CA1245222A - Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain - Google Patents

Abstract

Abstract This invention relates to bleaching compounds and compositions that provide effective and efficient surface bleaching of textiles over a wide range of bleach solution temperatures. The bleaching compounds of the invention yield a peroxyacid with a polar amide link in the hydrophobic chain when used in the bleaching compositions.
In a preferred embodiment, the bleaching compositions of the invention are also detergent compositions. The compounds have the formula:
(A) (B) or wherein R1 is an alkyl, aryl or alkaryl group containing from about 1 to about 14 carbon atoms, R2 is an alkylene, arylene or alkarylene group containing from about 1 to about 14 carbon atoms, R5 is H or an alkyl, aryl or alkaryl group containing from about 1 to about 10 carbon atoms, X is a compatible anion, n is 1 or 2, and Y
is from 0 to about 6.

Description

3L2~L5Z22 BLE,9CIIING COMPOUNDS AND COMPOSITIONS COMPRISING
FATTY PEROXYACIDS SALTS THEREOF AND PRECURSORS
THEREFOR HAVINC AMIDE MOIETIES IN THE FATTY CHAIN
Michael E. 8urns 5Frederick E. Hardy BACKGROUND OF THE INVENTION
rechnical Field This invention relates to peroxygen bleaching compositions and processes therefor that provide effective bleaching of textiles 10 over a wide range of temperatures.
SUMMARY OF THE INVENTION
The present invention relates to a bleaching compound providing a peroxyacid of the following general formulas:
R1 _ C - N-R2- C OOH o r Rt _ N - C-R2-C - OOH
" 5 ' 5 ll il 15O~ R O R O O
wherein R1 and R2 are alkyl(ene), aryl(ene) or alkaryl(ene) groups containing from about 1 to about 14 carbon atoms and R5 is H or an alkyl, aryl, or alkaryl group containing from about 1 to about 10 carbon atoms.
20A group of compounds which provides the above peroxyacids are the magneslum salts of the peroxyacids of the following gene ral formu las:

25[R1 _ C - N-R2- C - 00 _~ ~,Ag X2-n YH2 _ _ _ ffr R1 _ N - C-R2- C - oo - Mg X2_n Y~20 L R5 O O - n 30 wherein R1, R2 and R5 are as defined for the peroxyacid, X is a compatible anion, n is one or two, and Y is from 0 to about 6.
The peroxyacids may also be formed in situ from a peroxygen bleaching compound capable of yielding hydrogen peroxide in aqueous solution and a bleach activator of the follow-35ing formulas:
R1 _ C - N-R2 -C - L o r Rl - N - C-R2 -C- L
" , " ' 5 "
O R` O R O O

- ?
.~

~2~5222 wherein R, R and K are as deflned for the peroxyacid, and L
is a leaving group.
The invention also relates to bleaching compositions which contain one of the above compounds. Where the composition 5 contains the bleach activator, another essential component is a peroxygen bleaching compound capable of yielding hydrogen peroxide in aqueous solution. In a preferred embodiment, the bleaching compositions are incorporated into detergent compositions .
ETAILED DESCRIPTION OF THE INVENTION
The invention relates to bleaching compounds which provide amide substituted peroxyacids of the following general formula:
R1 _ C - N-R2 - C - OOH o r R1 _ N - C-R2 -C - OOH
Il 15 ll 15 ll 1~
O R O R O O

wherein R1 is an aryl or alkaryl group with from about 1 to about 14 carbon atoms, R2 is an alkylene, arylene, and alkarylene group containing from about 1 to about 14 carbon atoms, and R5 is H or an alkyl, aryl, or alkaryl group containing 1 to 10 carbon 20 atoms. R1 preferably contains from about 6 to about 12 carbon atoms. R2 preferably contains from about 4 to about 8 carbon atoms. R1 may be straight chain or branched alkyl, substituted aryl or alkylaryl containing branching, substitution, or both.
Analagous structural variations are permissible for R2. The 25 substitution can include alkyl, aryl, halogen, nitrogen, sulfur, and other typical substituent groups of organic compounds. R5 is preferably H or methyl. R1 and R5 should not contain more than 18 carbon atoms total.
The bleaching compounds of the invention provide effective 30 and efficient surface bleaching of textiles which thereby removes stains and/or soils from the textiles. The compounds are particu-larly efficient at removing dingy soils from textiles. Dingy soils are those that build up on textiles after much usage and washing, and result in a gray or yellow tint on a white textile. These 35 soils are a blend of particulate and greasy materials.

~2~22 The compounds of the invention provide effective bleaching over a wide range of temperature (5C to 85C), a preferred range being from about 30C to about 60C.
The pres~nce of the polar amide or substituted amide moiety 5 results in a peroxyacid which has a very low vapor pressure and thus possesses a low ocior profile as w011 as an excellent bleaching performance .
The peroxyacid may be used directly a5 a bleaching agent.
The improved thermai stability of the peroxyacids of the 10 invention, especially when incorporated into the bleaching composltions and d~tergent compositlons described hereinafter is surprlsing, especially when compared to alkyl peroxyacids, especially the short chaTn peroxyacids of the prior art, e.g. U.S.
Patent 4,1~12,934, Chung et al.
VYhile not wishing to be bound by theory it is believed that the polarity of the amide group results in a reduction of vapor pressure of the peroxyacid, and a corresponding increase in melting point.
The substituted amide containing peroxyacids also have a 20 reduced vapor pressure, and show good odor profiles. These compounds are well suited for use in the bleach activator structures provided hereinafter.
The Magnesium Peroxycarboxylate The magnesium salt has the following general formulas:
[R1 _ C - N-R2- C - 00 - ] 9 X2-n YH2 _ _ _ 30 o r R1 _ N - C R2- C - ()0 _ Mg X2 -n YH2 R 0 0 n wherein R1, R2 and R5 are as defined for the peroxyacid, X is a compatible anion, n is 1 or 2, and Y is from 0 to about 6.
The compounds are solid and possess good storage under alkallne conditions such as when admixed with a detergant ,~,, ~, composition. The active oxygen Tn the magnesium peroxycarboxylate is readily avaitable. This means that the solid magnesium peroxycarboxylates are readily soluble or dispersible and yield solutions containing peroxyacids. When the solution is 5 aqueous, it cannot be distinguished from an aqueous solution prepared from the corresponding peroxyacid and an equivalent amount of magnesium, when the solutions are adJusted to the same pH ~
It is believed that the stability of the magnesium salt is due 10 to the fact that the active oxygen atorn Ts nucleophilic rather than electrophilic as it is in the corresponcling peroxycarboxylic acid, Nucleophiiic agents which would attack an electrophilic oxygen are much more prevalent In bleaching and detergent composition~ than electrophilic agents.
The magnesium peroxycarboxylates can be prepared via the process of U.S. Patent 4,483,7û1, Hartman, issued November 20, 1 984 .
The Bleach Activator The bleach activators within the invention are amide sub-20 stituted compounds of the general formulas:
Rl _ C - N-R2-C - L or R1 _ N - C-R2-C-L
" ' 5 " ' 5 " "
O R O R O O
wherein R1, R2 and R5 are as defined for the peroxyacid, and L
can be essentially any suitable leaving group. A leaving group is 25 any group that is displaced from the bleach activator as a consequence of the nucleophilis attack on the bleach activator by the perhydroxide anion. This, the perhydrolysis reaction, results in the formation of the peroxycarboxylic acid. Generally, for a group to be a suitable leaving group it must exert an 30 electron attracting effeet. It should also form a stable entity so that the rate of the back reaction is negligible. This facilitates the nucleophilic attack by the perhydroxide anion.
The L group must be sufficiently reactive for the reaction to 35 occur within the optimum time frame (e.g., a wash cycle~.
However, if L is too reactive, this activator will be difficult to stabilize for use in a bleaching composition. TS)ese characteristics , ~Z~5222 are generally paralieled by the pKa of the conjugate acid of the leaving group, although exceptions to this convention are known.
Ordinarily, leaving groups that exhibit such behavior are those in which their conjugate acid has a pKa in the range of from about 4 5 to about 13, preferably from about 6 to about 11 and most preferably from about 8 to about 11~
Preferred bleach activators are those of the above general formula wherein R, R and R are as defined for the peroxyacid and L is select~d from the group consistin~3 of:

