JP4267308B2 - Surfactant additive - Google Patents
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- JP4267308B2 JP4267308B2 JP2002349488A JP2002349488A JP4267308B2 JP 4267308 B2 JP4267308 B2 JP 4267308B2 JP 2002349488 A JP2002349488 A JP 2002349488A JP 2002349488 A JP2002349488 A JP 2002349488A JP 4267308 B2 JP4267308 B2 JP 4267308B2
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Description
【０００１】
【発明の属する技術分野】
本発明は、優れた洗浄性能、乳化性能を実現でき、更に低温下でのハンドリング性に優れる界面活性剤用添加剤に関する。
【０００２】
【従来の技術】
シャンプー、リンス、固形石けん、ボディシャンプー、台所用洗剤、衣料用洗剤、住居用洗剤等の洗浄剤には、最も重要な基本性能である「高い洗浄性能」に加えて、使用時の豊かな「泡立ち」が要求される。従来、こうした洗浄剤製品における主基剤として広く使用されているのは、アルキルベンゼンスルホン酸塩、アルキル硫酸エステル塩、ポリオキシエチレンアルキル硫酸エステル塩等の陰イオン界面活性剤であるが、これらはいずれも多量の油分やシリコンが存在する系では、泡立ちの低下だけに留まらず、著しい洗浄力や乳化力の低下が起こり、洗浄剤としての満足の行く性能を発現できない。
【０００３】
こうした、陰イオン界面活性剤の欠点である油分に対する弱さを克服するために、非イオン界面活性剤を使用するのが常套手段である。広く使用されている非イオン界面活性剤には、ポリオキシアルキレンアルキルエーテル、アルキルポリグルコシド等が挙げられる。
【０００４】
しかし、これらの非イオン界面活性剤をもってしても、その乳化力、洗浄力は十分とは言えず、特に油の存在下においてはその傾向が著しい。このことから、汎用性の界面活性剤の洗浄性能、乳化性能の一層の向上を簡便に実現できる界面活性剤用添加剤が望まれてきた。
【０００５】
このような界面活性剤用添加剤として、ジエタノール脂肪酸アミドが実際に広く製品中に使用されてきた。また、モノエタノール脂肪酸アミド（特許文献１、特許文献２、特許文献３等）等も提案されている。しかしながら、このような添加剤を添加しても、洗浄力、起泡性が改良されるものの未だ十分に満足できるものではない。
【０００６】
また、特許文献４には、Ｎ−エタノール−Ｎ−メチル脂肪酸アミドを含有する界面活性剤組成物が開示されているが、このＮ−エタノール−Ｎ−メチル脂肪酸アミドや、ジアルカノール脂肪酸アミドは、２０℃以下で急激な粘度上昇が起こり、ハンドリング性に問題があった。
【０００７】
【特許文献１】
国際公開第９８／５０７号パンフレット
【特許文献２】
国際公開第９７／４４４３４号パンフレット
【特許文献３】
特開平１１−８０７８５号公報
【特許文献４】
特開２００１−２２０５９７号公報
【０００８】
【発明が解決しようとする課題】
本発明の課題は、優れた洗浄性能、乳化性能を実現でき、更に２０℃以下の低温下でのハンドリング性に優れる界面活性剤用添加剤を提供することにある。
【０００９】
【課題を解決するための手段】
本発明は、一般式（Ｉ）で表される化合物（以下化合物（Ｉ）という）からなる界面活性剤用添加剤、並びに化合物（Ｉ）と、界面活性剤の少なくとも１種とを含有する界面活性剤組成物を提供する。
【００１０】
【化２】
（式中、R1CO−は炭素数６〜２４の水酸基を有していてもよい飽和又は不飽和のアシル基、R2は炭素数１〜３の直鎖又は分岐鎖のアルキル基、R3は炭素数１〜３の直鎖又は分岐鎖のアルキル基を示す。）
【００１２】
【発明の実施の形態】
