COMPOSE LIQUIDE EN CONCENTRATION POUR L'ASSOUPLISSEMENT DES TISSUS

CONCENTRATED LIQUID FABRIC SOFTENER COMPOSITION

Abrégé anglais

CONCENTRATED LIQUID FABRIC SOFTENER COMPOSITION
Abstract of the Disclosure
Concentrated liquid fabric softeners containing a
fabric substantive agent, inclusive of polyamines and
alkylpyridinium salts, in conjunction with a fabric
softening component, inclusive of quaternary ammonium
salts; alkylimidazolinium salts; fatty esters; fatty
ethers; and fatty compounds containing a sulfur or
nitrogen linking atom, are disclosed. The subject
concentrated softener compositions are easily dispersible
in aqueous medium and thus can evenly deposit onto fibers
to thereby provide textile handling benefits inclusive of
softening, static control, ease-of-ironing, fluffiness,
pliability and smoothness.

Revendications

The embodiments of the invention in which an exclusive
property or privilege is claimed are defined as follows:
1. A concentrated liquid fabric softener having
improved pourability and water-dispersability character-
istics comprising from about 25% to about 55% by weight of
an active system comprised of a fabric-substantive agent
and a fabric-softening component, the fabric-substantive
agent being selected from the group of:
(1) a compound having the formula
<IMG>
wherein R is selected from an alkyl or alkenyl group having
from 10 to 24 carbon atoms in the alk(en)yl chain and
R-O-(CH2)n1-; the R1's which may be the same or
different each represent hydrogen, -(C2H4O)pH, -(C3H6O)
qH, -(C2H4O)p, (C3H6O)q, H, a C1-3 alkyl group or the group
- (CH2)n2 - N(R')2, wherein R' is selected from hydrogen, -
(C2H4O)p-H, - (C3H6O)qH, -(C2H4O)p, (C3H6O)q, H and a
C1-3 alkyl group, where n, n1 and n2 each represent an
integer from 2 to 6, m is an integer from 1 to 5, each p,
q and (p'+q') may be 0 or a number such that (p+q+p'+q')
does not exceed 25, and, if in the salt or partial salt
form, A(-) represents one or more anions having total
charge balancing that of the nitrogen atom(s);
(2) an alkylpyridinium salt wherein the alkyl
chain has from about 10 to 24 carbon atoms; and
(3) mixtures thereof; with the proviso that the
fabric-substantive agent has a water-solubility of more
than about 5% by weight at pH 2.5 and 20°C., the fabric-
softening component being selected from the group of:
23

(a) a quaternary ammonium salt having the formula
<IMG>
wherein R2 and R3 represent hydrocarbyl groups having from
12 to 24 carbon atoms, R4 and R5 represent hydrocarbyl
groups having from 1 to 4 carbon atoms, and X is an anion;
(b) an alkylimidazolinium salt having the formula
<IMG>
wherein R6 is a C1-4 alkyl group, R9 is hydrogen or a C1-4
alkyl group, R8 is a C8-25 alkyl group; and R7 is a C9-25
alkyl group; and A? is an anion;
(c) a fatty ester of mono- or polyhydric
alcohols having from 1 to about 24 carbon atoms in the
hydrocarbon chain, and mono- or polycarboxylic acids having
from 1 to about 24 carbon atoms in the hydrocarbon chain
with the provisos that the total number of carbon atoms in
the ester is equal to or greater than 16 and that at least
one of the hydrocarbon radicals in the ester has 12 or more
carbon atoms;
(d) ethers of fatty alcohols having from 10 to
24 carbon atoms in the alkyl chain and mono- or poly-
alcohols having from 2 to 8 carbon atoms, whereby the total
number of carbon atoms in the ether is equal to or greater
than 16;
(e) compounds of the formula R10-X-R11 wherein
R10 has from about 12 to 24 carbon atoms and Rll from 1 to
6 carbon atoms in the alkyl chain which can be interrupted
23

by not more than one oxygen link, and X stands for sulfur,
<IMG> ; or <IMG> ;
and
(f) mixtures thereof, whereby the weight of the
fabric-substantive agent to the fabric-softening component
is in the range from about 6:1 to about 1:4; and a liquid
carrier.
2. The composition in accordance with claim 1
wherein the fabric-substantive agent is present in an
amount from about 50% to about 85% by weight and the
fabric-softening component selected from (a) and (b) is
present in an amount from about 15% to about 50% by
weight, the amounts of the components being expressed by
reference to their sum.
3. The composition in accordance with claim 1
wherein the fabric-substantive agent is present in an
amount from about 25% to about 85% by weight and the
fabric-softening component selected from (c), (d) and (e)
is present in an amount from about 15% to about 75% by
weight, the amounts of the components being expressed by
reference to their sum.
4. The composition in accordance with claim 1
wherein R1 in the fabric-substantive agent is -
(C2H4O)pH or -(C3H6O)qH or -(C2H4O)p, (C3H6O)q'
where each of p, q, and (p'+q') are 1 or 2.
5. The composition in accordance with claim 2
wherein the fabric-substantive agent is present in an
amount from about 65% to about 80% by weight and the
fabric-softening component selected from (a) and (b) is
present in an amount from about 20% to about 35% by
weight, the amounts of the components being expressed by
reference to their sum.
24

