CN108384004A - 用于制备聚酰胺酰亚胺的方法 - Google Patents

用于制备聚酰胺酰亚胺的方法 Download PDF

Info

Publication number
CN108384004A
CN108384004A CN201711278083.0A CN201711278083A CN108384004A CN 108384004 A CN108384004 A CN 108384004A CN 201711278083 A CN201711278083 A CN 201711278083A CN 108384004 A CN108384004 A CN 108384004A
Authority
CN
China
Prior art keywords
proton
solvent
dialkyl amide
cosolvents
amide solvent
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.)
Pending
Application number
CN201711278083.0A
Other languages
English (en)
Inventor
约翰·思登斯迪克
大卫·诺格
凯瑟琳·穆林斯
梅斯·菲利普斯
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.)
Dalton Of LLC
Original Assignee
Dalton Of LLC
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 Dalton Of LLC filed Critical Dalton Of LLC
Publication of CN108384004A publication Critical patent/CN108384004A/zh
Pending 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
    • 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
    • C08G73/14—Polyamide-imides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明涉及用于制备聚酰胺酰亚胺的方法。本发明公开了一种用于制备聚酰胺酰亚胺的方法，所述方法包括：利用至少一种非质子二烷基酰胺溶剂，其中，所述至少一种非质子二烷基酰胺溶剂是N‑甲酰基吗啉；其中，所述至少一种非质子二烷基酰胺溶剂与其他的工艺助溶剂的摩尔比为19:1至1:1；并且其中，所述其他的工艺助溶剂选自由水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N‑甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺构成的组。

