JP4653999B2 - Additive for anionic surfactant - Google Patents
Additive for anionic surfactant Download PDFInfo
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- JP4653999B2 JP4653999B2 JP2004306015A JP2004306015A JP4653999B2 JP 4653999 B2 JP4653999 B2 JP 4653999B2 JP 2004306015 A JP2004306015 A JP 2004306015A JP 2004306015 A JP2004306015 A JP 2004306015A JP 4653999 B2 JP4653999 B2 JP 4653999B2
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- 239000003945 anionic surfactant Substances 0.000 title claims description 27
- 239000000654 additive Substances 0.000 title description 13
- 230000000996 additive effect Effects 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims description 46
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 4
- 230000001180 sulfating effect Effects 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- -1 alkyl ether sulfate Chemical class 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006386 neutralization reaction Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 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 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 229920001281 polyalkylene Polymers 0.000 description 5
- 230000019635 sulfation Effects 0.000 description 5
- 238000005670 sulfation reaction Methods 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
Description
本発明はアニオン界面活性剤用添加剤、それを含むアニオン界面活性剤組成物及びその製造方法に関する。詳しくはアルキルエーテルサルフェート組成物の流動化剤として有用な新規なアニオン界面活性剤用添加剤、該添加剤を含むことにより、アルキルエーテルサルフェートを高濃度に含有していても、良好な流動性を有するアニオン界面活性剤組成物、及びその製造方法に関する。 The present invention relates to an anionic surfactant additive, an anionic surfactant composition containing the additive, and a method for producing the same. Specifically, a novel anionic surfactant additive useful as a fluidizing agent for an alkyl ether sulfate composition, and by including the additive, good fluidity can be obtained even when the alkyl ether sulfate is contained at a high concentration. The present invention relates to an anionic surfactant composition and a method for producing the same.
高級アルコールのアルキレンオキシド付加体（オキシアルキレンアルキルエーテル）の硫酸化により得られるアルキルエーテルサルフェートは、皮膚に対する刺激が少なく、液体洗浄剤、例えば、シャンプー、医薬、化粧品用のアニオン界面活性剤として広く使用されている。 Alkyl ether sulfates obtained by sulfation of alkylene oxide adducts of higher alcohols (oxyalkylene alkyl ethers) are less irritating to the skin and are widely used as liquid detergents, for example, anionic surfactants for shampoos, pharmaceuticals and cosmetics. Has been.
アルキルエーテルサルフェートは、通常、水を含有するペースト状又は液状組成物として製造されるが、その有効成分濃度は、取り扱い性、製造装置の効率、製品輸送のコスト、流動性などを考慮して出来るだけ高濃度に設定されている。アルキルエーテルサルフェート組成物の流動性は、原料高級アルコールの化学構造、オキシアルキレン基の繰返し数、未反応オキシアルキレンアルキルエーテルの量、副生アルキレンエーテルグリコール及び無機塩類等の含有量などに影響され、同一有効成分濃度においてもその流動性は著しく異なる。例えば、ドラムからアルキルエーテルサルフェート組成物の抜き出しが困難になる程流動性が低下することがあることも知られている。したがって、アルキルエーテルサルフェートの濃度を下げることなくこれを高濃度で含む組成物の流動性を改善できれば、生産効率が向上すると共に輸送コストが減少し、工業的に極めて有利である。 Alkyl ether sulfate is usually produced as a paste-like or liquid composition containing water, but the concentration of the active ingredient can be determined in consideration of handling properties, efficiency of production equipment, cost of product transportation, fluidity, etc. Only high concentration is set. The fluidity of the alkyl ether sulfate composition is affected by the chemical structure of the raw material higher alcohol, the number of repeating oxyalkylene groups, the amount of unreacted oxyalkylene alkyl ether, the content of by-product alkylene ether glycol and inorganic salts, etc. Even at the same active ingredient concentration, the fluidity is significantly different. For example, it is also known that the fluidity may decrease as the extraction of the alkyl ether sulfate composition from the drum becomes difficult. Therefore, if the fluidity of a composition containing a high concentration of the alkyl ether sulfate can be improved without reducing the concentration, the production efficiency is improved and the transportation cost is reduced, which is extremely advantageous industrially.