6. The composition in accordance with claim 3
wherein the fabric-substantive agent is present in an
amount from about 35% to about 65 by weight and the
fabric-softening component selected from (c), (d) and (e)
is present in an amount from about 65% to about 35% by
weight, the amounts of the components being expressed by
reference to their sum.
7. The composition in accordance with claim 1
wherein the fabric-substantive agent represents from
about 25% to about 65% by weight and wherein the
fabric-softening component is represented by a binary
system containing from about 8% to about 35% of the
fabric-softening component selected from (a) and (b) and
from about 15% to about 60% of the fabric-softening
component selected from (c), (d) and (e), the amounts of
the components being expressed by reference to their sum.
8. The composition in accordance with claim 1,
wherein the fabric-substantive agent is selected from the
group consisting of:
N-tallowyl, N,N',N'-tris(2-hydroxyethyl)1,3-
propanediamine di-hydrochloride:
N-soybean alkyl-1,3-propane diammonium sulfate;
N-stearyl-N,N'-di(2-hydroxyethyl)-N'-(3-hydroxy-
propyl)-1,3-propanediamine dihydrofluoride;
N-cocoyl N,N,N',N',N'-pentamethyl-1,3-propane
diammonium dichloride or dimethosulfate;
N-oleyl N,N',N'-tris(3-hydroxypropyl)-1,3-
propanediamine dihydrofluoride;
N-stearyl N,N',N'-tris(2-hydroxyethyl)N,N'-
dimethyl-1,3-propanediamonium dimethylsulfate;
N-palmityl N,N',N'-tris(3-hydroxypropyl)-1,3-
propanediamine dihydrobromide;

N-(stearyloxypropyl) N,N',N'-tris(3-hydroxy-
propyl)1,3-propanediammonium diacetate;
N-tallowyl N-(3-aminopropyl)1,3-propanediamine
trihydrochloride;
N-oleyl N-[N",N"bis(2-hydroxyethyl)3-amino-
propyl]N',N'-bis(2-hydroxyethyl)1,3 diaminopropane
trihydrofluoride.
1-[N-hydrogenated tallowylaminopropyl]-
pentahydropyridinium dihydrochloride;
1-[N-stearylaminopropyl]-5-(hydroxyethyl)-
tetrahydropyridinium sulfate; and C16-18 alkylpyridinium
chloride or bromide.
9. The composition in accordance with claim 8
wherein the fabric-softening component is selected from
the group consisting of:
ditallow dimethyl ammonium chloride; ditallow
dimethyl ammonium methyl sulfate; dihexadecyl dimethyl
ammonium chloride; di(hydrogenated tallow) dimethyl
ammonium chloride; dioctadecyl dimethyl ammonium chloride;
dieicosyl dimethyl ammonium chloride; didocosyl dimethyl
ammonium chloride; di(hydrogenated tallow) dimethyl
ammonium methyl sulfate; dihexadecyl diethyl ammonium
chloride; dihexadecyl dimethyl ammonium bromide; ditallow
dipropyl ammonium bromide; di(coconutalkyl)dimethyl
ammonium chloride, 1-methyl-1-[(tallowylamido-)ethyl]-2-
tallowyl-4,5-dihydroimidazolinium methyl sulfate; and
1-methyl-1-[(palmitoylamido) ethyl]-2-octadecyl-4,5-
dihydroimidazolinium chloride.
10. The composition in accordance with claim 8
wherein the fatty ester is selected from the group
consisting of: stearyl acetate; palmityl dilactate;
cocoyl isobutyrate; oleyl maleate; oleyl dimaleate;
26

tallowyl propionate; xylitol monopalmitate; penta-
erythritol monostearate; sucrose monostearate; glycerol
monostearate; ethylene glycol monostearate; sorbitan
monostearate; sorbitan palmitate; sorbitan monolaurate;
sorbitan monomyristate; sorbitan monobehenate; sorbitan
monoleate; sorbitan dilaurate; sorbitan distearate;
sorbitan dibehenate and sorbitan dioleate.
11. The composition in accordance with claim 8,
wherein the ethers of fatty alcohols are selected from the
group consisting of: batyl alcohol; behenyl ethylene-
glycolmono ether; octadecyl vinyl ether; cocoyl sorbityl
mono-ether; tallowyl diethylenglycol ether; palmityloxy-
propyloxypropanol; and arachidylpentaerythritol mono-ether.
12. The composition in accordance with claim 8
wherein the compound having the formula R10-X-R11 is
selected from the group consisting of: N-stearyl
methacrylamide; stearyl vinyl sulfide; N-palmityl-2-hydroxy
-ethylamide and N-tallow-3-hydroxypropylamide.
13. The composition in accordance with claim 7
wherein the fabric-substantive agent represents from about
30% to about 45% by weight, the fabric-softening component
selected from (a) and (b) from about 15% to about 25% by
weight and the fabric softening component selected from
(c), (d) and (e) from about 30% to about 55% by weight, the
amounts of the components being expressed by reference to
their sum.
14. The composition in accordance with claim 7
wherein the weight ratio of the fabric-softening component
selected from (a) and (b) to the fabric-softening component
selected from (c), (d) and (e) is equal to or smaller than
one.

