Dryer sheet fabric conditioner containing compatible silicones

Fabric conditioning compositions for coating a flexible substrate for subsequent use in a mechanical tumble dryer are disclosed. The compositions incorporate compatible organosilicones which form mutually stable mixtures with common fabric softening agents.

BACKGROUND OF THE INVENTION 
1. Field Of The Invention 
The instant invention relates to application of adjuvants to fabrics in 
tumble-dryer automatic dryers. More particularly, it relates to an article 
in the form of a flexible substrate carrying a fabric conditioning 
composition. 
2. Related Art 
Silicones have been applied to fabrics during manufacture of fabrics or 
during the make up of articles of clothing using processes such as padding 
or spraying. With respect to application of silicones to fabrics during a 
laundry process, Great Britain Patent Application 1,549,180; Burmeister et 
al., U.S. Pat. No. 4,818,242; Konig et al., U.S. Pat. No. 4,724,089; Konig 
et al., U.S. Pat. No. 4,806,255; Dekker et al., U.S. Pat. No. 4,661,267 
and Trinh et al , U.S. Pat. No. 4,661,269 describe aqueous dispersions or 
emulsions of certain silicones of limited viscosity incorporated in liquid 
rinse-cycle fabric softening compositions. The compositions disclosed in 
the art are rinse-cycle aqueous dispersions. A fabric softening 
composition containing emulsified silicone combined with conventional 
cationic softening agent is also taught by Barrat et al. in U.S. Pat. No. 
4,446,033. The compositions are taught for use during the aqueous rinse 
cycle of a laundry process. 
The application of fabric softeners to fabrics in the tumble dryer by use 
of a flexible substrate carrying the fabric softeners is known in the art. 
The advantages of dryer added fabric conditioning include a more 
convenient time of addition in the laundry process and avoidance of 
undesirable interaction of softening agents with detergents. 
Rudy et al., U.S. Pat. No. 3,972,131 discloses dryer sheets including a 
silicone oil as an ironing aid. Kasprzak et al., U.S. Pat. No. 4,767,548 
discloses the use of certain silicones in dryer sheet formulations. 
Coffindafer et al., U.S. Pat. No. 4,800,026 discloses curable amine 
functional silicones in fabric care compositions. 
In the manufacture of the dryer added fabric conditioning sheets described 
in the references mentioned above, when silicones are mixed with fabric 
softeners, the resulting mixtures are non-homogeneous and phase separation 
occurs readily. The homogeneity of such mixtures is ensured only by 
continuous vigorous agitation. An additional problem associated with the 
use of a nonhomogeneous mixture is the separation of actives at the point 
of application of the active mixture on the substrate resulting in 
unevenly impregnated sheets. 
Critically, in the compatible mixtures described herein, the compatible 
organosilicines do not separate from fabric softening agents during 
coating or drying of the dryer sheets. Thus, the present invention affords 
easier processing of dryer added fabric conditioning sheets. Additionally, 
even and uniform distribution of the actives on the dryer sheet can be 
attained, alleviating the problem of unevenly impregnated sheets. 
Accordingly, it is an object of the present invention to provide an article 
which provides for release of a fabric conditioning composition within an 
automatic laundry dryer, the composition containing a compatible mixture 
of a fabric softening component and a selected organosilicone. 
These and other objects and advantages will appear as the description 
proceeds. 
SUMMARY OF THE INVENTION 
The present invention is based, in part, on the discovery that specific 
silicones, defined herein as compatible, are capable of forming compatible 
mixtures with certain conventional fabric softening agents. 
It is important to differentiate between compatible and incompatible 
silicones and between compatible and incompatible mixtures of silicones 
and fabric softeners. Compatibility as taught herein is critical and is 
ascertained by the appearance and behavior of the mixture of silicone and 
fabric softener. When a silicone and a fabric softener are heated and 
mixed together, the resulting mixtures are either clear or cloudy. In the 
clear mixtures, the silicone and the fabric softener are mutually soluble 
and the clear mixtures are compatible. In the cloudy mixtures, the 
silicone and the fabric softener may or may not form mutually stable 
dispersions. A mutually stable dispersion is also compatible and is formed 
if a mixture of a silicone and a fabric softener does not separate into 
more than one phase on storage at elevated temperatures and if the mixture 
does form a uniform liquid or solid on cooling. Thus, the class of 
compatible mixtures as defined herein includes mutually soluble mixtures 
of a silicone and a fabric softener as well as mixtures wherein a silicone 
and a fabric softener form mutually stable dispersions. Compatibility of 
the mixture is critical and is determined by the Silicone/Softener 
Compatibility Test (SSCT) described below. 
In its broadest aspect, the objects of the invention are accomplished by an 
article comprising a flexible substrate carrying an effective amount of a 
fabric conditioning composition affixed thereto in a manner which provides 
for release of the conditioning composition within an automatic tumble 
dryer at dryer operating temperatures. 
The fabric conditioning composition employed in the present invention 
contains (A) certain fabric softening agents used singly or in admixture 
with each other and (B) an organosilicone having specific structural 
requirements and a specific %CH.sub.2 content. 
