JPS61195138A - Easily water dispersible and soluble high polymer substance and production thereof - Google Patents

Easily water dispersible and soluble high polymer substance and production thereof

Info

Publication number
JPS61195138A
JPS61195138A JP3698985A JP3698985A JPS61195138A JP S61195138 A JPS61195138 A JP S61195138A JP 3698985 A JP3698985 A JP 3698985A JP 3698985 A JP3698985 A JP 3698985A JP S61195138 A JPS61195138 A JP S61195138A
Authority
JP
Japan
Prior art keywords
water
polymer substance
high polymer
composition according
weight
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
Application number
JP3698985A
Other languages
Japanese (ja)
Inventor
Tadao Maruyama
丸山 忠雄
Kazuyoshi Hayakawa
早川 和良
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.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical 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
Application filed by Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Priority to JP3698985A priority Critical patent/JPS61195138A/en
Publication of JPS61195138A publication Critical patent/JPS61195138A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:A easily water dispersible and soluble high polymer substance composition, obtained by heat-treating a mixture of a water-soluble high polymer substance and an organosilane compound (partial hydrolyzate condensate), spraying an aqueous solution of a surface active agent, and drying the mixture. CONSTITUTION:(A) 100pts.wt. water-soluble high polymer substance, e.g., cellu lose ether suh as methyl cellulose, hydroxypropylmethyl cellulose, etc. is blended with (B) 0.1-3pts.wt. organosilane compound shown by the formula RSi(X)3 (R is 1-10C monofunctional hydrocarbon; X is hydrolyzable organic group, such as alkoxy, or acyloxy) or its partial hydrolyzate condensate directly or after diluting it with an organic solvent, heat-treated, and sprayed with (C) 0.5-7pts.wt. surface active agent, preferably alkyl sulfate or polyoxyethylene nonyl phenyl ether as an aqueous solution, to give the aimed composition.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は水鳥分散・溶解性高分子物質組成物およびその
製造方法に係わり、詳しくはセルロースエーテル等の水
溶性高分子物質の粉状体を直接水に投入しても、何らま
まこを形成することなくスムースに分散・溶解し完全な
水溶液となる該組成物の提供を目的とする。
DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a waterfowl dispersion/soluble polymer substance composition and a method for producing the same. The object of the present invention is to provide a composition that smoothly disperses and dissolves without forming any lumps even when directly poured into water, and becomes a complete aqueous solution.

(従来の技術) 従来、セルロースエーテル等の水溶性高分子物質を水に
溶解させるには、直接の投入では水との親和性が強く、
粉体が水に濡れると粒子表面がただちに高粘着液で被わ
れ水が中に入っていかず、ままこが生じるため1通常、
熱ゲル化性を利用して熱湯に分散させ、冷却、かくはん
する方法がとられている。
(Prior art) Conventionally, in order to dissolve water-soluble polymer substances such as cellulose ether in water, direct injection has a strong affinity with water;
When powder gets wet with water, the surface of the particles is immediately covered with a highly adhesive liquid, preventing water from penetrating and causing lumps.1.
A method of dispersing it in hot water, cooling it, and stirring it takes advantage of its thermal gelation properties.

一方、セルロースエーテル等をグリオキザール処理する
ことは公知であり、このものは中性ないし酸性の水に分
散させることができ、分散後アルカリ性にすることによ
り溶解させることができるが、グリオキザール処理セル
ロースエーテルを直接アルカリ性の水に投入するとグリ
オキザールが分解してしまい、ままこが生じるので、目
的とするスムーズな分散・溶解は行われない。
On the other hand, it is known to treat cellulose ether etc. with glyoxal, which can be dispersed in neutral to acidic water and dissolved by making it alkaline after dispersion. If glyoxal is directly added to alkaline water, it will decompose and form lumps, so the desired smooth dispersion and dissolution will not occur.

