US3888797A - Detergent composition - Google Patents

Detergent composition Download PDF

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US3888797A
US3888797A US357579A US35757973A US3888797A US 3888797 A US3888797 A US 3888797A US 357579 A US357579 A US 357579A US 35757973 A US35757973 A US 35757973A US 3888797 A US3888797 A US 3888797A
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good
detergent
salts
surface active
iood
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US357579A
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Hideo Marumo
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Carapus Co Ltd
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Carapus Co Ltd
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Priority claimed from JP6814570A external-priority patent/JPS541723B1/ja
Priority claimed from JP3039071A external-priority patent/JPS5013805B1/ja
Priority claimed from JP3039171A external-priority patent/JPS5118961B1/ja
Priority claimed from JP901972A external-priority patent/JPS5418283B2/ja
Priority claimed from US00250653A external-priority patent/US3855156A/en
Application filed by Carapus Co Ltd filed Critical Carapus Co Ltd
Priority to US357579A priority Critical patent/US3888797A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations

Definitions

  • the present surface active agent can be used widely as a detergent either independently or together with any known detergent.
  • the composition exhibits an excellent detergency, bubble formability and bubble durability for laundry, when washed with this composition, and moreover, it can give the laundry an antistatic property, a resistivity to resoiling and a soil releasability of a prolonged duration.
  • This invention relates to a new detergent composition. and more particularly to a new detergent composition containing at least one of improved amphoteric surface active agenst represented by the general formula (l). or its organic amine salts. ammonium salts. alkali metal salts. non-alkali metal salts or their acid complex salts. and improved amphoteric surface active agents derived from a compound having the general formula (II) through treatment with an amphoterizing' agent such as monochloroacetic. B-chloropropionic. y-chlorobutyric and monochlorosuccinic acids, and their alkali-metal salts or esters. maleic anhydride. acrylic. or methacrylic acid ester.
  • improved amphoteric surface active agenst represented by the general formula (l). or its organic amine salts. ammonium salts. alkali metal salts. non-alkali metal salts or their acid complex salts. and improved amphoteric surface active agents derived from
  • amphoteric surface active agent or its organic amine salts. ammonium salts. alkali metal salts. non-alkali metal salts. or their acid complex salts. as an active component:
  • a and B represent hydrogen atoms or groups R-QI'I"'CH2" OiCH CHR'OI PH or -(CH CHR'()).,H.
  • R is a hydrocarbon group having 2 to 28 carbon atoms and R is a hydrogen atom or a group CH;;
  • X represents a hydrogen atom or a hydrocarbon group having 6 to 30 carbon atoms.
  • Y represents a hydrogen atom. or a group CH;,. -CH. CH(CH3)CH 4 CH2', -(cHz)nCOOH,
  • n is an integer from I to 5
  • p and q are integers from O to 50. and when X is a hydrogen atom. at least one of A, B, D and E is a group or when A. B and Y are all hydrogen atoms. X is the hydrocarbon group having 2 to 28 carbon atoms. or
  • an ionic surface active agents such as linear alkylbenzenesuIfonates. sodium salts of saturated linear alcohol sulfates or the like. and non-ionic surface active agents such as nonylphenol ethylene oxide adduct of the like. are used in washing of natural fibers and synthetic fibers.
  • non-ionic surface active agents such as nonylphenol ethylene oxide adduct of the like.
  • detergents prepared from petroleum or alcohol base used as a detergent for food ware or vegetable have an excellent detergency but have a property to damage skins.
  • the use of the synthetic detergents has recently become a great problem.
  • biodegradability of a surface active agent blended in the synthetic detergent for washing. and the pollution by condensed phosphates have been recently regarded as the public pollution problem.
  • the present invention has been accomplished to overcome these undesirable problems and provides a novel detergent composition having less skin irritativeness, and moreover a good biodegradability. and further the present detergent composition does not require so much builders such as condensed phosphates.
  • novel compounds of the present invention can Now, a process for producing a novel surface active be used lone as a g n r added to h kn n agent used in the present invention will be outlined. tergent as an additive to improv rg n y.
  • the compound as represented by the general formula formability and bubble durability and endow an antista- (I) is obtained by adding 1,2-epoxyalkane or a-olefin tic property, resistibility to resoiling and soil releasabilto a natural or synthetic a-amino acid, or further by reity t a material [0 be washed.
  • the present detergent acting ethylene oxide or propylene oxide with the recomposition can be regarded as a king of p ym r sulting product.
  • a product (A) obtained electrolytes or polymeric surface active agent.
  • the antistatic propc 1 0 2 i' f erty and soil releasability can be endowed thereby to l the materials to be washed for a considerably pro- 3s OH CHZCHZCOONa longed period of time. That is to say, the present detergent composition can be used along in the antistatic, anti-redeposition and soil release treatments.
  • the feature of the present deter- (CHZCHZO) gent composition can be obtained without any failure I even if it is added to the other conventional detergent composition, but particularly when the present compo- CHZCHZCOONa sition is added to the conventional carpet shampoo ()(CH CH O) H consisting mainly of sodium alkylsulfates ester, very 2 2 p stable bubbles can be obtained.
  • the car- 3) pet surface is not so much wetted as necessary, and the fouling components can be effectively absorbed onto the bubble interfaces, whereby an excellent carpet sur- F (CHZCHZO) face having a good antistatic property, good anti-soil property and a good soil releasability can be obtained.
  • the present amphoteric surface active agent has less skin irritativeness, but has an action to protect the skin. Therefore, it is useful as a detergent for food wares, vegetable or the like. Furthermore, the
  • amphoteric surface active agent has a germici- (p q 20) (D) dal action, an antibacterial action and a deodorizing action, and therefore can be used as a substrate for toilet When an amino acid, whose amino and carboxyl soap, medical soap or toilet cleanser, or as a blending groups are protected, for example, N-acetylalanine component for these compositions.
  • the present surface ethyl ester, and a-tetradecene are subjected to radical active agent is used together with the conventional addition reaction in the presence of a peroxide or household detergent, industrial detergent, hair shamunder irradiation of ultraviolet rays.
  • a peroxide or household detergent, industrial detergent, hair shamunder irradiation of ultraviolet rays The protected poo, carpet shampoo, syndet bar, soap, or the like.
  • Furamino group of the resulting product is released and thermore, the present surface active agent can be used further the product is saponified with sodium hydroxas an organic builder for detergents.
  • ide a sodium salt of a-tetradecene-alanine adduct can On the other hand, the present detergent composibe obtained.
  • the compound as represented by the general formula 1" OH (ll) can be obtained. for example. by reacting 1,2- t expoxyalkane with propylene diamine.
  • the present am- I 1 2 ICHCH 2 photeric surface active agent can be obtained by reacting an amphoterizing agent. for example, methyl acrym 2 ICHCHZ I late. with the resulting compound of the general for- CH3 mula (ll).
  • the resulting compound is further saponified with sodium hydroxide thereby to obtain a sodium salt of the amphoteric surface active agent. as shown below:
  • amphoteric surface active agents having the formula (I) include the following compounds:
  • Table 3 Table 4-Continued Static friction- Bubble Wetting of Compound No. a] coefficient Hand feel stablllty the carpet Antistatic effect Com- Soil right after I Half time of 12 0202 Soft Good 5 pound 13 0195 Soft Good No. releasability washing leakage (sec.)] l4 0.200 Soft Good 15 (1.193 Soft Good s s t 9 0.199 S ft (.1 t 7 l l 0310 88f can 33 Good faster dry- 1.8 23 0.190 Soft Good ")2 25 0.2] 1 Soft Good ll) Feeling of 26 0.210 Soft (iood dryness.
  • Glass cleaners having the following composition were prepared. and glass was washed with the thus prepared compositions.
  • the present surfactants l4, l6, l8. 19. 21-.- 22, 23. 27. 30. 32 and 33 were used. It was found that the compositions had a good detergency. and a lustrous glass surface was obtained after the washing.
  • compositions had a good detergency and endow a good hand feel and antistatic effect.
  • a detergent composition consisting essentially of at least one surface active agent as the active component of the formula:
  • N c cooa wherein either A or B is hydrogen and A and B are independently RcH-cH l O(CH CHRO) H (CH CHR'O) l-l or COCH;, I v
  • R is an alkyl radical off) to 28 carbon atoms.
  • R is hydrogen or methyl. and p and q are independently integers from O to 50: X is hydrogen or an alkyl radical of 6 to 28 carbon atoms; Y is hydrogen, methyl, CH CH(CH )CH where n is an integer from l to 5, and
  • D and E are independently A and B; provided that when X is hydrogen. at least one of A, B, D and E is and salts thereof.
  • a detergent composition comprising the detergent of claim 1 blended with at least one detergent builder.
  • a detergent composition consisting essentially of at least one surface active agent as the active component of the formula:
  • X is hydrogen or an alkyl radical of 6 to 28 carbon atoms: Y is -(CH ),,COOH or D -(CH N 2 3 24 where n is an integer from 1 to 5, and R CH CH2" D and E are independently A and B; provided that when X is hydrogen at least one of D O or E is Q and the salts thereof.