流動性を向上させたアルキルエーテルサルフェート組成物としては、例えば（１）アルキルエーテルサルフェートと、ポリアルキレンエーテルグリコールから得られたポリアルキレンエーテルグリコールジ硫酸エステルのモノ及び／又はジ塩を粘度調整剤として含有する組成物（例えば、特許文献１参照）、（２）オキシアルキレンアルキルエーテル硫酸エステルの中和工程時又は中和後に平均分子量３００〜６０００のポリエチレングリコールを、該硫酸化物に対して０．１〜２５重量％の割合で添加して得られる低粘度界面活性剤（例えば、特許文献２参照）などが開示されている。 Examples of the alkyl ether sulfate composition with improved fluidity include (1) mono- and / or di-salts of polyalkylene ether glycol disulfate obtained from (1) alkyl ether sulfate and polyalkylene ether glycol. Composition (for example, refer to Patent Document 1), (2) 0.1 to 0.1 mol of polyethylene glycol having an average molecular weight of 300 to 6000 during or after the neutralization step of the oxyalkylene alkyl ether sulfate. A low-viscosity surfactant obtained by adding at a ratio of ˜25% by weight (for example, see Patent Document 2) is disclosed.
前記（１）の組成物に関しては、より高い流動性を示す組成物が望まれている。前記（１）の組成物に添加されている粘度調整剤は、分子量が６００以上、好ましくは１０００以上のポリアルキレンエーテルグリコールから得られたポリアルキレンエーテルグリコールジ硫酸エステルのモノ及び／又はジ塩である。特許文献１には、この粘度調整剤の作用は、原料ポリアルキレンエーテルグリコールの分子量の上昇と共に増大すると記載されている。 With respect to the composition (1), a composition exhibiting higher fluidity is desired. The viscosity modifier added to the composition of (1) is a mono and / or di salt of polyalkylene ether glycol disulfate obtained from polyalkylene ether glycol having a molecular weight of 600 or more, preferably 1000 or more. is there. Patent Document 1 describes that the action of the viscosity modifier increases as the molecular weight of the raw material polyalkylene ether glycol increases.
前記（２）の組成物で用いているポリエチレングリコールは、界面活性剤水溶液の流動性を向上させる効果が、前記（１）で用いている粘度調整剤に比べて低く、満足し得る組成物ではない。 The polyethylene glycol used in the composition of the above (2) has a lower effect of improving the fluidity of the aqueous surfactant solution than the viscosity modifier used in the above (1), and is a satisfactory composition. Absent.
本発明は、アルキルエーテルサルフェート組成物の流動化剤として有用な新規な添加剤、該添加剤を含むことにより、直鎖のアルキルエーテルサルフェートを高濃度に含有していても、良好な流動性を有するアニオン界面活性剤組成物、及びその製造方法を提供することを目的とする。
The present invention relates to novel additives useful as a fluidizing agent of alkyl ether sulfates composition, by containing the additive, also contain alkyl ether sulfates of linear high concentration, good fluidity It aims at providing the anionic surfactant composition which has, and its manufacturing method.
本発明者らは、アルキレンエーテルグリコールの分子量と、その硫酸エステルの塩の流動化能との関係を研究した結果、特許文献１の教示に反して、低分子量のアルキレンエーテルグリコールから得られた硫酸エステルの塩にも、アルキルエーテルサルフェート組成物の流動性向上効果があることを見出した。 As a result of studying the relationship between the molecular weight of alkylene ether glycol and the fluidization ability of the sulfate ester salt, the present inventors have found that sulfuric acid obtained from low molecular weight alkylene ether glycol is contrary to the teaching of Patent Document 1. It has been found that the ester salt also has an effect of improving the fluidity of the alkyl ether sulfate composition.