_o~, o{~, _ O ~, -N-C-Y $

-N

O Y O
Il ~ 11 O ~C~l2---- C ~ - C
?.0 C/ ~ C/
ll 11 O O

-O-CH = C - CH = CH2, -O-CH = C - CH = CH;! ' 3û -O-C = C~IR4. ar'd - N - S - CH - R
3 I~
O

wherein R1 is as defined ~or the peroxyacid, R3 is an alkyl chain containina, from a~out 1 to about a carbon atoms, R4 is H or R3, and Y is H or a solubilizin~ group. The preferred solubilizing groups are -S03M, -COO M, -504 M, ~-N R4)X and o+N(R34) ~2~i222 and most preferabiy -S03M and -C90 M wherein R is an alkyl chain containing from about 1 to about 4 carbon atoms, M is a cation which provides solubility to the bleach activator and X is an anion which provides solubility to the bleach activator. Pref-5 erably, ~l is an alkali metal, ammonium or substituted ammoniumcation, with sodium and potassium being most preferred, and X is a halide, hydroxide, methylsulfate or acetate anion. It should be noted that bleach activators with a ieaving group that does not contain a solubilizing group should be well dispersed in the 10 bleaching solution in order to assist in their dissolution.
Preferred bleach activators are those wherein L is a lea~ing group as previously defined, R1 Is an alkyl group containing ~rom about 6 to about 12 carbon atoms, R is an alkylene group containing from about 4 carbon atoms to about 8 carbon atoms, 15 and R5 is H or methyl.
Particularly preferred bleach activators are those of the above general formula wherein R1 is an alkyl group and R2 is an alkylene group each containing from about 1 to about 14 carbon atoms, R5 is H, and L is selected from the group consisting of:

-0~ O~Y and -0~
wherein R3 Is as defined above and Y is -503M or -C00 M
wherein M is as defined above.
Especially preferred bleach activators are those wherein R1 is a linear allcyl chain containing from about 6 to about 12 carbon atoms, R2 is a linear alkylene chain containing from about 4 to about 8 carbon atoms, R5 is H, and L is selected from the group consisting of:

-0~, -O~Y and -0~
wherein R3 is as defined above and Y is -503M~ or -C00 M
wherein M is as defined above.
The Bleaching Compositions The bleaching compositions of the invention are those which, upon dissolution in aqueous solution, provide a bleaching com-pound of the formula ~2g~222 Rl - C - N-R2 - C - OOH o r R1 _ N - C-R2 -C - OOH
O ~5 O ~5 O O

wherein R1, R2 and R5 are as defilned for the peroxyacid, Such compositions provide extremely effective and efficient surface bleaching of textiles which thereby remove stains and/or soils from the textiles. The compositions are particularly effec-tive at removing dingy soils from textiles. Dingy soils are soils that build up on textiles after numerous cycles of usage and 10 washing, and- thus, result in a white textile having a gray or yellow tint. These soils tend to be blend of particulate and ~reasy materials. The remova! of this type of soii is sometimes referred to as "dingy fabric clean up".
The bleaching compositions provide such bleaching over a 15 wide range of bleach solution temperatures. Such bleaching is obtained in bleach solutions wherein the solution temperature is at - least about 5~C. Inorganic peroxygen bleaches would be ineffec-tive andlor impracticable at temperatures below about 60C.
This invention also relates to bleaching compositions contain-20 ing a peroxygen bleach capable of releasing hydrogen peroxide inan aqueous solution and specific bleach activators, hereinafter defined, at specific molar ratios of hydrogen peroxide to bleach activator .
The bleaching mechanism generally, and the surface bleach-25 ing mechanisrn in particular, are not completely understood.However, it is generally believed that the bleach activator under-goes nucleophilic attack by a perhydroxide anion, which is gen-erated from the hydrogen peroxide evolved by the peroxygen bleach, to form a peroxycarboxylic acid. This reaction is com-30 monly referred to as perhydrolysis.
When the activators are used, optimum surface bieachingperformance is obtained with bleaching solutions wherein the pH
of such solution is between about 8.5 and 10.5 and preferably between ~.5 and 10.5 in order to facilitate the perhydrolysis 35 reaction. Such pH can be obtained with substances commonly ~2~

known as bufferlng agents, which are optional components of the bleaching composittons herein.
It is also believed, that thc bleach actlvators within the invention can render peroxygen bleaches more efficient even at 5 bleach solution temperatures wherein bleach activators are not necessary to activate the bleach, i.e., above about 60C. There-fore, with bleach compositions of the invention, less peroxygen bleach is required to get the same level of surface bleaching performance as is obtained with the peroxygen bleach alone.
The bleaching compositions wherein the bleach activator is used also have, as an essential component a peroxygen bleach capable of releasing hydrogen peroxide aqueous solution. In these compositions the molar ratio of hydrogen peroxide yielded by the peroxygen bleaching compound to the bleach activa~or must be greater than about l.O and pre~erably greater than akout 1.5.
The Peroxygen Bleaching Compound The peroxygen bleaching compounds useful hereln are those capable of ylelding hydrogen peroxide in an aqueous solution.
20 These compounds are well known in the art and include hydrogen peroxide and the alkali metal peroxldes, organic peroxide bleach-ing compounds such as urea peroxide, and inorganic persalt bleachlng compounds, such as the alkali metal perborates, percar-bonates, perphosphates, and the like. Mixtures of two or more 25 such bleaching compounds can also be used, if desired.
Preferred peroxygen bleaching compounds include sodium perborate, commercially available in the form of mono-, tri- and tetra- hydrate, sodium carbonate peroxyhydrate, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, and sodium 30 peroxide. Particularly preferred are sodium perborate tetrahydrate and, especially, sodium perborate monohydrate.
Sodium perborate monohydrate is especially pre~erred because it is very stable during storage and yet still dissolves very quickly in the bleaching solutionO It is believed that such rapid dis-35 solution results in the formation of higher levels of percarboxylicacid and, thus, enhanced surface bleaching performance.
The level of bleach activator within the compositions of the invenSicn is from about 0.1% to about 6096 and preferably from about 0 . 596 to about 40%. When the bleaching compositions within ~, i.
~' ~2~52%2 g th~ invention are also detergent compositions it is preferred that the level of bleach activator is from about .5% to about 20%.

