U.S. patent number 3,764,531 [Application Number 05/088,486] was granted by the patent office on 1973-10-09 for antimicrobial and laundry softening compositions.
This patent grant is currently assigned to Henkel & Cie G.m.b.H.. Invention is credited to Horst Bellinger, Hans-Werner Eckert, Arnold Heins.
United States Patent |
3,764,531 |
Eckert , et al. |
October 9, 1973 |
**Please see images for:
( Certificate of Correction ) ** |
ANTIMICROBIAL AND LAUNDRY SOFTENING COMPOSITIONS
Abstract
An antimicrobial and softening composition for laundry use
comprises a water-soluble heavy metal-free non-oxidizing
antimicrobial agent, and a glycamide of the formula: ##SPC1##
Wherein R.sub.1 and R.sub.2 are alkyl groups having a total of 23
to 39 carbon atoms, and n is 3 or 4, preferably 4.
Inventors: |
Eckert; Hans-Werner
(Dusseldorf, DT), Heins; Arnold (Hilden/Rhld.,
DT), Bellinger; Horst (Dusseldorf, DT) |
Assignee: |
Henkel & Cie G.m.b.H.
(Dusseldorf, DT)
|
Family
ID: |
25980481 |
Appl.
No.: |
05/088,486 |
Filed: |
November 10, 1970 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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656136 |
Jul 26, 1967 |
3637495 |
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Foreign Application Priority Data
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Aug 1, 1969 [DT] |
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H 60 12 48 |
May 23, 1967 [DT] |
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H 62 81 68 |
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Current U.S.
Class: |
510/518 |
Current CPC
Class: |
C11D
3/32 (20130101); C11D 1/525 (20130101); C11D
3/001 (20130101); D06M 13/372 (20130101) |
Current International
Class: |
C11D
3/32 (20060101); D06M 13/372 (20060101); D06M
13/00 (20060101); C11D 1/38 (20060101); C11D
3/00 (20060101); C11D 3/26 (20060101); C11D
1/52 (20060101); D06m 013/40 (); D06m 013/46 () |
Field of
Search: |
;252/8.8,8.9,8.6
;117/139.5F,143,139.5CQ ;260/404,211 |
References Cited
[Referenced By]
U.S. Patent Documents
Primary Examiner: Guynn; Herbert B.
Parent Case Text
RELATED APPLICATION
This application is a continuation -in- part of "Agent for the
Post-Treatment of Laundry", filed July 26, 1967, the applicable
priority document being on file in the parent application, Ser. No.
656,136, now U.S. Pat. No. 3,637,495.
Claims
We claim:
1. A laundry textile antimicrobial and softening composition
consisting esentially of 0.5 to 30 weight percent of a
water-soluble, heavy metal-free, non-oxidizing antimicrobial agent
selected from the group consisting of nitrated polyalcohols and a
quaternary ammonium compound, and about 2 to 70 weight percent of a
textile fabric softening glycamide of the formula: ##SPC3##
wherein:
R.sub.1 = (1) alkyl of 10 to 22 carbon atoms or, (2) alkyl of 10 to
22 carbon atoms with an ether oxygen linkage between either the two
and three or 3 and 4 carbon atoms from the nitrogen atom,
R.sub.2 = alkyl of seven to 21 carbon atoms,
R.sub.1 + r.sub.2 have 23 to 39 carbon atoms.
2. The composition of claim 1 in solid form wherein said glycamide
comprises 10 to 30 weight percent thereof.
3. The composition of claim 2 in the form of a solution wherein
said glycamide comprises 2 to 30 weight percent thereof, and, other
than said antimicrobial agent, the balance being water or a
water-soluble organic solvent selected from the group consisting of
unsubstituted aliphatic monohydric alcohols of one to four carbon
atoms, ether alcohols thereof formed by the reaction of said
aliphatic alcohols with a glycol selected from the group consisting
of ethylene glycol, diethylene glycol, propylene glycol, and
butylene glycol, lower ketones, and monoethers or diethers formed
by reacting said aliphatic alcohols with glycerine.
4. The composition of claim 3 wherein said nitrated polyalcohols is
2-bromo-2-nitro-propanediol - 1, 3, and wherein said quaternary
ammonium compound is N-dodecyl-N-benzyl-N, N-dimethyl ammonium
chloride.
