JP2019210451A - ジシクロペンタジエンを有する官能化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマー及びその製造方法、並びにその用途 - Google Patents
ジシクロペンタジエンを有する官能化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマー及びその製造方法、並びにその用途 Download PDFInfo
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- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
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- C07C43/285—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having unsaturation outside the six-membered aromatic rings
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F112/34—Monomers containing two or more unsaturated aliphatic radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- 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
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- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
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- C08F222/10—Esters
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Abstract
Description
[1] 米国特許公報8,791,214;
[2] 米国特許公報7,329,708;
[3] S. Fisher, H.g., M. Jeevanath, E. Peters, SABIC Innovative Plastics In Polyphenylene ether Macromonomer: X. Vinyl Terminated Telechelic Macromers, 69th Annual Technical Conference of the Society of Plastics Engineers 2011(ANTEC 2011), Boston, Massachusetts, USA, 1−5 May, 2011; pp 2819−2822;
[4] E. N. Peters, A. K., E. Delsman, H.guo, A. Carrillo,g. Rocha In Society of Plastics Engineers Annual Technical Conference(ANTEC 2007): Plastics Encounter, Cincinnati, Ohio., 6−11 May, 2007; Curran Associates, Inc.; pp 2125−2128;
[5] E. N. Peters, S. M. F., H.guo, C. Degonzague, R. Howe. In 68th Annual Technical Conference of the Society of Plastics Engineers 2010(ANTEC 2010), Orlando, Florida, USA., 16−20 May, 2010; Curran Associates, Inc.(Aug 2010 );
[6] Edward N. Peters, S. M. F., Huaguo In Polyphenylene ether Macromonomers. XI. Use in Non−Epoxy Printed Wiring Boards, IPC APEX EXPO 2012, San Diego, California, USA., 28 February − 1 March, 2012; Curran Associates, Inc.;
[7] Leu, T. S.; Wang, C. S. J Appl Polym Sci 2004, 92, 410;
[8] Hwang, H.−J.; Li, C.−H.; Wang, C.−S. Polymer International 2006, 55,(11), 1341−1349;
[9] Hwang, H.−J.; Lin, C.−Y.; Wang, C.−S. Journal of Applied Polymer Science 2008, 110,(4), 2413−2423;
[10] Hwang, H.−J.; Li, C.−H.; Wang, C.−S. Journal of Applied Polymer Science 2005, 96,(6), 2079−2089;
[11] 台湾特開201723130。
Claims (13)
- 請求項1に記載の官能化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマーの製造方法であって、
(a)ルイス酸触媒の存在下、ジシクロペンタジエン(DCPD)及びフェノール類を80〜150℃に昇温し、攪拌しながら反応させ、合成した後に水で洗浄して中和して純化し、フェノール類の生成物を得る工程と、
(b)銅触媒/アミン類触媒の存在下、メタノール/水共溶媒において工程(a)で得られる前記フェノール類の生成物を2,6−ジメチルフェノールと混合し、酸素雰囲気において0〜70℃で酸化重合反応を行い、前記ポリフェニレンオキシドオリゴマーを得る工程と、
(c)アルカリ触媒の存在下、45〜100℃で工程(b)で得られる記ポリフェニレンオキシドオリゴマーを2−メタクリル酸無水物(無水メタクリル酸)或いはビニルベンジルハロゲン化合物と反応させ、前記末端基が官能化されたポリフェニレンオキシドオリゴマーを得る工程と、
(d)工程(c)で得られる前記末端基が官能化されたポリフェニレンオキシドオリゴマーを過酸化物或いはエポキシ樹脂と共重合して官能化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマーの硬化物を得る工程と、
