JPS6361336B2 - - Google Patents
Info
- Publication number
- JPS6361336B2 JPS6361336B2 JP61183277A JP18327786A JPS6361336B2 JP S6361336 B2 JPS6361336 B2 JP S6361336B2 JP 61183277 A JP61183277 A JP 61183277A JP 18327786 A JP18327786 A JP 18327786A JP S6361336 B2 JPS6361336 B2 JP S6361336B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- terminated
- oxide
- och
- compound
- 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
Links
- -1 perfluoroethyleneoxy Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical compound CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- AONDIGWFVXEZGD-UHFFFAOYSA-N diacetyloxy(methyl)silicon Chemical compound CC(=O)O[Si](C)OC(C)=O AONDIGWFVXEZGD-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- YOQUCILXQDXKQE-UHFFFAOYSA-N silyl 2-methylpropanoate Chemical compound CC(C)C(=O)O[SiH3] YOQUCILXQDXKQE-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Polyethers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
- Lubricants (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Description
【発明の詳細な説明】
本発明は反応性シラン末端ポリパーフルオロア
ルキレンオキサイドの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for making reactive silane terminated polyperfluoroalkylene oxides.
航空工業において、密閉剤、ガスケツト、Ｏ−
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
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。 In the aviation industry, sealants, gaskets, O-
rings, solid propellant binders, etc. are low temperature flexible,
It must have high temperature stability, solvent resistance, and thermal and oxidative stability. Although recent prior art materials have been described that exhibit some of the above properties, to date no polymers have been provided that satisfy the above requirements and also have the desirable low temperature flexibility.
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
新規な反応性シラン末端ポリ（パーフルオロアル
キレンオキサイド）を提供する。 The present invention is extremely useful for the production of new polymers that have extremely low glass transition temperatures, are flexible at low temperatures, and have solvent resistance and good hydrolytic, thermal and oxidative stability. Certain novel reactive silane terminated poly(perfluoroalkylene oxides) are provided.
本発明は、式
H2C＝CHCH2OCH2−CF2O（CF2CF2O）n（CF2O）oCF2−CH2O
CH2CH＝CH2
（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0.2／１ないし５／１である）
の背骨を有するアリル末端ポリパーフルオロアル
キレンオキシドを、アセトキシシランと反応させ
ることを特徴とする、式
（CH3CO2）3-zSi（CH3）z（CH2）3OCH2−CF2O（CF2CF2O
）n（CF2O）oCF2
−CH2O（CH2）3Si（CH3）z（O2CCH3）3-z
（式内ｍおよびＮは上記の通りであり、ｚは１ま
たは２である）
の背骨を有する反応性シラン末端パーフルオロア
ルキレンオキサイドの製造方法に関する。 The present invention uses the formula H2C = CHCH2OCH2 -CF2O ( CF2CF2O ) n ( CF2O ) o CF2 - CH2O
CH 2 CH=CH 2 , where m and n indicate the number of irregularly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone repeating subunits, respectively, and the ratio m/n is from 0.2/1 to 5. /1) characterized in that an allyl-terminated polyperfluoroalkylene oxide having a backbone of the formula (CH 3 CO 2 ) 3-z Si(CH 3 ) z (CH 2 ) 3 is reacted with acetoxysilane. OCH 2 −CF 2 O (CF 2 CF 2 O
) n (CF 2 O) o CF 2 −CH 2 O (CH 2 ) 3 Si (CH 3 ) z (O 2 CCH 3 ) 3-z (m and N in the formula are as above, and z is 1 or 2) A method for producing a reactive silane-terminated perfluoroalkylene oxide having a backbone of
式の化合物は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oを有する。式の化合物は、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できる。式（）の
化合物のガラス転移温度（Tg）は一般に−78℃
より低く、好ましくは−100℃より低く、そして
−125℃またはさらに低く、例えば−130℃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。 The compounds of formula have a number average molecular weight o ranging from 500 to 20,000 or higher, preferably from 800 to 15,000. Compounds of the formula can be homopolymerized or copolymerized to produce heat-stable, solvent-resistant polymers such as polyacrylates, polyesters, polysiloxanes, polyamides, and the like. The glass transition temperature (Tg) of the compound of formula () is generally -78℃
lower, preferably lower than -100<0>C, and may be -125<0>C or even lower, for example -130<0>C. These advantageously low glass transition temperatures are also a property of polymers made from this compound, and can be achieved by increasing the oxygen/fluorine content in the compound or by increasing the length of the poly(perfluoroalkylene oxide) segments. It can be further lowered by increasing it.