Description
THIS INVENTION
It has now been found that the glycamides disclosed in the parent
application can be used effectively with certain water-soluble
antimicrobial agents to both disinfect and soften textile
fabrics.
The glycamides have the formula given in the Abstract of the
Disclosure. Preferably R.sub.1 represents an alkyl radical having
10 to 22, preferably 12 to 20, and most preferably 16 to 18 carbon
atoms, R.sub.2 represents an alkyl radical having 7 to 21,
preferably 11 to 19, and most preferably 15 to 17 carbon atoms, and
n is either of the whole numbers 3 or 4, further wherein the alkyl
radical R.sub.1 can be interrupted by an ether oxygen atom in the
vicinity of the N-atom, and the sum of the carbon atoms contained
in R.sub.1 and R.sub.2 amounts to at least 23 and preferably to
from 27 to 35. Preferably n = 4, i.e., N-alkyl-N-acylglycamines are
employed as softening agents. The latter will hereinafter be called
"glycamides" for the sake of simplicity. The data given on the
glycamide softening agents also apply accordingly to compounds
wherein n = 3.
The term antimicrobial agents as used herein is understood to mean
both bactericidal and bacteriostatic, and fungicidal and/or
fungistatic products. The antimicrobial agents are required to be
water soluble either per se or in the form of their salts. Examples
of suitable antimicrobial agents for use herein are formaldehyde,
halogenated phenols, nitrated mono- or polyalcohols, and
antimicrobial surfactants.
The present composition can be use in the treatment of washed
textiles, alone or together with other conventional laundry
detergents and post-treatment agents, such as acidifiers or
disincrusting agents, optical brighteners; and may be made and
marketed in powdered or liquid form, as is customary.
The textiles fabrics or other laundered items which have been
rinsed with the products fabrics of the invention, possess, after
drying, not only a high degree of fullness and softness, but they
also possess excellent absorbency. Furthermore, the sotening agents
of the invention are quite compatible with anionic optical
brightening agents. If any of the above-mentioned antimicrobial
agents are used, not only are any microbes that might be present in
the washed textiles or in the rinse water killed, but often
anti-microbial properties are conferred upon the post-treated
textiles.
The glycamides to be used in the method of the invention or
contained in the preparations according to the invention can be
prepared by amidation in the known manner from the appropriate
glycamines which can be produced by the hydrogenation of hexoses or
their oligomers using therefor Raney nickel catalyst in the
presence of higher alkyl amines.
The principal hexoses involved are monosaccharides such as glucose,
mannose, galactose, fructose, sorbose or their mixtures such as
invert sugar; however, their oligomers can also be used, such as
maltose, for example. Instead of hexoses, pentoses, mixtures of
pentoses or mixtures of pentoses and hexoses can be used.
The amines suitable for use in the reaction are primary
alkylmonamines. The alkyl radicals of these amines, like the alkyl
radicals of the fatty esters to be used in the amidation, can be
saturated or unsaturated, straight-chained or branched, and of
synthetic or natural origin. The radicals R.sub.1 present in the
glycamides can be derived from decyl, lauryl, myristyl, cetyl,
stearyl, oleyl, arachyl, or behenyl amine. There are also suitable
those amines whose carbon chain is interrupted by an ether oxygen
atom in the vicinity of the N-atoms, preferably between carbon
atoms 2 and 3 or 3 and 4 (counting from the N-atom). Such amines,
in which the NH.sub.2 group and the ether oxygen atom are separated
from one another by three carbon atoms, are obtained for example by
addition of acrylonitrile to a suitable fatty alcohol followed by
reduction of the nitrile group.
The fatty acid radicals R.sub.2 --CO-- can be derived from capric,
lauric, myristic, palmitic, stearic, oleic, arachic or behenic
acid. Glycamides can also be used in which the amine and/or the
fatty acid radicals are present as isomer mixtures, such as those
which can be obtained from fats of natural origin. Accordingly,
these amines and fatty esters can be made from the fats derived
from plants, land or marine animals, as for example, from coconut
oil, palm oil, linseed oil, cottonseed oil, peanut oil, rapseed oil
etc., from hog lard, tallow or fish or whale oil or from fractions
of the fatty acids contained in these fats. The amines or fatty
esters to be used are not to be excessively unsaturated i.e., they
are not to have an iodine number higher than 50, and preferably not
higher than 30. In fact, even substantially completely hardened
products having iodine numbers below 10 and preferably below 5 can
be used.
