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Halobutyl elastomers

A kind of elastomer, butyl technology, applied in the field of halogenated butyl elastomer, can solve problems such as difficulties

Inactive Publication Date: 2008-07-30
LANXESS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] While nucleophilic substitution reactions with neutral amines and phosphines are easy to occur, similar reactions with oxygen- or sulfur-based nucleophiles are much more difficult

Method used

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  • Halobutyl elastomers

Examples

Experimental program
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Effect test

example

[0029] Material

[0030] 2,2,4,8,8-pentamethyl-4-nonene bromide (BPMN) was prepared as previously described (Parent, J.S. Thom, D.J. White, G. Whitney, R.A. Hopkins, W.J. Polym. Sci. Part A: Polym. Chem. 2001, 29, 2019-2026). The following reagents were used as received from Sigma-Aldrich (Oakville, Ontario): tetrabutylammonium hydroxide (1 M in methanol), tetrabutylammonium bromide (98%) (TBAB), trioctylmethyl chloride Ammonium chloride (Aliquat(R) 336, 95%), tert-butylacetic acid (98%), stearic acid (98%), benzoic acid (98%), 4-(dimethylamino)benzoic acid (98%), anthracene -9-Carboxylic acid (98%), linoleic acid (99%), and potassium hydroxide (99%). BIIR (Bayer BB2030) was used in the form supplied by LANXESS Corporation (Sarnia, Ontario). Tetrabutylammonium and potassium carboxylates are prepared by neutralization of the corresponding carboxylic acids with appropriate hydroxide bases.

[0031] equipment

[0032] The solid phase PTC reaction was performed using a Ha...

example 1

[0038] Example 1: (3,3-Dimethylbutyl)-2-(2,2-dimethylpropyl)prop-2-enyl 3,3-dimethylbutyrate (Example 1a) and ( Synthesis of 2E / Z)-6,6-dimethyl-2-(2,2-dimethylpropyl)hept-2-enyl 3,3-dimethylbutyrate (Example 1b-c) separate from

[0039] BPMN (0.022 g, 0.081 mmole), tetrabutylammonium tert-butylacetate (0.043 g, 0.120 mmole) and dodecane (0.4 ml) were sealed in a 1 ml Wheaton bottle and heated to 100° C. for one hour . The product was purified by column chromatography (silica gel, hexane) and isolated under vacuum to yield a yellow oil. Exocyclic methylene isomer Example 1a can be separated by column chromatography using silica gel and a mixed solvent (hexane:acetone:diethyl ether). FT-IR analysis: 1734cm -1 (C=O); MS analysis: C 20 h 38 o 2 Desired mass was 310.5m / e, found 311.4m / e [M+H] + (CI+) and 333.21m / e[M+Na] + (ESI+); 1 H NMR (CDCl 3 ) Example 1a: δ 5.18 (dd, 1H, -CHOC(O)-), 5.09 (s, 1.04H, =CH 2 ), 4, 86 (s, 1.06, =CH 2 ), 2.20 (dd, 2.1H, -CH 2 -), 1.92 (...

example 2

[0040] Example 2: (3,3-Dimethylbutyl)-2-(2,2-Dimethylpropyl)prop-2-enyl stearate (Example 2a) and (2E / Z)-6 , Synthesis and isolation of 6-dimethyl-2-(2,2-dimethylpropyl)hept-2-enyl stearate (Example 2b-c)

[0041] BPMN (0.044 g, 0.163 mmole), tetrabutylammonium stearate (0.085 g, 0.162 mmole) and dodecane (0.4 mL) were sealed in a 1 mL Wheaton bottle and heated to 100°C for one hour. The product was purified by column chromatography (silica gel, hexane) and isolated in vacuo to yield a yellow oil. FT-IR analysis: 1734cm -1 (C=O). MS Analysis: C 32 h 62 o 2 Desired mass is 478.83m / e, found 478.5m / e(EI+) and 479.5m / e[M+H] + (CI+). 1 H NMR (CDCl 3 ) Example 2: δ0.6-2.4 (m, 108, 2H, 3x-C (CH 3 ) 3 , 19x-CH 2 -), 4.4-5.6(m, 3.3H, 1x-CHOC(O)-, 2x=CH 2 , 2x-CH 2 OC(O)-, 2x=C-H); Example 2a: δ5.17(dd, -CHOC(O)-), 5.07(s,=CH 2 ), 4.84(s,=CH 2 ); Example 2b: δ4.49 (s, -CH 2 OC(O)-), 5.52(t,=C-H); Example 2c: δ4.56(s,-CH 2 OC(O)-), 5.39(t, =C-H).

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Abstract

The present invention relates to the modification of butyl elastomers, particularly halobutyl elastomers, under solvent free conditions with a phase transfer catalyst, particularly tetrabutyammonium bromide or trioctylmethylammonium chloride, in the presence of an alkyl metal salt of an oxygen or sulfur-based nucleophile. Suitable nucleophiles for use in the present invention include metal salts of tert-butylacetic acid, stearic acid, benzoic acid, 4-(dimethylamino)benzoic acid, antrancene-9-carboxylic acid, linoleic acid or mixture thereof, which are prepared by neutralization with an appropriate hydroxide base.

Description

technical field [0001] The present invention relates to the modification of butyl elastomers, particularly halobutyl elastomers, under solvent-free conditions using a phase transfer catalyst in the presence of an alkyl metal salt of an oxygen- or sulfur-based nucleophile. Background technique [0002] Butyl rubber (IIR), a random copolymer of isobutylene and isoprene, is known for its excellent thermal stability, ozone resistance and ideal wetting characteristics. IIR is commercially prepared by a slurry process using methyl chloride as the vehicle and a Friedel-Crafts catalyst as the polymerization initiator. The benefit of methyl chloride is AlCl 3 As a relatively inexpensive Friedel-Crafts catalyst, it is soluble, as are isobutylene and isoprene comonomers. In addition, butyl rubber polymers are insoluble in methyl chloride and precipitate out of solution as fine particles. The polymerization reaction is generally carried out at a temperature between about -90°C and -1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08L23/22C08L23/28
CPCC08F8/00C08F8/30C08L23/22C08L23/283C08F8/26C08F8/20C08F210/12C08L2666/02C08F8/14C08F210/10C08L23/28
Inventor 约翰·斯科特·帕伦特鲁尔·雷森德斯拉尔夫·艾伦·惠特尼塞尔希奥·A·吉伦-卡斯特利亚诺斯
Owner LANXESS INC
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