すなわち、本発明は、
（ｉ）式（１）で表される化合物の１種以上からなるＡ成分と、式（２）で表される化合物の１種以上からなるＢ成分と、水とを含み、Ａ成分、Ｂ成分および水の合計に対して、Ｂ成分を６５〜９０質量％含む、アニオン界面活性剤組成物、
式（１）：
ＺＯ（Ａ1Ｏ）nＳＯ3Ｍ1 （１）
（式中、Ｍ1はアルカリ金属またはＮＨ4を示し、Ｚは水素原子又はＳＯ3Ｍ2（式中、Ｍ2はアルカリ金属、ＮＨ4又は水素原子を示す）を示し、Ａ1は炭素数２〜４のアルキレン基、ｎは平均値で１．０〜１２の数を示し、−（Ａ1Ｏ）n−の分子量は１００〜５５０である）
式（２）：
ＲＯ（Ａ2Ｏ）mＳＯ3Ｍ3 （２）
（式中、Ｒは炭素数９〜２４の直鎖のアルキル基又はアルケニル基、Ａ2は炭素数２〜４のアルキレン基、Ｍ3は水素原子、アルカリ金属又はＮＨ4、ｍは平均値で０．１〜１００の数を示す）、および
（ii）前記アニオン界面活性剤組成物の製造方法
を提供する。
That is, the present invention
(I) A component comprising one or more compounds represented by the formula (1), a B component comprising one or more compounds represented by the formula (2), and water. An anionic surfactant composition comprising 65 to 90% by mass of component B based on the total amount of components and water;
Formula (1):
ZO (A 1 O) n SO 3 M 1 (1)
(In the formula, M 1 represents an alkali metal or NH 4 , Z represents a hydrogen atom or SO 3 M 2 (wherein M 2 represents an alkali metal, NH 4 or a hydrogen atom), and A 1 represents the number of carbon atoms. 2 to 4 alkylene groups, n represents an average value of 1.0 to 12, and-(A 1 O) n -has a molecular weight of 100 to 550)
Formula (2):
RO (A 2 O) m SO 3 M 3 (2)
(Wherein, R represents an alkyl or alkenyl group having a straight chain of 9-24 carbon atoms, A 2 is an alkylene group having 2 to 4 carbon atoms, M 3 is a hydrogen atom, an alkali metal or NH 4, m is an average value Represents a number from 0.1 to 100 ), and
(Ii) A method for producing the anionic surfactant composition is provided.
本発明によれば、アルキルエーテルサルフェート組成物の流動化剤として有用な、従来よりも低分子量の新規アニオン界面活性剤用添加剤を提供することができる。さらに、本発明によれば、前記添加剤を含むことにより、高濃度のアルキルエーテルサルフェートを含有しても、良好な流動性を有するアニオン界面活性剤組成物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the additive for novel anionic surfactants useful as a fluidizing agent of an alkyl ether sulfate composition and having a lower molecular weight than conventional can be provided. Furthermore, according to this invention, even if it contains the high concentration alkyl ether sulfate, the anionic surfactant composition which has favorable fluidity | liquidity can be provided by including the said additive.
本発明のアニオン界面活性剤用添加剤は、式（１）：
ＺＯ（Ａ1Ｏ）ｎＳＯ3Ｍ1 （１）
で表されるアルキレンエーテルグリコール硫酸エステルの塩（ＡＥＧＳ）から選ばれた化合物を少なくとも１種含んでなり、アルキルエーテルサルフェート（ＥＳ）組成物の流動化剤として作用する。
The anionic surfactant additive of the present invention has the formula (1):
ZO (A 1 O) nSO 3 M 1 (1)
It comprises at least one compound selected from the salt (AEGS) of an alkylene ether glycol sulfate represented by the formula (1) and acts as a fluidizing agent for an alkyl ether sulfate (ES) composition.
式（１）において、Ｍ1はアルカリ金属またはＮＨ4を示す。Ｚは水素原子又はＳＯ3Ｍ2を示し、Ｍ2はアルカリ金属、ＮＨ4又は水素原子を示す。アルカリ金属としては、ナトリウム、カリウム、リチウムなどを例示することができるが、ナトリウム及びカリウムが好ましく、ナトリウムがより好ましい。 In the formula (1), M 1 represents an alkali metal or NH 4 . Z represents a hydrogen atom or SO 3 M 2 , and M 2 represents an alkali metal, NH 4 or a hydrogen atom. Examples of the alkali metal include sodium, potassium, and lithium. Sodium and potassium are preferable, and sodium is more preferable.
Ａ1で示される炭素数２〜４のアルキレン基は、直鎖、分岐鎖状のいずれであってもよく、例えばエチレン基、プロピレン基、１−メチルトリメチレン基、トリメチレン基、テトラメチレン基などを挙げることができるが、これらの中でエチレン基及びプロピレン基が好適である。 The alkylene group having 2 to 4 carbon atoms represented by A 1 may be either linear or branched, such as ethylene group, propylene group, 1-methyltrimethylene group, trimethylene group, tetramethylene group, etc. Among them, ethylene group and propylene group are preferable.
ｎは、平均値で１．０〜１２の数であり、−（Ａ1Ｏ）n−の分子量は１００〜５５０である。流動性能の点から、ｎが４〜１０であり、−（Ａ1Ｏ）n−の分子量が２００〜４００であるのが好ましく、ｎが５〜９であり、−（Ａ1Ｏ）n−の分子量が２５０〜３５０であるのがより好ましい。 n is a number of 1.0 to 12 on average, and the molecular weight of-(A 1 O) n- is 100 to 550. From the viewpoint of flow performance, n is 4 to 10, and the molecular weight of-(A 1 O) n- is preferably 200 to 400, n is 5 to 9, and-(A 1 O) n- It is more preferable that the molecular weight of is 250-350.