As a preferred embodiment, the bleaching compositions of the invention can be detergent compositions. Thus, the bleaching compositions can contain typical detergent composition components such as detergency sur~actants and deter~ency builders. In such preferred embodiments the bleaching compositions are particularly effective, The bleaching compositions of this invention can contain all of the usual components of detergent compositions including the ingredients set forth in U.5. Patent 3,936,537, Baskerville et al. Such ~om-ponents include color speckles, suds boosters, suds suppressors, antitarnish and/or anticorrosion agents, soil-suspending agents, soil-release agents, dyes, fillers, optical brighteners, germicides, alkalinity sources, hydrotropes, antioxidants, enzymes, enzyme stabilizing a~ents, per~umes, etc.
Enzymes are highly preferred optional ingredients and are incorporated in an amount of from about 0.02596 to about 5%, preferably from about 0.05% to about 1.5%. A proteolytic activity of from about 0,01 to about 0.05 Anson units per gram of product Is desirable. Other enzymes, including amylolytic enzymes, are also destrably included in the present compositions.
Suitable proteolytic enzymes include the many species known to be adapted for use in detergent compositions. Commercial enzyme preparatlons such as "Alcalase" sold by Novo Industries, and "Maxatase" sold by Gist-Brocades, Delft, The Netherlands, are suitable. Other preferred enzyme compositions include those commercially available under the trademark~ SP-72 ("Esperase") manufactured and sold by Novo Industries, A/S, Copenhagen, :

~522~

Denmark and AZ-Protease manufactured and sold by Gist-Brocades, Delft~ The Netherlands.
Suitable amylases include P~apidase sold by Gist-Brocades and Termamyl sold by Novo Industries.
A more complete disclosure of suitable enzymes can be found in U.S. Patent 4,101,457, Place et al, issued July 18, 1978.

The detergent surfactants can be any one or more surface active agents selected from anionic, nonionic, zwitterionic, ampho-teric and catlonic classes and compatible mixtures thereof. Det~r-gent surfactants useful herein are listed 5n U . S . Patent 3,664,961, Norris, issued May 23, 1972, and in U.S. Patent 3,919,678, Laughlin et al, issued December 30, 197~.
Useful cationic surfactant~ also include those described in U.S. Patent 4,222,905, Cockrell, issued September 16, 1980, and in U.S. Patent 4,239,659, Murphy, Issued December 16, 1980.
The following.are representa.tive examples of deter-gent surfactants useful in the present compositions.
Water-soluble salts of the higher fatty aclds, i.e., soaps, are useful anionic surfactants in the composltions herein. This Includes alkali metal soaps such as the sodium, potassium, ammon-25 ium, and alkylolammonlum salts of higher fatty acids containingfrom about 8 to about 24 carbon atoms, and preferably from about 12 ~o about 18 carbon atoms. Soaps can be made by direct saponification of fats and oils or by the neutralization of free fatty acids. Particularly useful are the sodium and potassium 30 salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e,, sodlum or potassium tallow and coconut soap.
Useful anionic surfactants also include the water-soluble salts, preferably the alkali metal, ammonium and alkylolammonium salts, of organic sulfurtc reaction products having in their molec-35 ular structure an alkyl ~3roup containing from about 10 to about20 carbon atoms and a sulfonlc acid or sulfuric acid ester group.
(Included in the term alkyl is the alkyl portion of acyl groups.) Examples of this group of synthetic surfactants are the sodium ,~ 1.
,., j i ~Z~2;2;~

and potassium alkyl sulfates, especially tho5e obtained by sulfat-ing the higher alcohols (C8-C18 carbon atoms) such as those produced by reducing the glycerides of tallow or coconut oil; and the sodium and potassium alkylbenzene sulfonates in which the 5 alkyl group contains from about 9 to about 15 carbon atoms, in straight chain or branched chain configuration, e.g., those of the type described in U.S. Patents 2,220,099 and 2,477,383. spec-ially valuable are linear straight chain alkyib~nzene sulfonates in which the average number of carbon atoms in the alkyl group is from about 11 ~o 13, abbreviated as C11 13LAS.
Other anionic surfactants herein are the sodium alkyl gly-ceryl ether sulfonates, especially those ethers of higher alcohols derived from tallow and coconut oil sodium coconut oil fatty acid monoglyceride sulfonates and sulfates; sodium or potassium salts 15 of alkyl phenol ethylene oxide ether sulfates containing from about 1 to about 10 units of ethylene oxide per molecule and wherein the alkyl groups contain from about 8 to about 12.carbon atoms; and sodium or potassium salts of alkyl ethylene oxide ether sulfates containing about 1 to about 10 units of ethylene oxide 20 per molecule and wherein the alkyl group contains from about 10 to about 20 carbon atoms.
Other useful anionic surfactants herein include the water-soluble salts of esters of alpha-sulfonated fatty acids containing from about 6 to 20 carbon atoms in the fatty acid group and from 25 about 1 to 10 carbon atoms in the ester group; water-soluble salts of 2-acyloxyalkane-1-sulfonic acids containing from about 2 to 9 carbon atoms in the acyl group and from about 9 to about 23 carbon atoms in the alkane moiety; water-soluble salts of olefin and paraffin sulfonates containing from about 1~ to 20 carbon 30 atoms; and beta-alkyloxy alkane sulfonates containing from about l to 3 carbon atoms in the alkyl group and from about 8 to 20 carbon atoms in the alkane moiety.
Water-soluble nonionic surfactants are also useful in the 35 compositions of the invention. Such nonionic materials include compounds produced by the condensation of alkylene oxide groups lhydrophilic in nature) with an organic hydrophobic compound, Z~5222 which may be aliphatic or alkyl aromatic in nature. The length of the polyoxyalkylene group which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
Suitable nonionic surfactants include the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group contalning from about 6 to 15 carbon atomst in either a straight chain or branched chain con-figuration, with from about 3 to 1~ moles of ethylene oxide per mole of alkyl phenol.
Preferred nonionics are the water-soluble and water-disper-sible condensation products of aliphatic alcohols containing from 8 to 22 carbon atoms, in either straight chain or branched config-uration, with from 3 to 12 moles of ethylene oxide per mole of alcohol. Particularly preferred are the condensation products of alcohols having an alkyl group containing from about 9 to 15 carbon atoms with from about 4 to 8 moles of ethylene oxide per mole of alcohol, Serni-polar nonionic surfactants include water-soluble amine oxides containing one alkyl moiety of from about 10 to 18 carbon atoms and two moieties selected from the group of alkyl and hydroxyaikyl moieties of from about 1 to about 3 carbon atoms;
water-soluble phosphine oxides containing one alkyl moiety of about 10 to 18 carbon atoms and two moieties selected from the group consisting of alkyl groups and hydroxyalkyl groups con-taining from about 1 to 3 carbon atoms; and water-soluble sulf-oxides containing one alkyl moiety of from about 10 to 18 carbon atoms and a moiety selected from the group consisting of alkyl and hydroxyalkyl moieties of from about 1 to 3 carbon atoms.
Ampholytic surfactants include derivatives of aliphatic or aliphatic derivatives of heterocyclic secondary and tertiary amines in which the aliphatic moiety can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and at least one aliphatic substituent con-tains an anionic water-solubilizing group.