Description

用于制备聚酰胺酰亚胺的方法
本申请是申请日为2012年12月17日、申请号为201280061393.6、发明名称为“用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备”的中国专利申请的分案申请。
优先权
本专利申请要求2011年12月15日递交的标题为“Low Toxicity Solvent Systemfor Polyamidimide Resins and Solvent System Manufacture”的第61/576,247号的相应临时专利申请的优先权，且以引用的方式并入本文。
技术领域
本发明的实施方式涉及溶剂的领域；更具体地，本发明的实施方式涉及溶剂以及它们在制备聚酰胺酰亚胺中的用途。
背景技术
聚酰胺酰亚胺(PAI)聚合物由于其优异的耐热性和高强度而用于多种高性能的涂料用途。合成以便于制备涂料的形式的聚酰胺酰亚胺聚合物的主要途径是：使二异氰酸酯(通常是4,4’-亚甲基二苯基二异氰酸酯(MDI))与偏苯三酸酐(TMA)反应。在该方法中，PAI聚合物通常在极性非质子溶剂中合成，例如，该极性非质子溶剂包括二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮(NMP)、N-乙基吡咯烷酮的N-甲基酰胺化合物。例如，参见第2,421,021号、第3,260,691号、第3,471,444号、第3,518,230号、第3,817,926号、和第3,847,878号的美国专利。在该合成路径中获得的典型的聚合物固体含量是35％至45％，根据涂料应用的最终用途，其可以采用稀释剂进一步稀释。
替选的溶剂(如，四氢呋喃、甲基乙基酮、γ-丁内酯、或二甲亚砜)具有如下缺点：例如，对于用作反应溶剂而言沸点太低、聚合物溶解度低、或存储稳定性差，这些缺点会改变聚合物树脂的应用性能。
第4,950,700号美国专利和第5,095,070号美国专利列举了γ-丁内酯与N-甲基酰胺助溶剂和二羟甲基亚乙基脲作为替代溶剂合成PAI树脂的实例。然而，γ-丁内酯具有使其受制于法规且不适于在配方中一般用途的神经系统属性。二羟甲基亚乙基脲还没有进行广泛的毒理学研究，且含有疑似对环境和健康负面影响的N-甲基酰胺官能团。如在第20100076223A1号美国专利申请公开中所描述的那些新溶剂(例如，3-甲氧基-N，N-二甲基丙酰胺)太贵，或还未充分测试长期毒性。
此外，质子溶剂(如，乳酸乙酯和丙二醇)不适于用作PAI反应介质。
在实际应用中，虽然本领域中已知的这些溶剂对于制备PAI是有用的或对于其他有机合成反应是有效的，但还要认识到其毒性方面的问题。因此，利用具有对健康和安全最小影响的合成方法制备聚酰胺酰亚胺聚合物是一个优势。
发明内容
公开了一种用于制备聚酰胺酰亚胺的方法。在一个实施方式中，该方法包括利用至少一种非质子二烷基酰胺溶剂。
在本发明的一个实施方式中，公开了一种用于制备聚酰胺酰亚胺的方法，所述方法包括：利用至少一种非质子二烷基酰胺溶剂，其中，所述至少一种非质子二烷基酰胺溶剂是N-甲酰基吗啉；其中，所述至少一种非质子二烷基酰胺溶剂与其他的工艺助溶剂的摩尔比为19:1至1:1；并且其中，所述其他的工艺助溶剂选自由水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N-甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺构成的组。
在本发明的一个实施方式中，方法还包括：使二异氰酸酯与偏苯三酸酐TMA反应。
在本发明的一个实施方式中，二异氰酸酯是4,4’-亚甲基二苯基二异氰酸酯MDI。
具体实施方式
为了实现更安全的替选方式，特别是不含常用的N-甲基酰胺溶剂的合成途径，替选的更低毒性的溶剂是必要的。乙酰胺受到关注是因为：乙酰胺具有较低的毒性且易于由工业上可利用的二烷基胺制备，以及具有长期的低的慢性毒性。特别地，二烷基酰胺是有用的。低毒性的溶剂N-乙酰基吗啉(NAM)已被发现可适用于制备聚酰胺酰亚胺树脂。本发明的其他有用的、低毒性的溶剂为二乙基乙酰胺(DEAc)、二-n-丙基乙酰胺、N-甲酰基吗啉、二乙酰基哌嗪、N,N-二异丙基乙酰胺(DIPAc)、二-n-丁基乙酰胺(DIBAc)、二-n-丙基乙酰胺(DIPA)、和N-丙酰基吗啉(NPM)。为了实现更低的毒性方法，现已发现，PAI的合成可通过单独地或彼此组合的方式利用本发明的非质子二烷基酰胺溶剂，或借助于提供独特溶剂系统的助溶剂来完成。例如，对于PAI的各种工业应用，会需要使用溶剂的组合，其中，希望得到在特定范围内的粘度。此外，这些溶剂还可充当稀释剂。为了实现这点，二烷基酰胺溶剂的组合可用来获得所期望的粘度。其他优选的可用于合成PAI树脂或用作溶解PAI树脂的稀释剂的具有低毒性的助溶剂为：水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N-甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺。
