TWI300068B - Polymerization process involving diacyl peroxides - Google Patents
Polymerization process involving diacyl peroxides Download PDFInfo
- Publication number
- TWI300068B TWI300068B TW092104250A TW92104250A TWI300068B TW I300068 B TWI300068 B TW I300068B TW 092104250 A TW092104250 A TW 092104250A TW 92104250 A TW92104250 A TW 92104250A TW I300068 B TWI300068 B TW I300068B
- Authority
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- Taiwan
- Prior art keywords
- peroxide
- group
- hydrogen
- polymerization
- halide
- Prior art date
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 68
- 239000012933 diacyl peroxide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 104
- 150000002978 peroxides Chemical class 0.000 claims abstract description 51
- 230000008569 process Effects 0.000 claims abstract description 47
- -1 fluorenyl peroxide Chemical class 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 42
- DBNJSZYFWVVQBO-UHFFFAOYSA-N SOOS Chemical compound SOOS DBNJSZYFWVVQBO-UHFFFAOYSA-N 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 238000005502 peroxidation Methods 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 150000004965 peroxy acids Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000000084 colloidal system Substances 0.000 claims description 12
- 229910052684 Cerium Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000265 homogenisation Methods 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000007792 addition Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- RERANOLEWPODQO-UHFFFAOYSA-N 1-(1H-inden-1-ylperoxy)-1H-indene Chemical compound C1(C=CC2=CC=CC=C12)OOC1C=CC2=CC=CC=C12 RERANOLEWPODQO-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
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- 239000011575 calcium Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
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- 238000007254 oxidation reaction Methods 0.000 claims description 3
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- 208000002925 dental caries Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 claims 1
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- ATOFMGTVIWEKRT-UHFFFAOYSA-N cyclohexane;hydrazine Chemical compound NN.C1CCCCC1 ATOFMGTVIWEKRT-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000009781 safety test method Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/34—Per-compounds with one peroxy-radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/32—Peroxy compounds the —O—O— group being bound between two >C=O groups
- C07C409/34—Peroxy compounds the —O—O— group being bound between two >C=O groups both belonging to carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02075882 | 2002-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200303868A TW200303868A (en) | 2003-09-16 |
| TWI300068B true TWI300068B (en) | 2008-08-21 |
Family
ID=27771901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092104250A TWI300068B (en) | 2002-03-01 | 2003-02-27 | Polymerization process involving diacyl peroxides |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7087693B2 (enExample) |
| EP (1) | EP1481013B1 (enExample) |
| JP (3) | JP2005519154A (enExample) |
| KR (2) | KR101128782B1 (enExample) |
| CN (1) | CN1271091C (enExample) |
| AT (1) | ATE366753T1 (enExample) |
| AU (1) | AU2003210325A1 (enExample) |
| BR (1) | BR0308080B1 (enExample) |
| CA (1) | CA2477730A1 (enExample) |
| CO (1) | CO5640051A2 (enExample) |
| DE (1) | DE60314848T2 (enExample) |
