JPH0446149A - Alkyl ether sulfate and production thereof - Google Patents
Alkyl ether sulfate and production thereofInfo
- Publication number
- JPH0446149A JPH0446149A JP15118490A JP15118490A JPH0446149A JP H0446149 A JPH0446149 A JP H0446149A JP 15118490 A JP15118490 A JP 15118490A JP 15118490 A JP15118490 A JP 15118490A JP H0446149 A JPH0446149 A JP H0446149A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl ether
- ether sulfate
- sulfate
- ethylene oxide
- carbonyl value
- 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
- -1 Alkyl ether sulfate Chemical class 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 16
- 150000005215 alkyl ethers Chemical class 0.000 claims abstract description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 11
- 239000004435 Oxo alcohol Substances 0.000 claims abstract description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims abstract description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 15
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000001180 sulfating effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims 1
- 238000005187 foaming Methods 0.000 abstract description 9
- 239000011734 sodium Substances 0.000 abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 7
- 239000003599 detergent Substances 0.000 abstract description 7
- 229910052708 sodium Inorganic materials 0.000 abstract description 7
- 239000002453 shampoo Substances 0.000 abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940057402 undecyl alcohol Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940074096 monoolein Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、起泡力および洗浄力が良好であり、かつ臭気
の改善されたアルキルエーテル硫酸塩およびその製造方
法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an alkyl ether sulfate having good foaming power and detergent power and improved odor, and a method for producing the same.
アルキルエーテル硫酸塩は、皮膚に対してマイルドであ
り、食器用洗浄剤やンヤングーの主剤として有用である
。Alkyl ether sulfates are mild to the skin and are useful as the main ingredient in dishwashing detergents and green tea.
従来、洗浄剤として用いられるアルキルエーテル硫酸塩
は、その原料として、炭素数１２および１４の高級アル
コールを主成分とするヤシ油アルコール等の天然アルコ
ールや、α−オレフィンまたは内部オレフィンからオキ
ソ法により得られる炭素数１２〜１５の合成アルコール
等が用いられていた。Conventionally, alkyl ether sulfates used as cleaning agents are obtained by the oxo method from natural alcohols such as coconut oil alcohol whose main components are higher alcohols with 12 and 14 carbon atoms, α-olefins or internal olefins. Synthetic alcohols having 12 to 15 carbon atoms were used.
これらの高級アルコールは、ＮａＯＨ，、ＫＯＨ’Ｓの
塩基触媒、または、ＢＰ、等の酸触媒の存在下に酸化エ
チレンを反応させてアルキルエトキンレートとし、これ
を硫酸化した後、塩基により中和して、アルキルエーテ
ル硫酸塩が製造されている。These higher alcohols are produced by reacting ethylene oxide in the presence of a base catalyst such as NaOH, KOH'S, or an acid catalyst such as BP to form an alkyl ethkylate, which is sulfated and then neutralized with a base. In this way, alkyl ether sulfates are produced.
これらの高級アルコールから製造されるアルキルエーテ
ル硫酸塩は、ドクダミ臭に似た特異臭が強く、食器用洗
浄剤やシャンプー等の直接手肌に触れる洗浄剤に配合さ
れる場合には、香料等によって臭気をマスキングする必
要があった。Alkyl ether sulfates produced from these higher alcohols have a strong distinctive odor similar to the odor of hectic smelt, and when added to detergents that come into direct contact with the skin, such as dishwashing detergents and shampoos, they may be mixed with fragrances, etc. It was necessary to mask the odor.
本発明の目的は、起泡力および洗浄力が良好であり、か
つ臭気の改善されたアルキルエーテル硫酸塩およびその
製造方法を提供することである。An object of the present invention is to provide an alkyl ether sulfate having good foaming power and detergency and improved odor, and a method for producing the same.
本発明は、カルボニル価が５〜１５０ｐｐｍである炭素
数１１のオキソアルコールに酸化エチレンを付加して得
られるポリオキシエチレンアルキルエーテルを硫酸化す
ることによって得られるアルキルエーテル硫酸塩および
その製造方法である。The present invention is an alkyl ether sulfate obtained by sulfating a polyoxyethylene alkyl ether obtained by adding ethylene oxide to an oxo alcohol having 11 carbon atoms and a carbonyl value of 5 to 150 ppm, and a method for producing the same. .
