JPS6187657A - Preparation of alpha-sulfo-fatty acid ester salt - Google Patents

Preparation of alpha-sulfo-fatty acid ester salt

Info

Publication number
JPS6187657A
JPS6187657A JP59209293A JP20929384A JPS6187657A JP S6187657 A JPS6187657 A JP S6187657A JP 59209293 A JP59209293 A JP 59209293A JP 20929384 A JP20929384 A JP 20929384A JP S6187657 A JPS6187657 A JP S6187657A
Authority
JP
Japan
Prior art keywords
fatty acid
acid ester
sulfo
sulfo fatty
alpha
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
JP59209293A
Other languages
Japanese (ja)
Other versions
JPH045666B2 (en
Inventor
Takashi Imamura
孝 今村
Tomokatsu Kusumi
智勝 楠見
Yoshimasa Sasa
佐々　嘉正
Tomihiro Kurosaki
黒崎　富裕
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.)
Kao Corp
Original Assignee
Kao Corp
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 Kao Corp filed Critical Kao Corp
Priority to JP59209293A priority Critical patent/JPS6187657A/en
Priority to PH32830A priority patent/PH21117A/en
Priority to ES547355A priority patent/ES8609227A1/en
Priority to DE19853535184 priority patent/DE3535184A1/en
Priority to FR8514763A priority patent/FR2571368A1/en
Publication of JPS6187657A publication Critical patent/JPS6187657A/en
Publication of JPH045666B2 publication Critical patent/JPH045666B2/ja
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE:To prepare the titled compound useful as a detergent and resistant to the lowering of the ester-content with time, with little hydrolysis of the product, easily, by mixing and neutralizing a liquid alpha-sulfo-fatty acid ester with powdery solid carbonate and/or bicarbonate. CONSTITUTION:A liquid alpha-sulfo-fatty acid ester is mixed and neutralized with (A) a powdery solid carbonate and/or (B) bicarbonate to obtain an alpha-sulfo-fatty acid ester salt. The amount of the component A and/or B is 1-150mol, preferably 4-60mol per 1mol of the alpha-sulfo-fatty acid ester. The component A or B is e.g. Na2CO3, K2CO3, NaHCO3, etc. A detergent composition having high hydrolysis resistance and cleaning property can be prepared by mixing the alpha-sulfo-fatty acid ester salt produced by the present process with other detergent components (e.g. spray-dried powder).

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明はα−スルホ脂肪酸エステル塩の製造法に関する
。更に詳しくは、エステル保持率が高く且つそのエステ
ル保持基が洗剤配合、保存時においても殆んど低下のし
ない固体状α−スルホ脂肪酸エステル塩を簡便且つ省資
源的に製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing an α-sulfo fatty acid ester salt. More specifically, the present invention relates to a simple and resource-saving method for producing a solid α-sulfo fatty acid ester salt which has a high ester retention rate and whose ester retention group hardly decreases even when added to detergents and stored.

〔従来の技術及びその問題点〕[Conventional technology and its problems]

従来よりα−スルホ脂肪酸エステル塩は粉末洗剤用界面
活性剤として特徴ある性能を有しているが、反面、耐加
水分解性に乏しい事は公知の通りである。即ち脂肪酸エ
ステルのスルホン化物はアルカリ水溶液による中和工程
及び洗剤スラリー化、噴霧乾錬工程によって加水分解を
引き起こし、更に噴霧乾燥品についても経口的に加水分
解が進行する。Although α-sulfo fatty acid ester salts have traditionally had distinctive performance as surfactants for powder detergents, it is well known that they have poor hydrolysis resistance. That is, sulfonated fatty acid esters undergo hydrolysis through a neutralization step with an aqueous alkali solution, detergent slurry formation, and spray drying steps, and furthermore, hydrolysis proceeds orally in spray-dried products.

その結果、α−スルホ脂肪酸塩が副生ずるが、α−スル
ホ脂肪酸塩は界面活性能が貧弱であシ、α−スルホ脂肪
酸エステル塩中に多量に含まれる事は好ましくない。As a result, α-sulfo fatty acid salt is produced as a by-product, but since α-sulfo fatty acid salt has poor surface activity, it is not preferable for it to be contained in a large amount in the α-sulfo fatty acid ester salt.

加水分解を防止する為、特定のアルカリ性ビルグーの使
用（特開昭５２−２８５０７）、ヒンダードフェノール
系化合物とヒドロキシカルボン酸塩の併用（特公昭５ｓ
−２８１６３）が提案されているが、充分効果のあるも
のではない０ 又、噴霧乾燥工程でα−スルホ脂肪酸エステル塩のスラ
リーと強アルカリ成分を含有するスラリーを同−転線空
間内に同時に噴霧し、加水分解を防止する方法も提案さ
れている（特開昭５８−４ｙ０９ａ）。しかし、この方
法とて操作が繁雑であり、省資源的でなく、また経日安
定性も必ずしも満足ゆくものではない。In order to prevent hydrolysis, the use of a specific alkaline virgoo (Japanese Patent Publication No. 52-28507), the combination of hindered phenol compounds and hydroxycarboxylic acid salts (Japanese Patent Publication No. 52-28507),
-28163) has been proposed, but it is not sufficiently effective.Also, in the spray drying process, a slurry of α-sulfo fatty acid ester salt and a slurry containing a strong alkaline component are simultaneously sprayed into the space of the same line. However, a method for preventing hydrolysis has also been proposed (Japanese Unexamined Patent Publication No. 58-4-09a). However, this method requires complicated operations, is not resource-saving, and its stability over time is not necessarily satisfactory.