15. The composition in accordance with claim 14
wherein the weight ratio of the fabric-softening component
selected from (a) and (b) to the fabric-softening component
selected from (c), (d) and (e) is equal to or smaller than
0.7.
28

Description

1~ 9
CONCENTRATED LIQUID FABRIC SOFTENER_COMPOSITION
This invention pertains to concentrated liquid fabric
softener compositions comprising a fabric substantive
agent in conjunctlon with a fabric softening component.
The fabric substantive agent is selected from polyamides,
alkylpyridinium salts and mixtures thereof. The fabric
softening component can be represented by quaternary
; ammonium salts, alkylimidazolinium salts, fatty esters,
ethers of fatty alcohols, fatty compounds which are
interrupted by a sulfur or a nitrogen atom, and mixtures
thereof. In preferred composition herein, the fabric
softening component is represented by a mixture of a
quaternary ammonium salt and an additional fabric
softening component selected from fatty esters, ethers of
fatty alcohols and fatty compounds containing a long alkyl
chain which are interrupted by a sulfur or nitrogen atom.
The concentrated liquid softeners of this invention,
in addition to easy pourability and water dispersability,
provide a series of important advantages inclusive of :
consumer convenience in transport, storage and usage
flexibility inasmuch as housewives are not any longer
limited in selecting "their" degree of softness by the
capacity of the fabric softener dispenser in automatic
washing machines. Another convenience aspect relates to
the possibility now offered to the consumer to either
utilize a concentrated product as such or to utilize it in
a conventional concentration after predilution.
Although it was well recognized that concentrated
fabric softener compositions could provide convenience and
utilization facilities to housewives, as of yet no
technical solutions could be made available to overcome
... , 1- ~,

1~61~g
known deficiencies, especially, pourability and water
dispersability, inherent to conventional products
containing more than about lO to lZ% active materials.
Attempts have been undertaken to solve these problems
through the use of electrolytes, inclusive of calcium
chloride in e.g. levels up to 2000 ppm. However, such
remedies have not provided a satisfactory solution to the
problems inasmuch as all that can be achieved is to
possibly incorporate a few percent more actives into
conventional liquid fabric softeners. However, the prior
art does not provide a solution to formulate a
commercially viable liquid rinse-softener product
containing active ingredient levels as claimed herein, or ~.
more broadly above about 15~, which do not have the
physical appearance and use shortcomings set forth above~ ~ -
It is a main object of this invention to provide
concentrated fabric softener compositions having
pourability and water-dispersability properties which are
substantially comparable to liquid softeners having
conventional active concentration ranges i.e. from about 3
to about 10% by weight.
It is a further object of this invention to provide a
liquid concentrated softener composition the physical
aspects of which resemble conventional low-active
softeners and which is not subject to any phase-stability
or other deficiencies which can develop during prolonged
storage.
The above and other objects of this invention can now
be obtained through the combined use of a fabric-
substantive agent and a fabric-softening component in
defined ranges as can be seen from the following
-- 2 --

1~-. 61~9
description of the invention.
SUM~IARY OF THE INVENTION
It has now been discovered that concentrated liquid
fabric softeners can be prepared which are capable of
providing a series of convenience, usage and, generally,
economical advantages.
The concentrated compositions herein comprise : from
about 25% to about 55~ by weight of an active system
containing a fabric-substantive agent and-a
fabric-softening component, the fabric-substantive agent
being selected from the group of :
(1) a compound having the formula
~ _ A( )
Rl Rl m
wherein R is selected from a alkyl or alkenyl group
having from 10 to 24 carbon atoms in the alk(en)yl
chain, and R-O- (CH2)nl-; the Rl
be the same or different each represent hydrogen, .
-(C2H4O)pH~ ~(C3H6O)qHr ~(C2H4O)p,(C3H6O)q,H,
a Cl 3 alkyl group or the group -(CH2)n -N (R ' ) 2'
wherein R' is selected from hydrogen,
- (C2H40)pH,- (C3H60)qH~ (C2H4())p, (C3E60)qlH~
and a Cl 3 alkyl group, where n, nl and n2
each represent an integer from 2 to 6, m is an
integer from 1 to 5, each p, q and (p'+q') may be
0 or a number such that (p+q+p'+q') does not
exceed 25, and, if in the salt or partial salt
form, A( ) represents one or more anions having
total charge balancing that of the nitrogen
atoms(s);
- 3 -

6~C~9
(2) an alkylpyridinium salt wherein the alkyl chain
has from about 10 to 24 carbon atoms; and
(3) mixtures thereof;
with the proviso that the fabric-substantive agent has a
water-solubility of more than about 5% by weight at pH 2.5
and 20C, the fabric softening component being selected
from the group of
(a) a quaternary ammonium salt having the formula
r~2 \ \ R5 ~ X(-~
wherein R2 and R3 represent hydrocarbyl groups
having from 12 to 24 carbon atoms. R4 and R5
represent hydrocarbyl groups having from 1 to 4
carbon atoms, and X is an anion;
(b) an alkylimidazolinium salt having the formula
H 2 IH 2
C C O
N ~ --C H ---N C- R A
R6 Rg
: wherein R6 is a Cl_4 alkyl group, Rg is
hydrogen or a Cl 4 alkyl group, R8 is a
: C8 25 alkyl group; and R7 is a Cg 25 alkyl
group; and A ~ is an anion;
(c) a fatty ester of mono- or polyhydric alcohols
having from 1 to about 24 carbon atoms in the
hydrocarbon chain, and mono- or polycarboxylic
acids having from 1 to about 24 carbon atoms in
the hydrocarbon chain with the provisos that the
total number of carbon atoms in the ester is equal
- 4 -