本発明に用いられる炭素数１１のアルコールは、炭素数
１０の直鎖α−オレフィンまたは直鎖内部オレフィンを
コバルト等の金属触媒を含む系において水素と一酸化炭
素との混合ガスと反応させるいわゆるオキソ法によって
得られる炭素数１１のアルコールを、接触水素化等によ
ってカルボニル価を減少させ、５〜１５０ｐｐｍ、好ま
しくは１０〜１２０ｐｐｍの範囲に調整したものである
。The alcohol having 11 carbon atoms used in the present invention is produced by reacting a straight-chain α-olefin or a straight-chain internal olefin having 10 carbon atoms with a mixed gas of hydrogen and carbon monoxide in a system containing a metal catalyst such as cobalt. The carbonyl value of an alcohol having 11 carbon atoms obtained by the method is reduced by catalytic hydrogenation or the like to have a carbonyl value in the range of 5 to 150 ppm, preferably 10 to 120 ppm.
般に、炭素数１０以下のアルコールエトキンレトの硫酸
塩は、洗浄力および起泡力が低いことが知られている。Generally, sulfates of alcohols having 10 or less carbon atoms are known to have low detergency and foaming power.
また、炭素数１２以上のオキソアルコール、例えば、ド
デカノールやドパノール２３ （三菱油化■製、炭素数
１２および１３アルコールの混合物）では、硫酸塩とし
たときに特異臭が強い。Further, oxo alcohols having 12 or more carbon atoms, such as dodecanol and Dopanol 23 (manufactured by Mitsubishi Yuka Corporation, a mixture of 12 and 13 carbon atoms), have a strong specific odor when converted into sulfates.
炭素数１１のウンデカノールを用いる場合でも、起泡力
および洗浄力は良好であるが、そのカルボニル価が５ｐ
ｐｍ未満ではアルキルエーテル硫酸塩としたときの臭気
が十分低くならず、また１５０ｐｐｍを越えるとアルキ
ルエーテル硫酸塩としたときに色相が劣化する。Even when undecanol having 11 carbon atoms is used, the foaming power and cleaning power are good, but the carbonyl value is 5p.
If it is less than pm, the odor will not be sufficiently reduced when it is made into an alkyl ether sulfate, and if it exceeds 150 ppm, the hue will deteriorate when it is made into an alkyl ether sulfate.
本発明の硫酸塩の製造方法は、先ず、上記のウシデカノ
ールに、アルカリ金属触媒の存在下に酸化エチレンを付
加させることによって、ポリオキシエチレンアルキルエ
ーテルとする。この反応は、通常、ｊ′ルコールに対し
て５００〜２０００重量ｐｐｍのＮａ０ｔ（、ＫＯＨ等
を水溶液としてアル：」−ルに加え、水を減圧等で除去
した後、酸化エチレンを加えて、反応温度１５０〜１９
０℃、好ましくは、１６０〜１８０℃、反応圧力を酸化
エチレンの分圧で１〜２ ｋｇｔ’ｃｍ’として行う。In the method for producing a sulfate of the present invention, first, ethylene oxide is added to the above-described bosidecanol in the presence of an alkali metal catalyst to produce polyoxyethylene alkyl ether. This reaction is usually carried out by adding 500 to 2000 ppm by weight of Na0t(, KOH, etc.) to alcohol as an aqueous solution, removing water under reduced pressure, etc., then adding ethylene oxide, and reacting. Temperature 150-19
The reaction is carried out at 0°C, preferably from 160 to 180°C, and at a reaction pressure of 1 to 2 kgt'cm' (partial pressure of ethylene oxide).
ここで得られるフルコール」−ドキンレートのポリオキ
／エチレン鎮は、目的物である硫酸塩の洗浄力および起
泡力の点て、酸化エチレンの平均付加モル数が１〜４の
ものが好ましい。In view of the detergency and foaming power of the target sulfate, the polyoxyethylene/fluorol-doquinate polyoxyethylene compound obtained here preferably has an average number of added moles of ethylene oxide of 1 to 4.
次いで、上記で得られるポリオキシエチレンアルキルエ
ーテルを、ＳＯ２またはクロロスルホン酸で硫酸化して
アルキルエーテル硫酸ニスデルとし、続いてアルカリ金
属やトリエタノールアミンの水溶液で中和することによ
り、目的のアルキルエーテル硫酸塩を得ることができる
。硫酸化は、通常、窒素または空気によって希釈された
ガス状のＳＯｌまたは液体のクロロスルホン酸をポリオ
キシエチレンアルキルエーテルに対し１．０２〜１．０
５モル用い、３０℃以下で行う。Ｓ０３を用いる場合に
は、薄膜式硫酸化装置（フィルムリアクター）を用いる
のが船釣である。硫酸化物の中和剤としては、ＮａＯＨ
，ＫＯＨ、トリエタノールアミンが実用的で好ましい。Next, the polyoxyethylene alkyl ether obtained above is sulfated with SO2 or chlorosulfonic acid to obtain alkyl ether nisdel sulfate, and then neutralized with an aqueous solution of an alkali metal or triethanolamine to obtain the desired alkyl ether sulfate. You can get salt. Sulfation is typically carried out using gaseous SOI or liquid chlorosulfonic acid diluted with nitrogen or air to a polyoxyethylene alkyl ether of 1.02 to 1.0
Using 5 mol, the reaction is carried out at 30°C or lower. When using S03, a thin film sulfation device (film reactor) is used for boat fishing. As a neutralizing agent for sulfates, NaOH
, KOH, and triethanolamine are practical and preferred.