特に好ましい式（１）の化合物は、下記式（５）：
Ｍ2Ｏ3ＳＯ（ＣＨ2ＣＨ2Ｏ）pＳＯ3Ｍ1 （５）
で表されるアルキレンエーテルグリコールジ硫酸エステルのモノ塩及び／又はジ塩である。
式中、Ｍ1およびＭ2は前記と同様であり、−（ＣＨ2ＣＨ2Ｏ）p−の分子量は２００〜４００、好ましくは２５０〜３５０である。
Particularly preferred compounds of the formula (1) are those of the following formula (5):
M 2 O 3 SO (CH 2 CH 2 O) p SO 3 M 1 (5)
A mono- and / or di-salt of an alkylene ether glycol disulfate represented by
In the formula, M 1 and M 2 are the same as described above, and the molecular weight of — (CH 2 CH 2 O) p — is 200 to 400, preferably 250 to 350.
本発明のアニオン界面活性剤組成物は、Ａ成分として前記式（１）で表されるＡＥＧＳを１種以上、Ｂ成分として式（２）：
ＲＯ（Ａ2Ｏ）mＳＯ3Ｍ3 （２）
で表されるアルキルエーテルサルフェート（ＥＳ）を１種以上、および水を含む。
In the anionic surfactant composition of the present invention, one or more types of AEGS represented by the formula (1) are used as the A component, and the formula (2) is used as the B component:
RO (A 2 O) m SO 3 M 3 (2)
1 or more types of alkyl ether sulfate (ES) represented by these, and water.
式（２）において、Ｒは炭素数９〜２４、好ましくは炭素数１２〜２０の直鎖もしくは分岐鎖のアルキル基又はアルケニル基である。Ｒの炭素数が９〜２４であれば、得られるＥＳの、界面活性能及び水に対する溶解性のバランスが良好である。アルキル基及びアルケニル基は、直鎖、分岐鎖のいずれであってもよく、具体的には、デシル基、ドデシル基、テトラデシル基、ヘキサデシル基、オクタデシル基、イコシル基、ドコシル基、オレイル基（各置換基は、その異性体を含む）などが挙げられる。 In the formula (2), R is a linear or branched alkyl group or alkenyl group having 9 to 24 carbon atoms, preferably 12 to 20 carbon atoms. If the carbon number of R is 9 to 24, the resulting ES has a good balance of surface activity and solubility in water. The alkyl group and alkenyl group may be either straight chain or branched chain, and specifically, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, docosyl group, oleyl group (each Substituents include isomers thereof).
Ａ2で示される炭素数２〜４のアルキレン基は、直鎖、分岐鎖状のいずれであってもよく、例えばエチレン基、プロピレン基、１−メチルトリメチレン基、トリメチレン基、テトラメチレン基などを挙げることができるが、これらの中でエチレン基及びプロピレン基が好適である。Ａ2は、式（１）のＡ1と同一であってもよく、異なっていてもよい。 The alkylene group having 2 to 4 carbon atoms represented by A 2 may be linear or branched, such as ethylene group, propylene group, 1-methyltrimethylene group, trimethylene group, tetramethylene group, etc. Among them, ethylene group and propylene group are preferable. A 2 may be the same as or different from A 1 in formula (1).
Ｍ3は水素原子、アルカリ金属又はＮＨ4を表す。アルカリ金属としては、ナトリウム、カリウム、リチウムなどを例示することができるが、これらの中でナトリウム及びカリウムが好ましく、ナトリウムがより好ましい。 M 3 represents a hydrogen atom, an alkali metal or NH 4 . Examples of the alkali metal include sodium, potassium, and lithium. Among these, sodium and potassium are preferable, and sodium is more preferable.
ｍは、平均値で０〜１００の数であり、好ましくは０．１〜１００、より好ましくは０．５〜１０である。 m is an average value of 0 to 100, preferably 0.1 to 100, and more preferably 0.5 to 10.
アニオン界面活性剤組成物における式（１）のアニオン界面活性剤用添加剤の含有量は、ＥＳの種類や当該添加剤（ＡＥＧＳ）の種類に応じて異なるが、一般的には、ＡＥＧＳ総量として、ＥＳ総量１００質量部に対し、０．５〜１０質量部が好ましく、より好ましくは１〜１０質量部、特に好ましくは１〜５質量部である。このように、ＥＳに本発明のアニオン界面活性剤用添加剤を加えることにより、ＥＳを高濃度に含む組成物であっても良好な流動性を発揮し取扱い性がよい。 The content of the anionic surfactant additive of formula (1) in the anionic surfactant composition varies depending on the type of ES and the type of the additive (AEGS), but in general, as the total amount of AEGS The total amount of ES is preferably 0.5 to 10 parts by mass, more preferably 1 to 10 parts by mass, and particularly preferably 1 to 5 parts by mass. Thus, by adding the additive for an anionic surfactant of the present invention to ES, even a composition containing ES at a high concentration exhibits good fluidity and good handleability.