11~61~9
to OL greater than 16 and that at least one of the
hydrocarbon radicals in the ester has 12 or more
carbon atoms;
(d) ethers of fatty alcohols having from 10 to 24
carbon atoms in the alkyl chain and mono- or
polyalcohols having from 2 to 8 carbon atoms,
whereby the total number of carbon atoms in the
ether is equal to or greater than 16;
(e) compounds of the formula Rlo ~ X Rll
Rlo has from about 12 to 24 carbon atoms and
Rll from 1 to 6 carbon atoms in the alkyl chaln
which can be interrupted by not more than one
oxygen link, and X stands for sulfur,
-C-HN-;or -NH-C-;and
O O
(f) mixtures thereof,
whereby the weight of the fabric-substantive agent to the
fabric-softening component is in the range from about 6:1
to about 1:4; and a liquid carrier.
The preferred fabric-substantive agent herein can be
represented by alkoxylated diamines. Preferred
compositions contain a ternary active system comprising
the polyamines in combination with a mixture of two fabric
softening components namely a first cationic softening
component selected from the quaternary ammonium salt and
the alkylimidazolinium salt and an additional nonionic
softening component selected from fatty esters, ethers of
fatty alcohols and fatty compounds containing a long-alkyl
chain and a non-terminal amide group. In such preferred
compositions, the cationic softening component represents
less than half of the total mixture of the cationic
- 5
. .

softening component and the nonionic softening component.
DETAILED DESCRIPTION OF THE INVENTION
The concentrated liquid softener composition of this
invention comprises a fabric-substantive agent and a
fabric softener component. The fabric-substantive agent
can be represented by polyamines, alkylpyridinium salts
and mixtures thereof. The fabric-softening component can
be represented by quaternary ammonium salts, alkyl-
imidazolinium salts, a series of nonionic softening
components, and mixtures thereof. The`individual
ingredients are described in more detail hereinafter.
Unless indicated to the contrary, the "~" indications
stand for percent by weight.
A first essential component herein is a fabric-
substantive agent selected from the group of specific
polyamines, alkylpyridinium salts and mixtures thereof.
The polyamine component has the formula :
R ~ E(C~2)n N ~3~ R
Rl Rl m
wherein R is selected from an alkyl or alkenyl group having
from 10 to 24, preferably from 16 to 20 carbon atoms in the
alk(en)yl chain, and R-O-(CH2)n -; the Rlls which
may be the same or different each represent hydrogen,
-(C2H4O)pH, ~(C3H6O)qHr ~(C2H4O)p,(C3H6O)q,H,
a Cl 3 alkyl group or the group -(CH2)n -N(R') 2'
wherein R' is selected from hydrogen, -(C2H4O)pH,
~(C3H6O)qH, ~(C2H4O)p,(C3H6O)q,H and a Cl 3 alkyl group,
where n, nl and n2 each represent an integer from 2 to
6, preferably 2 or 3, m is an integer from 1 to 5,
- 6 -
.

~1~6~ 9
preferably 1 or 2, each p, q, and (p' + q') may be 0 or a
number such that (p + q + p' + q') does not exceed 25.
Preferably, each p,q and (p' ~ q') are 1 or 2. If in the
salt or partial salt form A( ) represents one or more
anions having total charge balancing that of the nitrogen
atom(s).
Preferred fabric-substantive polyamines contain not
more than one -(C2H4OH), -(C3H6OH), or
-(C2H4O)(C3H6O)H group attached to each nitrogen
atom, except that up to two of these monomeric groups (in
this context, the mixed oxyethylene/oxypropylene radical
containing 1 mole of each of the monomers is equally
defined as a monomer), can be attached to a terminal
nitrogen atom which is not substituted by an alkyl group
having from 10 to 24 carbon atoms.
Polyamine species suitable for use herein include :
N-tallowyl,N,N',N'-tris(2-hydroxyethyl)1,3-propanediamine
di-hydrochloride;
N-soybean alkyl-1,3-propane diammonium sulfate;
N-stearyl-N,N'-di(2-hydroxyethyl)-N'-(3-hydroxypropyl)-1~3-
propanediamine dihydrofluoride;
N-cocoyl N,N,N',N',N'-pentamethyl-1,3-propane diammonium
dichloride or dimethosulfate;
N-oleyl N,N',N'-tris(3-hydroxypropyl)-1,3-propanediamine
dihydrofluoride;
N-stearyl N,N',N'-tris(2-hydroxyethyl) N,N'-dimethyl-1,3-
propanediammonium dimethylsulfate;
N-palmityl N,N',N'-tris(3-hydroxypropyl)-1,3~propanediamine
; dihydrobromide;
N-(stearyloxypropyl) N,N',N'-tris(3-hydroxypropyl)1,3-
propanediammonium diacetate;

