CN1118503C - 四苯基鏻式酚盐的液体配制物的制备方法 - Google Patents

四苯基鏻式酚盐的液体配制物的制备方法 Download PDF

Info

Publication number
CN1118503C
CN1118503C CN99803916A CN99803916A CN1118503C CN 1118503 C CN1118503 C CN 1118503C CN 99803916 A CN99803916 A CN 99803916A CN 99803916 A CN99803916 A CN 99803916A CN 1118503 C CN1118503 C CN 1118503C
Authority
CN
China
Prior art keywords
catalyst
liquid
preparation
tetraphenylphosphonium
phenoxides
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 - Fee Related
Application number
CN99803916A
Other languages
English (en)
Other versions
CN1292806A (zh
Inventor
A·科尼格
M·普雷恩
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Carcoustics Techconsult GmbH
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of CN1292806A publication Critical patent/CN1292806A/zh
Application granted granted Critical
Publication of CN1118503C publication Critical patent/CN1118503C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • C08G64/307—General preparatory processes using carbonates and phenols
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/235—Metal derivatives of a hydroxy group bound to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/49—Esterification or transesterification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明涉及一种催化剂配制物，其在室温下为液体，且包含四苯基鏻式酚盐和苯酚。本发明也涉及所述催化剂配制物作为酯交换催化剂的用途，特别是用于不使用溶剂情况下的热塑性聚碳酸酯的制备。