本発明のアルキルエーテル硫酸塩は、その原料として、
アルコールの炭素数が１１のものを用いるが、他の炭素
数のアルコールを、臭気を悪化させない程度、例えばド
パノール２３であれば、１０重量％未満含有することが
できる。The alkyl ether sulfate of the present invention has, as its raw material,
Although an alcohol having 11 carbon atoms is used, alcohols having other carbon atoms may be contained to an extent that does not worsen the odor, for example, less than 10% by weight if Dopanol 23 is used.
本発駅のアルキルエーテル硫酸塩を洗浄剤として用いる
場合には、必要に応じて、色素、香料、可溶化剤、ビル
ダー等の補助剤を適宜加えることができる。さらに、洗
浄力や泡立ちを調整する目的で、他のアニオン界面活性
剤、カチオン活性剤、両性界面活性剤を、臭気を悪化さ
せない範囲において添加することができる。When using the alkyl ether sulfate of the present invention as a cleaning agent, auxiliary agents such as dyes, fragrances, solubilizers, builders, etc. can be added as necessary. Furthermore, for the purpose of adjusting detergency and foaming, other anionic surfactants, cationic surfactants, and amphoteric surfactants may be added within a range that does not worsen odor.
本発明のアルキルエーテル硫酸塩を用いた洗浄剤は、特
異臭が少ないので、シャンプー、ボディシャンプー、リ
キッドソープ、台所洗剤等の広い用途に応用することが
できる。Since the cleaning agent using the alkyl ether sulfate of the present invention has little peculiar odor, it can be applied to a wide range of uses such as shampoo, body shampoo, liquid soap, and kitchen detergent.
次に、本発明を実施例によってさらに詳しく説明する。 Next, the present invention will be explained in more detail by way of examples.
〈実施例１〉
ローデセンを、オキソ法によって水素および一酸化炭素
と反応させて得たウンデシルアルコール（直鎮率７５％
）に、Ｎｉ触媒存在下に水素を添加することによって、
そのカルボニル価を７ｐｐｍとし、これにＮａ触媒下で
酸化エチレンを２モル付加させて、ウンデシルアルコー
ルエトキシレートを得た。<Example 1> Undecyl alcohol obtained by reacting rhodecene with hydrogen and carbon monoxide by the oxo method (direct reaction rate 75%)
) by adding hydrogen in the presence of a Ni catalyst,
The carbonyl value was adjusted to 7 ppm, and 2 moles of ethylene oxide was added thereto under an Na catalyst to obtain undecyl alcohol ethoxylate.
上記のウンデシルアルコールエトキシレートに１．０２
当量のクロルスルホン酸を３０℃以下で添加し、硫酸エ
ステル化した。1.02 for the above undecyl alcohol ethoxylate
An equivalent amount of chlorosulfonic acid was added at a temperature below 30°C to form a sulfuric acid ester.
この硫酸エステルを４％水酸化ナトリウム水溶液で中和
して、アルキルニーデル硫酸す） ＩＪウムを水溶液と
して得た。反応は定量的に進行した。This sulfuric ester was neutralized with a 4% aqueous sodium hydroxide solution to obtain alkyl needle sulfate (IJ) as an aqueous solution. The reaction proceeded quantitatively.
〈実施例２〉
ウンデシルアルコールの水素添加の際に、カルボニル価
を２０ｐｐｍとした以外は、実施例１と同様にして、ア
ルキルエーテル硫酸ナトリウムを水溶液として得た。<Example 2> Sodium alkyl ether sulfate was obtained as an aqueous solution in the same manner as in Example 1, except that the carbonyl value was 20 ppm during hydrogenation of undecyl alcohol.
〈実施例３〉
ウンデシルアルコールの水素添加の際に、カルボニル価
を１２０ｐｐｍとした以外は、実施例１と同様にして、
アルキルエーテル硫酸ナトリウムを水溶液として得た。<Example 3> In the same manner as in Example 1, except that the carbonyl value was 120 ppm during hydrogenation of undecyl alcohol,
Sodium alkyl ether sulfate was obtained as an aqueous solution.
