JPH05320617A - New organic gelling agent - Google Patents
New organic gelling agentInfo
- Publication number
- JPH05320617A JPH05320617A JP15594392A JP15594392A JPH05320617A JP H05320617 A JPH05320617 A JP H05320617A JP 15594392 A JP15594392 A JP 15594392A JP 15594392 A JP15594392 A JP 15594392A JP H05320617 A JPH05320617 A JP H05320617A
- Authority
- JP
- Japan
- Prior art keywords
- gelling agent
- gel
- bisamide
- acid
- gelling
- 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
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、有機性ゲル化剤に関す
る。ここで、ゲル化剤とは、有機液体に添加することに
より、系に降伏値を与え、系の流動性を消失させる機能
を有する化合物の総称である。FIELD OF THE INVENTION The present invention relates to an organic gelling agent. Here, the gelling agent is a general term for compounds having a function of giving a yield value to the system and eliminating the fluidity of the system when added to the organic liquid.
【０００２】[0002]
【従来の技術】近年、高分子ゲル化剤のみならず、有機
性低分子ゲル化剤の研究も活発に行われるようになっ
た。しかしながら、高分子ゲル化剤に比較して、低分子
ゲル化剤の発明、発見が遅れていて、低分子ゲル化剤の
種類が少ない。2. Description of the Related Art In recent years, not only polymer gelling agents but also organic low molecular weight gelling agents have been actively studied. However, the invention and discovery of the low molecular weight gelling agent are delayed compared to the high molecular weight gelling agent, and there are few types of the low molecular weight gelling agent.
【０００３】これまでに知られている有機性低分子ゲル
化剤としては、ジベンザールソルビット及びそれらの芳
香核置換体、１２−ヒドロキシステアリン酸、アシル化
アミノ酸アマイド類、コレステロール誘導体等がある。Known organic low molecular weight gelling agents include dibenzal sorbit and aromatic nucleus substitution products thereof, 12-hydroxystearic acid, acylated amino acid amides, cholesterol derivatives and the like.
【０００４】従来のゲル化剤は、各々特徴を有してお
り、塗料やインキの流動調整剤や固形剤、流出油のゲル
化回収剤、農薬の固形化剤、目地止めのスランプ防止
剤、高分子加工助剤、芳香剤の固形化剤等、夫々のゲル
化剤の特性に応じて使用されている。The conventional gelling agents have their respective characteristics. They are flow regulators and solid agents for paints and inks, gelation and recovery agents for spilled oil, solidifying agents for agricultural chemicals, anti-slumping agents for sealing joints, It is used depending on the characteristics of the respective gelling agents such as polymer processing aids and fragrance solidifying agents.
【０００５】しかしながら、各々の分野で十分満足され
ているわけではなく、新しい機能と特徴を有したゲル化
剤の発見が期待されている。とりわけ、低融点であっ
て、比較的低温で溶解しやすく、かつ、安定なゲルを形
成する特徴を有するゲル化剤の誕生に期待の一つがあ
る。However, they are not sufficiently satisfied in each field, and the discovery of gelling agents having new functions and characteristics is expected. In particular, there is one expectation for the birth of a gelling agent which has a low melting point, is easily dissolved at a relatively low temperature, and is characterized by forming a stable gel.
【０００６】[0006]
【発明が解決しようとする課題】本発明は、特徴あるゲ
ル化機能を有する新しい有機性ゲル化剤を産業界に提供
し、もって、有機性ゲルの応用分野の発展に益すること
を目的とする。DISCLOSURE OF THE INVENTION It is an object of the present invention to provide a new organic gelling agent having a characteristic gelation function to the industrial world, and thereby to contribute to the development of the application field of organic gel. To do.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、新規有用
な有機性ゲル化剤を開発すべく鋭意検討の結果、特定の
構造を有するビスアマイド類が、それ自体は従来公知の
化合物ではあるが、所期の目的を達成し得るゲル化能を
有する化合物であることを新たに見いだし、かかる知見
に基づいて本発明を完成するに至った。Means for Solving the Problems As a result of intensive studies to develop a novel and useful organic gelling agent, the present inventors have found that bisamides having a specific structure are known compounds per se. However, the present invention was newly found to be a compound having gelling ability capable of achieving the intended purpose, and the present invention has been completed based on such findings.
【０００８】即ち、本発明に係る有機性ゲル化剤は、下
記一般式（１）で示されるビスアマイド類（以下「本ア
マイド類」と総称する。）を有効成分として含有するこ
とを特徴とする。That is, the organic gelling agent according to the present invention is characterized by containing the bisamides represented by the following general formula (1) (hereinafter collectively referred to as "the present amides") as an active ingredient. ..