Ａ成分（式（１）のＡＥＧＳ）、Ｂ成分（式（２）のＥＳ）および水の合計に対するＡ成分、Ｂ成分および水の質量％の比は、１〜２０：５５〜９０：５〜４０が好ましく、１〜５：６５〜７５：１０〜３５がより好ましい。 The ratio of the mass ratio of the A component, the B component and the water to the sum of the A component (AEGS of the formula (1)), the B component (ES of the formula (2)) and water is 1-20: 55-90: 5. 40 is preferable, and 1-5: 65-75: 10-35 is more preferable.
アニオン界面活性剤組成物の製造方法に特に制限はないが、以下に示す方法に従えば、効率よく所望のアニオン界面活性剤組成物を製造することができる。すなわち、式（３）：
ＲＯ（Ａ2Ｏ）mＨ （３）
（式中、Ｒ、Ａ2及びｍは前記と同じである。）
で表される化合物（オキシアルキレンアルキルエーテル、ＡＥ）の１種以上と、式（４）：
ＨＯ（Ａ1Ｏ）nＨ （４）
（式中、Ａ1及びｎは前記と同じである。）
で表される化合物（アルキレンエーテルグリコール、ＡＥＧ）の１種以上との混合物（ＡＥ／ＡＥＧ混合物）を硫酸化し、次いで塩基性アルカリ金属化合物又はアンモニア水で中和処理することにより製造される。
Although there is no restriction | limiting in particular in the manufacturing method of an anionic surfactant composition, According to the method shown below, a desired anionic surfactant composition can be manufactured efficiently. That is, Formula (3):
RO (A 2 O) m H (3)
(In the formula, R, A 2 and m are the same as described above.)
One or more compounds represented by the formula (oxyalkylene alkyl ether, AE), and the formula (4):
HO (A 1 O) n H (4)
(In the formula, A 1 and n are the same as described above.)
A mixture (AE / AEG mixture) with one or more of the compounds represented by (alkylene ether glycol, AEG) is sulfated and then neutralized with a basic alkali metal compound or aqueous ammonia.
ＡＥ／ＡＥＧ混合物の調製方法に特に制限はなく、目的の混合物が得られる方法であれば、いかなる方法も用いることができる。ＡＥとＡＥＧの混合割合は、最終的に得られる式（１）で表されるＡＥＧＳと式（２）で表されるＥＳとの含有割合が上記した範囲になるように、適宜選定される。 The method for preparing the AE / AEG mixture is not particularly limited, and any method can be used as long as the target mixture can be obtained. The mixing ratio of AE and AEG is appropriately selected so that the content ratio of the AEGS represented by the formula (1) finally obtained and the ES represented by the formula (2) is in the above-described range.
ＡＥ／ＡＥＧ混合物を硫酸化するのに用いる硫酸化剤としては三酸化硫黄ガス、クロロスルホン酸などが挙げられるが、得られるアニオン界面活性剤組成物中の塩化物量をできるだけ少なくするために、三酸化硫黄ガスを用いることが好ましい。硫酸化の方法に特に制限はなく、常法にしたがって行うことができる。例えば、薄膜式連続反応装置を用いて、空気や窒素などの不活性ガスで希釈した、好ましくは濃度１〜３０容量％、より好ましくは１〜２０容量％の三酸化硫黄ガスを、ＡＥ／ＡＥＧ混合物に混合しＡＥとＡＥＧの硫酸化を行う。三酸化硫黄の濃度が１〜３０容量％の範囲であればガス容積が大きすぎることなく、また反応が過剰になるのを抑制することができる。 Examples of the sulfating agent used for sulfating the AE / AEG mixture include sulfur trioxide gas, chlorosulfonic acid, and the like. In order to minimize the amount of chloride in the resulting anionic surfactant composition, It is preferable to use sulfur oxide gas. There is no restriction | limiting in particular in the method of sulfation, It can carry out according to a conventional method. For example, using a thin film type continuous reaction apparatus, sulfur trioxide gas diluted with an inert gas such as air or nitrogen, preferably having a concentration of 1 to 30% by volume, more preferably 1 to 20% by volume, is added to AE / AEG. AE and AEG are sulfated by mixing with the mixture. If the concentration of sulfur trioxide is in the range of 1 to 30% by volume, the gas volume is not too large and the reaction can be prevented from becoming excessive.