Component (A) includes conventionally used cationic and nonionic fabric 
softening agents, such as 
(i) cationic quaternary ammonium salts; 
(ii) nonionic softeners selected from the group of tertiary amines having 
at least one C.sub.8-30 alkyl chain, esters of polyhydric alcohols, fatty 
alcohols, ethoxylated fatty alcohols, alkylphenols, ethoxylated 
alkylphenols, ethoxylated fatty amines, ethoxylated monoglycerides, 
ethoxylated diglycerides, mineral oils, polyols, and mixtures thereof; 
(iii) carboxylic acids having at least 8 carbon atoms; and 
(iv) mixtures thereof. 
Component (B) includes organosilicones which are capable of forming 
compatible mixtures with the fabric softening agents of Component (A). The 
organosilicones of this invention are alkylsilicones or 
alkylaminosilicones having specific structural requirements defined in the 
detailed description that follows and having a %CH.sub.2 content of about 
25% to about 90%. 
Components (A) and (B) also must form a compatible mixture as determined by 
the Silicone/Softener Compatibility Test (SSCT). 
Each of components (A) and (B) employed in the invention provides fabric 
conditioning benefits such as softness, fluffiness, static control, 
ironing ease, and other benefits when fabrics are commingled with articles 
of the invention in a tumble dryer.

DETAILED DESCRIPTION OF THE INVENTION 
An article is disclosed for conditioning fabrics in a tumble dryer. The 
article of the invention comprises a flexible substrate which carries a 
fabric conditioning amount of a conditioning composition and is capable of 
releasing the conditioning composition at dryer operating temperatures. 
The conditioning composition in turn has a preferred melting (or 
softening) point of about 25.degree. C. to about 150.degree. C. 
The fabric conditioning composition employed in the invention is coated 
onto a dispensing means which effectively releases the fabric conditioning 
composition in a tumble dryer. Such dispensing means can be designed for 
single usage or for multiple uses. One such article comprises a sponge 
material releasably enclosing enough of the conditioning composition to 
effectively impart fabric softness during several drying cycles. This 
multi-use article can be made by filling a porous sponge with the 
composition. In use, the composition melts and leaches out through the 
pores of the sponge to soften and condition fabrics. Such a filled sponge 
can be used to treat several loads of fabrics in conventional dryers, and 
has the advantage that it can remain in the dryer after use and is not 
likely to be misplaced or lost. 
Another article comprises a cloth or paper bag releasably enclosing the 
composition and sealed with a hardened plug of the mixture. The action and 
heat of the dryer opens the bag and releases the composition to perform 
its softening. 
A highly preferred article comprises the compositions containing a softener 
and a compatible organosilicone releasably affixed to a flexible substrate 
such as a sheet of paper or woven or nonwoven cloth substrate. When such 
an article is placed in an automatic laundry dryer, the heat, moisture, 
distribution forces and tumbling action of the dryer removes the 
composition from the substrate and deposits it on the fabrics. 
The sheet conformation has several advantages. For example, effective 
amounts of the compositions for use in conventional dryers can be easily 
absorbed onto and into the sheet substrate by a simple dipping or padding 
process. Thus, the end user need not measure the amount of the composition 
necessary to obtain fabric softness and other benefits. Additionally, the 
flat configuration of the sheet provides a large surface area which 
results in efficient release and distribution of the materials onto 
fabrics by the tumbling action of the dryer. 
The substrates used in the articles can have a dense, or more preferably, 
open or porous structure. Examples of suitable materials which can be used 
as substrates herein include paper, woven cloth, and non-woven cloth. The 
term "cloth" herein means a woven or non-woven substrate for the articles 
of manufacture, as distinguished from the term "fabric" which encompasses 
the clothing fabrics being dried in an automatic dryer. 
It is known that most substances are able to absorb a liquid substance to 
some degree; however, the term "absorbent", as used herein, is intended to 
mean a substrate with an absorbent capacity (i.e., a parameter 
representing a substrate's ability to take up and retain a liquid) from 4 
to 12, preferably 5 to 7 times its weight of water. 
If the substrate is a foamed plastics material, the absorbent capacity is 
preferably in the range of 15 to 22, but some special foams can have an 
absorbent capacity in the range from 4 to 12. 
Determination of absorbent capacity values is made by using the capacity 
testing procedures described in U.S. Federal Specifications (UU-T-595b), 
modified as follows: 
1. tap water is used instead of distilled water; 
2. the specimen is immersed for 30 seconds instead of 3 minutes; 
3 draining time is 15 seconds instead of 1 minute; and 
4. the specimen is immediately weighed on a torsion balance having a pan 
with turned-up edges. 
Absorbent capacity values are then calculated in accordance with the 
formula given in said Specification. Based on this test, one-ply, dense 
bleached paper (e.g., Kraft or bond having a basis weight of about 32 
pounds per 3,000 square feet) has an absorbent capacity of 3.5 to 4; 
commercially available household one-ply towel paper has a value of 5 to 
6; and commercially available two-ply household toweling paper has a value 
of 7 to about 9.5. 
Suitable materials which can be used as a substrate in the invention herein 
include, among others, sponges, paper, and woven and non-woven cloth, all 
having the necessary absorbency requirements defined above. 
