JPS6050823B2 - ジヒドロキシ末端ポリパ−フルオロアルキレンオキサイドの製造方法 - Google Patents

ジヒドロキシ末端ポリパ−フルオロアルキレンオキサイドの製造方法

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Publication number
JPS6050823B2
JPS6050823B2 JP59067335A JP6733584A JPS6050823B2 JP S6050823 B2 JPS6050823 B2 JP S6050823B2 JP 59067335 A JP59067335 A JP 59067335A JP 6733584 A JP6733584 A JP 6733584A JP S6050823 B2 JPS6050823 B2 JP S6050823B2
Authority
JP
Japan
Prior art keywords
terminated
oxide
polyperfluoroalkylene
dihydroxy
formula
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
Application number
JP59067335A
Other languages
English (en)
Other versions
JPS59191725A (ja
Inventor
ロナルド・アレン・ミツチユ
ジヨゼフ・ラマ−ル・ゾ−リンガ−
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.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
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
Priority claimed from US00070540A external-priority patent/US3810874A/en
Priority claimed from CA120,659A external-priority patent/CA960400A/en
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of JPS59191725A publication Critical patent/JPS59191725A/ja
Publication of JPS6050823B2 publication Critical patent/JPS6050823B2/ja
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/175—Pantographs, i.e. printing devices
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/18—Electric or magnetic purposes in connection with recordings on magnetic tape or disc
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/185—Magnetic fluids

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polyethers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)
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Description