本発明に用いられる化合物（Ｉ）において、R1CO−は上記のようなアシル基を示すが、炭素数８〜１８の飽和又は不飽和アシル基が好ましい。具体的にはオクタン酸、デカン酸、ドデカン酸、テトラデカン酸、ヘキサデカン酸、オクタデカン酸、ドコサン酸、リノール酸、２−エチルヘキサン酸、２−オクチルウンデカン酸、イソステアリン酸、オレイン酸、ヤシ脂肪酸、パーム核油脂肪酸、パーム油脂肪酸、牛脂脂肪酸等から誘導されるアシル基が挙げられ、特に好ましくは、オクタン酸、デカン酸、ドデカン酸、テトラデカン酸、ヘキサデカン酸、オクタデカン酸、オレイン酸、ヤシ脂肪酸、パーム油脂肪酸、パーム核油脂肪酸、牛脂脂肪酸から誘導されるアシル基である。これらのアシル基の中でも、炭素数１２〜１４の脂肪酸から誘導されるアシル基が５０重量％以上含まれたものが好ましく、また、炭素数１２の脂肪酸から誘導されるアシル基が４０重量％以上、１００重量％未満のものがより好ましい。
【００１３】
また、R2は炭素数１〜３の直鎖又は分岐鎖のアルキル基であり、好ましくはメチル基、エチル基、特に好ましくはメチル基である。
【００１４】
さらに、R3は炭素数１〜３の直鎖又は分岐鎖のアルキル基であり、好ましくはメチル基、エチル基、特に好ましくはメチル基である。
【００１５】
化合物（Ｉ）の具体例として、例えば、Ｎ−イソプロパノール−Ｎ−メチルオクタン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルデカン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルドデカン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルテトラデカン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルヘキサデカン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルオクタデカン酸アミド、Ｎ−イソプロパノール−Ｎ−メチルヤシ脂肪酸アミド、Ｎ−イソプロパノール−Ｎ−メチルパーム核油脂肪酸アミド、Ｎ−イソプロパノール−Ｎ−エチルイソステアリン酸アミド等が挙げられる。
【００１６】
化合物（Ｉ）の製造法は、特に限定されず、例えば、脂肪酸又は脂肪酸低級アルコールエステルとアルカノールアミンとの脱水又は脱アルコール反応、脂肪酸ハロゲン化物とアルカノールアミンのアルカリ触媒下での反応、あるいは油脂とアルカノールアミンとのエステル−アミド交換反応等を用いて製造することができる。これらの方法で得られた製造物中に、脂肪酸、無機塩、グリセリン等が少量含まれることがあるが、それらは性能には何ら差し支えない。
【００１７】
本発明において、界面活性剤は、特に限定されず、陰イオン界面活性剤、非イオン界面活性剤、陽イオン界面活性剤、両性界面活性剤から選ばれる少なくとも１種を適宜用いることができる。好ましい界面活性剤としては、アルキル硫酸塩、ポリオキシエチレンアルキル硫酸塩等の硫酸塩型界面活性剤；アルキルベンゼンスルホン酸塩等のスルホン酸塩型界面活性剤；アルキルリン酸エステル塩等のリン酸エステル塩型界面活性剤；アシル化アミノ酸塩、アルキルエーテルカルボン酸塩、石鹸等の他の陰イオン界面活性剤；アルキルポリグルコシド等の非イオン界面活性剤；アルキルジメチルアミンオキサイド、アミドプロピルジメチルアミンオキサイド等のアミンオキサイド型界面活性剤；アミドプロピルジメチルカルボベタイン等のカルボベタイン型界面活性剤が挙げられ、特に好ましい界面活性剤としては、アルキル硫酸塩、ポリオキシエチレンアルキル硫酸塩等の硫酸塩型界面活性剤、アルキルベンゼンスルホン酸塩等のスルホン酸塩型界面活性剤、アルキルリン酸エステル塩等のリン酸エステル塩型界面活性剤；アルキルジメチルアミンオキサイド、アミドプロピルジメチルアミンオキサイド等のアミンオキサイド型界面活性剤、アミドプロピルジメチルカルボベタイン等のカルボベタイン型界面活性剤が挙げられる。
【００１８】
本発明の界面活性剤組成物中の化合物（Ｉ）と界面活性剤との配合割合は、洗浄性能、乳化性能の観点から、重量比で１／９９〜９９／１が好ましく、１／９９〜８０／２０がより好ましく、１／９９〜５０／５０が特に好ましい。
【００１９】
また、本発明の界面活性剤組成物中の化合物（Ｉ）と界面活性剤の合計含有量は、良好な界面活性能を得る観点から、５．０〜１００重量％が好ましく、１０〜１００重量％が更に好ましい。
【００２０】
