JP4755211B2 - 六置換グアニジニウムクロライドの水溶液からなる組成物 - Google Patents
六置換グアニジニウムクロライドの水溶液からなる組成物 Download PDFInfo
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- JP4755211B2 JP4755211B2 JP2008023337A JP2008023337A JP4755211B2 JP 4755211 B2 JP4755211 B2 JP 4755211B2 JP 2008023337 A JP2008023337 A JP 2008023337A JP 2008023337 A JP2008023337 A JP 2008023337A JP 4755211 B2 JP4755211 B2 JP 4755211B2
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- Prior art keywords
- chloride
- water
- mixture
- phosgene
- range
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1021—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the catalyst used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Hydrogenated Pyridines (AREA)
Description
(発明の要約) 本発明は、六置換グアニジニウム塩およびその中間体の調製、かかる塩を含んだ組成物、並びにかかる組成物のポリエーテルイミドおよびその中間体の調製における相間移動触媒としての使用に関連した多くの観点を有する。それぞれの観点に関してさっそく以下に要約する。
(III) R2(ZM)2
の化合物である。上記式中、R2 は約6−30個の炭素原子を含有する2価の芳香族基であり、Mはアルカリ金属であり、そしてZは酸素または硫黄である。R2 基は炭化水素基でよく、また酸素または硫黄のような他の原子を含有していてもよい。R2 基を誘導しうるジヒドロキシ芳香族化合物の例には、レゾルシノール、ヒドロキノン、4,4′−ジヒドロキシビフェニル、4,4′−ジヒドロキシ−3,3′,5,5′−テトラメチルビフェニル、ビス(4−ヒドロキシフェニル)メタン、3−ヒドロキシフェニル−4−ヒドロキシフェニルメタン、2,2−ビス(2−ヒドロキシフェニル)プロパン、2,2−ビス(4−ヒドロキシフェニル)プロパン(以後「ビスフェノールA」と呼ぶ)、2−(3−ヒドロキシフェニル)−2−(4−ヒドロキシフェニル)プロパン、1,1−ビス(4−ヒドロキシフェニル)エタン、2,2−ビス(4−ヒドロキシフェニル)ペンタン、1,1−ビス(4−ヒドロキシフェニル)エチレン、4,4′−ジヒドロキシベンゾフェノン、ビス(4−ヒドロキシフェニル)エーテル、ビス(4−ヒドロキシフェニル)スルフィド、ビス(4−ヒドロキシフェニル)スルホキシド、ビス(4−ヒドロキシフェニル)スルホンおよび3−ヒドロキシフェニル−4−ヒドロキシフェニルスルホン。
Claims (2)
- 下記の(A)乃至(G)からなる調整方法で得られる2−12の範囲のpHを有する六置換グアニジニウムクロライドの水溶液からなる組成物。
六置換グアニジニウム塩の水溶液の調製方法において、
(A)40−80℃の範囲の反応温度で、アルカリ金属塩基の添加により10−13の範囲に維持されたpHにおいて、脂肪族または脂環式第二アミンと、水と、ベンゼン、トルエン、キシレン、クロロベンゼン、o−ジクロロベンゼン、クロロトルエン、ジクロロトルエンまたはオクタンから選択される有機溶媒とを含む混合物中にホスゲンを通過させ、その際、前記水の量を飽和濃度の少なくとも95重量%の濃度を有するアルカリ金属塩化物副生物の溶液を生成するのに有効な割合とし、前記ホスゲンと前記アミンの当量比を1.0−1.15:1の範囲とし、前記有機溶媒と前記水の容量比を0.8−5.0:1の範囲とし、そして前記アミンの割合を完全な転換を想定したときに前記有機溶媒中に生成物の25−90重量%の溶液を与えるように計算し、これにより四置換尿素を含んだ第一の生成物の混合物を生成し、
(B)前記第一の生成物の混合物から水、アミンおよびアルカリ金属塩化物を除去して第一の生成物混合物を生成し、
(C)必要ならば前記有機溶媒を添加するかあるいは除去することにより前記第一の生成物混合物を40−80重量%の範囲の四置換尿素濃度に調節し、
(D)60−80℃の範囲の温度でホスゲンを導入し、その際、ホスゲンの添加量を存在するあらゆる水と反応し、加えてホスゲンと前記四置換尿素の当量比を1.05−1.15:1の範囲とするのに有効な割合とし、これにより四置換クロルホルムアミジニウムクロライドを含む無水の混合物を生成し、
(E)前記無水の混合物から未反応のあらゆるホスゲンを取り除き、
(F)前記四置換クロルホルムアミジニウムクロライドを六置換グアニジニウム塩に変換するのに有効な量で第二アミンを前記無水の混合物に添加し、そして
(G)前記六置換グアニジニウム塩を塩基性媒体中の水で希釈して水性相および有機相を生成し、未反応の第二アミンを含む前記有機相を除去し、そして前記六置換グアニジニウム塩を含有する前記水性相を必要なら酸を添加してそのpHを2−12の範囲の値に調節する。 - 前記六置換グアニジニウムクロライドがヘキサエチルグアニジニウムクロライドである請求項1記載の組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/583921 | 1996-01-11 | ||
US08/583,921 US5872294A (en) | 1996-01-11 | 1996-01-11 | Aqueous hexasubstituted guanidinium chlorides and methods for their preparation and use |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP00175797A Division JP4105252B2 (ja) | 1996-01-11 | 1997-01-09 | 六置換グアニジニウムクロライド水溶液並びにその調製法および用法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008120825A JP2008120825A (ja) | 2008-05-29 |
JP2008120825A5 JP2008120825A5 (ja) | 2008-08-14 |
JP4755211B2 true JP4755211B2 (ja) | 2011-08-24 |