The preferred non-woven cloth substrates can generally be defined as 
adhesively bonded fibrous or filamentous products having a web or carded 
fiber structure (where the fiber strength is suitable to allow carding), 
or comprising fibrous mats in which the fibers or filaments are 
distributed haphazardly or in random array (i.e. an array of fibers in a 
carded web wherein partial orientation of the fibers is frequently 
present, as well as a completely haphazard distributional orientation), or 
substantially aligned. The fibers or filaments can be natural (e.g. wool, 
silk, jute, hemp, cotton, linen, sisal, or ramie) or synthetic (e.g. 
rayon, cellulose ester, polyvinyl derivatives, polyolefins, polyamides, or 
polyesters). 
The preferred absorbent properties are particularly easy to obtain with 
non-woven cloths and are provided merely by building up the thickness of 
the cloth, i.e., by superimposing a plurality of carded webs or mats to a 
thickness adequate to obtain the necessary absorbent properties, or by 
allowing a sufficient thickness of the fibers to deposit on the screen. 
Any diameter or denier of the fiber (generally up to about 10 denier) can 
be used, inasmuch as it is the free space between each fiber that makes 
the thickness of the cloth directly related to the absorbent capacity of 
the cloth, and which, further, makes the non-woven cloth especially 
suitable for impregnation with a composition by means of intersectional or 
capillary action. Thus, any thickness necessary to obtain the required 
absorbent capacity can be used. 
When the substrate for the composition is a non-woven cloth made from 
fibers deposited haphazardly or in random array on the screen, the 
articles exhibit excellent strength in all directions and are not prone to 
tear or separate when used in the automatic clothes dryer. 
Preferably, the non-woven cloth is water-laid or air-laid and is made from 
cellulosic fibers, particularly from regenerated cellulose or rayon. Such 
non-woven cloth can be lubricated with any standard textile lubricant. 
Preferably, the fibers are from 5mm to 50mm in length and are from 1.5 to 
5 denier. Preferably, the fibers are at least partially oriented 
haphazardly, and are adhesively bonded together with a hydrophobic or 
substantially hydrophobic binder-resin. Preferably, the cloth comprises 
about 70% fiber and 30% binder resin polymer by weight and has a basis 
weight of from about 18 to 45 g per square meter. 
In applying the fabric conditioning composition to the absorbent substrate, 
the amount impregnated into and/or coated onto the absorbent substrate is 
conveniently in the weight ratio range of from about 10:1 to 0.5:1 based 
on the ratio of total conditioning composition to dry, untreated substrate 
(fiber plus binder). Preferably, the amount of the conditioning 
composition ranges from about 5:1 to about 1:1, most preferably from about 
3:1 to 1:1, by weight of the dry, untreated substrate. 
According to one preferred embodiment of the invention, the dryer sheet 
substrate is coated by being passed over a rotogravure applicator roll. In 
its passage over this roll, the sheet is coated with a thin, uniform layer 
of molten fabric softening composition contained in a rectangular pan at a 
level of about 15 g/square yard. Passage of the substrate over a cooling 
roll then solidifies the molten softening composition to a solid. This 
type of applicator is used to obtain a uniform homogeneous coating across 
the sheet. 
Following application of the liquefied composition, the articles are held 
at room temperature until the composition substantially solidifies. The 
resulting dry articles, prepared at the composition substrate ratios set 
forth above, remain flexible; the sheet articles are suitable for 
packaging in rolls. The sheet articles can optionally be slitted or 
punched to provide a non-blocking aspect at any convenient time if desired 
during the manufacturing process. 
The fabric conditioning composition employed in the present invention 
includes certain fabric softeners which can be used singly or in admixture 
with each other. 
Fabric Softener Component 
Fabric softeners suitable for use herein are selected from the following 
classes of compounds: 
(i) Cationic quaternary ammonium salts. The counterion is methyl sulfate or 
any halide, methyl sulfate being preferred for the drier-added articles of 
the invention. Examples of cationic quaternary ammonium salts include, but 
are not limited to: 
(1) Acyclic quaternary ammonium salts having at least two C.sub.8-30, 
preferably C.sub.12-22 alkyl chains, such as: ditallowdimethyl ammonium 
methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, 
distearyldimethyl ammonium methylsulfate, dicocodimethyl ammonium 
methylsulfate and the like; 
(2) Cyclic quaternary ammonium salts of the imidazolinium type such as 
di(hydrogenated tallow)dimethyl imidazolinium methylsulfate, 
1-ethylene-bis(2-tallow-1-methyl) imidazolinium methylsulfate and the 
like; 
(3) Diamido quaternary ammonium salts such as: methyl-bis(hydrogenated 
tallow amidoethyl)-2-hydroxyethyl ammonium methyl sulfate, methyl 
bis(tallowamidoethyl)-2-hydroxypropyl ammonium methylsulfate and the like; 
(4) Biodegradable quaternary ammonium salts such as 
N,N-di(tallowoyl-oxy-ethyl)-N,N,-dimethyl ammonium methyl sulfate and 
N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate. When 
fabric conditioning compositions employ biodegradable quaternary ammonium 
salts, pH of the composition is preferably adjusted to between about 2 and 
about 5. Biodegradable quaternary ammonium salts are described, for 
example, in U.S. Pat. Nos. 4,137,180, 4,767,547 and 4,789,491 incorporated 
by reference herein. 