The methyl esters which are employed are preferably fatty acid
esters. There can, however, be used to equal advantage the esters
of monoalcohols having two to four carbon atoms, as for example,
the esters of ethyl, propyl, isopropyl, butyl and isobutyl alcohol
etc. Suitable for use herein are also the fatty acid
glycerides.
The amidation of the alkylglycamines is carried out by heating the
fatty esters with the amines at temperatures of 150.degree. to
170.degree.C, preferably with agitation. The course of the reaction
can easily be observed by intercepting the alcohol released by the
reaction. When the amount of liberated alcohol has reached
approximately the theoretical, the reaction is stopped. In no case
is the reaction mixture or the reaction product that has been
formed to be heated so intensely or so long as to produce
dehydration.
The glycamide thus obtained can be used directly for the purposes
of the invention. If desired, however, it can first be purified, as
for example by recrystallization. The glycamides are moderately
soluble in water, but are readily soluble in water-soluble organic
solvents, such as univalent or polyvalent alcohols having one to
four carbon atoms, or in ether alcohols, such as the monoethers
formed by reaction of the above-mentioned univalent alcohols with
ethylene glycol, diethylene glycol, propylene glycol, butylene
glycol, or by the monoethers or diethers of the said univalent
alcohols formed by reaction of the univalent alcohols with
glycerine. The glycamides are also soluble in the lower
water-soluble ketones. The aforesaid solvents, particularly those
having boiling points below 100.degree.C, are also suitable for the
recrystallization of the glycamides.
In accordance with the invention, the washed textiles or other
laundered items are contacted with a rinse water containing the
glycamides in concentrations of approximately 0.05 to about 2 grams
per liter and preferably from 0.1 to about
The glycamides can be used directly in the first rinse, even if the
remains of the washing medium have not been completely washed out
of the goods. Since, of course, it has become an established
practice to add the softening agent to the final rinse, the same
can, obviously be done when using the glycamides of the invention
or the softening agents containing them.
After the rinse, as effected in accordance with the invention, the
laundry is dried in the conventional manner. The laundry is soft
and full and has a pleasant feel, which becomes pleasantly
observable especially in the case of articles which come in contact
with the skin, such as underwear, bed linen and handkerchiefs. In
particular, wash and drying cloths exhibit a remarkably good
absorbency, which is greatly appreciated in the case of dishtowels
and bath towels. Further the moist articles which have been
soft-rinsed according to the invention yield their moisture more
quickly than others on being subjected to drying. Finally, the
textiles thus treated are observed to iron more easily than the
conventionally laundered articles.
Since the glycamides act on the textiles or other laundered items
for only a relatively short period especially in the case of
automatic washing machines, it is advantageous to use the
moderately water-soluble glycamides in finely divided form. This is
accomplished in accordance with the invention by using the
post-treatment agents in solid or liquid form and in a form in
which the glycamide is mixed together with the conventional solid
or liquid diluents and/or fillers.
Water-soluble inorganic, preferably weakly alkaline, neutral or
weakly acid substances are suitable for use as solid fillers. For
the manufacture of solid preparations, inorganic or organic salts
are of primary importance, as for example the alkali salts of
sulfuric acid, orthophosphoric acid or pyrophosphoric acid.
However, salts of organic acids can also be used, such as the
non-surface-active salts of carboxylic acids or hydroxycarboxylic
acids having one to 10, preferably one to six carbon atoms, as for
example, salts of acetic acid, propionic acid, lactic acid, citric
acid, tartaric acid, benzoic acid, phthalic acid, etc.
Water-soluble inorganic or organic acid amides or their salts may
also be present as solid fillers, as for example, amidosulfuric
acid salts, amidophosphoric acid salts and water-soluble amides or
carboxylic acids, such as urea, acetamide, etc. Solid polyethylene
glycols are also usable as fillers.