Family
ID=24335162
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP00175797A Expired - Fee Related JP4105252B2 (ja) | 1996-01-11 | 1997-01-09 | 六置換グアニジニウムクロライド水溶液並びにその調製法および用法 |
JP2008023337A Expired - Lifetime JP4755211B2 (ja) | 1996-01-11 | 2008-02-01 | 六置換グアニジニウムクロライドの水溶液からなる組成物 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP00175797A Expired - Fee Related JP4105252B2 (ja) | 1996-01-11 | 1997-01-09 | 六置換グアニジニウムクロライド水溶液並びにその調製法および用法 |
Country Status (6)
Country | Link |
---|---|
US (3) | US5872294A (ja) |
EP (1) | EP0784051B1 (ja) |
JP (2) | JP4105252B2 (ja) |
DE (1) | DE69714483T2 (ja) |
ES (1) | ES2183083T3 (ja) |
SG (1) | SG50763A1 (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6638621B2 (en) | 2000-08-16 | 2003-10-28 | Lyotropic Therapeutics, Inc. | Coated particles, methods of making and using |
US6028203A (en) * | 1998-12-14 | 2000-02-22 | General Electric Company | Phase transfer catalyzed method for prepared oxybisphthalic compounds |
US7047054B2 (en) * | 1999-03-12 | 2006-05-16 | Cas Medical Systems, Inc. | Laser diode optical transducer assembly for non-invasive spectrophotometric blood oxygenation monitoring |
GB2379217B (en) * | 2001-08-31 | 2004-11-10 | Chordip Ltd | Halogen exchange reactions and catalysts therefor |
US6576770B1 (en) | 2001-12-05 | 2003-06-10 | General Electric Company | Preparation of substituted phthalic anhydrides and substituted phthalimides |
US6498224B1 (en) | 2001-12-05 | 2002-12-24 | General Electric Company | Methods for the preparation poly(etherimide)s |
US6528663B1 (en) | 2001-12-05 | 2003-03-04 | General Electric Company | Methods for the preparation of 4-chlorophthalic anhydride |
US6881815B2 (en) | 2002-09-25 | 2005-04-19 | General Electric Company | Method for the preparation poly(etherimide)s |
US7071282B2 (en) * | 2003-06-03 | 2006-07-04 | General Electric Company | Benzimidazole diamine-based polyetherimide compositions and methods for making them |
US20050029194A1 (en) * | 2003-08-07 | 2005-02-10 | Hall David Bruce | Method for removal of guanidine compound from aqueous media |
US20050049390A1 (en) * | 2003-08-25 | 2005-03-03 | General Electric Company | Phase transfer catalyzed method for preparation of polyetherimides |
US7714095B2 (en) | 2003-08-25 | 2010-05-11 | Sabic Innovative Plastics Ip B.V. | Phase transfer catalyzed method for preparation of polyetherimides |
US7125954B2 (en) * | 2005-01-27 | 2006-10-24 | General Electric Company | Method for producing polyether polymers |
US7528273B2 (en) | 2005-04-14 | 2009-05-05 | Momentive Performance Materials Inc. | Aqueous catalytic process for the preparation of thiocarboxylate silane |
US7262312B2 (en) * | 2005-08-05 | 2007-08-28 | Sheridan Robert E | Process for producing organoalkoxysilanes from organic acids or cyanates and haloalkylalkoxysilanes |
US7151188B1 (en) | 2005-11-16 | 2006-12-19 | General Electric Company | Process for the production of mercaptoalkylalkoxysilanes |
