close

Вход

Забыли?

вход по аккаунту

?

Патент USA US2406902

код для вставки
Patented Sept. 3, 1946.
2,406,902
UNITED STATES PATENT OFFICE
2,406,902
SOAP-LIKE PREPARATIONS
Albert L. Rawlins, Grosse Pointe Woods, Mich.,
assignor to Parke, Davis & Company, Detroit,
Mich., a corporation of Michigan
No Drawing. Application November 23, 1942,
Serial No.v 466,671
(cl; 252-152)
8 Claims.
1
2
The invention relates to new and useful germi
cidal soap-like preparations where the products
are especially suitable because of their lathering
two amines are readily available commercially.
I have discovered that said salts of hexadecyl
amine and octadecyl amine, when used with a ger
micidal water-soluble high molecular quaternary
proper-ties and practical germicidal effectiveness
when actually used for cleansing the skin.
. ammonium compound which has little or none of
An object of the invention is to provide new
the’ latherlng properties mentioned above, give
and valuable lathering detergents which make
use of readily available higher alkyl amine salts
having detergent properties, but possessing little
or none of the lathering properties of ordinary
soap, by combining said salts with certain sub
stantially non-lathering quaternary ammonium
compounds which coact with said higher amine
salts to produce a rich full bodied and permanent
lather when worked up with water.
A further object of the invention is to provide
new non-irritating germicidal soap-like prepara
tions of increased germicidal and detergent ac
tion.
.
United States Patent No. 2,274,807 describes
the use as detergents of water-soluble salts of
combinations which are not only excellent lather
ing preparations suitable for toilet and like uses,
but which also retain the germicidal properties
10 of the quaternary ammonium compound. Thus,
‘the products of this invention are‘ surprisingly
effective as germicidal soap-like preparations.
The salts of hexadecyl amine and octadecyl
amine which may be used are Water-soluble, or
at least slightly water-solublaand may be min
eral acid addition salts such as a hydrohalic acid
salt, a sulfate or a phosphate or the like, and
also organic carboxylic acid addition salts where
' the acid is monobasic or polybasic, such as acetic,
propionic, buytric, and succinic acids, organic hy
droxy acids, e. g. citric, lactic and tartaric acids,
primary straight-chain alkyl amines in which the
any of the isomeric valeric acids, benzoic, salicylic
alkyl group contains 10 to 18 carbon atoms. Al
and like acids. A common characteristic of such
though these compounds are detergents in a gen
acids is that they do not give water insoluble salts
eral sense, I have found that the individual com
with hevadecyl amine or octadecylamine. Hence,
pounds of the series vary considerably in effec
the organic acid constituent is usually an acid
tiveness when used for particular detergent pur
of relatively low molecular weight.
poses. For example, most of them are highly ef
In general, any germicidal high molecular quat
fective for use on textiles, fabrics and wash goods
ernary ammonium compound may be used with
generally. On the other hand, I have found that 30 the acid addition salts of hexadecyl and octadecyl
certain important members of the series when
amines provided the quaternary compound is ap~
used alone are entirely unsatisfactory for special
preciably water-soluble. However, I have found
detergent purposes. More particularly, I have
that the best results are obtained if the germi
found that, although the salts of hexadecyl amine,
cidal high molecular quaternary ammonium com
and also octadecyl amine, are good detergents for 35 pound is at least soluble to the extent of 1 part
some purposes, such as washing clothes, they are
in 100 of water and has a surface tension of less
entirely unsuited for employment as lathering
than about 40 dynes/cm. in 1% aqueous solution
soaps for use on the skin.
'
at 25° C.
In order to be satisfactory as a substitute for
Although the amine salts and the quaternary
soap, a detergent should readily work up with 40 compounds may be used together in widely vary
ing proportions, it is usually preferable, for rea
water, for example, when rubbed between one’s
sons of economy, to use more of the cheaper
hands, to give a rich, thick-bodied lather of a
amine salts.
more or less permanent ‘nature. Because of the
increased bulk of such a lather, as compared with
The following examples illustrate how the above
the material from which it is generated, it is easy 45 mentioned objects of the invention may be at
tained.