The solid post-treating agents of the invention can be prepared for
example by spraying a solution or dispersion of the glycamides in a
suitable liquid onto the finely divided solid filler substances. It
is also possible to spray aqueous solutions or suspensions of
glycamides having a percentage of fillers dissolved or dispersed
therein, in the known manner, and thus to obtain readily soluble
powders or granules. Lastly, solutions or dispersions of the
glycamides in fused urea or in fused polyethylene glycols can be
sprayed or otherwise converted into easily soluble powders or
granules.
The time which is required for the glycamides added as concentrates
to the rinse water to reach the desired concentration for use can
be still further reduced by using liquid products in which the
glycamides are dissolved in a solvent or dispersed in water. In
this manner no time is lost i.e., taken up in the dissolution of a
solid filler, and instead the desired concentration for use
establishes itself immediately after the addition of the liquid
concentrate to the rinse water.
The liquid aqueous concentrates are prepared by dispersing the
moderately water-soluble glycamides in an aqueous phase. It has
proved advantageous for the glycamides first to be dissolved in one
of the above-named water-soluble organic solvents and thereafter
for the resulting solutions to combine with water. The solid
glycamides thereupon separate in finely divided form, the organic
solvents serving as solubilizers. These aqueous solutions can of
course contain any of the above-named solid fillers if the
stability of dispersion is not adversely affected thereby. In many
cases the stability may be improved by such addition. For this
purpose, the alkali salts of lower carboxylic acids or
hydroxycarboxylic acids containing up to 6 carbon atoms, and urea
or acetamide have proved particularly suitable and can be used
instead of, or together with the above-mentioned water-soluble
organic solvents serving also as solubilizers.
The known dispersing and emulsifying agents or emulsion stabilizers
can be used for effecting the stabilization of the aqueous
glycamide dispersions.
Suitable dispersing or emulsifying agents include the known anionic
or non-ionic wash-active substances whose action is based on the
simultaneous presence of one hydrophobic and one hydrophilic
radical in their molecules. The hydrophobic radical consists
usually of an alkyl radical having eight to 20, preferably 12 to 18
carbon atoms. Anionic or non-ionic groups are suitable as
hydrophilic radicals. The anionic groups include carboxyl, sulfonic
acid or sulfurnic acid semi-ester groups; the non-ionic groups
include aggregations of hydroxyl groups or polyethylene glycol
ether chains. Accordingly, alkylbenzenesulfonates, fatty alcohol
sulfates, fatty alcohol glycol ether sulfates having one to five
ethylene glycol ether radicals in the molecule, fatty acid
monoglycerides, polyethylene glycol ethers of fatty alcohols or
alkylphenols having five to 20 ethylene glycol ether radicals in
the molecule are suitable for use as dispersing and emulsifying
agents. In no case, however, must the amount of these dispersing
and emulsifying agents be greater than the amount of the glycamide
present and preferably the dispersing or emulsifying agent should
be present in substantially lesser quantities amounting to at the
most to 50%, and preferably amounting to from 5 to 25% of the
glycamides.
Suitable emulsion stabilizers include the water-soluble colloids,
such as the salts of ether carboxylic acids or ether sulfonic acids
of cellulose, cellulose sulfate, polyacrylic acid or
polymethacrylic acid salts, water-soluble polyacrylamides and
polyethylene glycols, preferably those having a molecular weight
greater than 600, and particularly the solid polyethylene glycols.
Many of these emulsion stabilizers produce a great increase in the
viscosity of the aqueous solutions, and therefore they are used in
quantities preferably of less than 1% so that the post-treatment
agents will still be readily fluid in nature. Others, particularly
the polyethylene glycols, can be used in substantially greater
quantities, without raising the viscosity to undesirable
levels.
The glycamides according to the invention and the compositions
containing such glycamides can advantageously be combined with
other substances which have heretofore been used as post-treatment
agents. These include, for example, optical brighteners, acidifying
and disincrusting agents, colorants, perfumes, etc. These
substances can be incorporated into the solid or liquid
post-treatment agents according to the invention.
The combined use of the above-described softening agents with
optical brighteners is to be considered as an important and novel
feature of the invention. The brighteners are intended mainly for
cellulose fibers, but brighteners for cellulose and/or other
fibers, especially synthetic fibers, can be used as well.
Suitable additives for acidification and/or for the removal of ash
or other fiber incrustations include the non-oxidizing acids which
have been found to be not harmful to the fibers to be treated and
particularly those additives which form soluble alkaline earth
metal salts, and complex compound formers. The acid reacting
substances include for example amidosulfuric acid, urea compounds
or orthophosphoric acid or solid organic acids like citric acid.
