JPH02304093A - Acryl-modified fluorosilicone compound - Google Patents
Acryl-modified fluorosilicone compoundInfo
- Publication number
- JPH02304093A JPH02304093A JP12132989A JP12132989A JPH02304093A JP H02304093 A JPH02304093 A JP H02304093A JP 12132989 A JP12132989 A JP 12132989A JP 12132989 A JP12132989 A JP 12132989A JP H02304093 A JPH02304093 A JP H02304093A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- poly
- reaction
- acryl
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 abstract description 9
- 239000011737 fluorine Substances 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 abstract description 5
- -1 3-methacryloxypropyl Chemical group 0.000 abstract description 4
- 238000007033 dehydrochlorination reaction Methods 0.000 abstract description 3
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- OKQXCDUCLYWRHA-UHFFFAOYSA-N 3-[chloro(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)Cl OKQXCDUCLYWRHA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
［発明の目的］
（産業上の利用分野）
本発明は、合成樹脂の特性の改質に用いる有機ケイ素化
合物に関し、さらに詳しくはフッ素を有するアクリルモ
ノマーやフッ素を有するアクリルオリゴマーとの相溶性
が良好であり、これらのものと混合して共重合さゼ、そ
れらの特性の改質を行うことができる新規なアクリル変
性フルオロシリコーン化合物に関する。Detailed Description of the Invention [Objective of the Invention] (Industrial Field of Application) The present invention relates to organosilicon compounds used for modifying the properties of synthetic resins, and more specifically to fluorine-containing acrylic monomers and fluorine-containing acrylic monomers. This invention relates to a novel acrylic-modified fluorosilicone compound that has good compatibility with oligomers and can be mixed with these compounds to copolymerize and modify their properties.
（従来の技術）
従来より、アクリル変性シリコーンとしては、次式（Ｉ
Ｉ）に示す両末端に３−メタクリロギシブロビル基を有
するポリシメチルシロキザンが知られており、そのメタ
クリル基の重合反応性を利用して、ポリアクリル酸ニス
デル、ポリアクリロニトリル、ポリアクリルアミド、ポ
リスチレンなどの特性改質に使用されてきた。
□ＣＨ３ＣＨ３Ｃ；Ｈ３Ｃ１１３Ｃ１ｆ。(Prior art) Conventionally, acrylic modified silicone has the following formula (I
Polysimethylsiloxane having 3-methacrylogycibrobyl groups at both ends as shown in I) is known, and by utilizing the polymerization reactivity of the methacrylic group, polyacrylic acid Nisder, polyacrylonitrile, polyacrylamide, It has been used to modify the properties of polystyrene, etc.
□CH3CH3C; H3C113C1f.
０ ｃｎ３ＣＨ３ＣＨ，０（１１）（発明が解
決しようとする課題）
しかしながら、式（ＩＴ）の化合物はフッ素を有するア
クリルモノマーやフッ素を有するアクリルオリゴマーと
の相溶性が非常に悪く、これらのものと混合して共重合
反応を行うことがてぎないという欠点があった。0 cn3CH3CH,0(11) (Problem to be Solved by the Invention) However, the compound of formula (IT) has very poor compatibility with fluorine-containing acrylic monomers and fluorine-containing acrylic oligomers, and cannot be mixed with these. The drawback was that it was difficult to carry out the copolymerization reaction.
本発明の目的は、前記の欠点を解消した、フッ素を有す
るアクリルモノマーやフッ素を有するアクリルオリゴマ
ーとの相溶性が良好であり、これらと混合して共重合さ
せ、それらの特性改質を行うことができる、新規なアク
リル変性シリコーン化合物を提供することである。The object of the present invention is to solve the above-mentioned drawbacks, to have good compatibility with fluorine-containing acrylic monomers and fluorine-containing acrylic oligomers, and to improve their properties by mixing and copolymerizing them. An object of the present invention is to provide a novel acrylic-modified silicone compound that can perform the following steps.