Abstract

A new detergent composition at least one of surface active agents represented by the general formula (I), its organic amine salts, ammonium salts, alkali metal salts and nonalkali metal salts, or their acid complex salts, and/or an amphoteric surfactant derived from a compound of the general formula (II) by treatment with an amphoterizing agent, its organic amine salts, ammonium salts, alkali metal salts, non-alkali metal salts or their acid complex salts, as an active component:

WHERE A, B, X, Y, R, Z, W, m, n are as defined in the specification. The present surface active agent can be used widely as a detergent either independently or together with any known detergent. The composition exhibits an excellent detergency, bubble formability and bubble durability for laundry, when washed with this composition, and moreover, it can give the laundry an antistatic property, a resistivity to resoiling and a soil releasability of a prolonged duration.

Description

United States Patent [191 Marumo June 10, 1975 DETERGENT COMPOSITION [75] Inventor: Hideo Marumo, Tokyo, Japan [73] Assignee: Carapus Company, Limited, Tokyo,
Japan 22 Filed: May 7,1973
21 Appl. No.: 357,579
Related U.S. Application Data [62] Division of Ser. No. 250,653, May 5, 1972.
[30] Foreign Application Priority Data May 10, 1971 Japan 46-30391 Jan. 26, 1972 Japan 47-9019 [52] U.S. Cl. 252/527; 260/534 R; 260/534 E; 260/534 M; 252/DIG. l0; 252/DIG. 13;
[51] Int. Cl Clld 3/066; C07c 101/04;
C07c 101/24 [58] Field of Search 260/534 R, 534 E, 534 M;
[56] References Cited UNITED STATES PATENTS 2,446,478 8/1948 Kremers 260/534 M X 3,539,572 11/1970 Schroder et a1 260/534 R X 3,726,797 4/1973 Sundby 252/527 X FOREIGN PATENTS OR APPLICATIONS 1,167,192 10/1969 United Kingdom 1,216,731 12/1970 United Kingdom 1,218,251 l/l97l United Kingdom Primary Examiner-Leland A. Sebastian Attorney, Agent, or FirmCushman, Darby & Cushman [5 7 ABSTRACT \N c cooa (I) R/ 1 y R Icii CH2 NX(CHz) N w (II) where A, B, X, Y, R, Z, W, m, n are as defined in the specification. The present surface active agent can be used widely as a detergent either independently or together with any known detergent. The composition exhibits an excellent detergency, bubble formability and bubble durability for laundry, when washed with this composition, and moreover, it can give the laundry an antistatic property, a resistivity to resoiling and a soil releasability of a prolonged duration.
4 Claims, No Drawings DETERGENT COMPOSITION CROSS REFERENCE TO RELATED APPLICATIONS This is a division of my application Ser. No. 250.653. filed May 5. I972.
BACKGROUND OF THE INVENTION 1. Field of the Invention:
This invention relates to a new detergent composition. and more particularly to a new detergent composition containing at least one of improved amphoteric surface active agenst represented by the general formula (l). or its organic amine salts. ammonium salts. alkali metal salts. non-alkali metal salts or their acid complex salts. and improved amphoteric surface active agents derived from a compound having the general formula (II) through treatment with an amphoterizing' agent such as monochloroacetic. B-chloropropionic. y-chlorobutyric and monochlorosuccinic acids, and their alkali-metal salts or esters. maleic anhydride. acrylic. or methacrylic acid ester. acrylonitrilc or the like, thereby to form an amphoteric surface active agent. or its organic amine salts. ammonium salts. alkali metal salts. non-alkali metal salts. or their acid complex salts. as an active component:
t\ C COOH I'll wherein A and B represent hydrogen atoms or groups R-QI'I"'CH2" OiCH CHR'OI PH or -(CH CHR'()).,H. (wherein R is a hydrocarbon group having 2 to 28 carbon atoms and R is a hydrogen atom or a group CH;;). X represents a hydrogen atom or a hydrocarbon group having 6 to 30 carbon atoms. Y represents a hydrogen atom. or a group CH;,. -CH. CH(CH3)CH 4 CH2', -(cHz)nCOOH,
(wherein n is an integer from I to 5).
(wherein D and E are hydrogen atoms or groups R-CH-CH;
l O (CH CHR'O) PH or (CH CHR'O),,H). p and q are integers from O to 50. and when X is a hydrogen atom. at least one of A, B, D and E is a group or when A. B and Y are all hydrogen atoms. X is the hydrocarbon group having 2 to 28 carbon atoms. or
/Y R ca-ca {Nx(ca N or (CH CHR'O),,H), m is an integer from Z to It). a is an integer from O to 5. and X. Y. Z and W can take groups different from one another at the same time.