このような状況下において、下記の式で示されるエステ
ル保持率が高く、シかも経日的に加水分解しない固体粉
末状のα−スルホ脂肪酸エステル塩を簡便且つ省資源的
に製造する方法の開発が望まれていた。Under these circumstances, we developed a simple and resource-saving method for producing a solid powdered α-sulfo fatty acid ester salt, which has a high ester retention rate and does not hydrolyze over time, as shown by the formula below. was desired.

（（Ｍ〕：モル濃度を示す） 〔問題点を解決するための手段〕 本発明者らは上記の如き問題点を解決する為、鋭意研究
を重ねた結果、液状＼のα−スルホ脂肪酸エステルを固
体粉末状の炭酸塩及び／又は炭酸水素塩と共に混合・中
和する仁とにょシ。((M): indicates molar concentration) [Means for solving the problem] In order to solve the above-mentioned problems, the present inventors have conducted extensive research and have developed a liquid α-sulfo fatty acid ester. Mix and neutralize with solid powdered carbonate and/or bicarbonate.

中和直後のエステル保持率が高く、シかも経日的にも加
水分解されにくい固体状のα−スルホ脂肪酸エステル塩
が得られることを見い出し。It has been discovered that a solid α-sulfo fatty acid ester salt can be obtained that has a high ester retention rate immediately after neutralization and is resistant to hydrolysis over time.

本発明を完成させた。The present invention has been completed.

アルキルベンゼンスルホン酸については、このようなド
ライ中和の技術は既に知られていたが、α−スルホ脂肪
酸エステルをドライ中和することは全くなされていなか
った。これは、α−スルホ脂肪酸エステルについては加
水分解が最大の問題であシ、α−スルホ脂肪酸エステル
を直接アルカリで中和するドライ中和では加水分解が避
けられないと考えていた為である。Although such dry neutralization techniques for alkylbenzenesulfonic acids have already been known, dry neutralization of α-sulfo fatty acid esters has never been attempted. This was because it was believed that hydrolysis was the biggest problem with α-sulfofatty acid esters, and that hydrolysis was unavoidable in dry neutralization in which α-sulfofatty acid esters were directly neutralized with alkali.

しかし１本発明者らがα−スルホ脂肪酸エステルを直接
固体粉末状の炭酸塩及び／又は炭酸水素塩と共に比較的
短時間内に混合・中和すれば意外にも加水分解は殆んど
起らず、更に驚くべきことＫはエステル保持率が経日的
にも殆んど低下しないことを見い出し本発明を完成した
ものである。また本発明の方法は、簡便であることは勿
論、近年要求が高まっている省資源の点でも極めて優れ
た方法である。However, if the present inventors directly mixed and neutralized α-sulfo fatty acid ester with solid powdered carbonate and/or bicarbonate within a relatively short period of time, surprisingly little hydrolysis occurred. More surprisingly, K has completed the present invention by discovering that the ester retention rate hardly decreases over time. Furthermore, the method of the present invention is not only simple but also extremely excellent in terms of resource saving, which has been in increasing demand in recent years.

本発明に係るα−スルホ脂肪酸エステルとしては下記一
般式（１）で表わされる化合物が挙げられる。Examples of the α-sulfo fatty acid ester according to the present invention include compounds represented by the following general formula (1).

（式（１）中、Ｒ工は炭素数８〜２４好ましくは１０〜
２０の直鎖又は分枝鎖アルキル基を表わし、Ｒ２は炭素
数１〜６好ましくは１〜３の直鎖又は分枝鎖アルキル基
を表わす。） とのα−スルホ脂肪酸エステルは脂肪酸エステルを公知
の方法１例えば８０．ガスでスルホン化する方法により
容易に得られる。使用される脂肪酸エステルとは一般式
　　　　　ＯＲ１０Ｈ２００Ｒ２ （式中、Ｒ１，Ｒ２は前記のとおシ）で表わされる化合
物である。この脂肪酸エステルは牛脂。(In formula (1), R has 8 to 24 carbon atoms, preferably 10 to 24 carbon atoms.
20 straight-chain or branched-chain alkyl groups, and R2 represents a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms. ) The α-sulfo fatty acid ester can be prepared by preparing the fatty acid ester using a known method 1, e.g. 80. It is easily obtained by sulfonation with gas. The fatty acid ester used is a compound represented by the general formula OR10H200R2 (wherein R1 and R2 are as defined above). This fatty acid ester is beef tallow.

豚脂、骨油、魚油、ラノリン等の動物系油脂や、ヤシ油
、パーム油、パーム核油、大豆油等の植物系油脂などか
ら誘導される。It is derived from animal fats and oils such as lard, bone oil, fish oil, and lanolin, and vegetable fats and oils such as coconut oil, palm oil, palm kernel oil, and soybean oil.

例えばカプリン酸、ラウリン酸、ミリスチン酸、パルミ
チン酸、ステアリン酸、アラキン酸、ベヘニン酸。For example, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid.

リグノセリン酸、セロチン酸、インデカン酸、ネオデカ
ン酸、クンデセンｒＪ：１、インドリデカン酸、インバ
ルミチン酸、イソステアリン酸、硬化牛脂脂肪酸、ヤシ
油脂肪酸、パーム油脂肪酸、パーム核油脂肪酸、硬化魚
油脂肪酸等のメチル、エチル、プロピル、イソプロピル
、ブチル、イソブチル、　ＢｅＣ−ブチル、ｔｅｒｔ−
ブチル、ペンチル、インペンチル、ネオペンチル、ｔｅ
ｒｔ−ペンチル、ヘキシル、インヘキシル等のエステル
が挙げられる。Methyl lignoceric acid, cerotic acid, indecanoic acid, neodecanoic acid, Kundecene rJ:1, indoridecanoic acid, invalmitic acid, isostearic acid, hydrogenated beef tallow fatty acid, coconut oil fatty acid, palm oil fatty acid, palm kernel oil fatty acid, hydrogenated fish oil fatty acid, etc. , ethyl, propyl, isopropyl, butyl, isobutyl, BeC-butyl, tert-
Butyl, pentyl, impentyl, neopentyl, te
Examples include esters such as rt-pentyl, hexyl, inhexyl and the like.