三酸化硫黄の使用量は、通常、化学量論量×（０．９５〜１．０５）の範囲である。該三酸化硫黄の使用量が上記範囲であれば、起泡性を有しない未反応ＡＥ, ＡＥＧモノ硫酸エステルの量が少なく、かつ副生物である有臭成分（例えば低級アルデヒド、低級ケトン、環状エーテルなど）の生成量も少ない。好ましい量は、化学量論量×（０．９７〜１．０１）の範囲である。 The amount of sulfur trioxide used is usually in the range of stoichiometric amount × (0.95 to 1.05). If the amount of sulfur trioxide used is in the above range, the amount of unreacted AE, AEG monosulfate that does not have foaming properties is small, and odorous components that are by-products (for example, lower aldehyde, lower ketone, cyclic) The production amount of ether etc. is also small. A preferred amount is in the range of stoichiometric amount × (0.97 to 1.01).
反応装置に特に制限はないが、例えば槽型反応装置や薄膜式反応装置などを用いることができる。薄膜式反応装置としては、例えば流下薄膜式反応装置、上昇薄膜型反応装置及び管型気液混合相流反応装置などを用いることができる。製造効率の観点からは、薄膜式反応装置による連続式を適用することが好ましい。この薄膜式反応装置の中でも、反応効率及び着色などの観点から、流下薄膜式反応装置が好ましい。薄膜式反応装置を用いた場合の反応時間は、１０〜３００秒間程度である。 Although there is no restriction | limiting in particular in a reactor, For example, a tank type reactor, a thin film type reactor, etc. can be used. As the thin film reactor, for example, a falling thin film reactor, a rising thin film reactor, a tubular gas-liquid mixed phase flow reactor, and the like can be used. From the viewpoint of production efficiency, it is preferable to apply a continuous system using a thin film reactor. Among these thin film reactors, a falling film reactor is preferable from the viewpoint of reaction efficiency and coloring. The reaction time when using a thin film reactor is about 10 to 300 seconds.
硫酸化温度は、好ましくは１５〜７０℃、より好ましくは４０〜６０℃である。１５℃以上であれば流動性低下による局部的な反応過剰を抑制することができ、また７０℃以下にあれば生成物の分解を抑制することができる。 The sulfation temperature is preferably 15 to 70 ° C, more preferably 40 to 60 ° C. If it is 15 degreeC or more, the local excessive reaction by the fluid fall can be suppressed, and if it is 70 degreeC or less, decomposition | disassembly of a product can be suppressed.
上記のようにして得られた硫酸化物を含む混合物は、気／液分離を施し、次工程において中和処理される。中和処理は、例えば、塩基性アルカリ金属化合物の水溶液、好ましくは２０〜５０質量％水溶液、又はアンモニア水、好ましくは１０〜５０質量％のアンモニア水を用いて行う。前記塩基性アルカリ金属化合物としては、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、炭酸ナトリウム、炭酸カリウム、炭酸リチウムなどが例示され、水酸化ナトリウム及び炭酸ナトリウムが好ましい。 The mixture containing the sulfate obtained as described above is subjected to gas / liquid separation and neutralized in the next step. The neutralization treatment is performed using, for example, an aqueous solution of a basic alkali metal compound, preferably an aqueous solution of 20 to 50% by mass, or aqueous ammonia, preferably 10 to 50% by mass of aqueous ammonia. Examples of the basic alkali metal compound include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate and the like, and sodium hydroxide and sodium carbonate are preferable.
中和温度は、好ましくは２０〜８０℃、より好ましくは２０〜６０℃である。中和方式としては、例えば回分式中和、連続式中和などがあり、特に外部冷却装置を備えた連続循環中和方式が、中和温度を一定温度に保持し得る点からも好適に採用することができる。また、このようにして連続中和処理したのち、必要に応じ、回分操作又は連続操作で、さらにｐＨを微調整することもできる。上記のようにして得られた硫酸化物を含む混合物は、減圧条件下で気泡を取り除く。 The neutralization temperature is preferably 20 to 80 ° C, more preferably 20 to 60 ° C. Examples of neutralization methods include batch neutralization and continuous neutralization, and a continuous circulation neutralization method equipped with an external cooling device is particularly suitable because it can maintain the neutralization temperature at a constant temperature. can do. In addition, after continuous neutralization treatment in this way, the pH can be further finely adjusted by batch operation or continuous operation, if necessary. The mixture containing sulfate obtained as described above removes bubbles under reduced pressure.
