CA1109760A - Detergent bar manufacture - Google Patents

Detergent bar manufacture

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Publication number
CA1109760A
CA1109760A CA299,868A CA299868A CA1109760A CA 1109760 A CA1109760 A CA 1109760A CA 299868 A CA299868 A CA 299868A CA 1109760 A CA1109760 A CA 1109760A
Authority
CA
Canada
Prior art keywords
bar
sodium
detergent
isethionate
acyl isethionate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA299,868A
Other languages
French (fr)
Inventor
Richard Tokosh
Arno Cahn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Original Assignee
Unilever PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever PLC filed Critical Unilever PLC
Application granted granted Critical
Publication of CA1109760A publication Critical patent/CA1109760A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C11D3/02Inorganic compounds ; Elemental compounds
    • C11D3/04Water-soluble compounds
    • C11D3/046Salts
    • 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/126Acylisethionates
    • 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
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047Detergents in the form of bars or tablets
    • C11D17/006Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • 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
    • C11D3/34Organic compounds containing sulfur
    • C11D3/3409Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates

Abstract

Abstract of the Disclosure This invention relates to a detergent bar having superior use properties and comprising acyl isethionate as the major detergent surface active agent with an unesterified water-soluble alkali metal isethionate as a bar processing aid. Adding an alkoxy hydroxy propane sulfonate in conjunction with a small amount of sodium chloride to these toilet detergent bars significantly reduces the wear rate of the bar without adversely affecting its lathering characteristics.

Description

¦ "~ C 672 (R) 1~L~)9760 The present invention is concerned with an improvement ¦ in the lathering and wear rate properties of a toilet ¦ detergent bar having an acyl isethionate as the predominate ¦ surfacr--active detergent and an unesterified water-soluble ! 5 alkali rnetal isethionate as a bar processing aid.
One of the problems of acyl isethionate toilet detergent bars is their unusually high wear rate despite the attention given to other properties of this type of bar. For ' exarnple, in the U.S. Patent 4,007,125 it was found that the mush properties of an acyl isethionate detergent bar could ' be improved by adding to the bar an amount of sodium alkane ¦ sulfonate wherein the alkane group has 12 to 14 carbon atoms.
According to U.S. Patent ~,951,842, the mush properties of the same kind Or bar are improved by the ~ddition Or a mixture Or sodium sulfate and sodium chlor;de. U.S. Patent
2,356,9~3 describes the use of substantial amounts from 5 to 40% of sodium chloride as a wear-rate improver in soap-free detergent bars.
U.S. Patent 3,376,229 describes the use o~ sodium chloride to increase the hardness of acylisethionate bars.
~lowever, regardless of the improvement in the mush properties obtained with the detergent bars according to these patents, the wear rate of these bars still remains ; a problem, and any attempt to improve this latter property has heretofore been accomplished at the expense of lather ing.
'~'he use of alkoxy hydroxy propane suli'onates in soap b.lrs has been described in ll.S. Patent 2,987,4~4, ~herein ~b ~ . , , ~

I ~ I C 672 (R) ~1~9760 ~ sodium and potassium alkyl glyceryl ether sulfonates have ¦ been incorporated in soap bars as anionic surface active agents in amounts of ~5% and above. And in U.S. Patent 2,988,511 alkyl glyceryl ether sul~onates are described as major ànionic detergent actives, which can be used in ¦ cornbination with the isethionates. The lathering boosting properties of alkyl glyceryl ether sulfonate coMpounds, however~ when used in relatively small amounts with acyl isethionates as the major surfactant have not been recognized.
It has now been discovered that the incorporation of a relative]y small proportion of sodium alkoxy hydroxy propane sulfonate and a small amount of sodium chloride in a predominantly acyl isethionate detergent bar having an unesteriried water-soluble alkali metal of isethionic acid as a bar processing aid will significantly decrease the wear rate of the bar without adversely affecting its latherin~
properties and processing characteristics. The term "predominant", as used in connection with the proportion o~
acyl isethionate, means that the proportion Or acyl isethionate is not exceeded by any other surface active agent in the composition.
I'he present invention is particularly useful in that a more economical acyl isethionate detergent bar with less than the usual free isethionate salt can be made and marketed while the bar still maintains its excellent lathering properties.
The present application is applicable to toilet detergent bars o~ the type disclosed in U.S. Patent
3 -. . .

>~0 2,894,912 and in U.S. Patent 3,376,229. The major surface active agent in the detergent bar according to this application are aliphatic higher fatty acid esters of an alkali metal isethionic acid salt, which are hereinafter referred to as acyl isethionates. The acyl isethionate will comprise from about 30 to 70~ of the bar and can be defined by the following general formula:

RCOOCH2C~2S03M I "
wherein R is an aliphatic radical or mixed aliphatic radical of a higher fatty acid, or mixtures thereof, having from 6 to 18 carbon atoms and an iodine value of less than about 20; and wherein M is an alkali metal cation such as sodium, potassium or ammonium, or the cation of an organic amine base such as tri-ethanolamine, tri-isopropanolamine, diethanolamine and monoethanol-amine. The composition of the detergent bar can also contain from 2 to 1~% of at least one water-soluble suds-boosting deter-gent salt selected from the group consisting of alkali metal and organic amine higher aliphatic fatty alcohol sulfates, an alkyl aryl sulfonate and a higher aliphatic fatty acid tauride, from about 1~ to about 9% water, from about 2.5~ to about 25~ of a water-soluble higher fatty acid soap, and from 10 to 40~ of at least one higher fatty acid having from about twelve to about twenty-five carbon atoms as a binder and plasticizer, with the detergent bar having a pH within the range from 6 to 8, measured as a 10~ aqueous solution of the bar composition at 35C.