また、本発明の界面活性剤組成物は、ｐＨの領域に左右されることなく、その特性を遺憾なく発揮することができるが、特にｐＨ領域３．０〜１１．０で好ましい洗浄性能、起泡性能が得られる。更に、２０℃以下の低温下でも急激な粘度上昇が起こらず、ハンドリング性に優れ、洗浄性能、起泡性能の低温下での安定性にも優れている。
【００２１】
【実施例】
例中の％は、特記しない限り重量％である。
【００２２】
実施例１〜４及び比較例１〜４
下記に示す化合物を用い、表１に示す組成の各種界面活性剤組成物を調製し、下記方法により洗浄性能及び乳化能を評価した。結果を表１に示す。
なお、実施例２及び４は参考例である。
【００２３】
＜化合物（Ｉ）＞
化合物１：Ｎ−イソプロパノール−Ｎ−メチルパーム核油脂肪酸アミド
化合物２：Ｎ−イソプロパノール−Ｎ−メチルドデカン酸アミド
＜比較化合物＞
比較化合物１：ジエタノールパーム核油脂肪酸アミド
＜界面活性剤＞
界面活性剤１：ポリオキシエチレン（４）ラウリルエーテル硫酸ナトリウム塩
界面活性剤２：ドデシル硫酸エステルナトリウム塩
界面活性剤３：モノラウリルリン酸エステルナトリウム塩
＜洗浄性能評価法＞
(1) 人工汚染布の調製
下記組成の人工汚染液を布に付着させて人工汚染布を調製した。人工汚染液の布への付着は、グラビアロールコーターを用いて行った。人工汚染液を布に付着させ人工汚染布を作成する工程は、グラビアロールのセル容量５８cm3／m2、塗布速度１．０ｍ／min、乾燥温度１００℃、乾燥時間１分間で行った。布は木綿金巾２００３布（谷頭商店製）を使用した。
【００２４】
・人工汚染液の組成
ラウリン酸 ０．４４％
ミリスチン酸 ３．０９％
ペンタデカン酸 ２．３１％
パルミチン酸 ６．１８％
ヘプタデカン酸 ０．４４％
ステアリン酸 １．５７％
オレイン酸 ７．７５％
トリオレイン １３．０６％
パルミチン酸ｎ−ヘキサデシル ２．１８％
スクアレン ６．５３％
卵白レシチン液晶物 １．９４％
鹿沼赤土 ８．１１％
カーボンブラック ０．０１％
水道水 バランス
(2) 洗浄条件及び評価法
評価用界面活性剤組成物の水溶液１リットルに、上記で作成した１０ｃｍ×１０ｃｍの人工汚染布を５枚入れ、ターゴトメーターにて１００ｒ／minで洗浄した。洗浄条件は次の通りである。
【００２５】
・洗浄条件
洗浄時間：１０分
界面活性剤組成物濃度：０．０５％
炭酸ソーダ濃度：０．００８％
水の硬度：２°DH
水温：２０℃
すすぎ：水道水にて５分間
洗浄力は汚染前の原布及び洗浄前後の汚染布の５５０ｎｍにおける反射率を自記色彩計（島津製作所製）にて測定し、次式によって洗浄率（％）を求め、５枚の測定平均値を洗浄力として示した。
【００２６】
洗浄率（％）＝（洗浄後の反射率−洗浄前の反射率）／（原布の反射率−洗浄前の反射率）×１００
＜乳化能評価法＞
界面活性剤組成物をイオン交換水で希釈し、０．５％の水溶液を調製し、これらの水溶液を内径３ｃｍの３００ｍｌ活栓付きメスシリンダーに５０ｍｌ入れ、さらに静かに菜種油を５０ｍｌ入れた後、２５℃、１０秒間、振幅１５ｃｍで２０回振とうした。３０分静置した後の、乳化相の体積（ｍｌ）を測定した。
【００２７】
【表１】
実施例５
下記に示す本発明化合物１及び比較化合物１及び２を用い、下記条件で粘度を測定した。結果を表２に示す。
本発明化合物１：Ｎ−イソプロパノール−Ｎ−メチルパーム核油脂肪酸アミド
比較化合物１：ジエタノールパーム核油脂肪酸アミド
比較化合物２：Ｎ−エタノール−Ｎ−メチルパーム核油脂肪酸アミド
＜粘度測定条件＞
各化合物を、２０℃において、Ｂ型粘度計（東京計器（株）製）を用いて測定した。
【００２９】
【表２】
表２の結果から、本発明の化合物は、２０℃以下でも流動性に優れ、冬季のポンプ移送等も容易であることがわかる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an additive for a surfactant that can realize excellent cleaning performance and emulsification performance and is excellent in handling properties at low temperatures.
