US3663459A - Detergent bar - Google Patents
Detergent bar Download PDFInfo
- Publication number
- US3663459A US3663459A US14202A US3663459DA US3663459A US 3663459 A US3663459 A US 3663459A US 14202 A US14202 A US 14202A US 3663459D A US3663459D A US 3663459DA US 3663459 A US3663459 A US 3663459A
- Authority
- US
- United States
- Prior art keywords
- water
- milled
- acyl
- parts
- bar
- 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
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- 239000003599 detergent Substances 0.000 title abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 33
- 239000002253 acid Substances 0.000 abstract description 11
- 239000000344 soap Substances 0.000 abstract description 11
- 150000001413 amino acids Chemical class 0.000 abstract description 8
- 239000004220 glutamic acid Substances 0.000 abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 abstract description 4
- 150000004671 saturated fatty acids Chemical class 0.000 abstract description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 235000003441 saturated fatty acids Nutrition 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 125000002252 acyl group Chemical group 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 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 4
- 239000000654 additive Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- -1 pentadecanoyl Chemical group 0.000 description 4
- 230000002633 protecting effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 229960002989 glutamic acid Drugs 0.000 description 3
- 239000008233 hard water Substances 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 125000001176 L-lysyl group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])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 2
- 239000004571 lime Substances 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000013042 solid detergent Substances 0.000 description 2
- AVBJHQDHVYGQLS-UHFFFAOYSA-N 2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 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
- 239000005639 Lauric acid Substances 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000002585 base Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000003074 decanoyl 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(*)=O 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 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
- 239000002304 perfume Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000003009 skin protective agent Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- IWIUXJGIDSGWDN-PFEQFJNWSA-M sodium;(2r)-2-(dodecanoylamino)-5-hydroxy-5-oxopentanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-PFEQFJNWSA-M 0.000 description 1
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 description 1
- IWIUXJGIDSGWDN-UHFFFAOYSA-M sodium;2-(dodecanoylamino)-5-hydroxy-5-oxopentanoate Chemical compound [Na+].CCCCCCCCCCCC(=O)NC(C(O)=O)CCC([O-])=O IWIUXJGIDSGWDN-UHFFFAOYSA-M 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel 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
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
Definitions
- the present invention relates to detergents, and particularly to a detergent bar for toilet use.
- the synthetic detergent bar has inferior touch to the skin and inferior performance as compared with ordinary bar soap.
- the invention aims at providing a detergent bar which has good hardness and such solubility that it does not readily disintegrate when immersed in water at 40 C., good foaming power and detergency in soft and hard Water, a gentle effect on the skin, and a comfortable touch during use, and which leaves the skin soft and smooth.
- the detergent bars of the invention are prepared by molding mono-salts of N-acyl derivatives of acidic amino acids having an acyl group of 8 to 22 carbon atoms together with an amount of water sufficient to make a shaperetaining body.
- N-acylamino acids or their salts have been known to have surface activity and antibacterial effects, and sodium N-aluroyl-sarcosinate has been used therefore in detergents, and such cosmetics as toothpaste.
- the salts of N-acylamino acids have also been used in heavy duty detergents as minor additives to improve performance. They have never been used as the principal components of a shaped, solid detergent body.
- the acidic amino acids whose N-acyl derivative salts are the detergent materials of this invention are glutamic acid and aspartic acid.
- the acyl groups are those of saturated or unsaturated fatty acids having 8 to 22 carbon atoms, such as lauroyl, decanoyl, myristyl, pentadecanoyl, palmityl, margaryl, stearyl, oleyl, and radicals of naturally occurring mixed fatty acids derived from coconut oil, tallow oil, hydrogenated tallow oil, olive oil, soybeans, and corn.
- the amino acid component may be in the optically active form or the racemic form.
- Suitable salts are the alkali metal salts such as those of sodium and potassium, the ammonium salts, salts of basic amino acids such as lysine, ornithine, or arginine, and other water-soluble amine salts.
- the N-acylamino acid salts may be used as the active detergent material singly or combined, and adjuvant materials such as thickeners, perfumes, pigments, dyes, and the like may be added. Examples of such adjuvants are higher fatty acid amides, salts of N-acyl derivatives of neutral amino acids, alkylene oxide condensates, alcohol, glycerol, and glycerides.
- the detergent bars of the invention are prepared by milling the salts of the N-acylamino acids with or without the adjuvants and with a suitable amount of water, extruding the milled material into a bar, and molding the extruded material in a conventional manner.