还已发现，本发明的实施方式的另一优点是：通过在合成方法中利用一种或多种非质子二烷基酰胺，一锅法两步反应是可以的。
此外，由于用于合成PAI树脂的现有技术的溶剂(如N-甲基酰胺)的毒性，故避免这些化合物的使用。
特别地，非质子二烷基酰胺与其他的工艺助溶剂的优选摩尔比为大约19:1至大约1:1。更优选的比例为大约80:20至大约70:30。最优选的比例为大约78:22。
实施例：
实施例1-合成助溶剂系统的方法：向1L的配备有温度计、冷凝器和机械搅拌器的四颈烧瓶中加入200g的二乙胺。在保持低于55℃的温度的同时，加入279.16g的乙酸酐。然后加入250.15g的吗啉。反应被加热至大约130℃，直到乙酸被耗尽(大约8小时)。通过蒸馏水/过量的吗啉来提高转化率。
实施例2(KM-1145)：装入51g的N-乙酰基吗啉(NAM)、0.85g的己内酰胺、19.8g的MDI、15.65g的TMA，然后加热至100℃。溶液在96℃下保持1.5小时。在一整夜后，温度降至70℃，然后加热至130℃，保持1.25小时。粘度太高；加入12.2g的来自实施例1的NAM助溶剂。
固体％＝33.82％，粘度(DVII，23℃)＝63000cps。
实施例3(JES-3-29)：装入1.68g的己内酰胺、31.49g的TMA、39.66g的MDI和102.12g的来自实施例1的NAM助溶剂，然后在1.5小时内加热至110℃。加热至130℃，监测粘度，直到粘度大于2000cps/120℃(约7小时)。冷却至低于80℃，加入来自实施例1的NAM助溶剂，保持搅拌。在保持90℃的温度下，缓慢地加入TEA(三乙胺)。在大于60℃的温度下保持1小时至2小时。加入水以调节至大约28％的固体。加热、保持在85℃，通过TEA和水调节pH值大于8，根据需要以获得均一性。
实施例4(KM277)：250mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：57.6g的N-乙酰基吗啉、18.9g的邻二甲苯、1.3g的己内酰胺、29.7g的亚甲基二苯基二异氰酸酯、和23.5g的偏苯三酸酐。反应被加热至90℃，保持2小时。然后，反应温度被加热至130℃保持5小时，然后，加入14.7g的N-乙酰基吗啉和3.68g的邻二甲苯，反应器被冷却至室温。利用DVII博勒菲(Brookfield)粘度仪，在23℃下，最终粘度为13834cps。
实施例5(MP-2-11)：250mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：49g的N-乙酰基吗啉、18.9g的二乙基乙酰胺、1.3g的邻二甲苯、29.7g的亚甲基二苯基二异氰酸酯、和23.6g的偏苯三酸酐。反应被加热至90℃保持2小时。然后，反应温度加热至130℃保持3小时，然后，加入3.74g的N-乙酰基吗啉，反应器被冷却至60℃。然后，逐滴加入14.7g的丙酮，反应器被冷却至室温。利用DVII博勒菲粘度仪，在23℃下，最终粘度为3076cps。
实施例6(KM38)：500mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：121g的N-乙酰基吗啉、52.9g的亚甲基二苯基二异氰酸酯、和40.92g的偏苯三酸酐。反应被加热至88℃保持3小时。然后，反应温度被加热至120℃，直到淬火粘度达到1680cps(约2.5小时)，然后，加入41.81g的N-甲酰基吗啉和41.81g的邻二甲苯以淬火冷却反应。反应器被冷却至室温。利用DVII博勒菲粘度仪，在23℃下，最终粘度为8573cps。
实施例7(JES-4-21)：50.27g的亚甲基二苯基二异氰酸酯、38.62g的偏苯三酸酐、和206.56g的N-甲酰基吗啉被装入400mL的烧杯中。反应混合物被加热至80℃，直到通过失重逐步生成大约1当量的CO2。然后，反应温度被加热至130℃，直到骤冷粘度达到730cps，然后，加入41.51g的额外的N-甲酰基吗啉，以骤冷反应。反应器被冷却至室温。最终固体含量被分析为26.02％，最终粘度为10264cps(利用DVII博勒菲粘度仪)。
然而，本领域的普通技术人员在阅读前述说明书之后，本发明的多个变更和变型对于本领域的普通技术人员来说将毫无疑问是显而易见的，应该理解，以实例说明的任何示出和描述的具体实施方式不应该视为限制。因此，引用的多个实施方式的细节不旨在限制权利要求书的范围，它们本身仅提到被视为本发明必要技术特征的那些特征。