セルロースエーテル等の水溶性高分子物質(粉体)を水
に投入してままこが生じる原因は、前記したように粉体
が水に濡れるとただちにその粒子表面が高粘着液に被わ
れ、水が粒子内へ浸透していかないためである。この水
溶性高分子物質の水に対する濡れを遅延させるためには
、シリコーン撥水剤、シランカップリング剤、シリコー
ン架橋剤等による処理が考えられるが、これらの処理の
みでは撥水効果だけが強くあられれ、処理粉体は水面に
浮いてしまい、溶解させることが困難である。一方粉体
粒子の水への分散性向上を期待して各種界面活性剤で処
理しても満足な溶解性を達成することはできない。
The reason why a water-soluble polymer substance (powder) such as cellulose ether is added to water causes lumps to form.As mentioned above, when the powder gets wet with water, the surface of the particle is immediately covered with a highly sticky liquid, and the water becomes sticky. This is because the particles do not penetrate into the particles. In order to delay the wetting of this water-soluble polymer substance with water, treatment with silicone water repellent agents, silane coupling agents, silicone crosslinking agents, etc. can be considered, but these treatments alone will not produce a strong water repellent effect. As a result, the treated powder floats on the water surface and is difficult to dissolve. On the other hand, even if powder particles are treated with various surfactants in hopes of improving their dispersibility in water, satisfactory solubility cannot be achieved.

(発明の構成) 本発明者らはかかる従来の不利欠点を解決すべく鋭意研
究を重ねた結果、水に対する濡れの特殊遅延剤と界面活
性剤の併用により、2成分の相乗効果が発揮され1分散
溶解性の際立ってすぐれた処理効果が達成されることを
見出し、本発明を完成した。
(Structure of the Invention) The present inventors have conducted extensive research to solve these conventional disadvantages, and have found that by using a special wetting retardant and a surfactant in combination, a synergistic effect of the two components is exhibited. The present invention was completed based on the discovery that a significantly superior treatment effect on dispersion solubility can be achieved.

すなわち、本発明は、 (イ)水溶性高分子物質     100重量部(ロ)
一般式 R31(X)  Φ−−・ (1)(式中のR
は炭素原子数1−10の1価炭化水素基、Xは加水分解
し得る有機基)で示される有機シラン化合物もしくはこ
の部分加水分解縮合物     0.1〜3重量部およ
び (ハ)界面活性剤       0.5〜7重量部から
なろ水鳥分散・溶解性高分子物質組成物およびその製造
方法に関するものである。
That is, the present invention includes (a) 100 parts by weight of a water-soluble polymeric substance (b)
General formula R31(X) Φ-- (1) (R in the formula
is a monovalent hydrocarbon group having 1 to 10 carbon atoms, and X is a hydrolyzable organic group) 0.1 to 3 parts by weight of an organic silane compound or a partially hydrolyzed condensate thereof; and (iii) a surfactant. The present invention relates to a waterfowl-dispersed/soluble polymer material composition containing 0.5 to 7 parts by weight and a method for producing the same.

本発明にかかわる高分子物質組成物は、酸性からアルカ
リ性の広範囲の水(セルロースエーテル等を凝集しない
塗料やエマルジョンあるいはその他の有機または無機物
質の溶解液、懸濁液等も含む)に直接分散溶解させるこ
とができる。したがフて、前記したグリオキザール処理
セルロースエーテルの如く、水に分散後pHをアルカリ
性に変えて溶解させるような手間は必要ない。
The polymer substance composition according to the present invention can be directly dispersed and dissolved in a wide range of water ranging from acidic to alkaline (including paints and emulsions that do not aggregate cellulose ether, etc., and solutions and suspensions of other organic or inorganic substances). can be done. Therefore, unlike the glyoxal-treated cellulose ether described above, it is not necessary to take the trouble of changing the pH to alkaline after dispersing it in water to dissolve it.

以下本発明をさらに詳しく説明する。The present invention will be explained in more detail below.

本発明で対象とされる(イ)水溶性高分子物質としては
、メチルセルロース、ヒドロキシプロピルメチルセルロ
ース、ヒドロキシエチルエチルセルロース、ヒドロキシ
エチルセルロース、ヒドロキシプロピルセルロースなど
で例示される各種セルロースエーテルのほか、ポリビニ
ルアルコール、カルボキシメチルセルロース、でんぷん
、カゼイン、さらには粉末エマルジョン、およびそれら
の各種水溶性誘導体があげられる。
(a) Water-soluble polymeric substances targeted by the present invention include various cellulose ethers such as methylcellulose, hydroxypropylmethylcellulose, hydroxyethylethylcellulose, hydroxyethylcellulose, and hydroxypropylcellulose, as well as polyvinyl alcohol and carboxymethylcellulose. , starch, casein, as well as powder emulsions and various water-soluble derivatives thereof.