Description

四苯基鏻式酚盐的液体配制物的制备方法
本发明涉及一种四苯基鏻式酚盐和苯酚的催化剂配制物，该配制物在室温下为液体，及其作为酯基转移催化剂的用途，特别是用于热塑性聚碳酸酯的无溶剂制备。
鏻式酚盐的制备方法由DE-OS 19635656和德国专利申请P19727351.3中已知。尤其从US-PS 3.442.854中已知的是，鏻式酚盐和视具体情况而定共同使用的碱金属/碱土金属化合物是特别适合用作酯化反应和酯基转移反应的催化剂，特别是用于通过熔融酯基转移方法制备聚碳酸酯。由于在固体形式的催化剂中计量存在技术上的困难，因此需要在液体形式的催化剂中进行计量。例如，催化剂能够被溶解于液体苯酚中，即在高于45℃的温度，一般在约60℃，且能够以溶液形式被加入到工艺中。这需要加热的压缩空气贮罐并因而需要额外的技术投资。也从J.Org.Chem. 32(1967)1060中已知，鏻式酚盐是热不稳定的，以致于特别是催化剂溶液在受热压缩空气贮罐中经过长的停留时间而无法避免其受热预先破坏。由苯酚和水的混合物(在室温下为液体)(90wt％：10wt％)的计量提供了另一可能性。这里缺点是水作为附加物质被引入到工艺中。Liebigs Ann.Chem.vol.634(1960)1另外描述了季鏻盐在碱存在下分解成氧化三苯基膦。根据我们的研究，高温下少量的水也具有使四苯基鏻式酚盐(TPP-P)分解成氧化三苯基膦的作用。
因而本发明的目的是提供一种四苯基鏻式酚盐的液体计量的简易可行性。目前已经发现TPP-P或TPP-P与2分子苯酚的加合物(下文称为TPP-P*2PhOH)与苯酚以组成为28～45wt％TPP-P(或40-65wt％TPP-P*2PhOH)和对应的72～55wt％(或60～35wt％)苯酚的混合物在室温下是液体。这使得能够以液体形式加入催化剂，而无需外来物质或添加剂且无需预先使催化剂受热。
按照本发明获得的四苯基鏻式酚盐的液体配制物能够以本身已知的方式用作制备芳族聚碳酸酯的催化剂(参见例如US-PS 3,442,854)。按照其公开的熔融酯基转移方法，例如，芳族聚碳酸酯由芳族二酚、碳酸二芳基酯和视具体情况而定的支化剂和/或一元酚类制备。
按照本发明制备的鏻式酚盐能够被用作酯基转移催化剂，其用量是每摩尔二酚10-1mol～10-8mol，优选10-3mol～10-7mol。
熔融酯基转移方法在文献中有更详细描述，(参见例如HermannSchnell，Chemistry and Physics of Polycarbonates，PolymerReviews，9卷，1964，44-51页，DE-AS 1031512，US-PS 3022272，US-PS5340905和US-PS 5399659)。
用本发明的TPP-P液体配制物制备的热塑性聚碳酸酯是无溶剂的，具有浅的固有颜色，且基本上不含聚碳酸酯中不希望的缺陷。在本发明方法的范围内，基本上不含聚碳酸酯中不希望的缺陷指的是聚碳酸酯中下式(I)的支化剂的含量不超过300ppm的数值(根据总的水解和HPLC测定)：
Figure C9980391600041
其中
X＝C1-C9-亚烷基(RCH＝)或亚环烷基，S或单键和
(R)n＝每种情况下相互独立地是COOH、CH3、Cl或Br，其中几个不同的(R)n也能够存在于一个苯环上
n＝0，1，2或3。
实施例
各种苯酚/TPP-P*2PhOH混合物的制备
在N2气氛下，按照表1的组成将苯酚和TPP-P*2PhOH称重(每种情况中总的重量是10g)加入到20ml卷边瓶中，该瓶装有磁力搅拌器并用隔板密封。这些瓶固定在自动振动装置中，并浸入可加热的水浴中。将水浴的温度逐步升高(5℃/h)直到混合物呈液体形式，同时振动装置确保最佳的混合。熔融后，将试样从水浴中取出，并冷却到室温。试样4a、5、6和7保持液态，其它的形成固体和液相，或固化。所有试样的熔融温度(T熔融)都总结于表1中。这些通过一种方法测定，其中已经熔融并冷却到室温的试样通过水浴加热(5℃/h)直到它们又呈液体形式。
表1
催化剂配制物的组成和它们的熔点
试样号码 PhOH[Gew.-％] TPP-P[Gew.-％] PhOH(g) TPP-P*2PhOH(g) T熔融[℃]
1 100 0 10.00 0.00 42
2 85 15 7.86 2.14 39
3 80 20 7.14 2.86 34
4 75 25 6.43 3.57 28
4a 72 28 6.00 4.00 ≤23
5 70 30 5.71 4.29 ≤15
6 60 40 4.29 5.71 ≤15
7 55 45 3.57 6.43 ≤18
8 50 50 2.86 7.14 52
9 40 60 1.43 8.57 90
10 30 70 0.00 10.00 143
用途实施例
用液体TPP-P*2PhOH/PhOH催化剂溶液制备熔融聚碳酸酯
实施例1
将114.15g(0.500mol)的双酚A和113.54g(0.530mol)的碳酸二苯酯称重加入到装有搅拌器、内置温度计和带桥的Vigreux柱(30cm，敷金属的)500ml三颈烧瓶中。通过施加真空并用氮气吹扫(3次)使设备避免与大气氧接触，将混合物加热到150℃。然后加入以6号液体混合物形式的基于双酚A的4×10-3mol％四苯基鏻式酚盐，并在100毫巴下蒸馏出形成的苯酚。同时，将温度升高到250℃。逐步提高真空度使之降到1毫巴，并将温度升高到260℃。然后将温度升高到300℃，在0.1毫巴下将混合物搅拌1.5小时。获得相对溶液粘度为1.260(二氯甲烷，25℃，5g/l)的浅色无溶剂聚碳酸酯。所得聚碳酸酯中式(Ia)的支化剂的含量是25ppm。聚碳酸酯的酚OH值是70ppm。
Figure C9980391600061
实施例2
如实施例1，只是使用5号催化剂溶液。获得相对溶液粘度为1.275(二氯甲烷，25℃，5g/l)的浅色无溶剂聚碳酸酯。所得聚碳酸酯中式(Ia)的支化剂的含量是18ppm。聚碳酸酯的酚OH值是55ppm。

Claims (4)

