KR101093477B1 - 스티렌을 중합시키기 위한 퍼옥사이드 투여 공정을포함하는 현탁 방법 - Google Patents
스티렌을 중합시키기 위한 퍼옥사이드 투여 공정을포함하는 현탁 방법 Download PDFInfo
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- KR101093477B1 KR101093477B1 KR1020057019422A KR20057019422A KR101093477B1 KR 101093477 B1 KR101093477 B1 KR 101093477B1 KR 1020057019422 A KR1020057019422 A KR 1020057019422A KR 20057019422 A KR20057019422 A KR 20057019422A KR 101093477 B1 KR101093477 B1 KR 101093477B1
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- initiator
- polymerization
- initiators
- monomer
- styrene
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- 238000000034 method Methods 0.000 title claims abstract description 81
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000000725 suspension Substances 0.000 title description 14
- 150000002978 peroxides Chemical class 0.000 title description 10
- 239000003999 initiator Substances 0.000 claims abstract description 113
- 239000011541 reaction mixture Substances 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 74
- 239000000178 monomer Substances 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 11
- 239000004604 Blowing Agent Substances 0.000 claims description 10
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 10
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 9
- 229920006248 expandable polystyrene Polymers 0.000 claims description 6
- -1 ketone peroxides Chemical class 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 claims description 3
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 claims description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 239000012933 diacyl peroxide Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010558 suspension polymerization method Methods 0.000 claims 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 claims 2
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 abstract description 9
- 238000000465 moulding Methods 0.000 abstract description 3
- 229920006249 styrenic copolymer Polymers 0.000 abstract description 2
- 238000010557 suspension polymerization reaction Methods 0.000 abstract description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical group CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 2
- HTCRKQHJUYBQTK-UHFFFAOYSA-N 2-ethylhexyl 2-methylbutan-2-yloxy carbonate Chemical compound CCCCC(CC)COC(=O)OOC(C)(C)CC HTCRKQHJUYBQTK-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 102100040409 Ameloblastin Human genes 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 101000891247 Homo sapiens Ameloblastin Proteins 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002519 antifouling agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/18—Suspension 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
Claims (13)
- 스티렌 모노머, 또는 스티렌을 포함하는 모노머들의 혼합물을 중합시키기 위한 현탁 중합 방법으로서,중합되어 있는 모노머가 없는 시점부터, 모든 모노머의 70 % 이상이 중합될 때까지, 중합 온도에서, 퍼옥시디카르보네이트, 퍼옥시카르보네이트, 퍼옥시에스테르, 퍼옥시케탈, 디아실퍼옥사이드, 디알킬퍼옥사이드, 아조 개시제, 케톤 퍼옥사이드, 및 이들의 혼합물로 이루어진 군으로부터 선택되는 하나 이상의 개시제(개시제는 관능화될 수 있음)를 반응 혼합물에 연속적 또는 반연속적으로 투여(dosing)하는 공정을 포함하며,상기 투여되는 하나 이상의 개시제의 반감기는 상기 중합 온도에서 60 분 이하이며,상기 공정에서 비닐 클로라이드의 양은 모노머의 총 중량을 기준으로 1 중량% 미만인 것을 특징으로 하는 방법.
- 제 1 항에 있어서,상기 모노머들의 혼합물은 비닐 아세테이트, 에틸렌, 프로필렌, 아크릴로니트릴, 부타디엔, (메트)아크릴레이트, 및 폴리부타디엔과 스티렌 부타디엔 고무를 포함하는 에틸렌계 불포화 폴리머로 이루어진 군으로부터 선택되는 코모노머(co-monomer)를 추가로 포함하는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 개시제는 0.1 % 이상의 모노머가 이미 중합되어 있는 시점부터 70 % 이상의 모노머가 중합될 때까지 연속적 또는 반연속적으로 투여되는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 개시제는 디벤조일퍼옥사이드, 1,1-디(tert-부틸퍼옥시)-3,3,5-트리메틸시클로헥산, 2,2-디(tert-부틸퍼옥시)부탄, 1,1-디(tert-부틸퍼옥시)시클로헥산, 2,2'-아조비스(이소부티로니트릴)과 2,2'-아조비스(2-메틸부티로니트릴)을 포함하는 아조 개시제 및 이들의 혼합물로 이루어진 군으로부터 선택되는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 반응 온도가 170 ℃ 이하인 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 개시제의 전부 또는 일부가 0.5 시간 이상에 걸쳐 연속적 또는 반연속적으로 투여되는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,모든 개시제의 배합량은 중합되는 모노머의 중량을 기준으로 0.01 중량% 이상 및 5 중량% 이하인 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,모노머 중합도가 80 % 미만인 경우, 발포제(blowing agent)를 반응 혼합물에 첨가하거나 또는 투여하는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,상기 개시제 또는 개시제의 혼합물은 수성 현탁액의 형태로 투여되는 것을 특징으로 하는 방법.
- 제 1 항 또는 제 2 항에 있어서,잔류 모노머의 수준을 감소시키기 위해, 퍼옥시디카르보네이트, 퍼옥시카르보네이트, 퍼옥시에스테르, 퍼옥시케탈, 디아실퍼옥사이드, 디알킬퍼옥사이드, 아조-개시제, 케톤 퍼옥사이드 및 이들의 혼합물로부터 선택되는 추가의 개시제를 사용하되, 추가의 개시제는 제1항 또는 제2항에서 선택된 개시제와는 상이한 것을 특징으로 하는 방법.