（課題を解決するだめの手段）
本発明は、
一般式
％式％
（式中、Ｒは水素原子又はメチル基を表し、ｎは１〜］
０００の整数を表す）で示されるアクリル変性フルオロ
シリコーン化合物である。(Means for Solving the Problems) The present invention is based on the general formula % (wherein R represents a hydrogen atom or a methyl group, and n is 1 to 1)
(representing an integer of 000) is an acrylic-modified fluorosilicone compound.
本発明の化合物（Ｉ）において、ｎは１〜１０００であ
るが、好ましくは１〜３０の整数である。ｎが１０００
を越えると、粘度が大となり過ぎて取り扱いが困難であ
るばかりか、分子量を制御して製造することが困難とな
る。In compound (I) of the present invention, n is an integer of 1 to 1000, preferably 1 to 30. n is 1000
If it exceeds the viscosity, the viscosity becomes too high, making it difficult to handle, and also making it difficult to manufacture while controlling the molecular weight.
本発明の化合物（Ｉ）の製法の一例を以下に説明する。An example of the method for producing compound (I) of the present invention will be explained below.
本発明の化合物（Ｉ）は、α、υ−シヒドロギシーポリ
（３，３，３−トリフルオロプロピル）メチルシロキ
サン（Ｉｌｌ ）と３−（メタ）アクリロキシプロピル
ジメチルクロロシラン（ＩＶ）とを、第３級アミンなど
の塩化水素捕捉剤の存在下に脱塩化水素反応させること
により得られる。これを化学反応式で示すと、次式（１
）のようになる。Compound (I) of the present invention comprises α,υ-cyhydroxypoly(3,3,3-trifluoropropyl)methylsiloxane (Ill) and 3-(meth)acryloxypropyldimethylchlorosilane (IV). , can be obtained by dehydrochlorination reaction in the presence of a hydrogen chloride scavenger such as a tertiary amine. This can be expressed as a chemical reaction formula by the following formula (1
)become that way.
ｙ・
（７Ｈ２
にＨ２（１；Ｈ３
ｌｏ−（Ｓｉ０１゜〜ｌ ＋ ２ ＣＨ２・Ｃ−ＧＯ−
（ＣＨ２） ３−８ｉＣ１＋ ２ Ｂ晶３
ＣＨ３
（ＩＩＩ ） （ＩＶ ）−（Ｉ＋
＋ ２ ＢＩＩＣ］、 （１）（式
中、Ｒ及びｎは前記と同じであり、Ｂは第３級アミンを
表す）
α、ω−ジヒドロキシーポリ（３，３，１トリフルオロ
プロピル）メチルシロキサン（ＩＩＩ ）は公知物質で
あり、例えば米国特許第３８５３８３２号に記載の方法
により、容易に製造することが可能である。y・(7H2 to H2(1; H3 lo-(Si01゜~l + 2 CH2・C-GO-
(CH2) 3-8iC1+ 2 B crystal 3
CH3 (III) (IV)-(I+
+ 2 BIIC], (1) (wherein R and n are the same as above, and B represents a tertiary amine) α,ω-dihydroxypoly(3,3,1 trifluoropropyl)methylsiloxane (III) is a known substance and can be easily produced, for example, by the method described in US Pat. No. 3,853,832.
３−（メタ）アクリロキシプロピルジメチルクロロシラ
ン（ＩＶ）も公知物質であり、例えばアリルメタクリレ
−１・とジオルガノクロロシランを白金化合物を触媒と
してヒドロシリル化反応させることで容易に製造できる
。中でも製造が容易であることから３−メタクリロキシ
プロピルジメチルクロロシランが原料化合物として好ま
しい。3-(meth)acryloxypropyldimethylchlorosilane (IV) is also a known substance, and can be easily produced, for example, by subjecting allyl methacrylate-1 and diorganochlorosilane to a hydrosilylation reaction using a platinum compound as a catalyst. Among them, 3-methacryloxypropyldimethylchlorosilane is preferred as a raw material compound because it is easy to manufacture.