'`?~

11~9760 c 672 (R) ~,, , In addition, an unesterified water-soluble alkali metal salt of isethionic acid, such as sodium isethionate, is contained in the above detergent bar as a bar hardening ,:
and bar processing aid in an amount of from about1% to about 7%.
Detergent bars according to the above ~ormulation encounter various performance problems in that the wear rate is signiricantly higher than other known marketed soap and detergent bars, This wear rate, which is a measure of the loss in weight of the bar with usage, is largely due to the chemical properties of the bar. It has been discovered j that by reducing the acyl isethionate/sodium isethionate in the detergent bar with a corresponding increase in binder and/or plasticizer, a reduction in wear rate can ~ 15 generally be obtained. However, when this is done, 3 another property of the bar is sacrified; speci~ically, the latherlng properties Or the bar will decrease. In addition, adding suds boosters or suds additives to make up this lathering loss demonstrated that when lathering parity had been obtained, the suds booster caused processing problems in the manufacture of the bar.
Applicants have discovered that good lathering characteristics can be imparted to acyl isethionate detergent bars o~ the type described above without adverse processing or manuracturing problems by adding an alkoxy-hydroxy propane sulfonate having the following formula:
C~13-(CH2)n~CH2~O~CH2-CHOH_cH2_so3_M
; l~herein n is an integer from 6 to 1~; and M can be calcium, `: :
' ~

- , ~ , -.: . ' ~ ' ~ ., ' ' ' :: .

l C 672 (R) " 11~97~0 : .
magnesium, ammon;um, sodium or potassium.
Excellent lathering characteristics can be obtained, for example, when sodium alkoxy hydroxy propane sul~onate is ¦ added as a suds booster to the acyl isethionate detergent I 5 bar formulation. In addition to the excellent lathering ¦ properties that can be obtained, it was ound that incorporating from about 2 to 10~ of the above defined alkoxy hydroxy propane sulfonate will not cause processing problems.
While the lathering and processing characteristics o~
~ 10 the acyl isethionate detergent bar are improved by the ¦ addition of the alkoxy hydroxy propane sulfonate, the wear ¦ rate of the bar still re~ains significantly high. Applicants I have discovered, however, that the wear rate of the above improved acyl isethionate bar can be substan~ially lowered by adding to the detergent bar, in addition to the alkoxy hydroxy propane sulfonate, sodium chloride in an amount of - ~ less than 1.2%. Normally, a drop in wear rate is accompanied by a reduction in lathering While the sodium alkoxy hydroxy propane sulfonate/sodium chloride combination will significantly reduce the wear rate, the lathering I characteristics Or the improved acyl isethionate bars were ; ~ unexpectedly equal or slightly superior to a detergent bar, such as that described in V.S. Patent 3,376,229. Accordingly, . ~ the alkoxy hydroxy propane sulfonate/sodium chloride combination~ at the levels indicated hereinafter, will enable a more economical acyl isethionate detergent bar to be produced having improved wear rate while still maintaining the excellent lathering characteristics obtainable with the .', , ' . . - ' :

.. . . .
- , - ~ .

C 672 (R) 7~

- alkoxy hydroxy propane sulfonate.
In accordance with the improvement herein, then, a method is provided for reducing the wear rate of an acyl isethionate detergent bar having an unesterified water-soluble alkali metal isethionate as a bar processing aid, without adversely affecting the lathering properties or processing characteristics of the bar, by incorporating into the bar:
(a) from 1% to 10%, and preferably 2% to 6%, by weight of an alkoxy hydroxy propane sulfonate having the formula CH3 (cH2)n-cH2-o-c-r~2-~cHoH-cH2- S03-M
wherein n is an integer from 6 to 18; and M is sodium, ¦ potassium, calcium, or ammonium; and ¦ (b) less than 1.2%, preferably 0.1% to 1.0% and ¦ ~5 desirably 0.~% to 1.0%, of sodium chloride, the percentages ¦ being ba~sed on the total weight of the detergent bar . produced.
q~he acyl isethionate detergent bar made according to the method described above c,n be prepared by conventional ` 1 20 practices known to those skilled in the art of toilet and detergent bars, and will generally comprise from about30%
to 70% of an acyl isethionate of the general formula CH2cH2so3M
wherein R is an aliphatic radical or mixed aliphatic radical of a higher fatty acid, or mixtures thereof, having from six to eighteen carbon atoms and an iodine value of less than i about 20; and wherein M is an alkali metal cation, such as sodlllr~l, potassium or ammonium, or the cation of an organic i`

.
, .
.
:
:
.