【発明の詳細な説明】 本発明はジヒドロキシ末端ポリパーフルオロアルキレン
オキサイドに関する。
航空工業において、密閉剤、ガスケット、０ーリング、
固体発射薬結合剤、等は低温度可撓性、高温度安定性、
耐溶媒性、および熱および酸化安定性を持たなければな
らない。
若干の上記性質を示す最近の先行技術の物質が述べられ
ているけれフども、今まで、上記要求事項を満足させか
つさらに望ましい低温度可撓性を有する重合体は提供さ
れていない。本発明は、極めて低いガラス転移温度を有
しかつ低温度において可撓性であり、そして耐溶媒性お
よび良好な加水分解、熱および酸化安定性を有する新規
な重合体の製造のため極めて有用である新規なジヒドロ
キシ末端ポリパーフルオロアルキレンオキサイドを提供
する。
本発明によるジヒドロキシ末端ポリパーフルオロアルキ
レンオキサイドは式（式中ｍおよびｎは各々、不規則に
分布されたパーフルオロエチレンオキシおよびパーフル
オロメチレンオキシ背骨反復副単位の数を示し、しかも
比率ｍ／ｎは０．２ハないし５ハ、好ましくは０．５１
１ないし２ハである）の背骨を有するエステルー末端ポ
リパーフルオロアルキレンオキサイドを還元するか、ま
たはこれらエステルーまたはアシルハライド末端化合物
をアミノアルコールと反応させることにより得ることが
できる。
本発明によるジヒドロキシ末端ポリ（パーフルオロアル
キレンオキサイド）は、５００ないし２００００または
より高い、好ましくは８００ないし１５０００の範囲の
数平均分子量Ｍ。
を有し、ポリアクリレート、ポリエステル、ポリシロキ
サン、ポリアミド等のような熱安定性、耐溶媒性重合体
の製造のためホモ重合または共重合される。上記のジヒ
ドロキシ末端化合物のガラス転移温度（Ｔｇ）は一般に
−７８゜Ｃより低く、好ましくは−１００゜Ｃより低く
、そして−１２５℃も低くまたはさらに低く、例．えば
−１３０′Ｃでありうる。これらの有利に低いガラス転
移温度はまたこの化合物から造られた重合体の特性であ
り、そして化合物中の酸素／弗素含有率を増加させるこ
とによりまたはポリ（パーフルオロアルキレンオキサ！
イド）セグメントの長さを増加させることによりさらに
下げることができる。
セグメントー末端基は通常かつ好ましくは一ＣＦ２−で
あるけれども、−Ｃ２Ｆ４−、−Ｃ３Ｆ６−または類似
のパーフルオロアルキレン基を含有する・セグメントを
つくることができ、それは−ＣＦ２−末端セグメントと
同一の性質を本質的に有する。
ポリ（パーフルオロアルキレンオキサイド）の背骨は、
パーフルオロメチレン基を末端とし、この末端基は非芳
香族二重結合を含まない二価基によりパーフルオロメチ
レン基に結合された重合反応性基を有する。本発明の線
状ヒドロキシー末端ポリ（パーフルオロアルキレンオキ
サイド）はそれ自身新規な材料であり、またそれらは−
７８℃より低い例外的に低いガラス転移点を有す。
それらは、例えば、それらの公知のエステルー、カルボ
キシー、またはアシルハライドー末端プレカーサーの環
元によノリ、または上記エステルーまたはアシルハライ
ドー末端プレカーサーとアミノアルコールとの反応（例
えばイタリヤ特許第８１７８的参照）により製造するこ
とができる。ヒドロキシー末端プレポリマーは普通ヒド
ロキシ官能性２を有す。このような．官能性は、プレポ
リマーを通常化学量論量以下で２，３−エポキシー１−
プロパノールのようなヒドロキシー含有エポキサイドと
反応させることにより例えば３まて増加させることがで
きる。たとえば−ＣＯＯＣＨ３末端先駆化合物をＬｉＡ
ｌＨ４で還元“することによソーＣＨ２ＣＨ末端ポリパ
ーフルオロアルキレンオキサイドを生成し、次いでＣＨ
２−ＣＨＣＨ２ＯＨと反応させると、一ゝ＼，．／（０
Ｈ）ＣＨ２ＯＨ末端化合物が得られる。
アミノアルコールの例としてはエタノールアミンまたは
プロパノールアミンがあり、この場合にはそれぞれ−０
ＣＨＮＣＨ２ＣＨ２０Ｈ末端および−ＣＯＮ（ＣＨ３）
ＣＨ２ＣＨ２ＯＨ末端生成物が得られる。本発明のヒド
ロキシ末端（パーフルオロアルキレンオキサイド）の数
平均分子量ＭＯは５００ないし１００００、好ましくは
８００ないし５０００の範囲てある。
これらのプレポリマーのガラス転移温度Ｔｇは一７８℃
より低く、好ましくは−９０゜Ｃより低く、更に−１２
５りＣ程度であることができ、プレポリマー中の酸素対
フッ素が高ければ高い程ガラス転移点は低い。（重合体
の“ガラス転移温度゛はそれ以上では重合体が軟かくゴ
ム状、即ち柔軟であり、それ以下では固いもろいガラス
である温度である；このような温度は一般に示差熱分析
、ＤＴＡまたは膨張係数の変化により測定される）。こ
のプレポリマーは一般に室温で透明で無色の液体であり
、低い容積粘度（例えば２ｒＣで１２５センチポイズ）
を有し、その性質はこれらの材料を用いるのに有利てあ
る。一般に、ヒドロキシー末端プレポリマーは異つた骨
格または鎖長を有する化合物の混合物である。実施例１ ヒドロキシ末端ポリ（パーフルオロアルキレンオキサイ
ド）の製造粉末のリチウムアルミニウムハイドライド（
１．９ｇ．．０．０５モル）を、機械的攪拌機、硫酸カ
ルシウム乾燥用管を具備する還流コンデンサー、および
ガス注入管の設けられている５００ｍ１の三ツ首フラス
コ中の乾燥ジエチルエーテル１２０ｍ１に添加し、混合
物を乾燥窒素下で４時間攪拌した。
式ＣＦ２ＣＯ２ＣＨ３で示されるメチルジエステル（Ｍ
ｎ＝１８００およびｍ／ｎ＝１．４ハ）のエーテル溶液
５０７７！１を、緩慢な還流を維持するに十分な速度で
リチウムアルミニウムハイドライドの攪拌溶液に添加し
た。すべてのエステルを添加した後、得られた混合物を
一夜にわたり加熱還流した。無水メチルアルコール（２
０ｍＬ）を添加して過剰のハイドライドを分解し、つい
て稀硫酸（水１００ｍ１中の３６ＮＨ２Ｓ０４３７ｇ）
を添加した。水性相および有機相を分離し、水性相をジ
エチルエーテルで４回抽出し、得られたエーテル部分と
有機相とを混合し、硫酸カルシウム上で乾燥した。硫酸
カルシウムとエーテルとを混合エーテル部分から除去し
て透明白色液体のメチロールー末端ポリ（パーフルオロ
アルキレンオキサイド）、を得た。
この生成物は約１８００（７）Ｍ。、９７５±５０のヒ
ドロキシ当量および−１０７℃のＴｇを有することが判
明した。実施例２ 各末端基上に一個より多いヒドロキシル基を含有する他
のタイプのヒドロキシー末端ポリ（パーフルオロアルキ
レンオキサイド）の製造５００ｍ１の丸底ガラスフラス
コに、実施例１で得られたメチロール末端ポリ（パーフ
ルオロアルキレンオキサイド）化合物（狂＝２０００，
．ｍ／ｎ＝０．６）１０５ｇを仕込んだ。
この系を脱気し、Ｎ２で覆い、次に、メタノール中のＮ
ａＯＣＨ３（４．８５ｒ］１ｅｑ／ｇ）溶液５．２５ｍ
１を磁気的に攪拌しながら注射器を通じて添力叱た。こ
の混合物を６５℃に加熱しながら、減圧下でメタノール
を除去した。この系を再びＮ２で覆い、４５℃に冷却し
、次いでグリシドール１．８５ｇを添加した。この混合
物を１１ｈ時間９０℃で攪拌した後、これを冷却し、Ｃ
Ｆ２ＣｌＣＦＣｌ２ｌ５Ｏｍｌで稀釈し、次いで１０％
水性Ｈ２ＳＯ４ｌＯｍｔで洗浄した。この溶液を乾燥し
、ろ過し、次いで濃縮した。０．８Ｔｆ＄ＬＨｇで９５
゜Ｃに最終的に加熱した後、生成物を焼結ガラスろう斗
を通じてろ過して微量の汚染物を除去した。
式 を有する化合物の未反応原料ジオール中の５０％溶液で
ある黄色透明生成物（９８．５ｇ１９２．５％）を得た
。
上記１：０．５の代りに、グリシドール対ジオ−ルのモ
ル比を２：１にすることにより、完全に二置換された生
成物も得た。この生成物それ自体は、ウレタンまたはポ
リエステル重合体のための交サ結合剤として有用である
。実施例３ エチロール置換アミド末端ポリ（パーフルオロアルキレ
ンオキサイド）の製造式 〜ノ五２〜ノＶ２υ工１３ ノで示されるメチルジエステル化合物（ＭＯ＝１４００
およびｍ／ｎ＝１．５５）１０．２ｇにエタノール０．
９ｇを徐々に添加し、攪拌する。
この混合物を１時間攪拌した後、赤外線スペクトルは、
ジエステル化合物が、エチロール置換アミド末端プレポ
リマーに７完全に変換されたことを示した。反応混合物
をジエチルエーテル１２５ｍ１中に溶解し、各回１０ｍ
１の水で３回洗浄し、硫酸カルシウム上で乾燥した。硫
酸カルシウムおよびエーテルを除去すると赤外線スペク
トルにより確認される構造を有する淡黄色プレポリマー
９．５ｇが得られた。