反応式（１）の脱塩化水素反応は、完全に反応させるた
めに、α、ω−ジヒドロキシ−ポリ（３，３，３−１−
リフルオロプロピル）メチルシロキサン（ｌ＋［）に対
して化学量論量以上、より好ましくは化学量論量の１０
５〜１５０倍の３−（メタ）アクリロキシプロピルジメ
チルクロロシラン（ＩＶ）及び第３級アミンを用いて行
われる。反応式（１）の反応は無溶媒でも進行するが、
副生ずる第３級アミンの塩酸塩によって撹拌が困難にな
るため、好ましくは不活性炭化水素溶媒中で行われる。In the dehydrochlorination reaction of reaction formula (1), α,ω-dihydroxy-poly(3,3,3-1-
more than stoichiometric amount, more preferably 10 stoichiometric amount based on (l+[)
It is carried out using 5 to 150 times more 3-(meth)acryloxypropyldimethylchlorosilane (IV) and a tertiary amine. Although the reaction of reaction formula (1) proceeds without solvent,
Since the by-produced tertiary amine hydrochloride makes stirring difficult, it is preferably carried out in an inert hydrocarbon solvent.
不活性炭化水素溶媒として（Ｊ、ｎ−ヘギサン、ベンゼ
ン、トルエン、キシレンなどが挙げられるが、中でもト
ルエンが特に好ましい。不活性炭化水素溶媒の使用量は
特に限定されないが、３−（メタ）アクリロキシプロピ
ルジメチルクロロシラン（ＩＶ）の使用量の１００〜５
００重凰％が好ましい。また、塩化水素捕捉剤として使
用される第３級アミンとしては、トリエチルアミン、ト
リイソプロピルアミン、１〜リブチルアミン、ピリジン
などが挙げられるが、中でもピリジンが特に好ましい。Examples of the inert hydrocarbon solvent include (J, n-hegisane, benzene, toluene, xylene, etc., among which toluene is particularly preferred. The amount of the inert hydrocarbon solvent used is not particularly limited, but 3-(meth)acrylic 100 to 5 of the usage amount of roxypropyldimethylchlorosilane (IV)
00 weight percent is preferred. Further, examples of the tertiary amine used as a hydrogen chloride scavenger include triethylamine, triisopropylamine, 1-butylamine, and pyridine, among which pyridine is particularly preferred.
反応方法（Ｊ特に限定されないが、α、ω−ジヒドロギ
シーボリ（３，３，３−トリフルオロプロピル）メチル
シロキサン（ＩＩＩ ）及び第３級アミンを溶解した不
活性炭化水素溶液に、３−（メタ）アクリロキシプロピ
ルジメチルクロロシラン（ＩＶ）を滴下反応させる方法
が、反応制御上好ましい。反応温度ば０〜５０℃の範囲
が好ましく、反応時間は３〜１０時間が適当である。反
応終了後、第３級アミンの塩酸塩を請訓し、有機層を水
洗し、乾燥する。乾燥後、低沸点留分を減圧留去するこ
とにより、本発明の化合物（Ｉ）が得られる。Reaction method (J Although not particularly limited, 3- A method of dropping (meth)acryloxypropyldimethylchlorosilane (IV) is preferred in terms of reaction control.The reaction temperature is preferably in the range of 0 to 50°C, and the reaction time is suitably 3 to 10 hours.After the reaction is completed The organic layer is washed with water and dried. After drying, the low-boiling fraction is distilled off under reduced pressure to obtain the compound (I) of the present invention.
［発明の効果１
本発明の化合物はその分子構造中に３．３．３−トリフ
ルオロプロピル基を有するために、フッ素を有するアク
リルモノマーやフッ素を有するアクリルオリゴマーとの
相溶性が非常に良好であり、これらのものと混合して共
重合反応させることが可能である。こうして得られた共
重合体は、本発明の化合物によって、耐汚染性、酸素透
過性、離型性、耐熱性、耐候性などの特性がイ」与され
、コンタクトレンズ材料、耐熱性塗料材料、耐候性塗料
材料、シール材料などとして有用である。[Effect of the invention 1] Since the compound of the present invention has a 3.3.3-trifluoropropyl group in its molecular structure, it has very good compatibility with fluorine-containing acrylic monomers and fluorine-containing acrylic oligomers. It is possible to copolymerize by mixing with these substances. The thus obtained copolymer is endowed with properties such as stain resistance, oxygen permeability, mold releasability, heat resistance, and weather resistance by the compound of the present invention, and can be used as a contact lens material, a heat-resistant coating material, etc. It is useful as a weather-resistant paint material, seal material, etc.