かくして式の反応性シラン末端ポリ（パーフ
ルオロアルキレンオキサイド）化合物は重合また
は共重合させることにより式
−CF2O（CF2CF2O）n（CF2O）oCF2−
（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、0.2／１ないし５／１、好ましく
は0.5／１ないし２／１である）
の反復背骨単位を含む重合体が形成される。代表
的に、この重合体は少なくとも1100、好ましくは
少なくとも5000、しばしば2000000またはより高
い分子量を有する。 Thus, a reactive silane-terminated poly(perfluoroalkylene oxide) compound of the formula can be polymerized or copolymerized to form a compound of the formula -CF 2 O(CF 2 CF 2 O) n (CF 2 O) o CF 2 − (where m and n each indicates the number of irregularly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone repeating subunits, and the ratio m/n is from 0.2/1 to 5/1, preferably from 0.5/1 to 2. A polymer containing repeating backbone units of /1) is formed. Typically, the polymer will have a molecular weight of at least 1100, preferably at least 5000, often 2,000,000 or higher.
原料物質である式のアリル末端ポリパーフル
オロアルキレンオキサイド化合物は相当するメチ
ロール（−CH2OH）末端先駆化合物からたとえ
ばCH2＝CHCH2Brとの反応により得られる。こ
の方法は、例えばターレー（Talley）等による
アリルブチルエーテルの製法に基いて実施される
（J.Am.Chem.Soc.第73巻 No.7.1951年７月６日発
行、3528頁参照）。ターレの方法は、アルコール
をアルコキサイドとしてアリルブロミドと反応さ
せることから成り、この反応は古典的なウイリア
ムソンのエーテル合成法である（“Organic
Functional Group Preparation”by Sandler＆
Karo、Academic Press、Ind.、N.Y.、N.Y.
（1968）101頁参照）。メチロール末端先駆化合物
はまたエステル（−COOCH3）末端化合物から、
たとえばLiAlH4を用いる還元により製造できる。 The starting material, an allyl-terminated polyperfluoroalkylene oxide compound of the formula, is obtained from the corresponding methylol ( -CH2OH )-terminated precursor compound by reaction with, for example, CH2 = CHCH2Br . This method is carried out, for example, based on the method for producing allyl butyl ether by Talley et al. (see J. Am. Chem. Soc. Vol. 73, No. 7, published July 6, 1951, p. 3528). Thale's method consists of reacting the alcohol as an alkoxide with allyl bromide, a reaction that is classic Williamson ether synthesis (“Organic
Functional Group Preparation”by Sandler＆
Karo, Academic Press, Ind., NY, NY
(1968) p. 101). Methylol-terminated precursor compounds are also derived from ester (-COOCH 3 )-terminated compounds.
For example, it can be produced by reduction using LiAlH 4 .
エステル末端先駆物質はイタリー特許明細書第
817809号中に、その製造方法と共に記載されてい
る。 Ester-terminated precursors are described in Italian patent specification no.
817809, along with its manufacturing method.
前記反応性−末端ポリ（パーフルオロアルキレ
ンオキサイド）は、重合体の製造用プレポリマー
としてのこれらの用途以外に、潤滑剤、過ハロゲ
ン化潤滑剤のための粘度指数添加剤、油圧用流
体、撥水および撥油剤、表面活性剤、腐食防止
剤、モールド用付着防止剤または離型剤、浮遊
剤、および弗素化プラスチツク用可塑剤としてま
た有用である。 Besides their use as prepolymers for the production of polymers, the reactive-terminated poly(perfluoroalkylene oxides) are used in lubricants, viscosity index additives for perhalogenated lubricants, hydraulic fluids, repellents. Also useful as water and oil repellents, surfactants, corrosion inhibitors, anti-stick or mold release agents, flotation agents, and plasticizers for fluorinated plastics.
次例により本発明をさらに説明する。 The invention is further illustrated by the following examples.
例 １
ガラスアンプル中に、前記式のアリル−末端
ポリ（パーフルオロアルキレンオキサイド）（o
＝2000、ｍ／ｎ＝0.6）25ｇ（22.4meq.）、ジメチ
ルアセトキシシラン4.4ｇ（18.4meq.）、メチルジ
アセトキシシラン0.65ｇ（4.0meq.）およびCCl4
中のＨ（PtCl3・C2H2）の３％溶液３滴を入れた。
この密閉管を65時間、80℃で加熱した。液体のシ
ラン−末端ポリ（パーフルオロアルキレンオキサ
イド）：
（CH3CO2）3-zSi（CH3）z（CH2）3OCH2−CF2−Ｏ−（CF
2CF2O）n（CF2O）o−CF2
−CH2O（CH2）3−Si（CH3）z（O2CCH3）3-z
（式中ｚ＝１および２）生成物を、テトライソプ
ロピルチタネートの触媒量と混合し、混合物を約
25℃で６日間、ついで100℃で１日間大気の湿気
に暴露させることにより、軟質弾性ゴムに硬化さ
せた。軟質ポリシロキサン硬化生成物82部を、細
かく粉砕したシリカ８部、細かく粉砕した酸化鉄
（Fe2O3）10部、および過酸化ベンゾイル１部と、
小さいゴムミルの補助により配合した。プレス中
で６時間、177℃において得られた物質を硬化さ
せ、次いで24時間、177℃において緩硬化させる
と、36のシヨア−Ａ−２硬度、176Kg／cm2の引つ
ぱり強さ、140％の破壊の際の伸び、1.93ｇ／c.c.
