JPH0251597A - Liquid detergent composition - Google Patents
Liquid detergent compositionInfo
- Publication number
- JPH0251597A JPH0251597A JP20151388A JP20151388A JPH0251597A JP H0251597 A JPH0251597 A JP H0251597A JP 20151388 A JP20151388 A JP 20151388A JP 20151388 A JP20151388 A JP 20151388A JP H0251597 A JPH0251597 A JP H0251597A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- detergent composition
- liquid detergent
- formula
- acylaspartate
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 239000007788 liquid Substances 0.000 title claims abstract description 7
- 239000003599 detergent Substances 0.000 title abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 238000004140 cleaning Methods 0.000 claims description 10
- -1 alkyl betaine Chemical compound 0.000 claims description 9
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229960003237 betaine Drugs 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000005187 foaming Methods 0.000 abstract description 8
- 239000003085 diluting agent Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract 2
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- DVEKCXOJTLDBFE-UHFFFAOYSA-O carboxymethyl-dodecyl-dimethylazanium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC(O)=O DVEKCXOJTLDBFE-UHFFFAOYSA-O 0.000 abstract 1
- IEXXLSKKBWIDAC-ZOWNYOTGSA-M sodium;(3s)-3-(dodecanoylamino)-4-hydroxy-4-oxobutanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CC(O)=O IEXXLSKKBWIDAC-ZOWNYOTGSA-M 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000002253 acid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- VCRXMSMANOGRCM-UHFFFAOYSA-N 2-(dodecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CC(O)=O VCRXMSMANOGRCM-UHFFFAOYSA-N 0.000 description 1
- MLOYYKYQLFOZOE-UHFFFAOYSA-N 2-(tetradecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCCCC(=O)NC(C(O)=O)CC(O)=O MLOYYKYQLFOZOE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 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
- 239000003752 hydrotrope Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940074096 monoolein Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規な洗浄剤組成物に関する。更に詳細には、
皮膚に、対して温和な作用を有し、しかも優れた洗浄力
、起泡力を有する液体洗浄剤組成物に関するものである
。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel cleaning composition. More specifically,
The present invention relates to a liquid detergent composition that has a mild effect on the skin and has excellent detergency and foaming power.
従来１台所用食器洗浄剤、シャンプー、ボディーシャン
プーの主成分は、アルキル硫酸エステル塩又はアルキル
エーテル硫酸塩であった。ところが、これらは皮膚刺激
性があり、また臭気の点でも皮膚洗浄剤の基剤としては
不満足であった。そこで近年Ｎ−アシルグルタミン酸塩
を配合した皮膚に温和な洗浄剤組成物が洗顔用固形石け
ん、あるいは頭髪用シャンプー、又はボディーシャンプ
ーに使用される傾向にある。Conventionally, the main ingredients of kitchen dishwashing agents, shampoos, and body shampoos have been alkyl sulfate ester salts or alkyl ether sulfates. However, these were unsatisfactory as bases for skin cleansers due to skin irritation and odor. Therefore, in recent years, there has been a trend for skin-friendly cleansing compositions containing N-acylglutamate to be used in bar soaps for facial cleansing, hair shampoos, and body shampoos.
一般にＮ−アシルアミノ酸は皮膚に対して温和であるば
かりでなく、皮膚病の原因となる有害な微生物の繁殖を
抑制する動きがあり、感染性の皮膚炎の予防には効果が
あるとされている。In general, N-acyl amino acids are not only gentle on the skin, but also have the ability to inhibit the growth of harmful microorganisms that cause skin diseases, and are said to be effective in preventing infectious dermatitis. There is.