The complex compound formers include for example tripolyphosphates
or the higher but still water soluble polyphosphates of alkalies,
salts of nitrilotriacetic acid, ethylenediamine tetracetic acid,
N-oxyethylethylenediaminetriacetic acid and other conventional
organic complex compound forming agents, such as the salts of
certain di-, tri- or tetraphosphonic acids.
As instances of halogenated phenols which may be used as
antimicrobials, there may be mentioned, for example, chlorination
and bromination products of phenol, such as pentachlorophenol, and
also halogenated cresols, xylenols, such as 4-bromo-3,5-xylenol or
halogenated cyclohexylphenols, methylcyclohexylphenols or
benzylphenols.
There may also be used the water-soluble antimicrobial substances
of the cationic or hybrid ionic surfactant type, which serve in the
final post-treatment agents also as dispersing agents.
Instances of cationic substances which are suitable as
antimicrobials include quaternary ammonium compounds which contain
on the nitrogen atom thereof an aliphatic hydrocarbon radical
containing eight to 18, and preferably 10 to 14 carbon atoms, or
alternatively contain on the nitrogen atom at least one aromatic
radical or a radical having double bonds, the latter radical being
linked to the nitrogen atom by an aliphatic carbon atom. The
following are instances of the cationic compounds suitable for use
in the invention include: diethylbenzyldodecyl ammonium chloride,
diethylbenzyloctyl ammonium chloride, and dibutylallyl,
methylethylbenzyl, ethylcyclohexylallyl and
ethylcrotyldiethylaminoethyl dodecyl ammonium chloride.
There are also tertiary amines suitable for use which can be
prepared by condensing a primary or secondary amine containing up
to four basic nitrogen atoms and one aliphatic or alkylaromatic
radical having eight to 18 and preferably eight to 14 aliphatic
carbon atoms with a phenol or lower aliphatic aldehyde, preferably
formaldehyde or acetaldehyde. The phenol employed in the
condensation reaction may have in its molecule a plurality of sites
capable of condensation, and these may be substituted with lower
alkyl, alkoxyl or benzyl radicals containing up to four carbon
atoms. The phenyl, alkyl, alkoxyl and benzyl radicals may
additionally be substituted with chlorine or bromine atoms and/or
with nitro groups. Examples of such condensation products include,
for instance, the following compounds: oxybenzyloctylamine,
oxybenzyldodecyldiethylenetriamine,
(2-oxy-5-chloro-6-methylbenzyl)-dodecyldiethylenetriamine,
(2-oxy-5-methyl-benzyl)octyldiethylenetriamine,
(2-oxy-5-chloro-4,6-diemethylbenzyl)octyldiethylenetriamine,
(tris-oxybenzyl)-dodecyltriethylenetetramine,
o,o-bis-(tetradecylaminomethyl)-p-cresol,
o,o-bis(dodecyldiethylenetriaminomethyl)-p-chloro-m-cresol,
m,m-bis(dodecyldiethylenetriaminomethyl)-p-oxybenzoic acid,
2,2-bis-p-oxy-m,m-di-(dodecyldiethylenetriaminomethyl)-phenolpropane,
o,o-bis-(dodecyldiethylenetriaminomethyl)-p-nitrophenol,
o,o-bis-(dodecylpropylenediaminomethyl)-p-chloro-m,m-dimethylphenol
etc. The aforesaid tertiary amine compounds have a weakly acid
reacting hydroxyl group and thus represent an intermediate type
between the purely cationic and the hybrid-ionic surfactants.
The hydrid-ionic surfactants which have achieved particular
importance as antimicrobials include compounds of the
aminocarboxylic acid, polyaminocarboxylic acid and betaine
type.
