は、0.1〜5kg/cm2の圧力下で、5〜60分間撹拌することを特徴とする、請求項5に記載の塩化ビニル系シードの製造方法。
- 前記均質化段階では、ホモジナイザーポンプを用いて1〜3時間の間行い、前記回転型ホモジナイザーの循環回数は10〜150回であり、ローター−ステーターの間隔は0.05〜10mmであることを特徴とする、請求項5に記載の塩化ビニル系シードの製造方法。
- 前記モノマー吸収促進剤は、補助乳化剤兼用モノマー吸収促進剤であることを特徴とする、請求項10に記載のモノマー吸収促進剤ベースの塩化ビニル系樹脂用組成物。
- 前記モノマー吸収促進剤は、塩化ビニル系モノマーに対して0.1phm〜10phm含まれることを特徴とする、請求項10に記載のモノマー吸収促進剤ベースの塩化ビニル系樹脂用組成物。
- 請求項12の塩化ビニル系樹脂用組成物を用いてラテックス重合反応を行い、ラテックス重合用反応器に反応水、開始剤、重合抑制剤、モノマー吸収促進剤、塩化ビニル系モノマー及び乳化剤を投入して均質化させた後、重合工程を行うことを特徴とする、モノマー吸収促進剤ベースの塩化ビニル系樹脂組成物を用いたラテックス重合方法。
- 前記モノマー吸収促進剤は、収得しようとする最終ペースト塩化ビニル系樹脂の粒子直径によって種類及び投入量を調節したことを特徴とする、請求項13に記載のモノマー吸収促進剤ベースの塩化ビニル系樹脂組成物を用いたラテックス重合方法。
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20110088862 | 2011-09-02 | ||
KR10-2011-0088862 | 2011-09-02 | ||
KR10-2012-0011522 | 2012-02-03 | ||
KR20120011522 | 2012-02-03 | ||
KR20120011621 | 2012-02-06 | ||
KR10-2012-0011621 | 2012-02-06 | ||
KR10-2012-0051705 | 2012-05-15 | ||
KR10-2012-0051703 | 2012-05-15 | ||
KR1020120051703A KR20130127872A (ko) | 2012-05-15 | 2012-05-15 | 고기능성 중합용 첨가제 |
KR1020120051705A KR101413780B1 (ko) | 2012-05-15 | 2012-05-15 | 모노머 흡수 촉진제 |
PCT/KR2012/006220 WO2013032142A2 (ko) | 2011-09-02 | 2012-08-06 | 고기능성 중합용 첨가제 및 이를 이용한 염화비닐계 시드의 제조방법 |
Publications (2)
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JP2014521823A JP2014521823A (ja) | 2014-08-28 |
JP5904345B2 true JP5904345B2 (ja) | 2016-04-13 |
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Country Status (5)
Country | Link |
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US (1) | US9163134B2 (ja) |
JP (1) | JP5904345B2 (ja) |
CN (1) | CN103732668B (ja) |
DE (1) | DE112012003654B4 (ja) |
WO (1) | WO2013032142A2 (ja) |
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JPS6173714A (ja) * | 1984-09-20 | 1986-04-15 | Mitsui Toatsu Chem Inc | 塩化ビニル樹脂の製造方法 |
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US9163134B2 (en) | 2015-10-20 |
WO2013032142A3 (ko) | 2013-06-13 |
DE112012003654T5 (de) | 2014-08-14 |
WO2013032142A2 (ko) | 2013-03-07 |
CN103732668B (zh) | 2016-01-20 |
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