(ii) Tertiary fatty amines having at least one and preferably two C8 to 
C30, preferably C12 to C22 alkyl chains. Examples include hardened tallow 
amine and cyclic amines such as 1-(hydrogenated 
tallow)amidoethyl-2-(hydrogenated tallow) imidazoline. Cyclic amines which 
may be employed for the compositions herein are described in U.S. Pat. No. 
4,806,255 incorporated by reference herein. 
(iii) Carboxylic acids having 8 to 30 carbon atoms and one carboxylic group 
per molecule. The alkyl portion has 8 to 30, preferably 12 to 22 carbon 
atoms. The alkyl portion may be linear or branched, saturated or 
unsaturated, with linear saturated alkyl preferred. Stearic acid is a 
preferred fatty acid for use in the composition herein. Examples of these 
carboxylic acids are commercial grades of stearic acid and the like which 
may contain small amounts of other acids. 
(iv) Esters of polyhydric alcohols such as sorbitan esters or glycerol 
stearate. Sorbitan esters are the condensation products of sorbitol or 
iso-sorbitol with fatty acids such as stearic acid. Preferred sorbitan 
esters are monoalkyl. A common example of sorbitan ester is SPAN 60 (ICI) 
which is a mixture of sorbitan and isosorbide stearates. 
(v) Fatty alcohols, ethoxylated fatty alcohols, alkyl phenols, ethoxylated 
alkyl phenols, ethoxylated fatty amines, ethoxylated monoglycerides and 
ethoxylated diglycerides. 
(vi) Mineral oils, and polyols such as polyethylene glycol. 
These softeners are more definitively described in U.S. Pat. No. 4,134,838 
incorporated by reference herein. Preferred fabric softeners for use 
herein are acyclic quaternary ammonium salts, 
di(hydrogenated)tallowdimethyl ammonium methylsulfate is most preferred 
for dryer articles of this invention. Especially preferred are mixtures of 
di(hydrogenated)tallowdimethyl ammonium methylsulfate with fatty acids, 
particularly stearic acid. 
The amount of the fabric softening composition on the sheet is subject to 
normal coating parameters such as, for example, viscosity and melting 
point of the fabric softening component and is typically about 0.5 grams 
to about 5 grams, preferably about 1 gram to about 3.5 grams. The fabric 
softening composition employed in the present invention contains about 
0.1% to about 95% of the fabric softening component. Preferably from about 
10% to about 80% and most preferably from about 30% to about 70% of the 
fabric softening component is employed herein to obtain optimum softening 
at minimum cost. When the fabric softening component includes a quaternary 
ammonium salt, the salt is used in the amount of about 10% to about 80%, 
preferably about 30% to about 70%. 
Silicone 
The second essential ingredient of the fabric softening composition 
employed in the present invention is an organosilicone. 
Organosilicones employed in the present invention (also termed herein as 
compatible silicones) are capable of forming compatible mixtures with the 
fabric softeners listed above. 
The organosilicones employed herein have a %CH.sub.2 content of about 25% 
to about 90%. The % CH.sub.2 content is defined as 
##EQU1## 
The organosilicones included in the fabric conditioning compositions of the 
invention contain at least one unit of Formula A: 
##STR1## 
wherein m is a number from 0 to 2 and R is a mono valent hydrocarbon 
radical. The value of (3-m)/2 in Formula A means the ratio of oxygen atoms 
to silicon atoms, i.e. SiO.sub.1/2 means one oxygen is shared between two 
silicon atoms. 
R.sup.1 in Formula A is selected from the group consisting of: 
i) a hydrocarbon radical having from 6 to 45 carbon atoms, preferably from 
8 to 18 carbon atoms and which may be saturated, unsaturated, cyclic, 
acyclic, alkyl or aromatic; 
ii) a unit of Formula A1: 
##STR2## 
wherein a is a number of at least 1, preferably 3; b is a number from 0 to 
10, preferably 1; R.sup.2 
##STR3## 
R.sup.3 is a hydrocarbon radical having from 4 to 40 carbon atoms 
preferably from 8 to 18 carbon atoms and may be saturated, unsaturated, 
cyclic, acyclic, alkyl or aromatic; and R.sup.4 is hydrogen or a 
hydrocarbon radical having from 1 to 40 carbon atoms, preferably hydrogen; 
and 
iii) a unit of Formula A2 
##STR4## 
wherein R.sup.5 and R.sup.6 are independently selected from hydrogen or a 
hydrocarbon radical having from 1 to 45 carbon atoms which may be 
saturated, unsaturated, cyclic, acyclic, alkyl or aromatic and at least 
one of R.sup.5 and R.sup.6 is a hydrocarbon radical having from 6 to 45 
carbon atoms, R.sup.7 is 
##STR5## 
wherein R.sup.8 is a divalent organic radical having from 1 to 12 carbon 
atoms and may be saturated, unsaturated, cyclic, acyclic, alkyl or 
aromatic, and preferably is --CH.sub.2 CH.sub.2 CH.sub.2 --O--CH.sub.2 --. 