~ C 672 (R) ,~
7~(~
, . amine base, such as triethanolamine, tri-isopropanolamine, diethanolamine and monoethanolamine; and from about1% to about 7% of an unesterified water-soluble alkali metal : isethionate as a bar processing aid. The acyl isethionate :~ 5 detergent bar formed according to the method above may alsocontain from 2 to 10% of at least one water-soluble suds-boosting detergent salt selected from the group consisting of alkali metal and organic amine higher aliphatic fatty alcohol sulfates, an alkyl aryl sulfonate, and a higher aliphatic fatty acid tauride, from about 1% to about 9%
3 wa.ter, from about 2.5% to about 25% of a water-soluble higher `j fatty acid soap, and from 1~ to 40% of at least one higher j fatty a.cid having from about twelve to about twenty-five carbon atoms as a binder and plasticizer, with the finished detergent bar having a pH within the range from 6 to 8, measured as a 10% aqueous solution of the bar composi~ion, . at ~5C.
Accordingly the invention provides a detergent bar . comprising . 20 (a) 1% to 10%,preferably 2% to 6%, by weight of an alkoxy hydroxy propane sulfonate of the formula CH3-(CH2)n~CH2~0~CH2-CHOH_cH2_so3_M
wherein n is an integer Or from 6 to 18; and M is sodium, ¦ potassium, calcium, magnesium or aMmonium;
. 25 (b) ].ess than 1.2%, preferably 0.1% to 1.0%, and . desirably 0.6% to 1.0%, by weight of sodium chloride;
~ (c) about 30% to about 70% of an acyl isethionate of ¦ the formula ~, ' " ',' ` ' ~

C 572 (R) ''-` 11~97~i0 RCOOCH2CH2$o3~
wherein R is an aliphatic radical or mixed aliphatic radicals of a higher fatty acid, or mixtures thereof, having ~rom six to eighteen carbon atoms and an iodine value of less than about 20; and wherein r1 is an alkali metal cation such as sodium, potassium or ammonium, or the cation Or an organic amine base such as triethanolamine, tri-isopropanol-amine, diethanolamine and monoethanolamine; and (d) about 1% to about 7% o~ an unesterified water-soluble alkali metal isethionate, for example, guch as sodium isethionate, as a bar processing aid.
, Moreparticularly, a detergent bar according to the ¦ iMprovernent herein comprises the following components in parts by weight:
~5 Parts by Weight Or Bar a. Acyl isethionate 35-55 b. Higher fatty acid 20-27 c. Higher fatty acid soap 5-15 d. Sodium alkylbenzenesulfonate2-4 e. Sodium isethionate 1-4 ~. Sodium chloride 0.1-1.0 g. Alkoxy hydroxy propane sulPonate 1-10 h. Water 3-6 wherein the higher fatty acid is selected from the group consisting Or palmitic and stearic acid, the higher I rattY acid soap is the sodium salt o~ an aliphatic mono-I carboxylic acid having rrom about 8 to about 18 carbon ~toms, of l,lhich about lB-22~ has R-14 carbon atoms, the , I
, ' ' ' " ~ ' ~ ' ` ~, ` ' ' C 672 (R~
97~i0 '' alkyl group of said alkylbenzenesulfonate is derived from a straight-chain hydrocarbon mixture having an average of about 13 carbon atoms; and the sum of (a) through ~h) lies within the range of about 96 to about 100 parts by weight.
As a preferred embodiment, the toilet bars of the present invention comprise the following components in the proportions indicated:
Parts by Wei~ht of Bar a. Sodium acyl isethionate 38-46 b. Higher fatty acid 21-25 c. Higher fatty acid soap 8-13 d. Sodium alkylbenzenesul~onate 1-3 ¦ e. Sodium isethionate 1-4 ¦ f`. Sodium chloride 0.5-1.0 g Sodium alkoxy hydroxy propane sulfonate 2-7 h. Water 3-6 : wherein the acyl portion o~ said isethionate is derived ~rom coconut oil, said higher fatty acid is selected from the group consisting of palmitic and stearic acids, said 2 soap is the sodium salt of an aliphatic monocarboxylic acid having ~rom about 8 to 18 carbon atoms, of which about 18-22% has 8-14 carbon atoms, the alkyl portion of said alkylbenzenesul~onateis derived from a straight-chain : hydrocarbon mixture having an average of about 13 carbon atoms; and the sum of (a) through (h) lies within the range o~ about 96 parts to about 100 parts by weight, the balance, i~ any, comprising minor additives, such as germicides, ,! ~iO2, colorants and miscellaneous ingredients associated with C 672 (R) 97~0 the above-named components.
Particularly advantageous bars in accordance with the improvement herein have the following composition:
Parts by Weight of Bar Sodium acyl isethionate (a) 40-42 Stearic acid 20-23 Coconut oil fatty acids 2-3 Soap of mixed tallow and coconut oil (b) 9.5-10.5 Sodium stearate 2.5-3.5 Sodium isethionate 1-3 Sodium alkylbenzenesul~onate (c) 1.5-2. 5 Sodium chloride 0.6-1.0 Sodium alkoxy hydroxy propane sulfonate (d) 4-6 TiO2 0.1-0.3 Germicides 0-1. 5 Mineral Oil 0-1.5 ' Perfume 0.7-1.7 Colorants 0.001-0.003 iscellaneous (e) 1.5-3 Water 4-6 (a) the alkyl group is derived from coconut oil, (b) about 75-fl5 parts tallow and about 15-25 parts coconut oil, (c) the alkyl group is a straight chain having about 11-15 carbon atoms, (d) the alkyl group is a straight chain having about 8-20 carbon atoms, (e) inert matter unavoidably added in associati~on with the components;
.

:' ~.r, ,.- r. .

' ' ~ ' . .