2. Description of the Prior Art Generally, an ionic surface active agents such as linear alkylbenzenesuIfonates. sodium salts of saturated linear alcohol sulfates or the like. and non-ionic surface active agents such as nonylphenol ethylene oxide adduct of the like. are used in washing of natural fibers and synthetic fibers. However, when such detergents are used, the fibers cleansed with such detergents have a deteriorated hand feel and the antistatic property of the fibers is lost. Therefore. it has been the usual practice to give the washed fibers an additional treatment with a soft-finishing agent or an antistatic agent. However. these properties which are thus added to the fibers disappear when the fibers are washed again. On the other hand. when the fibers are washed with a known detergent mixed with a soft-finishing agent and an antistatic agent. the individual effects of these mixed agents are not exhibited clearly. but rather they serve. in many cases. only to lower the activity of the detergent per se. Therefore, when the soft-finishing agent. antistatic agent or the like. are used. it is necessary to add these agents into a rinsing solution after cleansing or to subject the washed fibers to a separate treatment with these agents. and thus a great inconvenience is ex perienced.
Further. detergents prepared from petroleum or alcohol base used as a detergent for food ware or vegetable have an excellent detergency but have a property to damage skins. Thus. the use of the synthetic detergents has recently become a great problem. Furthermore. the biodegradability of a surface active agent blended in the synthetic detergent for washing. and the pollution by condensed phosphates have been recently regarded as the public pollution problem.
SUMMARY OF THE INVENTION The present invention has been accomplished to overcome these undesirable problems and provides a novel detergent composition having less skin irritativeness, and moreover a good biodegradability. and further the present detergent composition does not require so much builders such as condensed phosphates.
In the prior patent application of the present inventor for a detergent composition U.S. Ser. No. 168,413, it was disclosed that a water-insoluble metal salt of the amphoteric surface active agent ofa long-chain imidaz- 3 4 oline type was dispersed and solubiliz d in a Water Y bile, ship or vehicle cleaner, or as a cleaner for plant or" tem Wlth effflctlve dlspersalltx and h resultm' equipments in the food industry, or cleaner for food ittransparent solution was externally deposited and abe|f or as a l i agent d i id f f d sorbed on the surfaces of the fibers. As a result of furmi or h li ther studies, the present inventors have found that the 5 similar effect can be attained by the present novel com- DETAILED DESCRIPTION OF THE PREFERRED pounds EMBODIMENTS The novel compounds of the present invention can Now, a process for producing a novel surface active be used lone as a g n r added to h kn n agent used in the present invention will be outlined. tergent as an additive to improv rg n y. bubble 10 The compound as represented by the general formula formability and bubble durability and endow an antista- (I) is obtained by adding 1,2-epoxyalkane or a-olefin tic property, resistibility to resoiling and soil releasabilto a natural or synthetic a-amino acid, or further by reity t a material [0 be washed. The present detergent acting ethylene oxide or propylene oxide with the recomposition can be regarded as a king of p ym r sulting product. For example, a product (A) obtained electrolytes or polymeric surface active agent. Therel b reacting di di glutamate i h 1 2- fore, its critical micelle formation concentration is very epoxydodecane in a solvent mixture of alcohol-water is low, for example, about 1/100 to 1/1000 of that of double-decomposed with calcium chloride toa comalkylbenzcnesulfonates. That is, the present detergent pound (B):
C H CH--CH NH CH-COONa C H -CH-CH NH-CHCOONa l a (A) O CH CH COONa OH CH CH COONa CH21-CHCH2NHCHCOO (A) CaCIL Ca (B) OH CHZCHZCOO composition can exhibit a good surface activity at a When moles of ethylene oxide are added to one very low concentration and shows a good detergency. mole of the product (A), a compound (C) is obtained. Furthermore. a strong monolayer is formed on the suren t mp iS l compos With faces of material to be washed through absorption, and can be stably retained on the surface even in the cleanszinc chloride, 21 compound (D) is obtained:
ing step or even after drying. Thus, the antistatic propc 1 0 2 i' f erty and soil releasability can be endowed thereby to l the materials to be washed for a considerably pro- 3s OH CHZCHZCOONa longed period of time. That is to say, the present detergent composition can be used along in the antistatic, anti-redeposition and soil release treatments.
As described above, the feature of the present deter- (CHZCHZO) gent composition can be obtained without any failure I even if it is added to the other conventional detergent composition, but particularly when the present compo- CHZCHZCOONa sition is added to the conventional carpet shampoo ()(CH CH O) H consisting mainly of sodium alkylsulfates ester, very 2 2 p stable bubbles can be obtained. Furthermore, the car- 3) pet surface is not so much wetted as necessary, and the fouling components can be effectively absorbed onto the bubble interfaces, whereby an excellent carpet sur- F (CHZCHZO) face having a good antistatic property, good anti-soil property and a good soil releasability can be obtained. Znch Moreover, the present amphoteric surface active agent has less skin irritativeness, but has an action to protect the skin. Therefore, it is useful as a detergent for food wares, vegetable or the like. Furthermore, the
