KR100581702B1 - 폴리(알릴 카보네이트)-작용성 예비중합체 조성물의 제조방법 - Google Patents
폴리(알릴 카보네이트)-작용성 예비중합체 조성물의 제조방법 Download PDFInfo
- Publication number
- KR100581702B1 KR100581702B1 KR1020007007376A KR20007007376A KR100581702B1 KR 100581702 B1 KR100581702 B1 KR 100581702B1 KR 1020007007376 A KR1020007007376 A KR 1020007007376A KR 20007007376 A KR20007007376 A KR 20007007376A KR 100581702 B1 KR100581702 B1 KR 100581702B1
- Authority
- KR
- South Korea
- Prior art keywords
- temperature
- allyl carbonate
- hour half
- free radical
- radical initiator
- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 99
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000003999 initiator Substances 0.000 claims abstract description 82
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 150000003254 radicals Chemical class 0.000 claims abstract description 26
- 238000001816 cooling Methods 0.000 claims abstract description 25
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 39
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- 239000011541 reaction mixture Substances 0.000 claims description 34
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 claims description 7
- 230000000977 initiatory effect Effects 0.000 claims 3
- 238000005507 spraying Methods 0.000 claims 2
- -1 poly (allyl carbonates Chemical class 0.000 description 52
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 10
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
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- 125000002947 alkylene group Chemical group 0.000 description 7
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- 238000005486 sulfidation Methods 0.000 description 6
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- 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 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 description 4
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 3
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 229920002574 CR-39 Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
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- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- 239000006227 byproduct Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 125000001033 ether group Chemical group 0.000 description 2
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- VOSUIKFOFHZNED-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,3,5-tricarboxylate Chemical compound C=CCOC(=O)C1=CC(C(=O)OCC=C)=CC(C(=O)OCC=C)=C1 VOSUIKFOFHZNED-UHFFFAOYSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 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
- C08F18/00—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/24—Esters of carbonic or haloformic 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/34—Per-compounds with one peroxy-radical
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/000,660 | 1997-12-30 | ||
| US09/000,660 US6057411A (en) | 1997-12-30 | 1997-12-30 | Process for forming poly(allyl carbonate)-functional prepolymer composition |
| PCT/US1998/027124 WO1999033888A1 (en) | 1997-12-30 | 1998-12-16 | Process for forming poly(allyl carbonate)-functional prepolymer composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010033820A KR20010033820A (ko) | 2001-04-25 |
| KR100581702B1 true KR100581702B1 (ko) | 2006-05-23 |
Family
ID=21692482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007007376A Expired - Lifetime KR100581702B1 (ko) | 1997-12-30 | 1998-12-16 | 폴리(알릴 카보네이트)-작용성 예비중합체 조성물의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6057411A (enExample) |
| EP (1) | EP1044228B1 (enExample) |
| JP (1) | JP2001527139A (enExample) |
| KR (1) | KR100581702B1 (enExample) |
| CN (1) | CN1151185C (enExample) |
| AU (1) | AU736698B2 (enExample) |
| BR (1) | BR9814728A (enExample) |
| DE (1) | DE69806510T2 (enExample) |
| ES (1) | ES2180226T3 (enExample) |
| HU (1) | HU224005B1 (enExample) |
| ID (1) | ID26035A (enExample) |
| IL (2) | IL137091A (enExample) |
| PL (1) | PL341533A1 (enExample) |
| TW (1) | TW521076B (enExample) |
| WO (1) | WO1999033888A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952441A (en) * | 1997-12-30 | 1999-09-14 | Ppg Industries Ohio, Inc. | Partially polymerized mixture of diethylene glycol (allyl carbonate) compounds |
| US6506864B1 (en) | 2000-04-10 | 2003-01-14 | Ppg Industries Ohio, Inc. | Polymerizable composition of allyl functional monomers |
| CN1221579C (zh) * | 2000-04-10 | 2005-10-05 | Ppg工业俄亥俄公司 | 烯丙基官能单体的可聚合组合物 |
| CA2442998A1 (en) * | 2001-04-09 | 2002-10-17 | David P. Dumas | Transparent polymer support for organic synthesis |
| US6617388B2 (en) * | 2001-10-12 | 2003-09-09 | Atofina Chemicals, Inc. | Curing catalyst |
| US20040118688A1 (en) * | 2002-07-29 | 2004-06-24 | Dumas David P. | Transparent polymer support for electrophoresis and electrochromatography and related methods |
| US20060289098A1 (en) * | 2005-06-23 | 2006-12-28 | Balogh George F | Tire containing cellular rubber within its tire cavity |
| US10407540B2 (en) * | 2015-09-08 | 2019-09-10 | Ppg Industries Ohio, Inc. | Composition for optical articles and optical articles made therewith |