:

C 672 (R) 97~0 wherein the acyl portion of said sodium acyl isethionate is derived from coconut oil; and the alkyl :~ portion of said sodium alkyl benzenesulfonate is derived . from a straight-chain hydrocarbon mixture having about 11-15 carbon atoms.
The acyl isethionate component of the detergent bar may be prepared by methods well known to those skilled in the art Suitable preparatory procedures may be found in - U.S Paten~ Nos. 3,320,292; 3,376,229; 3,151,136; 3,3~3,396;
3,420,857, and 3,420,858.
. The term "soap" is used herein in its popular sense, ! i.e. the alkali metal salts of aliphatic alkane- or ~ alkenemonocarboxylic acids. In general, the sodium soaps I can be used in the bars of the invention, but from about 1 ¦ 15 to about 25% of the soap may be potassium soaps. The soaps ; useful herein are the ~lell-kno~n alka].i-metal salts of natural or synthetic fatty (alkanoic or alkenoic) acids having about 12 to 20 carbon atoms, preferably about 12 to about 18 carbon atoms, and may be described as alkali-metal carboxylates of acyclic hydrocarbons having about 12 to about 20 carbon atoms.
Soaps having the fatty acid di.tribution Or coconut oil may provide the lower end of the bro~.d molecular weight ; range, while soaps having the fatty acid distribution of peanut or rapeseed oil, or their hydrogenated derivatives, may prov;.de the upper end of the broad molecular weight ran~e.
It is preferred to use the soap~ having the fatty acid ' , :- -C 672 (R) 11;~)97~il) distribution of coconut oil or tallow, or mixtures thereof~
since these are among the more readily available fats. The proportion of fatty acids having at least 12 carbon atoms in coconut oil soap is about 84%. This proportion will be greater when mixtures of coconut oil and ~ats such as tallow, palm oil, or non-tropical nut oils or fats are used, wherein the principal chain lengths are C16 and hiKher. The preferred soap for use in the acyl isethionate detergent bar then has at least 84~ ~atty acids h~ving about 12-18 carbon atoms.
It will be understood that the coconut oil employed for the soap, and for the isethiona~e as well, may be substituted I in whole or in part by other "high lauric" oils, that is, oils ¦ or fats wherein at least 50~ of the total fatty aeids are composed of lauric or myristie acids or mixtures thereof.
I 15 These oils are generally exemplified by the tropieal nut oils of thecoconut oil class, such as palm kernel oil, babassu oil, ouricuri oil, tucum oil, cohune nut oil, murumuru oil, jaboty kernel oil, khakan kernel oil, dika nut oil, and for present purposes ueuhuba butter, a vegetable triglyceride high in myrist~c acid esters.
A preferred soap is a mixture of about 15% to about 20% coconut oil and about 80% to about 85% tallow. These mixtures contain about 95-96% fatty acids having about 12 to about 18 carbon atoms. q'he soap may be prepared from coconut oil, in which ease the fatty acid content is about 84~ of C12-C18 ehain length The soaps may contain unsaturation in accordance with the commercially acceptable standards. Excessi~e unsaturation is I
. ... .. .
.
..
' -.
. . ~. ~ . , .

C 672 (R) 7~

norma11y avoided.
The sodium alkoxyhydroxy propane sulfonate may be . prepared in accordance with the procedure described in U.S. Patent 2,989,547.
The hi.gher fatty acid component recited in the foregoing compositions is preferrably a commercial mixture of about 45% stearic acid and about 55% palmitic ac;d.
The rate at ~hich a toilet detergent bar wearsaway . during use is quantitatively determined by méasuring the 1 rate at which the tablet wears during a standardized washing procedure, referred to hereinafter as the "Wear Rate 1'est", whereby the weight of the bar consumed per use is determined.
The Wear Rate Test is conducted in accordance with the description given below. It will be understood that the results obtained by this test may vary slightly ~rom ; operator to operator and may show variations from day to day, but that the results obtained on tablets tested as a group by the same operator may be validly compared. For this reason, control bars are tested along with the bars Or 1 20 each Example herein.
: Wear Rate Test ': Equiprment : a. Smooth ~lat-bottomed pl.astic soap di.shes, . ~. ~in rack or other point support for drying bars, c. ~al].on container marked at 1/2 gallon.
P r o c ~ re I T~e test begins on the morning o~ Day 1, and terminates ¦ on the morning of Day 3. The initial ~reia,ht of the bar to the i - 14 -' :

' 11~97~0 c 672 (R) nearest 0.0l gram is recorded. One half gallon of tap water at 40C is poured into a procelain sink. The hands and bar are submerged in the 40C water~ the bar and hands removed, and the bar rotated 20 times between the hands (l rotation=1D~0C).
The same procedure is repeated bysubmerging the bar and hands in the water, rernoving the bar and hands, and the above-described washing (20 rotations) repeated. T~ bar and hands are again submerged in the water, the bar removed from the hands and placed in the dish. The above-described washing is repeated 4 times during the day on Day l, and a~ain on Day 2.
Tap water at 27C is added to the dish prior to placing the bar in the dlsh following the first and last ~rashing on Day l and Day 2 (~-l/2 ml Or tap water for regular si~e, 2-l/2 rnl of tap water for bath size).
On the morning of Day 3, the bar is washed as before, rlnsed ln the wash water, and placed on pin rack to dry. The bar is dried at least 4 hoursand weighed to the nearest 0.0l gram.
Calculation Calculate the weight in grams used per wash as rOllOws:
Initial we ght in grams - final weight in grams = grams number of washes per use Panel l.ather Test Twenty panelists, each with a control bar and an experimenta] bar, wash each bar under the following set of water hardness and temperature conditlons in separate sinks:
a- 90-100 ppm hardness as CaC03 at 24C, b. l80 ppm hardness as CaC03 at 24C, and c. 180 ppm hardness as CaCO~ at 40 c~