l C 0 H21-cH-CH1 "NCH COO I l CHQCHZCOO O(CH2CH2O) H present amphoteric surface active agent has a germici- (p q 20) (D) dal action, an antibacterial action and a deodorizing action, and therefore can be used as a substrate for toilet When an amino acid, whose amino and carboxyl soap, medical soap or toilet cleanser, or as a blending groups are protected, for example, N-acetylalanine component for these compositions. The present surface ethyl ester, and a-tetradecene are subjected to radical active agent is used together with the conventional addition reaction in the presence of a peroxide or household detergent, industrial detergent, hair shamunder irradiation of ultraviolet rays. The protected poo, carpet shampoo, syndet bar, soap, or the like. Furamino group of the resulting product is released and thermore, the present surface active agent can be used further the product is saponified with sodium hydroxas an organic builder for detergents. ide, a sodium salt of a-tetradecene-alanine adduct can On the other hand, the present detergent composibe obtained. When the resulting sodium salt is doubletion has a wide use as an industrial detergent, for examdecomposed with the corresponding inorganic metal ple, various detergents in the fiber industry, adetergent salt, for example, magnesium chloride, a compound in the cleaning industry, a metal detergent, an automo- (E) is obtained.
peroxide ultraviolet irradiation Nit i. c n -c-cooNa (E) NaOH 1 MgCit; l
The compound as represented by the general formula 1" OH (ll) can be obtained. for example. by reacting 1,2- t expoxyalkane with propylene diamine. The present am- I 1 2 ICHCH 2 photeric surface active agent can be obtained by reacting an amphoterizing agent. for example, methyl acrym 2 ICHCHZ I late. with the resulting compound of the general for- CH3 mula (ll). The resulting compound is further saponified with sodium hydroxide thereby to obtain a sodium salt of the amphoteric surface active agent. as shown below:
R ca cn NH2(CH2) na RCHCHZNIHCHZ) NH l /N-CHCOO Mg R cucu umcn hnu CH2 cncoocn I on RCHCHZNIHCHZ) rmca cn coocn R'CHCH2NH(CH2) gNHCHgCHgCOOCHg NaOH RCHCH NH(CH NHCH CH COONEi CH OH I OH When ethylene oxide or propylene oxide is added to l'c 0H2 CHCH NHCHCOO the resulting sodium salt, adducts containing various l l J 2L1 moles of ethylene oxide or propylene oxide can be ob- L OH CHZCHZCOO tained. (5)
Examples of the amphoteric surface active agents having the formula (I) include the following compounds:
i'c a ca-ca n-cncoo 1 pc n cacn naca coo l I Ca 1 Ca 5 on ca ca coo L 01-1 2 (1) L COCHa J (6) C1QHZQCHCHZNHCHZCOO] l Na c a cncn NHCHCOO 0a (2 2 I OH NHCH CI-IC 2H2 5 Ba L l Tc 2 an 5 cncn micucool on 2 I. 'lCa L OH CH3 2 (3) (7) ca cool ICIQHZICH'CHZN\ K2 L I cn coo J F OH 1 cn coo c 0H2 cncn -N cn coo I Na (49) I I L OH CH COO on 1 I cn coo I 0 OH: ,cncri u (cn cn o H Li (50) cn ca m a i in O(CH2CH2O) pH (p+q+r=9) fc ii CHCH NHCH CH CH NHCH CH COO I Na l OH 1 OH ca ca coo I OH Na (52) L crr ca coo C 61-13 3CHCH2NHCH2CH2COO L I JNE (53) 1' /CH2CH2COO [c 11 3CHCH2N\ [NH (CHZCHZOH) 1 (54) L l ca ca coo fc a caca macn cn ma cacoo (NHu)2 (55) I I L on ca coo.
OH OH 5 l (CHZCHZO) a ;c 6H5 3CH-CH2 'N -ca CH2 -ca 'N/ r Z Z H I (CH2CH20)sH K (56) t CHZCOO CH COO L C(CHzCHZO) pH (p+q+r+s=40) Now, the present invention will be explained in departs of the present amphoteric surface active agent, 5 tail. referring to Examples. In the Examples part" is parts oflsodiummetasilicate, 8 parts of soda ash and 77 by weight. parts of Glaubers salt. These detergent compositions were charged each in a standard amount as the heavy EXAMPLE I duty detergent (0.165% by weight) into an electric Detergent COmPO t C p pa e each m 10 a washing machine filled with acrylic fibers (Vonnel, a
trademark of acrylic fibers made by Mitsubishi Rayon Co.. Ltd.. Japan) fouled by wearing. and subjected to washing according to the standard washing procedure. On the other hand. the acrylic fibers were Washed likewise with a commercially available synthetic detergent and a commercially available soft-finishing agent. Detergency and hand feel of the washed fibers were determined visually or by touch. The results are shown in Table 1. It is evident from Table 1 that the present detergent compositions have an excellent dctergency. even though the present detergent compositions contain less active components than those of the commercially available detergent. and contain no builder such as sodium tripolyphosphate. etc.
