WO1998003563B1 - Procede d'halogenation de copolymeres d'iso-mono-olefine et de para-alkylstyrene - Google Patents
Procede d'halogenation de copolymeres d'iso-mono-olefine et de para-alkylstyreneInfo
- Publication number
- WO1998003563B1 WO1998003563B1 PCT/US1997/012665 US9712665W WO9803563B1 WO 1998003563 B1 WO1998003563 B1 WO 1998003563B1 US 9712665 W US9712665 W US 9712665W WO 9803563 B1 WO9803563 B1 WO 9803563B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymer
- free radical
- halogenation
- halogenating
- azobis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 32
- 229920001577 copolymer Polymers 0.000 title claims abstract 19
- 238000005658 halogenation reaction Methods 0.000 title claims abstract 12
- 230000002140 halogenating Effects 0.000 claims abstract 14
- 239000007800 oxidant agent Substances 0.000 claims abstract 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract 10
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract 4
- 239000012433 hydrogen halide Substances 0.000 claims abstract 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000011065 in-situ storage Methods 0.000 claims abstract 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- 239000003999 initiator Substances 0.000 claims 6
- 239000007795 chemical reaction product Substances 0.000 claims 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Substances Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 5
- 150000002825 nitriles Chemical class 0.000 claims 5
- -1 bis-azo compound Chemical class 0.000 claims 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N Azobisisobutyronitrile Chemical compound N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 3
- GYAZFWRAWZSHCP-UHFFFAOYSA-N 2-[(2-cyano-4,4-dimethylpentan-2-yl)diazenyl]-2,4,4-trimethylpentanenitrile Chemical compound CC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)C GYAZFWRAWZSHCP-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 238000005893 bromination reaction Methods 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- VHOQXEIFYTTXJU-UHFFFAOYSA-N 2-methylbuta-1,3-diene;2-methylprop-1-ene Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 claims 1
- 240000004282 Grewia occidentalis Species 0.000 claims 1
- SMHGGCAEJFEBEC-UHFFFAOYSA-N N(=NC(C#N)CCC(C)(C)C)C(C#N)CCC(C)(C)C Chemical compound N(=NC(C#N)CCC(C)(C)C)C(C#N)CCC(C)(C)C SMHGGCAEJFEBEC-UHFFFAOYSA-N 0.000 claims 1
- 229920005549 butyl rubber Polymers 0.000 claims 1
- 230000005591 charge neutralization Effects 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000001264 neutralization Effects 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 1
Abstract
Cette invention concerne un procédé d'halogénation d'un copolymère constitué d'une iso-mono-oléfine C4 à C7, telle que l'isobutylène, et d'un para-alkylstyrène, tel que le para-méthylstyrène. On parvient à accroître le rendement de l'halogénation en effectuant la réaction dans des conditions d'halogénation radicalaire et en présence d'un agent d'oxydation, tel que le peroxyde d'hydrogène, qui oxyde l'halogénure d'hydrogène produit in-situ au cours de la réaction et le retransforme en halogène libre. De préférence, on n'ajoute pas ledit agent d'oxydation au milieu réactionnel avant que l'halogénation de première étape ne soit pratiquement achevée.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR9710883A BR9710883A (pt) | 1996-07-24 | 1997-07-18 | Processo para halogena-Æo de copol¡meros isomonoolefina/paraalquilestileno |
| CA002257820A CA2257820C (fr) | 1996-07-24 | 1997-07-18 | Procede d'halogenation de copolymeres d'iso-mono-olefine et de para-alkylstyrene |
| EA199900132A EA199900132A1 (ru) | 1996-07-24 | 1997-07-18 | Способ галоидирования изомоноолефин-пара-алкилстирольных сополимеров |