N-tallowyl N-(3-aminopropyl)1,3-propanediamine
trihydrochloride;
N-oleyl N-[N",N" bis(2-hydroxyethyl)3-aminopropyl]N',N'-
bis(2-hydroxyethyl)1,3 diaminopropane trihydrofluoride.
It is understood that the polyamines can also be
represented by components comprising a heterocyclic moiety
resulting from internal cyclization of the polyamines
having the general formula indicated above. The
cycli~ation can be produced in reacting the polyamines
with formic acid followed by thermal dehydration. Typical
examples of suitable polyamines containing such a hetero-
cyclic moiety are :
l-[N-hydrogenated tallowylaminopropyl]-pentahydropyridinium
dihydrochloride;
l-[N-stearylaminopropyl]-5-(hydroxyethyl)-tetrahydro-
pyridinium sulfate.
Preferred species frequently contain an ethylene oxide
or propylene oxide radical condensed on one or more of the
nitrogen atoms of the polyamine. The most preferred
species contain one ethylene oxide or one propylene oxide
group directly condensed onto each nitrogen atom.
A( ) may represent a halide or any appropriate
acidic radical such as a di-acetate, or higher saturated
or unsaturated acyl groups up to C22, and more in
general all nitrogen charge balancing anions which are
known to be suitable for use in these compositions.
Preferred nitrogen charge balancing anions can be
represented by halides, Cl_22 alkyl, Cl-C16 alkylaryl,
arylsulf(on)ates, arylcarboxylates and Cl-C12
alkylcarboxylates. Examples of the preferred charge
balancing anions include : fluoride, bromide, chloride,
~ - 8 -

~61ai9
..
methyl sulfate, toluene-, xylene-, cumene-, and benzene-
sulfonate, dodecylbenzenesulfonate, benzoate,
parahydroxybenzoate, acetate, propionate and laurate.
The fabric substantive agent herein can also be
represented by alkyl pyridinium salts having the following
formula
+ ~ ~ A( )
wherein R12 is a C -C , preferably C
or C18 alkyl radical, and A( ) is a suitable
anion as defined hereinbefore, preferably a
halide, especially chloride and bromide.
Individual species of the fabric-substantive agent can
be used as well as mixtures thereof. For example, a
combination of differently substituted mixtures of
polyamines can be used or a mixture of polyamine(s) and
alkylpyridinium salts.
Suitable fabric-substantive agents herein are
additionally characterized by a water-solubility or more
than about 5% at pH 2.5 and 20C.
A second essential ingredient in the compositions of
this invention is a fabric-softening component selected
from the group of : quaternary ammonium salts; ::
alkylimidazolinium salts; fatty esters; fatty ethers;
fatty compounds containing a sulfur or nitrogen linking
atom and mixtures thereof.
The quaternary ammonium salt has the formula
¦~3 51 X(~)
,.~
':s'' ~

11~6~9
wherein R2 and R3 represent hydrocarbyl groups having
from 12 to 24, preferably from 16 to 22 carbon atoms, R4
and R5 represent hydrocarbyl groups having from l to 4
carbon atoms, and X is an anion, preferably selected from
halide and methylsulfate.
Representative examples of quaternary ammonium salts
herein include ditallow dimethyl ammonium chloride;
ditallow dimethyl ammonium methyl sulfate; dihexadecyl
dimethyl ammonium chloride; di(hydrogenated tallow)
dimethyl ammonium chloride; dioctadecyl dimethyl ammonium
chloride; dieicosyl dimethyl ammonium chloride; didocosyl
dimethyl ammonium chloride; di(hydrogenated tallow)
dimethyl ammonium methyl sulfate; dihexadecyl diethyl
ammonium chloride; dihexadecyl dimethyl ammonium bromide;
ditallow dipropyl ammonium bromide; di(coconutalkyl)-
dimethyl ammonium chloride. Ditallow dimethyl ammonium
- chloride, di(hydrogenated tallow-alkyl) dimethyl ammonium
chloride and di(coconut-alkyl) dimethyl ammonium chloridè
are preferred.
The alkylimidazolinium salts herein have the formula
Hl2 H12
C C O
N ~ C H N C -R -.
I R6 Rg
R8
wherein R6 is an alkyl containing from l to 4,
preferably l or 2 carbon atoms, R7 is an alkyl
containing from 9 to 25 carbon atoms, R8 is an alkyl
containing from 8 to 25 carbon atoms, and Rg is hydrogen
or an alkyl containing from l to 4 carbon atoms.
-- 10 --

361~9
Preferred imidazolinium salts include l-methyl-l-
[(tallowylamido-)ethyl]-2-tallowyl-4,5-dihydroimidazolinium
methyl sulfate -- commercially available under the trade
mark VARISOFT 475, from ASHLAND CHEMICAL Company -- and
l-methyl-l-[~palmitoylamido)ethyl]-2-octadecyl-4,5-
dihydroimidazolinium chloride. Also suitable herein are
the imidazolinium fabric softening components of US Patent
4,127,489 issued November 28, 1978 to Pracht and Nirschl.
A is an anion having the meaning given above,
preferably a halide or a methosulfate.
Suitable fatty esters herein are derived from mono- or
polyhydric alcohols having from 1 to about 24 carbon atoms
in the hydrocarbon chain, and mono- or polycarboxylic
acids having from 1 to about 24 carbon atoms in the
hydrocarbon chain with the provisos that the total number
of carbon atoms in the ester is equal to or greater than
16 and that at least one of the hydrocarbon radicals in
the ester has 12 or more carbon atoms.
The fatty acid portion of the fatty ester can be
obtained from mono- or polycarboxylic acids having from 1
to about 24 carbon atoms in the hydrocarbon chain.
Suitable examples of monocarboxylic fatty acids include
behenic acid, stearic acid, oleic acid, palmitic acid,
myristic acid, lauric acid, acetic acid, propionic acid,
butyric acid, isobutyric acid, valeric acid, lactic acid,
glycolic acid and ~,~'-dihydroxyisobutyric acid. Examples
of suitable polycarboxylic acids include : n-butyl-malonic
acid, isocitric acid, citric acid, maleic acid, malic acid
and succinic acid.
The fatty alcohol radical in the fatty ester can be
represented by mono- or polyhydric alcohols having from 1
r~ ~ 11 --