‘
to work into the different corners and crevices of
the body and the skin and thereby effectively and
Example 1
economically produces its detergent action, I
have found that acid addition salts of hexadecyl
A quantity of hexadecyl amine is dissolved in
and octadecyl amines de?nitely fail to meet these 50 ether, absolute alcoholic hydrochloric acid added
requirements, since they only yield a‘ small
to form the hydrochloride of the amine, the mix
amount of more or less thin, transparent bubbles,
ture cooled, ?ltered and washed with ether. The
with practically no suds or lather, when worked
?ltered and washed solid product is the hydro
up with water as is commonly done with a hand
chloride of hexadecyl amine. It is only slightly
soap or toilet soap.
0n the other hand, these 55 soluble in water. It cannot be used with water
2,400,902
Bromoethylate oi N-dodee'yi benzotri
in any proportion to form a lather. It is. for"
practical purposes, totally useless as a soap for
azole
65
(c) Hexadecyl amine hydrohalide ______ __
2
toilet purposes.
1,3-dioctyl benzotriazolium bromide--- 0.5
80 g. of the hexadecyl amine hydrochloride are
mixed thoroughly with 20 g. of para-tertiary 5 (d) Octadecyl'amine lactate _________ __ 180
octyl phenoxyethoxyethyl dlmethyl benzyl am
p-Tertiary octyl phenoxyethoxyethyl
monium chloride. This quaternary ammonium
dimethyl benzyl ammonium chloride 45
(e) Mixture of hexadecyl amine propionate
(28%) and octadecyl amine propio
compound, when used alone with water in any
proportion, cannot be worked up into a lather and
is not satisfactory for use as a lathering soap
preparation. However, the mixture of the qua
ternary compound with the hydrochloride of
hexadecyl amine, prepared as described, is an
10
nate (72%) ____________________ __ 100
Cetyl trimethyl ammonium bromide___ 25
(f) Mixture of hexadecyl amine hydrochlo
ride and octadecyl amine hydrochlo
excellent product for use in the same manner as
a toilet soap or a germicidal soap. It has the 15
advantage of readily being worked up with water
ride 25% ______________________ __
75
Dodecyl dimethyl benzyl ammonium
chloride ________________________ __
25
into a rich full bodied lather which does not de
The quaternary ammonium compounds can be
used alone or in mixtures with one another, and
The soap-like mixture of this example can be
mixtures of these with mixtures of one or more
molded or pressed into cakes and other forms if 20 salts of hexadecyl amine and octadecyl amine
desired. It can also be mixed with varying quan
may be used. The following example is an illus
tities of water and other compatible liquids to
tration of such a variation of the invention.
form paste-like products or liquids such as liquid
soap preparations.
Example '1'
teriorate but is quite permanent.
Instead of using the hydrochloride of hexadecyl
A mixture 01' quaternary ammonium com
amine, the acetate or other organic acid salt of 25
pounds is used which is derived from a mixture
the amine can be used. The mixture of the two
of higher alkyl amines obtained from coconut
substances can also be incorporated with inert
oils. Such a mixture of amines can be obtained
?llers of solid or semi-solid nature.
Example II
30
by saponifying coconut oil, separating the mix
ture of fatty acids thus produced, converting the
mixture of acids to their amides, dehydrating
A mixture consisting of about 75% by weight
the amides/to their nitriles and hydrogenating
of octadecyl amine hydrochloride and about 25%
the latterl'to a mixture of higher alkyl amines.
by weight of hexadecyl amine hydrochloride is
used. Such a mixture is obtained by saponi? 35 This mixture of higher alkyl amines can then be
converted by known methods into a mixture‘of
cation of ordinary animal fats to get a mixture
water-soluble quaternary ammonium compounds
of fatty acids, converting the latter to a mixture
of the general formula I
5"
of amides, dehydrating the amides to their ni
triles, hydrogenating the latter and converting
the resulting mixture of hexadecyl amine and 40
R-N-CH:
octadecyl amine to the mixture of hydrochlorides
/
mentioned.