| ES (1) | ES2290478T3 (enExample) |
| IL (1) | IL163810A0 (enExample) |
| MX (1) | MXPA04008432A (enExample) |
| NO (1) | NO20044027L (enExample) |
| PL (1) | PL371120A1 (enExample) |
| RU (1) | RU2318002C2 (enExample) |
| TW (1) | TWI300068B (enExample) |
| WO (1) | WO2003074573A1 (enExample) |
| ZA (1) | ZA200407907B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL371120A1 (en) * | 2002-03-01 | 2005-06-13 | Akzo Nobel N.V. | Polymerization process involving diacyl peroxides |
| EP1849804A1 (en) * | 2006-04-27 | 2007-10-31 | Arkema France | Process of free-radical polymerization or crosslinking in the presence of an organic peroxide by an ex situ process |
| EP1852418A1 (en) | 2006-04-27 | 2007-11-07 | Arkema France | Process for synthesizing selected organic peroxides |
| US8846832B2 (en) | 2009-08-06 | 2014-09-30 | Akzo Nobel Chemicals International B.V. | Storage stable and safe peroxide emulsions with a high active oxygen content |
| FR2995905B1 (fr) * | 2012-09-21 | 2015-10-16 | Arkema France | Composition de peroxyde organique sans agent colloide |
| EP3494100B1 (en) * | 2016-07-27 | 2023-01-18 | Dow Global Technologies LLC | Monomer emulsion composition |
| US11976035B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| JP7281563B2 (ja) | 2019-06-12 | 2023-05-25 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップ | ペルオキシエステルを生成するためのプロセス |
| HUE063796T2 (hu) | 2019-06-12 | 2024-01-28 | Nouryon Chemicals Int Bv | Eljárás diacil-peroxidok elõállítására |
| JP7281564B2 (ja) | 2019-06-12 | 2023-05-25 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップ | 過酸化ジアシルを生成するためのプロセス |
| CN116396200A (zh) * | 2023-04-12 | 2023-07-07 | 兰州助剂厂股份有限公司 | 一种过氧化二异丁酰的制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE575693A (enExample) * | 1955-11-30 | |||
| US4155937A (en) * | 1967-04-12 | 1979-05-22 | Polaroid Corporation | Novel polymerization initiators |
| US3502701A (en) * | 1967-05-18 | 1970-03-24 | Argus Chem | Unsymmetrical diacyl peroxides |
| US3652681A (en) * | 1967-10-16 | 1972-03-28 | Argus Chem | Alpha-halo substituted asymmetrical diacyl peroxides |
| GB1271646A (en) * | 1968-07-30 | 1972-04-19 | Chefaro Mij Nv | Organic peroxide compounds and process for preparing same |
| US3936506A (en) * | 1971-10-29 | 1976-02-03 | Union Carbide Corporation | Preparation of unsymmetrical halogen-substituted diacyl peroxides |
| US4071677A (en) * | 1971-12-06 | 1978-01-31 | Argus Chemical Corporation | Polymerization of ethylenically unsaturated monomers employing alpha-halo substituted diacyl peroxides |
| JPS575226B1 (enExample) * | 1973-07-10 | 1982-01-29 | ||
| JPS5968303A (ja) * | 1982-10-12 | 1984-04-18 | Nippon Oil & Fats Co Ltd | 固体の有機過酸化物の水性懸濁液の製造方法 |
| JPS6097953A (ja) * | 1983-11-01 | 1985-05-31 | Nippon Oil & Fats Co Ltd | ジアシルペルオキシドの製造方法 |
| JPS60104104A (ja) * | 1983-11-09 | 1985-06-08 | Sanken Kako Kk | 塩化ビニルの重合方法 |
| JPS61130315A (ja) * | 1984-11-30 | 1986-06-18 | Nippon Oil & Fats Co Ltd | 塩化ビニル系不飽和単量体の懸濁重合方法 |
| JPH01249132A (ja) * | 1988-03-31 | 1989-10-04 | Nippon Oil & Fats Co Ltd | 有機過酸化物の水性エマルション |
| JPH02251506A (ja) * | 1989-03-27 | 1990-10-09 | Nippon Oil & Fats Co Ltd | 塩化ビニルの重合方法及び重合開始剤 |
| US5831131A (en) * | 1995-08-30 | 1998-11-03 | E. I. Du Pont De Nemours And Company | Process for preparing peroxides |
| JPH09183808A (ja) * | 1995-12-28 | 1997-07-15 | Nippon Oil & Fats Co Ltd | ジアシルペルオキシド組成物、その水性エマルション及びそれらを用いる塩化ビニル系重合体の製造方法 |