Ｎ−アシルグルタミン酸塩は皮膚に直接接触する界面活
性剤として優れた性能は有するものの油汚垢存在時に於
ける起泡力・洗浄力がアルキルエーテル硫酸塩やアルキ
ル硫酸塩に比較してはるか・Ｋ劣り、更に単一組成では
常温（２０〜３０℃）付近に於ける溶解度が著しく低い
為、第３級アミンオキサイドとの併用（特開昭４８−３
３９６４号公報）やベタインとの併用（特公昭５０−２
３６８２号公報）等が提案されている。しかるに、従来
から７ヤンプーの主剤として多く使用されているアルキ
ルエーテル硫酸塩に比較すると、油汚垢存在時の起泡力
や洗浄力が未だ不十分である。Although N-acylglutamate has excellent performance as a surfactant that comes into direct contact with the skin, its foaming and cleaning power in the presence of oil stains is far inferior to that of alkyl ether sulfates and alkyl sulfates. Furthermore, since the solubility of a single composition at room temperature (20 to 30°C) is extremely low, the combination with tertiary amine oxide (JP-A-48-3
Publication No. 3964) or in combination with betaine (Special Publication No. 50-2
3682) etc. have been proposed. However, compared to alkyl ether sulfates, which have conventionally been widely used as the main ingredient in 7 Yanpu, the foaming power and cleaning power in the presence of oil stains are still insufficient.
本発明者らは、前記問題点を解決するために種種検討の
結果、Ｎ−アシルアスパラギン酸塩とベタインとを併用
することにより、その目的を達成することができた。The present inventors conducted various studies to solve the above-mentioned problems, and as a result, they were able to achieve the objective by using N-acylaspartate and betaine in combination.
即ち、本発明は、下記一般式（１）で表わされるＮ−ア
シルアスパラギン酸塩と下記一般式（２）で表わされる
アルキルベタインとを含有してなる液体洗浄剤組成物を
提供するものである。That is, the present invention provides a liquid detergent composition containing an N-acylaspartate represented by the following general formula (1) and an alkyl betaine represented by the following general formula (2). .
ＲＣＯ−ＮＨ−ＣＨＣＯＯＭｌ
ＣＨ２Ｃ００Ｍ２ （１）（式中、Ｒは炭
素数７ないし２１のアルキル基またはアルケニル基、Ｍ
ｌおよびＭ２は水素またはＮｕ。RCO-NH-CHCOOMl CH2C00M2 (1) (wherein, R is an alkyl group or alkenyl group having 7 to 21 carbon atoms, M
1 and M2 are hydrogen or Nu.
Ｋ、ＮＨ４もしくはアルカノールアミンから誘導される
カチオンである。）
（式中、Ｒ１は炭素数ＩＯないし１８のアルキル基又は
、アルケニル基、Ｒ２およびＲ３は炭素数１ないし３の
アルキル基である。）
本発明の洗浄剤組成物において用いられる式（１）で表
わされるＮ−アシルアスパラギン酸塩は、Ｎ−アシル−
Ｌ−アスパラギン酸塩またはＮ−アシル−Ｄ−アスノＪ
？ラギン酸塩または両者の混合物であり１例えばアスパ
ラギン酸と炭素数８ないし２２の脂肪酸ハライドとを塩
基性触媒の存在下に反応させること罠より製造される。It is a cation derived from K, NH4 or alkanolamine. ) (In the formula, R1 is an alkyl group having IO to 18 carbon atoms or an alkenyl group, and R2 and R3 are an alkyl group having 1 to 3 carbon atoms.) Formula (1) used in the cleaning composition of the present invention N-acylaspartate represented by N-acyl-
L-aspartate or N-acyl-D-asuno J
? It is a laginate salt or a mixture of both, and is produced, for example, by reacting aspartic acid with a fatty acid halide having 8 to 22 carbon atoms in the presence of a basic catalyst.
具体的には、Ｎ−ラウロイルアスパラギン酸。Specifically, N-lauroyl aspartic acid.
Ｎ−ミリストイルアスパラギン酸 ｐＪ −／＃ルミト
イルアス／母ラうン酸、Ｎ−ステアロイルアスハラギン
酸、Ｎ−オレオイルアスノセラギン酸、およびＮ−ココ
イルアスノセラギン酸、またはそれらの酸のナトリウム
、カリウム、アンモニウム、モノエタノールアンモニウ
ム、ソエタノールアンモニウムまたはトリエタノールア
ンモニウム塩などが挙げられる。N-myristoylaspartic acid pJ -/#lumitoylas/mother launic acid, N-stearoyl asharagic acid, N-oleoylasunoselagic acid, and N-cocoyl asnoceragic acid, or sodium and potassium of these acids , ammonium, monoethanolammonium, soethanolammonium or triethanolammonium salts.