く比較例１〉
ウンデシルアルコールの水素添加の際に、カルボニル価
をｌｐｐｍ以下とした以外は、実施例１と同様にして、
アルキルエーテル硫酸ナトリウムを水溶液として得た。Comparative Example 1> In the same manner as in Example 1, except that the carbonyl value was set to 1 ppm or less during hydrogenation of undecyl alcohol,
Sodium alkyl ether sulfate was obtained as an aqueous solution.
〈比較例２〉
ウンデシルアルコールの水素添加の際に、カルボニル価
を１８０ｐｐｍとした以外は、実施例１と同様にして、
アルキルエーテル硫酸ナトリウムを水溶液として得た。<Comparative Example 2> In the same manner as in Example 1, except that the carbonyl value was 180 ppm during hydrogenation of undecyl alcohol,
Sodium alkyl ether sulfate was obtained as an aqueous solution.
く比較例３〉
ウンデシルアルコールの代わりにドデシルアルコール（
直鎖率１００％、カルボニル価３５ ｐ ｐｍ）を用い
た以外は、実施例１と同様にして、アルキルエーテル硫
酸ナトリウムを水溶液として得た。Comparative Example 3> Dodecyl alcohol (
Sodium alkyl ether sulfate was obtained as an aqueous solution in the same manner as in Example 1, except that a straight chain ratio of 100% and a carbonyl value of 35 ppm were used.
く比較例４〉
ウンデシルアルコールの代わりにドパノール２３（三菱
油化■製、Ｃ１□−１３アルコール、直鎖率７２％、カ
ルボニル価２５ｐｐｍｊを用いた以外は、実施例１と同
様にして、アルキルエーテル硫酸ナトリウムを水溶液と
して得た。Comparative Example 4 In the same manner as in Example 1, except that Dopanol 23 (manufactured by Mitsubishi Yuka ■, C1□-13 alcohol, linear chain ratio 72%, carbonyl value 25 ppmj) was used instead of undecyl alcohol, alkyl Sodium ether sulfate was obtained as an aqueous solution.
評価例
実施例および比較例で得られたアルキルエーテル硫酸す
） ＩＪウム水溶液について、臭気、色相を評価し、そ
の結果を表１に示した。Evaluation Examples The aqueous alkyl ether sulfate solutions obtained in Examples and Comparative Examples were evaluated for odor and hue, and the results are shown in Table 1.
（評価方法）
・臭気
アルキルエーテル硫酸塩水溶液を、蒸留水で希釈し、硫
酸塩の濃度を１０重量％に調製した。その臭いを、年齢
２０〜３０歳の成人男女合わせて１０人に５段階に評価
させた。その結果を人数で示す。(Evaluation method) - A odorous alkyl ether sulfate aqueous solution was diluted with distilled water to adjust the sulfate concentration to 10% by weight. A total of 10 male and female adults between the ages of 20 and 30 were asked to rate the odor on a five-point scale. The results will be shown in terms of number of people.
◎・・殆ど無臭
○・・多少臭気はあるが、気にならない△・・臭気が少
しあり、気になる
×・・悪臭
××・非常に悪臭
（但し、評価の際は、評価者が試験液の内容を知らない
いわゆるブラインド法で行った）
・色相
アルキルエーテル硫酸塩水溶液を、蒸留水で希釈し、１
０重量％とじ、この水溶液の４２０ｎｍにおける吸光度
を１０００倍した数値くクレット色）で表す。◎... Almost odorless ○... There is some odor, but it doesn't bother me △... There is a little odor, which bothers me ×... Bad odor ×× - Very bad odor (However, when evaluating (This was done using a so-called blind method in which the contents of the liquid were not known) - The aqueous alkyl ether sulfate solution was diluted with distilled water, and 1
0% by weight, and is expressed as a value obtained by multiplying the absorbance of this aqueous solution at 420 nm by 1000 (Clette color).
表１
く応用例ン
炭素数１０のアルコール（直鎮率１００％、カルボニル
価３０ ｐ ｐｍ＞を用い、実施例１と同様にしてアル
キルエーテル硫酸塩を製造した。Table 1 Application Example An alkyl ether sulfate was produced in the same manner as in Example 1 using an alcohol having 10 carbon atoms (direct conversion rate: 100%, carbonyl value: 30 ppm).
この硫酸塩（Ｃ，。）と実施例２および比較例３で得ら
れた硫酸塩のそれぞれについて、起泡力と洗浄力を評価
した。その結果を表２に示す。This sulfate (C,.) and the sulfates obtained in Example 2 and Comparative Example 3 were evaluated for foaming power and detergency. The results are shown in Table 2.