1.在室温下为液体的催化剂配制物，其包含28-45wt％的四苯基鏻式酚盐和72-55wt％的苯酚。
2.权利要求1的催化剂配制物用作酯基转移催化剂的用途。
3.权利要求2的用途，其特征在于催化剂配制物的用量是0.01-100,000ppm。
4.由芳族二酚、碳酸二芳基酯和任选的支化剂和/或一元酚类起始制备热塑性无溶剂聚碳酸酯的方法，其特征在于权利要求1的催化剂配制物作为酯基转移催化剂的用量是每摩尔二酚10-1-10-8mol。
CN99803916A 1998-03-12 1999-03-01 四苯基鏻式酚盐的液体配制物的制备方法 Expired - Fee Related CN1118503C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19810745.5 1998-03-12
DE19810745A DE19810745C2 (de) 1998-03-12 1998-03-12 Flüssige Katalysatorformulierung aus Tetraphenylphosphoniumphenolat und Phenol und deren Verwendung

Publications (2)

Publication Number Publication Date
CN1292806A CN1292806A (zh) 2001-04-25
CN1118503C true CN1118503C (zh) 2003-08-20

Family

ID=7860644

Family Applications (1)

Application Number Title Priority Date Filing Date
CN99803916A Expired - Fee Related CN1118503C (zh) 1998-03-12 1999-03-01 四苯基鏻式酚盐的液体配制物的制备方法

Country Status (10)