Claims (1)

  1. 【特許請求の範囲】 １ 式 Ａ−ＣＦ＿２Ｏ（ＣＦ＿２ＣＦ＿２Ｏ）＿ｍ（ＣＦ＿２
    Ｏ）＿ｎＣＦ＿２−Ａ′（式中ＡおよびＡ′は−ＣＯＯ
    Ｒ（Ｒは低級アルキル基である。 ）であり、ｍおよびｎは各々、不規則に分布されたパー
    フルオロエチレンオキシおよびパーフルオロメチレンオ
    キシ背骨反復副単位の数を示し、しかも比率ｍ／ｎは０
    ．２／１〜５／１である。）を有するエステル−末端ポ
    リパーフルオロアルキレンオキサイドを還元することを
    特徴とする、式−ＣＦ＿２Ｏ（ＣＦ＿２ＣＦ＿２Ｏ）＿
    ｍ（ＣＦ＿２Ｏ）＿ｎＣＦ＿２−（式中ｍおよびｎは上
    記のとおりである。 ）の背骨を有するジヒドロキシ−末端ポリパーフルオロ
    アルキレンオキサイドの製造法。２ 式 Ａ−ＣＦ＿２Ｏ（ＣＦ＿２ＣＦ＿２Ｏ）＿ｍ（ＣＦ＿２
    Ｏ）＿ｎＣＦ＿２−Ａ′（式中ＡおよびＡ′は−ＣＯＯ
    Ｒ（Ｒは低級アルキル基である。 ）また−ＣＯＸ（Ｘはハロゲンである。）であり、ｍお
    よびｎは各々、不規則に分布されたパーフルオロエチレ
    ンオキシおよびパーフルオロメチレンオキシ背骨反復副
    単位の数を示し、しかも比率ｍ／ｎは０．２／１〜５／
    １である。）を有するエステル−またはアシルハライド
    末端ポリパーフルオロアルキレンオキサイドをアミノア
    ルコールと反応させることを特徴とする、式 −ＣＦ＿２Ｏ（ＣＦ＿２ＣＦ＿２Ｏ）＿ｍ（ＣＦ＿２Ｏ
    ）＿ｎＣＦ＿２−（式中ｍおよびｎは上記のとおりであ
    る。 ）の背骨を有するジヒドロキシ−末端ポリパーフルオロ
    アルキレンオキサイドの製造法。
JP59067335A 1970-09-08 1984-04-04 ジヒドロキシ末端ポリパ−フルオロアルキレンオキサイドの製造方法 Expired JPS6050823B2 (ja)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US70540 1970-09-08
US00070540A US3810874A (en) 1969-03-10 1970-09-08 Polymers prepared from poly(perfluoro-alkylene oxide) compounds
US00108623A US3845051A (en) 1970-09-08 1971-01-21 Alpha,omega-di-s-triazinyl perfluoropolyoxa-alkanes
CA120,658A CA960221A (en) 1970-09-08 1971-08-16 Dis-"alpha, omega-di-s-triazinyl perfluoropoly-oxaalkanes"
CA120,659A CA960400A (en) 1970-09-08 1971-08-16 Poly(perfluoroalkylene oxide) derivatives
CA190,722A CA960222A (en) 1970-09-08 1974-01-21 Polyfunctional poly(perfluoroalkylene oxide) compounds