Table l Antistatic effect Half time of Compound No. Detergency Hand feel leakage (sec. )1
2 Very good (iood 2.] 5 cry good (iood 5.] 8 Very good (iood 3.6 Very Good 3.7 12 Very (iood 2.8 13 (iood 3.0 14 (iood 2.8 15 Good 3.5 l h (iood 3 7 l7 Good 5.2 l8 Good 3.5 l9 (iood 4.7 20 Good 4.0 21 (Rood 2.8 22 (iood 2.5 23 (iood 3.0 24 (lood 3.5 25 (iood 3.7 26 Good 4.0 7 Good 4.2 28 Good 4.0 29 Good 4.2 30 Good 2.8 36 (iood 3.2 37 Good 4.] 38 Good 3.7 40 good Good 4.4 44 good Good 7.6 46 good Good 4.8 47 good Good 4.2 48 good Good 5.0 49 good Good 3.5 50 good Good 3.7 Very good (iood 4.0 2 Very good Good 2.8 53 Very good Good 3.6 54 Very good Good 2.9 55 Very good Good 3.5 56 Very good Good 37 Commercial heavy duty detergent Very good Poor EXAMPLE 2 Five parts of the present surfactant was added to a commercial heavy duty detergent composition consisting, for example. of 25 parts of sodium linear alkylbenzenesulfonate (LAS). 25 parts of sodium tripolyphosphate, 5 parts of sodium metasilicate. 5 parts of soda ash and 40 parts of Glaubers salt. while the amount of LAS was reduced to 20 parts. whereby detergent compositions were prepared. Fouled polyester sheets were washed according to the standard washing procedure. using the respective detergent composition in a standard amount as the heavy duty detergent (0.165% by weight). The results are shown in Table 2. As shown in Table 2. the washed shirts had a good hand feel with an excellent dctergency in the case of the present detergent compositions. Further. cleansing could be carried out more easily by blending the present surfactant in the detergent composition.
Table 2 Antislatic effect [Half time of Compound No. Detergency Hand feel leakage tsec.l]
1 Very good (iood 2.5 2 Very good (iood 2.5 3 Very good (iood 3.0 4 Very good (iood 3.5 5 Very good Good in 6 Very good Good 2.0 7 Very good (iood 3.8 8 Very good (iood 4.0 9 Very good (lood 4.0 l0 Very good (iood 4.] l 1 Very good Good 3.5 12 Very good Good 1.8 13 Very good Good 2.7 14 Very good Good 5.0 15 Very good Good 4.5 16 Very good Good 4.0 17 Very good Good 3.7 18 Very good Good 3.0 l9 Very good Good 4.2 20 Very good Good 4.0 21 Very good Good 4.7 22 Very good Good 3.5 23 Very good Good 4.2 24 Very good Good 2.8 25 Very good Good 5.6: 26 Very good (iood 4.5 27 Very good (iood 4.5 28 Very good (Food 5.0 29 Very good Good 3.7 30 Very good (iood 3.5 3l Very good Good 4.2 32 Very good Good 4.5 33 Very good Good 5.0 34 Very good Good 3.7 35 Very good Good 3.0 36 Very good (iood 3.6 37 Very good Good 4.2 38 Very good Good 4.3 39 Very good Good 2.8 40 Very good (iood 4.4 41 Very good Good 5.0 42 Very good Good 3.7 43 Very good Good 5.0 44 Very good Good 7.8 45 Very good Good 5.4 46 Very good Good 3.5 47 Very good Good 3.0 48 Very good Good 3.8 49 Very good Good 2.8 50 Very good Good 3.0 51 Very good Good 4.2 52 Very good Good 3.5 53 Very good Good 3.0 54 Very good (jood 4.2 55 Very good Good 3.7 56 Very good Good 3.0 Commercial heavy duty detergent Very good Poor (control) EXAMPLE 3 Two "/1 by weight of the present surfactant was added to a hair shampoo composition consisting. for example. of 10 parts of lauryl sulfate triethanolamine. 2 parts of lauroyldiethanolamide. 8 parts of urea, 3 parts of sodium salt of lauryl alcohol ether sulfate (3 moles) and 76 parts of water to prepare hair shampoo. Womens hair was washed with the thus prepared hair shampoo according to the conventional procedure. The results are shown in Table 3. It is seen that the detergency and bubble stability are improved by blending the present surfactant to the conventional shampoo composition, and the good hand feel can be endowed to the hair after washing and drying.
Table 3 Table 4-Continued Static friction- Bubble Wetting of Compound No. a] coefficient Hand feel stablllty the carpet Antistatic effect Com- Soil right after I Half time of 12 0202 Soft Good 5 pound 13 0195 Soft Good No. releasability washing leakage (sec.)] l4 0.200 Soft Good 15 (1.193 Soft Good s s t 9 0.199 S ft (.1 t 7 l l 0310 88f can 33 Good faster dry- 1.8 23 0.190 Soft Good ")2 25 0.2] 1 Soft Good ll) Feeling of 26 0.210 Soft (iood dryness. 3s 0194 Soft Good 26 00nd fa 40 0.204 Soft Good ing 47 0.2 l0 Soft Good l-eelmg of 4S 0. l 95 Soft Good dryness, 49 0.206 Soft Good 27 od taster dry- 0.1 50 0. 202 Soft Good i 5] 0.200 Soft Good Feeling of 52 0. I 98 Soft Good dryness. 53 0.208 Soft Good 28 Good faster dry- ().l 54 0202 Soft Good ing 55 0.200 Soft Good Feeling of 56 0.198 SOfI 600d dryne5 Commercial h 29 Good faster dryl.4
