CN87107303A - The softening detergent compositions that contains specific poly-amide softening agent - Google Patents

The softening detergent compositions that contains specific poly-amide softening agent Download PDF

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Publication number
CN87107303A
CN87107303A CN198787107303A CN87107303A CN87107303A CN 87107303 A CN87107303 A CN 87107303A CN 198787107303 A CN198787107303 A CN 198787107303A CN 87107303 A CN87107303 A CN 87107303A CN 87107303 A CN87107303 A CN 87107303A
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Prior art keywords
composition
acid
tenderizer
group
nitrogenous
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CN198787107303A
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Chinese (zh)
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汉斯·雷蒙克
艾尔弗雷德·布什
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Procter and Gamble Co
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Procter and Gamble Co
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Publication of CN87107303A publication Critical patent/CN87107303A/en
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    • 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
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/32Amides; Substituted amides
    • 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
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group

Abstract

The present invention discloses the detergent composition that contains specific poly-amide softening agent, and this composition can provide bating effect and other fabric nursing benefit at whole washing process.

Description

The present invention relates to contain the soft washing agent composition of the poly-amide softening agent of strict difinition.
This composition is except providing good purifying property, during washing, from first to last also shown its softening performance, the benefit of extra fabric nursing also is provided simultaneously, for example, can make the torr fabric produce static resistance, wrinkle resistance, easily scald property, color fidelity and prevent the effect of woolen bonding and so on.
For a long time, people are inquiring into the prescription of fabric treatment composition, and hope can be found the method that can make fabric-softening in laundering of textile fabrics.The method of using dirt tenderizer or amine substance is arranged among the many methods that proposed, or use the method for two component mixtures, for example, at German Patent 29.64.114,28.57.16,24.39.541, described in 23.34.899 and European patent 0 026 528 and 0 028 432.
In soap (English Patent 1 514 276), lipid acid (disclosed E.P.A.0133804) or phosphoric acid ester (disclosed E.P.A 0 168 889), all once added the tenderizer of amine as whole washing process.
Yet, often because between some component (as, between peroxyacid bleach and the tenderizer) uncompatibility, make the problem of the handiness that the whole softening detergent compositions prescription of washing of present technique allocated.
Handle in the industry in weaving, people have used Carboxylamide as static inhibitor (German Patent 30 43 618), and make static inhibitor (French Patent 2,531,447) with N-alkyl Unimac 5680 acid amides in laundry operations.Disclosing among the Japanese Patent J5 8144-175-A to adopt cationic softening agent and ethoxylated fatty acid acid amides to carry out industrial fabric treating.
People are known, and the alkoxyl group fatty acid amide can be used as tensio-active agent (European patent 0 000 595) and viscosity modifier (European patent 0 112 719).
German patent application 19 59 007 discloses, and can use single ethanol amide as tenderizer.German patent application 33 10 417 discloses, and can use fatty diglycollic amide as static inhibitor/not yellowing agent.
Above-mentioned document, none is disclosed in and uses the specific acid amides of the present invention in the softening detergent compositions.
An object of the present invention is to provide possess good purification, the detergent composition of softening and fabric nursing performance.
Another object of the present invention provides softening detergent compositions, and this composition can higher flexibility be allocated, especially under the situation that the peroxy acid bleach compound exists.
In fact at present have been found that, when peroxyacid bleach rationally exists, if in detergent composition, use the acid amides of strict difinition to make tenderizer, then no matter to the purification of fabric and softening, still to other " fabric nursing " benefit, all can obtain good effect.
The present invention relates to during washing, the detergent composition of the fabric nursing benefit that comprises ramollescence from first to last can be provided, this composition contains detersive surfactant and nitrogenous fabric softener, also can contain detergent additive when needing, and it is characterized in that
Nitrogenous tenderizer is selected from the compound of following group:
1) the following diamide of chemical formula:
2) the following diamide of chemical formula:
Wherein, R 1, R 2, R 3, R 4All independently be selected from the C that may contain hydroxyl groups, ester group and/or ehter bond 12-22Alkane (alkene) base, aryl or alkaryl.
R 5Be selected from alkane (alkene) base that contains 1 to 10 carbon atom, aryl, substituted aryl, heteroaryl, substituted heteroaryl, polyaryl, and R 5May contain a plurality of hydroxyl groups, ester group and/or ehter bond.
4) with 1) to 3) sulphonamide that described acid amides is corresponding.
The used tenderizer of tenderizer-the present invention all is selected from Chemical formula 1 mentioned above) to 4) acid amides or sulphonamide.