~2~5;~22 Zwitterionic surfactants inciude derivatives of allphatic, quaternary, ammonium, phosphonium, and 5ulfonium compounds In which one of the aliphatic substituents contains from about S to 18 carbon atcms.
The level of detergent surfactant that can be employed is from 0% to about 50%, preferably from about 1% to about 30% and most preferably from abcut 10% to about 259~ by weight of the total cornposition.
In addition to detergent surfactants, deter~ency builders can be employed in- the bleaching compositions. Water-soluble inor-ganic or organic electrolytes are suitable builders. The builder can also be water-insoluble calcium ion exchange materials; non-limiting examples of suitable water-soluble, inorganic detergent builders include: alkali metal carbonates, borates, phosphates, bicarbonates and silicates. Specific examples of such salts include sodium and potassium tetraborates, bicarbonates, carbonates, orthophosphates, pyrophosphates, tripolyphosphates and meta-phosphates .
Examples of suitable organic alkaline detergency builders Include: t1 ) water-soluble amino carboxylates and aminopolyace-tates, for example, nitrilotriacetates, glycinates, ethylenedia-mlnetetraacetates, N-(2-hydroxyethyl)nitrilodiacetates and diethyl-enetriaminepentaacetates; (2) water-soluble salts of phytic acid, for example, sodium and potassium phytates; l3) water-soluble polyphosphonates, including sodium, potassium, and lithium salts o~ ethane-1-hydroxy-1, 1-diphosphonic acid; sodium, potassium, and lithium salts of ethylene diphosphonic acid; and the like; (4) water-soluble polycarboxylates such as the salts of lactic acid, succinic acid, malonic acid, maleic acid, citric acid, carboxy-30 methyloxysuccinic acid, 2-oxa-1, t, 3-propane tricarboxylic acid, 1,1,2,2-ethane tetracarboxylic acid, mellitic acid and pyromellitic acid; and ~5) water-so~uble polyacetals as disclosed in U.S.
Patents 4 ,144, 266 and 4, 246, 495, Another type of detergency builder material useful in the present compositions comprises a water-soluble material capable of forming a wat~r-insoluble reaction product with water hardness

2;~2 cations preferably in combination with a crystallization seed which is capable of providing growth sltes for said reaction product, Such seeded builder compositions are fully disclosed in British Patent Specification No. 1,424,406.
A further class of detergency builder materials useful in the present invention are insoluble sodium aluminosilicates, particu-larly those described in Belgian Patent S14,874, issued November 1~, 1974. This patent discloses and claims detergent compositions contalning sodium aluminosili-1~ cates having the ~ormula:
Naz(Alo2)z(sio2)yxH~o wherein z and y are integers equal to at least 6, the molar ratio of z to y is in the range of from 1.0:1 to about 0.5:1, and X is an integer from about 15 to about 264, said aluminosilicates hav-ing a calcium ion exchange capasity of at least 200 millTgrams equivalent/gram and a calcium ion exchange rate of at least about 2 grainslgallon/minute/gram. A preferred material is Zeolite A
which is:
Na1 2~S~02A12) 1 227H2 The level of detergency builder of the bleaching compositions is from 0% to about 7096, preferably from about 10% to about 60%
and most preferably from about 20% to about 60%.
Buf~ering agents can be utillzed to maintain the desired alkaline pH of the bleaching solutions. Buffering agents include, but are not limited to many of the detergency builder compounds disclosed hereinbefore. Buffering agents suitable for use herein are those well known in the detergency art.
Preferred optional ingredients include suds modifiers parti-cularly those of suds suppressing types, exemplified by silicones, and silica-silicone mixtures.
U.5. Patents 3,933,672, issued January 20, 1976 to Bartolotta et al, and 4,136,045, issued January 23, 1979 to Gault et al, disclose silicone suds controlling agents. The silicone material can be represented by alkylated polysiloxane materials such as silica aerogels and 522~

,5 xerogels and hydrophoblc sllicas of various types. The silicone material can be described as siloxane havlng the formula:
_ __ - SiO~ _ R x wherein x is from about 20 to about 2,000 and each R is an alkyl or aryl group, especially methyl, ethyl, propyl, butyl and phenyl groups. The polydirne~hylsiloxanes (both Rs are methyl) havlng a moleoular weight wlthin the range of from about 200 to about 2,000,000, and higher, are all useful as suds controlling agents.
Additional suitable silicone rnaterials wherein the side chain groups R are alkyl, aryl, or mixed alkyl or aryl hydrocarbyl groups exhibit useful suds controlling properties. Examples of the like ingredients include diethyl-, dipropyl-, dibutyl-, methyl-, ethyl~, phenylmethylpoly-siloxanes and the like. AddT-tional useful silicone suds controlling agents can be represented ~y a mixture of an alkylated siloxane, as referred to hereinbe-fore, and solid sillca. Such mixtures are prepared by affixing the silicone to the surface of the solid silica. A preferred sili-cone suds controlling agent is represented by a hydrophobic silanated tmost preferably trimethylsilanated) silica having a partlcle size in the range from about l O millimicrons to 20 milli-microns and a specific surface area above about 50 m21gm. inti-mately admixed with dimethyl sllicone fluid having a molecular welght in the range from about 50~ to about 200,000 at a weight ratlo of silicone to silanated silica of from about 19:1 ~o about 1: 2, The sillcone suds suppressing agent is advantageously releasably incorporated in a water-soluble or water-dispersible, substantially nan-surface-active detergent-impermeable carrier.
Particularly useful suds suppressors are the self-emulsifying silicone suds suppressors, described in U.S. Patent 4,073,118, Gault et al, issued February 21, 1978, An example of such a compound is DB-544, commer-cially available from Dow Corning, which is a siloxane/glycol copolyrner.

~24SZ;~2 Suds modifiers as described above are used at levels of up to approximately 2%, preferably from about 0.1 to about 1~% by weight of the surfactant.
Microcrystalline waxes having a melting point in the range from 35C-115C and a saponification value of less than 100 represent additional examples of pref~rred suds control compon-ents for use in the subject compositions, and are described in detall In U.S. Patent 4,056,481, Tate, issued November 1, 1977, The microcrystalline waxes.are 10 substantially water~insoluble, but are water-dispersible in the presence of organic surfactants. Preferred microcrystalline waxes have a melting point from about 65C to 100C, a molecular weight in the range from 400-1,000; and a penetration value of at least 6, measured at 77F by ASTM-D1321. Suitable examples of the 15 above waxes include: microcrystalline and oxidized microcrystal-line petroleum waxes Fischer-Tropsch and oxidized Fischer-Tropsch waxes; ozokerite; ceresin; montan wax; beeswax; cande-lilla; and carnauba wax.
Alkyl phosphate esters represent an additional preferred 20 suds control agent for use herein. These preferred phosphate esters are predomlnantly monostearyl phosphate which, in addition thereto, can contain dl- and tristearyl phosphates and monooleyl phosphate, which can contain di- and trioleyl phosphate.
Other suds control agents useful in the practice of the 25 invention are the soap or the soap and nonionic mixtures as disclosed in IJ.S. Patents 2,954,347 and 2,954,348~