（評価方法）
・起泡力（ロス・フィルス法）
アルキルエーテル硫酸塩の濃度が０１重量％となるよう
に硬度３°ＤＨの水で調製し、その溶液２００−を、同
溶液５０−の入った直径５ｃｍのシリンダー中へ、液面
から９０ｃｍの高さから自白落下させた。その衝撃撹乱
によって生ずる泡の高さをシリンダーの目盛りで読み取
った。(Evaluation method) ・Foaming power (Ross-fils method) The concentration of alkyl ether sulfate was prepared with water having a hardness of 3° DH so that the concentration was 0.1% by weight, and the solution 200- was mixed with 50- The liquid was dropped from a height of 90 cm from the liquid level into a cylinder with a diameter of 5 cm. The height of the bubbles produced by the impact disturbance was read on the scale of the cylinder.
洗浄力（リーナッソ改良洗浄試験法ＪＩＳ Ｋ−３３７
０）スライドグラスをモデル汚垢（牛脂と大豆油の当量
混合物２０ｇ、モノオレイン０．２５ｇ、オイルレッド
０．１ｇをクロロホルム６０−に溶解したもの）に１〜
２秒浸漬して汚垢を付着させ、風乾後、リーナッソ改良
洗浄力試験器を用いて試験した。試験溶液はアルキルエ
ーテル硫酸塩のＯ，１重量％水溶液で行い、これに使用
した水の硬度は、３°Ｄｌ（で、温度は２５℃であった
。Cleaning power (Linasso improved cleaning test method JIS K-337
0) A slide glass was immersed in a model stain (20 g of an equivalent mixture of beef tallow and soybean oil, 0.25 g of monoolein, and 0.1 g of oil red dissolved in 60-chloroform).
Dirt was immersed for 2 seconds to adhere dirt, and after air drying, it was tested using a Linasso improved detergency tester. The test solution was an O, 1% by weight aqueous solution of alkyl ether sulfate, the hardness of the water used was 3°Dl (and the temperature was 25°C).
洗浄力は、下式より算出した。The detergency was calculated using the formula below.
Ｗｓ Ｗｓ：洗浄前の油汚垢付着量 ＷＷ、洗浄後の油汚垢付着量 表Ws Ws: Amount of oil stains before cleaning WW, amount of oil stains after cleaning table
Claims (5)
１のオキソアルコールから得られるポリオキシエチレン
アルキルエーテル硫酸塩。(1) 1 carbon number with a carbonyl value of 5 to 150 ppm
Polyoxyethylene alkyl ether sulfate obtained from the oxo alcohol of No. 1.
である特許請求の範囲第１項記載の硫酸塩。(2) The sulfate according to claim 1, wherein the sulfate is a Na salt, a K salt, or a triethanolamine salt.
ル数が１〜４である特許請求の範囲第１項記載の硫酸塩
。(3) The sulfate according to claim 1, wherein the average number of moles of ethylene oxide added to the polyoxyethylene chain is 1 to 4.
１のオキソアルコールに酸化エチレンを付加して得られ
るポリオキシエチレンアルキルエーテルを硫酸化するこ
とを特徴とするアルキルエーテル硫酸塩の製造方法。(4) 1 carbon number with a carbonyl value of 5 to 150 ppm
1. A method for producing an alkyl ether sulfate, which comprises sulfating a polyoxyethylene alkyl ether obtained by adding ethylene oxide to the oxoalcohol of No. 1.
酸化する特許請求の範囲第４項記載の製造方法。(5) The manufacturing method according to claim 4, which comprises sulfating with gaseous sulfur trioxide or chlorosulfonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15118490A JPH0446149A (en) | 1990-06-08 | 1990-06-08 | Alkyl ether sulfate and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15118490A JPH0446149A (en) | 1990-06-08 | 1990-06-08 | Alkyl ether sulfate and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0446149A true JPH0446149A (en) | 1992-02-17 |
Family
ID=15513122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15118490A Pending JPH0446149A (en) | 1990-06-08 | 1990-06-08 | Alkyl ether sulfate and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0446149A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0722916A1 (en) * | 1995-01-23 | 1996-07-24 | ENIRICERCHE S.p.A. | Cement composition and its use for the preparation of lightweight concretes |
-
1990
- 1990-06-08 JP JP15118490A patent/JPH0446149A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0722916A1 (en) * | 1995-01-23 | 1996-07-24 | ENIRICERCHE S.p.A. | Cement composition and its use for the preparation of lightweight concretes |
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