［実施例］
以下において、実施例をあげ本発明をさらに詳しく説明
する。なｊ３、本発明の範囲は以下の実施例のみに限定
されるものではない。[Example] The present invention will be explained in more detail below by giving examples. Note that the scope of the present invention is not limited only to the following examples.
実施例〕
撹拌機、温度計、滴下漏斗及び還流冷却器を備えた内容
積１℃のフラスコに、ａ、ω−ジヒドロキシ−ポリ （
３，３，３−ｈリフルオロプロピル）メチルシロキザン
（ＯＩ４基当量３５０、即ち数平均分子量７００）１４
６．６ｇ （Ｓｉ −〇Ｈ基として０．４２モルを含む
）、ピリジン３６．５ｇ （０，４，６モル）及びトル
エン２００ｇを仕込み、撹拌を開始した。Example] A,ω-dihydroxy-poly(
3,3,3-hlifluoropropyl)methylsiloxane (OI4 group equivalent weight 350, i.e. number average molecular weight 700) 14
6.6 g (containing 0.42 mol as Si -〇H group), 36.5 g (0.4.6 mol) of pyridine, and 200 g of toluene were charged, and stirring was started.
これに、滴下漏斗より３−メタクリロキシプロピルジメ
チルクロロシラン］、０２．１．ｇ（０４６モル）を、
液温２０〜４０’Ｃ；となるように氷バスで適宜冷却し
ながら、２時間かりて滴下した。滴下終了後、２５℃で
５時間撹拌した。To this, add 3-methacryloxypropyldimethylchlorosilane], 02.1. g (046 mol),
The solution was added dropwise over a period of 2 hours while being appropriately cooled in an ice bath so that the liquid temperature was 20-40'C. After the dropwise addition was completed, the mixture was stirred at 25°C for 5 hours.
次に、ピリジン塩酸塩を吸引２濾過により分離し、炉液
を飽和食塩水２００献で２回水洗後、無水芒硝を入れて
乾燥した。−晩乾燥後、液温８０°Ｃ１減圧度０ 、５
Ｔｏｒｒの条件で低沸点留分を５時間かけて留去した
。その結果、蒸留残液として無色透明液状のα、ω−ビ
ス（３−メククリロキシブロビル）−ポリ （３，３，
３−１〜リフルオロプロピル）メチルシロキザン１９７
．２ｇを得た。Next, pyridine hydrochloride was separated by suction 2 filtration, and the filtrate solution was washed twice with 200 parts of saturated brine, and then dried with anhydrous sodium sulfate. -After overnight drying, liquid temperature 80°C1 degree of vacuum 0,5
The low boiling point fraction was distilled off over 5 hours under Torr conditions. As a result, a colorless transparent liquid α,ω-bis(3-meccryloxybrobyl)-poly(3,3,
3-1~lifluoropropyl)methylsiloxane 197
．． 2g was obtained.
これは原料であるα、ω−ジヒドロキシーポリ（３，３
，３−１リフルオロプロピル）メチルシロキザンに対し
て、８６８％の収率であった。This is the raw material α,ω-dihydroxypoly(3,3
The yield was 868% based on methylsiloxane.
このものの屈折率測定、赤外線吸収スペクトル分析、１
Ｈ核磁気共鳴吸収分析およびＧＰＣ分析の結果は後記の
通りであり、次式の分子構造であることを確認した。Measurement of refractive index of this material, analysis of infrared absorption spectrum, 1
The results of H nuclear magnetic resonance absorption analysis and GPC analysis are as shown below, and it was confirmed that the molecular structure was as shown below.