脂肪酸エステルのヨウ素価（ＩＶ）は１以下である事が
好ましい。The iodine value (IV) of the fatty acid ester is preferably 1 or less.

本発明の実施にあたって、α−スルホ脂肪酸ＸＸチルと
共にその他のスルポン酸、硫酸エステルを混合して中和
に用いることもできる。その他のスルホン酸、硫酸エス
テルとしては例えハ、アルキルベンゼンスルホン酸、α
−スルホ脂肪酸、アルキル硫酸エステル、アルキルポリ
オキシエチレン硫酸エステル等が挙げられる。In carrying out the present invention, other sulfonic acids and sulfuric esters may be mixed with α-sulfo fatty acid XX til and used for neutralization. Examples of other sulfonic acids and sulfuric esters include
-Sulfo fatty acids, alkyl sulfate esters, alkyl polyoxyethylene sulfate esters, and the like.

本発明に使用される中和剤である炭酸塩及び／又は炭酸
水素塩としては、例えば炭酸塩として炭Ｍアルカリ金属
塩、炭酸アルカリ土類金属塩。Examples of the carbonate and/or hydrogen carbonate as a neutralizing agent used in the present invention include charcoal alkali metal salts and alkaline earth metal carbonates.

炭酸アンモニクム塩、炭酸アルカノールアミン塩等が、
又、炭酸水素塩として炭酸水素アルカリ金属塩、炭酸水
素アルカリ土類金属塩、炭酸水素７７モニクム塩、炭酸
水素アルカノールアミン塩等が挙げられる。好ましくは
炭酸す）　ＩＪウム、炭酸カリウム、炭酸アンモニクム
、炭酸水素ナトリウム、炭酸水素カリ９ム、炭酸水素ア
ンそニウムであシ、無水塩もしくは水利塩又はそれらの
混合物であってもよい。Ammonicum carbonate salt, alkanolamine carbonate salt, etc.
Examples of the hydrogen carbonate include alkali metal hydrogen carbonate salts, alkaline earth metal hydrogen carbonate salts, 77monicum hydrogen carbonate salts, and alkanolamine hydrogen carbonate salts. (preferably carbonate), potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, anhydrous salts or aqueous salts, or mixtures thereof.

使用される炭酸塩及び／又は炭酸水素塩の使用量はα−
スルホ脂肪酸エステル１モルに対して１〜１５０モルで
ちゃ、好ましくは４〜６０モルである。１モル未満であ
ると反応性に乏しく反応に長時間を要し、又中和物も固
い塊状の固形分となり粉砕による粒状化が困難となる。The amount of carbonate and/or bicarbonate used is α-
The amount is 1 to 150 mol, preferably 4 to 60 mol, per 1 mol of sulfo fatty acid ester. If it is less than 1 mole, the reactivity is poor and the reaction takes a long time, and the neutralized product also becomes a solid lump, making it difficult to granulate it by pulverization.

又１５０モルを越えると反応に対する効果は変わらない
が、α−スルホ脂肪酸エステル塩に対する炭酸塩、炭酸
水素塩の量が極めて多くなシ、他の洗剤成分を配合し洗
剤組成物とする際、洗浄性能上問題が生じる。If the amount exceeds 150 moles, the effect on the reaction will not change, but the amount of carbonate or hydrogen carbonate relative to the α-sulfo fatty acid ester salt is extremely large, and when combining other detergent ingredients to form a detergent composition, it may be difficult to clean. This will cause performance problems.

液状のα−スルホ脂肪酸エステルと固体粉末状の炭酸塩
及び／又は炭酸水素塩との混合・中和は強い攪拌下に行
なうのが好ましく、α−スルホ脂肪酸エステル゛と炭酸
塩及び／又は炭酸水素塩の割合が１７３０〜１／１（モ
ル比）の範囲では強剪断カ下に混合・中和することが望
ましい。It is preferable to mix and neutralize liquid α-sulfo fatty acid ester and solid powder carbonate and/or hydrogen carbonate under strong stirring. When the proportion of salt is in the range of 1730 to 1/1 (molar ratio), it is desirable to mix and neutralize under strong shearing force.

本発明の実施にあたシ１本発明の効果を害しない範囲で
α−スルホ脂肪酸エステルと炭酸塩及び／又は炭酸水素
塩以外の他の成分を加えることも可能である。これら他
の成分としては。In carrying out the present invention, it is also possible to add other components other than α-sulfo fatty acid ester and carbonate and/or hydrogen carbonate within a range that does not impair the effects of the present invention. As for these other ingredients.

水、水酸化ナトリクム水溶液、ケイ酸ナトリヮム又はそ
の水溶液、カルボキシル基及び（又は）ヒドロキシル基
を含む高分子量の有機重合体及びその水溶液、非イオン
界面活性剤、泡末安定剤、漂白剤、ゼオライト、リン酸
塩、硫酸ナトリウム、ポリアルキレンクリコール又はそ
の水溶液、香料、螢光染料、顔料、酵素、紫外線吸収剤
等洗剤成分として有効に作用しうるものが挙けられる。Water, sodium hydroxide aqueous solution, sodium silicate or its aqueous solution, high molecular weight organic polymer containing carboxyl group and/or hydroxyl group and its aqueous solution, nonionic surfactant, foam powder stabilizer, bleach, zeolite, Examples include phosphates, sodium sulfate, polyalkylene glycols or aqueous solutions thereof, fragrances, fluorescent dyes, pigments, enzymes, ultraviolet absorbers, and other substances that can effectively act as detergent ingredients.