の密度、および−125ないし114℃のTgを有する
ポリエーテル−ポリシロキサンゴムが得られた。Example 1 In a glass ampoule, an allyl-terminated poly(perfluoroalkylene oxide) of the above formula ( o
=2000, m/n=0.6) 25g (22.4meq.), dimethylacetoxysilane 4.4g (18.4meq.), methyldiacetoxysilane 0.65g (4.0meq.) and CCl 4
Three drops of a 3% solution of H (PtCl 3 .C 2 H 2 ) in the solution were added.
The sealed tube was heated at 80° C. for 65 hours. Liquid silane-terminated poly(perfluoroalkylene oxide): ( CH3CO2 ) 3-zSi ( CH3 ) z ( CH2 ) 3OCH2 - CF2- O- (CF
2 CF 2 O) n (CF 2 O) o −CF 2 −CH 2 O(CH 2 ) 3 −Si(CH 3 ) z (O 2 CCH 3 ) 3-z (z=1 and 2 in the formula) generation is mixed with a catalytic amount of tetraisopropyl titanate and the mixture is
It was cured to a soft elastic rubber by exposure to atmospheric moisture for 6 days at 25°C and then 1 day at 100°C. 82 parts of a soft polysiloxane cured product were combined with 8 parts of finely ground silica, 10 parts of finely ground iron oxide (Fe 2 O 3 ), and 1 part of benzoyl peroxide;
Compounded with the aid of a small rubber mill. Curing the resulting material at 177°C for 6 hours in a press and then slowly curing at 177°C for 24 hours gave a Shore-A-2 hardness of 36, a tensile strength of 176 Kg/cm 2 , a tensile strength of 140 % elongation at break, 1.93g/cc
A polyether-polysiloxane rubber was obtained having a density of , and a Tg of -125 to 114°C.
例 ２（参考例）
反応器に、不活性溶媒中式
HOCH2−CF2O（CF2CF2O）n（CF2O）oCF2−
CH2OH
を有する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（平均分子量2000、ｍ／ｎ＝0.6）
60ｇ（0.03モル）を仕込み、ナトリウム1.4ｇ
（0.06モル）を徐々に加えた。混合物を還流温度
に加熱し、アリルブロミド12.1ｇ（0.1モル）を
徐々に加え、更に還流温度に加熱し、式のビス
アリルエーテル25ｇを得た。Example 2 (Reference example) In a reactor, in an inert solvent, the formula HOCH 2 −CF 2 O (CF 2 CF 2 O) n (CF 2 O) o CF 2 −
Hydroxy-terminated polyperfluoroalkylene oxide with CH 2 OH (average molecular weight 2000, m/n=0.6)
Prepared 60g (0.03mol), sodium 1.4g
(0.06 mol) was added gradually. The mixture was heated to reflux temperature, 12.1 g (0.1 mol) of allyl bromide was slowly added, and further heated to reflux temperature to obtain 25 g of bisallyl ether of formula.