上記の様にして、（Ａ）式（１）：
ＺＯ（Ａ1Ｏ）ｎＳＯ3Ｍ1 （１）
（式中、Ｍ1、Ｚ、Ａ1及びｎは前記と同じである。）
で表される化合物（ＡＥＧＳ）を１種以上、式（２）：
ＲＯ（Ａ2Ｏ）mＳＯ3Ｍ3 （２）
（式中、Ｒ、Ａ2、Ｍ3及びｍは前記と同じである。）
で表される化合物（ＥＳ）を１種以上、および水を含むアニオン界面活性剤組成物が得られる。
As described above, (A) Formula (1):
ZO (A 1 O) nSO 3 M 1 (1)
(In the formula, M 1 , Z, A 1 and n are the same as described above.)
One or more compounds (AEGS) represented by the formula (2):
RO (A 2 O) m SO 3 M 3 (2)
(In the formula, R, A 2 , M 3 and m are the same as described above.)
An anionic surfactant composition containing at least one compound (ES) represented by formula (II) and water is obtained.
本発明のアニオン界面活性剤組成物は、液体洗浄剤組成物に好適に用いることができる。この場合、該液体洗浄剤組成物には、必要に応じて色素、香料、可溶化剤、ビルダーなど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、カチオン界面活性剤、両性界面活性剤、アミド型非イオン界面活性剤などを添加することができる。液体洗浄剤組成物は、例えば、シャンプー、ボディシャンプー、台所用洗剤、リキッドソープなどに用いられる。 The anionic surfactant composition of the present invention can be suitably used for a liquid detergent composition. In this case, auxiliary agents such as pigments, fragrances, solubilizers, and builders can be appropriately added to the liquid detergent composition as necessary. Furthermore, for the purpose of adjusting detergency and foaming, other anionic surfactants, cationic surfactants, amphoteric surfactants, amide type nonionic surfactants and the like can be added. The liquid detergent composition is used for shampoos, body shampoos, kitchen detergents, liquid soaps, and the like.
合成例
炭素数１２／１４高級アルコールエトキシレート（酸化エチレンの平均付加モル数２．０）１００質量部に対して、表１に示した平均分子量のポリエチレングリコールを３質量部添加し、２０℃の水浴上でよく撹拌した。得られた混合物を薄膜式連続硫酸化設備を用いて、ＳＯ3ガスで硫酸化後（硫酸化設備の冷却水温度５３℃、３０秒間）、２６質量％水酸化ナトリウム水溶液中に投入し、中和を行い、減圧下で気泡を除去し、表１に示す分析値を有する各アニオン界面活性剤水溶液が得られた。
Synthesis Example 3 parts by mass of polyethylene glycol having an average molecular weight shown in Table 1 was added to 100 parts by mass of a 12/14 higher alcohol ethoxylate having a carbon number of 12/14 (average number of moles of ethylene oxide added 2.0). Stir well on a water bath. The obtained mixture was sulfated with SO 3 gas using a thin film type continuous sulfation facility (cooling water temperature of sulfation facility 53 ° C., 30 seconds) and then poured into a 26 mass% sodium hydroxide aqueous solution. Summing was performed and air bubbles were removed under reduced pressure to obtain each anionic surfactant aqueous solution having analytical values shown in Table 1.
実施例１〜３、比較例１〜２
合成例によって得られた各アニオン界面活性剤水溶液の流動性を以下に示す方法で評価した。すなわち鉛直に立てた内径１０ｍｍの円柱状のガラス管に試料水溶液を１５ｍＬ仕込み、上部に詮をして８℃で充分静置した。静置後、栓をはずして試料の下端が１０ｃｍ移動するのに要した時間を流動性の指標とした。
Examples 1-3, Comparative Examples 1-2
The fluidity of each anionic surfactant aqueous solution obtained by the synthesis example was evaluated by the following method. That is, 15 mL of the sample aqueous solution was charged in a cylindrical glass tube with an inner diameter of 10 mm which was set up vertically, and the upper portion was covered with a jar and allowed to stand still at 8 ° C. After standing, the time required for removing the stopper and moving the lower end of the sample by 10 cm was used as an indicator of fluidity.