Country Link
US (1) US6291630B1 (zh)
EP (1) EP1062262B1 (zh)
JP (1) JP4577983B2 (zh)
KR (1) KR20010041784A (zh)
CN (1) CN1118503C (zh)
AU (1) AU2931499A (zh)
BR (1) BR9908625A (zh)
DE (2) DE19810745C2 (zh)
ES (1) ES2209409T3 (zh)
WO (1) WO1999046315A1 (zh)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19727351C1 (de) * 1997-06-27 1999-02-11 Bayer Ag Verfahren zur Herstellung von Phosphoniumphenolaten
DE10122496A1 (de) 2001-03-26 2002-10-10 Bayer Ag Polycarbonat mit geringem Scherentzähungsverhalten
DE10149042A1 (de) * 2001-10-05 2003-04-17 Bayer Ag Herstellung von Polyestercarbonaten
DE10219027A1 (de) * 2002-04-29 2003-11-06 Bayer Ag Verfahren zur Herstellung einer flüssigen Formulierung von Phosphoniumphenolaten
US6861499B2 (en) * 2003-02-24 2005-03-01 Triton Systems, Inc. Branched polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto
US20040167283A1 (en) * 2003-02-24 2004-08-26 Michael Vinciguerra Linear polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto
US7560525B2 (en) * 2004-04-02 2009-07-14 Frx Polymers, Llc Crystalline polyphosphonates and methods related thereto
US7569717B2 (en) * 2005-07-19 2009-08-04 Frx Polymers, Llc Diaryl alkylphosphonates and method for preparing same
US7645850B2 (en) * 2005-08-11 2010-01-12 Frx Polymers, Inc. Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same
US7666932B2 (en) * 2005-10-17 2010-02-23 Frx Polymers, Inc. Compositions comprising polyphosphonates and additives that exhibit an advantageous combination of properties, and methods related thereto
CN101291942B (zh) * 2005-10-18 2012-05-30 Frx聚合物有限责任公司 烷基膦酸二芳基酯及其制备方法
US7838604B2 (en) * 2005-12-01 2010-11-23 Frx Polymers, Inc. Method for the production of block copolycarbonate/phosphonates and compositions therefrom
US7928259B2 (en) 2008-02-12 2011-04-19 Frx Polymers, Inc. Diaryl alkylphosphonates and methods for preparing same
US7671165B2 (en) * 2008-05-16 2010-03-02 Sabic Innovative Plastics Ip B.V. Method of forming polycarbonate
US20110237695A1 (en) * 2010-03-23 2011-09-29 Clariant International Ltd. Flame Retardant Combinations For Polyester Elastomers And Flame Retarded Extrusion Or Molding Compositions Therefrom
WO2011120198A1 (en) * 2010-04-01 2011-10-06 Bayer Materialscience Ag Melt polycarbonate having improved heat ageing resistance and manufacturing method thereof
CN104379651B (zh) 2012-05-24 2016-10-26 沙特基础全球技术有限公司 改善的阻燃剂聚合物组合物
DE102012022482A1 (de) 2012-11-19 2014-05-22 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Polymerzusammensetzung mit verbesserter Langzeitstabilität, hieraus hergestellte Formteile sowie Verwendungszwecke
EP2743299A1 (de) 2012-12-12 2014-06-18 Zylum Beteiligungsgesellschaft mbH & Co. Patente II KG Synergistische Zusammensetzung und deren Verwendung als Flammschutzmittel
TW201439222A (zh) 2013-01-22 2014-10-16 Frx Polymers Inc 含磷環氧化合物及源自其之組成物
DE102013005307A1 (de) 2013-03-25 2014-09-25 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von organischen Oxyimiden als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffzusammensetzung und hieraus hergestelltem Formteil
DE102014210214A1 (de) 2014-05-28 2015-12-03 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von Oxyimid-enthaltenden Copolymeren oder Polymeren als Flammschutzmittel, Stabilisatoren, Rheologiemodifikatoren für Kunststoffe, Initiatoren für Polymerisations- und Pfropfprozesse, Vernetzungs- oder Kopplungsmittel sowie solche Copolymere oder Polymere enthaltende Kunststoffformmassen
DE102014211276A1 (de) 2014-06-12 2015-12-17 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von Hydroxybenzotriazol-Derivaten und/oder Hydroxy-Indazol-Derivaten als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffformmasse
DE102014218811A1 (de) 2014-09-18 2016-03-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von phosphorhaltigen organischen Oxyimiden als Flammschutzmittel, Radikalgeneratoren und/oder als Stabilisatoren für Kunststoffe, flammgeschützte Kunststoffzusammensetzung, Verfahren zu deren Herstellung sowie Formteile, Lacke und Beschichtungen
DE102014218810B3 (de) 2014-09-18 2016-01-28 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von organischen Oxyimidsalzen als Flammschutzmittel, flammengeschützte Kunststoffzusammensetzung, Verfahren zur ihrer Herstellung sowie Formteil, Lack oder Beschichtung
DE102017212772B3 (de) 2017-07-25 2018-01-25 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Halogenfreie Sulfonsäureester und/oder Sulfinsäureester als Flammschutzmittel in Kunststoffen, diese enthaltende Kunststoffzusammensetzungen und deren Verwendung
DE102019210040A1 (de) 2019-07-08 2021-01-14 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von phenolisch substituierten Zuckerderivaten als Stabilisatoren, Kunststoffzusammensetzung, Verfahren zur Stabilisierung von Kunststoffen sowie phenolisch substituierte Zuckerderivate
DE102021205168A1 (de) 2021-05-20 2022-11-24 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Verwendung mindestens einer Schwefel enthaltenden Aminosäure zur Stabilisierung von thermoplastischen Kunststoff-Recyclaten, stabilisiertes thermo-plastisches Kunststoffrecyclat, Stabilisatorzusammensetzung, Masterbatch sowie Formmasse bzw. Formteil
DE102021212696A1 (de) 2021-11-11 2023-05-11 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Stabilisatoren auf Basis von Syringasäure, Vanillinsäure, lsovanillinsäure oder 5-Hydroxyveratrumsäure, Kunststoffzusammensetzung, Verfahren zur Stabiliserung einer Kunststoffzusammensetzung sowie Stabilisatorzusammensetzung
DE102022201632A1 (de) 2022-02-16 2023-08-17 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Polymere Stabilisatoren auf Basis von Syringasäure, Vanillinsäure, lsovanillinsäure oder 5-Hydroxyveratrumsäure, Kunststoffzusammensetzung, Verfahren zur Stabiliserung einer Kunststoffzusammensetzung sowie Stabilisatorzusammensetzung