Best, Chemical formula 1) to 4) in R 1, R 2, R 3And R 4, be selected from Tallow, beef and coconut alkyl entirely.
Preferred compound is R 5Be C 1-5Alkyl or alkenyl, or the formula 2 of phenyl or substituted phenyl) compound.
Work as R 5When being alkane (alkene) base, better with the compound that contains four-coconut and four-Tallow, beef diamide, and these diamide are from propanedioic acid, Succinic Acid, toxilic acid, pentanedioic acid and adipic acid deutero-.
In the above-mentioned compound preferably, particularly preferably be four coconut hexanediamides.
Work as R 5When being aryl, connect R 3And R 4The amide group of chain can be positioned at and R 1And R 2Ortho position, a position or the contraposition of the amide group that chain links to each other.
Work as R 5When being phenyl or substituted phenyl, compound is four-Tallow, beef terephthaloyl amine and four coconut terephthaloyl amine preferably.
For R 5, polyaryl is a phenylbenzene preferably.
By weight, the consumption of tenderizer is 0.1% to 15%, with 1% to 10% better, is preferably 3% to 6%.
In highly preferred embodiment, earlier with tenderizer and dispersant, the mixture with gained adds in all the other components of composition then.
Arbitrary dispersion agent commonly used all can be used as such use.The dispersion agent that is suitable for comprises that by primary aliphatic alcohols or secondary alcohol (for example animal lipidol, or alkylphenol) nonionogenic tenside with 5-12 ethylene oxide unit(s) condensation obtains reaches 85201127, No. 9 described phosphoric acid ester of european patent application.These phosphoric acid ester are sold with the trade name of " Servoxyl VPAZ ", and chemical formula is R '-O(CH 2-CH 2O) mPO(OH) 2, R ' in the formula=C 12-14, m=1-5.
In particularly preferred embodiment, be to use the dispersion agent of lipid acid as the acid amides tenderizer.Use the lipid acid (for example lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, oleic acid and composition thereof) that in alkyl chain, has 10 to 20 carbon atoms more favourable in the present invention.Particularly preferably be mixture with palmitinic acid and stearic acid.
Be that 1/1 to 10/1 deal is used the lipid acid dispersion agent preferably by the weight ratio of acid amides tenderizer and lipid acid.
Detersive surfactant-in order to obtain conventional purification benefit, composition of the present invention generally should contain organic tensio-active agent.
The detersive surfactant that this paper is suitable for comprises well-known synthetic anion surfactant, nonionogenic tenside, soda acid amphoterics and zwitterionics.Wherein, representative α-sulfonate for alkylbenzene sulfonate, alkyl-sulphate and sulfated alkyl ether, paraffin sulfonate, ethylenic sulfonate, the pure and mild alkylphenol of alkoxyl group (particularly oxyethyl group), amine oxide, lipid acid and the fatty acid ester known in the washing technology etc.In general, above-mentioned detersive surfactant contains C 9-C 18Alkyl in the scope; Anion surfactant can use with the form of its sodium salt, sylvite or tri ethanol ammonium salt; Nonionogenic tenside generally contains 5-17 the ethylene oxide group of having an appointment.Among the United States Patent (USP) 4.111.855 itemizing above-mentioned typical detersive surfactant.At composition of the present invention, preferably select C for use 11-C 16Alkylbenzene sulfonate, C 12-C 18Paraffin sulfonate and alkyl-sulphate and ethoxy alcohol and alkylphenol.
Water-soluble soap, the common coconut of for example knowing in the present technique or the soda soap and the potash soap of Tallow, beef can be used as the tensio-active agent of this paper equally.
In the composition of this paper, can contain the tensio-active agent component that is low to moderate 1% content, but preferably should contain 5% to 40%, it is good especially to contain 10% to 30% tensio-active agent person.The nonionogenic tenside of ethoxylation is the preferred surfactants component with mixture as the anion surfactant of alkylbenzene sulfonate, alkylsulfonate and paraffin sulfonate and so on, is used for removing general mud and mottling on the fabric in whole cleaning process.
Detergent additive-acid amides tenderizer is preferably with using with the compatible dirt tenderizer of washing composition, but this is not essential.Described dirt tenderizer is that some are known in the washing field, and is used widely in the washing industry of the Europe and the U.S..Above-mentioned dirt tenderizer comprises various heat treated kaolin and various multiwalled montmorillonite.The dirt tenderizer is the montmorillonite dirt tenderizer described in No. 1 400 898, No. 23 34 899, German patent application and the English Patent preferably; Can consult these patent applications about detailed description.In composition preferably, the content of dirt tenderizer is at least 1%, is generally 1-20%, preferably 2-10%.
The composition of this paper can contain other component that helps its purifying property.For example, to contain SYNTHETIC OPTICAL WHITNER, especially the composition of peroxyacid bleach is more favourable, and to the stability of composition and whole performance without any infringement.This is because the consistency of acid amides tenderizer of the present invention and peroxyacid bleach.Within the scope of the invention, the term peroxyacid bleach had both comprised that peroxy acid itself had also comprised the system that can produce peroxy acid at the scene.
The meaning of peroxy acid itself has comprised an alkali metal salt and the alkaline earth salt of peroxy acid.Usually all use peroxy acid and diperoxy acid, for example diperoxy 12 (alkane) acid (DPDA) or peroxide phthalic acid.