| WO2018035112A1 (en) * | 2016-08-16 | 2018-02-22 | Ppg Industries Ohio, Inc. | Polymerizable composition for optical articles |
| IT202300015492A1 (it) | 2023-07-24 | 2025-01-24 | Mitsui Chemicals Inc | Processo per fabbricare un articolo ottico polimerico e composizione utilizzata in detto metodo. |
| IT202300017712A1 (it) | 2023-08-29 | 2025-03-01 | Mitsui Chemicals Inc | Metodo per preparare una composizione di prepolimero poliallil-funzionale e uso di detta composizione di prepolimero per fabbricare un articolo ottico. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4623708A (en) * | 1985-03-01 | 1986-11-18 | Coburn Optical Industries, Inc. | Prepolymerization of monomer compositions containing diethylene glycol bis(allyl carbonate) |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE62448C (de) * | G. schwarzlose in Breslau, Bahnhofstr. 22 | Vorrichtung zur Verhinderung des Lockerns von Glühlampen | ||
| FR1541889A (fr) * | 1967-10-25 | 1968-10-11 | Zeiss Jena Veb Carl | Procédé de production d'un matière plastique résistant au rayage et au frottement, pour verres optiques |
| JPS519188A (ja) * | 1974-07-16 | 1976-01-24 | Teijin Chemicals Ltd | Purehorimaanoseizoho |
| JPS5726521A (en) * | 1980-07-21 | 1982-02-12 | Sanraku Ocean Co | Culture medium of mushroom |
| JPS57133106A (en) * | 1981-02-10 | 1982-08-17 | Asahi Optical Co Ltd | Preparation of prepolymer |
| JPS58167125A (ja) * | 1982-03-29 | 1983-10-03 | Nippon Oil & Fats Co Ltd | プラスチツクレンズの製造方法 |
| US5017666A (en) * | 1983-11-09 | 1991-05-21 | Ppg Industries, Inc. | Polyol(allyl carbonate) compositions and polymerizates prepared therefrom |
| JPS6151012A (ja) * | 1984-08-21 | 1986-03-13 | Nippon Oil & Fats Co Ltd | プレポリマ−の製造方法 |
| JPS6164706A (ja) * | 1984-09-07 | 1986-04-03 | Tokuyama Soda Co Ltd | 液状プレポリマ−の製造方法 |
| US4686266A (en) * | 1984-11-23 | 1987-08-11 | Ppg Industries, Inc. | Bis(allyl carbonate) monomer and method for polymerizing same |
| US4613656A (en) * | 1984-11-23 | 1986-09-23 | Ppg Industries, Inc. | Method for polymerizing bis(allyl carbonate) resin |
| JPS61296009A (ja) * | 1985-06-24 | 1986-12-26 | Tokuyama Soda Co Ltd | 液状プレポリマ−の製造方法 |
| US4742133A (en) * | 1985-09-24 | 1988-05-03 | Ppg Industries, Inc. | Poly(allyl carbonate)-functional prepolymers prepared by treatment with molecular oxygen |
| US4959429A (en) * | 1985-11-22 | 1990-09-25 | Ppg Industries, Inc. | Cyclohexenic additives for producing polycarbonate polymers of high refractive index and low yellowness |
| US4959433A (en) * | 1986-03-17 | 1990-09-25 | Ppg Industries, Inc. | Partially polymerized bis(allylic carbonate) monomer having high allylic utilization |
| US4829136A (en) * | 1988-05-13 | 1989-05-09 | Ppg Industries, Inc. | Compositions for producing polymers of high refractive index |
| JP2997100B2 (ja) * | 1991-07-23 | 2000-01-11 | シャープ株式会社 | 光半導体装置 |
-
1997
- 1997-12-30 US US09/000,660 patent/US6057411A/en not_active Expired - Fee Related
-
1998
- 1998-12-16 IL IL13709199A patent/IL137091A/xx not_active IP Right Cessation
- 1998-12-16 AU AU19341/99A patent/AU736698B2/en not_active Ceased
- 1998-12-16 WO PCT/US1998/027124 patent/WO1999033888A1/en not_active Ceased
- 1998-12-16 CN CNB98813439XA patent/CN1151185C/zh not_active Expired - Lifetime
- 1998-12-16 BR BR9814728-5A patent/BR9814728A/pt not_active IP Right Cessation
- 1998-12-16 HU HU0100471A patent/HU224005B1/hu not_active IP Right Cessation
- 1998-12-16 KR KR1020007007376A patent/KR100581702B1/ko not_active Expired - Lifetime
- 1998-12-16 IL IL13709198A patent/IL137091A0/xx unknown
- 1998-12-16 JP JP2000526559A patent/JP2001527139A/ja active Pending
- 1998-12-16 ID IDW20001453A patent/ID26035A/id unknown
- 1998-12-16 EP EP98964154A patent/EP1044228B1/en not_active Expired - Lifetime
- 1998-12-16 DE DE69806510T patent/DE69806510T2/de not_active Expired - Fee Related
- 1998-12-16 PL PL98341533A patent/PL341533A1/xx not_active IP Right Cessation
- 1998-12-16 ES ES98964154T patent/ES2180226T3/es not_active Expired - Lifetime
-
1999
- 1999-02-09 TW TW087121889A patent/TW521076B/zh not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4623708A (en) * | 1985-03-01 | 1986-11-18 | Coburn Optical Industries, Inc. | Prepolymerization of monomer compositions containing diethylene glycol bis(allyl carbonate) |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1284090A (zh) | 2001-02-14 |
| ES2180226T3 (es) | 2003-02-01 |
| BR9814728A (pt) | 2001-11-06 |
| DE69806510D1 (de) | 2002-08-14 |
| HUP0100471A3 (en) | 2002-03-28 |
| EP1044228A1 (en) | 2000-10-18 |
| IL137091A0 (en) | 2001-06-14 |
| WO1999033888A1 (en) | 1999-07-08 |
| TW521076B (en) | 2003-02-21 |
| CN1151185C (zh) | 2004-05-26 |
| US6057411A (en) | 2000-05-02 |
| JP2001527139A (ja) | 2001-12-25 |
| KR20010033820A (ko) | 2001-04-25 |
| ID26035A (id) | 2000-11-16 |
| AU1934199A (en) | 1999-07-19 |
| HU224005B1 (hu) | 2005-04-28 |
| PL341533A1 (en) | 2001-04-23 |
| DE69806510T2 (de) | 2003-03-20 |
| HUP0100471A2 (hu) | 2001-06-28 |
| EP1044228B1 (en) | 2002-07-10 |
| IL137091A (en) | 2005-12-18 |
| AU736698B2 (en) | 2001-08-02 |
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