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3022272A (en) 1962-02-20 Process for the production of high
DE1031512B (de) 1955-12-21 1958-06-04 Bayer Ag Verfahren zur Herstellung von hochmolekularen faser- und filmbildenden Polycarbonaten
DE1274578B (de) * 1965-01-21 1968-08-08 Bayer Ag Verfahren zur Herstellung von Cycloalkylaminverbindungen
US4302574A (en) 1979-05-23 1981-11-24 The Dow Chemical Company Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
DE4238123C2 (de) 1992-11-12 2000-03-09 Bayer Ag Verfahren zur Herstellung von thermoplastischen Polycarbonaten
DE4312390A1 (de) 1993-04-16 1994-10-20 Bayer Ag Zweistufen-Verfahren zur Herstellung von thermoplastischem Polycarbonat
DE19612139A1 (de) 1996-03-27 1997-10-02 Bayer Ag Zweistufenverfahren zur Herstellung von thermoplastischem Polycarbonat
JPH107784A (ja) * 1996-06-26 1998-01-13 Idemitsu Kosan Co Ltd ポリカーボネートの製造方法
SG53043A1 (en) 1996-08-28 1998-09-28 Ciba Geigy Ag Molecular complex compounds as photoinitiators
EP0826693A1 (de) * 1996-09-03 1998-03-04 Bayer Ag Verfahren zur Herstellung von Phosponiumphenolaten
DE19723524A1 (de) * 1996-09-03 1998-03-05 Bayer Ag Verfahren zur Herstellung von Phosphoniumphenolaten
JP3944943B2 (ja) * 1997-04-15 2007-07-18 宇部興産株式会社 炭酸ジアルキルの製造法
DE19727351C1 (de) * 1997-06-27 1999-02-11 Bayer Ag Verfahren zur Herstellung von Phosphoniumphenolaten

Also Published As

Publication number Publication date
JP2002506098A (ja) 2002-02-26
DE59907196D1 (de) 2003-11-06
WO1999046315A1 (de) 1999-09-16
BR9908625A (pt) 2000-11-14
US6291630B1 (en) 2001-09-18
CN1292806A (zh) 2001-04-25
EP1062262B1 (de) 2003-10-01
ES2209409T3 (es) 2004-06-16
HK1036292A1 (zh) 2001-12-28
JP4577983B2 (ja) 2010-11-10
DE19810745A1 (de) 1999-09-16
EP1062262A1 (de) 2000-12-27
KR20010041784A (ko) 2001-05-25
DE19810745C2 (de) 2000-05-04
AU2931499A (en) 1999-09-27

Similar Documents

Publication Publication Date Title
CN1118503C (zh) 四苯基鏻式酚盐的液体配制物的制备方法
CN1154682C (zh) 改性聚碳酸酯的生产方法
DE60205385T2 (de) Verfahren zur herstellung von polycarbonat
US7115700B2 (en) Method of polycarbonate preparation
EP1567577B1 (en) Method for making stable, homogeneous melt solutions
JP3122577B2 (ja) 溶融縮合されたポリカーボネート樹脂およびその改良製造法
EP1360220B1 (en) Process for the production of polycarbonate
US4016190A (en) Process for the preparation of diarylcarbonates
CN1280335C (zh) 降低聚碳酸酯树脂中反应副产物的方法
CN1556785A (zh) 制备酯取代的碳酸二芳基酯的界面方法
US6797802B2 (en) Method of polycarbonate preparation
US5767224A (en) Two-step process for the production of thermoplastic polycarbonate
JP2000186137A (ja) ポリカーボネート及び光学材料
EP0584801A2 (en) Aromatic polycarbonate resins and process for the preparation thereof
HK1036292B (zh) 四苯基鏻式酚盐的液体配制物的制备方法
US6414106B1 (en) Process for the neutralization of residual acid species in crude dihydric phenols
JP4636705B2 (ja) ポリカーボネートの製造方法
JP3386288B2 (ja) 芳香族ポリカーボネートの製造方法
JP2002220456A (ja) ポリカーボネートの製造方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
ASS Succession or assignment of patent right

Owner name: CARCOUSTICS TECHCONSULT GMBH

Free format text: FORMER OWNER: BAYER AKTIENGESELLSCHAFT

Effective date: 20120802

C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

Effective date of registration: 20120802

Address after: Germany Leverkusen

Patentee after: Carcoustics Techconsult GmbH

Address before: Germany Leverkusen

Patentee before: Bayer Aktiengesellschaft

EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20010425

Assignee: Bayer Material Science (China) Co., Ltd.

Assignor: Carcoustics Techconsult GmbH

Contract record no.: 2012990000854

Denomination of invention: Preparation method of four phenyl phenol type salt liquid formulations

Granted publication date: 20030820

License type: Common License

Record date: 20121128

LICC Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20030820

Termination date: 20150301

EXPY Termination of patent right or utility model