つざに本発明で使用される(口)成分は、上記した水溶
性高分子物質の水に対する濡れ性を遅延させる働きを示
すものであり、本発明において重要とされる成分である
。一般式(1)中のRは炭素原子数1−10の1価炭化
水素基、たとえばメチル基、エチル基、プロピル基、フ
ェニル基等が例示される。また式中のXは加水分解し得
る有機基、たとえばメトキシ基、エトキシ基などのアシ
ロキシ基、式−0COR(Rはアルキル基)で示される
アシロキシ基、式−0NC(R)(R’)(式中のR,
R’はアルキル基)で示されるケトオキシム基等が例示
される。
Finally, the (oral) component used in the present invention is an important component in the present invention, as it functions to retard the wettability of the water-soluble polymeric substance described above to water. R in the general formula (1) is exemplified by a monovalent hydrocarbon group having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, a propyl group, and a phenyl group. In addition, X in the formula is a hydrolyzable organic group, such as an acyloxy group such as a methoxy group or an ethoxy group, an acyloxy group represented by the formula -0COR (R is an alkyl group), or a formula -0NC(R)(R')( R in the formula,
A ketooxime group represented by R' is an alkyl group is exemplified.

上記した(口)成分は空気中の水分等によって容易に部
分加水分解縮合する性質を有するが、このような部分加
水分解縮合物も本発明に有効に使用される。
The above-mentioned (mouth) components have the property of being easily partially hydrolyzed and condensed by moisture in the air, and such partially hydrolyzed condensates can also be effectively used in the present invention.

(ロ)成分は前記(イ)成分100重量部当り、0.1
〜3重量部(好ましくは0.5〜2重量部)の範囲で使
用することが望ましい、0.1重量部以下では濡れ性遅
延化の効果が小さく、一方3重量部以上添加しても分散
会溶解性をさらに向上させることはできない。
Component (b) is 0.1 per 100 parts by weight of component (a).
It is desirable to use the amount in the range of ~3 parts by weight (preferably 0.5 to 2 parts by weight). If it is less than 0.1 part by weight, the effect of retarding the wettability will be small, while if it is added more than 3 parts by weight, it will not cause dispersion. Solubility cannot be further improved.

上記した(口)成分のみでは本発明の目的を達成するこ
とができず、さらに(ハ)界面活性剤を使用することに
よりはじめて容易にして迅速な分散・溶解性を得ること
ができる。この界面活性剤としては各種のものを使用し
得るが、特にはアルキル硫酸塩およびポリオキシエチレ
ンノニルフェニルエーテルが好適とされる。
The object of the present invention cannot be achieved with the above-mentioned (1) component alone; furthermore, by using (3) a surfactant, it is possible to easily and quickly obtain dispersion and solubility. Various types of surfactants can be used, but alkyl sulfates and polyoxyethylene nonylphenyl ether are particularly preferred.

(ハ)成分は前記(イ)成分100重量部当り、0.5
〜7重量部(好ましくは1〜5重量□部)の範囲で使用
することが望ましい、 O,S @置部以下では分散向
上効果が小さく、一方7重量部以上の多量添加してもそ
れ以上の効果は得られない。
Component (c) is 0.5 per 100 parts by weight of component (a).
It is desirable to use it in the range of ~7 parts by weight (preferably 1 to 5 parts by weight).If the amount of O,S is less than 1 part by weight, the effect of improving dispersion will be small; effect cannot be obtained.

(イ)水溶性高分子物質に対する(口)成分の添加配合
は、(ロ)成分の所定量を直接にあるいは適宜有機溶媒
で希釈して均一に添加混合することにより行われるが、
単に混合するのみでなく少量の水分の存在下に加熱処理
(たとえば100℃で1時間程度)することが望ましい
、この加熱処理を行うことにより、界面活性剤添加と相
まって一段とすぐれた分散・溶解性向上効果が得られる
(b) The addition and blending of the (b) component to the water-soluble polymeric substance is carried out by uniformly adding and mixing a predetermined amount of the (b) component either directly or diluted with an appropriate organic solvent.
It is desirable not only to simply mix but also to heat-treat in the presence of a small amount of water (for example, at 100°C for about 1 hour). By performing this heat-treating, combined with the addition of a surfactant, the dispersion and solubility are even better. An improvement effect can be obtained.