Can provide the system of peroxy acid to form at the scene by the promoting agent of peroxygen bleach and peroxygen bleach.
Peroxygen bleach is some compounds that can produce hydrogen peroxide in the aqueous solution; These compounds are known in the art, and comprise hydrogen peroxide, alkali metal peroxide, organo-peroxide SYNTHETIC OPTICAL WHITNER (as, urea peroxide), the inorganic persalt SYNTHETIC OPTICAL WHITNER (as, alkali-metal perborate, percarbonate, superphosphate and persilicate) etc.
Preferentially select Sodium peroxoborate (industrial form supply), hydration sodium carbonate peroxide, hydration pyrophosphate peroxide and hydration urea peroxide for use with water and four water sodium perborate.
Hydrogen peroxide that is produced and bleach-activating agent reaction generate peroxyacid bleach.The classification of bleach activator comprises ester class, acid imide, imidazoles, oximes, and carbonate.In these classifications, material comprises neighbour-ethoxy-benzoic acid methyl ester preferably; Right-the phenetole sodium sulfonate (4-acyloxy in ninth of the ten Heavenly Stems benzene sulfonic acid sodium salt (Sodium 4-nonanoxyloxybenzene sulfonate) for example, hot acyloxy benzene sulfonic acid sodium salt of 4-and 4-acyloxy in last of the ten Heavenly stems benzene sulfonic acid sodium salt); Biological phenol A diacetate esters; Tetra acetyl ethylene diamine; Tetra-acetylated hexamethylene-diamine; Tetra-acetylated methylene diamine.
Other disclosed extremely preferred peroxide bleaching promoting agent in United States Patent (USP) 4.483.778 number and 4.539.130 number is the alkyl or the alkenyl ester class of alpha-substitution, the hot acyloxy of 4-(2-chlorine for example) benzene sulfonic acid sodium salt, 4-(3,5,5-trimethyl acetyl oxygen base) benzene sulfonic acid sodium salt.Suitable peroxy acid also is the peroxide bleaching promoting agent, for example at disclosed european patent application the 0 166, general formula described in No. 571 is the compound of RXAOOH and RXAL, in the formula, R is hydroxyl carbyl (Hyd roxcarbyl group), and X is a heteroatoms, and A is a carbonyl bridged bond base, L is a leavings group, especially Oxybenzene sulfonate.
On the other hand, the composition of this paper can contain arbitrary other type, habitual SYNTHETIC OPTICAL WHITNER in detergent composition.Also advise very much simultaneously in the whole detergent composition of washing, including decontamination lotion promoter and/or metal ion sequestering agent.Classifiable compound and the compound of knowing in the art as decontamination lotion promoter comprise nitrilotriacetic acid ester, polycarboxylate, citrate, water-soluble phosphate (as, three-poly-phosphate and sodium orthophosphate and trisodium phosphate), silicate, and composition thereof.The metal ion sequestering agent comprises above-mentioned all compounds, also add the material of similar ethylenediamine tetraacetate and so on, amino poly phosphate (the polyfunctional organic acid and the salt of (aminopolyphosphonates) and phosphoramidate (DEQUEST) and other various wide range, item are too many, describe in detail in this inconvenience.Relevant above-mentioned substance is used for the exemplary of various detergent composition, sees also United States Patent (USP) 3.579.454.In general, the content of this washing assistant/sequestering agent is about 0.5% to 45% of composition.Zeolite (as, the zeolite A) washing assistant that is of a size of the 1-10 micron described in the German Patent 24 22 655 is particularly useful for the composition of low-phosphoric acid ester or non--phosphoric acid ester.
The laundry composition of this paper preferably also contains the enzyme such as amylase, proteinase, cellulase, so that strengthen its purifying property for various mud and mottling in washing process.Being applicable to the amylase and the proteinase of washing composition, is being known in the art, and these enzymes are at the commercial liquid state that can large quantities ofly buy and granulous washing composition.In this composition, the usage quantity of the detergency enzymes (the preferably mixture of amylase and proteinase) of industry is generally 0.001% to 2%, even higher.Other decontamination components that cater to the need very much in detergent composition of the present invention and be used are R 4R 5R 6R 7N +X -The quaternary ammonium compound of formula, in the formula, R 4Be that carbon atom is 10 to 20 alkyl, better to contain 12-18 carbon atom, and R 5, R 6And R 7Respectively be C 1To C 4Alkyl, preferably methyl; X -Be negatively charged ion, chlorion for example.The example of above-mentioned quaternary ammonium compound comprises C 12-C 14Alkyltrimethylammonium muriate and coconut palm alkyl trimethyl ammonium methyl sulfate.The usage quantity of quaternary ammonium compound is 0.5% to 5%, and is better with 1% to 3%.
In addition, except the component of having mentioned, this composition can also contain other various suitable components, generally provides benefit aesthetic or that increase product performance with these components in Industrial products.Typical component comprises pH regulator agent, spices, tinting material, fluorescent bleaches, outstanding dirty agent, hydrotropic agent and gelling conditioning agent, freeze-thaw stabilizer, sterilant, preservatives, foaming regulator and bleaching stibilizer.
During laundering of textile fabrics, in whole mode of washing, general working concentration is at least the composition of 500ppm, is preferably 0.10% to 1.5%, and pH value of aqueous solution is 7-11 in the rinse bath.This composition can wash to boiling spread at 5 ℃, and can obtain good effect.