- a dry salt of the N-acylamino acid is first mixed with a suitable amount of water and other additives.
- the water facilitates milling and makes the detergent moldable so that the bar does not disintegrate in water.
- the proportion of water may be varied depending on the salt and the adjuvants used, it is usually less than 40%, and preferably 3 to 20% of the weight of the solid materials in the composition.
- a small rolling mill having three stainless steel rollers of 12 cm. diameter and rotating at 16, 32 and 64 r.p.m. respectively may be used.
- the mixture is passed through the mill 2 to 10 times. It is then extruded into a bar from an extruder having a heated jacket, and the bar is molded in a press.
- the shaped detergent composition so obtained has a solubility value, as determined by a rubbing test, equal to that of toilet soap meeting the Japanese Industrial Standards K-3301, and thus dissolves only moderately in water during use. It has good shape-retaining properties and a soft touch after use like that of toilet soap. It has a pH of 5-7 during use, and this is near the isoelectric point of protein in the surface of the human skin.
- the composition is stable in hard water, mild to the skin, and makes the skin soft and smooth after use. It has antibacterial elfects and disinfects the skin.
- EXAMPLE 1 parts monosodium N-acyl-DL-glutamate, whose acyl groups were those of coconut oil fatty acid, and 5 parts water were milled on a small rolling mill and then extruded into a bar from a small plodder whose nozzle temperature was kept at 55 C. The bar was shaped on a press.
- the solubility value of the product according to the rubbing test of the Japanese Industrial Standards K4304- 1956 was 55 (40 C., 10 minutes). It had good foaming power and detergency, caused almost no skin irritation, and left the skin soft and smooth feeling.
- EXAMPLE 2 A mixture of 70 parts monosodium N-lauroyl-D-glutamate, 5 parts of the triethanolamine salt of Nlauroyl- L-glutamic acid, and 3 parts water was milled, extruded at a nozzle temperature of 60 C. from a small plodder, and formed into shaped pieces on a press.
- EXAMPLE 3 A mixture of 50 parts monosodium N-lauroyl-L-glutamate, 50 parts of the L-lysine salt of N-lauroyLL-glutamic acid, and 10 parts water was milled and further processed as in Example 1.
- the solubility value of the product was 65. It did not disintegrate when immersed in water at 40 C. and showed good detergency.
- EXAMPLE 4 100 parts of the L-lysine salt of N-lauroyl-DL-glutamic acid and 5 parts water were mixed, milled, and further processed as in Example 1.
- the product had a solubility value of 95, good detergency, and skin protecting properties.
- EXAMPLE 5 80 parts monosodium N-lauroyl-DL-glutamate, 15 parts of N methyl N lauroyl B alanine sodium, 2 parts polyethyleneglycol (M.W. 400), and 5 parts water were milled and converted to a detergent bar as in Example 1.
- the solubility of this product was 64. It had good detergency, and excellent protective properties for the skin.
- EXAMPLE 6 5 parts water were added to 100 parts of a monosodium N-acyl-DL-glutamate prepared by reacting DL-glutamic acid with mixed fatty acid chlorides derived in a. ratio of 20:30:50 from beef tallow oil fatty acids, coconut oil fatty acids, and lauric acid, and neutralizing the reaction product with sodium hydroxide.
- the aqueous solution of the acylation product had a pH of 5.5.
- the mixture of water and N-acylglutamic acid was milled and further processed as in Example 1.
- the detergent bar obtained had a solubility value of 50, showed good detergency, and gave a soft and smooth feeling to the skin after use.
- EXAMPLE 7 100 parts monoammonium N-lauroyl-L-glutamate were added to 7 parts water, and the mixture was milled and further processed as in Example 1.
- the detergent bar so produced had a solubility value of 75, gOOd detergency, and skin protecting properties.
- EXAMPLE 8 Detergent bars were prepared by the method of Example 1 from the following four compositions:
- Foam performance was evaluated as the foam height in centimeters estimated according to Japanese Industrial Standards K-3362-1955 for a 0.25% solution in water at 40 C.
- the wettability values were estimated by measuring the falling time (seconds) of a 0.25% solution at 40 C. according to the canvas wetting method.
- the lime soap dispersing power was determined for a 0.25% solution by the test described in the Journal of The American Oil Chemists Society [27 (1950) Relative surface tension was determined in a 0.25 solution at 40 C. by means of a Du Nouy tensiometer.
