JPH0238639B2 - - Google Patents
Info
- Publication number
- JPH0238639B2 JPH0238639B2 JP58172156A JP17215683A JPH0238639B2 JP H0238639 B2 JPH0238639 B2 JP H0238639B2 JP 58172156 A JP58172156 A JP 58172156A JP 17215683 A JP17215683 A JP 17215683A JP H0238639 B2 JPH0238639 B2 JP H0238639B2
- Authority
- JP
- Japan
- Prior art keywords
- butylene
- sulfonate
- cleaning agent
- oligomer
- pentamer
- 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.)
- Expired - Lifetime
Links
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 19
- 239000012459 cleaning agent Substances 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 12
- 238000006277 sulfonation reaction Methods 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 alkenyl sulfonate Chemical compound 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Detergent Compositions (AREA)
Description
【発明の詳細な説明】
本発明は洗浄剤に関し、詳しくは消泡速度の大
きい洗浄剤に関する。
従来より、洗浄性，浸透性，起泡性，乳化性，
帯電防止性等を有する界面活性剤は工業的に各方
面で幅広く利用されており、とりわけドデシルベ
ンゼンスルホン酸ソーダおよびラウリル硫酸エス
テルソーダが大量に使用されている。
しかしながら、従来の洗浄剤は起泡性が強く、
しかも消泡速度が極めて小さいものであつた。そ
のため、河川などにおける環境悪化が極めて大き
な問題となつている。
そこで、本発明者は従来の洗浄性，浸透性，起
泡性等の優れた特性を維持しつつ、消泡速度の大
きい洗浄剤を開発すべく鋭意研究した結果、特定
のアルケニルスルホン酸塩が有用であることを見
出し、本発明を完成した。
すなわち、本発明はブチレンの３〜５重体のス
ルホン酸塩であつて、そのスルホン化率が60％以
上であるもの（以下、単にブチレンの３〜５量体
のスルホン酸塩と称することがある。）からなる
洗浄剤である。
ここで、ブチレンの３〜５量体のスルホン酸塩
とはｎ―ブチレン，イソブチレンあるいはこれら
の混合物の３〜５量体、すなわち平均炭素数12，
16，20のブチレンオリゴマーのスルホン酸塩であ
る。ここで、ブチレンオリゴマーのスルホン化率
は60％以上、好ましくは60〜70％である。なお、
スルホン化率は次式により求められる。
スルホン化率（％）
＝（原料のブチレンオリゴマーの臭素価）―（スル
ホン化ブチレンオリゴマーの臭素価）／原料のブチレン
オリゴマーの臭素価×100
スルホン酸の塩としては例えばアルカリ金属
塩，アルカリ土類金属塩，アミン塩，アンモニウ
ム塩等が挙げられるが、アルカリ金属塩およびア
ルカリ土類金属塩が好ましい。なかでも、ナトリ
ウム塩は最も好適である。洗浄剤として用いる場
合、ブチレンの３量体，４量体，５量体等のオリ
ゴマーのスルホン酸塩を単独であるいは２種以上
を混合して使用することができる。
本発明に用いるブチレンの３〜５量体のスルホ
ン酸塩は様々の方法で製造することができるが、
通常はブチレンの３〜５量体に無水硫酸あるいは
硫酸を反応させてスルホン化し、さらに水酸化ナ
トリウム，水酸化カリウム，水酸化カルシウムな
どでケン化することにより製造する。スルホン化
の条件は原料の種類などにより異なるが、一般的
にはSO3／ブチレンオリゴマー（モル比）＝1.1〜
2.0で反応温度常温〜80℃，反応時間１分以上の
条件で行なわれる。
また、ケン化は通常、アルカリ添加量は当量以
上で、100〜130℃に加熱し１時間以上反応させる
ことにより行なう。さらに、未反応原料などを除
去して目的とするブチレンオリゴマーのスルホン
酸塩を得る。
以上のようにして得られたブチレンの３〜５量
体のスルホン酸塩より洗浄剤を製造する。その場
合、必要により他の成分例えばアルキルベンゼン
スルホン酸塩，フエノール類のエチレンオキサイ
ド付加物などを適宜加えることができる。
本発明の洗浄剤は従来の代表的な洗浄剤と同等
の性能（表面張力，浸透力，初期起泡性など）を
有しているが、消泡速度に関しては従来のものよ
りも著しく大きいという特色がある。したがつ
て、本発明の洗浄剤は工場，家庭等において使用
された後、泡は速やかに消失する。そのため、従
来の洗浄剤の使用により惹起された環境汚染の問
題がなく安心して使用することができる。それ
故、本発明の洗浄剤は製紙業界、繊維業界などに
おける幅広い利用が期待される。
次に本発明を実施例により詳しく説明する。
実施例 １
イソブチレンオリゴマー（出光石油化学(株)製；
商品名IP―2028R：平均炭素数16のものが中心）
を内径12mm，長さ60cmの反応管を有する薄膜式ス
ルホン化装置に供給量1.0ml／minで膜厚0.2mm，
接触時間１分の条件で薄膜状に流下させた。これ
と同時に、反応管上部より２倍モル量のSo3ガス
を窒素ガスで希釈して導入しスルホン化反応を行
なつた。ここで、SO3ガスの供給量を0.32ml／
min，窒素ガスの流量を２／minとした。
このようにして得られた反応生成物32ｇを１当
量以上の水酸化ナトリウムにより中和し、さらに
110℃で２時間ケン化反応を行なつた。次いで、
ｎ―ヘキサンと50％イソプロパノール水溶液を用
い未反応オリゴマーとスルホン酸塩を抽出分離し
た。さらに、アルコール水溶液層を炭酸ナトリウ
ムで塩析してアルコール層と水層を分離し、アル
コール層より溶媒を留去してブチレンオリゴマー
のスルホン酸ナトリウムを30ｇ得た。この反応の
スルホン化率は65％であつた。
このようにして得られたブチレンオリゴマーの
スルホン酸ナトリウムは水分0.1％以下、未反応
オリゴマー0.1％以下の固形物であつた。この洗
浄剤につき界面活性能を測定した。結果を第１表
に示す。
比較例 １〜３
従来用いられているドデシルベンゼンスルホン
酸ソーダ（比較例１），ラウリル硫酸エステルソ
ーダ（比較例２）およびテトラデセンスルホネー
ト（比較例３）につき実施例１と同様に界面活性
能を測定した。結果を第１表に示す。
比較例 ４
実施例１に準じてスルホン化率55％のブチレン
オリゴマーのスルホン酸トリウムを得、このもの
につき実施例１と同様に界面活性能を測定した。
結果を第１表に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a cleaning agent, and more particularly to a cleaning agent with a high defoaming rate. Conventionally, cleaning properties, permeability, foaming properties, emulsifying properties,
Surfactants having antistatic properties are widely used in various industrial fields, and particularly sodium dodecylbenzenesulfonate and sodium lauryl sulfate are used in large quantities. However, conventional cleaning agents have strong foaming properties,