【化２】 ［式中、Ｒ1、Ｒ2は、同一又は異なって、１２−ヒドロ
キシオクタデシル基又は１２−ヒドロキシオクタデセニ
ル基を表す。ｎは２〜１２の整数を示す。］[Chemical 2] [In the formula, R 1 and R 2 are the same or different and each represents a 12-hydroxyoctadecyl group or a 12-hydroxyoctadecenyl group. n shows the integer of 2-12. ]
【０００９】本アマイド類は、１２−ヒドロキシオクタ
デカン酸、１２−ヒドロキシオクタデセン酸又はそれら
のメチルエステルから選ばれる１種又は２種以上の化合
物と、目的とするビスアマイドに対応するジアミンとを
２５０℃以下で、無触媒下又は触媒の存在下にて縮合す
ることにより、ほぼ定量的に得ることができる。The amides include one or more compounds selected from 12-hydroxyoctadecanoic acid, 12-hydroxyoctadecenoic acid or their methyl esters, and a diamine corresponding to the desired bisamide at 250 ° C. In the following, it can be obtained almost quantitatively by condensation in the absence of a catalyst or in the presence of a catalyst.
【００１０】本アマイド類を得るために用いられるジア
ミンは、炭素数２〜１２のアルキレンジアミンであり、
特にエチレンジアミン、トリメチレンジアミン、テトラ
メチレンジアミン、ヘキサメチレンジアミン、ドデカン
メチレンジアミンが推奨される。The diamine used to obtain the amides is an alkylenediamine having 2 to 12 carbon atoms,
In particular, ethylenediamine, trimethylenediamine, tetramethylenediamine, hexamethylenediamine and dodecanemethylenediamine are recommended.
【００１１】本アマイド類を調製するに際し、必要に応
じて用いられる上記触媒としては、ナトリウムメチラー
ト等のアルカリアルコラート、苛性ソーダ、苛性カリ、
水酸化アルミニウム、アルキルチタネート、パラトルエ
ンスルホン酸、硫酸等が例示される。The above-mentioned catalysts, which are used as necessary when preparing the amides, include alkali alcoholates such as sodium methylate, caustic soda, caustic potash,
Examples include aluminum hydroxide, alkyl titanates, paratoluene sulfonic acid, sulfuric acid and the like.
【００１２】これらの本アマイド類は、いずれも融点が
１５０℃以下と低く、低温溶解性の良好なゲル化剤とし
ての特徴を有している。Each of these amides has a melting point as low as 150 ° C. or lower and is characterized as a gelling agent having good low temperature solubility.
【００１３】本アマイド類によりゲル化し得る対象物は
多岐に亘り、例えば、鉱油、廃食用油、アスファルト、
香料、医薬品基剤、目地止め剤、マーキング材、可塑
剤、エチレン−酢酸ビニル樹脂、グリース（潤滑油）等
の他、従来公知のゲル化剤、例えば１２−ヒドロキシス
テアリン酸やアシル化アミノ酸アマイド類ではゲル化で
きなかった高級アルコール類や脂肪酸類に対しても適用
可能である。There are a wide variety of objects which can be gelled by the amides, such as mineral oil, waste edible oil, asphalt,
In addition to perfumes, pharmaceutical bases, sealants, marking materials, plasticizers, ethylene-vinyl acetate resins, greases (lubricating oils), etc., conventionally known gelling agents such as 12-hydroxystearic acid and acylated amino acid amides. Can also be applied to higher alcohols and fatty acids that could not be gelled.
【００１４】本アマイド類をゲル化剤として適用する処
方の一例を以下に述べる。即ち、ゲル化対象物（ベース
の基剤）と本アマイド類（ゲル化剤）とを加熱下に混合
して均一溶液とした後、混合を停止し、冷却する。この
とき、所定の効果を奏する限り、従来公知の他のゲル化
剤を併用しても良い。An example of a formulation in which the amides are applied as a gelling agent will be described below. That is, the gelling target (base material) and the amides (gelling agent) are mixed under heating to form a uniform solution, and then the mixing is stopped and cooled. At this time, other conventionally known gelling agents may be used in combination as long as a predetermined effect is exhibited.
【００１５】上記物質をゲル化するに際して適用される
本アマイド類の量は、その対象物質の種類及び処理条件
等を勘案して適宜選択されるが、通常、ゲル化対象物に
対して０．０５〜３０重量％程度、好ましくは０．２〜
１０重量％程度である。The amount of the amides to be applied in gelling the above substance is appropriately selected in consideration of the type of the substance to be treated and the processing conditions. 05-30% by weight, preferably 0.2-
It is about 10% by weight.