This invention also relates to the process of bleaching tex-tiles with a compound which, when in aqueous solution, yields a 30 peroxyacid of the following formulas:
Rl _ C - N-R2- C - OOH or R1 - N - C-R2-C - OOH
Il I c P
O R' O R' O O

wherein R and R are alkyl aryl or alkaryl groups w7th from 35 about 1 to about 14 carbon atoms, and R5 is H or an alkyl, aryl or alkaryl group containing from about 1 to about 10 carbon atoms .
The following examples are given to illustrate the parameters of and compositions within the inventionO All percentages, parts and ratios are by weight unless otherwise indica~ed.
EXAMPLE I
Preparation of N-Lauroyl-6-Aminoperoxycaproic Acid A one beaker was charged with 250 mL of I N sodium hydroxide solu~ion (0.25 mol) and 32.8 g (0.25 mol) of 6-aminocaproic acid. The resulting solution was cooled in an ice bath and, with stirring, a solution of lauroyl chloride (54.7 g, 0.25 mol) in 100 mL ether was added dropwise while maintaining the pH of the stirred solution between 10 and 12 by addition of 1096 sodium hydroxide solution. Addition of the lauroyl chloride required 45 min. During this period the reaction mixture became thick with solid and additional volumes of water and ether were added in order to keep the mixture stirrable. Following completion of the lauroyl chloride addition, the it~e bath was removed and the mixture was stirred for 1 . 5 hr. at room temperature. The mixture was then adjusted to pH 2 with concentrated HCI, and the precipitate which formed was removed by filtration and washed with water. The resulting solid was slurriecl with hexane ~200 ml), filtered, and washed 5 times with 100 ml portions of hexane. This hexane slurrylwash procedure was repeated a second time. The resulting solid was air dried to yield 70.7g ~90%) of N-lauroyl-6-aminocaproic acid, mp 87-90C.
~lit mp 85-86C - E. Jungerman, J. F. Gerecht, and 1. J. Krems, J. Arner. Chem. ~oc., 78, 172 (1956) . ]
N-Lauroyl-6-Aminoperoxycaproic Acid A 25û mL beaker was charged with 35 . O g ~0 .112 mol ) of N-lauroyl-6-aminocaproic acid and 70 mL of 98% methanesulfonic acid. The resulting solution was cooled in an ice bath and, with stirring, 21.2 g of 90% hydrogen peroxide (19.0 g, 0.559 mol of hydrogen peroxide) was added dropwise at a rate so that the temperature of the reaction mixture did no~ rise above 20C

~Z~ 2 ~required 15 min. ) . The resu3ting solution was stirred at room temperature for 3 hrs., cooled to -15C, and poured over ice.
Ethyl acetate ( 150 mL) was added, the mixture was warmed to 60C. in a water bath, and the water layer separated. An 5 additionai 100 mi of water was added, the solution again warmed to 60C. and the water layer separated and discarded. The ethyl acetate solution was cooled to -15C., and the crystals which formed were removed by fiitration and washed with 2 X 50 mL
portions of -1 5C. ethyl acetate . The yield of 10 N-lauroyl-6-aminoperoxycaproic acid was 33~1 g; analysis for availa~le oxygen (AvO) indicated 4.31% ~theoretical yield = 36.9 g having an f~vO of ~.86%), mp 70-75C.
EXAMPLE I I
Preparation of N-Decanoyl-6-Aminoperoxycaproic Acid N-Decanoyl-6-Aminocaproic Acid N-decanoyl-6-aminocaproic acid was prepared by reaction of decanoyl chloride with 6-aminocaproic acid according to the procedure described in Example 1. From 95.4 g ~0.500 mol) of decanoyl chloride and 65.6g (0.500 mol) of ~-aminocaproic acid was obtained 140 g (98%) of N-decanoyl-6-aminocaproic acid, mp 73-7~C .
N-Decanoyl-6-Aminoperoxycaproic Acid A 400 mL beaker was charged with 100 mL of 98%
methanesulfonic acid and S00 9 ~0.175 rnol) of 25 N-decanoyl-6-aminocaproic acid. The resulting solution was cooled in an ice bath and, with stirring, 33.1 y of 9096 hydrogen peroxide (29 . 8 9, 0. 877 mol of hydrogen peroxide) was added dropwise at a rate such that the temperature of the reaction mixture did not rise above 20C. The addition required a total of 30 10 min. The resulting mixture was stirred at room temperature for 3 hrs., cooled to -15C, and poured into 500 mL of ice water.
The precipi~ated solid was extracted into 200 mL methylene chloride. The methylene chloride solution was separated, washed with 100 mL portions of water until the wash water was neutral ~6 35 washings required3, dried over sodium sulfate, and evaporated on a rotary evaporator to yield 51.6 9 of white solid having a ~Z~5222 peroxyacid AvO of 4.93% ltheoretical yield = 52.7 9 of AvO
5 .32~6) .
The N-decanoyl-6-aminoperoxycaproic acid was further purified by recrystallization from 200 mL of ethyl acetate 5 (dissolved in ethyl acetate at 60C ., then cooled to -1 5C. ) to yield 47 . 2 9 having a peroxyacid AYO of 5 .12%, and a mp of 63-67C .
EXAMPLE l l I
Preparation of N-Nonanoyl~6-Aminoperoxycaproic Acid N-Nonanoyl-6-Aminocaproic Acid N-nonanoyl-6-aminocaproic acid was prepared by reaction of nonanoyl chloride with 6-aminocaproic acid according to the procedure described in Example 1. From 67.3 9 (0.381 mol) of nonanoyl chloride and 50.0 g (0.381 mol) of 6-aminocaproic acid 15 was obtained 103 g of N-nonanoyl-6-aminocaproic acid, mp 71 -74C.
- N-Nonaoyl-6-Aminoperoxycaproic Acid N-nonanoyl-6-aminoperoxycaproic acid was prepared by reaction of N-nonanoyl-6-aminocaproic acid with hydrogen 20 peroxide in 98% methanesulfonic acid according to the procedure described in Example ll. From 103 g (0.381 mol) of N-nonanoyl-6-aminocaproic acid, 44 g ~1.29 mol) of hydrogen peroxide, and 170 mL of methanesulfonic acid was obtained 74.2 9 of N-nonanoyl-6-aminoperoxycaproic acid having a peroxyacid AvO
of 5.319~ and a mp of 60C (theoretical yield = 109.5 9 of 5.57%
AvO) .
EXAMPLE IV
Preparation of N-Lauroylaminoperoxyacetic Acid N-Lauroylglycine N-Lauroylglycine was prepared by reaction of iauroyl chloride with glycine according to the procedure described in Example 1. From 109.4 ~ (0.500 mol) of lauroyl chloride and 37.6 9 l0.500 mol) of glycine was obtained 120.5 g ~94%) of N-lauroylglycine, mp 110-118C, lit mp 118-119C lE. Jungerman, J. F. Gerecht, and 1. J. Krems, J. Amer. Chem. Soc., 78, 172 (1956~] .