Claims (3)

1.一种用于制备聚酰胺酰亚胺的方法，所述方法包括：利用至少一种非质子二烷基酰胺溶剂，其中，所述至少一种非质子二烷基酰胺溶剂是N-甲酰基吗啉；
其中，所述至少一种非质子二烷基酰胺溶剂与其他的工艺助溶剂的摩尔比为19:1至1:1；和
其中，所述其他的工艺助溶剂选自由水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N-甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺构成的组。
2.如权利要求1所述的方法，所述方法还包括：使二异氰酸酯与偏苯三酸酐TMA反应。
3.如权利要求2所述的方法，其中，所述二异氰酸酯是4,4’-亚甲基二苯基二异氰酸酯MDI。
CN201711278083.0A 2011-12-15 2012-12-17 用于制备聚酰胺酰亚胺的方法 Pending CN108384004A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161576247P 2011-12-15 2011-12-15
US61/576,247 2011-12-15
CN201280061393.6A CN104144968A (zh) 2011-12-15 2012-12-17 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201280061393.6A Division CN104144968A (zh) 2011-12-15 2012-12-17 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备

Publications (1)

Publication Number Publication Date
CN108384004A true CN108384004A (zh) 2018-08-10

Family

ID=48613287

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201280061393.6A Pending CN104144968A (zh) 2011-12-15 2012-12-17 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备
CN201711278083.0A Pending CN108384004A (zh) 2011-12-15 2012-12-17 用于制备聚酰胺酰亚胺的方法

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201280061393.6A Pending CN104144968A (zh) 2011-12-15 2012-12-17 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备

Country Status (8)

Country Link
US (1) US9751986B2 (zh)
EP (1) EP2791208B1 (zh)
JP (1) JP6087373B2 (zh)
CN (2) CN104144968A (zh)
ES (1) ES2641464T3 (zh)
IN (1) IN2014DN05779A (zh)
SG (1) SG11201403244WA (zh)
WO (1) WO2013090933A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110258118A (zh) * 2019-07-12 2019-09-20 开封大学 水溶性耐温型碳纤维上胶剂及其制备方法