shampoo 0.230 Rlgld Fulr i (control) Feeling of dryness. 38 Good faster dry- 0.1 EXAMPLE 4 mg 75 Feeling of dryness, 0.2 parts of the present surfactant was added to a car 46 Good faster dry 08 pet detergent consisting of 0.5 parts of sodium salt of ing lauryl sulfate, 0.15 parts of lauroyldiethanolamide and Ffielmg of 99 35 f h'l d h f h parts 0 water, w 1 e re ucing t e amount 0 t e 47 Good faster 03 sodium salt of lauryl sulfate to 0.3 parts thereby to preing pare carpet detergent compositions. Fouled beige nylon carpets were washed with the thus prepared de- 48 Good faster dr 0.7 tergent compositions according to the conventional Fi of carpet washing procedure comprising bubbling, brushdrynesi ing, leaving at a standstill and suction under vacuum. 49 Good faster y- L0 The results are shown in Table 4. It is obvious that the g' of carpet detergent composition has an improved deterdryness. gency and bubble stability and faster drying by blend- 000d gg ing the present surfactant into the conventional deter- Feeling f gent composition, and an antistatic property can be en- 51 G d g r dowed to the carpets after washing. g
Feeling of Table 4 dryness,
52 Good faster dry- 1.2 ing Wetting of Feeling of the carpet Antistatic effect drynessv Com- Soil right after [Half time of 53 Good faster L0 pound ing No. releasability washing leakage (sec.)] Feeling of dryness. Feeling of 54 Good faster dry- 08 dryness. ing 12 Good faster dry- 0.5 Feeling of mg dryness, Feeling of 55 Good faster dryas dryness, i 14 Good faster dry- 0.6 Feeling f mg I dryness, Feelmg of 56 Good faster dry 1.0 dryness, 55 ing 15 Good faster dry l.0 C
mg mercial S of carpet Foulings re- Wettish w ryn s5. 17 Good faster dry- 1.6 mam feelmg mg Feeling of 60 dryness. l8 Good faster dry- 1.5 EXAMPLE 5 111g Feeling of Ten parts of the present surfactants l2, l8 and 2l dryness. were added each to the detergent for food wares and 20 (mod faster Lll'V- l.4
ing 6s vegetable having the following compositlon, while reg Of ducing the amount of LAS to 10 parts. thereby to pre- 22 Good gg 'f s (U pare detergentcompositions for food wares and vegetaing ble. The thus prepared detergent compositions were tested by 10 household wives for 1 month in the winter season (February and it was found that the detergent compositions had a very good detergency and gave no irritation to hands, as compared with the controls.
Glass cleaners having the following composition were prepared. and glass was washed with the thus prepared compositions. In that case. the present surfactants l4, l6, l8. 19. 21-.- 22, 23. 27. 30. 32 and 33 were used. It was found that the compositions had a good detergency. and a lustrous glass surface was obtained after the washing.
Present surfactant Higher alcohol-ethylene oxide (9 moles) adduct Amisol CD (a product of Kawakami Fine Chemicals. Co.. Japan) lsopropyl alcohol Water 0.025% by weight 0.25 71 by weight 0.50 "/2 by weight 5.0 I? by weight 94.22571 by weight Refrigerators and food ware shelves were washed with the said detergent compositions, and it was found that the present detergent compositions had a strong detergency without damaging the plastic surface and painted surface, and a lustrous clean surface was obtained.
EXAMPLE 7 Ten parts of the present surfactant having the general formula I and 3 parts of the present surfactant derived from the compounds having the general formula II were melted. and 87 parts of hot water was added little by little with stirring thereto to dilute the surfactants. The resulting solution was passed through a homogenizer at 80C, and then to the normal temperature, whereby the detergent composition were obtained. The thus obtained detergent compositions were subjected to detergency tests in the same method as described in Example 1. The results are shown in Table 5.
The present compositions had a good detergency and endow a good hand feel and antistatic effect.
LII
I claim:
1. A detergent composition consisting essentially of at least one surface active agent as the active component of the formula:
N c cooa wherein either A or B is hydrogen and A and B are independently RcH-cH l O(CH CHRO) H (CH CHR'O) l-l or COCH;, I v
wherein R is an alkyl radical off) to 28 carbon atoms.
R is hydrogen or methyl. and p and q are independently integers from O to 50: X is hydrogen or an alkyl radical of 6 to 28 carbon atoms; Y is hydrogen, methyl, CH CH(CH )CH where n is an integer from l to 5, and
D and E are independently A and B; provided that when X is hydrogen. at least one of A, B, D and E is and salts thereof.
2. A detergent composition comprising the detergent of claim 1 blended with at least one detergent builder.
3. The detergent composition according to claim 1 wherein the surface active agent has the formula:
C EI CH'CH N-iJHCOOH l CH CH COOH OH coca 4. A detergent composition consisting essentially of at least one surface active agent as the active component of the formula:
X A l \N c cooH B y wherein A and B are both hydrogen,
X is hydrogen or an alkyl radical of 6 to 28 carbon atoms: Y is -(CH ),,COOH or D -(CH N 2 3 24 where n is an integer from 1 to 5, and R CH CH2" D and E are independently A and B; provided that when X is hydrogen at least one of D O or E is Q and the salts thereof.