-- 1~ --! C 672 (R) _..~
" 1~9760 Each panelist washes his hands in his customary manner under the aforementioned conditions and makes a preference for either the control or experimental detergent toilet bar based on lather volume within each test condition. The panelist may also rate the 'oars equal i' they perceive lathering parity.
Therefore, the higher the preference for a nroduct the higher the number.
The invention may be more thoroughly understood by reference to the following Examples, which are to be considered illustrative~ but not limitative, of the improvement herein.
Exarnple (a~
l'his Example describes the preparation of sodium acyl isethionate detergent active.
¦ 15 2150 kg of' sodium acyl isethionate having 75% active detergent matter are prepared in the f'ollowing manner:
1100 kg of coconut ratty acids and 310 kg of ratty acids recovered in the stripping step of a previously prepared batch Or ~atty acid isethionate are combined in a scale tank. A slurry containing approximately 75~ by weight of sodiurn isethionate on a 100% pure basis are charged into a stock tank. Finally, 3 kg of zinc oxide are prepared as an aqueous slurry in another tank.
A]l Or the roregoing ingredients are charged into reactor and heated to a temperature of about 232C by circulating the contents of the reactor through a heat exchanger via a pump.
When the temperature o~ the reaction mixture reaches ~ C 672 (R) ~ about 190-200C, water evolved by the reaction, together ¦ with steam distilled fatty acids, begin to distill from the reactor. These vapors are then condensed in a condenser. The fatty acids and water condensate are collected in a separator wherein the fatty acids are decanted via a pipe and accumulated in a collecting tank.
The reaction is essentially complete in approximately 150 minute~ at 232-237C, when both fatty acids and water cease to accumulate in the separator.
At this point, the reaction mixture is drained into a stripper which is also purged with nitrogen to maintain an oxygen-f'ree atmosphere. By circulating a heat transfer liquid through the jacket of the stripper, the temperature of' the reaction mixture is maintained between about 220C
and 235C.
A vacuum is applied by means of ejectors to obtain a vacuum Or about 50 cm of mercury. After maintaining this vacuum for a period of about 15 minutes, 360 kg of molten stearic acid is charged into the stripper to rnaintain the fluidity of' the reaction product therein after the initial portion of unreacted fatty acids is removed. The removal Or the unreacted fatty acids of the charged stock iscompleted by further increasing thevacuum to about 69 cm mercw~ and rrlaintaining i,t at t~)is level, while the rrlass in the stripper is maintained at 232C ~'or a period of' about 45 minutes. At this point, ti~e pressure is ~rought back to ~,trnospheric by shutting off the vacuum ejectors and introducin~ nitrogen into the stripper.
The fatty acids collected during the stripping are .:

, ~ C 672 (R) ~1~97~i~

returned to the fatty acid charged tank for reuse in subsequent reactions.
After analyzing the completed batch of acyl `
isethionate, the reaction product, weighing 2160 kg, is dischar~ed and ~lash-cooled The analysis shows that the acyl iseth;onate content is about 75.0%, corresponding to a yield of about 92~ based on the iset~lionate charged to the reactor.
Example 1 This Example describes the preparation of a detergent bar having the acyl ~isethionate o~ Example la.
A Day mixer is charged with the appropriate amounts of stearic/palmitic acid (45:55 ratio by weight - ~mersol 132), soap, sodium stearate, sodiwn alkyl (C13-average) benzene sulfonate and sodium chloride, followed by the ilash cooled acyl isethionate of Exarnple la to gi~e the composition on a percent by weight basis set forth below in Table A. The ingredients are mixed at 107C for approximatelY 60 minutes. The composite is discharged onto a chilled rotating drum and processed into chips. The chips are then charged into a chip mixer to which perfume and TiO2 are milled and plodded into bar form.

~ 760 C 672 (R) TABLE A

Example No. la lb lc Box Code No. NS4207 NS4208 NS4209 _ _ (Control) Composition % by weight % by ~eight % by weight Acyl isetionate o~ Example (a) (active basls) 50.00 47.00 45.00 ¦ Stearic/pa~nitic acid21.86 24.11 25.61 ¦ Coconut oil ratty acids3.o8 2.90 2.77 Soap of mixed tallow and coconut oil 9-7 9.82 10.32 Sodium stearate 3.00 3.00 3.00 Sodiwn isethionate 1.91 1.80 1.72 Sodium alkyl.benzene sulfonate 2.03 2.03 2.03 Sodium chloride 0.85 o.85 0.85 Water 5.25 5.25 5.25 qliO2 0.20 0.20 0.20 Perf~une 1. O0 1. O0 1. OO
Miscellaneous 1.75 2.04 2.25 100.00 100.00 100.00 The detergent toilet barshaving the above compositicns were tested for wear rate and lather by the aforementioned procedures. The results are listed in Table B.