Thus, organosilicones employed in the present invention include 
alkylsilicones and alkylaminosilicones which satisfy the structural 
parameters described above and which have a % methylene (%CH.sub.2) 
content of about 25% to about 90%. Compatibility of the organosilicones 
herein with fabric softening agents is related to the %CH.sub.2 content of 
the organosilicones. 
The preferred range of the %CH.sub.2 content for the silicones herein is 
about 40% to about 90%, more preferably about 50% to about 85%, and most 
preferably about 50% to about 75% to increase the degree of compatibility 
of the organosilicones with various fabric softening agents. 
The organosilicones included in the compositions herein may be linear, 
branched, or partially crosslinked, preferably linear, and may range from 
fluid, liquid to viscous liquid, gum and solid. 
An example of an alkylsilicone suitable for use herein is: 
##STR6## 
An example of a suitable alkylaminosilicone containing the unit of Formula 
A1 is: 
##STR7## 
An example of an alkylaminosilicone containing the unit of Formula A2 is: 
##STR8## 
Alkylsilicones employed in this invention may be produced by reacting a 
hydrosiloxane co-polymer with a hydrocarbon having 6 to 45 carbon atoms 
and having a terminal vinyl functionality. Such reactions are described, 
for example, in Chemistry and Technology of Silicones by Walter Noll, 
Academic Press, N.Y. (1968), pages 49-51 and 219-226. Commercially 
available alkylsilicones suitable for use herein are, for example, Masil 
264, Masil 265, Masil 265 HV from Mazer International Corp. and ABIL - Wax 
9800 or ABIL - Wax 9801 from Th. Goldschmidt AG. 
Alkylaminosilicones employed in this invention may be produced by 1) 
treating silicones containing primary or secondary amine functional groups 
with epoxides such as ethylene oxide to form alkylaminosilicones having 
the unit of Formula A1, or 2) by treating epoxysilicones with primary or 
secondary amines such as dicocoamine to form alkylaminosilicones having 
the unit of Formula A2. 
The modified alkylaminosilicones of the invention having the unit of 
Formula A1 may be prepared by mixing epoxide compounds with aminosilicones 
in a pressure reactor and heating for about 24 hours, after Which the 
unreacted epoxide compound is vacuum stripped off. The amount of epoxide 
to be used is calculated based upon the number of amine functional groups 
on the alkylaminosilicone. Preferably, two epoxides are reacted for every 
primary amine and one epoxide for every secondary amine, in order to 
convert them to tertiary amines. A stoichiometric amount or up to 25% 
excess of epoxide can be used. The reaction is preferably conducted 
between 25.degree. C. and 150.degree. C., especially between 50.degree. C. 
and 100.degree. C. The pressure is preferably maintained from 50 psi to 
300 psi, particularly from 50 psi to 150 psi. Typical aminosilicone 
starting compounds would include Dow Corning Q2-8075. The art of making 
alkylaminosilicones having the unit of Formula A1 is disclosed in Examples 
1 and 2 herein and in the copending patent applications of Lin et al. 
entitled "Hydroxylhydrocarbyl Modified Aminoalkyl Silicones", Ser. No. 
449,360 filed Dec. 6, 1989. 
The modified alkylaminosilicones having the unit of Formula A2 may be 
prepared by mixing epoxysilicones, secondary amines, and a solvent such as 
isopropanol or toluene, and heating the mixture at reflux for about 24 
hours, after which the solvent is removed by distillation or vacuum 
stripping. The amount of amine to be used is calculated based upon the 
number of epoxy functional groups on the epoxysilicone. Preferably, one 
secondary amine is reacted for every epoxy functional group in order to 
convert the amine to tertiary amine. A stoichiometric amount or up to 25% 
excess of amine can be used. The reaction is preferably conducted between 
50.degree. C. and 150.degree. C., especially between 75.degree. C. and 
110.degree. C. The reaction is preferably conducted at atmospheric 
pressure, but may be conducted in a pressure reactor with the pressure 
being maintained from 50 psi to 300 psi. 
The modified alkylaminosilicones employed in this invention contain amine 
groups which may be quaternized with, for example, alkyl halide or methyl 
sulfate, or may be protonated with Lewis acid such as hydrochloric acid, 
acetic acid, citric acid, formic acid and the like. 
Alkylsilicones and alkylaminosilicones employed herein may, in addition to 
the units of Formula A, contain secondary units selected from the group 
consisting of a unit of Formula B1 and a unit of Formula B2: 
##STR9## 
wherein R.sup.11 radical having from 1 to 40 carbon atoms, preferably is 
CH.sub.3 ; R.sup.9 is a hydrocarbon radical having from 1 to 3 carbon 
atoms; R.sup.10 is oxygen or alkylene having from 1 to 8 carbon atoms, 
preferably propylene; y and z are numbers from 0 to 2; and c and d are 
numbers from 0 to 50, preferably from 2 to 15. 
Organosilicones preferred for use herein have the %CH.sub.2 of about 40% to 
about 90% and are either alkylaminosilicones having the unit of Formula A1 
or alkylsilicones. 