The form of composition and preparation one detergent composition of the present invention can be arbitrary the proper physical state exist, that its form comprises is granular, liquid, pasty state and class sheet.By each component is mixed, with their altogether cohesions, littlely seal, be dispersed in the liquid vehicle, but and detachment absorption or with their coatings on a kind of on-granulated matrix, for example on the non-woven or the scraps of paper, can in all sorts of ways this composition is made suitable physical form.
Granulous composition preferably.
The method of the described granular composition of preferred preparation comprises the melt of preparation dispersion agent and acid amides, then this fused mixture is dispensed into remaining sum and is the decontamination component in the aqueous mixture that crutcher stirred, and press the standard method spraying drying.In another equal preferable methods, melt can be atomised on the detergent particles, also the composition of this paper can be sprayed onto on the particle of water or four water sodium perborate, sodium sulfate, yellow soda ash, water glass, sodium phosphate and so on or be sprayed onto on the clay of the above-mentioned type.
Following example is the preferred exemplary of the present invention of implementing, but the meaning of unrestricted standard of the present invention.
Example 1
With four coconut terephthaloyl amine (after the spraying, its total amount be whole prescription 5%) and till the mixture of lauric acid (whole prescription 1.5%) mixes, melts and is stirred to evenly.Stir the aqueous mixture that preparation comprises the standard of following component with crutcher.Listed percentage is meant the spraying drying per-cent of each component in whole prescription afterwards.
The component percentage
C 11-C 12Alkylbenzene sulfonate 6.2
Tallow, beef alcohol ethoxylate (EO11) 1.0
Tripoly phosphate sodium STPP 24.0
Sodium sulfate 15.0
Water glass 8.0
Montmorillonite carclazyte (Smectite clay) * 6.5
Carboxymethyl cellulose 0.4
Polyacrylic ester (outstanding dirty agent) 1.7
Enzyme 0.5
Fluorescent bleaches 0.23
Sulfonation phthalocyanine phthalocyanine zinc (Sulfonated Zinc Phthalocyanine) * * 25ppm
EDTA 0.2
Spices/mantoquita/minor additions 0.5
C 12-C 14Alkyltrimethylammonium muriate 1.9
Moisture content adds to 77%
Thereupon, the mixture in the crutcher is handled with standard method fully, carries out spraying drying simultaneously.After the drying, do mixed with particle Sodium peroxoborate (20%) and bleach activator (3% 3-5-5-tri-methyl hexanoic acid, sulfanilamide (SN) phenylester, sodium salt * * *) (3%).Then four coconut terephthaloyl amine/lauric acid melts are sprayed onto on the product of making.
* natural montmorillonite: ion-exchange capacity is
50 milligramequivalents/more than the 100 gram clays
* United States Patent (USP) 3.927.967.
* United States Patent (USP) 4.483.778 ﹠amp; 4.539.130
The composition of example 1 with identical but do not contain four coconut terephthaloyl amine/lauric material (object of reference) that is pre-mixed and compare, is measured their properties of softening to washing process.The scheme of test is the pliability of comparison fabric cloth sheet, method be with composition of the present invention and reference group compound distinguish laundering of textile fabrics once with 4 times.
Test conditions is as follows:
-full-automatic drum washing machine MIELE 423.
-be warming up to 90 ℃ from 15 ℃; Kept 50 minutes at 90 ℃
The concentration of-product in washing water is 1%
-18 grain/gallons (0.31 grams per liter) water hardness (the Ca/Mg ratio is 3: 1).
There are two exquisite identifiers that can work independently to judge comparison through washing and specialty (line) exsiccant print (swatches) with one, adopted 9-point grade (Scheffe scale) and utilized paired correlation technique.Its difference is recorded in the instrument of keeping the score (panel score nuites(PSU)) in, positive number is represented better performances, is minimum effective difference (LSD) of 95% but also can calculate confidence level.
Test-results is as follows:
Pliability (1 pair of object of reference of example)
1 time 4 times
The * of HEAVY FLANNELETTE fabric+1.30(0.49)+0.80(0.44)
(12)
Trevira+1.0(0.63)+1.00(0.00)
(12)
* the numerical value in the parantheses is LSD value (asking for an interview original text)
These results show during whole washing, and can obtain the benefit of significant flexibility from composition of the present invention.
Example 2
The prescription of low-phosphorous spray-dried detergent is as follows:
The component percentage
Zeolite A(1-10 micron) 26.0
Sodium nitrilo triacetate 5.0
Montmorillonite carclazyte (Smectite clay) * 3.0
Four coconut hexanediamide/lauric acid (weight ratio is 3: 1) * * 5.0
C 11-C 12Benzene sulfonamide acid esters 6.5
Tallow, beef ethoxylate (EO 9-11) 0.5
Sodium peroxoborate 4H 2O*** 20
Tetra acetyl ethylene diamine (TAED) * * * 3
Water glass 8
CMC 1
Sodium sulfate 18
Enzyme (amylase/dirty enzyme is 1: 1) * * * 1.5
Fluorescent bleaches 0.5
Water, less important additive add to 100
* as Gelwhite GP(TM): CaCO 3Ion-exchange capacity is 70 milligramequivalents/100 grams
* presses the method preparation of example 1, and is sprayed onto on the product of making
* * and composition are done and are mixed.
The composition for preparing example 2 by example 1 described method.The composition that the composition of example 2 is replaced than the sodium sulfate that acid amides/the lauric acid complex compound has been added in addition wherein provides better flexibility.