を含む方法。 - 前記工程(a)において、DCPDとフェノール類のモル比は1/2〜1/10であり、前記工程(b)において、ビスフェノール単量体と2,6−ジメチルフェノールのモル比は1/2〜1/10である請求項2に記載の方法。
- 前記工程(a)において、前記フェノール類生成物はフェノール、2,6−ジメチルフェノール或いは2,3,6−トリメチルフェノールであり、前記ルイス酸触媒はBF3或いはハロゲン化アルミニウムであり、また、前記ハロゲン化アルミニウムは、トリクロロアルミニウム、トリブロモアルミニウム、エチルジクロロアルミニウム或いはジエチルクロロアルミニウムである請求項2に記載の方法。
- 前記工程(a)において、前記フェノール類の生成物は2,6−ジメチルフェノールであり、純化を行う際に、未反応物である2,6−ジメチルフェノールをビスフェノール単量体の製品において過量に存在させ、そして前記工程(b)において、2,6−ジメチルフェノールを別に添加せず、前記銅触媒/前記アミン類触媒の存在下、そのままで前記メタノール/水共溶媒と混合し、酸素雰囲気において、特定な温度で酸化重合反応を行う請求項2に記載の方法。
- 前記工程(a)において、前記フェノール類の生成物は2,6−ジメチルフェノールであり、未反応物である2,6−ジメチルフェノールをビスフェノール単量体の製品において過量に存在させ、そして前記工程(b)において、適量の2,6−ジメチルフェノールを更に添加し、前記銅触媒/前記アミン類触媒の存在下、前記メタノール/水共溶媒と混合し、酸素雰囲気において、特定な温度で酸化重合反応を行う請求項2に記載の方法。
- 前記工程(b)において、前記メタノール/水共溶媒における水の含有量は0体積%〜30体積%である請求項2に記載の方法。
- 前記工程(b)において、前記メタノール/水共溶媒における水の含有量は0.5体積%〜20体積%である請求項2に記載の方法。
- 前記工程(b)において、前記銅触媒は、CuCl、CuCl2、CuBr及びCuBr2からなる群から選ばれる少なくとも一つであり、前記アミン類触媒は第三級アミン(C2H5)3N或いはジアルキルアミノピリジンであり、アルキル基は炭素数1〜6のアルキル基である請求項2に記載の方法。
- 前記工程(b)において、前記酸素雰囲気の圧力範囲は14〜150psiであり、前記酸素雰囲気の酸素は空気或いは純酸素から由来する請求項2に記載の方法。
- 工程(c)において、前記アルカリ触媒は、炭酸カリウム(K2CO3)、炭酸ナトリウム(Na2CO3)、水酸化カリウム(KOH)、水素酸化ナトリウム(NaOH)、炭酸水素ナトリウム(NaHCO3)、酢酸ナトリウム、4−ジメチルアミノピリジン、ピリジン及び上記化合物の混合物からなる群から選ばれる少なくとも一つである請求項2に記載の方法。
- 前記工程(c)において、前記ビニルベンジルハロゲン化合物は、オルトビニルベンジルクロリド、メタビニルベンジルクロリド、パラビニルベンジルクロリド、オルトビニルベンジルブロマイド、メタビニルベンジルブロマイド、パラビニルベンジルブロマイド及び上記化合物の混合物からなる群から選ばれる少なくとも一つである請求項2に記載の方法。
- 請求項1に記載の官能化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマーを含み、高周波基板、耐高温添加剤、塗装材及び粘着剤からなる群から選ばれる少なくとも一つである製品。
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KR20220090451A (ko) * | 2020-12-22 | 2022-06-29 | 광둥 히노-테크 컴퍼니 리미티드 | 변성 알릴 화합물, 변성 비스말레이미드 프리폴리머 및 이의 용도 |
WO2022163360A1 (ja) | 2021-01-27 | 2022-08-04 | 三菱瓦斯化学株式会社 | (メタ)アクリル酸エステル化合物の製造方法 |
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EP3885391A1 (en) * | 2020-03-23 | 2021-09-29 | SHPP Global Technologies B.V. | Multifunctional poly(arylene ether) resins, method of making and articles obtained therefrom |
CN112624907B (zh) * | 2020-12-04 | 2022-11-29 | 上海彤程电子材料有限公司 | 一种芳烷基酚树脂的合成方法及其应用 |
CN115745931B (zh) * | 2021-09-03 | 2024-05-24 | 财团法人工业技术研究院 | 酸酐化合物、由其制得的聚酰亚胺与薄膜 |
KR20230082141A (ko) | 2021-12-01 | 2023-06-08 | 한국전자기술연구원 | 저유전성 그라프트 공중합체, 이를 포함하는 저유전성 필름 및 연성회로기판 |
WO2024106209A1 (ja) * | 2022-11-15 | 2024-05-23 | 日鉄ケミカル&マテリアル株式会社 | 多官能ビニル樹脂、その製造方法、多官能ビニル樹脂組成物及びその硬化物 |
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KR20220090451A (ko) * | 2020-12-22 | 2022-06-29 | 광둥 히노-테크 컴퍼니 리미티드 | 변성 알릴 화합물, 변성 비스말레이미드 프리폴리머 및 이의 용도 |
JP2022099289A (ja) * | 2020-12-22 | 2022-07-04 | グァンドン ヒンノ-テック カンパニー リミテッド | 変性アリル化合物、変性ビスマレイミドプレポリマー及びそれらの使用 |
JP7289902B2 (ja) | 2020-12-22 | 2023-06-12 | グァンドン ヒンノ-テック カンパニー リミテッド | 変性アリル化合物、変性ビスマレイミドプレポリマー及びそれらの使用 |
KR102674061B1 (ko) | 2020-12-22 | 2024-06-12 | 광둥 히노-테크 컴퍼니 리미티드 | 변성 알릴 화합물, 변성 비스말레이미드 프리폴리머 및 이의 용도 |
WO2022163360A1 (ja) | 2021-01-27 | 2022-08-04 | 三菱瓦斯化学株式会社 | (メタ)アクリル酸エステル化合物の製造方法 |
KR20230133876A (ko) | 2021-01-27 | 2023-09-19 | 미츠비시 가스 가가쿠 가부시키가이샤 | (메트)아크릴산에스테르 화합물의 제조 방법 |
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