The weight ratio of the organosilicone to the fabric softening component in 
the fabric conditioning compositions employed herein is from about 100:2 
to about 1:100, preferably from about 2:100 to about 20:100, but must be 
such that a compatible mixture can be formed. The minimum weight ratio at 
which the compatible mixtures can be formed is determined experimentally 
as part of the Silicone/Softener Compatibility Test (SSCT) described 
herein. The amount of the organosilicone is governed by the ratio at which 
the compatible mixture can be formed. The amount of organosilicone 
employed herein generally ranges from about 0.1% to about 20%, and is 
preferably at least about 3%. 
Silicone/Softener Compatibility Test (SSCT) 
As described above, mixtures defined as compatible herein include mutually 
soluble as well as mutually stable dispersible mixtures. Compatibility of 
the fabric conditioning mixtures herein depends on the structure and the 
%CH.sub.2 content of the organosilicone and the particular fabric 
softeners employed in the mixture. SSCT provides a basis for selecting 
appropriate combinations of the fabric softening component and the 
organosilicone. 
The test may be used to determine the compatibility at a particular weight 
ratio of interest or to determine a minimum concentration of the silicone 
at which a compatible mixture of the silicone and the fabric softening 
component is formed. 
SSCT is conducted as follows: a 10 gram sample of the fabric softener or a 
combination of fabric softeners is placed into a clear glass flask 
equipped with a stirring mechanism, such as a magnetic stirrer. If either 
the fabric softener or the silicone is a solid at room temperature, it is 
melted before the test is begun with the test taking place above the 
melting point of the fabric softener or the silicone. The silicone of 
interest is slowly introduced with, conveniently, a Pasteur pipet into the 
flask, with stirring. It is estimated that the weight of one drop 
represents about 1% silicone concentration, so the silicone is mixed with 
the fabric softener 1% at a time. Thus, the lowest concentration of the 
silicone in the mixture is about 1%. 
If the resulting mixture of the fabric softening agent and the silicone 
stays clear over the entire investigated range of the silicone, this 
indicates that the components of the mixture are mutually soluble over the 
investigated concentration range and, accordingly, are compatible. Clear 
mixtures are defined herein as mixtures having about 90% transmittance 
when measured with a visible light probe (one centimeter pathlegth) 
against distilled water background using Brinkman PC800 colorimeter. 
The mixture may also become cloudy indicating that the silicone and the 
fabric softener are not mutually soluble at that weight % of the silicone. 
In this case, if the mixture became cloudy, the weight percent of the 
silicone added to produce cloudiness is calculated. This number, termed 
compatibility .alpha., then represents the weight percent of the silicone 
to produce a cloudy mixture. Cloudy samples are placed in an oven at 
100.degree. C. for at least two hours, then cooled to room temperature and 
inspected. Samples which have completely separated into distinct layers 
are incompatible and are not useful for the invention. Samples which 
maintain a stable, dispersed character are compatible and, hence, useful 
in the invention. 
It is sufficient, for practical applications, to investigate the silicone 
concentration range of up to about 30%. However, the entire range up to 
100% of the silicone concentration may be investigated if desired. When 
the entire range of the silicone concentration is to be investigated, the 
silicone is added until the mixture contains about 60% by weight of the 
silicone. Silicone addition is then stopped, and the experiment is 
repeated by adding the fabric softener to a 10 gram sample of the 
silicone. In those samples that became cloudy, the weight percent of the 
softener added to produce cloudiness is calculated and subtracted from 
100, the resulting number is termed herein compatibility .beta.. 
.alpha. compatibility reflects compatibility of the mixtures containing a 
fabric softener as a major component, whereas .beta. compatibility 
reflects compatibility of the mixtures containing a silicone as a major 
component. Minimal difference between .beta. and .alpha. (.beta.-.alpha.) 
reflects degree of compatibility of the mixture: more compatible mixtures 
have a lower number for .beta.-.alpha.. 
Preferably, the silicone and the fabric softening component are compatible 
at a silicone concentration of at least about 2%. 
Mutually soluble and clear mixtures of the silicone and the fabric 
softening component indicate the highest degree of compatibility and are 
preferred. 
Various additives may be used in combination with the compatible mixture of 
the fabric softening component and the compatible silicone. The additives 
are used in the amounts that do not substantially affect the compatibility 
of the mixture and include small amounts of incompatible silicones, such 
as predominantly linear polydialkylsiloxanes, e.g. polydimethylsiloxanes; 
soil release polymers such as block copolymers of polyethylene oxide and 
terephthalate; amphoteric surfactants; anionic soaps; and zwitterionic 
quaternary ammonium compounds. Smectite type inorganic clays improve the 
processing of the compositions and do not settle out and, hence, do not 
adversely affect the homogeneity of the compatible mixtures and may be 
used in the amounts of up to about 10%. 
Other optional ingredients include optical brighteners or fluorescent 
agents, perfumes, colorants, germicides and bactericides. 
The organosilicone and the fabric softening component which have been 
determined by the SSCT to form a compatible mixture are heated and mixed, 
and the resulting fabric conditioning mixture is coated onto a flexible 
substrate. 
The following Examples will more fully illustrate the embodiments of this 
invention. All parts, percentages and proportions referred to herein and 
in the appended claims are by weight unless otherwise indicated. 