Claims (4)

1. A DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF AT LEAST ONE SURFACE ACTIVE AGENT AS THE ACTIVE COMPONENT OF THE FORMULA:
2. A detergent composition comprising the detergent of claim 1 blended with at least one detergent builder.
3. The detergent composition according to claim 1 wherein the surface active agent has the formula:
4. A detergent composition consisting essentially of at least one surface active agent as the active component of the formula:
US357579A 1970-08-04 1973-05-07 Detergent composition Expired - Lifetime US3888797A (en)

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JP6814570A JPS541723B1 (en) 1970-08-04 1970-08-04
JP3039071A JPS5013805B1 (en) 1971-05-10 1971-05-10
JP3039171A JPS5118961B1 (en) 1971-05-10 1971-05-10
US16841371A 1971-08-02 1971-08-02
JP901972A JPS5418283B2 (en) 1972-01-26 1972-01-26
US00250653A US3855156A (en) 1970-08-04 1972-05-05 New detergent composition
US00283039A US3850853A (en) 1970-08-04 1972-08-23 Detergent composition
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DE2600778A1 (en) * 1976-01-10 1977-07-21 Henkel & Cie Gmbh USE OF BETAINES IN OIL EXTRACTION
US4076743A (en) * 1976-01-10 1978-02-28 Henkel Kgaa Novel betaines, processes for the preparation thereof and recovery of underground petroleum therewith
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
EP0005446A1 (en) * 1978-04-14 1979-11-28 Henkel Kommanditgesellschaft auf Aktien Amino-ether amphoteric surface-active compounds and process for their preparation
US4388077A (en) * 1981-08-07 1983-06-14 W. E. Greer Ltd. Composition for washing fabric
US5656586A (en) * 1994-08-19 1997-08-12 Rhone-Poulenc Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
US5789371A (en) * 1997-04-22 1998-08-04 Rhodia Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
US5846926A (en) * 1997-06-09 1998-12-08 Rhodia Inc. Nonionic gemini surfactants with three hydrophilic heads and two lipophilic tails
US6121222A (en) * 1996-12-27 2000-09-19 Rhodia Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
US20040037802A1 (en) * 2002-08-13 2004-02-26 Hong Zhao Releasable polymeric conjugates based on aliphatic biodegradable linkers
US20050197290A1 (en) * 2002-08-13 2005-09-08 Hong Zhao Releasable polymeric conjugates based on biodegradable linkers
WO2004108070A3 (en) * 2003-05-30 2005-11-03 Enzon Inc Releasable polymeric conjugates based on aliphatic biodegradable linkers
US20070021316A1 (en) * 2005-07-22 2007-01-25 Dilley Colin M Cleaner composition, article and method
CN114044818A (en) * 2021-12-09 2022-02-15 万华化学集团股份有限公司 Gelatin-based surfactant and preparation method and application thereof