Claims (3)
式（１）：
ＺＯ（Ａ 1 Ｏ） n ＳＯ 3 Ｍ 1 （１）
（式中、Ｍ 1 はアルカリ金属またはＮＨ 4 を示し、Ｚは水素原子又はＳＯ 3 Ｍ 2 （式中、Ｍ 2 はアルカリ金属、ＮＨ 4 又は水素原子を示す）を示し、Ａ 1 は炭素数２〜４のアルキレン基、ｎは平均値で１．０〜１２の数を示し、−（Ａ 1 Ｏ） n −の分子量は１００〜５５０である）
式（２）：
ＲＯ（Ａ2Ｏ）mＳＯ3Ｍ3 （２）
（式中、Ｒは炭素数９〜２４の直鎖のアルキル基又はアルケニル基、Ａ2は炭素数２〜４のアルキレン基、Ｍ3は水素原子、アルカリ金属又はＮＨ4、ｍは平均値で０．１〜１００の数を示す） A component which consists of 1 or more types of the compound represented by Formula (1), B component which consists of 1 or more types of the compound represented by Formula (2), and water, A component, B component, and water Anionic surfactant composition containing 65 to 90% by mass of component B with respect to the total of
Formula (1):
ZO (A 1 O) n SO 3 M 1 (1)
(In the formula, M 1 represents an alkali metal or NH 4 , Z represents a hydrogen atom or SO 3 M 2 (wherein M 2 represents an alkali metal, NH 4 or a hydrogen atom), and A 1 represents the number of carbon atoms. 2 to 4 alkylene groups, n represents an average number of 1.0 to 12, and the molecular weight of — (A 1 O) n — is 100 to 550)
Formula (2):
RO (A 2 O) m SO 3 M 3 (2)
(Wherein, R represents an alkyl or alkenyl group having a straight chain of 9-24 carbon atoms, A 2 is an alkylene group having 2 to 4 carbon atoms, M 3 is a hydrogen atom, an alkali metal or NH 4, m is an average value Indicates a number from 0.1 to 100 )
ＲＯ（Ａ2Ｏ）mＨ （３）
（式中、Ｒは炭素数９〜２４の直鎖のアルキル基またはアルケニル基、Ａ2は炭素数２〜４のアルキレン基、ｍは平均値で０．１〜１００の数を示す）
で表される化合物の１種以上と、式（４）：
ＨＯ（Ａ1Ｏ）nＨ （４）
（式中、Ａ1は炭素数２〜４のアルキレン基、ｎは平均値で１．０〜１２の数を示し、−（Ａ1Ｏ）n−の分子量は１００〜５５０である。）
で表される化合物の１種以上との混合物を硫酸化し、次いで塩基性アルカリ金属化合物又はアンモニア水で中和処理する工程を含む、請求項１又は２に記載のアニオン界面活性剤組成物の製造方法。 Formula (3):
RO (A 2 O) m H (3)
(Wherein, R is a number of from 0.1 to 100 in a straight-chain alkyl or alkenyl group, A 2 represents an alkylene group having 2 to 4 carbon atoms, m is an average of 9 to 24 carbon atoms)
At least one compound represented by formula (4):
HO (A 1 O) n H (4)
(In the formula, A 1 represents an alkylene group having 2 to 4 carbon atoms, n represents an average value of 1.0 to 12, and — (A 1 O) n — has a molecular weight of 100 to 550.)
The manufacturing of the anionic surfactant composition of Claim 1 or 2 including the process of sulfating the mixture with 1 or more types of the compound represented by these, and then neutralizing with a basic alkali metal compound or ammonia water. Method.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5636596A (en) * | 1979-09-01 | 1981-04-09 | Henkel Kgaa | Concentrated aqueous solution of surfactant and improvement of flowability thereof |
| JPS5665098A (en) * | 1979-10-31 | 1981-06-02 | Lion Corp | High concentration surfactant slurry |
| JPH05140586A (en) * | 1991-03-19 | 1993-06-08 | Shell Internatl Res Maatschappij Bv | Water-base liquid concentrated alkyl sulfate composition |
| JP2002256286A (en) * | 2001-03-05 | 2002-09-11 | Kao Corp | Liquid cleanser composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5636596A (en) * | 1979-09-01 | 1981-04-09 | Henkel Kgaa | Concentrated aqueous solution of surfactant and improvement of flowability thereof |
| JPS5665098A (en) * | 1979-10-31 | 1981-06-02 | Lion Corp | High concentration surfactant slurry |
| JPH05140586A (en) * | 1991-03-19 | 1993-06-08 | Shell Internatl Res Maatschappij Bv | Water-base liquid concentrated alkyl sulfate composition |
| JP2002256286A (en) * | 2001-03-05 | 2002-09-11 | Kao Corp | Liquid cleanser composition |
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