(ハ)界面活性剤の添加は上記(ロ)成分と同時に行う
よりも上記加熱処理後に行うことが望ましい、すなわち
(ロ)成分の添加が終了したのち、界面活性剤の水溶液
を所定量噴霧し乾燥する(たとえば100℃で1時間程
度)ことにより、目的とする水易分散・溶解性高分子物
質が得られる。
(c) It is preferable to add the surfactant after the above heat treatment rather than at the same time as the above (b) component. In other words, after the addition of the (b) component is completed, a predetermined amount of an aqueous solution of the surfactant is sprayed. By drying (for example, at 100° C. for about 1 hour), the desired water-easily dispersible and soluble polymeric substance can be obtained.

つぎに具体的実施例をあげる。ただし以下の各側におい
て次の略記号を用いた。
Next, specific examples will be given. However, the following abbreviations are used for each side below.

[セルロースエーテル] o  90SH3万: 信越化学工業製ヒドロキシプロ
ピルメチルセル口 −ス、2%水溶液粘度約 3万cps(25℃) o  90SH3000:@越化学工業製ヒドロキシプ
ロピルメチルセル ロース、2%水溶液粘度 約3000cps (25℃) o  65SH4000:  信越化学工業製ヒドロキ
シプロピルメチルセ ルロース、2%水溶液粘 度約4000 cps  (25 ℃) osM−4000:  信越化学工業製メチルセルロー
ス、2%水溶液 粘度的4000cps  (2 5℃) [有機シラン化合物] Oシラン化合物C: [界面活性剤】 a  DBS−Na:  I’7”シルベンゼンスルホ
ン酸ナトリウム oNs−208=  ポリオキシエチレンノニルフェニ
ルエーテル oLS−Ha:   ラウリル硫酸ナトリウム実施例1 第1表に示すとおり、セルロースエーテル(粉末)10
0gK、有機シラン化合物2gを溶液として加えて均一
に混合し、100℃で1時間加熱処理した。つぎにこの
ものに界面活性剤4gを水溶液として噴霧し100℃で
1時間乾燥した。 −このようにして得た組成物につい
て水への溶解試験を行ったところ、第1表に示すとおり
の結果が得られた。なお、同表には比較データを併記し
た。
[Cellulose ether] o 90SH3000: Hydroxypropyl methyl cellulose manufactured by Shin-Etsu Chemical Co., Ltd., 2% aqueous solution viscosity of approximately 30,000 cps (25°C) o 90SH3000: @ Hydroxypropyl methylcellulose manufactured by Etsu Chemical Co., Ltd., 2% aqueous solution viscosity of approximately 3000 cps (25℃) o 65SH4000: Shin-Etsu Chemical Co., Ltd. hydroxypropyl methyl cellulose, 2% aqueous solution viscosity of about 4000 cps (25℃) osM-4000: Shin-Etsu Chemical Co., Ltd. methylcellulose, 2% aqueous solution viscosity 4000 cps (25℃) [Organosilane Compound] O silane compound C: [Surfactant] a DBS-Na: I'7'' Sodium sylbenzene sulfonate oNs-208= Polyoxyethylene nonylphenyl ether oLS-Ha: Sodium lauryl sulfate Example 1 Table 1 As shown, cellulose ether (powder) 10
0 g K and 2 g of an organic silane compound were added as a solution, mixed uniformly, and heat-treated at 100° C. for 1 hour. Next, 4 g of a surfactant was sprayed as an aqueous solution onto this material and dried at 100° C. for 1 hour. - When the composition thus obtained was subjected to a dissolution test in water, the results shown in Table 1 were obtained. The table also includes comparative data.

[溶解試験] 300mJl)−ルビーカーに水1000mjL入れ、
かくはん機を取り付けてかくはん羽根を1100rpで
回転させながら、ここに試料を2g(1%)または4g
(2%)投入し、分散・溶解性を調べた。
[Dissolution test] 300mJl)-Pour 1000mJL of water into a ruby car,
Attach a stirrer and rotate the stirring blade at 1100 rpm, and add 2g (1%) or 4g of the sample here.
(2%) and examined the dispersion and solubility.