これらのその他の成分中にはこれらを添加する事によシ
中和後の中和物の粉砕が容易になる成分又は中和反応を
促進させる効果のある成分も含まれている。These other components also include components that facilitate the pulverization of the neutralized product after neutralization or components that have the effect of promoting the neutralization reaction.

中和後の中和物の粉砕を容易とさせる成分としては、例
えばゼオライト、リン酸塩、硫酸ナトリウム等が挙げら
れる。Examples of components that facilitate the pulverization of the neutralized product after neutralization include zeolite, phosphate, sodium sulfate, and the like.

又、中和反応を促進させる効果のある成分としては、例
えば水、少量の水酸化す）　ＩＪクム及びケイ酸す）　
ＩＪウム水溶液が挙げられる。中和反応の際、加えられ
る水はα−スルホ脂肪酸エステル１モルに対して１〜６
０モルが好ましい。In addition, examples of components that have the effect of promoting the neutralization reaction include water, a small amount of hydroxide, IJ cum, and silicic acid.
IJum aqueous solution is mentioned. During the neutralization reaction, the amount of water added is 1 to 6 per mole of α-sulfo fatty acid ester.
0 mol is preferred.

１モル未満の水は、中和の促進効果が小さく。If the amount of water is less than 1 mol, the effect of promoting neutralization is small.

一方６０モル以上の水は中和物がペースト状となり粉砕
できないか、又はα−スルホ脂肪酸塩の加水分解を引き
起ζす等の問題が生じる。中和反応の際、加えられる水
のα−スルホ脂肪酸エステルに対するモル数とは単体で
加えられる水の他、その他の成分中に含まれる水をも合
わせた値である。On the other hand, if the amount of water is 60 moles or more, the neutralized product will become paste-like and cannot be crushed, or problems will occur, such as causing hydrolysis of the α-sulfo fatty acid salt. During the neutralization reaction, the number of moles of water added to the α-sulfo fatty acid ester is a value that includes water added alone as well as water contained in other components.

本発明に於て中和反応に用いられる装置は。The apparatus used for the neutralization reaction in the present invention is as follows.

混線様のような強力剪断装置であり、連続式、回分式い
ずれも用いる事ができる。例えば連続式トしてはホンダ
・コンティニュアスニーダ−（本田鉄工（株）　）　、
マルチパーパスコンティニニアスミキサ−（ＢＡＫＩＩ
：ＲＰＫＲＫ工ＮＳ　［０，）　、ＫＲＯニーダ−（栗
本鉄工（株））、ネスコニーダー（富士産業（株））等
が挙げられる。上述の混線機は、いずれも未中和物と炭
酸塩、炭酸水素塩との接触機会を増すような機構を有し
ており、連続でセルフクリーニング機構をもつという特
徴がある。It is a strong shearing device similar to a cross-wire type, and can be used in both continuous and batch types. For example, the Honda Continuous Kneader (Honda Iron Works Co., Ltd.) is a continuous kneader.
Multi-purpose continuous mixer (BAKII
: RPKRK NS [0,), KRO kneader (Kurimoto Iron Works Co., Ltd.), Nesco kneader (Fuji Sangyo Co., Ltd.), and the like. All of the above-mentioned crosstalk machines have a mechanism that increases the chance of contact between unneutralized substances, carbonates, and hydrogen carbonates, and are characterized by having a continuous self-cleaning mechanism.

これらの装置内での滞留時間は、条件にもよるが通常、
約５〜１０分位で十分である。The residence time in these devices depends on the conditions, but is usually
Approximately 5 to 10 minutes is sufficient.

中和時の温度は３０〜９０℃であシ、好ましくは４０〜
７０℃である。The temperature during neutralization is 30 to 90°C, preferably 40 to 90°C.
The temperature is 70°C.

冷却した中和物は粒状又は塊状の固形物である。この中
和物を単独もしくは芒硝やゼオライト尋の洗剤配合物と
混合し粉砕する。通常１，５００μ以下、望ましくは８
００μ以下に粉砕する。The cooled neutralized product is a granular or lumpy solid. This neutralized product is ground either alone or mixed with a detergent formulation of Glauber's salt or zeolite fat. Usually 1,500μ or less, preferably 8
Grind to 00μ or less.

本発明で得られたα−スルホ脂肪酸エステル塩と他の洗
剤成分を混合すると耐加水分解性、洗浄性能が良好な洗
剤組成物が得られる。他の洗剤成分は別途噴霧乾燥して
得られた粉末品であってよい。他の洗剤成分としては、
各種界面活性剤、ビルグー、各種添加剤が挙げられる。When the α-sulfo fatty acid ester salt obtained in the present invention is mixed with other detergent components, a detergent composition with good hydrolysis resistance and cleaning performance can be obtained. Other detergent ingredients may be powder products obtained by separate spray drying. Other detergent ingredients include
Examples include various surfactants, virgoos, and various additives.

界面活性剤としては各種の陰イオン性界面活性剤、非イ
オン性界面活性剤１両性界面活性剤を単独又は組合せて
用いることができる。次にかかる界面活性剤の好ましい
例を示す。As the surfactant, various anionic surfactants, nonionic surfactants, amphoteric surfactants can be used alone or in combination. Preferred examples of such surfactants are shown below.