~, ~

.
., C 672 (R) ~lQ~760 Table B. E~fects of reducing acyl isethionate/sodium _ isethionate in deter~ent toilet bars Wear Rate ~xample No. Wear ~a.te (gms/wa~h) ... . . _ .
1~ - 50% acyl isethionate (control) 3.40 + 0.14 lb - 47% acyl isethionate 3.15 + 0.09 lc - 45% acyl isethionate 2.76 ~ 0.17 Panel Latherin~
~!ash Conditions 24C/ 24C/ 40C/ Overall 90pp~CaCO7~180ppm 180ppm ~esults la - 50% acy~ isethionate (control) 11 11 13 35 Ib - 47% acyl isethionate 8 8 6 22 la and lb EQUAL in lather lc? - 50% acyl isethionate (control) 11 13 11 35 lC - 45~ acy] isethionate 6 5 7 18 la and lc EQUAL in lather 3 2 2 7 rl'he above data sho~ that decreasing the acyl isethionate/sodium isethionate in conjunction with a corresponding increase in stearic/palmitic acid and soap I wi.ll signi~icantly reduce the wear rate of the detergent bar. ~-~owever, the panel lathering data demonstrate that the panel:ist perceived ~ reduction in ].athering in the low acyl .isethionate/reduced wear rate bars as compared with the 2 5 control bars.

~ 7~0 C 672 (R) l~`xample 2 This example illustrates the ef~ect that sodium alkoxy hydroxy propane sulfonate prepared from Neodol 25 having an alkyl group = C12-C15 and NaCl, has on reduced acyl isethionate deter~ent toilet bars.
Detergent toilet bars having the following composition were prepared. All percentages are givèn on the basis of weight of the total bar.
TABLE C
Example No. 2a 2b 2c Bar Code No. NS4251 NS4252 NS4253 (Control) Composi.~,i,on ~ % %
Acyl isethionate of Example (a) (active ba,sis) 50.00 45.00 41.00 Sodiwrla:Lko~ hydro~y prcpane sul~onate (aIkyl group consists .' of'C12-C~5) - 2.00 ~.on Steari.c/palmitic acid 20.16 24.11 24.86 Coconut oil f'atty acid 3.08 2. 77 2.53 Soap o~ mixed tal].cw and COCOIlut oil 8.50 9.82 10.07 So~ium stearate 3,oo 3.00 3.00 Sodiwn iseth:ionate 4.68 1.72 1.56 Soc~iw(l alky].benzene sulf'onate2.03 2.0 3 2.0 3 Sodiwllchloride 0,35 ' 85 o,85 Water 5.25 5.25 5.25 qio2 0.20 0.20 0.20 Perfw~le 1.00 1.00 1.00 S r~.scellaneous 1- 75 1.75 1.75 ~oo . oo loo . no loo . oo .

C 672 (R) )976~1 The detergent toilet bars having the above compostions are tested for wear rate and lather properties by the afore-mentioned procedures. The results are listed in Table D below.

Table D. Effect of appropriate amounts of sodium al~oxy hydroxy propane sul~onate (C~2-C1s) and NaC1 in reduced acyl isethionate/sodlum isethionate _ deter~ent toilet bars Wear Rate Example No. Wear Rate (grams/wash) 2a - 50% acyl isethionate (control) 3.72 + 0.21 2b - 45% acyl isethionate + 2%
sodium alkoxy hydroxy propane sulfonate3.15 + 0.10 j 2c - 41% acyl isethionate + 5%`
sodium alkoxy hydroxy propane sulfonate3.16 + 0.06 Panel Latherin~
Example No. Wash Conditions 1 24C/ 40C/ Overall , 20 180ppm CaC~ 180ppm Results j 2a - Control 9 10 19 2b - 45% acyl isethionate + 2%
sodium alkoxy hydroxy propane sulfonate11 8 19 2a and 2b EQUAL in lather - 2 2 2a - Control 12 8 20 2c - 41% acyl isethionate + 5%
sodium alkoxy hydroxy propane sulfonate 8 10 18 2a and 2c EQU~L in lather - 2 2 Table D demonstrates that reducing the acyl isethionate/sodium isethionate in conjuction with the incorporation of sodium alkoxy hydroxy propane sulfonate I ~ C 672 (R) ~L.L~7~0 and an appropriate amount of NaCl will significantly reduce the wear rate of the detergent bar. It was illustrated in Table B that a reduction in wear rate (reduced acyl isethionate/so~ium lsethionate and NaCl added) will adversely affect the lathering properties of the bar. However, Table D demonstrates that lathering parity is obtained between the control and lowered acyl isethionate/sodium isethionate 3 detergent toilet bars when an appropriate amount of sodium alkoxy hydroxy propane sulfonàte is incorporated into the formulation.
Example 3 g A straight chain sodium alkoxy hydroxy propane sulronate having chain lengths ~ ClO and Cl8 was prepared, and the following acyl isethionate detergent bars were formu ated based on the same:

. .

C 672 (R) TABLE E
Example No. 3a 3b 3c Bar Code No. NS4266 NS4267 NS4268 (Control) Com~osition ~ % %
Acyl isethionate of Example (a) (actlve basis) 50.00 41.00 41.00 Sodiurn aIkoxy hydroxy propane sulfonate (C10) _ 5 0O
Sodium aIkoxy hydroxy propane sul~onate (C18) _ _ 5 00 Stearic/palmitic acid 2~.I6 24.86 24.86 Coconut oil fatty acid` 3.08 2-53 2-53 Soap of mixed tall~r and coconut oil 8.50 10.07 10.07 Sodi~ stearate 3.00 3.00 3.00 Sodium isethi.onate 4.68 1.56 1.56 Sodium alkylbenzene sulfonate 2.03 2.03 2.03 Sodium chloride 0-35 0.85 o.85 Water 5.25 5.25 5.25 TiO2 0.20 0.20 0.20 Perfume 1.00 1.00 1.00 Miscellaneous 1.75 2.65 2.65 100.00 100.00 100.00 The detergent toilet bars having the above compositions were tested for wear rate and lather characteristics by the aforementioned procedures. The results are listed below in Tab le F .