◎ 分散・溶解性良好 ○ 分散・溶解性良好、ただしわずかにままこ生じるこ
ともある △ ままこ少量生じる X ままこ多量生じる 実施例2 セルロースエーテル(90SH3000)に対する有機
シラン化合物および界面活性剤の各添加量、加熱および
乾燥条件をそれぞれ第2表に示すとおりとしたほかは前
例に準じて添加処理を行い、溶解試験を行った。ただし
、有機シラン化合物添加の際の加熱温度および時間と、
界面活性剤添加の際の乾燥温度および時間はそれぞれ同
条件とした。
◎ Good dispersion and solubility ○ Good dispersion and solubility, but slight lumps may occur △ Small amount of lumps produced The addition treatment was carried out in the same manner as in the previous example, except that the amount added, heating and drying conditions were as shown in Table 2, and a dissolution test was conducted. However, the heating temperature and time when adding the organic silane compound,
The drying temperature and time when adding the surfactant were the same.

結果は第2表に示すとおりであった。The results were as shown in Table 2.

実施例3 前記第1表中の実験No、11.および第2表中の実験
No、20で得たそれぞれの加熱・乾燥処理セルロース
エーテルについて、第3表に示す性質の水液に投入して
溶解試験を行った。
Example 3 Experiment No. 11 in Table 1 above. The heat-dried cellulose ethers obtained in Experiments No. 20 and 20 in Table 2 were put into an aqueous solution having the properties shown in Table 3 for a dissolution test.

結果は第3表に示すとおりであった。The results were as shown in Table 3.

第   3   表 gVAエマルジョン:エチレン−酢酸ビニル共重合エマ
ルジョン、固形分25%
Table 3 gVA emulsion: Ethylene-vinyl acetate copolymer emulsion, solid content 25%

Claims (1)

【特許請求の範囲】 1、(イ)水溶性高分子物質100重量部 (ロ)一般式RSi(X)_3 (式中のRは炭素原子数1〜10の1価 炭化水素基、Xは加水分解し得る有機基 )で示される有機シラン化合物もしくは この部分加水分解縮合物0.1〜3重量部 および (ハ)界面活性剤0.5〜7重量部 からなる水易分散・溶解性高分子物質組成物。 2、前記水溶性高分子物質がセルロースエーテルである
特許請求の範囲第1項記載の組成物。 3、前記一般式のRがメチル基であり、Xが−OCH_
3、−OCOCH_3または −ONC(CH_3)(C_2H_5)である特許請求
の範囲第1項記載の組成物。 4、前記界面活性剤がアルキル硫酸塩もしくはポリオキ
シエチレンノニルフェニルエーテルである特許請求の範
囲第1項記載の組成物。 5、水溶性高分子物質100重量部に、一般式RSi(
X)_3(式中のRは炭素原子数1〜10の1価炭化水
素基、Xは加水分解し得る有機基)で示される有機シラ
ン化合物もしくはこの部分加水分解縮合物を0.1〜3
重量部加えて加熱処理し、ついで界面活性剤の水溶液を
噴霧し乾燥することを特徴とする水易分散・溶解性高分
子物質の製造方法 6、前記水溶性高分子物質がセルロースエーテルである
特許請求の範囲第5項記載の組成物。 7、前記一般式のRがメチル基であり、Xが−OCH_
3、−OCOCH_3または −ONC(CH_3)(C_2H_5)である特許請求
の範囲第5項記載の組成物。 8、前記界面活性剤がアルキル硫酸塩もしくはポリオキ
シエチレンノニルフェニルエーテルである特許請求の範
囲第5項記載の組成物。
[Claims] 1. (a) 100 parts by weight of a water-soluble polymeric substance (b) General formula RSi(X)_3 (R in the formula is a monovalent hydrocarbon group having 1 to 10 carbon atoms, and X is a monovalent hydrocarbon group having 1 to 10 carbon atoms; Hydrolyzable organic group) or a partially hydrolyzed condensate thereof (0.1 to 3 parts by weight) and (iii) a surfactant with high water dispersibility and solubility. Molecular substance composition. 2. The composition according to claim 1, wherein the water-soluble polymeric substance is cellulose ether. 3. R in the above general formula is a methyl group, and X is -OCH_
3. The composition according to claim 1, which is -OCOCH_3 or -ONC(CH_3)(C_2H_5). 4. The composition according to claim 1, wherein the surfactant is an alkyl sulfate or polyoxyethylene nonylphenyl ether. 5. To 100 parts by weight of a water-soluble polymer substance, add the general formula RSi (
X)_3 (in the formula, R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydrolyzable organic group) or a partially hydrolyzed condensate thereof, to 0.1 to 3
A method for producing a water-readily dispersible and soluble polymeric substance 6, characterized in that the water-soluble polymeric substance is a cellulose ether, the method comprising adding parts by weight, heating, and then spraying an aqueous solution of a surfactant and drying the patent. The composition according to claim 5. 7. R in the above general formula is a methyl group, and X is -OCH_
3. The composition according to claim 5, which is -OCOCH_3 or -ONC(CH_3)(C_2H_5). 8. The composition according to claim 5, wherein the surfactant is an alkyl sulfate or polyoxyethylene nonylphenyl ether.
JP3698985A 1985-02-26 1985-02-26 Easily water dispersible and soluble high polymer substance and production thereof Pending JPS61195138A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP3698985A JPS61195138A (en) 1985-02-26 1985-02-26 Easily water dispersible and soluble high polymer substance and production thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3698985A JPS61195138A (en) 1985-02-26 1985-02-26 Easily water dispersible and soluble high polymer substance and production thereof