（１）陰イオン性界面活性剤 ・平均炭素数１０〜１６のアルキル基を有すル直鎖又は
分岐鎖アルキルベンゼンスルホン酸塩 ・平均炭素数８〜２０の直鎖又は分岐鎖のアルキル基又
はアルクニル基を有し、１分子内に平均０．５〜８モル
のエチレンオキサイドを付加したアルキル又はアルケニ
ルエトキシ硫酸塩又はリンは塩 ・平均炭素ｆｉｌｏ乃至２０のアルキル基又はアルケニ
ル基を有するアルキル又はアルケニル硫酸塩又はリン酸
塩 ・平均１０〜２０の炭素原子を１分子中に有するオレフ
ィンスルホン酸塩 ・平均１０〜２０の炭素原子を１分子中に有するアルカ
ンスルホ７ｒｌｌ塩 ・平均１０〜２ｏの炭素原子を１分子中に有する飽和又
は不飽和脂肪酸塩 ・平均炭素数１ｏ〜２ｏのアルキル基又はアルケニル基
を有し、１分子中に平均０．５〜８モルのエチレンオキ
サイドを付加したアルキル又はアルケニルエトキシカル
ボン酸塩 （１１）非イオン性界面活性剤 ・平均炭素数８〜２ｏの１級又は２級のアルキル基又は
アルケニル基を有し、３〜１２モルのエチレンオキサイ
ドを付加したポリオキシエチレンアルキル又はアルクニ
ルエーテル ・平均炭素数８〜１２のアルキル基を有し、３〜１２モ
ルのエチレンオキサイドラ付加したポリオキシエチレン
アルキルフェニルエーテル ・下記の式で表わされる高級脂肪酸アルカノールアミド
又はそのアルキレンオキサイド付加物 （ＩＩＯ両性界面活性剤 ・下記の式で表わされるアルキルアミンオキサイド Ｒ，　−　Ｎ→０ （式中Ｒ，は炭素数１０〜２０のアルキル基又はアルケ
ニル基であシ、Ｒ６，　Ｒ７は炭素数１〜３のアルキル
基であり、同−又は異なっても良い） ・下記の式で表わされるアルキルベタイン又はスルホベ
タイン ＲＱ （式中Ｒ８は炭素数１０〜２０のアルキル基又はアルケ
ニル基を表わし、Ｒ９１ＲｌＧは炭素数１〜４のアルキ
ル基、ｐは１〜３ｅ ）整数、Ｘは−ｃｏｏ　　又は−ｓｏ、　　基を表わす
） 各種ピルグーとしては、ゼオライト、オルソリン酸塩、
トリポリリン酸塩、ピロリン酸塩、メタリン酸塩等の縮
合リン酸塩、ニトリロ三酢酸塩、エチレンジアミン四酢
酸塩、ジエチレントリアミン五酢酸塩等のアミノポリ酢
酸、クエン酸塩、リンゴ酸塩、グリコール酸塩等のオキ
シカルボン酸塩、ポリアクリル酸、酢酸ビニル−無水マ
レイン酸共重合物のアルカリ加水分解塩等の高分子電解
質などが挙げられる。(1) Anionic surfactant - Straight chain or branched alkylbenzene sulfonate having an alkyl group with an average carbon number of 10 to 16 - Straight chain or branched alkyl group or alkyl group having an average carbon number of 8 to 20 Alkyl or alkenyl ethoxy sulfate or phosphorus is a salt having an average of 0.5 to 8 moles of ethylene oxide added to each molecule.Alkyl or alkenyl sulfate having an alkyl or alkenyl group with an average carbon filo to 20 Salt or phosphate - Olefin sulfonate having an average of 10 to 20 carbon atoms in one molecule - Alkane sulfonate salt having an average of 10 to 20 carbon atoms in one molecule - An average of 10 to 2 carbon atoms Saturated or unsaturated fatty acid salt in one molecule - Alkyl or alkenyl ethoxy carbon having an alkyl group or alkenyl group with an average carbon number of 1 to 2 o, and an average of 0.5 to 8 moles of ethylene oxide added to each molecule Acid acid salt (11) Nonionic surfactant - Polyoxyethylene alkyl or alkyl having a primary or secondary alkyl group or alkenyl group with an average carbon number of 8 to 2 o and to which 3 to 12 moles of ethylene oxide are added. Polyoxyethylene alkylphenyl ether having an alkyl group with an average carbon number of 8 to 12 and added with 3 to 12 moles of ethylene oxide.Higher fatty acid alkanolamide represented by the following formula or its alkylene oxide adduct ( IIO amphoteric surfactant - Alkylamine oxide represented by the following formula R, - N→0 (wherein R is an alkyl group or alkenyl group having 10 to 20 carbon atoms, R6 and R7 are carbon atoms 1 to 20) 3, which may be the same or different) - Alkylbetaine or sulfobetaine RQ represented by the following formula (in the formula, R8 represents an alkyl group or alkenyl group having 10 to 20 carbon atoms, and R91RlG represents a carbon alkyl group of numbers 1 to 4; p is an integer;
Condensed phosphates such as tripolyphosphate, pyrophosphate, metaphosphate, aminopolyacetic acid such as nitrilotriacetate, ethylenediaminetetraacetate, diethylenetriaminepentaacetate, citrate, malate, glycolate, etc. Examples include polymer electrolytes such as oxycarboxylic acid salts, polyacrylic acid, and alkali hydrolyzed salts of vinyl acetate-maleic anhydride copolymers.

更にアルカリ剤あるいは無機電解質としてケイ酸ナトリ
クム、硫酸ナトリウムなど、また再汚染防止剤としてポ
リエチレングリコール、ポリビニルアルコール、ポリビ
ニルピロリドン、カルボキシメチルセルロースなどを配
合しうる。Furthermore, sodium silicate, sodium sulfate, etc. may be added as an alkaline agent or inorganic electrolyte, and polyethylene glycol, polyvinyl alcohol, polyvinylpyrrolidone, carboxymethyl cellulose, etc. may be added as a re-staining prevention agent.