- 제 10 항에 있어서,발포성 폴리스티렌(expandable polystyrene)을 제조하기 위한 것을 특징으로 하는 방법.
- 삭제
- 삭제
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03076088.8 | 2003-04-14 | ||
EP03076088 | 2003-04-14 | ||
US47196303P | 2003-05-20 | 2003-05-20 | |
US60/471,963 | 2003-05-20 | ||
US53022203P | 2003-12-17 | 2003-12-17 | |
US60/530,222 | 2003-12-17 | ||
PCT/EP2004/003661 WO2004089999A2 (en) | 2003-04-14 | 2004-04-02 | Dosing of peroxide to a suspension process wherein styrene is polymerized |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20060012583A KR20060012583A (ko) | 2006-02-08 |
KR101093477B1 true KR101093477B1 (ko) | 2011-12-13 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1020057019422A KR101093477B1 (ko) | 2003-04-14 | 2004-04-02 | 스티렌을 중합시키기 위한 퍼옥사이드 투여 공정을포함하는 현탁 방법 |
Country Status (12)
Country | Link |
---|---|
US (1) | US7132485B2 (ko) |
EP (1) | EP1613672B1 (ko) |
JP (1) | JP4524279B2 (ko) |
KR (1) | KR101093477B1 (ko) |
CN (1) | CN100439406C (ko) |
AR (1) | AR043865A1 (ko) |
BR (1) | BRPI0409446B1 (ko) |
CL (1) | CL2004000789A1 (ko) |
MX (1) | MXPA05011015A (ko) |
PL (1) | PL1613672T3 (ko) |
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Families Citing this family (13)
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FR2879207B1 (fr) * | 2004-12-10 | 2007-07-06 | Commissariat Energie Atomique | Procede et dispositif de fabrication de billes ou de ballons en mousse polymere |
JP2011503335A (ja) * | 2007-11-20 | 2011-01-27 | アクゾ ノーベル ナムローゼ フェンノートシャップ | スチレン系(コ)ポリマーの調製方法 |
US8815971B2 (en) * | 2008-12-22 | 2014-08-26 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
US8822610B2 (en) * | 2008-12-22 | 2014-09-02 | ATRP Solutions, Inc. | Control over controlled radical polymerization processes |
SA110310245B1 (ar) | 2009-04-03 | 2014-11-12 | اكزو نوبل كيميكا | معلق بيروكسيد ثنائي آسيل صلب مائي |
FR2948375B1 (fr) * | 2009-07-27 | 2011-12-30 | Arkema France | Procede de preparation de polystyrene expansible par injection en continu d'un peroxyde organique liquide |
CA2779995A1 (en) * | 2009-12-10 | 2011-06-16 | Akzo Nobel Chemicals International B.V. | Process for the polymerization of styrene |
CN102603929B (zh) * | 2012-02-29 | 2014-10-29 | 无锡知益微球科技有限公司 | 一种高分子颗粒的制备方法 |
KR101336251B1 (ko) * | 2012-08-29 | 2013-12-03 | 포항공과대학교 산학협력단 | 스티렌 단량체를 이용한 전기 방사된 폴리스티렌 나노 섬유의 제조 방법 및 폴리스티렌-양자점 하이브리드 나노섬유의 제조 방법 |
CN102875734B (zh) * | 2012-09-29 | 2014-08-06 | 东莞新长桥塑料有限公司 | 回收级可发性聚苯乙烯以及利用种子聚合法制备回收级可发性聚苯乙烯的方法 |
CN102863569B (zh) * | 2012-09-29 | 2014-05-14 | 东莞新长桥塑料有限公司 | 低挥发性有机物含量的阻燃型可发性聚苯乙烯树脂及其制备方法 |
KR102156109B1 (ko) * | 2017-09-29 | 2020-09-15 | 주식회사 엘지화학 | 탄소섬유 제조용 아크릴로니트릴계 중합체의 제조방법 |
WO2023136699A1 (ko) * | 2022-01-17 | 2023-07-20 | 주식회사 엘지화학 | 중합체의 제조방법 |
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Patent Citations (1)
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US5189069A (en) | 1990-09-15 | 1993-02-23 | Huels Aktiengesellschaft | Process for controlling the particle size in the preparation of expandable styrene polymers by suspension polymerization |
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TW200508258A (en) | 2005-03-01 |
MXPA05011015A (es) | 2005-12-12 |
CN100439406C (zh) | 2008-12-03 |
JP4524279B2 (ja) | 2010-08-11 |
PL1613672T3 (pl) | 2019-12-31 |
BRPI0409446B1 (pt) | 2016-06-07 |
JP2006522844A (ja) | 2006-10-05 |
KR20060012583A (ko) | 2006-02-08 |
WO2004089999A2 (en) | 2004-10-21 |
BRPI0409446A (pt) | 2006-04-18 |
EP1613672B1 (en) | 2019-06-12 |
US20060111529A1 (en) | 2006-05-25 |
WO2004089999A3 (en) | 2005-01-06 |
AR043865A1 (es) | 2005-08-17 |
EP1613672A2 (en) | 2006-01-11 |
CL2004000789A1 (es) | 2005-01-21 |
US7132485B2 (en) | 2006-11-07 |
TWI343924B (en) | 2011-06-21 |
CN1788025A (zh) | 2006-06-14 |
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