C 672 (~) 7~

rrable F. Ef~ect of appropriate amounts o~ sodium alkoxy hydroxy propane sulfonate (C10 and C1~) and NaCl in reduced acyl isethionate/sodlum iseth1onate deter~ent toilet bars . .
Wear ~ate Examp]e No. Wear Rate (grams/wash) 3a - 50% acyl isethionate (control) 3~95 + 0.17 3b - 41% acyl isethionate + 5%
sodium alkoxy hydroxy propane sul~onate (C10) 3.58 + 0.11 3c - 41% acyl isethionate + 5%
sodium alkoxy hydroxy propane sulfonate (C18) 3.44 ~ 0.12 Panel Lathering Example No. Wash Conditions 24C/ 24&/ 40C Overall 9Oppm CaC0~ 180pp~ 180ppm Results 3a - 50% acyl isethionate (control) 4 9 7 20 3b - 41% acyl isethionate + 5%
sodi~n alkoxy hydroxy propa~e sulfonate (C10) 16 11 13 40 3a and 3b EQUAL in lather - - - -3a - 50% acyl isethionate (control) 9 9 9 27 3b - 41%acyl isethionate + 5%
sodium a~oxy hydroxy ether sulfonate (C18) . 8 11 10 29 3a and 3c EQUAL in lather 3 0 1 4 The data presented in Table F demonstrate that the sodium alkoxy hydroxy propane sul~onate~sodium chloride combination in lowered acyl isethionate/sodium isethionate toilet detergent bars results in a significantly improved wear rate without an adverse efrect in lathering properties of the bar.

C 672 (R) 11~976~

~xample 4 .
This Example demonstrates the effect of the addition of an appropriate amount of an alkoxy hydroxy propane sulfonate on a lowered acyl isethionate/sodium isethionate detergent bar, with and without the inclusion Or NaCl.
TABLE G
Example No. 4a 4b 4c Bar Code No. ~S4312 NS4314 NS4315 (~ontrol) (no salt) Co_~osition % ~ %
Acyl isethionate of Example(a) (active basis) 50.00 41.00 41.00 Sodium alkoxy hydroxy propane sulf.onate C14 - 5.00 5.00 Stearic/palmitic acid20~ 16 25~ 50 24.86 ~oconut oil fatty acid3~08 2~53 2~53 Soap of mixed tallow and coconut oil 8.5~ 10.28 10.07 Sodium stearate 3~00 3~00 3~00 Sodiwm ;.sethionate 4~68 1~56 1~56 Sodium alkylbenzene sulfonate 2~03 2~03 2~03 Sodium chloride 0. 35 ~ 0~ 85 Water 5~25 5~25 5~25 TiO2 0~20 0~20 0~20 Perfume 1.00 1.00 1.00 Miscellaneous 1- 75 2 ~ 65 2 ~ 65 100.00 100.00 100.00 The detergent toilet bars having the above composition, were tested for wear rate and lather characteristics by the ~ 26 ~

C 672 (R) ~ll'Q~7~V

aforementioned procedures. The results are listed below in Table H.

Table H. Effect of appropriate amounts of sodium alkoxy hydroxy propane sulfonate with and without NaCl in lowered acyl isethionate/sodium isethionate toilet .
deter~ent bars Wear ~ate Example No. Wear Rate (~rams/wash) 4a - 50% acyl isethionate (control) 2.93 + 0.12 4b - 41% acyl isethionate + 5%
sodium alkoxy hydroxy propane sulfonate (C14)(no salt) 3.05 + 0.18 4c - 41% acyl isethionate + 5%
sodium alkoxy hydroxy propane sulfonate (C14)(.85% salt) 2.47 + 0.18 Panel Lathering Example No. Wash conditions _ 24C/ 24C/ 40~ Overall 90ppm CaCO~ 180p~m 180ppm Results 4a - 50% acyli.sethionate (control) 4 5 5 14 4b - 41% acyl isethionate + 5%
sodium a~oxy hydroxy propane sulfonate (C1~)(no salt) 4 4 4 12 4a and 4b EQUAL in lather 2 1 1 4 4a - 50% acyl isethionate (control) 5 4 3 12 4c - 41% acyli.sethionate + 5%
sodi.um a~oxy hydroxy ether sulronate (C14)(.85% salt) 5 5 7 17 4a and 4c EQUAL in lather The data presented in Table H demonstrate that the incorporation of an alkoxy hydroxy propane sulfonate into a lowered acyl i.sethionate/sodium isethionate detergent bar gives lathering parity with a detergent bar having no .. - 27 -C 672 (R) 97~0 reduction in the acyl isethionate/sodium isethionate content (4a vs. 4b). However, the wear rate of detergent bar 4b was deter~ined to be practically equally as high as the wear rate of detergent bar 4a.
On the other hand, when detergent bars 4a and 4c were compared, the latter having incorporated therein appropriate amounts of alkoxy hydroxy propane sul~onate and sodium chloride, a significant reduction in wear rate was observed while at the same time maintaining lathering parity with detergent bar 4a.