更に、過炭酸ソーダ等の漂白剤、螢光増白剤。In addition, bleaching agents such as soda percarbonate, and fluorescent whitening agents.

香料、色素、酵素、青味付剤、織物軟化剤、泡コントロ
ール剤等の添加剤も配合しつる〇〔発明の効果〕 本発明の方法によシ得られたα−スルホ脂肪酸エステル
塩は中和直後のエステル保持率が高く、３５℃の恒温室
内にて防湿カートン容器で保存しても経口的な加水分解
はほとんど認められな−いか、あったとしてもわずかで
ある。Additives such as fragrances, pigments, enzymes, bluing agents, fabric softeners, foam control agents, etc. can also be blended. [Effects of the Invention] The ester retention rate is high immediately after addition, and even when stored in a moisture-proof carton container in a thermostatic chamber at 35° C., oral hydrolysis is hardly observed or, if at all, minimal.

又、本発明の方法により得られたα−スルホ脂肪酸エス
テル塩を含有した洗剤組成物を３５℃の恒温室内にで防
湿カートン容器で保存してもα−スルホ脂肪酸エステル
塩の経口的な加水分解はほとんど認められないかあった
としてもわずかであシ、洗浄性能の低下は認められない
。Furthermore, even if the detergent composition containing the α-sulfo fatty acid ester salt obtained by the method of the present invention is stored in a thermostatic chamber at 35° C. in a moisture-proof carton container, the oral hydrolysis of the α-sulfo fatty acid ester salt will not occur. Almost no or only a small amount was observed, and no deterioration in cleaning performance was observed.

〔実施例〕〔Example〕

以下、実施例を示し、本発明を更に詳述する〇製造例１
（α−スルホ脂肪酸エステルの製造）硬化牛脂脂肪酸メ
チルを薄膜型スルホン化装置でＳＯ，モル比１．２、反
応温度５０〜６０℃で反応した。このスルホン化物を直
ちにサイクロンへ導入して気液分離を行った後、熱交換
器に通し１００℃３０分間熟成した。このスルホン化物
を５５℃まで冷却後、メタノールをスルホン化物に対し
５重量％加え、６０℃３０分間熟成した（これをα−ス
ルホ脂脂肪酸エステル色称す）。Examples are shown below to further explain the present invention in detail. Production Example 1
(Production of α-sulfo fatty acid ester) Hardened beef tallow fatty acid methyl was reacted with SO in a thin film type sulfonation apparatus at a molar ratio of 1.2 and a reaction temperature of 50 to 60°C. This sulfonated product was immediately introduced into a cyclone for gas-liquid separation, and then passed through a heat exchanger and aged at 100°C for 30 minutes. After cooling the sulfonated product to 55°C, 5% by weight of methanol was added to the sulfonated product, and the product was aged at 60°C for 30 minutes (this is referred to as α-sulfofatty acid ester color).

実施例１ 製造例１で得られたα−スルホ脂脂肪酸エステル色よび
表１に示す成分を定量供給し、栗本ＫＲＯニーグーで混
合、中和した。滞留時間は５〜７分間であり、中和時の
温度は４０〜６５℃であった。中和終了後、中和物を粉
砕し粒状物とした。Example 1 The α-sulfofatty acid ester color obtained in Production Example 1 and the components shown in Table 1 were supplied in quantitative amounts, mixed and neutralized using a Kurimoto KRO Nigu. The residence time was 5-7 minutes, and the temperature during neutralization was 40-65°C. After the neutralization was completed, the neutralized product was ground into granules.

粒状物のエステル保持率は表１の通シであった。The ester retention rate of the granules was as shown in Table 1.

更に得られた粒状物を防湿カートン容器に入れ３５℃、
５０℃の恒温室にて保存した。１ケ月後および３ケ月後
のエステル保持率は表２の通シであった。Furthermore, the obtained granules were placed in a moisture-proof carton container at 35°C.
It was stored in a constant temperature room at 50°C. The ester retention rates after one month and after three months were as shown in Table 2.

いずれの試料のエステル保持率も、下記比較例１試料Ｘ
（α−スルホ脂肪酸エステルＡ　全２．５％ＮａＯＨ水
落液で中和したもの；スルホン化率９７．５％、エステ
ル保持率９５．６％）とほぼ一致する。The ester retention rates of all samples are as follows: Comparative Example 1 Sample X
(α-sulfofatty acid ester A, neutralized with a total of 2.5% NaOH water; sulfonation rate 97.5%, ester retention rate 95.6%).

表　　　２ いずれの試料の加水分解も下記比較例２と比べはるかに
小さい事がわかる。Table 2 It can be seen that the hydrolysis of all samples is much smaller than that of Comparative Example 2 below.

実施例２ 実施例１で得られた試料Ｆ及びＧと、予め他の配′合成
分スラリーを噴霧乾燥して得られた粉末と混合し、下記
に示す洗剤組成物２−１及び２−２を調製した。この洗
剤組成物を防湿カートン容器に入れ、−５℃、４０℃、
５０℃の恒温室にて保存し、１ケ月後及び３ケ月後のエ
ステル保持率を測定した。結果を表３に示す。Example 2 Samples F and G obtained in Example 1 were mixed with powder obtained by spray-drying other formulation component slurries in advance to form detergent compositions 2-1 and 2-2 shown below. was prepared. This detergent composition was placed in a moisture-proof carton container, -5°C, 40°C,
It was stored in a constant temperature room at 50°C, and the ester retention rate was measured after one month and after three months. The results are shown in Table 3.