[0002]
[Prior art]
For detergents such as shampoos, rinses, solid soaps, body shampoos, kitchen detergents, clothing detergents, and residential detergents, in addition to the most important basic performance, “high cleaning performance”, "Bubbling" is required. Conventionally, anionic surfactants such as alkylbenzene sulfonates, alkyl sulfates, and polyoxyethylene alkyl sulfates have been widely used as main bases in such detergent products. However, in a system in which a large amount of oil or silicon is present, not only the reduction of foaming but also a significant reduction in detergency and emulsifying ability occurs, and satisfactory performance as a detergent cannot be expressed.
[0003]
In order to overcome the weakness against oil, which is a drawback of anionic surfactants, it is a common practice to use nonionic surfactants. Nonionic surfactants that are widely used include polyoxyalkylene alkyl ethers, alkyl polyglucosides, and the like.
[0004]
However, even with these nonionic surfactants, the emulsifying power and detergency cannot be said to be sufficient, and the tendency is particularly remarkable in the presence of oil. For this reason, there has been a demand for an additive for surfactants that can easily realize further improvement in washing performance and emulsification performance of general-purpose surfactants.
[0005]
As such a surfactant additive, diethanol fatty acid amide has actually been widely used in products. In addition, monoethanol fatty acid amides (Patent Document 1, Patent Document 2, Patent Document 3, etc.) have been proposed. However, even if such an additive is added, although the detergency and foamability are improved, it is still not fully satisfactory.
[0006]
Patent Document 4 discloses a surfactant composition containing N-ethanol-N-methyl fatty acid amide. This N-ethanol-N-methyl fatty acid amide, dialkanol fatty acid amide, A sudden increase in viscosity occurred at 20 ° C. or lower, and there was a problem in handling properties.
[0007]
[Patent Document 1]
International Publication No. 98/507 Pamphlet [Patent Document 2]
International Publication No. 97/44434 Pamphlet [Patent Document 3]
Japanese Patent Laid-Open No. 11-80785 [Patent Document 4]
Japanese Patent Laid-Open No. 2001-220597
[Problems to be solved by the invention]
The subject of this invention is providing the additive for surfactants which can implement | achieve the outstanding washing | cleaning performance and emulsification performance, and is excellent in handling property in 20 degrees C or less low temperature.
[0009]
[Means for Solving the Problems]
The present invention relates to a surfactant additive comprising a compound represented by general formula (I) (hereinafter referred to as compound (I)), and an interface containing compound (I) and at least one surfactant. An activator composition is provided.
[0010]
[Chemical formula 2]
(In the formula, R 1 CO— is a saturated or unsaturated acyl group optionally having a hydroxyl group having 6 to 24 carbon atoms, R 2 is a linear or branched alkyl group having 1 to 3 carbon atoms, R 3 represents a linear or branched alkyl group having 1 to 3 carbon atoms.)