Illustrative of the aminocarboxylic and polyaminocarboxylic acid
antimicrobial agents are compounds having the following structural
formula:
R.sub.4 -- NH -- (R.sub.5 --NH).sub.x -- R.sub.3 -- COOH
wherein R.sub.4 represents an alkyl or alkylaryl radical of high
molecular weight, preferably such a hydrocarbon radical having six
to 18 and most preferably eight to 14 aliphatic carbon atoms,
R.sub.5 represents an ethylene or propylene radical, x represents a
whole number of from 1 to 6 and R.sub.3 represents an
aliphatic-aromatic or aromatic bridge having one to six carbon
atoms. The following compounds are illustrative of aminocarboxylic
and polyaminocarboxylic compounds having the above mentioned
formula: dodecylaminopropylglycine,
tetradecylaminoethyl-.beta.-alanine,
dodecyl-di-(aminoethyl)-glycine,
dodecylaminoisopropylaminomethylsalicylic acid,
hexadecyl-tri-(aminoethyl)-.beta.-aminobutyric acid,
dodecylbenzylaminopropyl-.beta.-alanine,
octylphenoxyethyl-di-(aminoethyl)-glycine,
dodecylaminoethylphenylalanine, dodecylaminoethylaminobenzoic acid,
etc.
The radical R.sub.4 can also be interrupted by an ether oxygen
atom, as is the case, for example, in the following compounds:
dodecyloxypropylaminopropionic acid,
lauryl-1,3-oxypropyl-.beta.-aminobutyric acid, C.sub.12-14
-alkyloxyethylaminoacetic acid,
dodecyl-1,2-oxypropylaminomethylsalicylic acid,
octylphenoxyethylaminobenzoic acid.
The compounds that can be used according to the invention
furthermore include carboxybetaines of the formula: ##SPC2##
which can be used both in the betaine form, i.e., in the form of
inner salts, and in the form of acidic or basic salts. R.sub.4 has
the same meaning as in the preceding formula, R.sub.7 represents an
ethylene or propylene group, and R.sub.6, R.sub.8 and R.sub.9
represent aliphatic bridges of low molecular weight, X an ether
oxygen atom or the --CONH-- group. Examples of such carboxybetaine
compounds are lauroyl-1,3-amidopropyldimethyl-aminoacetic acid,
lauryloxyethyldi-(hydroxyethyl)-aminopropionic acid,
octylphenoxyethyldi-(hydroxyethyl)-aminoacetic acid, etc.
The antimicrobial agents can be combined in any desired manner with
solid or liquid diluents or fillers, with hydrotropic substances,
with dispersing and emulsifying agents, with emulsion stabilizers,
with brighteners and with acidification and disincrusting
agents.
The amounts of the antimicrobial agents contained in the solid or
liquid laundry post-treatment agents can vary within wide limits
according to the subsequent intended use of the laundered articles,
amounting to 0.5 - 30% and preferably 1 - 20% by weight. If the
antimicrobial agents are hybrid-ionic surface active substances,
their quantity is always smaller than the quantity of the softening
agent; preferably the quantity of the hybrid-ionic surface-active
antimicrobial agents amounts to no more than 50% of the quantity of
the softening agent.
The laundry post-treatment agents according to the invention as
noted above constitute solid products and as such have the
following composition :
30 - 95 and preferably 70 - 90 wt-% of solid vehicle substance
70 - 5 and preferably 30 - 10 wt-% glycamide
0 - 20 and preferably 1 - 15 wt-% of an optical brightener, the
same being present in a quantity amounting to 5 to 25% of the
amount of glycamide present;
0 - 30 and preferably 1 - 15 wt-% of a surface active dispersing or
emulsifying agent, the quantity thereof always being less than the
amount of the glycamide and preferably no more than 50% and most
preferably from 5 to 25% of the amount of glycamide;
0 - 20 and preferably 0.1 - 10 wt-% of an emulsion stabilizer or
thickening agent, the quantity thereof being regulated so that a
10% aqueous solution or dispersion of the entire solid preparation
will have a good fluidity;
0 - 30 and preferably 1 - 20 wt-% of at least one of the
above-mentioned antimicrobial agents, with the proviso that if they
are antimicrobial hybrid-ion surfactants, the quantity thereof is
always to be smaller than the quantity of the glycamide, amounting
preferably to no more than 50% and most preferably to from 5 to 25%
of the quantity of the glycamide.
The liquid, laundry post-treatment preparations in accordance with
the invention have the following composition :
2 - 30 and preferably 5 - 15 wt-% glycamide.
0 - 50 and preferably 5 - 30 wt-% solid water-soluble hydrotropic
substance and/or water-soluble organic solvent.