配　　　　合　　　物　　　２−１２−２試　　　料　
　　Ｆ　　　１５　　重量％　　−重量％試　　　料　
　　Ｇ　　　−１５ ドデシルベンゼン ユヤホ７僚ソーダ　１０　　　　　１゜ゼ　　　オ　　
　　ラ　　　　イ　　　　ト　　２０　　　　　　　　
　２０炭　　酸　　ソ　　−　　ダ　　−２７重炭酸ソ
ーダ２７．５５　　− 水　　　　　　　　　　　　分　　５５珪　　酸　　ソ
　　−　　ダ　　５５ 配　　　合　　　物　　　２−１２−２重量％　　　　
重量％ 芒　　　　　　　　　　　　硝　１７．３５　　　　１
８．７螢　　　光　　　染　　　料　　０．３　　　　
　　０．４表　　　　３ 比較例１ 製造例１で得られたα−スルホ脂肪酸エステルＡを用い
て中和物Ｋ、洗剤スラ１７−１　、噴霧乾燥品Ｍを調製
した。Mixture 2-12-2 sample
F15 wt% - wt% sample
G-15 Dodecylbenzene Yuyaho 7 members soda 10 1゜zeo
light 20
20 Sodium carbonate -27 Sodium bicarbonate 27.55 - Moisture 55 Sodium silicate 55 Compound 2-12-2% by weight
Weight% mirabilite 17.35 1
8.7 Firefly light dye 0.3
0.4 Table 3 Comparative Example 1 Neutralized product K, detergent slurry 17-1, and spray-dried product M were prepared using α-sulfo fatty acid ester A obtained in Production Example 1.

・中和物に α−スルホ脂肪酸エステルＡ　ヲ２．５％Ｈａ　Ｏｉｌ
水溶畝で中和した。・α-sulfo fatty acid ester A 2.5% Ha Oil for neutralization
Neutralized with a water-soluble ridge.

・洗剤スラ１７−　Ｌ　（固形分４５ｗｔ％、水分５７
ｗｔ％） °固形分組成 Ｎａ　２　ｓ　ｏｘ　　　　　　　　　　　２５・噴霧
乾燥品Ｍ 洗剤スラ１７　　Ｌを向流式噴霧転線装置を用いて噴霧
乾燥した。・Detergent slurry 17-L (solid content 45wt%, moisture 57
wt%) Solid content composition Na 2 s ox 25 Spray-dried product M Detergent slurry 17 L was spray-dried using a countercurrent spray transfer line device.

上記３種のエステル保持率を測定した０結果を表４に示
す。Table 4 shows the results of measuring the retention rates of the three types of esters mentioned above.

洗剤スラリー化、噴霧転線によジエステル保持率が大幅
に低下し大事がわかる０ 比較例２ 比較例１の噴霧乾燥品Ｍを一５℃、４０℃。The diester retention rate was significantly reduced due to detergent slurry formation and spray transition, which shows the importance.0 Comparative Example 2 The spray-dried product M of Comparative Example 1 was heated to -5°C and 40°C.

５０℃の恒温室にて防湿カートン容器で保存し。Store in a moisture-proof carton container in a constant temperature room at 50°C.

エステル保持率を測定した。結果を表５に示す。Ester retention was measured. The results are shown in Table 5.

表　　　　５ ４０〜５０℃では加水分解を引き起こし、はぼα−スル
ホ脂肪酸塩となり、洗浄性能も著しく低下し、実際上こ
の方法は工業的に実施困難なことがわかる。Table 5 At 40 to 50°C, hydrolysis occurs, resulting in the formation of α-sulfo fatty acid salts, and the cleaning performance is significantly reduced, indicating that this method is practically difficult to implement industrially.

出願人代理人　　古　　谷　　　　　馨手続ネＩロ正書
（自発） 昭和５９年１１月１６日 １、事件の表示 特願昭５９−２０９２９３号 ２．５１明の名称 α−スルホ脂肪酸エステル塩の製造法 ３、補正をする者 事件との関係　　特許出願人 （０９１）花王石鹸株式会社 ４、代理人 明細書の発明の詳細な説明の欄 ８、補正の内容 （１）明細書２１頁１２行の「試料Ｆ」を「α−゛（１
）　　同２１頁１３行目の「試料Ｇ」を［α−スルホ脂
肋酸エステルｌｕ　（試料Ｇ中）」と、ｉｆ止する。Applicant's agent: Kaoru Furuya Proposed proceedings (self-proposal) November 16, 1980 1, Indication of the case Patent Application No. 1983-209293 2.51 Name of Ming Method for producing α-sulfo fatty acid ester salts 3. Relationship with the case of the person making the amendment Patent applicant (091) Kao Soap Co., Ltd. 4, Column 8 of the detailed explanation of the invention in the agent's specification, Contents of the amendment (1) "On page 21, line 12 of the specification" sample F” to “α−゛(1
) "Sample G" on page 21, line 13 is defined as [α-sulfolipid costate lu (in sample G)].

（１）　　同２３頁３行目の［中和物に」を［中和１勿
に中のα−スルホ脂肪酸エステル塩」に訂正する。(1) In the third line of page 23, "in neutralized product" is corrected to "α-sulfo fatty acid ester salt in neutralized product".