【００１６】本アマイド類は、ゲル化剤としてのみなら
ず、結晶性高分子であるポリエチレン、ポリプロピレ
ン、ポリエチレンテレフタレ−ト、ポリブタジエン樹脂
等の結晶促進剤や剛性向上剤及び透明化向上剤としての
機能を有する核剤としても有効である。The amides are used not only as a gelling agent, but also as a crystal accelerator such as polyethylene, polypropylene, polyethylene terephthalate, polybutadiene resin which is a crystalline polymer, a rigidity improver and a transparency improver. It is also effective as a nucleating agent having a function.
【００１７】加えて、これら結晶性樹脂成形物の諸物性
を低下させずに高分子の溶融状態における成形性を向上
させる可塑剤としても有効である。In addition, it is also effective as a plasticizer for improving the moldability of the polymer in the molten state without deteriorating the physical properties of these crystalline resin molded products.
【００１８】[0018]
【実施例】以下に、実施例を掲げ、本発明を詳しく説明
する。尚、ゲル硬度は、以下の方法に従って測定した。
即ち、１００mlのビーカーを用い、ゲル化対象物に対し
て所定量のゲル化剤を配合し、加熱溶解・冷却して調製
したゲルを室温中に４時間放冷した後、厚み約１cmのゲ
ルを取り出し、このゲルに２００ｇ／cm2／分の速度で
荷重して、ゲルが急速に崩壊するときの荷重量からゲル
硬度を算出する。EXAMPLES The present invention will be described in detail below with reference to examples. The gel hardness was measured according to the following method.
That is, using a 100 ml beaker, a gelling agent was mixed with a predetermined amount of a gelling agent, heated and dissolved / cooled, and the gel was left to cool to room temperature for 4 hours. Then, the gel is loaded at a rate of 200 g / cm 2 / min, and the gel hardness is calculated from the load when the gel rapidly disintegrates.
【００１９】実施例１ トリデカノール１０ｇを試験管に採取し、エチレンビス
（１２−ヒドロキシオクタデカン酸）アマイド０．４ｇ
を加温溶解し、水冷して２分後の状態を観察した。その
結果、試験管を倒置してもトリデカノールの流下がな
く、系の流動性が明かに消失し、ゲルを形成していた。
このもののゲル硬度は８００ｇ／cm2であった。又、こ
のゲルは、昇温すると均一溶液となり、水冷により再び
熱可逆的にゲルを形成した。Example 1 10 g of tridecanol was placed in a test tube and 0.4 g of ethylenebis (12-hydroxyoctadecanoic acid) amide was added.
Was dissolved by heating, cooled with water, and the state after 2 minutes was observed. As a result, even when the test tube was inverted, tridecanol did not flow down, the fluidity of the system was clearly lost, and a gel was formed.
The gel hardness of this product was 800 g / cm 2 . Further, this gel became a uniform solution when the temperature was raised, and again formed a gel reversibly by cooling with water.
【００２０】実施例２ ゲル化対象物をアルキルベンゼンとした他は実施例１に
準じてゲル形成の有無を判定した。その結果、系の流動
性が明かに消失し、ゲルを形成していた。Example 2 The presence or absence of gel formation was determined according to Example 1 except that the gelling target was alkylbenzene. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２１】実施例３ ゲル化対象物を大豆油とした他は実施例１に準じてゲル
形成の有無を判定した。その結果、系の流動性が明かに
消失し、ゲルを形成していた。Example 3 The presence or absence of gel formation was determined according to Example 1 except that soybean oil was used as the gelling target. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２２】実施例４ ゲル化対象物をオレイン酸とした他は実施例１に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 4 The presence or absence of gel formation was determined according to Example 1 except that oleic acid was used as the gelation target. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２３】実施例５ ジオクチルフタレート１０ｇに対し、ゲル化剤として１
２−ヒドロキシオクタデカン酸系ビスアマイド（ｎ＝
２）０．５ｇを適用した他は、実施例１に準じてゲル形
成の有無を判定した。その結果、系の流動性が明かに消
失し、ゲルを形成していた。Example 5 10 g of dioctyl phthalate was added as a gelling agent to 1 g.