- the solubility value of the detergent bar was 78. It had good detergency and skin protecting properties.
- EXAMPLE 11 For comparison purposes, 10 parts water and 100 parts sodium N-lauroylsarcosinate were milled and compressed as in Example 1 to prepare a detergent bar. The bar was very hard and had many cracks. It disintegrated rapidly when immersed in warm water.
- a detergent bar consisting essentially of a water soluble, milled, mono-salt of an N-acylglutamic acid or N-acylaspartic acid having detergent properties, the acyl group of said acid being the acyl radical of a saturated or unsaturated fatty acid having 8 to 22 carbon atoms, and the cationic moiety of said mono-salt is selected from the group consisting of sodium, potassium, ammonium, lysine, ornithine, and lower alkanolamine.
- a method of making a shaped solid detergent bar which comprises milling a mixture of water and of a water, soluble mono-salt of an N-acylglutamic acid or N-acylaspartic acid, and compacting the milled mixture into a shape retaining solid bar, the amount of said water being suflicient to facilitate said compacting so that said bar does not disintegrate when immersed in Water at 40 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44017040A JPS4811805B1 (enrdf_load_stackoverflow) | 1969-03-07 | 1969-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3663459A true US3663459A (en) | 1972-05-16 |
Family
ID=11932871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14202A Expired - Lifetime US3663459A (en) | 1969-03-07 | 1970-02-25 | Detergent bar |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3663459A (enrdf_load_stackoverflow) |
| JP (1) | JPS4811805B1 (enrdf_load_stackoverflow) |
| CA (1) | CA927840A (enrdf_load_stackoverflow) |
| DE (1) | DE2010303C3 (enrdf_load_stackoverflow) |
| ES (1) | ES377173A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2037778A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1261322A (enrdf_load_stackoverflow) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5046745A (enrdf_load_stackoverflow) * | 1973-08-08 | 1975-04-25 | ||
| US3975313A (en) * | 1974-06-19 | 1976-08-17 | Shelmire Jr Jesse Bedford | Solid amphoteric skin cleanser |
| US4046717A (en) * | 1972-01-28 | 1977-09-06 | Lever Brothers Company | Detergent bars |
| US4073756A (en) * | 1976-04-26 | 1978-02-14 | Konishi Co., Ltd. | Solid adhesive compositions |
| US4075830A (en) * | 1976-04-26 | 1978-02-28 | Konishi Co., Ltd. | Solid adhesive compositions |
| US4273684A (en) * | 1979-05-03 | 1981-06-16 | Ajinomoto Co., Inc. | Transparent detergent bar |
| US4303543A (en) * | 1979-02-27 | 1981-12-01 | The Procter & Gamble Company | Method for cleansing and conditioning the skin |
| US4749515A (en) * | 1985-11-06 | 1988-06-07 | Lion Corporation | Liquid detergent composition |
| US5000877A (en) * | 1988-08-12 | 1991-03-19 | Mitsubishi Petrochemical Co., Ltd. | Aqueous liquid detergent containing an N-acylaspartate and a betaine or imidazoline surfactant |
| US5098608A (en) * | 1989-09-29 | 1992-03-24 | Shiseido Company Ltd. | Transparent solid detergent compositions containing n-acyl acidic amino acid salts |
| US5326493A (en) * | 1991-12-04 | 1994-07-05 | Kao Corporation | Solid detergent composition based on N-acyl sodium salt |
| US5518665A (en) * | 1993-01-11 | 1996-05-21 | Ajinomoto Co., Inc. | Transparent solid detergents |
| US6288023B1 (en) | 1995-07-12 | 2001-09-11 | Kyowa Hakko Kogyo, Co., Ltd. | Cleansing compositions comprising N-acylamino acids |
| US20090149370A1 (en) * | 2007-12-06 | 2009-06-11 | Conopco, Inc., D/B/A Unilever | Transparent Cleansing Bar |