Claims (1)

【特許請求の範囲】 １　液状のα−スルホ脂肪酸エステルを固体粉末状の炭
酸塩及び／又は炭酸水素塩と共に混合・中和することを
特徴とするα−スルホ脂肪酸エステル塩の製造法。 ２　炭酸塩及び／又は炭酸水素塩の使用量が、α−スル
ホ脂肪酸エステル１モルに対し１〜１５０モルである特
許請求の範囲第１項記載のα−スルホ脂肪酸エステル塩
の製造法。 ３　炭酸塩又は炭酸水素塩が炭酸ナトリウム又は炭酸水
素ナトリウムである特許請求の範囲第１項記載のα−ス
ルホ脂肪酸エステル塩の製造法。 ４　液状のα−スルホ脂肪酸エステルを固体粉末状の炭
酸塩及び／又は炭酸水素塩と共に混合・中和して得られ
るα−スルホ脂肪酸エステル塩と、別途噴霧乾燥して得
られる洗剤成分粉末を混合することを特徴とする洗剤の
製造方法。[Scope of Claims] 1. A method for producing an α-sulfo fatty acid ester salt, which comprises mixing and neutralizing a liquid α-sulfo fatty acid ester with a solid powdered carbonate and/or hydrogen carbonate. 2. The method for producing an α-sulfo fatty acid ester salt according to claim 1, wherein the amount of carbonate and/or hydrogen carbonate used is 1 to 150 mol per 1 mol of the α-sulfo fatty acid ester. 3. The method for producing an α-sulfo fatty acid ester salt according to claim 1, wherein the carbonate or hydrogen carbonate is sodium carbonate or sodium hydrogen carbonate. 4. Mixing α-sulfo fatty acid ester salt obtained by mixing and neutralizing liquid α-sulfo fatty acid ester with solid powder carbonate and/or hydrogen carbonate, and detergent component powder obtained by separate spray drying. A method for producing a detergent, characterized by:
JP59209293A 1984-10-05 1984-10-05 Preparation of alpha-sulfo-fatty acid ester salt Granted JPS6187657A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP59209293A JPS6187657A (en) 1984-10-05 1984-10-05 Preparation of alpha-sulfo-fatty acid ester salt
PH32830A PH21117A (en) 1984-10-05 1985-09-24 Process for the preparation of salts of o(-sulfo acid esters
ES547355A ES8609227A1 (en) 1984-10-05 1985-09-26 Preparation of alpha-sulfo-fatty acid ester salt
DE19853535184 DE3535184A1 (en) 1984-10-05 1985-10-02 Process for the preparation of salts of alpha -sulfofatty acid esters
FR8514763A FR2571368A1 (en) 1984-10-05 1985-10-04 Prepn. of hydrolysis-resistant salt of alpha-sulpho-fatty acid ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP59209293A JPS6187657A (en) 1984-10-05 1984-10-05 Preparation of alpha-sulfo-fatty acid ester salt

Publications (2)

Publication Number Publication Date
JPS6187657A true JPS6187657A (en) 1986-05-06
JPH045666B2 JPH045666B2 (en) 1992-02-03

Family

ID=16570540

Family Applications (1)

Application Number Title Priority Date Filing Date
JP59209293A Granted JPS6187657A (en) 1984-10-05 1984-10-05 Preparation of alpha-sulfo-fatty acid ester salt

Country Status (5)

Country Link
JP (1) JPS6187657A (en)
DE (1) DE3535184A1 (en)
ES (1) ES8609227A1 (en)
FR (1) FR2571368A1 (en)
PH (1) PH21117A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63161093A (en) * 1986-12-24 1988-07-04 旭電化工業株式会社 Powder detergent for clothing
JPH03111498A (en) * 1989-09-25 1991-05-13 Lion Corp Preparation of granular detergent composition of high bulk density
JPH05125397A (en) * 1991-03-25 1993-05-21 Clorox Co Method of sulfonating acyloxybenzenes and neutralizing obtained products
JPH0686683B2 (en) * 1986-12-17 1994-11-02 ビスコスウィッセ・エスアー Polyurethane multifilament elastic yarn
WO2004035717A1 (en) * 2002-10-16 2004-04-29 Lion Corporation PARTICLE CONTAINING α-SULFOFATTY ACID ALKYL ESTER SALT, PROCESS FOR PRODUCING THE SAME, AND DETERGENT

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4232874A1 (en) * 1992-09-30 1994-03-31 Henkel Kgaa Process for the preparation of surfactant granules
DE4235425A1 (en) * 1992-10-21 1994-04-28 Henkel Kgaa Process for the preparation of a granular detergent and cleaning agent
US5688982A (en) * 1993-08-20 1997-11-18 The Procter & Gamble Company No-bleach process for making sulfonated fatty acid alkyl ester surfactant
US5587500A (en) * 1993-09-17 1996-12-24 The Chemithon Corporation Sulfonation of fatty acid esters
US5475134A (en) * 1993-12-16 1995-12-12 The Procter & Gamble Co. Process for making sulfonated fatty acid alkyl ester surfactant

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DE3237001A1 (en) * 1982-10-06 1984-04-12 Lion Corp., Tokyo Process for the production of a detergent or cleaner with a salt of an alpha -sulpho fatty acid ester
JPS60133095A (en) * 1983-12-20 1985-07-16 ライオン株式会社 Granular detergent composition

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JPH0686683B2 (en) * 1986-12-17 1994-11-02 ビスコスウィッセ・エスアー Polyurethane multifilament elastic yarn
JPS63161093A (en) * 1986-12-24 1988-07-04 旭電化工業株式会社 Powder detergent for clothing
JPH03111498A (en) * 1989-09-25 1991-05-13 Lion Corp Preparation of granular detergent composition of high bulk density
JPH05125397A (en) * 1991-03-25 1993-05-21 Clorox Co Method of sulfonating acyloxybenzenes and neutralizing obtained products
WO2004035717A1 (en) * 2002-10-16 2004-04-29 Lion Corporation PARTICLE CONTAINING α-SULFOFATTY ACID ALKYL ESTER SALT, PROCESS FOR PRODUCING THE SAME, AND DETERGENT

Also Published As

Publication number Publication date
PH21117A (en) 1987-07-16
FR2571368A1 (en) 1986-04-11
ES547355A0 (en) 1986-09-01
ES8609227A1 (en) 1986-09-01
JPH045666B2 (en) 1992-02-03
DE3535184A1 (en) 1986-04-10

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