[0012]
DETAILED DESCRIPTION OF THE INVENTION
In the compound (I) used in the present invention, R 1 CO— represents an acyl group as described above, and a saturated or unsaturated acyl group having 8 to 18 carbon atoms is preferable. Specifically, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, docosanoic acid, linoleic acid, 2-ethylhexanoic acid, 2-octylundecanoic acid, isostearic acid, oleic acid, coconut fatty acid, palm Examples include acyl groups derived from nuclear oil fatty acids, palm oil fatty acids, beef tallow fatty acids, and the like, particularly preferably octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, oleic acid, coconut fatty acid, palm It is an acyl group derived from oil fatty acid, palm kernel oil fatty acid, and beef tallow fatty acid. Among these acyl groups, those containing 50% by weight or more of an acyl group derived from a fatty acid having 12 to 14 carbon atoms are preferred, and more than 40% by weight of the acyl group derived from a fatty acid having 12 carbon atoms. More preferred is less than 100% by weight.
[0013]
R 2 is a linear or branched alkyl group having 1 to 3 carbon atoms, preferably a methyl group, an ethyl group, and particularly preferably a methyl group.
[0014]
Further, R 3 is a linear or branched alkyl group having 1 to 3 carbon atoms, preferably a methyl group, an ethyl group, particularly preferably a methyl group.
[0015]
Specific examples of compound (I) include, for example, N-isopropanol-N-methyloctanoic acid amide, N-isopropanol-N-methyldecanoic acid amide, N-isopropanol-N-methyldodecanoic acid amide, N-isopropanol-N-methyl. Tetradecanoic acid amide, N-isopropanol-N-methylhexadecanoic acid amide, N-isopropanol-N-methyloctadecanoic acid amide, N-isopropanol-N-methyl coconut fatty acid amide, N-isopropanol-N-methyl palm kernel fatty acid amide, N -Isopropanol-N-ethyl isostearic acid amide etc. are mentioned.
[0016]
The production method of compound (I) is not particularly limited. For example, dehydration or dealcoholization reaction of fatty acid or fatty acid lower alcohol ester and alkanolamine, reaction of fatty acid halide and alkanolamine under an alkali catalyst, or oil and fat It can be produced using an ester-amide exchange reaction with an alkanolamine. The products obtained by these methods may contain a small amount of fatty acid, inorganic salt, glycerin and the like, but they do not interfere with performance.
[0017]
In the present invention, the surfactant is not particularly limited, and at least one selected from an anionic surfactant, a nonionic surfactant, a cationic surfactant, and an amphoteric surfactant can be appropriately used. Preferred surfactants include sulfate-type surfactants such as alkyl sulfates and polyoxyethylene alkyl sulfates; sulfonate-type surfactants such as alkylbenzene sulfonates; phosphate esters such as alkyl phosphate ester salts Salt type surfactants; Other anionic surfactants such as acylated amino acid salts, alkyl ether carboxylates and soaps; Nonionic surfactants such as alkylpolyglucosides; Alkyldimethylamine oxide, Amidopropyldimethylamine oxide, etc. Amine oxide type surfactants; carbobetaine type surfactants such as amidopropyldimethylcarbobetaine and the like. Particularly preferred surfactants include sulfate type surfactants such as alkyl sulfates and polyoxyethylene alkyl sulfates. Agent, alkylbenzene sulfonate, etc. Phosphonate type surfactants such as phonate type surfactants, alkyl phosphate ester salts; amine oxide type surfactants such as alkyldimethylamine oxide and amidopropyldimethylamine oxide, and amidopropyldimethylcarbobetaine Examples include carbobetaine type surfactants.
[0018]
The blending ratio of the compound (I) and the surfactant in the surfactant composition of the present invention is preferably 1/99 to 99/1 in terms of weight ratio from the viewpoint of washing performance and emulsification performance, 80/20 is more preferable, and 1/99 to 50/50 is particularly preferable.
[0019]
In addition, the total content of the compound (I) and the surfactant in the surfactant composition of the present invention is preferably 5.0 to 100% by weight, preferably 10 to 100% from the viewpoint of obtaining good surface activity. % Is more preferable.
[0020]
In addition, the surfactant composition of the present invention can exert its characteristics without being affected by the pH range, but it is particularly preferable in the pH range of 3.0 to 11.0. Foam performance is obtained. Furthermore, the viscosity does not increase suddenly even at a low temperature of 20 ° C. or lower, the handling property is excellent, and the stability of the washing performance and foaming performance at a low temperature is also excellent.