S;~2~

N-Lauroylaminoperoxyacetic Acid N-Lauroylaminoperoxyacetic acid was prepared by reaction of N-lauroylglycine with hydrogen peroxide in methanesulfonic acid according to the procedure described in Example ll. From 50.09 (0.195 mol) of N-lauroylglycine and 33.1 9 (0.973 mol) of hydrogen peroxide in 100 mL methanesulfoni acid was obtained 38.0 g of N-lauroylaminoperoxyacetic acid having an AvO of 3.03%
(theoretical yield = 53.2 g having an AvO of 5.86%)~
EXA~PLE V
~ Preparation of N-Decanoylaminoperoxyacetic Acid N-Decanoy~ycine N-Decanoylglycine was prepared by reaction of decanoyl chloride with glycine according to the procedure described in Example 1. From 47.7 g (0.25 mol) of decanoyl chloride and 18.8 g (0.25 mol) of glycine was obtained 54.1 ~ (94%) of N-decanoylglycine mp 104-108C.
. N-Decanoylaminoperoxyacetic Acid N-Decanoylaminoperoxyacetic acid was prepared by reaction of N-decanoylglycine with hydrogen peroxide in methanesulfonic acid according to the procedure described in Example l l . From 22.9 g (0.100 mol) of N-decanoylglycine and 17.0 g (0.500 mol) of hydrogen peroxide in 50 mL methanesulfonic acid was obtained 22 . 4 g of peroxyacid having an AvO of 6 . 06% (theoretical yield =
24.5 9 having an AvO of 6.53%) mp 75-80C (melts with gas evolution).
EXAMPLE Vl Preparation of N-Decanoy~-4-Aminophenylperoxyacetic Acid N-Decanoyl-4-Aminophenylacetic Acid N-Decanoyi-4-aminophenylacetic acld was prepared by reaction of decanoyl chloride with 4-aminophenylacetic acid according to the procedure described in Example 1. From 63.1 9 (0.331 mol) of decanoyl chloride and S0.0 g l0.331 mol3 of 4-aminophenylacetic acid was obtained N-decanoyl-4-aminopheny3-acetic acid mp 156-159C.

~2~ 2~

N-Decanoyl-4-Amlnophenylperoxyacetic Acid N-Decanoyl-4-aminophenylperoxyacetlc acid was prepared from N-decanoyl-4-amlnophenylacetic acid and hydrogen peroxide in methanesulfonic acid according to the procedure described in Example l l . From 70.0 g (0.229 mol~ of N-decanoyl-4-aminophenylacetic acid and 39.0 g (1.15 mol~ of hydrogen peroxide in 1 S0 mL 98% methanesulfonic acid was obtalned 64 . 9 g of N-decanoyl-4-aminophsnylperoxyacetic acid having an AvO of 4.9496 (theoretical yield = 73.6 9 gaving an AvO
of l~.99%), mp 121C, EXAMPLE Vll Preparation of 6-Dec~amino-6-Oxoperoxycae~ic Acid 5- arbomethoxyvaleryl Chloride This ester/acid chloride was prepared as described in Org.
Synthesis Coll. Vol. 4, 556 ~1963).

Adipic acid, monomethylester (50.0 9, 0.312 mol) and thionyl chloride t74.3 9, 0.624 mol) were added to a 125 mL Erlenmeyer flask. The flask was fitted with a drying tube and the mixture 20 was allowed to stand at room temperature overnight in a hood.
Heptane ~100 rnL) was added and the excess thionyl chloride was removed on a rotary evaporator. An additional 50 mL of heptane was added and the resulting mixture again evaporated on a rotary evaporator to yield 56.4 9 of 5-carbomethoxyvaleryl chloride as a 25 yellow oil.
6-Decylamino-6-OxocaE~oic Acid, Methyl Ester A one L beaker fitted with a mechanical stirrer, ice bath, and pH eleetrode, was charged with 350 mL of water and 49.1 9 (0.312 mol) of decylamine in 100 mL ether. To this stirred 30 mixture was added dropwise a solution of the above 5-carbomethoxyvaleryl chloride in 100 mL ether, concurrent with dropwise addition of 20% sodium hydroxide solution so that the pll of the aqueous layer remained between 10 and 12. Total addition tirne was 30 min. Following addition of the acid chloride and 3s base, the precipitated solid was removed by fi!tration and washed with 300 mL hexane. The solid was then stirred with 200 mL
hexane, filtered, and washed with 100 mL portions of hexane.

522~

After air drying the weight of 6-decylamino-6-oxocaproic acid, methyl ester, was 5608 g, mp 56-59C.
An additional 19.1 9 of 6-decylamino-6-oxocaproic acid, methyl ester, was obtained from the filtrate by filtering and 5 washing the collected solid with hexane.
6-Decylamino-6-Oxoperoxycaproic Acid 6-Decylamino-6-oxoperoxycaproic acid was prepared according to the procedure described in Example I for N-decanoyl-6-amino-peroxycaproic acld. Thus, the methyl ester of 6-decylamino-6-oxocaproic acid (29.9 g, 0010 mol), hydrogen peroxide (17.0 9, 0.50 mol~, and 98% methanesulfonic acid (60 mL~ were reacted at room temperature for 2 hrs., the reaction mixture poured over ice, and the peroxyacid extracted into 125 mL of 60C. ethyl acetate. The aqueous layer was discarded and the warm ethyl acetate solution was washed with two 100 mL portions of water.
The ethyl acetate so!ution was transferred to a 250 mL Erlenmeyer flask (rinsed with 25 mL ethyl acetate), reheated to 60C.-, and then cooled to -1 5C . The crystals of N-decylamino-6-oxoperoxy-caproic acid were collected by filtration, washed twice with 50 mL
of ice~cold ethyl acetate and air dried. Yield was 21.6 g having peroxyacid AvO of 4.49~ (theoretical Yield = 30.1 g of 5,32%
AvO), and mp 77-85C.
EXAMPLE Vlll Preparation of 6-Nonylamino-6-Oxoperoxycaproic Acid 5-Carbomethoxyvaleryl Chloride 5-Carbomethoxyvaleryl chloride was prepared as described in Example Vll. From 100 g (0.624 mol) of the monomethylester of adipic acid and 148.6 g (1.248 mol) of thonyl chloride was obtained ltl.5 g (0.624 mol) of the ester/acid chloride as a yellow oil.
6-Nonylamino-6-Oxocaproic Acid, Methyl Ester The esterlacid chloride obtained above was reacted with nonylamine using the procedure described in Example Vll for the preparation of 6-decy3amino-6-oxocaproic acid, methyl ester.
From 111.5 g 10.624 mol of S-carbomethoxyvaleryl chloride and ~ 5;~2 89.1~ 9 ~0.624 mol) of nonylamine was obtained the methylester of 6-nonylamino-6-oxocaproic acid, 6-Nonylamino-6-Oxoperoxycaproic Acid 6-Nonylamino-6-oxoperoxycaproic acid was prepared 5 according to the procedure described in Example Vll for the decylamino derivative. From 100 9 (0.350 mol) of the monomethylest~r of 6-nonylamino-6-oxocaproic acid, 59.6 9 (1.75 mol ~ of hydrogan peroxide, and 300 mL of 9896 methanesulfonic acid was obtained 8'~.7 9 of 6-nonylamino-6-oxoperoxycaproic acid of AvO ltheoretical = 100,7 9 and 5.579~ AvO), and having -mp 83-87C.
EXAMPLE I X
Preparation of 6-E~enzoylam~aproic Acid b~
PerhvdrolYsis of Phenolsulfonate Est~r of 6-Benzo~lamin~proic Acid 6-Benzoylaminocaeroic Acid A 500 mL three-neck flask was fitted with mechanical stirrer, reflux condenser, and nitrogen inlet tube. The flask was flushed with nitrogen and charged with 35.3 9 ~0.15 mol) of 20 6-benzoylaminocaproic acid lOr~ Synthesis Coll. Vol.__2, 76 ~ î943), and 150 ml toluene.
To the resultlng stlrr~d suspension was added 23 . 3 mL ( 34 . 7 9, 0.165 mol) of trlfluoroacetic anhydride (Fisher) via a syringe.
The suspended solid rapidly dissolved. To this solution was ~s added 29.q 9 tO.15 mol) of anhydrous sodium p-phenolsulfonate.
The resulting suspension was heated at reflux for 2 . 5 hrs., cooled in an ice bath, and the precipitated soiid was filtered and washed well with ether. After air drying the solid was slurried with 125 mL ethanol, filtered, and washed with ethanol. The 30 resulting white paste was dried under Yacuum to give 43.7 9 of a hard, white solid. This solid was ground and passed thru 24 mesh screen. Analysis of the nmr spectrum (methyl sulfoxide -d6 soivent~ of this solid indicated that it contained 69% of the sodium salt of the phenolsulfonate ester o~ 6-benzoylaminocaproic acid and 35 31% sodium p-phenolsulfonate.