本発明の洗浄剤組成物において用いられるもう一つの成
分であるアルキルベタインは前記一般式（２）で表わさ
れる化合物である。具体的には１例えば、ツメチルラウ
リルベタイン、ノメチルミリスチルペタイ／、ツメチル
ステアリルベタイン、ツメチルオレイルベタイン、メチ
ルエチルラウリルベタイン、メチルｎプロピルラウリル
ペタイアなどが挙げられる。The alkyl betaine, which is another component used in the cleaning composition of the present invention, is a compound represented by the above general formula (2). Specific examples include trimethyllaurylbetaine, nomethylmyristylpetai, trimethylstearylbetaine, trimethyloleylbetaine, methylethyllaurylbetaine, and methyl n-propyllaurylpetai.
Ｎ−アシルアスフ９ラギン酸塩とアルキルベタインの配
合比が１＝５から５：１の範囲において。The blending ratio of N-acylasuph-9raginate and alkyl betaine is in the range of 1=5 to 5:1.
特てすぐれた性能を示すが、両者がわ・ずがでも併用さ
れていると相乗効果が認められる。It shows particularly excellent performance, but a synergistic effect is observed when both are used together.
本発明の洗浄剤組成物は、皮膚に対してマイルドであり
かつ油汚垢存在時にも優れた起泡力を有し、著しい油汚
れに対しても優れた洗浄力を有するものである。The detergent composition of the present invention is mild to the skin, has excellent foaming power even in the presence of oil stains, and has excellent detergency even against significant oil stains.
本発明の洗浄剤組成物は、任意に通常の補助剤。The cleaning compositions of the invention optionally contain conventional auxiliaries.
希釈剤、増量剤、ビルダー等１例えばハイドロトロープ
、香料、染料、螢光染料、無機または有機のビルダーを
含むことができる。Diluents, fillers, builders and the like may be included, such as hydrotropes, perfumes, dyes, fluorescent dyes, inorganic or organic builders.
次に本発明を実施例をもって説明するが１本発明はこれ
らの実施例に限定されるものではない。Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.
表１に示す洗浄剤組成物について洗浄力および起泡力の
各評価を行い、結果を表１に示した。但し１表中組成物
の各成分の配合ｆｅ示す数字の単位はすべて重量百分率
である。The detergent compositions shown in Table 1 were evaluated for detergency and foaming power, and the results are shown in Table 1. However, in Table 1, the units of numbers showing the formulation of each component of the composition are all percentages by weight.
尚、各特性の評価は１次に示す評価法に従って行った。In addition, evaluation of each characteristic was performed according to the evaluation method shown in the first order.
（１）起泡力
液体洗浄剤組成物を蒸留水で２００倍に希釈した水溶液
２０ｄ、油成分としてトリオレインＩＩｉを共栓付き１
０（Ｉ＋／メスシリンダーに入れ、共栓をして激しく上
下に２０回振とうし、直ちに共栓を外して水平な場所に
メスシリング−を静置し、泡の容量を目盛りから読みと
り、これを起泡力とする。(1) Foaming power 20d aqueous solution prepared by diluting the liquid detergent composition 200 times with distilled water, containing triolein IIi as the oil component and 1 with a stopper.
0 (I+/Put it in a graduated cylinder, close the stopper, and shake vigorously up and down 20 times. Immediately remove the stopper and leave the graduated cylinder - on a horizontal surface. Read the volume of foam from the scale. It has foaming power.