Moreover, the defoaming rate was extremely low. As a result, environmental deterioration in rivers and other areas has become an extremely serious problem. Therefore, as a result of intensive research to develop a cleaning agent with high defoaming speed while maintaining conventional excellent properties such as detergency, permeability, and foaming ability, the present inventor found that a specific alkenyl sulfonate They found it useful and completed the present invention. That is, the present invention is directed to a butylene tri- to pentamer sulfonate having a sulfonation rate of 60% or more (hereinafter sometimes simply referred to as a butylene trimer-pentamer sulfonate). .) is a cleaning agent. Here, the butylene trimer to pentamer sulfonate is a trimer to pentamer of n-butylene, isobutylene, or a mixture thereof, that is, an average carbon number of 12,
It is a sulfonate of butylene oligomers 16 and 20. Here, the sulfonation rate of the butylene oligomer is 60% or more, preferably 60 to 70%. In addition,
The sulfonation rate is determined by the following formula. Sulfonation rate (%) = (bromine number of raw material butylene oligomer) - (bromine number of sulfonated butylene oligomer) / bromine number of raw material butylene oligomer x 100 Examples of sulfonic acid salts include alkali metal salts and alkaline earth salts. Examples include metal salts, amine salts, ammonium salts, etc., but alkali metal salts and alkaline earth metal salts are preferred. Among these, sodium salts are most preferred. When used as a cleaning agent, oligomeric sulfonate salts of butylene trimers, tetramers, pentamers, etc. can be used alone or in combination of two or more. The butylene trimer to pentamer sulfonate used in the present invention can be produced by various methods, but
It is usually produced by reacting butylene trimer to pentamer with anhydrous sulfuric acid or sulfuric acid to sulfonate it, and then saponifying it with sodium hydroxide, potassium hydroxide, calcium hydroxide, etc. Sulfonation conditions vary depending on the type of raw materials, but generally SO 3 /butylene oligomer (molar ratio) = 1.1 ~
2.0, the reaction temperature is room temperature to 80°C, and the reaction time is 1 minute or more. Further, saponification is usually carried out by adding an alkali in an equivalent amount or more, heating the mixture to 100 to 130°C, and reacting for 1 hour or more. Furthermore, unreacted raw materials and the like are removed to obtain the desired butylene oligomer sulfonate. A cleaning agent is manufactured from the butylene trimer to pentamer sulfonate obtained as described above. In that case, other components such as alkylbenzene sulfonates, ethylene oxide adducts of phenols, etc. can be added as appropriate. The cleaning agent of the present invention has the same performance as typical conventional cleaning agents (surface tension, penetration power, initial foaming ability, etc.), but the defoaming rate is significantly higher than that of conventional cleaning agents. It has its own characteristics. Therefore, after the cleaning agent of the present invention is used in factories, homes, etc., the foam disappears quickly. Therefore, it can be used with confidence without the problem of environmental pollution caused by the use of conventional cleaning agents. Therefore, the cleaning agent of the present invention is expected to be widely used in the paper manufacturing industry, textile industry, etc. Next, the present invention will be explained in detail with reference to examples. Example 1 Isobutylene oligomer (manufactured by Idemitsu Petrochemical Co., Ltd.;
Product name IP-2028R: Mainly those with an average carbon number of 16)
was fed into a thin film sulfonation device with a reaction tube of 12 mm inner diameter and 60 cm length at a flow rate of 1.0 ml/min and a film thickness of 0.2 mm.