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9751986B2 (en) 2011-12-15 2017-09-05 Fujifilm Hunt Chemicals Us, Inc. Low toxicity solvent system for polyamideimide resins and solvent system manufacture
US9029441B2 (en) * 2011-12-15 2015-05-12 Fujifilm Hunt Chemicals Us, Inc. Low toxicity solvent system for polyamideimide and polyamide amic acid resins and coating solutions thereof
WO2015024824A1 (de) * 2013-08-23 2015-02-26 Basf Se Verfahren zur herstellung von polyamidimiden unter verwendung von n-formylmorpholin
DE102014104223A1 (de) * 2014-03-26 2015-10-01 Elantas Italia S.R.L. Neues Lösemittel für Polyamidimide und Polyimide
US9725617B2 (en) * 2014-04-17 2017-08-08 Fujifilm Hunt Chemicals U.S.A., Inc. Low toxicity solvent system for polyamideimide and polyamide amic acid resin coating
US9815941B2 (en) * 2014-04-17 2017-11-14 Cymer-Dayton, Llc Low toxicity solvent system for polyamdieimide and polyamide amic acid resin manufacture
FR3022553A1 (fr) * 2014-06-20 2015-12-25 Seb Sa Composition de primaire en phase aqueuse via des polymeres heterocycliques sous forme de poudres obtenues par broyage
CN107429056B (zh) * 2015-04-30 2021-06-08 昭和电工材料株式会社 聚酰胺酰亚胺树脂组合物及涂料
EP3319736A4 (en) * 2015-07-10 2019-03-13 Whitford Corporation COMPOSITION FOR FORMING HIGH-RELEASE, LOW FRICTION FUNCTIONAL COATINGS
JP6837478B2 (ja) * 2015-09-25 2021-03-03 ハンツマン・アドヴァンスト・マテリアルズ・ライセンシング・（スイッツランド）・ゲーエムベーハー ポリアミドイミドの製造
WO2017099030A1 (ja) * 2015-12-07 2017-06-15 日立化成株式会社 ポリアミドイミド樹脂組成物及びフッ素塗料
JP6822416B2 (ja) * 2015-12-14 2021-01-27 昭和電工マテリアルズ株式会社 ポリアミドイミド樹脂及び塗料
US10301506B2 (en) * 2016-06-06 2019-05-28 Cymer-Dayton, Llc Full scale process for preparing polymer powders
WO2018002988A1 (ja) * 2016-06-27 2018-01-04 日立化成株式会社 ポリアミドイミド樹脂組成物及び塗料
EP3590992A4 (en) * 2017-03-01 2020-10-28 Hitachi Chemical Company, Ltd. POLYAMIDIMIDE RESIN AND USE THEREOF
JP7251478B2 (ja) * 2017-08-01 2023-04-04 株式会社レゾナック ポリアミドイミド樹脂組成物及びフッ素塗料
JP7226507B2 (ja) * 2017-08-01 2023-02-21 株式会社レゾナック ポリアミドイミド樹脂組成物、フッ素塗料、及び導電性組成物
JP2021526508A (ja) * 2018-06-14 2021-10-07 シーイーエム コーポレイション 固相ペプチド合成のための溶媒系
KR20230052939A (ko) 2020-09-22 2023-04-20 엘란타스 유럽 에스.알.엘. 폴리아미드이미드를 포함하는 와이어 에나멜 조성물
CN115926163A (zh) * 2022-12-21 2023-04-07 开封夸克新材料有限公司 一种水性聚酰胺酰亚胺树脂分散液及其制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790530A (en) * 1971-11-03 1974-02-05 Phelps Dodge Magnet Wire Corp Method of making amide-imide resins,aromatic amides and aromatic polyamide resins
US4004062A (en) * 1974-06-03 1977-01-18 General Electric Company Aqueous polyester coating composition
US4003947A (en) * 1974-06-03 1977-01-18 General Electric Company Coating composition and method of coating substrates therewith
US4189518A (en) * 1969-05-08 1980-02-19 General Electric Company Cured polymeric coating material, coated substrate, and process of forming
US5756647A (en) * 1996-01-25 1998-05-26 Ems-Inventa Ag Process for activated anionic lactam polymerization
US20090208868A1 (en) * 2005-07-14 2009-08-20 Mitsui Chemicals , Inc. Positive photosensitive resin composition and method for forming pattern