~1~'61(~9
to 24 carbon atoms in the hydrocarbon chain. Examples of
suitable fatty alcohols include : behenyl, arachidyl,
cocoyl, oleyl and lauryl alcohol, ethylene glycol,
glycerol, ethanol, isopropanol, vinyl alcohol, diglycerol,
xylitol, sucrose, erythritol, pentaerythritol, sorbitol or
sorbitan.
Preferred fatty esters herein are ethylene glycol,
glycerol and sorbitan esters wherein the fatty acid
portion of the ester normally comprises a species selected
from behenic acid, stearic acid, oleic acid, palmitic acid
or myristic acid.
Sorbitol, prepared by catalytic hydrogenation of
glucose, can be dehydrated in well-known fashion to form
mixture of 1,4 and 1,5-sorbitol anhydrides and small
amounts of isosorbides. (See Brown, U.S. Patent
2,322,821, issued June 29, 1943). This mixture of
sorbitol anhydrides is collectively referred to as
sorbitan. The sorbitan mixture will also contain some
free, uncyclized sorbitol.
Sorbitan esters useful herein can be prepared by
esterifying the "sorbitan" mixture with a fatty acyl group
in standard fashion, e.g., by reaction with a fatty acid
halide or fatty acid. The esterification reaction can
occur at any of the available hydroxyl groups, and various
mono-, di-, etc., esters can be prepared. In fact,
m;xtures of mono-, di-, tri-, etc., esters almost always
result from such reactions. Esterified hydroxyl groups
can, of course, be either in terminal or internal
positions within the sorbitan molecule.
It is also to be recognized that the sorbitan esters
employed herein can contain up to about 15~ by weight of
.
i

~1~61~9
esters of the C20-C26, and higher, fatty acids, as
well as minor amounts of C8, and lower, fatty esters.
The presence or absence of such contaminants is of no
consequence in the present invention.
The glycerol esters are also highly preferred. These
are the mono-, di- or tri-esters of glycerol and the fatty
acids as defined above.
Specific examples of fatty alcohol esters for use
herein include : stearyl acetate, palmityl di-lactate,
cocoyl isobutyrate, oleyl maleate, oleyl dimaleate, and
tallowyl propionate. Fatty acid esters useful in the
present invention include : xylitol monopalmitate,
pentaerythritol monostearate, sucrose monostearate,
glycerol monostearate, ethylene glycol monostearate and
sorbitan esters. Suitable sorbitan esters include
sorbitan monostearate, sorbitan palmitate, sorbitan
monolaurate, sorbitan monomyristate, sorbitan
monobehenate, sorbitan monooleate, sorbitan dilaurate,
sorbitan distearate, sorbitan dibehenate, sorbitan
dioleate, and also mixed tallowalkyl sorbitan mono- and
di-esters. Glycerol esters are equally highly preferred
in the compostion herein. These are the mono-, di-, or
tri-esters of glycerol and the fatty acids of the class
described above. Glycerol monostearate, glycerol
monooleate, glycerol monopalmitate, glycerol monobehenate,
and glycerol distearate are specific examples of these
preferred glycerol esters.
The fatty esters used herein contain a number of
carbon atoms equal to or greater than 16; normally, the
fatty esters contain at least one alkyl radical having 12
or more carbon atoms.
- 13 -

11~E6~D9
The ethers of fatty alcohol have from lO to 24,
preferably from 16 to 22 carbon atoms, in the fatty
alcohol group and from 2 to about 8 carbon atoms in the
etherifying moiety. Suitable fatty alcohols are of
natural or synthetic origin and include behenyl,
arachidyl, cocoyl, oleyl, lauryl, myristyl and palmityl
alcohol. The etherifying moiety can be represented mono-
or polyalcohols and by alkylene oxides having preferably a
degree of polymerization of not more than 2. Examples of
suitable species include : ethylene glycol, glycerol,
ethanol, isopropanol, vinyl alcohol, diethyleneglycol,
di(propylene oxide), sorbitol, ethoxypropylene oxide and
pentaerythritol.
The total number of carbon atoms in the ether is equal
to or greater than 16.
Specific examples of fatty alcohol mono-ethers are : -
batyl alcohol (stearyl glycerol mono~ether), behenyl
ethyleneglycol mono-ether, octadecyl vinyl ether, cocoyl
sorbitol mono-ether, tallowyl diethyleneglycol ether,
palmityloxypropyloxypropanol, and arachidylpentaerythritol
monoether.
The fabric softening component can also be represented
by a compound having the formula : Rlo - X - Rll
wherein Rlo has from about 12 to 24, preferably from 16
to 22 carbon atoms and Rl~ from l to about 6 carbon
atoms in the alkyl chain which can be interrupted by not
more than one oxygen link and X stands for sulfur,
ll
-NH.C-, and -I-NH-. Suitable examples of this compound
include : N-stearyl methacrylamide, stearyl vinyl sulfide,
~ - 14 -