-

Claims (10)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for reducing the wear rate of an acyl isethionate detergent bar having an unesterified water-soluble alkali metal isethionate as a bar processing aid, without adversely affecting the lathering properties of the bar, which comprises incorporating into said bar:
(a) from about 1% to 10% by weight of an alkoxy hydroxy propane sulfonate having the formula:
CH3-(CH2)n-CH2-O-CH2-CHOH-CH2-SO3-M
wherein n is an integer from 6 to 18; and M is sodium, potassium, calcium, magnesium or ammonium; and (b) less than 1.2% by weight of sodium chloride;
the percentages being based on the total weight of the acyl isethionate detergent bar produced.
2. The method according to claim 1 wherein the alkoxy hydroxy propane sulfonate is incorporated into the acyl isethionate detergent bar in an amount of from 2% to 6%
by weight.
3. The method according to claim 1 wherein the sodium chloride is incorporated into the acyl isethionate detergent bar in an amount of from 0.1% to 1.0% by weight.
4. The method according to claim 1 wherein the sodium chloride is incorporated into the acyl isethionate detergent bar in an amount of from 0.6% to 1.0% by weight.
5. The method according to claim 1 wherein the alkoxy hydroxy propane sulfonate and sodium chloride is incorporated into an acyl isethionate detergent bar comprising (a) from about 30% to 70% of an acyl isethionate of the general formula:

wherein R is an aliphatic radical or mixed aliphatic radicals of a higher fatty acid, or mixtures thereof, having from six to eighteen carbon atoms and an iodine value of less than about 20; and M is an alkali metal cation or the cation of an organic amine of triethanolamine, tri-isopropanolamine, diethanolamine, or monoethanolamine;
(b) from about 1% to about 7% of an unesterified water-soluble alkali metal salt of isethionic acid;
(c) from about 2% to 10% of at least one water-soluble suds-boosting detergent salt selected from the group consisting of alkali metal and organic amine higher aliphatic fatty alcohol sulfates, an alkyl aryl sulfonate, and a higher aliphatic fatty acid tauride;
(d) from about 1% to about 9% water;
(e) from about 2.5% to 25% of a water-soluble higher fatty acid soap; and (f) from about 10% to 40% of at least one higher fatty acid having from about 12 to 25 carbon atoms as a binder and plasticizer;
thereby forming a detergent bar having a pH within the range of from 6 to 8 measured as a 10% aqueous solution of the composition at 35°C.
6. The method according to claim 5 wherein the acyl isethionate is sodium acyl isethionate, the acyl portion being derived from coconut oil, and the salt of isethionic acid is sodium isethionate.
7. The method according to claim 1 wherein the alkoxy hydroxy propane sulfonate is sodium-3-alkoxy-2-hydroxy-1-propane sulfonate, the alkyl group having 12 to 15 carbon atoms.
8. An acyl isethionate toilet detergent bar comprising:
(a) from about 30% to 70% of water-soluble alkali metal detergent salt of esters of isethionate acid with mixed aliphatic fatty acids having from six to eighteen carbon atoms and an iodine value of less than 20, of which mixed acids at least 75% have from twelve to eighteen carbon atoms and up to 25% have from six to ten carbon atoms;
(b) from 2 to 10% of at least one water-soluble suds-boosting detergent salt selected from the group consisting of alkali metal and organic amine higher aliphatic fatty alcohol sulfates, alkyl aryl sulfonates, and the higher aliphatic fatty acid taurides;
(c) from about 1% to about 9% water;
(d) from about 2.5% to about 25% of a water-soluble higher fatty acid soap;

(e) from about 10 to 40% of at least one higher fatty acid having from twelve to about twenty-five carbon atoms as a binder and plasticizer;
(f) about 0.1% to about 1.0% sodium chloride;
(g) about 1% to about 10% of an alkoxy hydroxy propane sulfonate where the alkyl group consists of C8 to C20, or mixtures thereof; and (h) from about 1% to about 7% of an unesterified water-soluble alkali metal salt of isethionic acid;
said bar having a pH within the range of about 6 to about 8 measured as a 10% aqueous solution of the bar composition at 35°C.
9. The toilet detergent bar of claim 8 wherein said alkoxy hydroxy propane sulfonate is sodium-3-alkoxy-2-hydroxy -1-propane sulfonate having an alkyl chain length of C8.
10. The toilet detergent bar of claim 8 wherein said alkoxy hydroxy propane sulfonate is sodium-3-alkoxy-2-hyroxy-1-propane sulfonate having an alkyl chain length of C20.
CA299,868A 1977-03-30 1978-03-29 Detergent bar manufacture Expired CA1109760A (en)

Applications Claiming Priority (2)

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US78269877A 1977-03-30 1977-03-30
US782,698 1977-03-30

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JP (1) JPS6041117B2 (en)
CA (1) CA1109760A (en)
DE (1) DE2813324A1 (en)
NL (1) NL187122C (en)
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1304270C (en) * 1984-09-25 1992-06-30 Michael Lynn Caswell Cleaning compositions with skin protection agents
US4954282A (en) * 1989-04-19 1990-09-04 Lever Brothers Company Acyl isethionate skin cleansing compositions
WO1995016022A1 (en) * 1991-12-04 1995-06-15 Colgate-Palmolive Company Process for toilet bars and resulting bar
DE4409321A1 (en) * 1994-03-18 1995-09-21 Henkel Kgaa Low m.pt fatty acid isethionate-based detergent mixt.

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NO148075C (en) 1983-08-24
NL187122B (en) 1991-01-02
JPS53137209A (en) 1978-11-30
DE2813324C2 (en) 1987-02-19
SE439017B (en) 1985-05-28
NL187122C (en) 1991-06-03
NL7802972A (en) 1978-10-03

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