JPH0543885A - Lubricating function-imparting agent - Google Patents

Lubricating function-imparting agent

Info

Publication number
JPH0543885A
JPH0543885A JP3228900A JP22890091A JPH0543885A JP H0543885 A JPH0543885 A JP H0543885A JP 3228900 A JP3228900 A JP 3228900A JP 22890091 A JP22890091 A JP 22890091A JP H0543885 A JPH0543885 A JP H0543885A
Authority
JP
Japan
Prior art keywords
wax
lubricating function
imparting agent
imparting
hydrogen group
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.)
Granted
Application number
JP3228900A
Other languages
Japanese (ja)
Other versions
JP3078613B2 (en
Inventor
Ryoichi Kitamura
良一 北村
Taizo Yasumoto
泰三 安本
Shuzo Ohara
柊三 大原
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.)
Goyo Paper Working Co Ltd
Original Assignee
Goyo Paper Working Co 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
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Application filed by Goyo Paper Working Co Ltd filed Critical Goyo Paper Working Co Ltd
Priority to JP22890091A priority Critical patent/JP3078613B2/en
Priority to EP92102196A priority patent/EP0527286A1/en
Publication of JPH0543885A publication Critical patent/JPH0543885A/en
Application granted granted Critical
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  • Lubricants (AREA)

Abstract

PURPOSE:To obtain the title agent which has an excellent effect of imparting a lubricating function and is highly compatible with a wax. CONSTITUTION:The title agent is prepared by reacting an organosilicon compound having at least one hydrogen group with a 18C or higher hydrocarbon compound having at least one double bond reactive with the hydrogen group. An example of the agent is one prepared by effecting an addition reaction of an 18C or higher alpha-olefin with polymethylhydrogensiloxane and/or methylhydrogensiloxane/dimethylsiloxane copolymer.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、潤滑機能付与剤に関
し、更に詳しくは、優れた潤滑機能付与効果及びその良
好な持続性を有する潤滑機能付与剤に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a lubricating function imparting agent, and more particularly to a lubricating function imparting agent having an excellent lubricating function imparting effect and good durability thereof.

【0002】[0002]

【従来の技術】従来、この種の潤滑機能付与を目的とす
るものとしては、ワックス系のものと、シリコーン系の
ものが知られている。
2. Description of the Related Art Hitherto, wax-based and silicone-based materials have been known for the purpose of imparting this type of lubricating function.

【0003】ワックス系のものは潤滑機能も付与するも
のの、艶出し効果の方が大きい。また通常のシリコーン
系については、艶出し効果もあり、潤滑機能付与効果も
あるが、ワックスとの相溶性がなく、またワックス変性
したカルナウバ変性シリコーンは潤滑機能付与効果は低
下し、艶出し効果が出てくる。
The wax-based ones have a lubricating effect, but have a greater glossing effect. In addition, ordinary silicones have a glossing effect and also have a lubricating function imparting effect, but they are not compatible with wax, and wax-modified carnauba-modified silicone reduces the lubricating function imparting effect and has a glossing effect. Come out.

【0004】以上のように、これまでの潤滑機能付与剤
は、その潤滑付与効果、その持続性、並びに取り扱い性
及び使用形態の面で必ずしも満足し得るものとは言い難
いのが実情である。
As described above, it is difficult to say that the conventional lubrication function-imparting agents are necessarily satisfactory in terms of their lubrication-imparting effect, their durability, handleability and usage form.

【0005】[0005]

【発明が解決しようとする課題】本発明は、上記実情に
鑑み、潤滑付与効果、その持続性、並びに取り扱い性及
び使用形態において充分に満足し得る潤滑機能付与剤を
提供するものである。
In view of the above circumstances, the present invention provides a lubricant function-imparting agent which is sufficiently satisfactory in lubrication effect, its durability, handleability and use form.