,, ~,,~

522;~

6-Benzoylaminoe~roxycaproic Acid Perhydrolysis of the above phenolsulfonate ester to yield 6-benzoylaminoperoxycaproic acid was accomplished according to the following procedure. To 4 L of 95F. city water was added 5.00 g (1250 ppm) of an alkaline detergent yranule, 0.36 9 (90 ppm) of sodium perborate monohydrate and 0.46 g (115 ppm) of the sodium salt of the phenolsulfonate ester sf 6-benzoylaminocaproic acid (0.67 g of the 69% mixture described above). Perhydrolysis of the ester to form 6-benzoylamino-peroxycaproic acid was followed by analysis of the solution for available oxygen (AvO) using a conventional iodometric titration. Complete conversion of the ester to the peroxyacid would result in the formation of 4 . 5 ppm AvO . The results obtained for AvO versus time are tabulated below.
% of theoretical Time (min. ) AvO (ppm) AvO
2 3.0 67 7 3.2 71 20 12 3,3 73

3.0 67 EXAMPLE X
Preparation of the Magnesium Salt of N-Decanoy!-6-Aminoperoxycaproic Acid A suspension of 2.92 g (0.050 mol) of magnesium hydroxide was prepared by adding 100 mL of IN sodium hydroxide (0.10 mol) to a solution of 6.02 g (0.050 mol) of magnesium sulfate in 25 mL water. The resulting suspension was added over a 1 min.
period to a warm, stirred solution of 30.1 9 ~0.10 mol) of N-decanoyl-6-aminoperoxycaproic acicl in 150 mL ethyl acetate~ A
heavy precipitate formed immediately. The mixture was stirred for 3 min., filtered, and the collected solid washed with water and ethyl acetate. The weight of magnesium bis-~N-decanoyl-6-aminoperoxycaproate~ was 31.7 g, with an available oxygen ~AvO) of 3.94%.

EXAMPLE Xl Stability of N-Decanoyl-6-Aminoperoxycaproic Acid The stability of N-decanoyl-6-aminoperoxycaproic acid was determined, both alone and admixed with an alkaline detergent 5 granule, at a variety of temperatures and humidities. The samples were stored in glass jars having vented tops. The activity of the remaining peroxyacid was determined by conventional iodometric titration for available oxygen. Samples which were admixes of peroxyacid and alkaline detergent granules 10 consisted of 7% peroxyacid and 93% detergent granule. The - results of this testing are tabulated below.
Stability ~f N-Decanoyl-6-Aminoperoxycaproic Acid % of Original Activity ~Stored Alone) Storage 80F/ 80F/
15 Time 15~ 60%
(Weeks)80F 100F 120F R.H. R.H.
. _

4 100 99 89 100 96 1 4 97 û6 7 76 99 % of Original Activity (Stored .
Storage 80F/ 80F/
25 Time 15% 60%
Weeks)80F 100F 1Z0F R.H. R.H.
96 98 9û 96 93 ~ 1 01 88 66 ~ 81 Bleaching Performance_ of N-Deca~noperoxycaproic Acid The bleaching performance of N-decanoyl-6-aminoperoxy-caproic acid was determined in a series cf experim~nts which compared the fabric whitening and stain removal of a treatment ~2~222 containing an alkaline detergent granule plus the peroxy acid, with a treatment containing the detergent granule alone.
Thus, to each of two top-loading automatic washing machines was added 5 Ibs. of naturally soiled ballast fabrics and 68 liters

5 of 95F city water having a hardness of 6 gr/gal, To one machine was added 89 g of an alkaline detergent granule and sufficient N-decanoyl-6-aminoperoxycaproic acid to result in an available oxygen (AvO) level of 3.5 ppm in the wash solution.
l o the second machine was added only 89 g of the alkaline 10 detergent granule.
To each of the above wash solutions were added two sets of naturally soiled white fabrics and two sets of artificially stained swatches. The washing machines were then allowed to complete their normal washing and rinsing cycles, and the ballast and test 15 fabrics were dryer dried. This procedure was repeated three times, using different sets of ballast fabrics, naturally soi!ed white fabrics and artificially stained swatches for each replicate.
After completion of the three replicates, the fabrics and swatches were arranged under suitable lighting for comparison of 20 soil and stain removal. Three expert graders compared the extent of removal of the soils and stains using the following scale:
0 no difference between two swatches thought to be a difference 2 certain of a difference 3 certain of a large difference 4 certain of a very large difference In this grading the naturally soiled white fabrics were compared for improvement in whiteness, and the artificially 30 stained swatches were compared for removal of the stain. The grades obtained were then averaged and normalized to yield the results shown below.

~2~ ;Z 2 Treatment and Average Relative Grade Detergent Granule +
Detergent3.5 ppm AvO From C;ranule N-Decanoyl-6-AloneAminoperoxycaproic Acid Naturally Soiled Fabrics T-shirts 0 2.4 s Dish towels 0 1.1 s Pillowcases 0 2 . 2 s Artificially Stained Fabrics Clay 0 0 . 4 Spaghetti sauce 0 0.1 Barbecue sauce 0 -0.4 Tea - 3 3 5 Grass 3-Nlenstrual blood 0 0 . 4 Blueberries 0 1.7 s 20 s = statistically significant difference (confidence level of 90%) relative to the detergent granule alone treatment EX AMPLE X I l l Bleachin~ Performance of Ma~3nesium Bis (N-Decanoyl-6-Aminoperoxyca~roate) The bleaching performance of the magnesiumsalt of N-clecanoyl-6-aminoperoxycaproic acid was determined using the procedure described in Example Xll. The magnesium salt was added to the wash solution as a finely divided powder suspended in 50 mL methanol. The amount of magnesium salt added was that 30 which provided a peroxyacid available oxygen tAYO) level of 3.5 ppm.
The results obtained ~or this bleaohing performance test are shown below.