Family Cites Families (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2421021A (en) 1945-03-02 1947-05-27 Bell Telephone Labor Inc Spot-welding machine
US3346502A (en) 1962-02-09 1967-10-10 Colgate Palmolive Co Bleaching composition
US3260691A (en) 1963-05-20 1966-07-12 Monsanto Co Coating compositions prepared from condensation products of aromatic primary diamines and aromatic tricarboxylic compounds
US3393153A (en) 1965-12-20 1968-07-16 Procter & Gamble Novel liquid bleaching compositions
AU409223B2 (en) 1965-10-07 1970-12-15 Balm Paints Limited Process for preparing copolymers of monoethylenically unsaturated dicarboxylic compounds
US3471444A (en) 1966-02-23 1969-10-07 Gen Electric Polyamide-imides and precursors thereof
US3518230A (en) 1968-01-04 1970-06-30 Schenectady Chemical Imide modified amide imide wire enamel
JPS4831842B1 (zh) 1968-07-04 1973-10-02
GB1273085A (en) 1969-05-12 1972-05-03 Fuji Photo Film Co Ltd Photographic printing paper
US3843587A (en) * 1969-05-16 1974-10-22 Schenectady Chemical Polyamide-imide resins prepared from the reaction of aromatic diisocyanates with mixtures of polycarboxylic acids and anhydrides
US3646015A (en) 1969-07-31 1972-02-29 Procter & Gamble Optical brightener compounds and detergent and bleach compositions containing same
US3817926A (en) 1970-12-14 1974-06-18 Gen Electric Polyamide-imides
US3975345A (en) * 1972-06-23 1976-08-17 General Electric Company Polyamideimides and method for making
US3847878A (en) 1973-04-09 1974-11-12 Standard Oil Co Process for preparation of polyamide-imides and shaped articles of same
US3939109A (en) * 1974-12-19 1976-02-17 Gulf Research & Development Company Polyamic-acids prepared from 3,3,4,4-benzhydrol tetracarboxylic dianhydride
US4003974A (en) 1975-04-04 1977-01-18 E. I. Du Pont De Nemours And Company Continuous spin-drawing process for preparing polyethylene terephthalate yarns
US4098775A (en) * 1976-11-15 1978-07-04 The Upjohn Company Novel polyamideimides
JPS55120628A (en) * 1979-03-13 1980-09-17 Sumitomo Chem Co Ltd Production of aromatic polyamide-imide polymer
DE3020148A1 (de) 1980-05-28 1981-12-03 Bayer Ag, 5090 Leverkusen Konzentrierte mikrokapselsuspensionen fuer reaktionsdurchschreibepapiere
US4408032A (en) 1981-08-03 1983-10-04 Phelps Dodge Industries, Inc. Modified polyamide-imide resins and method for making the same
JPS5880326A (ja) * 1981-11-06 1983-05-14 Hitachi Chem Co Ltd ポリアミドイミド樹脂の製造法
US5103326A (en) 1983-03-30 1992-04-07 Manchester R&D Partnership Fluorescent colored encapsulated liquid crystal apparatus using enhanced scattering
JPS62202783A (ja) 1986-03-03 1987-09-07 Kureha Chem Ind Co Ltd 部分感圧紙
JPH0791366B2 (ja) * 1987-02-25 1995-10-04 東洋紡績株式会社 フレキシブル配線板用耐熱性フィルム
GB2210702B (en) 1987-10-02 1991-11-06 Fuji Photo Film Co Ltd Heat sensitive recording material
US5231117A (en) 1988-01-07 1993-07-27 The Standard Register Company High solids CB printing ink which produces a black image
FR2627497B1 (fr) 1988-02-22 1990-06-15 Rhone Poulenc Fibres Solutions de polyamides-imides et leur procede d'obtention
US5035974A (en) 1988-06-16 1991-07-30 Fuji Photo Film Co., Ltd. Light-image forming material
JPH0254252A (ja) 1988-08-19 1990-02-23 Fuji Photo Film Co Ltd 光像形成材料