0 - 10 and preferably 1 - 8 wt-% of an optical brightener but
preferably such a quantity of optical brightener as to amount to 5
to 25% of the amount of the glycamide.
0 - 10 and preferably 0 - 5 wt-% of a surface active emulsifying or
dispersing agent, the amount thereof always being less than the
amount of glycamide and amounting preferably to no more than 50,
and most preferably 5 to 25 wt-% of the amount of glycamide.
0 - 20 and preferably 0.1 - 10 wt-% of a water-soluble emulsion
stabilizer or thickening agent, the quantity thereof, however,
being regulated so that the final preparation will have good
fluidity.
0 - 30 and preferably 1 - 20 wt-% of at least one of the
above-named antimicrobial agents; if they are antimicrobial
hybrid-ion surfactants, the quantity thereof always being less than
the quantity of the glycamide, amounting preferably to no more than
50% and most preferably from 5 to 25% of the quantity of the
glycamide. Balance water.
In the liquid preparations the water can be entirely replaced by
water-soluble organic solvents, or at least to such an extent that
all of the components and especially the glycamide, are
dissolved.
The Examples given hereinafter serve to illustrate the invention
without being in any way or form considered as limitative of the
scope of the same.
The glycamides incorporated into the softening agents of the
invention and tested in the manner to be described below were
prepared on the basis of the following procedure:
In a three-necked flask equipped with a gas feed tube, agitator,
condenser, and a receiver for the distillate, a mixture of 0.22
mole of N-alkylglycamine and 0.20 mole of fatty acid methyl ester
was heated slowly under a current of nitrogen, with intense
agitation, to 150.degree. to 170.degree.C. The methanol released in
the reaction was distilled off and held in a graduated receiver.
The reaction mixture was maintained at 150.degree. to 170.degree.C
until about 75 to 80% of the theoretical amount of methanol had
passed over. This required from 2 to 5 hours depending on the
starting material. Thereafter the rest of the methanol was removed
by two hours of heating in vacuo; the methanol was frozen out in a
cooling trap. As soon as 94 to 98% of the theoretical amount of
methanol had been recovered, the reaction was ended.
The N-alkyl-N-acyl glycamines thus prepared were in the form of
pastes or solids, depending on the chain length and on the chain
length distribution of the alkyl or acyl radicals. If desired, they
could be purified by recrystallization from the water-soluble
organic solvents mentioned previously, or from benzene or acetic
acid ethyl ester.
The advantageous effects that are achieved with the aforesaid
glycamides i.e. high degree of softness, fullness and absorbency
were demonstrated in tests carried out on ordinary cotton fabrics
and on cotton terrycloth fabrics, which tests are described fully
in the parent application.