EXAMPLE 1 
The alkylaminosilicone MD.sub.190 D*.sub.10 M, Where M=Me.sub.3 
SiO.sub.0.5, 
##STR10## 
is a condensation product of the starting aminosilicone (where A=H) and 
1,2 epoxyoctadecane. The compound was prepared by placing the starting 
aminosilicone (61.16 g), 1,2 epoxyoctadecane (38.84 g) and 2-propanol 
(60.0 g) in a reaction vessel and heating to 80.degree. C. for 24 hours. 
The reaction vessel consisted of a three neck round bottom flask 
containing a stirrer, a reflux condenser and a thermometer. The 2-propanol 
was then stripped off with a N.sub.2 sparge at 100.degree. C. as described 
in the Lin et al. applications mentioned above. 
MD190D.sup.* 10M has %CH.sub.2 equal 56.62. 
EXAMPLE 2 
A "T" structure modified alkylaminosilicone, having %CH.sub.2 equal 52.50 
is prepared according to Example 1 except that the silicone is MD.sub.10.4 
T*M.sub.2. The alkylaminosilicone is of the structure: 
##STR11## 
In the starting aminoalkylsilicone, B=H whereas in the modified 
aminoalkylsilicone, B=CH.sub.2 CHOH--(CH.sub.2).sub.9 CH.sub.3. 
In the process, 34.7 g aminoalkylsilicone, 34.4 g 1,2-epoxydodecane and 
17.4 g 2-propanol were charged to the reaction vessel following the 
procedures of Example 1. 
EXAMPLE 3 
Effect of the %CH.sub.2 content of various silicones as indicated in Table 
I on the compatibility with Adogen 442 (di-tallow dimethyl ammonium 
chloride from Sherex Corp.) was investigated by mixing the silicones with 
Adogen 442, following the SSCT procedure. 
The results that were generated are summarized in Table I. Samples 3 and 4 
were synthesized in Examples 1 and 2 respectively. 
TABLE I 
______________________________________ 
# Silicone % CH.sub.2 
Compatible 
______________________________________ 
1. DC 200.sup.1 0 no 
2. DC SSF.sup.2 0 no 
3. MD.sub.190 D*10.sup.M 
56.62 yes 
4. MD.sub.10.4 T*M.sub.2 
52.50 yes 
______________________________________ 
.sup.1 Linear polydimethylsiloxane, supplied by Dow Corning, viscosity = 
1000 cst 
.sup.2 Aminosilicone supplied by Dow Corning, amine neutral equivalent = 
2000, viscosity = 130 cst. 
The silicones of samples 3 and 4 were mutually soluble and, hence, 
compatible with Adogen 442 at silicone concentration of 5% by weight of 
the mixture. However, silicones 1 and 2, which are not within the scope of 
the present invention, were not compatible with Adogen 442 at 5% or even 
at 25% of silicone. 
EXAMPLES 4-6 
The compatibility of various fabric softening agents with various silicones 
was determined by the SSCT. The entire concentration range up to 100% of 
the silicones was investigated. Samples that remained clear over the 
entire range of silicone concentration were labeled "completely soluble." 
For samples that became cloudy stability of the dispersions was 
ascertained and .alpha. and .beta. compatibility values were determined by 
the SSCT. 
The silicones that were investigated are listed in Table II. In the 
silicone formulas of Table II M=Me.sub.3 SiO.sub.0.5, D=Me.sub.2 Si-O, 
##STR12## 
and R' is as indicated in Table II. 
TABLE II 
______________________________________ 
Code Formula R' % CH2 
______________________________________ 
A Polydimethylsiloxane 
-- 0 
(.eta. = 1000 cst) 
B MD100D*5M C.sub.8 H.sub.17 
14 
C MD100D*5M C.sub.18 H.sub.37 
28 
D MD400D*20M C.sub.18 H.sub.37 
28 
E MD100D*10M C.sub.18 H.sub.37 
43 
F MD95D*24M C.sub.12 H.sub.25 
57 
______________________________________ 
EXAMPLE 4 
In this example, mixtures of the silicones listed in Table II with mineral 
oil were investigated using the SSCT. The mineral oil used was Fisher 
Light Mineral oil. The results that were generated are summarized in Table 
III. 
TABLE III 
______________________________________ 
Compatibility with Mineral Oil 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 1 95 NO 
B 4 80 NO 
C COMPLETELY SOLUBLE 
YES 
E COMPLETELY SOLUBLE 
YES 
F COMPLETELY SOLUBLE 
YES 
______________________________________ 
As determined by the SSCT, silicones C, E and F having the structural 
requirements and %CH.sub.2 recited by the present invention form 
compatible mixtures with mineral oil. 
EXAMPLE 5 
In this example, mixtures of the silicones listed in Table II with various 
cationic quaternary fabric softening agents were investigated using the 
SSCT. 
The results that were generated are summarized in Tables IV, V and VI. 
TABLE IV 
______________________________________ 
Compatibility with Varisoft 137.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 2 97 NO 
B 2 98 NO 
C 2 96 NO 
E 7 93 YES 
F 7 90 YES 
______________________________________ 
.sup.1 Varisoft 137 = di(hydrogenated)tallow dimethyl ammonium 
methylsulfate from Sherex. 