Claims (10)

1, contain tensio-active agent and nitrogenous fabric softener, can contain the detergent composition of detergent additive when needing, it is characterized in that nitrogenous tenderizer is selected from the compound of following group:
Figure 87107303_IMG1
Wherein:
R 1, R 2, R 3And R 4All independently be selected from the C that may contain hydroxyl groups, ester group and/or ehter bond 12-22Alkane (alkene) base, aryl or alkaryl,
R 5Be selected from alkane (alkene) group of 1 to 10 of carbon atoms or be selected from aryl group, substituted aryl group, heteroaryl group, substituted heteroaryl group and polyaryl group, and R 5May contain a plurality of hydroxyl groups, ester group and/or ehter bond,
4) with 1) to 3) sulphonamide that described acid amides is corresponding.
2, according to the composition of claim 1, acid amides tenderizer wherein is with following dispersion agent dispersive in advance:
-by primary aliphatic alcohols or secondary alcohol polycondensation and nonionogenic tenside,
-chemical formula is R '-O(CH 2-CH 2O) mPO(OH) 2Phosphoric acid ester, R ' in the formula=C 12-C 14, and m=1-5,
The lipid acid of 10 to 20 carbon atoms of tool in the-alkyl chain.
3, according to the composition of claim 2, dispersion agent wherein is the lipid acid of 10 to 20 carbon atoms of tool in the alkyl chain, and is that weight ratio in acid amides tenderizer and lipid acid is that 1: 1 to 10: 1 ratio exists.
4, according to the composition among the claim 1-3, wherein R 1, R 2, R 3And R 4Be coconut alkyl or Tallow, beef alkyl.
5, according to the composition among the claim 1-4, nitrogenous tenderizer wherein has Chemical formula 2), and R 5Be C 1-5Alkyl.
6, according to the composition among the claim 1-5, nitrogenous tenderizer tool Chemical formula 2 wherein), and R 5Be phenyl or substituted phenyl.
7, according to the composition of claim 6, nitrogenous tenderizer wherein is four Tallow, beef terephthaloyl amine, or four coconut terephthaloyl amine.
8, according to the composition among the claim 1-7, wherein the content of nitrogenous tenderizer is 0.1% to 15% by weight.
9,, wherein also contain a kind of peroxy acid bleach compound according to the composition among the claim 1-8.
10, according to the composition of claim 9, peroxy acid bleach compound wherein comprises peroxy bleaching compound and its promoting agent.
CN198787107303A 1986-11-13 1987-11-13 The softening detergent compositions that contains specific poly-amide softening agent Pending CN87107303A (en)