FR2636635B1 (fr) 1988-09-21 1992-11-06 Rhone Poulenc Sa Solutions de polyamides-imides et leur procede d'obtention
US5051333A (en) 1989-06-22 1991-09-24 Fuji Photo Film Co., Ltd. Optical image-recording material
US5002924A (en) 1989-10-05 1991-03-26 The Standard Register Company Carbonless copy paper coating containing microencapsulated load bearers
JP2639748B2 (ja) 1990-10-31 1997-08-13 富士写真フイルム株式会社 感光性エレメントおよびその製造法
US5340680A (en) 1992-09-10 1994-08-23 Appleton Papers Inc. Desensitizable record material
JP3720932B2 (ja) 1996-09-18 2005-11-30 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
US6265128B1 (en) 1996-11-15 2001-07-24 Foto-Wear, Inc. Imaging transfer system and process for transferring image and non-image areas thereof to a receptor element
EP0974621B1 (en) 1998-07-21 2002-10-23 DyStar Textilfarben GmbH & Co. Deutschland KG Navy-blue dye mixtures of fiber reactive azo dyes
US7635662B2 (en) 1998-09-04 2009-12-22 Chemipro Kasei Kaisha, Ltd. Compound for color-producing composition, and recording material
US6746984B2 (en) 1999-12-08 2004-06-08 Pentax Corporation Image-forming medium coated with microcapsule layer for forming image
WO2002078970A1 (en) 2001-04-02 2002-10-10 Ciba Specialty Chemicals Holding Inc. Heat sensitive recording material
KR100805134B1 (ko) 2001-07-03 2008-02-21 히다찌 가세이 고오교 가부시끼가이샤 감광성 수지 조성물, 이를 사용한 패턴제조법 및 전자부품
US20030060387A1 (en) 2001-09-20 2003-03-27 Unilever Home And Personal Care, Usa, Division Of Conopco, Inc. Water-soluble package with fluorescent dye in the film
JP2003145945A (ja) 2001-11-16 2003-05-21 Pentax Corp 反応加速バインダー及びこれを用いた画像記録用組成物並びに画像記録シート
US7011922B2 (en) 2003-02-19 2006-03-14 Fuji Photo Film Co., Ltd. Thermal recording material
JP2005042086A (ja) 2003-07-07 2005-02-17 Nitto Denko Corp ポリアミドイミド樹脂、ポリアミドイミド樹脂の製造方法、ポリアミドイミド樹脂組成物、被膜形成材料、及び電子部品用接着剤
WO2005042263A1 (ja) 2003-10-23 2005-05-12 Asahi Kasei Chemicals Corporation 分散液組成物および記録材料
ATE413286T1 (de) 2004-06-11 2008-11-15 Ahlstrom Kauttua Oy Geschichtetes sicherheitsmaterial und herstellungsverfahren dafür
US20070098900A1 (en) 2004-11-05 2007-05-03 Fuji Hunt Photographic Chemicals, Inc. Media providing non-contacting formation of high contrast marks and method of using same, composition for forming a laser-markable coating, a laser-markable material and process of forming a marking
WO2007014847A1 (en) 2005-07-28 2007-02-08 Ciba Specialty Chemicals Holding Inc. Stable aqueous dispersions of colour developer
JP2007099891A (ja) * 2005-10-04 2007-04-19 Hitachi Chem Co Ltd ポリアミドイミド樹脂系耐熱性樹脂組成物、該耐熱性樹脂組成物を用いたシームレス管状体、塗膜、塗膜板及び耐熱性塗料
JP2007152686A (ja) 2005-12-02 2007-06-21 Fujifilm Corp 記録方法
US8338645B2 (en) 2007-02-20 2012-12-25 Idemitsu Kosan Co., Ltd. Method for producing a β-alkoxypropionamide
JP2011231278A (ja) * 2010-04-30 2011-11-17 Hitachi Chem Co Ltd ポリアミドイミド樹脂系シ−ムレス管状体用樹脂組成物及びシ−ムレス管状体
JP5685409B2 (ja) 2010-09-14 2015-03-18 株式会社ヴァレオジャパン ポリアミドイミド系皮膜用塗料
US9029441B2 (en) * 2011-12-15 2015-05-12 Fujifilm Hunt Chemicals Us, Inc. Low toxicity solvent system for polyamideimide and polyamide amic acid resins and coating solutions thereof
US9751986B2 (en) 2011-12-15 2017-09-05 Fujifilm Hunt Chemicals Us, Inc. Low toxicity solvent system for polyamideimide resins and solvent system manufacture