EXAMPLE 1
Glucamide R.sub.1 = C.sub.12 H.sub.25 ; R.sub.2 = C.sub.17 H.sub.35
; Total 29 C atoms
Feel: 2.0
Compressibility: Vertical Absorbency: Absorption value: Z.sub.% =
127 St.sub.x = 68% S.sub.x = 75% .DELTA. Z.sub.% = 27 66 St.sub.y =
200% .DELTA. S.sub.y > 1700%
EXAMPLE 2
Glucamide R.sub.1 = C.sub.14 H.sub.29 ; R.sub.2 = C.sub.15 H.sub.31
; Total 29 C atoms
Feel: 2.0
Compressibility: Vertical Absorbency: Absorption Value: Z.sub.% =
122 St.sub.x = 52% S.sub.x = 36% .DELTA. Z.sub.% = 22 .DELTA.
St.sub.y = 140% .DELTA. S.sub.y > 800%
EXAMPLE 3
Glucamide R.sub.1 = C.sub.3 H.sub.6 OC.sub.16 H.sub.33 ; R.sub.2 =
C.sub.15 H.sub.31 ; Total 34 C atoms
Feel: 1.5
Compressibility: Vertical Absorbency: Absorption Value: Z.sub.% =
132 St.sub.x = 47% S.sub.x = 23% .DELTA. Z.sub.% = 32 .DELTA.
St.sub.y = 120% .DELTA. S.sub.y > 470%
EXAMPLE 4
Glucamide R.sub.1 = C.sub.16 H.sub.33 ; R.sub.2 = C.sub.11 H.sub.23
; Total 27 C atoms
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value Z.sub.% =
143 St.sub.x = 30% Not determined because of .DELTA. Z.sub.% = 43
.DELTA. St.sub.y = 35% lack of substance
EXAMPLE 5
Glucamide R.sub.1 = C.sub.18 H.sub.37 ; R.sub.2 = C.sub.7 H.sub.15
; Total 25 C atoms
Feel: 1.5
Compressibility: Vertical Absorbency: Absorption Value Z.sub.% =
134 St.sub.x = 36% Not determined because of .DELTA. Z.sub.% = 34
.DELTA. St.sub.y = 61% lack of substance
EXAMPLE 6
Glucamide R.sub.1 = C.sub.12.sup.- C.sub.18.sup.- mixture of
coconut fatty acids, avg. = about C.sub.13
R.sub.2 = c.sub.15.sup.+ c.sub.17.sup.- mixture of tallow fatty
acids, avg. = about C.sub.16
total about 29 carbon atoms
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value Z.sub.% =
143 St.sub.x = 59% S.sub.y = 67% .DELTA. Z.sub.% = 43 .DELTA.
St.sub.y = 180% .DELTA. S.sub.y > 1500%
EXAMPLE 7
Glucamide R.sub.1 = C.sub.16.sup.+ C.sub.18.sup.- mixture of tallow
fatty acids, avg. = about C.sub.17
R.sub.2 = c.sub.11.sup.- c.sub.17.sup.- mixture of coconut fatty
acids, avg. = about C.sub.13
total about 30 C atoms.
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value: Z.sub.% =
144 St.sub.x = 34% S.sub.x = 20% .DELTA. Z.sub.% = 44
.DELTA.St.sub.y = 60% S.sub.y > 400%
EXAMPLE 8
Fructamide R.sub.1 = C.sub.12.sup.- C.sub.18.sup.- mixture of
coconut fatty acids avg. approx. C.sub.13
r.sub.2 = c.sub.15.sup.- c.sub.17.sup.- mixture of tallow fatty
acids avg. approx. C.sub.16
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value Z.sub.% =
147 St.sub.x = 40% S.sub.x = 23% .DELTA. Z.sub.% = 47 .DELTA.
St.sub.y = 79% S.sub.y > 470%
EXAMPLE 9
Glycamide mixture from invert sugar
R.sub.1 = c.sub.12.sup.- c.sub.18.sup.- mixture 18.sup.-coconut
fatty acids, avg. approx. C.sub.13
r.sub.2 = c.sub.15.sup.- c.sub.17.sup.- mixture of tallow fatty
acids, avg. approx. C.sub.16
Total approx. 29 C atoms
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value Z.sub.% =
155 St.sub.x = 46% S.sub.x = 23% .DELTA. Z.sub.% = 55 .DELTA.
St.sub.y = 100% S.sub.y > 490%
EXAMPLE 10
Glycamide mixture from invert sugar
R.sub.1 = c.sub.16.sup.- c.sub.18.sup.- mixture of tallow fatty
acids avg. approx. C.sub.17
r.sub.2 = c.sub.11.sup.- c.sub.17.sup.- mixture of coconut fatty
acids avg. approx. C.sub.12
Total approx. 29 C atoms
Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value Z.sub.%
St.sub.x = 34% Not determined because of in- .DELTA. Z.sub.%
.DELTA. St.sub.y = 62% sufficient substance
EXAMPLE A
A post-treatment agent according to the invention for use with
textiles having the following composition was prepared:
10 wt-% glucamide according to Example 6
30 wt-% isopropanol
2 wt-% ethoxylated dimethylpolysiloxane
1 wt-% 2-bromo-2-nitro-propanediol-1,3
10 wt-% tartaric acid
47 wt-% water
EXAMPLE B
A post-treatment agent for use with conventional laundry having the
following composition was prepared:
10 wt-% glucamide according to Example 1
60 wt-% isopropanol
2 wt-% ethoxylated dimethylpolysiloxane
2 wt-% N-dodecyl-N-benzyl-N,N-dimethyl ammonium chloride 10 wt-%
tartaric acid
16 wt-% water
The glycamide incorporated into the preparations of Examples A and
B are replaced by any of the compounds of Examples 2-5 or 7-10, to
secure after-rinsing agents having a similar action
* * * * *