It was allowed to flow down in the form of a thin film under conditions of a contact time of 1 minute. At the same time, twice the molar amount of So 3 gas diluted with nitrogen gas was introduced from the top of the reaction tube to carry out a sulfonation reaction. Here, the supply amount of SO 3 gas is 0.32ml/
min, and the flow rate of nitrogen gas was set to 2/min. 32 g of the reaction product thus obtained was neutralized with 1 equivalent or more of sodium hydroxide, and then
The saponification reaction was carried out at 110°C for 2 hours. Then,
Unreacted oligomers and sulfonate salts were extracted and separated using n-hexane and 50% isopropanol aqueous solution. Furthermore, the alcohol aqueous solution layer was salted out with sodium carbonate to separate the alcohol layer and the aqueous layer, and the solvent was distilled off from the alcohol layer to obtain 30 g of sodium sulfonate of butylene oligomer. The sulfonation rate of this reaction was 65%. The sodium sulfonate of butylene oligomer thus obtained was a solid substance with a water content of 0.1% or less and an unreacted oligomer content of 0.1% or less. The surfactant ability of this detergent was measured. The results are shown in Table 1. Comparative Examples 1 to 3 The surfactant properties of conventionally used sodium dodecylbenzenesulfonate (Comparative Example 1), sodium lauryl sulfate (Comparative Example 2), and tetradecene sulfonate (Comparative Example 3) were tested in the same manner as in Example 1. It was measured. The results are shown in Table 1. Comparative Example 4 Thorium sulfonate of butylene oligomer having a sulfonation rate of 55% was obtained according to Example 1, and the surfactant ability of this product was measured in the same manner as in Example 1.
The results are shown in Table 1. 【table】
Claims (1)
て、そのスルホン化率が60％以上であるものから
なる洗浄剤。 ２ ブチレンがｎ―ブチレンおよび／またはイソ
ブチレンである特許請求の範囲第１項記載の洗浄
剤。[Scope of Claims] 1. A cleaning agent comprising a sulfonate of trimer to pentamer of butylene and having a sulfonation rate of 60% or more. 2. The cleaning agent according to claim 1, wherein the butylene is n-butylene and/or isobutylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58172156A JPS6064624A (en) | 1983-09-20 | 1983-09-20 | Surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58172156A JPS6064624A (en) | 1983-09-20 | 1983-09-20 | Surfactant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6064624A JPS6064624A (en) | 1985-04-13 |
| JPH0238639B2 true JPH0238639B2 (en) | 1990-08-31 |
Family
ID=15936602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58172156A Granted JPS6064624A (en) | 1983-09-20 | 1983-09-20 | Surfactant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6064624A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5720994A (en) * | 1980-05-23 | 1982-02-03 | Texas Instruments Inc | Programmable read only memory cell and process for producing same |
| JPS57149391A (en) * | 1981-03-13 | 1982-09-14 | Nippon Oil & Fats Co Ltd | Additive for coal/alcohol slurry |
-
1983
- 1983-09-20 JP JP58172156A patent/JPS6064624A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5720994A (en) * | 1980-05-23 | 1982-02-03 | Texas Instruments Inc | Programmable read only memory cell and process for producing same |
| JPS57149391A (en) * | 1981-03-13 | 1982-09-14 | Nippon Oil & Fats Co Ltd | Additive for coal/alcohol slurry |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6064624A (en) | 1985-04-13 |
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