[0021]
【Example】
In the examples, “%” means “% by weight” unless otherwise specified.
[0022]
Examples 1-4 and Comparative Examples 1-4
Using the compounds shown below, various surfactant compositions having the compositions shown in Table 1 were prepared, and the washing performance and emulsifying ability were evaluated by the following methods. The results are shown in Table 1.
Examples 2 and 4 are reference examples.
[0023]
<Compound (I)>
Compound 1: N-isopropanol-N-methyl palm kernel oil fatty acid amide compound 2: N-isopropanol-N-methyldodecanoic acid amide <Comparative compound>
Comparative compound 1: Diethanol palm kernel oil fatty acid amide <Surfactant>
Surfactant 1: Polyoxyethylene (4) sodium lauryl ether sulfate surfactant 2: Dodecyl sulfate sodium salt surfactant 3: Monolauryl phosphate sodium salt <Detergent performance evaluation method>
(1) Preparation of artificially contaminated cloth An artificially contaminated cloth having the following composition was attached to the cloth to prepare an artificially contaminated cloth. The artificial contamination liquid was attached to the cloth using a gravure roll coater. The process of making an artificially contaminated cloth by attaching an artificially contaminated liquid to the cloth was carried out with a gravure roll cell capacity of 58 cm 3 / m 2 , a coating speed of 1.0 m / min, a drying temperature of 100 ° C., and a drying time of 1 minute. As the cloth, a cotton gold cloth 2003 cloth (manufactured by Tanigami Shoten) was used.
[0024]
-Composition of artificial contamination liquid Lauric acid 0.44%
Myristic acid 3.09%
Pentadecanoic acid 2.31%
Palmitic acid 6.18%
Heptadecanoic acid 0.44%
Stearic acid 1.57%
Oleic acid 7.75%
Trio Rain 13.06%
N-Hexadecyl palmitate 2.18%
Squalene 6.53%
Egg white lecithin liquid crystal 1.94%
Kanuma red soil 8.11%
Carbon black 0.01%
Tap water balance
(2) Washing conditions and evaluation method Five 10 cm x 10 cm artificially contaminated fabrics prepared above were placed in 1 liter of an aqueous solution of a surfactant composition for evaluation, and washed with a tartometer at 100 r / min. The cleaning conditions are as follows.
[0025]
・ Cleaning conditions Cleaning time: 10 minutes Surfactant composition concentration: 0.05%
Sodium carbonate concentration: 0.008%
Water hardness: 2 ° DH
Water temperature: 20 ° C
Rinse: The cleaning power with tap water is 5 minutes. The reflectance at 550 nm of the original cloth before and after contamination is measured with a self-recording color meter (manufactured by Shimadzu Corporation). The five measured average values were shown as detergency.
[0026]
Washing rate (%) = (reflectance after washing−reflectance before washing) / (reflectance of raw fabric−reflectivity before washing) × 100
<Emulsifying ability evaluation method>
The surfactant composition was diluted with ion-exchanged water to prepare 0.5% aqueous solutions, 50 ml of these aqueous solutions were placed in a 300 ml stopcock measuring cylinder with an inner diameter of 3 cm, and 50 ml of rapeseed oil was gently put into 25 ml. The mixture was shaken 20 times with an amplitude of 15 cm at 10 ° C. for 10 seconds. The volume (ml) of the emulsified phase after standing for 30 minutes was measured.
[0027]
[Table 1]
Example 5
Using the present compound 1 and comparative compounds 1 and 2 shown below, the viscosity was measured under the following conditions. The results are shown in Table 2.
The present compound 1: N-isopropanol-N-methyl palm kernel oil fatty acid amide comparison compound 1: Diethanol palm kernel oil fatty acid amide comparison compound 2: N-ethanol-N-methyl palm kernel oil fatty acid amide <Viscosity measurement conditions>
Each compound was measured at 20 ° C. using a B-type viscometer (manufactured by Tokyo Keiki Co., Ltd.).
[0029]
[Table 2]
From the results in Table 2, it can be seen that the compound of the present invention is excellent in fluidity even at 20 ° C. or lower, and is easily pumped in winter.
Claims (1)
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