Claims (1)
2OCH2CH＝CH2 （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0.2／１ないし５／１である） を有するアリル末端ポリパーフルオロアルキレン
オキシドを、アセトキシシランと反応させること
を特徴とする、式 （CH3CO2）3-zSi（CH3）z（CH2）3OCH2−CF2O（CF2CF2O
）n（CF2O）oCF2 −CH2O（CH2）3Si（CH3）z（O2CCH3）3-z （式中ｍおよびｎは上記のとおりであり、ｚは１
または２である） を有する反応性シラン末端パーフルオロアルキレ
ンオキサイドの製造方法。[Claims] 1 Formula H 2 C=CHCH 2 OCH 2 −CF 2 O (CF 2 CF 2 O) n (CF 2 O) o CF 2 −CH
2 OCH 2 CH=CH 2 where m and n indicate the number of irregularly distributed perfluoroethyleneoxy and perfluoromethyleneoxy backbone repeating subunits, respectively, and the ratio m/n is from 0.2/1 to 5/1) with the formula (CH 3 CO 2 ) 3-z Si(CH 3 ) z (CH 2 ) 3 OCH 2 −CF 2 O (CF 2 CF 2 O
) n (CF 2 O) o CF 2 −CH 2 O (CH 2 ) 3 Si (CH 3 ) z (O 2 CCH 3 ) 3-z (where m and n are as above, and z is 1
or 2) A method for producing a reactive silane-terminated perfluoroalkylene oxide.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00070540A US3810874A (en) | 1969-03-10 | 1970-09-08 | Polymers prepared from poly(perfluoro-alkylene oxide) compounds |
| US70540 | 1970-09-08 | ||
| 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 |
|---|---|
| JPS6248724A JPS6248724A (en) | 1987-03-03 |
| JPS6361336B2 true JPS6361336B2 (en) | 1988-11-29 |
Family
ID=27425500
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59067332A Pending JPS6034924A (en) | 1970-09-08 | 1984-04-04 | Manufacture of difunctional terminal polyperfluoroalkylene oxide |
| JP61183277A Granted JPS6248724A (en) | 1970-09-08 | 1986-08-04 | Production of reactive silane terminal polyperfluoroalkyleneoxide |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59067332A Pending JPS6034924A (en) | 1970-09-08 | 1984-04-04 | Manufacture of difunctional terminal polyperfluoroalkylene oxide |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS6034924A (en) |
| BR (1) | BR7105885D0 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005508433A (en) * | 2001-11-08 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Coating compositions comprising partial condensates of fluorochemical polyether silanes and their use |
| JP2005508420A (en) * | 2001-11-08 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Coating compositions containing fluorochemical polyether silane polycondensates and their use |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1218217B (en) * | 1988-04-13 | 1990-04-12 | Ausimont Spa | ANTIRUST ADDITIVES FOR LUBRICANTS OR GREASES BASED ON PERFLUOROPOLYETERS |
| JPH03240912A (en) * | 1990-02-19 | 1991-10-28 | Kawasaki Steel Corp | Method for operating oxygen bottom blown converter |
| WO1998049218A1 (en) * | 1997-04-30 | 1998-11-05 | Daikin Industries, Ltd. | Fluoropolymer, process for preparing the same, and use thereof |
| ITMI20011034A1 (en) * | 2001-05-18 | 2002-11-18 | Ausimont Spa | PROCESS FOR THE PREPARATION OF FLUOROPOLOSSOALKYLENS WITH A TERMINAL -CH 2OH AND THE OTHER TERMINAL CONTAINING CHLORINE |
| EP2170975B1 (en) * | 2007-07-10 | 2018-05-02 | Carnegie Mellon University | Compositions and methods for producing cellular labels for nuclear magnetic resonance techniques |
| KR101969187B1 (en) * | 2011-09-21 | 2019-04-15 | 에이지씨 가부시키가이샤 | Fluorine-containing ether composition, method for producing same, coating fluid, and method for manufacturing substrate having surface-treated layer |
| KR101671089B1 (en) * | 2012-06-13 | 2016-10-31 | 다이킨 고교 가부시키가이샤 | Silane compound containing perfluoropolyether group and surface-treating agent |
| JP6130288B2 (en) * | 2013-11-22 | 2017-05-17 | 信越化学工業株式会社 | Allyl group-modified fluorooxyalkylene group-containing polymer and production method thereof |
| WO2016084746A1 (en) * | 2014-11-28 | 2016-06-02 | ダイキン工業株式会社 | Modified fluorooxymethylene group-containing perfluoropolyether |
| EP3320021B1 (en) * | 2015-07-09 | 2019-05-15 | Solvay Specialty Polymers Italy S.p.A. | Process for the synthesis of (per)fluoropolyether amines |
| JP6950697B2 (en) * | 2016-08-30 | 2021-10-13 | Ａｇｃ株式会社 | Method for Producing Fluorine-Containing Ether Compound |
| US20200362136A1 (en) * | 2017-12-08 | 2020-11-19 | 3M Innovative Properties Company | Curable fluorinated polymer compositions |
-
1971
- 1971-09-06 BR BR5885/71A patent/BR7105885D0/en unknown
-
1984
- 1984-04-04 JP JP59067332A patent/JPS6034924A/en active Pending
-
1986
- 1986-08-04 JP JP61183277A patent/JPS6248724A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005508433A (en) * | 2001-11-08 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Coating compositions comprising partial condensates of fluorochemical polyether silanes and their use |
| JP2005508420A (en) * | 2001-11-08 | 2005-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | Coating compositions containing fluorochemical polyether silane polycondensates and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7105885D0 (en) | 1973-03-13 |
| JPS6034924A (en) | 1985-02-22 |
| JPS6248724A (en) | 1987-03-03 |
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