Applications Claiming Priority (2)

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GB8627181 1986-11-13
GB868627181A GB8627181D0 (en) 1986-11-13 1986-11-13 Softening detergent compositions

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WO1992006984A1 (en) * 1990-10-12 1992-04-30 The Procter & Gamble Company Process for preparing n-alkyl polyhydroxy amines and fatty acid amides therefrom in hydroxy solvents
AU7246198A (en) * 1997-04-09 1998-10-30 Rhodia Inc. Nonionic gemini surfactants having hydrophilic sugar groups
US6306463B1 (en) * 2000-07-20 2001-10-23 Air Products And Chemicals, Inc. Citric acid tri-alkylamide surfactants
KR100405314B1 (en) * 2001-07-03 2003-11-12 주식회사 엘지생활건강 Preparation of non-ionic surfactants
DE102006036889A1 (en) * 2006-08-04 2008-02-07 Clariant International Limited Use of aminoacetones and their salts as bleaching force enhancers for peroxygen compounds
JP4873634B2 (en) * 2007-01-12 2012-02-08 株式会社コルグ Tuner
JP2020063435A (en) * 2018-10-11 2020-04-23 花王株式会社 Detergent composition for textile product

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DE3367617D1 (en) * 1982-02-04 1987-01-02 Unilever Plc Process for producing low-sudsing detergent compositions
ZA833292B (en) * 1982-05-11 1984-12-24 Unilever Plc Granules containing silicone-based anti-foam and a process for preparing them
GB8609884D0 (en) * 1986-04-23 1986-05-29 Procter & Gamble Softening detergent compositions
EP0258500A1 (en) * 1986-09-02 1988-03-09 Akzo N.V. Fabric softening composition and detergent-composition comprising the same

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EP0274142A3 (en) 1989-06-28
IE873056L (en) 1988-05-13
FI874996A (en) 1988-05-14
JPS63199294A (en) 1988-08-17
FI93468C (en) 1995-04-10
EP0274142A2 (en) 1988-07-13
DK598687A (en) 1988-05-14
GR3006782T3 (en) 1993-06-30
ATE84063T1 (en) 1993-01-15
KR880006352A (en) 1988-07-22
AU8115287A (en) 1988-05-19
GB8627181D0 (en) 1986-12-10
DK598687D0 (en) 1987-11-13
NZ222531A (en) 1990-11-27
FI93468B (en) 1994-12-30
EP0274142B1 (en) 1992-12-30
DK170117B1 (en) 1995-05-29
DE3783352T2 (en) 1993-05-13
FI874996A0 (en) 1987-11-12
DE3783352D1 (en) 1993-02-11

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