| PL97330991A PL330991A1 (en) | 1996-07-24 | 1997-07-18 | Method of halogenating copolymers of isomono-olefin and para-alkyl styrene |
| AT0907697A AT406582B (de) | 1996-07-24 | 1997-07-18 | Verfahren zur halogenierung von isomonoolefin/p- alkylstyrol-copolymeren |
| JP50712798A JP4233607B2 (ja) | 1996-07-24 | 1997-07-18 | イソモノオレフィン／パラ―アルキルスチレンコポリマーのハロゲン化方法 |
| EP97933562A EP0914357B1 (fr) | 1996-07-24 | 1997-07-18 | Procede d'halogenation de copolymeres d'iso-mono-olefine et de para-alkylstyrene |
| DE69715424T DE69715424T2 (de) | 1996-07-24 | 1997-07-18 | Verfahren zur halogenierung von isoolefin-para-alkylstyrol-copolymeren |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/686,194 US5670582A (en) | 1996-07-24 | 1996-07-24 | Process for halogenation of isomonoolefin/para-alkylstyrene copolymers |
| US08/686,194 | 1996-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998003563A1 WO1998003563A1 (fr) | 1998-01-29 |
| WO1998003563B1 true WO1998003563B1 (fr) | 1998-02-26 |
Family
ID=24755320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/012665 WO1998003563A1 (fr) | 1996-07-24 | 1997-07-18 | Procede d'halogenation de copolymeres d'iso-mono-olefine et de para-alkylstyrene |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5670582A (fr) |
| EP (1) | EP0914357B1 (fr) |
| JP (1) | JP4233607B2 (fr) |
| KR (1) | KR20000067959A (fr) |
| CN (1) | CN1225648A (fr) |
| AT (1) | AT406582B (fr) |
| BR (1) | BR9710883A (fr) |
| CA (1) | CA2257820C (fr) |
| CZ (1) | CZ21299A3 (fr) |
| DE (1) | DE69715424T2 (fr) |
| EA (1) | EA199900132A1 (fr) |
| ES (1) | ES2179356T3 (fr) |
| HU (1) | HUP9904350A3 (fr) |
| PL (1) | PL330991A1 (fr) |
| WO (1) | WO1998003563A1 (fr) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077913A (en) * | 1998-03-26 | 2000-06-20 | Beholz Technology, L.L.C. | Process for producing paintable polymeric articles |
| US6100343A (en) * | 1998-11-03 | 2000-08-08 | Beholz Technology, L.L.C. | Process for producing paintable polymeric articles |
| CA2325732C (fr) * | 1998-03-26 | 2011-01-11 | Beholz Technology, L.L.C. | Procede de production d'articles polymeres pouvant etre peints |
| CA2247675C (fr) * | 1998-09-17 | 2009-05-05 | Pola Chemical Industries, Inc. | Antifongiques |
| US7901603B1 (en) | 2004-06-21 | 2011-03-08 | Lars Guenter Beholz | Process for producing adhesive polymeric articles from expanded foam materials |
| HU230261B1 (hu) * | 2007-11-27 | 2015-11-30 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Eljárás gyógyszeripari intermedierek előállítására |
| CN102821929B (zh) * | 2010-03-24 | 2015-02-18 | 朗盛国际股份公司 | 不含水和溶剂的聚合物的生产方法 |
| CA2792643C (fr) * | 2010-03-24 | 2020-04-14 | Lanxess International Sa | Procede de production de caoutchoucs de butyle halogenes ne contenant ni eau ni solvants |
| CA2796282C (fr) | 2010-04-30 | 2015-02-03 | Yu Feng Wang | Methode de finition d'elastomere |
| US8242236B2 (en) * | 2010-05-26 | 2012-08-14 | Exxonmobil Chemical Patents Inc. | Elastomeric nanocomposite manufacturing |
| US9079990B2 (en) | 2010-06-01 | 2015-07-14 | Exxonmobil Chemical Patents Inc. | Methods of production of alkylstyrene/isoolefin polymers |
| CN102167844B (zh) * | 2011-03-17 | 2012-12-12 | 北京化工大学 | 以氢溴酸为溴源生产溴化胶粉的方法 |
| US9127137B2 (en) * | 2011-07-20 | 2015-09-08 | Lanxess International Sa | Process for producing brominated butyl rubber |
| CN106061890A (zh) | 2014-02-28 | 2016-10-26 | 埃克森美孚化学专利公司 | 纳米复合材料门尼粘度稳定性 |
| JP6306733B2 (ja) | 2014-02-28 | 2018-04-04 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ムーニー粘度の安定な臭素化エラストマー |
| WO2016053594A1 (fr) | 2014-09-30 | 2016-04-07 | Exxonmobil Chemical Patents Inc. | Procédé de préparation d'un élastomère bromé présentant une stabilité de viscosité de mooney améliorée |
| NL2013819B1 (nl) | 2014-11-17 | 2016-10-10 | Lankhorst Eng Products B V | Bekledingskoker voor het omhullen van een onderwater-leiding. |