（２）洗浄力評価
スライドグラスを油脂クロロホルム溶液（牛脂と大豆油
の等量混合物２０ｇ、モノオレイン０．２５Ｉ、オイル
レッド０．１ｇをクロロホルム６０ｍ／に溶解する）に
１〜２秒間浸漬し、油脂成分を付着させ、風乾後リーナ
ッツ改良洗浄力試験器を用いて、２００倍に希釈した洗
浄剤組成物水溶液で。(2) Detergency evaluation A slide glass is immersed for 1 to 2 seconds in an oil/fat chloroform solution (20 g of an equal mixture of beef tallow and soybean oil, 0.25 I of monoolein, and 0.1 g of Oil Red are dissolved in 60 m/chloroform). After attaching oil and fat components and air-drying, using a Leanuts improved detergency tester, a 200-fold diluted detergent composition aqueous solution was used.
３分間、３０℃にて洗浄し油脂成分の除去率を下式から
算出して洗浄力（支））とする。Wash for 3 minutes at 30°C, and the removal rate of oil and fat components is calculated from the following formula and used as the cleaning power (support).
Ｗ３：洗浄前の油脂成分付着量ｒ＆） Ｗｗ：洗浄後の油脂成分付着ｆｃ９）W3: Amount of oil and fat components attached before cleaning r&) Ww: Oil and fat component adhesion after cleaning fc9)
Claims (1)
酸塩と下記一般式（２）で表わされるアルキルベタイン
とを含有してなる液体洗浄剤組成物。 ▲数式、化学式、表等があります▼（１） （式中、Ｒは炭素数７ないし２１のアルキル基またはア
ルケニル基、Ｍ＿１およびＭ＿２は水素またはＮａ、Ｋ
、ＮＨ＿４もしくはアルカノールアミンから誘導される
カチオンである。） ▲数式、化学式、表等があります▼（２） （式中、Ｒ＿１は炭素数１０ないし１８のアルキル基又
はアルケニル基、Ｒ＿２およびＲ＿３は炭素数１ないし
３のアルキル基である。）[Scope of Claims] A liquid cleaning composition comprising an N-acylaspartate represented by the following general formula (1) and an alkyl betaine represented by the following general formula (2). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R is an alkyl group or alkenyl group having 7 to 21 carbon atoms, M_1 and M_2 are hydrogen, Na, K
, NH_4 or a cation derived from an alkanolamine. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (In the formula, R_1 is an alkyl group or alkenyl group having 10 to 18 carbon atoms, and R_2 and R_3 are alkyl groups having 1 to 3 carbon atoms.)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20151388A JP2507546B2 (en) | 1988-08-12 | 1988-08-12 | Liquid detergent composition |
| US07/390,211 US5000877A (en) | 1988-08-12 | 1989-08-07 | Aqueous liquid detergent containing an N-acylaspartate and a betaine or imidazoline surfactant |
| DE89114830T DE68910617T2 (en) | 1988-08-12 | 1989-08-10 | Liquid detergent. |
| EP89114830A EP0356784B1 (en) | 1988-08-12 | 1989-08-10 | Liquid detergent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20151388A JP2507546B2 (en) | 1988-08-12 | 1988-08-12 | Liquid detergent composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0251597A true JPH0251597A (en) | 1990-02-21 |
| JP2507546B2 JP2507546B2 (en) | 1996-06-12 |
Family
ID=16442290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20151388A Expired - Fee Related JP2507546B2 (en) | 1988-08-12 | 1988-08-12 | Liquid detergent composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2507546B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0423896A (en) * | 1990-05-18 | 1992-01-28 | Kanebo Ltd | Low-irritation detergent composition |
| JP2014005230A (en) * | 2012-06-22 | 2014-01-16 | Kao Corp | Liquid cleaning composition |
-
1988
- 1988-08-12 JP JP20151388A patent/JP2507546B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0423896A (en) * | 1990-05-18 | 1992-01-28 | Kanebo Ltd | Low-irritation detergent composition |
| JP2014005230A (en) * | 2012-06-22 | 2014-01-16 | Kao Corp | Liquid cleaning composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2507546B2 (en) | 1996-06-12 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |