JPH0415246B2 - - Google Patents

Info

Publication number
JPH0415246B2
JPH0415246B2 JP60017562A JP1756285A JPH0415246B2 JP H0415246 B2 JPH0415246 B2 JP H0415246B2 JP 60017562 A JP60017562 A JP 60017562A JP 1756285 A JP1756285 A JP 1756285A JP H0415246 B2 JPH0415246 B2 JP H0415246B2
Authority
JP
Japan
Prior art keywords
fluorine
structural unit
formula
mol
parts
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 - Lifetime
Application number
JP60017562A
Other languages
English (en)
Other versions
JPS61176620A (ja
Inventor
Akira Oomori
Hiroshi Inukai
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.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
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 Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to JP60017562A priority Critical patent/JPS61176620A/ja
Priority to US06/822,493 priority patent/US4667000A/en
Priority to DE8686101140T priority patent/DE3676512D1/de
Priority to EP86101140A priority patent/EP0190654B1/en
Publication of JPS61176620A publication Critical patent/JPS61176620A/ja
Publication of JPH0415246B2 publication Critical patent/JPH0415246B2/ja
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C08F214/00—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 a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/22—Vinylidene fluoride
    • C08F214/225—Vinylidene fluoride with non-fluorinated comonomers
    • C08F214/227—Vinylidene fluoride with non-fluorinated comonomers with non-fluorinated vinyl ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of 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 a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/12—Compositions of 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
    • C08L27/16—Homopolymers or copolymers or vinylidene fluoride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Description

【発明の詳細な説明】
〔産業上の利用分野〕 本発明は官能基を有する新規含フツ素共重合体
に関する。 〔従来の技術〕 従来、高温焼付が不要なフツ素樹脂常温硬化型
塗料には、硬化塗料成分の一つとしてフルオロオ
レフイン、シクロヘキシルビニルエーテル等を共
重合して得られる含フツ素共重合体が使用されて
いる（特開昭55−25414号公報、同57−34107号公
報および同57−34108号公報）。本発明者らは、ア
クリル樹脂をフツ素樹脂常温硬化型塗料に配合す
ると、耐候性、透光性、顔料分散性等が向上する
ことを見出した。しかしながら、上記従来の含フ
ツ素共重合体はアクリル樹脂と相溶性がよくなか
つた。 〔発明の目的〕 本発明の目的は、それ自身透光性がよく、しか
もアクリル樹脂との相溶性に優れた、官能基を有
する新規含フツ素共重合体を提供することであ
る。 〔発明の構成〕 本発明の要旨は、(1)構造単位： −CH2−CF2− (a)、 構造単位： （式中、ｎは１〜10の整数を示す。） および 構造単位： −CFX−CFY− (c) （式中、Ｘは水素、塩素またはフツ素、Ｙはフ
ツ素、低級フルオロアルキル基または
〔実施例〕
実施例 １ 300c.c.のステンレス製オートクレーブに酢酸エ
チル40ｇ、ヒドロキシブチルビニルエーテル
（HBVE）3.2ｇおよびジ−イソプロピルパーオキ
シ−ジ−カーボネート0.5ｇを仕込、脱気したの
ちビニリデンフルオライド（VdF）26ｇおよび
クロロトリフルオロエチレン（CTFE）10ｇを仕
込んだ。混合物を撹拌しながら40℃に15時間保ち
重合を行つた。得られた反応混合物を石油エーテ
ル中へあけ、生成した固体を減圧下40℃で50時間
乾燥した。重合体28ｇを得た。 重合体の前記条件で測定した〔η〕は0.20、示
差熱重量分析（DTGA）で求めた分解開始温度
は312℃、示差走査熱量計で求めた融点および結
晶化温度は、それぞれ75℃および13℃であつた。 得られた重合体は、3350cm-1にOH基に基づく
赤外吸収が、δ＝16ppmにHBVEに基づく核磁
気共鳴（NMR）シグナル（−OCH2CH2 ＣH2
CH2OH、下線部）が観察された。 得られた重合体を元素分析したところ、Ｃ：
34.6％、Ｈ：2.8％、Cl：8.2およびＦ：52.6％の
分析値が得られた。VdF／CTFE／HBVEの共
重合モル比は、78.3／17.4／4.3であつた。 更に、得られた共重合体をそれぞれ50重量部お
よび酢酸エチル50重量部からなる溶液にメチルメ
タクリレート／エチルメタクリレート／ヒドロキ
シエチルメタクリレートがモル比で80／10／10の
アクリル樹脂50重量部および酢酸エチル50重量部
からなる溶液を次表の割合で混合し、混合物100
部につき硬化剤としてヘキサメチレンヅイソシア
ネート３量体を13部加え充分混合したのち、スパ
ツタエツチング処理したテトラフルオロエチレ
ン／ヘキサフルオロプロピレン共重合体フイルム
上に塗布し、室温下３日間硬化させたのち溶媒を
完全に除去し、厚さ0.2mmの塗膜を得た。得られ
た塗膜について650nmにおける透光率を測定し
た。その結果を次の表に示す。
〔発明の効果〕
本発明の共重合体は、アクリル樹脂と相溶性が
よい。本発明の共重合体とアクリル樹脂からなる
組成物は、常温硬化型塗料にもちいることがで
き、これから得られる塗膜は、耐候性、透光性等
が優れたものである。

Claims (1)

  1. 【特許請求の範囲】 １ 構造単位： −CH2−CF2− (a)、 構造単位： （式中、ｎは１〜10の整数を示す。） および 構造単位： −CFX−CFY− (c) （式中、Ｘは水素、塩素またはフツ素、Ｙはフ
    ツ素、低級フルオロアルキル基または
    【式】基〔但し、ｍは０〜３ の整数〕を示す。） を有し、構造単位(a)，(b)および(c)をそれぞれ50〜
    99モル％、0.1〜30モル％および前記の残部（(a)，
    (b)および(c)の合計は100モル％）を含有し、数平
    均分子量が５千〜15万の含フツ素共重合体。
JP60017562A 1985-01-31 1985-01-31 含フッ素共重合体 Granted JPS61176620A (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP60017562A JPS61176620A (ja) 1985-01-31 1985-01-31 含フッ素共重合体
US06/822,493 US4667000A (en) 1985-01-31 1986-01-27 Fluorine-containing copolymer and composition containing the same
DE8686101140T DE3676512D1 (de) 1985-01-31 1986-01-29 Fluorhaltiges copolymer und zusammensetzung die das copolymer enthaelt.
EP86101140A EP0190654B1 (en) 1985-01-31 1986-01-29 Fluorine-containing copolymer and composition containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60017562A JPS61176620A (ja) 1985-01-31 1985-01-31 含フッ素共重合体

Publications (2)

Publication Number Publication Date
JPS61176620A JPS61176620A (ja) 1986-08-08
JPH0415246B2 true JPH0415246B2 (ja) 1992-03-17

Family

ID=11947351

Family Applications (1)

Application Number Title Priority Date Filing Date
JP60017562A Granted JPS61176620A (ja) 1985-01-31 1985-01-31 含フッ素共重合体

Country Status (4)

Country Link
US (1) US4667000A (ja)
EP (1) EP0190654B1 (ja)
JP (1) JPS61176620A (ja)
DE (1) DE3676512D1 (ja)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4851472A (en) * 1987-07-01 1989-07-25 Air Products And Chemicals, Inc. Copolymers of vinyl alcohol and fluorine-containing acrylate monomers
GB8716198D0 (en) * 1987-07-09 1987-08-12 Ici Plc Chemical process
JP2580650B2 (ja) * 1987-12-15 1997-02-12 ダイキン工業株式会社 乳化重合方法
JP2620295B2 (ja) * 1988-03-30 1997-06-11 関西ペイント株式会社 電着塗装用組成物
US5010153A (en) * 1988-06-03 1991-04-23 Air Products And Chemicals, Inc. Copolymers of vinyl acetate and fluorine-containing acrylate monomers
US5229461A (en) * 1990-05-22 1993-07-20 Daikin Industries, Ltd. Vinylidene fluoride copolymer and composition containing the same
JPH10147746A (ja) * 1996-11-20 1998-06-02 Daikin Ind Ltd 耐汚染性被膜形成組成物及び塗装品
KR100659955B1 (ko) * 1998-03-25 2006-12-22 다이낑 고오교 가부시키가이샤 불소함유 엘라스토머의 금속함유량 저감화 방법
EP2592108A1 (en) * 2006-12-20 2013-05-15 Honeywell International Inc. Copolymers for barriers
US20130089671A1 (en) * 2011-10-05 2013-04-11 Honeywell International Inc. Polymers formed from 2,3,3,3-tetrafluoropropene and articles and uses thereof
WO2014210249A1 (en) 2013-06-26 2014-12-31 3M Innovative Properties Company Stain resistant microsphere articles
FR3043084B1 (fr) * 2015-10-29 2017-10-27 Arkema France Copolymeres fluores fonctionnalises
US10570292B1 (en) 2018-10-09 2020-02-25 GM Global Technology Operations LLC Water-borne precursors for forming heterophasic anti-fouling, polymeric coatings having a fluorinated continuous phase with non-fluorinated domains
US11421114B2 (en) 2020-01-29 2022-08-23 GM Global Technology Operations LLC Precursors for forming heterophasic anti-fouling polymeric coatings

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3449305A (en) * 1966-03-01 1969-06-10 Du Pont Interpolymers of vinylidene fluoride
JPS5525414A (en) 1978-08-11 1980-02-23 Asahi Glass Co Ltd Fluorine-containing copolymer composition
JPS6021686B2 (ja) * 1980-08-08 1985-05-29 旭硝子株式会社 常温硬化可能な含フツ素共重合体
JPS5734108A (en) 1980-08-08 1982-02-24 Asahi Glass Co Ltd Fluorine-containing copolymer and curable composition containing same
JPS594473A (ja) * 1982-06-28 1984-01-11 Asahi Glass Co Ltd セメント系基材の塗装仕上げ方法
CA1230446A (en) * 1983-04-11 1987-12-15 Akira Ohmori Fluorine-containing copolymer and composition containing the same
JPS59189108A (ja) * 1983-04-11 1984-10-26 Daikin Ind Ltd 硬化性樹脂組成物

Also Published As

Publication number Publication date
DE3676512D1 (de) 1991-02-07
EP0190654A2 (en) 1986-08-13
JPS61176620A (ja) 1986-08-08
EP0190654B1 (en) 1990-12-27
EP0190654A3 (en) 1987-06-16
US4667000A (en) 1987-05-19

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