11~6~
N-palmityl-2-hydroxyethylamide, and N~tallo~yl-3-
hydroxypropylamide.
The liquid fabric softener compositions of this
invention contain from about 25% to about 55% of an active
system comprising the fabric substantive agent and the
fabric softening component, described in more detail
hereinbefore, in a weight ratio of about 6:1 to 1:4. The
fabric substantive agent represents from about 25~ to
about 85% and the fabric softening component from about
15% to about 75%, the amounts being expressed by reference
to the sum of fabric substantive agent and fabric
softening component. In a preferred aspect of this
invention, the fabric substantive agent represents from
about 50% to about 85%, preferably from 65~ to 80~ and the
fabric softening component selected from the quaternary
ammonium salt and the alkyl imidazolinium salt --
hereinafter termed cationic softening component --
represents from 15~ to 50%, preferably from 35% to 20%.
In another aspect of this invention, the fabric
substantive agent represents from about 35% to about 65%
and the fabric so:Etening component selected from the fatty
esters, the ethers of fatty alcohols and fatty compounds
containing sulfur or nitrogen linking atoms -- hereinafter
termed nonionic softening component -- represents from 35%
to 65%.
In a preferred execution, the fabric softener
composition herein is comprised of a ternary active system
namely : the fabric substantive agent and a binary fabric
softening component system containing a cationic softening
component (thus selected from a quaternary ammonium salt
and an alkyl imidazolinium salt) and a nonionic softening
- 15 -

11(~61C~9
component (thus selected from fatty esters, fatty ethers,
and fatty compounds containing a sulfur or nitrogen
linking atom)~ This preferred ternary active mixture
contains from about 25% to about 65%, more preferably from
30% to 45% of the fabric substantive agent, from about 8
to about 35~, more preferably from 15% to 25% of the
cationic softening component, and from about 15~ to about
60%, more preferably from 30~ to 55% of the nonionic
softening component. In the preferred ternary executions,
the weight ratio of the cationic softening component to
the nonionic softening component is equal to or smaller
than 1 (Sl), preferably SO,7.
In addition to the above essential components, the
compositions herein may contain other textile treatment or
conditioning agent`s. Such agents include silicones, as
for example, described in German patent application
DOS 26 31 419 published February 3, 1977.
The optional silicone component can be used in an
amount of from about 0.1~ to about 4%, preferably from
0.3% to 3~ of the softener composition. In other
preferred executions of this invention, the weight ratio
of the sum of fabric softening component and silicon to
total fabric substantive agent is in the range from 2:1 to
1:3.
The compositions herein can contain optional
ingredients which are known to be suitable for use in
textile softeners at usual levels for their known
function. Such adjuvants include emulsifiers, perfumes,
preservatives, germicides, viscosity modif.iers, colorants,
dyes, fungicides, stabilizers, brighteners, and
opacifiers. These adjuvants, if used, are normally added
- 16 -
:,

11~61~
at their conventional low levels (e.g., from about 0.1% to
5% by weight).
The polyamine fabric-substantive agent herein delivers
the claimed advantages in either fully neutralized or only
partly protonated form. The compositions of this
invention have normally a pH below about 7.5, preferably
in the range from 2.5 to 6Ø
The compositions can normally be prepared by mixing
the ingredients together in water, heating to a
temperature of about 60C and agitating for 5-30 minutes.
The ternary compositions containing a cationic and a
nonionic softening component are preferably prepared in
first melting the nonionic softening component followed by
dispersing under stirring the fabric substantive agent and
the cationic softening component in the molten nonionic
softening component. The active mix is then dispersed in
the aqueous seat, containing if needed a pH regulator.
Normally, at 60C, the subject softening agent exist
in liquid form and therefore form true emulsions with an
aqueous continuous phase. on cooling, the disperse phase
may wholly or partially solidify so that the final
composition exists as a dispersion which is not a true
liquid/liquid emulsion. It will be understood that the
term "dispersion" means liquid/liquid phase or
solid/liquid phase dispersions and emulsions.
The following experimental evidence serves to
illustrate the invention and to facilitate its
understanding.
EXAMPLE I
A concentrated liquid fabric softener was prepared
having the composition listed hereinafter. The glycerol
- 17 -

llG6~C~9
monostearate was molten at 65C. The ditallowyldimethyl-
ammoniumchloride and the N-tallowyl-N,N',N'-tri(2-
hydroxyethyl)-1,3 propane diamine (unneutralized) were
dispersed, under stirring, in the molten glycerolmono-
stearate to thus form the (molten) active material
premix. The (active material) premix was thereafter
dispersed under vigorous stirring in a waterseat having a
temperature of about 60C. Prior to adding the premix,
hydrocholoric acid and minor ingredients were added to the
waterseat to adjust the pH of the liquid softener
composition to 4.5 (measured at 20C).
INGREDIENTSPARTS BY WEIGHT
N-tallowyl-N,N',N'-tri(2-hydroxyethyl)-
1,3-propanediamine dihydrochloride 12
Ditallowyldimethylammoniumchloride 4
Glycerolmonostearate 16
Water and minor ingredientsbalance to 100
pH of composition as is at 22C:5
The concentrated composition of this invention was
easily pourable at ambient temperature after preparation
and after a prolonged storage.
This composition showed excellent phase stability and
homogeneity after a 2 weeks storage.
This composition also showed excellent fabric rinse-
softener properties either on adding to the rinse in its
concentrated form thereby reducing the quantity to be
added to thus take into account the higher level of
actives, or after predilution to the usual liquid rinse
softener concentration (5% to 8%).
- 18 -
~,.Y