| HU230607B1 (hu) | 1998-09-21 | 2017-03-28 | Akzo Nobel N.V. | Nagyon gyors iniciátorok folytonos adagolása polimerizációs reakciók során |
| JP2000119311A (ja) * | 1998-10-16 | 2000-04-25 | Nof Corp | ラジカル重合型熱硬化性樹脂用硬化剤、それを用いた硬化物及びその製造方法 |
| US6433208B1 (en) | 1999-11-04 | 2002-08-13 | Oxy Vinyls Lp | Method for producing stable, dilute, aqueous, emulsified peroxydicarbonates by homogenization |
| PL371120A1 (en) * | 2002-03-01 | 2005-06-13 | Akzo Nobel N.V. | Polymerization process involving diacyl peroxides |
-
2003
- 2003-02-20 PL PL03371120A patent/PL371120A1/xx unknown
- 2003-02-20 CA CA002477730A patent/CA2477730A1/en not_active Abandoned
- 2003-02-20 WO PCT/EP2003/001746 patent/WO2003074573A1/en not_active Ceased
- 2003-02-20 KR KR1020047013571A patent/KR101128782B1/ko not_active Expired - Lifetime
- 2003-02-20 US US10/503,052 patent/US7087693B2/en not_active Expired - Lifetime
- 2003-02-20 MX MXPA04008432A patent/MXPA04008432A/es active IP Right Grant
- 2003-02-20 AT AT03743316T patent/ATE366753T1/de not_active IP Right Cessation
- 2003-02-20 IL IL16381003A patent/IL163810A0/xx unknown
- 2003-02-20 EP EP03743316A patent/EP1481013B1/en not_active Expired - Lifetime
- 2003-02-20 BR BRPI0308080-3A patent/BR0308080B1/pt active IP Right Grant
- 2003-02-20 JP JP2003573038A patent/JP2005519154A/ja active Pending
- 2003-02-20 RU RU2004129308/04A patent/RU2318002C2/ru active
- 2003-02-20 DE DE60314848T patent/DE60314848T2/de not_active Expired - Lifetime
- 2003-02-20 AU AU2003210325A patent/AU2003210325A1/en not_active Abandoned
- 2003-02-20 ES ES03743316T patent/ES2290478T3/es not_active Expired - Lifetime
- 2003-02-20 KR KR1020107015378A patent/KR101085427B1/ko not_active Expired - Lifetime
- 2003-02-20 CN CNB038050730A patent/CN1271091C/zh not_active Expired - Lifetime
- 2003-02-27 TW TW092104250A patent/TWI300068B/zh not_active IP Right Cessation
-
2004
- 2004-08-20 CO CO04081595A patent/CO5640051A2/es not_active Application Discontinuation
- 2004-09-24 NO NO20044027A patent/NO20044027L/no not_active Application Discontinuation
- 2004-09-30 ZA ZA2004/07907A patent/ZA200407907B/en unknown
-
2010
- 2010-11-26 JP JP2010264244A patent/JP6177493B2/ja not_active Expired - Lifetime
-
2015
- 2015-05-01 JP JP2015093804A patent/JP6199336B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2318002C2 (ru) | 2008-02-27 |
| KR20040096638A (ko) | 2004-11-16 |
| CN1271091C (zh) | 2006-08-23 |
| DE60314848T2 (de) | 2008-03-20 |
| ZA200407907B (en) | 2005-12-28 |
| RU2004129308A (ru) | 2005-04-10 |
| CN1639202A (zh) | 2005-07-13 |
| TW200303868A (en) | 2003-09-16 |
| ES2290478T3 (es) | 2008-02-16 |
| US7087693B2 (en) | 2006-08-08 |
| JP2005519154A (ja) | 2005-06-30 |
| BR0308080B1 (pt) | 2013-04-09 |
| MXPA04008432A (es) | 2004-11-26 |
| CA2477730A1 (en) | 2003-09-12 |
| WO2003074573A1 (en) | 2003-09-12 |
| AU2003210325A1 (en) | 2003-09-16 |
| JP2011080079A (ja) | 2011-04-21 |
| JP2015163711A (ja) | 2015-09-10 |
| US20050119501A1 (en) | 2005-06-02 |
| KR101085427B1 (ko) | 2011-11-21 |
| NO20044027L (no) | 2004-10-15 |
| EP1481013B1 (en) | 2007-07-11 |
| EP1481013A1 (en) | 2004-12-01 |
| PL371120A1 (en) | 2005-06-13 |
| CO5640051A2 (es) | 2006-05-31 |
| JP6177493B2 (ja) | 2017-08-09 |
| IL163810A0 (en) | 2005-12-18 |
| DE60314848D1 (de) | 2007-08-23 |
| KR101128782B1 (ko) | 2012-03-28 |
| ATE366753T1 (de) | 2007-08-15 |
| KR20100093593A (ko) | 2010-08-25 |
| BR0308080A (pt) | 2004-12-21 |
| JP6199336B2 (ja) | 2017-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Expiration of patent term of an invention patent |