【0006】[0006]

【課題を解決するための手段】即ち、本発明は少なくと
も1個の水素基を有する有機珪素化合物と、該水素基と
反応する二重結合を少なくとも1個有する炭素数18以
上の炭化水素化合物とを反応させてなる潤滑機能付与剤
を内容とするものである。
That is, the present invention provides an organosilicon compound having at least one hydrogen group, and a hydrocarbon compound having at least one double bond that reacts with the hydrogen group and having 18 or more carbon atoms. It contains a lubricant function-imparting agent obtained by reacting

【0007】少なくとも1個の水素基を有するシリコー
ン化合物としては、ポリメチルハイドロジェンシロキサ
ン、メチルハイドロジェンシロキサン−ジメチルシロキ
サンコポリマー等が挙げられる。また、二重結合を少な
くとも1個有する炭素数18以上の炭化水素化合物とし
ては、α−オレフィン、ポリエチレンワックス、1,4
−ポリブタジエン、1,2−ポリブタジエン、ポリブテ
ン等、及びこれらの混合物が挙げられる。炭素数が18
未満のものとの反応物ではワックスとの相溶性が悪くな
る。この観点から、炭素数が18以上、望ましくは24
〜40の炭化水素化合物が用いられる。
Examples of the silicone compound having at least one hydrogen group include polymethyl hydrogen siloxane and methyl hydrogen siloxane-dimethyl siloxane copolymer. Further, as the hydrocarbon compound having at least one double bond and having 18 or more carbon atoms, α-olefin, polyethylene wax, 1,4
-Polybutadiene, 1,2-polybutadiene, polybutene, etc. and mixtures thereof. 18 carbons
If the reaction product is less than less than the above, the compatibility with the wax becomes poor. From this viewpoint, the number of carbon atoms is 18 or more, preferably 24.
~ 40 hydrocarbon compounds are used.

【0008】変性シリコーン化合物の合成例を示すと、
ポリメチルハイドロジェンシロキサン(メチルハイドロ
ジェンシロキサン−ジメチルシロキサンコポリマーも含
む)と末端にビニル基1個を有するα−オレフィンを混
合し、触媒として塩化白金酸を添加し、加温し付加反応
させる。
A synthetic example of the modified silicone compound is as follows:
Polymethyl hydrogen siloxane (including methyl hydrogen siloxane-dimethyl siloxane copolymer) and α-olefin having one vinyl group at the end are mixed, chloroplatinic acid is added as a catalyst, and the mixture is heated to carry out an addition reaction.

【0009】この反応は、メチルハイドロジェンシロキ
サンのもつ水素基にα−オレフィンを付加させるもので
あるが、すべての水素基に付加させることは難しい。そ
こで、より熱安定性に優れたものにする場合は、α−オ
レフィンを最大限に付加させた後、残る水素基にプロピ
レンを付加させて水素基を封鎖することもできる。いず
れにしても、得られた反応生成物はアセトン等により数
回洗浄して精製される。
In this reaction, α-olefin is added to the hydrogen group of methyl hydrogen siloxane, but it is difficult to add to all hydrogen groups. Therefore, in order to obtain more excellent thermal stability, after the α-olefin is added to the maximum, propylene can be added to the remaining hydrogen groups to block the hydrogen groups. In any case, the obtained reaction product is purified by washing with acetone or the like several times.