11~6~g
Substantially comparable fabric-softener performance
can be obtained from the composition of example I wherein
N-tallowyl-N,N',N'-tri(2-hydroxyethyl)-1,3 propanediamine
is replaced with a substantially equivalent amount of a
polyamine selected from the group of :
N-soybean alkyl-1,3-propane diammonium sulfate;
N-stearyl-N,N'-di(2-hydroxyethyl)-N'-(3-hydroxypropyl)-1,3-
propanediamine dihydrofluoride;
N-cocoyl N,N,N',N',N'-pentamethyl-1,3-propane diammonium
10 dichloride or dimethosulfate;
N-oleyl N,N',N'-tris(3-hydroxypropyl)-1,3-propanediamine
dihydrofluoride;
N-stearyl N,N',N'-tris(2-hydroxyethyl) N,N'-dimethyl-1,3-
propanediammonium dimethylsulfate;
N-palmityl N,N',N'-tris(3-hydroxyproply)-1,3-propanediamine
dihydrobromide;
N-(stearyloxypropyl) N,N',N'-tris(3-hydroxypropyl)1,3-
propanediammonium diacetate;
N-tallowyl N-(3-aminopropyl)1,3-propanediamine
20 trihydrochloride;
N-oleyl N-[N",N" bis(2-hydroxyethyl)3-aminopropyl]N',N'-
bis(2-hydroxyethyl)1,3 diaminopropane trihydrofluoride;
1-[N-hydrogenated tallowylaminopropyl]-pentahydropyridinium
dihydrochloride; and
l-[N-stearylaminopropyl]-5-(hydroxyethyl)- stetrahydropyridinium sulfate.
-- 19 --
.~ .
'
'' ' '~' ' . ` . .

llG61~9
A series of concentrated liquid fabric softeners have
the compositions given hereinafter are prepared in a
conventional manner :
INGREDIENTS PARTS BY WEIGHT
Examples: II III IV V VI VII VIII
N-oleyl-N,N',N'-tri(3-
hydroxypropyl)-1,3-propane-
diamine dihydrofluoride 8 20
N-tallowyl-N,N',N'-tri(2-
10 hydroxyethyl)-1,3-propane-
diamine dihydrochloride 36 16
N-soybean alkyl-1,3-propane-
diammonium sulfate 22
N-cocoyl-N,N,N',N',N'-penta-
methyl-1,3-propanediammonium
dimethonsulfate 10 12
Ditallowyldimethylammonium
chloride 6 10 6 8 5
Glycerol monostearate12 12 4 14
20 Stearyl acetate 8
Stearylglyceryl mono-ether 12
N-stearyl methacrylamide 18
Water and minor ingredients balance to 1l )0
The compositions of examples II through VIII show
excellent phase stability, homogeneity, pourability and
dispersability after a prolonged storage.
Substantially comparably performing fabric-softening
compositions result from the compositions of examples II,
VI and VIII wherein the glycerol monostearate is
substituted by an equivalent amount of a nonionic
softening component selected from the group of : xylitol
monopalmitate, pentaerythritol monostearate, sucrose
monostearate, batyl alcohol, ethyleneglycol monoether,
octadecylvinylether, cocoylsorbitolmonoether, tallowyl-
diethyleneglycol ether,.palmityloxypropyloxypropanol; and
arachidylpentaerythritol monoether.
~ - 20 -

~61(~9
~ series of additional liquid fabric softeners in
accordance with the invention herein are prepared thereby
using the sequence of processing steps and manufacturing
conditions set forth in example I above.
Examples: IX X XI XII XIII XIV XV
N-hydrogenated tallowyl
N,N',N'-tri(2-hydroxyethyl)-
1,3-propanediamine
dihydrochloride 16 _ _ 6 _ 16 18
Glycerol monostearate 1212 12 _ _ _ 14
Stearyl glyceryl monoether _ _ _ 14 _ 18
N-tallowyl N-(3-amino-
propyl)-1,3-propanediamine
trihydrochloride _ 18 _ _ 22 _ _
Polyram L 200 ~ dihydro-
bromide _ _ 16 _ _ _
Di-hydrogenated tallowyl
dimethyl ammonium chloride _ _ 4 4 _ _ _
N-(stearyloxypropyl)N,N',-
N'-tri(3-hydroxypropyl)1,3-
propanediammonium diacetate _ _ _ 12 _ _ _
l-methyl l-(tallowylamido)~
ethyl-2-tallowyl 4,5-dihydro-
imidazolinium methosulfate _ _ _ _ 6 _ 8
Water and minor ingredients Balance to 100- !
(1) Polyram L 200(~)has the chemical formula :
lH2 12
H / C
C18H37 ~ N (CH2)3 \ / CH2 ;
IN
H2 H
it is sold by Pierrefitte-Auby.
i~