200 grams of the mixture of hydrochlorides
where R represents the mixture of higher alkyl
thus prepared are mixed thoroughly with 50
grams of paratertiaryoctyl phenoxyethoxyethyl - radicals derived from the coconut oil, and X is the
anion of an acid.
dimethyl benzyl ammonium chloride to give a
1 lb. of a mixture or hexadecyl amine hydro
product which is even superior to the product of
chloride (75%) and octadecyl amine hydrochlo
example I in lathering and soap-like properties.
ride (25%) is mixed well with 5% ounces oi’ the
When used on the hands like a soap, no irrita
tion results and the skin is left clean, disinfected 50 mixed dimethyl benzyl high molecular alkyl am
and velvety smooth.
monium chlorides or the above formula derived
from coconut oils. This combination in its vari-‘
Example III
ous physical forms is an excellent lathering soap
like preparation.
Thisexample is carried out like Example I but
/CHI
' using octadecyl amine salt instead of hexadecyl 55
amine hydrochloride. A product having about
the same action and usefulness for germicidal
soap purposes as the product of Example I is
obtained.
Example IV
What I claim as my invention is:
-
1. A lathering soap-like preparation compris
ing a germicidal mixture, free from skin-irritat
ing properties, consisting 01' a substantially non
lathering germicidal water-soluble high molecu
60 lar weight quaternary ammonium compound and
a substance of the class consisting of a water
soluble acid addition salt of hexadecyl amine, a
As described above, numerous combinations
of various salts of hexadecyl and octadecyl
water-soluble acid addition salt of octadecyl
amines with various germicidal quaternary am
amine and mixtures of said acid addition salts,
monium compounds are possible in accordance 05 said germicidal mixture being free from skin
with the invention. Some further examples are
irritating compounds and salts of amines of
here given of other quaternary ammonium com
‘higher molecular weight than octadecyl amine
pounds which serve to give good lathering soaps '
and lower molecular weight than hexadecyl
when used with hexadecyl and octadecyl amine
‘ amine, and the weight of said substance in said
salts.
70 germicidal mixture ranging from about three
Grams
times to about four times the weight of said
(a) Hexadecyl amine hydrochloride ____ __ 400
Para-tertiary octyl phenoxyethoxy
ethyl trimethyl ammonium chloride- 100
(b) Hexadecyl amine hydrochlorlde_...___ 250
quaternary ammonium compound.
2. A lathering soap-like preparation compris
ing agermicidal mixture, tree from skin-irritat
75 ing properties, consisting of a substantially non—
2,406,902
6
lathering germicidal high molecular weight quat
ernary ammonium compound water-soluble at
least to the extent of one part in onehundred of
lathering germicidal water-soluble para-tertiary
octyl phenoxyethyoxyethyl dimethyl benzyl qua
ternary ammonium salt and a substance of the
class consisting of a water-soluble hydrohalic
acid addition salt of hexadecyl amine, a water
soluble hydrohalic acid addition salt of octadecyl
class consisting of a water-soluble acid addition
amine and mixtures of said acid addition salts,
salt of hexadecyl amine, a water-soluble acid
said germicidal mixture being free from skin-irri
addition salt of octadecyl amine and mixtures of
compounds and salts of amines of higher
said acid addition salts, said germicidal mixture 10 tating
molecular weight than octadecyl amine and lower
being free from skin-irritating compounds and
molecular weight than hexadecyl amine, and the
salts of amines of higher molecular weight than
weight of said substance in said germicidal mix
octadecyl amine and lower molecular weight than
ture ranging from about three times to ‘about four
hexadecyl amine, and the weight of said sub
times the weight of said quaternary ammonium
stance in said germicidal mixture ranging from, 15 salt.