【0010】本発明の潤滑機能付与剤は、二重結合を少
なくとも1個有する炭化水素化合物として炭素数18以
上のものを使用して、これを少なくとも1個の水素基を
有する有機珪素化合物に付加反応させているので、通常
のシリコーンオイルと異なり、ワックス類との相溶性が
良好であるという特徴を有する。更にまた、シリコーン
化合物のもつ撥水性、防汚性、艶出し効果等も発現す
る。本発明の潤滑機能付与剤は、単独で、又はワックス
類と混合して用いられる。更にはこれらにアルミニウ
ム、ガリウム等の金属粒子、カーボン、粘土鉱物等の無
機物や有機系の粒状体を混合することもできる。これら
は例えばスキー用ワックスとして用いられる。またカー
ワックス用に混合して、ワックスがけの作業性向上を図
るとともに、潤滑性は勿論のこと、撥水性、防汚性、艶
出し性も付与する。更に、単独で又はワックス類と混合
して、溶剤系又は乳化系で靴クリームや、家具等の清掃
用の化学雑巾の含浸剤として使用される。
The lubricating function-imparting agent of the present invention uses a hydrocarbon compound having at least one double bond and having 18 or more carbon atoms, and adds this to an organosilicon compound having at least one hydrogen group. Since it is reacted, it has a characteristic that it has good compatibility with waxes unlike ordinary silicone oils. Furthermore, the water repellency, antifouling property, and polishing effect of the silicone compound are also exhibited. The lubricant function-imparting agent of the present invention is used alone or in a mixture with waxes. Further, metal particles of aluminum, gallium, etc., inorganic materials such as carbon, clay minerals, etc. or organic particles can be mixed with these. These are used as ski waxes, for example. Further, it is mixed for car wax to improve the workability of waxing, and in addition to lubricity, it also imparts water repellency, antifouling property, and glossiness. Further, it is used alone or in a mixture with waxes as a solvent-based or emulsified system as an impregnating agent for shoe creams and chemical wipes for cleaning furniture and the like.

【0011】単独、溶剤系あるいは乳化系で直接処理表
面に塗工して使用する場合、処理表面の表面状態や変性
シリコーン化合物のシリコーン含有量にもよるが、例え
ばシリコーン含有量が40〜60%の場合、0.5〜7
g/m2程度で良好な潤滑機能が付与される。
When it is used alone or by directly coating it on a surface to be treated in a solvent system or an emulsion system, it depends on the surface condition of the treated surface and the silicone content of the modified silicone compound. In case of 0.5 to 7
A good lubrication function is provided at about g / m 2 .

【0012】またワックスと混合して使用する場合は、
その使用目的にもよるが、ワックスに対し0.5〜80
重量%の混合量で充分な潤滑機能が発揮される。
When used by mixing with wax,
Depending on the purpose of use, it is 0.5 to 80 for wax.
Sufficient lubrication function is exhibited with the mixing amount of wt%.

【0013】更にまた、天然ゴム、天然樹脂や合成樹脂
に添加して、これらの表面の改質を目的とする場合は、
これらに対して1〜8重量%添加する。
Furthermore, in the case of adding to natural rubber, natural resin or synthetic resin for the purpose of modifying the surface of these,
1 to 8% by weight is added to these.

【0014】[0014]

【実施例】以下、本発明を実施例及び比較例に基づき更
に詳細に説明するが、本発明はこれらにより何ら制限さ
れるものではない。尚、以下の記載において、「部」及
び「%」は特に断らない限り、「重量部」、「重量%」
をそれぞれ意味する。
EXAMPLES The present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. In the following description, "parts" and "%" are "parts by weight" and "% by weight" unless otherwise specified.
Means respectively.

【0015】実施例1 メチルハイドロジェンシロキサン−ジメチルシロキサン
コポリマー(P=300、MW=22000)53.2
部、α−オレフィン(「ダイヤレン−30」、三菱化成
株式会社製、炭素数28〜52(30〜36主体))4
6.8部、0.1%H2 PtCl6 ・6H2 O イソプ
ロピルアルコール溶液8部を反応器に仕込み、120℃
で9時間付加反応させ、更に130℃で18時間反応さ
せた。反応生成物の粘度が約10000cpsに達した
時反応を停止させた。反応生成物はアセトンで3回洗浄
し、精製乾燥した。得られた変性シリコーン化合物のシ
リコーン含有率は53.2%、分子量は32000で、
乳白色の固体であった。
Example 1 Methylhydrogensiloxane-dimethylsiloxane copolymer (P = 300, MW = 22000) 53.2
Part, α-olefin (“Dialene-30”, manufactured by Mitsubishi Kasei Co., Ltd., carbon number 28 to 52 (mainly 30 to 36)) 4
6.8 parts, 8 parts of 0.1% H 2 PtCl 6 .6H 2 O isopropyl alcohol solution was charged into a reactor and 120 ° C.
The reaction was carried out for 9 hours at 130 ° C. and then at 130 ° C. for 18 hours. The reaction was stopped when the viscosity of the reaction product reached about 10,000 cps. The reaction product was washed 3 times with acetone, purified and dried. The obtained modified silicone compound had a silicone content of 53.2% and a molecular weight of 32000.
It was a milky white solid.