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US2446478A (en) * 1944-10-06 1948-08-03 Gen Foods Corp Imitation maple flavor
US3539572A (en) * 1966-11-19 1970-11-10 Roehm & Haas Gmbh 2,5-diketo piperazines
US3726797A (en) * 1969-11-28 1973-04-10 Colgate Palmolive Co Detergent compositions and processes incorporating n-(2-hydroxy hydrocarbyl)iminodicarboxylates

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2600778A1 (en) * 1976-01-10 1977-07-21 Henkel & Cie Gmbh USE OF BETAINES IN OIL EXTRACTION
US4076743A (en) * 1976-01-10 1978-02-28 Henkel Kgaa Novel betaines, processes for the preparation thereof and recovery of underground petroleum therewith
US4090969A (en) * 1976-01-10 1978-05-23 Henkel Kommanditgesellschaft Auf Aktien Method of oil recovery by flooding employing betaine solutions
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
EP0005446A1 (en) * 1978-04-14 1979-11-28 Henkel Kommanditgesellschaft auf Aktien Amino-ether amphoteric surface-active compounds and process for their preparation
US4388077A (en) * 1981-08-07 1983-06-14 W. E. Greer Ltd. Composition for washing fabric
US5656586A (en) * 1994-08-19 1997-08-12 Rhone-Poulenc Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
US6121222A (en) * 1996-12-27 2000-09-19 Rhodia Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups
US5789371A (en) * 1997-04-22 1998-08-04 Rhodia Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
US5846926A (en) * 1997-06-09 1998-12-08 Rhodia Inc. Nonionic gemini surfactants with three hydrophilic heads and two lipophilic tails
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
US20080305070A1 (en) * 2002-08-13 2008-12-11 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
US7413738B2 (en) 2002-08-13 2008-08-19 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on biodegradable linkers
US8192743B2 (en) 2002-08-13 2012-06-05 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
AU2005316520B2 (en) * 2002-08-13 2011-09-29 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
US7122189B2 (en) * 2002-08-13 2006-10-17 Enzon, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
US20050197290A1 (en) * 2002-08-13 2005-09-08 Hong Zhao Releasable polymeric conjugates based on biodegradable linkers
US20060286065A1 (en) * 2002-08-13 2006-12-21 Hong Zhao Releasable polymeric conjugates based on aliphatic biodegradable linkers
US7897647B2 (en) 2002-08-13 2011-03-01 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
US20040037802A1 (en) * 2002-08-13 2004-02-26 Hong Zhao Releasable polymeric conjugates based on aliphatic biodegradable linkers
JP2006526569A (en) * 2003-05-30 2006-11-24 エンゾン インコーポレイテッド Releasable polymer conjugates based on aliphatic biodegradable linkers
US20070166276A1 (en) * 2003-05-30 2007-07-19 Hong Zhao Releasable polymeric conjugates based on aliphatic biodegradable linkers
JP2011174077A (en) * 2003-05-30 2011-09-08 Enzon Inc Releasable polymeric conjugate based on aliphatic biodegradable linker
US7087229B2 (en) 2003-05-30 2006-08-08 Enzon Pharmaceuticals, Inc. Releasable polymeric conjugates based on aliphatic biodegradable linkers
JP4824404B2 (en) * 2003-05-30 2011-11-30 エンゾン インコーポレイテッド Releasable polymer conjugates based on aliphatic biodegradable linkers
WO2004108070A3 (en) * 2003-05-30 2005-11-03 Enzon Inc Releasable polymeric conjugates based on aliphatic biodegradable linkers
US7776811B2 (en) * 2005-07-22 2010-08-17 Honeywell International Inc. Cleaner composition, article and method
US20070021316A1 (en) * 2005-07-22 2007-01-25 Dilley Colin M Cleaner composition, article and method
CN114044818A (en) * 2021-12-09 2022-02-15 万华化学集团股份有限公司 Gelatin-based surfactant and preparation method and application thereof
CN114044818B (en) * 2021-12-09 2023-05-26 万华化学集团股份有限公司 Gelatin-based surfactant and preparation method and application thereof

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