2-hydroxyoctadecanoic acid-based bisamide (n =
2) The presence or absence of gel formation was determined according to Example 1 except that 0.5 g was applied. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２４】実施例６ ゲル化剤として１２−ヒドロキシオクタデカン酸系ビス
アマイド（ｎ＝４）を適用した他は、実施例５に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 6 The presence or absence of gel formation was determined according to Example 5, except that 12-hydroxyoctadecanoic acid type bisamide (n = 4) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２５】実施例７ ゲル化剤として１２−ヒドロキシオクタデカン酸系ビス
アマイド（ｎ＝６）を適用した他は、実施例５に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 7 The presence or absence of gel formation was determined according to Example 5, except that 12-hydroxyoctadecanoic acid-based bisamide (n = 6) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２６】実施例８ ゲル化剤として１２−ヒドロキシオクタデカン酸系ビス
アマイド（ｎ＝８）を適用した他は、実施例５に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 8 The presence or absence of gel formation was determined according to Example 5, except that 12-hydroxyoctadecanoic acid type bisamide (n = 8) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２７】実施例９ ジオクチルフタレート１０ｇに対し、ゲル化剤として１
２−ヒドロキシオクタデセン酸系ビスアマイド（ｎ＝
２）０．５ｇを適用した他は、実施例１に準じてゲル形
成の有無を判定した。その結果、系の流動性が明かに消
失し、ゲルを形成していた。Example 9 10 g of dioctyl phthalate was added to 1 g of the gelling agent.
2-hydroxyoctadecenoic acid-based bisamide (n =
2) The presence or absence of gel formation was determined according to Example 1 except that 0.5 g was applied. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２８】実施例１０ ゲル化剤として１２−ヒドロキシオクタデセン酸系ビス
アマイド（ｎ＝４）を適用した他は、実施例９に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 10 The presence or absence of gel formation was determined according to Example 9 except that 12-hydroxyoctadecenoic acid-based bisamide (n = 4) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００２９】実施例１１ ゲル化剤として１２−ヒドロキシオクタデセン酸系ビス
アマイド（ｎ＝６）を適用した他は、実施例９に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 11 The presence or absence of gel formation was determined in the same manner as in Example 9 except that 12-hydroxyoctadecenoic acid type bisamide (n = 6) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００３０】実施例１２ ゲル化剤として１２−ヒドロキシオクタデセン酸系ビス
アマイド（ｎ＝８）を適用した他は、実施例９に準じて
ゲル形成の有無を判定した。その結果、系の流動性が明
かに消失し、ゲルを形成していた。Example 12 The presence or absence of gel formation was determined according to Example 9 except that 12-hydroxyoctadecenoic acid type bisamide (n = 8) was used as the gelling agent. As a result, the fluidity of the system clearly disappeared and a gel was formed.
【００３１】[0031]
【発明の効果】本発明に係る有機性ゲル化剤は、比較的
低温で溶解してゲルを形成する。このため、ゲル形成新
素材として産業界に提供され、ゲルの新しい応用分野の
発展に寄与することができる。The organic gelling agent according to the present invention dissolves at a relatively low temperature to form a gel. Therefore, it can be provided to the industry as a new gel-forming material and contribute to the development of new application fields of gel.
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【手続補正書】[Procedure amendment]
【提出日】平成４年８月２６日[Submission date] August 26, 1992
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１０[Correction target item name] 0010
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１０】 本アマイド類を得るために用いられるジ
アミンは、炭素数２〜１２のアルキレンジアミンであ
り、特にエチレンジアミン、トリメチレンジアミン、テ
トラメチレンジアミン、ヘキサメチレンジアミン、ドデ
カメチレンジアミンが推奨される。[0010] Diamines used to obtain the amides are alkylenediamines having 2 to 12 carbon atoms, in particular ethylene diamine, trimethylene diamine, tetramethylene diamine, hexamethylene diamine, dodecane
Camethylenediamine is recommended.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１３[Correction target item name] 0013
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【００１３】 本アマイド類によりゲル化し得る対象物
は多岐に亘り、例えば、鉱油、廃食用油、アスファル
ト、香料、医薬品基剤、目地止め剤、マーキング材、可
塑剤、エチレン−酢酸ビニル樹脂、グリース（潤滑
油）、接着剤、塗料、流出油等の他、従来公知のゲル化
剤、例えば１２−ヒドロキシステアリン酸やアシル化ア
ミノ酸アマイド類ではゲル化できなかった高級アルコー
ル類や脂肪酸類に対しても適用可能である。There are a wide variety of objects that can be gelled by the present amides, and examples thereof include mineral oil, waste edible oil, asphalt, fragrances, pharmaceutical bases, joint inhibitors, marking materials, plasticizers, ethylene-vinyl acetate resins, greases. (Lubricant oil) , adhesives, paints, spilled oil, etc., as well as higher alcohols and fatty acids which cannot be gelled by conventionally known gelling agents such as 12-hydroxystearic acid and acylated amino acid amides. Is also applicable.