【0016】得られた変性シリコーン化合物を1,1,
1−トリクロロエタンに、5%の濃度で溶解したものを
(A)とした。また、得られた変性シリコーン化合物と
「パラフィンワックス140」(日本精蝋株式会社製)
とを1:1(重量比)で混合し、1,1,1−トリクロ
ロエタンに5%の濃度で溶解したものを(B)とした。
The modified silicone compound thus obtained was
What was dissolved in 1-trichloroethane at a concentration of 5% was designated as (A). Further, the obtained modified silicone compound and "paraffin wax 140" (manufactured by Nippon Seiro Co., Ltd.)
Was mixed at a ratio of 1: 1 (weight ratio) and dissolved in 1,1,1-trichloroethane at a concentration of 5% to obtain (B).

【0017】得られた溶解物(A),(B)をそれぞれ
上質紙(120g/m2)のフェルト面上に固形物量として
1.5g/m2塗工した。その塗工物について塗工面と塗工
面の静摩擦係数及び動摩擦係数を測定した。結果を表1
に示す。表1から明らかな如く、変性シリコーン化合物
単独、ワックスとのブレンドのいずれにおいても、良好
な潤滑機能付与効果を示した。
The obtained melts (A) and (B) were coated on the felt surface of each of fine paper (120 g / m 2 ) as a solid content of 1.5 g / m 2 . The static friction coefficient and the dynamic friction coefficient between the coated surface and the coated surface of the coated product were measured. The results are shown in Table 1.
Shown in. As is clear from Table 1, both the modified silicone compound alone and the blend with the wax exhibited a good lubricating function imparting effect.

【0018】比較例1 実施例1で使用したのと同じパラフィンワックスを1,
1,1−トリクロロエタンに5%溶解したものを(C)
とした。シリコーンとしてシリコーンオイル「KF96
−1000CS」(信越化学工業株式会社製)を1,
1,1−トリクロロエタンに5%溶解したものを(D)
とした。
COMPARATIVE EXAMPLE 1 The same paraffin wax used in Example 1 was
What was dissolved 5% in 1,1-trichloroethane (C)
And Silicone oil as silicone "KF96
-1000CS "(made by Shin-Etsu Chemical Co., Ltd.)
What was dissolved 5% in 1,1-trichloroethane (D)
And

【0019】得られた溶解物(C),(D)をそれぞれ
実施例1と同様にして上質紙上に1.5g/m2塗工し、実
施例1と同様にして、塗工面と塗工面の静摩擦係数及び
動摩擦係数を測定した。結果を表1に示す。
The obtained melts (C) and (D) were coated on high-quality paper at 1.5 g / m 2 in the same manner as in Example 1, and the coated surface and the coated surface were prepared in the same manner as in Example 1. The coefficient of static friction and the coefficient of dynamic friction were measured. The results are shown in Table 1.