Publications (2)

Publication Number Publication Date
JPS59191725A JPS59191725A (ja) 1984-10-30
JPS6050823B2 true JPS6050823B2 (ja) 1985-11-11

Family

ID=27507950

Family Applications (5)

Application Number Title Priority Date Filing Date
JP59067334A Granted JPS59191724A (ja) 1970-09-08 1984-04-04 ビス−トリフルオロメタンスルホネ−ト化合物の製造方法
JP59067330A Granted JPS59191721A (ja) 1970-09-08 1984-04-04 ジアクリレ−ト化合物の製造方法
JP59067331A Granted JPS59191722A (ja) 1970-09-08 1984-04-04 ジエポキシド化合物の製造方法
JP59067335A Expired JPS6050823B2 (ja) 1970-09-08 1984-04-04 ジヒドロキシ末端ポリパ−フルオロアルキレンオキサイドの製造方法
JP59067333A Pending JPS59191723A (ja) 1970-09-08 1984-04-04 ビス−トリアルコキシシラン化合物の製造方法

Family Applications Before (3)

Application Number Title Priority Date Filing Date
JP59067334A Granted JPS59191724A (ja) 1970-09-08 1984-04-04 ビス−トリフルオロメタンスルホネ−ト化合物の製造方法
JP59067330A Granted JPS59191721A (ja) 1970-09-08 1984-04-04 ジアクリレ−ト化合物の製造方法
JP59067331A Granted JPS59191722A (ja) 1970-09-08 1984-04-04 ジエポキシド化合物の製造方法

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP59067333A Pending JPS59191723A (ja) 1970-09-08 1984-04-04 ビス−トリアルコキシシラン化合物の製造方法

Country Status (9)

Country Link
US (1) US3845051A (ja)
JP (5) JPS59191724A (ja)
AU (2) AU469118B2 (ja)
BE (2) BE772308A (ja)
CA (2) CA960221A (ja)
DE (2) DE2145174C3 (ja)
FR (2) FR2106375B1 (ja)
GB (2) GB1373932A (ja)
NL (2) NL7111865A (ja)

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FR2106375A1 (ja) 1972-05-05
JPS6214169B2 (ja) 1987-04-01
JPS59191722A (ja) 1984-10-30
AU3317671A (en) 1973-03-15
CA960221A (en) 1974-12-31
GB1373931A (en) 1974-11-13
BE772309A (fr) 1972-03-07
US3845051A (en) 1974-10-29
AU469118B2 (en) 1976-02-05
NL7111865A (ja) 1972-03-10
NL157596B (nl) 1978-08-15
JPS6214171B2 (ja) 1987-04-01
DE2145176A1 (de) 1972-03-16
AU462798B2 (en) 1975-07-10
DE2145174C3 (de) 1979-05-31
FR2116364B1 (ja) 1976-08-20
JPS59191724A (ja) 1984-10-30
JPS6214170B2 (ja) 1987-04-01
FR2106375B1 (ja) 1976-04-30
JPS59191723A (ja) 1984-10-30
AU3317471A (en) 1973-03-15
JPS59191725A (ja) 1984-10-30
NL7112315A (ja) 1972-03-10
JPS59191721A (ja) 1984-10-30
DE2145174B2 (de) 1978-10-05
GB1373932A (en) 1974-11-13
DE2145176C2 (de) 1983-05-26
DE2145174A1 (de) 1972-03-23
BE772308A (fr) 1972-03-07
CA960222A (en) 1974-12-31
FR2116364A1 (ja) 1972-07-13

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