| WO2016099694A1 (fr) | 2014-12-19 | 2016-06-23 | Exxonmobil Chemical Patents Inc. | Désactivation de polymérisation |
| JP6815996B2 (ja) * | 2015-07-01 | 2021-01-20 | 株式会社カネカ | ハロゲン化イソオレフィン系重合体の製造方法 |
| US10947375B2 (en) | 2016-01-29 | 2021-03-16 | Exxonmobil Chemical Patents Inc. | System and process for the production of functionalized olefinic-based polymer |
| BR112018069438B1 (pt) * | 2016-03-31 | 2022-07-05 | Fujifilm Corporation | Método para produzir 5- (bromometil) -1-benzotiofeno |
| WO2018217294A1 (fr) | 2017-05-22 | 2018-11-29 | Exxonmobil Chemical Patents Inc. | Élastomères halogénés présentant une stabilité de viscosité de mooney et procédé pour leur préparation |
| JP2020152739A (ja) * | 2017-07-13 | 2020-09-24 | 株式会社カネカ | 臭素化ポリイソブチレン系重合体および製造方法 |
| JP7216826B2 (ja) * | 2018-12-21 | 2023-02-01 | アランセオ・シンガポール・プライヴェート・リミテッド | ハロゲン化イソオレフィンコポリマーの連続製造方法 |
| JP7254183B2 (ja) | 2018-12-27 | 2023-04-07 | アランセオ・シンガポール・プライヴェート・リミテッド | 塩素化ブチルゴムを生成するための方法 |
| CN110272514A (zh) * | 2019-07-05 | 2019-09-24 | 黄河三角洲京博化工研究院有限公司 | 一种溴化异丁烯-对甲基苯乙烯共聚物及其制备方法 |
| WO2022120489A1 (fr) * | 2020-12-11 | 2022-06-16 | ARLANXEO Canada Inc. | Récupération d'halogène avec un oxydant comprenant k+ dans un procédé d'halogénation d'un copolymère d'isooléfine insaturé |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018275A (en) * | 1958-12-30 | 1962-01-23 | Exxon Research Engineering Co | Halogenation of low unsaturation rubbery polymers in the presence of oxidizing agen |
| FR2427343A1 (fr) * | 1978-05-31 | 1979-12-28 | Dia Prosim | Procede de bromation de resines a base de copolymeres vinylaromatiques reticules |
| US5162445A (en) * | 1988-05-27 | 1992-11-10 | Exxon Chemical Patents Inc. | Para-alkylstyrene/isoolefin copolymers and functionalized copolymers thereof |
| CA1338546C (fr) * | 1988-05-27 | 1996-08-20 | Kenneth William Powers | Copolymeres de para-alkylstyrene et d'isoolefine |
| US5077345A (en) * | 1990-03-01 | 1991-12-31 | Exxon Chemical Patents Inc. | Halogenation of polymers with improved neutralization |
| DE4213164A1 (de) * | 1992-04-22 | 1993-10-28 | Bayer Ag | Verfahren zur Herstellung von bromiertem chlorsubstituiertem Poly-1,3-butadien |
| JPH06208743A (ja) * | 1992-12-14 | 1994-07-26 | Olympus Optical Co Ltd | 情報再生装置 |
| DE4437931A1 (de) * | 1994-10-24 | 1996-04-25 | Bayer Ag | Verfahren zur Bromierung von Alkylkautschuken |
| IT1271048B (it) * | 1994-10-27 | 1997-05-26 | Caffaro Spa Ind Chim | Procedimento per la preparazione di polimeri alifatici clorurati |
| US5681901A (en) * | 1996-07-24 | 1997-10-28 | Exxon Chemical Patents Inc. | Process for halogenating isomonoolefin copolymers |
-
1996
- 1996-07-24 US US08/686,194 patent/US5670582A/en not_active Expired - Lifetime
-
1997
- 1997-07-18 DE DE69715424T patent/DE69715424T2/de not_active Expired - Lifetime
- 1997-07-18 EP EP97933562A patent/EP0914357B1/fr not_active Expired - Lifetime
- 1997-07-18 HU HU9904350A patent/HUP9904350A3/hu unknown
- 1997-07-18 CN CN97196596A patent/CN1225648A/zh active Pending
- 1997-07-18 BR BR9710883A patent/BR9710883A/pt not_active Application Discontinuation
- 1997-07-18 KR KR1019997000458A patent/KR20000067959A/ko active IP Right Grant
- 1997-07-18 AT AT0907697A patent/AT406582B/de not_active IP Right Cessation
- 1997-07-18 PL PL97330991A patent/PL330991A1/xx unknown
- 1997-07-18 EA EA199900132A patent/EA199900132A1/ru unknown
- 1997-07-18 WO PCT/US1997/012665 patent/WO1998003563A1/fr active IP Right Grant
- 1997-07-18 CZ CZ99212A patent/CZ21299A3/cs unknown
- 1997-07-18 CA CA002257820A patent/CA2257820C/fr not_active Expired - Lifetime
- 1997-07-18 JP JP50712798A patent/JP4233607B2/ja not_active Expired - Lifetime
- 1997-07-18 ES ES97933562T patent/ES2179356T3/es not_active Expired - Lifetime
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