【0020】比較例2 実施例1で使用したメチルハイドロジェンシロキサン−
ジメチルシロキサンシリコーンコポリマー51.9部、
α−オレフィンとしてのヘキサデセン−1 48.1
部、0.1%H2 PtCl6 ・6H2 O イソプロピル
アルコール溶液8部を反応器に仕込み、120℃で9時
間反応させた。反応生成物の粘度が約5000cpsに
達した時反応を停止させた。得られた変性シリコーン化
合物は液体であり、シリコーン含有率は48.3%、分
子量は27000であった。
Comparative Example 2 Methylhydrogensiloxane used in Example 1
51.9 parts of dimethylsiloxane silicone copolymer,
Hexadecene-1 48.1 as α-olefin
Parts and 0.1 parts of 0.1% H 2 PtCl 6 .6H 2 O isopropyl alcohol solution were charged into a reactor and reacted at 120 ° C. for 9 hours. The reaction was stopped when the viscosity of the reaction product reached about 5000 cps. The obtained modified silicone compound was a liquid and had a silicone content of 48.3% and a molecular weight of 27,000.

【0021】得られた変性シリコーン化合物を、実施例
1と同様1,1,1−トリクロロエタンに5%溶解した
ものを(E)とした。さらに、実施例1と同様に上質紙
上に1.5g/m2塗工し、塗工面と塗工面の静摩擦係数、
及び動摩擦係数を測定した。結果を表1に示す。得られ
た変性シリコーン(E)はシリコーンオイル(D)と同
じく潤滑機能付与効果及びワックスとの相溶性が劣る。
また、ワックスは潤滑機能付与効果が劣る。
The modified silicone compound thus obtained was dissolved in 1,1,1-trichloroethane at a concentration of 5% as in Example 1 and designated as (E). Furthermore, as in Example 1, 1.5 g / m 2 was coated on high-quality paper, and the coefficient of static friction between the coated surface and the coated surface,
And the coefficient of dynamic friction was measured. The results are shown in Table 1. The obtained modified silicone (E) is inferior in lubrication function imparting effect and compatibility with wax like the silicone oil (D).
In addition, wax is inferior in lubrication function imparting effect.

【0022】[0022]

【表1】 [Table 1]

【0023】静(動)摩擦係数:上質紙フェルト面に各
試料を塗工した塗工面と塗工面の摩擦係数を測定した。
測定条件は、荷重1Kgかけ、引張り速度30mm/minとし
た。 耐ワックス相溶性:ワックスとして「パラフィンワック
ス140」(日本精蝋株式会社製、m.p.61℃)を
使用し、相溶性を○、△、×で評価した。
Static (dynamic) friction coefficient: The coefficient of friction between the coated surface and the coated surface in which each sample was coated on the fine paper felt surface was measured.
The measurement conditions were a load of 1 kg and a tensile speed of 30 mm / min. Wax compatibility resistance: "paraffin wax 140" (manufactured by Nippon Seiro Co., Ltd., mp 61 ° C.) was used as a wax, and the compatibility was evaluated by ◯, Δ, and x.

【0024】実施例2 ポリメチルハイドロジェンシロキサン(P=350、M
W=26000)47.2部、実施例1で使用したのと
同じα−オレフィン52.8部、0.1%H2 PtCl
6 ・6H2 O イソプロピルアルコール溶液8部を反応
器に仕込み、120℃で9時間反応させた。さらに、
0.1%H2 PtCl6 ・6H2 O イソプロピルアル
コール溶液4部を追加し、反応器内にプロピレンガスを
吹き込み120℃で5時間反応させた。反応生成物の粘
度が約10000cpsに達した時反応を停止させた。
反応生成物は、アセトンで3回洗浄し、精製乾燥した。
得られた変性シリコーン化合物のシリコーン含有率は4
7.2%であった。分子量は38000で乳白色の固体
であった。
Example 2 Polymethyl hydrogen siloxane (P = 350, M
W = 26000) 47.2 parts, the same α-olefin as used in Example 1 52.8 parts, 0.1% H 2 PtCl
G of 6 · 6H 2 O isopropyl alcohol solution 8 parts to the reactor and allowed to react for 9 hours at 120 ° C.. further,
4 parts of 0.1% H 2 PtCl 6 .6H 2 O isopropyl alcohol solution was added, and propylene gas was blown into the reactor to react at 120 ° C. for 5 hours. The reaction was stopped when the viscosity of the reaction product reached about 10,000 cps.
The reaction product was washed with acetone three times and purified and dried.
The resulting modified silicone compound has a silicone content of 4
It was 7.2%. It had a molecular weight of 38,000 and was a milky white solid.