| JP2015221762A (ja) * | 2014-05-23 | 2015-12-10 | 川研ファインケミカル株式会社 | 毛髪も含めた全身用固形洗浄剤組成物 |
| WO2017075329A2 (en) | 2015-10-29 | 2017-05-04 | Dana-Farber Cancer Institute, Inc. | Methods for identification, assessment, prevention, and treatment of metabolic disorders using pm20d1 and n-lipidated amino acids |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5315084B2 (enrdf_load_stackoverflow) * | 1972-09-01 | 1978-05-22 | ||
| FR2426082A1 (fr) * | 1978-05-18 | 1979-12-14 | Hokko Yushi Co Ltd | Composition detergente formant un enduit ou revetement pharmaceutiquement efficace sur la peau |
-
1969
- 1969-03-07 JP JP44017040A patent/JPS4811805B1/ja active Pending
-
1970
- 1970-02-25 US US14202A patent/US3663459A/en not_active Expired - Lifetime
- 1970-03-05 ES ES377173A patent/ES377173A1/es not_active Expired
- 1970-03-05 DE DE2010303A patent/DE2010303C3/de not_active Expired
- 1970-03-06 FR FR7008221A patent/FR2037778A5/fr not_active Expired
- 1970-03-06 GB GB00983/70A patent/GB1261322A/en not_active Expired
- 1970-03-06 CA CA076736A patent/CA927840A/en not_active Expired
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046717A (en) * | 1972-01-28 | 1977-09-06 | Lever Brothers Company | Detergent bars |
| JPS5046745A (enrdf_load_stackoverflow) * | 1973-08-08 | 1975-04-25 | ||
| US3975313A (en) * | 1974-06-19 | 1976-08-17 | Shelmire Jr Jesse Bedford | Solid amphoteric skin cleanser |
| US4073756A (en) * | 1976-04-26 | 1978-02-14 | Konishi Co., Ltd. | Solid adhesive compositions |
| US4075830A (en) * | 1976-04-26 | 1978-02-28 | Konishi Co., Ltd. | Solid adhesive compositions |
| US4303543A (en) * | 1979-02-27 | 1981-12-01 | The Procter & Gamble Company | Method for cleansing and conditioning the skin |
| US4273684A (en) * | 1979-05-03 | 1981-06-16 | Ajinomoto Co., Inc. | Transparent detergent bar |
| US4749515A (en) * | 1985-11-06 | 1988-06-07 | Lion Corporation | Liquid detergent composition |
| US5000877A (en) * | 1988-08-12 | 1991-03-19 | Mitsubishi Petrochemical Co., Ltd. | Aqueous liquid detergent containing an N-acylaspartate and a betaine or imidazoline surfactant |
| US5098608A (en) * | 1989-09-29 | 1992-03-24 | Shiseido Company Ltd. | Transparent solid detergent compositions containing n-acyl acidic amino acid salts |
| US5326493A (en) * | 1991-12-04 | 1994-07-05 | Kao Corporation | Solid detergent composition based on N-acyl sodium salt |
| US5518665A (en) * | 1993-01-11 | 1996-05-21 | Ajinomoto Co., Inc. | Transparent solid detergents |
| US6288023B1 (en) | 1995-07-12 | 2001-09-11 | Kyowa Hakko Kogyo, Co., Ltd. | Cleansing compositions comprising N-acylamino acids |
| US6350783B2 (en) | 1995-07-12 | 2002-02-26 | Kyowa Hakko Kogyo | Cleansing composition |
| US20090149370A1 (en) * | 2007-12-06 | 2009-06-11 | Conopco, Inc., D/B/A Unilever | Transparent Cleansing Bar |
| US7638471B2 (en) | 2007-12-06 | 2009-12-29 | Conopco, Inc., | Transparent cleansing bar comprising flipped N-acyl glutamate |
| JP2015221762A (ja) * | 2014-05-23 | 2015-12-10 | 川研ファインケミカル株式会社 | 毛髪も含めた全身用固形洗浄剤組成物 |
| WO2017075329A2 (en) | 2015-10-29 | 2017-05-04 | Dana-Farber Cancer Institute, Inc. | Methods for identification, assessment, prevention, and treatment of metabolic disorders using pm20d1 and n-lipidated amino acids |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2010303A1 (enrdf_load_stackoverflow) | 1970-09-24 |
| GB1261322A (en) | 1972-01-26 |
| CA927840A (en) | 1973-06-05 |
| DE2010303B2 (de) | 1977-01-13 |
| DE2010303C3 (de) | 1978-06-22 |
| ES377173A1 (es) | 1974-06-01 |
| JPS4811805B1 (enrdf_load_stackoverflow) | 1973-04-16 |
| FR2037778A5 (enrdf_load_stackoverflow) | 1970-12-31 |
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