───────────────────────────────────────────────────── 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 Ｃ０９Ｄ 11/00 ＰＴＧ 7415−4Ｊ Ｃ０９Ｋ 3/32 8318−4Ｈ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification number Office reference number FI technical display location C09D 11/00 PTG 7415-4J C09K 3/32 8318-4H
Claims (1)
を有効成分とすることを特徴とする有機性ゲル化剤。 【化１】 ［式中、Ｒ1、Ｒ2は、同一又は異なって、１２−ヒドロ
キシオクタデシル基又は１２−ヒドロキシオクタデセニ
ル基を表す。ｎは２〜１２の整数を示す。］1. An organic gelling agent, which comprises a bisamide compound represented by the general formula (1) as an active ingredient. [Chemical 1] [In the formula, R 1 and R 2 are the same or different and each represents a 12-hydroxyoctadecyl group or a 12-hydroxyoctadecenyl group. n shows the integer of 2-12. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15594392A JPH05320617A (en) | 1992-05-21 | 1992-05-21 | New organic gelling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15594392A JPH05320617A (en) | 1992-05-21 | 1992-05-21 | New organic gelling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05320617A true JPH05320617A (en) | 1993-12-03 |
Family
ID=15616916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15594392A Pending JPH05320617A (en) | 1992-05-21 | 1992-05-21 | New organic gelling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05320617A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0848965A (en) * | 1994-08-03 | 1996-02-20 | Nisshin Oil Mills Ltd:The | Gelling or solidifying agent for organic liquid |
| JPH0873826A (en) * | 1994-09-01 | 1996-03-19 | Mitsui Toatsu Chem Inc | Hot-melt adhesive composition |
| US5688440A (en) * | 1995-10-26 | 1997-11-18 | Baylor University | Organic gellation agents |
| JP2010516851A (en) * | 2007-01-23 | 2010-05-20 | トータル・ラフィナージュ・マーケティング | Bituminous composition having thermoreversible properties |
| WO2017170388A1 (en) * | 2016-03-31 | 2017-10-05 | 株式会社大阪ソーダ | Photocurable resin composition, ink and coating material |
| JP2019506516A (en) * | 2016-02-26 | 2019-03-07 | ザ プロクター アンド ギャンブル カンパニー | Thickened or structured liquid detergent composition |
| WO2019068914A1 (en) * | 2017-10-05 | 2019-04-11 | Rhodia Operations | Formulations comprising surfactants, organic liquids and viscosifiers |
| WO2019068913A1 (en) * | 2017-10-05 | 2019-04-11 | Rhodia Operations | Formulations comprising biologically active ingredients |
-
1992
- 1992-05-21 JP JP15594392A patent/JPH05320617A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0848965A (en) * | 1994-08-03 | 1996-02-20 | Nisshin Oil Mills Ltd:The | Gelling or solidifying agent for organic liquid |
| JPH0873826A (en) * | 1994-09-01 | 1996-03-19 | Mitsui Toatsu Chem Inc | Hot-melt adhesive composition |
| US5688440A (en) * | 1995-10-26 | 1997-11-18 | Baylor University | Organic gellation agents |
| US5876631A (en) * | 1995-10-26 | 1999-03-02 | Baylor University | Fluorinated organic gelation agents |
| JP2010516851A (en) * | 2007-01-23 | 2010-05-20 | トータル・ラフィナージュ・マーケティング | Bituminous composition having thermoreversible properties |
| JP2019506516A (en) * | 2016-02-26 | 2019-03-07 | ザ プロクター アンド ギャンブル カンパニー | Thickened or structured liquid detergent composition |
| JP2020189987A (en) * | 2016-02-26 | 2020-11-26 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | Thickened or structured liquid detergent compositions |
| CN108699314A (en) * | 2016-03-31 | 2018-10-23 | 株式会社大阪曹达 | Photocurable resin composition, ink and coating |
| JPWO2017170388A1 (en) * | 2016-03-31 | 2019-02-07 | 株式会社大阪ソーダ | Photo-curable resin composition, ink and paint |
| WO2017170388A1 (en) * | 2016-03-31 | 2017-10-05 | 株式会社大阪ソーダ | Photocurable resin composition, ink and coating material |
| US10941232B2 (en) | 2016-03-31 | 2021-03-09 | Osaka Soda Co., Ltd. | Photocurable resin composition, ink and coating material |
| WO2019068914A1 (en) * | 2017-10-05 | 2019-04-11 | Rhodia Operations | Formulations comprising surfactants, organic liquids and viscosifiers |
| WO2019068913A1 (en) * | 2017-10-05 | 2019-04-11 | Rhodia Operations | Formulations comprising biologically active ingredients |
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