【0025】得られた変性シリコーン化合物3部、ステ
アリン酸5部、カルナウバワックス20部をミネラルス
ピリット72部に溶解し、艶出しワックスを得た。この
ものを表面平滑なステンレス板に塗工し、乾燥後の拭き
取り作業性、拭き取り後の艶出し効果及び撥水性を観察
した。結果を表2に示す。変性シリコーン化合物添加に
よる潤滑機能付与効果により、拭き取り作業性が著しく
向上した。さらに、撥水性も優れたものであった。
3 parts of the obtained modified silicone compound, 5 parts of stearic acid, and 20 parts of carnauba wax were dissolved in 72 parts of mineral spirit to obtain a lustrous wax. This product was applied to a stainless plate having a smooth surface, and the workability of wiping after drying, the polishing effect after wiping and the water repellency were observed. The results are shown in Table 2. The addition of the modified silicone compound has the effect of imparting a lubricating function, and the wiping workability has been significantly improved. Furthermore, the water repellency was also excellent.

【0026】比較例3 実施例2で合成した変性シリコーンを添加しない以外
は、実施例2と同様にして艶出しワックスを得、実施例
2と同様にして、拭き取り作業性と、艶出し効果、撥水
性を観察した。結果を表2に示す。
Comparative Example 3 A lustrous wax was obtained in the same manner as in Example 2 except that the modified silicone synthesized in Example 2 was not added. In the same manner as in Example 2, wiping workability and glazing effect, The water repellency was observed. The results are shown in Table 2.

【0027】[0027]

【表2】 [Table 2]

【0028】拭き取り作業性:ステンレス板に塗工乾燥
後、タオルで塗工面を拭き取り、その容易さを評価し
た。 撥水性:水滴を落とし、そのはじき具合を観察した。 ◎:非常に優れている △:やや不良である ×:不良である
Wiping workability: After coating and drying on a stainless steel plate, the coated surface was wiped off with a towel, and its ease was evaluated. Water repellency: Water drops were dropped and the repellency was observed. ⊚: Very good Δ: Slightly bad ×: Bad

【0029】[0029]

【発明の効果】叙上の通り、本発明によれば、単独もし
くは混合系、又は溶剤系、乳化系で優れた潤滑機能付与
効果を発揮し、しかも良好なワックス相溶性を有する。
As described above, according to the present invention, an excellent lubricating function imparting effect is exhibited in a single or mixed system, or in a solvent system or an emulsion system, and a good wax compatibility is exhibited.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 C10M 107:50 105:04) C10N 50:08 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location C10M 107: 50 105: 04) C10N 50:08

Claims (2)

【特許請求の範囲】[Claims] 【請求項1】 少なくとも1個の水素基を有する有機珪
素化合物と、該水素基と反応する二重結合を少なくとも
1個有する炭素数18以上の炭化水素化合物とを反応さ
せてなる潤滑機能付与剤。
1. A lubricating function-imparting agent obtained by reacting an organosilicon compound having at least one hydrogen group with a hydrocarbon compound having at least one double bond that reacts with the hydrogen group and having 18 or more carbon atoms. ..
【請求項2】 ポリメチルハイドロジェンシロキサン及
び/又はメチルハイドロジェンシロキサンージメチルシ
ロキサンコポリマーに、炭素数18以上のα−オレフィ
ンを付加してなる請求項1記載の潤滑機能付与剤。
2. The lubrication function-imparting agent according to claim 1, wherein the α-olefin having 18 or more carbon atoms is added to polymethylhydrogensiloxane and / or methylhydrogensiloxane-dimethylsiloxane copolymer.
JP22890091A 1991-08-13 1991-08-13 Lubrication function imparting agent Expired - Lifetime JP3078613B2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP22890091A JP3078613B2 (en) 1991-08-13 1991-08-13 Lubrication function imparting agent
EP92102196A EP0527286A1 (en) 1991-08-13 1992-02-10 Lubricant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22890091A JP3078613B2 (en) 1991-08-13 1991-08-13 Lubrication function imparting agent