Ｆ３
ｂｃ ｄｅｆ ｇ ＣＨｚｉ
「
ＨＣＨ，ＣＨ２ＣＨ２ｈ ＣＨ３ＣＨ３ＩＣ＝Ｃ−ＧＯ
−ＣＨ３ＣＨ２ＣＨ７−３ｊＯ−［５ｉ０１ ｎ−３ｉ
−ｆｃＨ２１３−ＱＣ−（ニーＣＨ２Ｏ（：Ｈ，ＣＨ３
ＣＨ，Ｏ
ａ ｇ
・屈折率測定（ｎ２５ｏ１ ： １ 、４１４０・赤
外線吸収スペクトル分析（液膜法）波数（ｃｍ−’）
帰属
２９５０ Ｃ−Ｈ
１７２０Ｇ＝０
１６４０ Ｃ＝Ｃ
９−７ｒノ
１２６０ ５ｉ−ＣＨ３１０６０５ｉ
−０−５ｉ
・’ Ｈ核磁気共鳴吸収分析（９０ＭＨｚ、 ＣＤＣｌ
３中）位置 化学シフト（δｐｐｍ１積分強度 多重度
ａ ６’、１． ２Ｈｂ
３．５ ２Ｈ
１，９６０
ｄ ４．１． ４Ｈｔ
ｅ １．５−１．７ ４Ｈ
ｆ ０．４〜０．７ ４０ｇ
０．１ ２４Ｈｓｈ
Ｏ，４〜０．７ ８Ｈ１１６〜２．２
８１１
・ＧＰＣ分析F3 bc def g CHzi " HCH, CH2CH2h CH3CH3IC=C-GO
-CH3CH2CH7-3jO-[5i01 n-3i
-fcH213-QC-(nee CH2O(:H,CH3
CH, O a g
・Refractive index measurement (n25o1: 1, 4140 ・Infrared absorption spectrum analysis (liquid film method) wave number (cm-')
Attribution 2950 C-H 1720G=0 1640 C=C 9-7rノ1260 5i-CH310605i
-0-5i ・'H nuclear magnetic resonance absorption analysis (90MHz, CDCl
3) Position Chemical shift (δppm1 integrated intensity Multiplicity a 6', 1.2Hb
3.5 2H 1,960 d 4.1. 4Ht
e 1.5-1.7 4H
f 0.4~0.7 40g
0.1 24Hsh
O, 4~0.7 8H116~2.2
811 ・GPC analysis
Claims (1)
０００の整数を表す）で示されるアクリル変性フルオロ
シリコーン化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R represents a hydrogen atom or a methyl group, and n is 1 to 1
An acrylic-modified fluorosilicone compound represented by an integer of 000).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12132989A JPH02304093A (en) | 1989-05-17 | 1989-05-17 | Acryl-modified fluorosilicone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12132989A JPH02304093A (en) | 1989-05-17 | 1989-05-17 | Acryl-modified fluorosilicone compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02304093A true JPH02304093A (en) | 1990-12-17 |
Family
ID=14808562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12132989A Pending JPH02304093A (en) | 1989-05-17 | 1989-05-17 | Acryl-modified fluorosilicone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02304093A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391677A (en) * | 1991-07-23 | 1995-02-21 | Shin-Etsu Chemical Co., Ltd. | Acrylic-functional organopolysiloxane and method for the preparation thereof |
| US5445867A (en) * | 1991-10-30 | 1995-08-29 | Shin-Etsu Chemical Co., Ltd. | Thermal transfer recording sheets and back coating compositions therefor |
| US7087694B2 (en) | 2000-11-15 | 2006-08-08 | E. I. Du Pont De Nemours And Company | Fluorinated copolymers for hydrophobic and oleophobic treatment of building materials |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4847998A (en) * | 1971-10-22 | 1973-07-07 |
-
1989
- 1989-05-17 JP JP12132989A patent/JPH02304093A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4847998A (en) * | 1971-10-22 | 1973-07-07 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391677A (en) * | 1991-07-23 | 1995-02-21 | Shin-Etsu Chemical Co., Ltd. | Acrylic-functional organopolysiloxane and method for the preparation thereof |
| US5445867A (en) * | 1991-10-30 | 1995-08-29 | Shin-Etsu Chemical Co., Ltd. | Thermal transfer recording sheets and back coating compositions therefor |
| US7087694B2 (en) | 2000-11-15 | 2006-08-08 | E. I. Du Pont De Nemours And Company | Fluorinated copolymers for hydrophobic and oleophobic treatment of building materials |
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