TABLE V 
______________________________________ 
Compatibility with Varisoft 445.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 2 97 NO 
E 10 97 YES 
F -- 97 YES 
______________________________________ 
.sup.1 Varisoft 445 = di(hydrogenated)tallow imidazolinium methylsulfate 
from Sherex. 
TABLE VI 
______________________________________ 
Compatibility with Varisoft 110.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 1 98 NO 
E 5 90 YES 
F 5 90 YES 
______________________________________ 
.sup.1 Varisoft 110 = methyl bis(hydrogenated tallow amidoethyl) 
2hydroxyethyl ammonium methylsulfate from Sherex 
EXAMPLE 6 
In this example, mixtures of the silicones listed in Table II with various 
nonionic fabric softening agents were investigated using the SSCT. 
Results that were generated are summarized in Tables VII, VIII, IX and X. 
TABLE VII 
______________________________________ 
Compatibility with Neodol 45-7.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 1 99 NO 
B 1 99 NO 
D 2 99 NO 
F 5 93 YES 
______________________________________ 
.sup.1 Neodol 457 = ethoxylated fatty alcohol from Shell. 
TABLE VIII 
______________________________________ 
Compatibility with Adogen 345D.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 2 60 NO 
B COMPLETELY SOLUBLE 
YES 
D COMPLETELY SOLUBLE 
YES 
E COMPLETELY SOLUBLE 
YES 
F COMPLETELY SOLUBLE 
YES 
______________________________________ 
.sup.1 Adogen 345D = di(hydrogenated)tallow dimethyl amine from Sherex. 
TABLE IX 
______________________________________ 
Compatibility with PEG 600.sup.1 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBLE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 2 99 NO 
B 2 98 NO 
D 4 95 NO 
E 4 95 YES 
F 4 95 YES 
______________________________________ 
.sup.1 PEG 600 = Polyethylene Glycol. 
TABLE X 
______________________________________ 
Compatibility with isostearic acid 
.alpha. .beta. 
COMPAT- COMPAT- COMPATIBILE 
SILICONE IBILITY IBILITY (YES/NO) 
______________________________________ 
A 3 95 NO 
F 3 96 YES 
______________________________________ 
Examples 3-6 demonstrate that mutual compatibility between the fabric 
softening component and organosilicones may be easily determined by the 
SSCT and that the compatibility depends on the structure and %CH.sub.2 
content of the silicone as well as the particular fabric softening 
component employed in the mixture. Although silicone C was highly 
compatible (mutually soluble) with mineral oil in Example 3 and with 
Adogen 345D in Example 6, it was less compatible with Varisoft 137 of 
Example 4, i.e. a cloudy mixture was formed at 2% of silicone. However, 
silicone C was more compatible with Varisoft 137 in Example 4 than 
polydimethylsiloxane, since .beta. compatibility was lower for silicone C 
than for polydimethylsiloxane. Results in Table VIII indicate that amines 
have the highest degree compatibility with organosilicones, since 
silicone B, which has the %CH.sub.2 content of 14% and is not within the 
scope of this invention is still compatible with di(hydrogenated)tallow 
dimethyl amine. Silicones E and F, having a high %CH.sub.2 content (43% 
and 57% respectively) were the most compatible with all softeners tested. 
EXAMPLE 7 
Two fabric softening sheets, A and B were prepared as follows: 
The ingredients of a fabric conditioning composition as listed below were 
mixed in the melt. 500 g of the prepared fabric conditioning mixture was 
placed in the pan of a two-roll coating machine and coated onto a 
spun-bonded polyester non-woven material. The fabric softening articles 
thus manufactured contained about 1.6 g of solidified softening 
composition. The articles of manufacture were then placed into a tumble 
dryer machine which already contained 2.2 kg of prewashed clothing, 
including terry towelling softness monitors. The fabrics were then tumble 
dried with the fabric softening article until dry and the softening 
benefit was evaluated by a 20 member panel. 
Fabric Conditioning Formulation For Sheet A 
a) 10% of a silicone not suitable for use in the present invention 
(silicone B from Table II) 
b) 70% di(hydrogenated)tallow dimethyl ammonium methylsulfate 
c) 20% stearic acid 
Fabric Conditioning Formulation For Sheet B 
a) 7% of a silicone within the scope of this invention (silicone F from 
Table II) 
b) 70% di(hydrogenated)tallow dimethyl ammonium methylsulfate 
c) 23% stearic acid 
Observations And Results 
Sheet A--Due to the incompatible nature of the silicone, the silicone 
separated from the softening component during the coating process. The 
articles thus contained unknown amounts of the silicone. Sheet B--The 
compatible silicone of the invention and the softening component formed a 
compatible mixture which remained homogeneous during the coating process 
as it was transferred to the substrate indicating that the substrate was 
uniformly and evenly coated. 
A 20 member panel judged the towelling monitors for both sheet A and sheet 
B to have superior softness vs. towels prepared in an identical fashion 
but dried without softener. 
This invention has been described with respect to certain preferred 
embodiments and various modifications thereof will occur to persons 
skilled in the art in the light of the instant specification and are to be 
included within the spirit and purview of this application and the scope 
of the appended claims.