US20070287776A1 (en) * | 2006-06-08 | 2007-12-13 | Akzo Nobel N.V. | Microspheres |
US7982993B1 (en) | 2008-12-19 | 2011-07-19 | Western Digital Technologies, Inc. | Disk drive employing different servo TPI to data TPI ratios across the disk surface |
US8031423B1 (en) * | 2009-06-26 | 2011-10-04 | Western Digital Technologies, Inc. | Disk drive generating actual data TPI profile by combining segments of predetermined data TPI profiles |
KR101970807B1 (ko) * | 2012-08-20 | 2019-04-19 | 사빅 글로벌 테크놀러지스 비.브이. | 근적외선 분광법 및 케모메트릭스를 이용한 공정 스크러버 내의 부식제의 실시간 온라인 결정 |
US9127127B2 (en) | 2012-10-03 | 2015-09-08 | Sabic Global Technologies B.V. | Polyetherimide compositions, methods of manufacture, and articles formed therefrom |
US10676571B2 (en) | 2013-12-02 | 2020-06-09 | Sabic Global Technologies B.V. | Polyetherimides with improved melt stability |
EP3408310A1 (en) | 2016-01-29 | 2018-12-05 | SABIC Global Technologies B.V. | Thermoplastic polyimides, method for the manufacture thereof, and articles prepared therefrom |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5202454A (en) * | 1986-07-11 | 1993-04-13 | Societe Nationale Des Poudres Et Explosifs | Process for the manufacture of 1-bromoalkyl hydrocarbyl carbonates |
US5132423A (en) * | 1990-02-05 | 1992-07-21 | General Electric Company | Method for conducting organic reactions using guanidinium salt as phase transfer catalyst |
US5081298A (en) * | 1990-12-12 | 1992-01-14 | General Electric Company | Bis(pentaalkylguanidinium) alkane salts as phase transfer catalysts |
US5229482A (en) * | 1991-02-28 | 1993-07-20 | General Electric Company | Phase transfer catalyzed preparation of aromatic polyether polymers |
US5759406A (en) * | 1994-08-17 | 1998-06-02 | General Electric Company | Adsorption process for organic base recovery from aqueous brine solutions |
-
1996
- 1996-01-11 US US08/583,921 patent/US5872294A/en not_active Expired - Lifetime
- 1996-09-20 SG SG1996010656A patent/SG50763A1/en unknown
-
1997
- 1997-01-09 DE DE69714483T patent/DE69714483T2/de not_active Expired - Fee Related
- 1997-01-09 ES ES97300093T patent/ES2183083T3/es not_active Expired - Lifetime
- 1997-01-09 JP JP00175797A patent/JP4105252B2/ja not_active Expired - Fee Related
- 1997-01-09 EP EP97300093A patent/EP0784051B1/en not_active Expired - Lifetime
-
1998
- 1998-12-17 US US09/216,252 patent/US6235934B1/en not_active Expired - Lifetime
-
2000
- 2000-06-09 US US09/591,426 patent/US6570038B1/en not_active Expired - Fee Related
-
2008
- 2008-02-01 JP JP2008023337A patent/JP4755211B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
SG50763A1 (en) | 1998-07-20 |
JP2008120825A (ja) | 2008-05-29 |
ES2183083T3 (es) | 2003-03-16 |
US5872294A (en) | 1999-02-16 |
JPH09328461A (ja) | 1997-12-22 |
JP4105252B2 (ja) | 2008-06-25 |
EP0784051B1 (en) | 2002-08-07 |
US6570038B1 (en) | 2003-05-27 |
US6235934B1 (en) | 2001-05-22 |
EP0784051A1 (en) | 1997-07-16 |
DE69714483D1 (de) | 2002-09-12 |
DE69714483T2 (de) | 2003-04-10 |
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