-` ~Z~222 Treatment and Average Relative Grade Detergent Granule +
Detergent 3.5 ppm AvO From Granule Magnesium Bis Alone ( N-Decanoyl-6-Aminoperoxycaproate) Naturally Soiled Fabr~cs T-shirts 0 1.4 s Dish towels o ~.9 5 Pillowcases 0 1.1 s Artificially Stained Fabrics Clay 0 0.5 s Spaghetti sauce 0 1 . 2 s Barbecue sauce 0 0 . 0 Tea 3-4 5 Grass 0 3.1 s Menstrual blood 0 -0.1 Blueberries 0 1 . 4 s s = statistically significant difference tconfidence level of 90~) relative to the detergent granule alone treatment WHAT IS CLAIMED IS:

Claims (25)

1. A compound which has the formula:
(A) (B) or wherein R1 is an alkyl, aryl or alkaryl group containing from about 1 to about 14 carbon atoms, R2 is an alkylene, arylene or alkarylene group containing from about 1 to about 14 carbon atoms, R5 is H or an alkyl, aryl or alkaryl group containing from about 1 to about 10 carbon atoms, X is a compatible anion, n is 1 or 2, and Y
is from 0 to about 6.

2. A compound according to Claim 1 wherein the compound has the formulas:
or wherein R1, R2 and R5 are as defined in Claim 1.

3. A compound according to Claim 1 wherein R1 is an alkyl group containing from about 6 to about 12 carbon atoms, R2 is an alkylene group containing about 4 to about 8 carbon atoms, and R5 is H or methyl.

4. A compound according to Claim 1 wherein the compound is a magnesium peroxycarboxylate of the following general formulas or wherein R1, R2 and R5 are as as defined in Claim 1, X is a compatible anion, n is 1 or 2, and Y is from 0 to about 6.

5. A compound according to Claim 4 wherein R1 is an alkyl group containing from about 6 to about 12 carbon atoms, R2 contains from about 4 to about 8 carbon atoms, and R5 is H or methyl.

6. A bleach activator of the general formulas:

or wherein R1 is an alkyl, aryl or alkaryl group containing from about 1 to about 14 carbon atoms, R2 is an alkylene, arlene or alkarylene group containing from about 1 to about 14 carbon atoms, and R5 is H or an alkyl, aryl or alkaryl group containing from about 1 to about 10 carbon atoms, and L is a leaving group, the conjugate acid of which has a pKa in the range of from about 4 to about 13.

7. A compound according to Claim 6 wherein R1 is an alkyl group containing from about 6 to about 12 carbon atoms, R2 contains from about 4 to about 8 carbon atoms, and R5 is H or methyl.

8. The compound of Claim 6 wherein L is a leaving group, the conjugate acid of which has a pKa in the range of from about 6 to about 11.

9. The compound of Claims 6 wherein L is selected from the group consisting of:
and mixtures thereof wherein R1 is as defined in Claim 1, R3 is an alkyl chain contain-ing from about 1 to about 8 carbon atoms, R4 is H or R3, and Y
is H or a solubilizing group.

10. The compound of Claim 9 wherein Y is selected from the group consisting of: -SO?M+, -COO-M, -SO?A+, (-N+R?)X- and O+NR? and mixtures thereof wherein R3 is an alkyl chain containing from about 1 to about 4 carbon atoms, M is a cation which provides solubility to the bleach activator and X is an anion which provides solubility to the bleach activator.

11. The compound of Claim 10 wherein Y is selected from the group consisting of -SO3-M+, -COO-M+ and mixtures thereof wherein M is selected from the group consisting of sodium, potas-sium and mixtures thereof.

12. The compound of Claim 9 wherein L is selected from the group consisting of:
and wherein R3 is an alkyl chain containing from about 1 to about 8 carbon atoms, Y is -SO3-M+ or -COO-M+ wherein M is sodium or potassium.

13. The compound of Claim 12 wherein L has the general formula:
wherein M is sodium or potassium.

14. A bleaching composition comprising:
(a) from about 1% to about 60% of a peroxygen bleaching compound capable of yielding hydrogen peroxide in an aqueous solution; and (b) from ahout 0.5% to about 40% of a bleach activator selectcd from or or mixtures thereof, wherein R1 is an alkyl, aryl or alkaryl group, and R2 is an alkylene, arylene, or alkarylene group, each containing from about 1 to about 14 carbon atoms, R5 is H or an alkyl, aryl or alkaryl group containing from about 1 to about 10 carbon atoms and L is a leaving group, the conjugate acid of which has a pKa in the range of from about 4 to about 13 wherein the molar ratio of hydrogen peroxide yielded by (a) to bleach activator (b) is greater than about 1Ø

15. A composition according to Claim 14 also comprising from about 1% to about 30% of a detergent surfactant.

16. A composltion according to Claim 15 also comprising from about 10% to about 60% of a detergency builder.

17. The composition of Claim 16 wherein the molar ratio of hydrogen peroxide yielded by (a) to bleach activator (b) is at least about 1.5.

18. The composition of Claim 17 wherein the peroxygen bleaching compound is selected from the group consisting of sodium perborate monohydrate, sodium perborate tetrahydrate, sodium carbonate peroxyhydrate, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, sodium peroxide and mixtures thereof.

19. The composition of Claim 18 wherein the peroxygen bleaching compound is selected from the group consisting of sodium per-borate monohydrate, sodium perborate tetrahydrate and mixtures thereof.

20. The composition of Claim 14 wherein L is a leaving group, the conjugate acid of which has a PKa in the range of from about 6 to about 11.

21. The composition of Claim 14 wherein L is selected from the group consisting of:

, and mixtures thereof wherein R1 is as defined in Claim 1, R3 is an alkyl chain contain-ing from about 1 to about 8 carbon atoms, R4 is H or R3, and Y
is H or a solubilizlng group.

22. The composition of Claim 21 wherein Y is selected from the group consisting of: -SO?3M+, -COO-M+, -SO?M+, (-N+R?)X- and O+NR? and mixtures thereof wherein R3 is an alkyl chain containing from about 1 to about 4 carbon atoms, M is a cation which provides solubility to the bleach activator and X is an anion which provides solubility to the bleach activator.

23. The composition of Claim 21 wherein Y is selected from the group consisting of -SO3-M+, -COO-M+, and mixtures thereof wherein M is selected from the group consisting of sodium, potas-sium and fnixtures thereof.

24. The composition of Claim 23 wherein L is selected from the group consisting of:
wherein R3 is an alkyl chain containing from about 1 to about 8 carbon atoms, Y is -SO3-M+ or -COO-M+ wherein M is sodium or potassium.

25. The composition of Claim 24 wherein L has the general formula:
wherein M is sodium or potassium.