Publications (2)

Publication Number Publication Date
JPH0543885A true JPH0543885A (en) 1993-02-23
JP3078613B2 JP3078613B2 (en) 2000-08-21

Family

ID=16883621

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22890091A Expired - Lifetime JP3078613B2 (en) 1991-08-13 1991-08-13 Lubrication function imparting agent

Country Status (1)

Country Link
JP (1) JP3078613B2 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09216948A (en) * 1996-02-08 1997-08-19 Kao Corp Modified polysiloxane and its production
JPH11506493A (en) * 1995-06-06 1999-06-08 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー Anionic polymerized block copolymer of ethylene and cyclic siloxane monomer
US7226502B2 (en) * 2003-04-10 2007-06-05 Clariant Finance (Bvi) Limited High softening temperature synthetic alkylsilicone wax
JP2009531523A (en) * 2006-03-29 2009-09-03 タートル・ワツクス・インコーポレイテツド Liquid polishing composition and kit
JP2016532745A (en) * 2013-07-29 2016-10-20 スリーエム イノベイティブ プロパティズ カンパニー Release film by solvent-free extrusion process
US11970651B2 (en) 2018-02-20 2024-04-30 Daikin Industries, Ltd. Surface treatment agent

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR200495744Y1 (en) * 2020-12-28 2022-08-08 김성태 Cooler bag

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5682894A (en) * 1979-12-11 1981-07-06 Toshiba Silicone Co Ltd Silicone grease for electrical contact
JPS633076A (en) * 1986-06-24 1988-01-08 Goyo Shiko Kk Releasant and production of release paper using same
JPH0264115A (en) * 1988-08-30 1990-03-05 Nippon Unicar Co Ltd Polydialkylosiloxane-olefin block copolymer, production thereof, composition containing the same copolymer and molded article made from the composition
JPH02140295A (en) * 1988-11-19 1990-05-29 Kao Corp Lubricating oil useful in fluorocarbon atmosphere

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5682894A (en) * 1979-12-11 1981-07-06 Toshiba Silicone Co Ltd Silicone grease for electrical contact
JPS633076A (en) * 1986-06-24 1988-01-08 Goyo Shiko Kk Releasant and production of release paper using same
JPH0264115A (en) * 1988-08-30 1990-03-05 Nippon Unicar Co Ltd Polydialkylosiloxane-olefin block copolymer, production thereof, composition containing the same copolymer and molded article made from the composition
JPH02140295A (en) * 1988-11-19 1990-05-29 Kao Corp Lubricating oil useful in fluorocarbon atmosphere

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11506493A (en) * 1995-06-06 1999-06-08 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー Anionic polymerized block copolymer of ethylene and cyclic siloxane monomer
JPH09216948A (en) * 1996-02-08 1997-08-19 Kao Corp Modified polysiloxane and its production
US7226502B2 (en) * 2003-04-10 2007-06-05 Clariant Finance (Bvi) Limited High softening temperature synthetic alkylsilicone wax
JP2009531523A (en) * 2006-03-29 2009-09-03 タートル・ワツクス・インコーポレイテツド Liquid polishing composition and kit
JP2016532745A (en) * 2013-07-29 2016-10-20 スリーエム イノベイティブ プロパティズ カンパニー Release film by solvent-free extrusion process
US11970651B2 (en) 2018-02-20 2024-04-30 Daikin Industries, Ltd. Surface treatment agent

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