about three times to about four times the weight
6. A lathering soap-like preparation compris
oi’ said quaternary ammonium compound.
ing a germicidal mixture, free from skin-irritating
3. A lathering soap-like preparation compris
properties, consisting of a substantially non-lath
ing a germicidal mixture, free from skin-irritat
ering germicidal water-soluble para-tertiary octyl
ing properties, consisting of a substantially non
phenoxyethyoxyethyl dimethyl benzyl quaternary
water and having a surface tension of less than
about forty dynes per square centimeter in 1%
aqueous solution at 25° C. and a substance of the
lathering germicidal water-soluble paratertiary
octyl phenoxyethoxyethyl dimethyl benzyl quat
ammonium salt and a substance of the class con
ernary ammonium salt and a substance of the
class consisting of a water-soluble acid addition
salt of hexadecyl amine, a water-soluble acid '
addition salt of octadecyl amine and mixtures
micidal mixture being free from skin-irritating
of said acid addition salts, said germicidal mix
compounds and salts of amines of higher molecu
lar weight than octadecyl amine and lower mo
ture being free from skin-irritating compounds
and salts of amines of higher molecular weight
than octadecyl amine and lower molecular weight
than hexadecyl amine, and the weight of said sub
stance in said germicidal mixture ranging from
about three times to about four times thelweight
of said quaternary ammonium salt.
-
sisting of a water-soluble hydrochloric acid addi
tion salt of hexadecyl amine, a water-soluble hy
drochloric acid addition salt of octadecyl amine
and mixtures of said acid addition salts, said ger
lecular weight than hexadecyl amine, and the
weight of said substance in said germicidal mix
ture ranging from about three times to about four
times the weight of said quaternary ammonium
salt.
i
'
7. A lathéring soap-like preparation compris
ing a germicidal mixture, free from ,skin irritat
ing properties, consisting of a substantially non
4. A lathering soap-like preparation compris
ing a germicidal mixture, free from skin-irritat
ing properties, consisting of a substantially non
lathering germicidal water-soluble para-tertiary
lathering germicidal water-soluble para-tertiary
octyl phenoxyethoxyethyl dimethyl benzyl quater
octyl phenoxyethoxyethyl dimethyl benzyl qua
ternary ammonium salt and a water-soluble mix
nary ammonium salt and a substance'of the class 40 ture of acid addition salts of hexadecyl amine and
consisting of a water-soluble mineral acid addi
octadecyl amine in the proportions of approxi
tion salt of hexadecyl amine, a water-soluble min
mately one mole of hexadecyl amine salt to 3
eral acid addition salt of octadecyl amine and
moles of octadecyl amine salt, and the total
mixtures of said acid addition salts, said germi
weightof said acid addition salts in the mixture
cidal mixture being free from skin-irritating
being about four times the total ‘weight of said
compounds and salts of amines of higher molecu
quaternary ammonium salt.
lar weight than octadecyl amine and lower mo
8. A combination of hexadecyl amine hydro
lecular weight than hexadecyl amine, and the
chloride and octadecyl amine hydrochloride, in
weight of said substance in said germicidal mix
ture ranging from about three times to about four
times the weight of said quaternary ammonium
salt.
the proportion of approximately 1 mole of the for
mer to 3 moles of the latter, with an amount of
para-tertiary octyl phenoxyethoxyethyl dimethyl
'
benzyl ammonium chloride equal to about one
5. A lathering soap-like preparation comprising
. fourth the total weight of said hydrochlorides.
a germicidal mixture, free from skin-irritating
properties, consisting of a substantially none
55
ALBERT L. RAWLINS.
Документ
Категория
Без категории
Просмотров
0
Размер файла
462 Кб
Теги
1/--страниц
Пожаловаться на содержимое документа