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4189518A (en) * 1969-05-08 1980-02-19 General Electric Company Cured polymeric coating material, coated substrate, and process of forming
US3790530A (en) * 1971-11-03 1974-02-05 Phelps Dodge Magnet Wire Corp Method of making amide-imide resins,aromatic amides and aromatic polyamide resins
US4004062A (en) * 1974-06-03 1977-01-18 General Electric Company Aqueous polyester coating composition
US4003947A (en) * 1974-06-03 1977-01-18 General Electric Company Coating composition and method of coating substrates therewith
US4101487A (en) * 1974-06-03 1978-07-18 General Electric Company Coating medium
US5756647A (en) * 1996-01-25 1998-05-26 Ems-Inventa Ag Process for activated anionic lactam polymerization
US20090208868A1 (en) * 2005-07-14 2009-08-20 Mitsui Chemicals , Inc. Positive photosensitive resin composition and method for forming pattern

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
向明 等: "《胶粘剂基础与配方设计》", 31 January 2002, 化学工业出版社 *
汪多仁 等: "《现代高分子材料生产及应用手册》", 31 May 2002, 中国石化出版社 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110258118A (zh) * 2019-07-12 2019-09-20 开封大学 水溶性耐温型碳纤维上胶剂及其制备方法

Also Published As

Publication number Publication date
WO2013090933A1 (en) 2013-06-20
ES2641464T3 (es) 2017-11-10
EP2791208A4 (en) 2015-07-22
SG11201403244WA (en) 2014-07-30
JP2015522660A (ja) 2015-08-06
US20160002408A1 (en) 2016-01-07
JP6087373B2 (ja) 2017-03-01
CN104144968A (zh) 2014-11-12
EP2791208A1 (en) 2014-10-22
EP2791208B1 (en) 2017-09-06
IN2014DN05779A (zh) 2015-04-10
US9751986B2 (en) 2017-09-05

Similar Documents

Publication Publication Date Title
CN108384004A (zh) 用于制备聚酰胺酰亚胺的方法
Shen et al. Anticorrosive waterborne polyurethane coatings derived from castor oil and renewable diols
Yu et al. Catalyzed non-isocyanate polyurethane (NIPU) coatings from bio-based poly (cyclic carbonates)
US10280335B2 (en) Preparation of polyamide-imide resins using N-formyl morpholine:3-methoxy N,N-dimethylpropanamide
JP5632067B2 (ja) ウレトンイミン変性イソシアネート組成物の製造方法
WO2023039923A1 (zh) 一种半芳香族聚酯及其制备方法和应用
Bullermann et al. Synthesis and characterization of polyurethane ionomers with trimellitic anhydride and dimethylol propionic acid for waterborne self‐emulsifying dispersions
Huang et al. Phenolic fatty acid-based epoxy curing agent for antimicrobial epoxy polymers
Zeng et al. Synthesis, monomer removal, modification, and coating performances of biobased pentamethylene diisocyanate isocyanurate trimers
US11208523B2 (en) Polycarbodiimide compound and thermosetting resin composition
EP2162483B1 (de) Aminogruppenhaltige polyester
Babahan-Bircan et al. Environment-friendly UV-curable alkyd-based non-isocyanate urethanes
CN108003072A (zh) 一种异氰酸酯稳定剂及其制备方法
CN104774310B (zh) 桐油多元醇基可后交联两性聚氨酯及其制备方法
Gaddam et al. Renewable soft segment-induced anionic waterborne polyurethane dispersions with enriched bio-content
CN101434701B (zh) 由端基交换获得的聚酰胺酰亚胺及其制备方法
Taghvaei-Ganjali et al. Application of sulfonamide derivative of calixarene for improvement of mechanical properties and thermal stability of polyurethane composite
CN108047153A (zh) 一种低挥发环状碳化二亚胺类化合物及其制备方法
Rajappan et al. Reversible hetero-Diels–Alder amine hardener as drop-in replacement for healable epoxy coatings
US20200231721A1 (en) Urea terminated butadiene polymers and butadiene acrylonitrile copolymers
US11639450B2 (en) Biobased, non-isocyanate, 2K polyurethane coatings produced from polycarbamate and dialdehyde crosslinking
CN105778083A (zh) 一种聚六亚甲基双胍及其盐的制备方法
Zeimaran et al. Synthesis and characterization of supramolecular elastomers from polyacids composed of vegetable oils
CN106810677B (zh) 高分子量聚乳酸的制备方法、聚合级丙交酯的制备方法
CN114805101A (zh) 一种马来酸二乙酯尾料的回收利用方法

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1257039

Country of ref document: HK

RJ01 Rejection of invention patent application after publication

Application publication date: 20180810

RJ01 Rejection of invention patent application after publication