Publications (1)

Publication Number Publication Date
JPS61195138A true JPS61195138A (en) 1986-08-29

Family

ID=12485154

Family Applications (1)

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JP3698985A Pending JPS61195138A (en) 1985-02-26 1985-02-26 Easily water dispersible and soluble high polymer substance and production thereof

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4842850A (en) * 1987-05-18 1989-06-27 The Procter & Gamble Company Hair care compositions
US4906459A (en) * 1987-10-23 1990-03-06 The Procter & Gamble Company Hair care compositions
US4983377A (en) * 1989-10-31 1991-01-08 The Procter & Gamble Company Silicone hairspray compositions
US4983383A (en) * 1988-11-21 1991-01-08 The Procter & Gamble Company Hair care compositions
US4983418A (en) * 1989-10-31 1991-01-08 The Procter & Gamble Company Silicone hairspray compositions
US5100657A (en) * 1990-05-01 1992-03-31 The Procter & Gamble Company Clean conditioning compositions for hair
WO2009025354A1 (en) 2007-08-22 2009-02-26 Lion Corporation Process for production of silane-modified cationized cellulose
WO2010055664A1 (en) 2008-11-12 2010-05-20 ライオン株式会社 Cleanser composition
JP2021014510A (en) * 2019-07-11 2021-02-12 株式会社富山環境整備 Composite material and method for manufacturing composite material

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5962601A (en) * 1982-09-01 1984-04-10 ヘキスト・アクチエンゲゼルシヤフト Manufacture of cellulose ether dispersable in aqueous medium

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5962601A (en) * 1982-09-01 1984-04-10 ヘキスト・アクチエンゲゼルシヤフト Manufacture of cellulose ether dispersable in aqueous medium

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4842850A (en) * 1987-05-18 1989-06-27 The Procter & Gamble Company Hair care compositions
US4906459A (en) * 1987-10-23 1990-03-06 The Procter & Gamble Company Hair care compositions
US4983383A (en) * 1988-11-21 1991-01-08 The Procter & Gamble Company Hair care compositions
US4983377A (en) * 1989-10-31 1991-01-08 The Procter & Gamble Company Silicone hairspray compositions
US4983418A (en) * 1989-10-31 1991-01-08 The Procter & Gamble Company Silicone hairspray compositions
US5100657A (en) * 1990-05-01 1992-03-31 The Procter & Gamble Company Clean conditioning compositions for hair
WO2009025354A1 (en) 2007-08-22 2009-02-26 Lion Corporation Process for production of silane-modified cationized cellulose
US8569263B2 (en) 2007-08-22 2013-10-29 Lion Corporation Method of producing silane-modified cationized cellulose
WO2010055664A1 (en) 2008-11-12 2010-05-20 ライオン株式会社 Cleanser composition
JP2021014510A (en) * 2019-07-11 2021-02-12 株式会社富山環境整備 Composite material and method for manufacturing composite material

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