Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
96~1
BACKGROUND OF THE DISCLOSURE
This invention relates to a method for complexing metal
oxide particles in an organic medium as well as to a method for
dispersing or flocculating metal oxide particles in an organic
medium. This invention also relates to a magnetic recording
medium comprising a magnetic carrier and an improved magnetizable
coating provided on said carrier.
Many end use applications require that certain metal
oxide particles be complexed to achieve a desired effect such as
`dispersing the particles in an organic medium. For example, in
the recording industry, in order to achieve a useful magnetizable
coating on a non-magnetic carrier, it is necessary to finely
disperse magnetic pigments in a carrier by means of a binder.
Also, in the plastics industry, it is often necessary to uniformly~
disperse throughout a plastic an amount of a finely divided metal
oxide such as antimony trioxide or antimony pentoxide. In order to
achieve uniform stable dispersions of such metal oxides in organic
media, it is necessary to utilize an effective amount of a
complexing agent which in that application functions as dispersing
agent. Dispersing agents which have been used in the past
include, for example, N-acylsarcosine derivatives, as taught in
U.S. Patent No. 4,153,754. Also, for purposes similar to that
disclosed in the aforementioned patent, it is known to use
compounds such as N-tallow-l,3-diamino propane, especially in the
form of its dioleate salt.
An object of the present invention is to provide
improved complexing agents for use in dispersing or flocculating
finely divided metal oxide particles in organic media.
The foregoing and other objects will become apparent
from the following description of the invention.
~1~9601
SUMMARY OF THE INVENTION
There has now been discovered a method for complexing
finely divi~ed ~eta7 ox;de particles ;,l a,l organic medium
comprising incorporating into said medium an effective amount of a
complexing agent of the formula:
H R3
R~ , R5
,N C - C ~\
R2~ 1 I R6
H R4
wherein Rl is selected from the group consisting of alkyl and
;alkenyl groups containing from 4 to 22 carbon atoms, aryl groups
containing from 4 to lO carbon atoms, alkyl and alkenyl groups
!containing from 4 to 22 carbon atoms substituted with one or more
aryl groups containing from 4 to lO carbon atoms and aryl groups
.containing from 4 to lO carbon atoms substituted with one or more
;alkyl or alkenyl groups containing from l to 22 carbon atoms; R2
is selected from the group consisting of hydrogen,
-(CH2CH20)nH, wherein n is an integer from l to lO, alkyl
and alkenyl groups containing from l to 22 carbon atoms, aryl
groups containing from 4 to lO carbon atoms, alkyl and alkenyl
groups containing from l to 22 carbon atoms substituted with one
or more aryl groups containing from 4 to lO carbon atoms and aryl
groups containing from 4 to lO carbon atoms substituted with one
or more alkyl or alkenyl groups containing from l to 22 carbon
atoms; R3 and R4 are independently selected from the group
consisting of hydrogen, -CH3, and -CH2CH3; and Rs and R6
are independently selected from the group consisting of hydrogen,
-CH3, -CH2CH3, and -(CH2CH20)nH wherein n is an
integer from l to lO.
,. 3
!. .
9601
The present invention also provided a magnetic recording
medium comprising a non-magnetic carrier and a magnetizable
~oatin~ prc~ ed ~n said carrier, said magnetizable ~oating
comprising a binder and magnetic pigments finely dispersed therein
by means of a dispersing agent, said dispersing agent being a
compound of the formula:
H R3
Rl I I ,R5
- N - C - C N
R2~ l I P~6
H R4
wherein R1 is selected from the group consisting of alkyl and
alkenyl groups containing from 4 to 22 carbon atoms, aryl groups
containing from 4 to 10 carbon atoms, alkyl and alkenyl groups
containing from 4 to 22 carbon atoms substituted with one or more
aryl groups containing from 4 to 10 carbon atoms and aryl groups
containing from 4 to 10 carbon atoms substituted with one or more
alkyl or alkenyl groups containing from 1 to 22 carbon atoms; R2
is selected from the group consisting of hydrogen,
-(CH2CH20)nH, wherein n is an integer from 1 to 10, alkyl
and alkenyl groups containing from 1 to 22 carbon atoms, aryl
groups containing from 4 to 10 carbon atoms, alkyl and alkenyl
groups containing from 1 to 22 carbon atoms substituted with one
or more aryl groups containing from 4 to 10 carbon atoms and aryl
groups containing from 4 to 10 carbon atoms substituted with one
or more alkyl or alkenyl groups containing from 1 to 22 carbon
atoms; R3 and R4 are independently selected from the group
consisting of hydrogen, -CH3, and -CH2CH3; and Rs and R6
are independently selected from the group consisting of hydrogen,
-CH3, -CH2CH3, and -(CH2CH20)nH wherein n is an
integer from 1 to 10.
. .
~9601
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
As indicated, the present invention provides improved
complexing agents. Said compiexing agents be10ng to a class of
compounds of the following formula:
H R3
Rl l l , R5
> N C--C N
H R4
With respect to the foregoing formula, Rl may be
selected from the group consisting of alkyl and alkenyl groups
containing from 4 to 22 carbon atoms. Preferably R1 is a
long-chain alkyl group having from about 8 to about 18 carbon
atoms. R1 may therefore be any long-chain alkyl group3 such as
those derived from naturally occuring fats and oils such as cocoa,
tallow, and soya. The Rl group may also represent an aryl group
containing from about 4 to about 10 carbon atoms or an alkyl or
alkenyl group as defined above substituted with one or more of
such aryl groups, such as a phenylstearic group. Likewise the
aforementioned aryl group may be substituted with an alkyl or
alkenyl group containing from 1 to 22 carbon atoms. The R2
group is independently selected from hydrogen, -(CH2CH20)nH,
wherein n is an integer from 1 to 10, and the same group dS
Indicated for R1, but-wherein the alkyl and alkenyl groups may
contain from 1 to 22 carbon atoms.
~1~9601
When reference is made in the present application to an
aryt group, the ~rm should be understood to include any a~olnatic
system meeting the specified criteria, such as having from 4 to 10
carbon atoms. The aryl group may therefore include hetero atoms
such as, nitrogen, sufpher, and oxygen as part of the aromatic
group.
The R3 and R4 groups are independently selected from
the group consisting of hydrogen, -CH3 and -CH2CH3.
Preferably R3 and R4 are both methyl. The Rs and R6
groups are independently selected from the group consisting of
hydrogen -CH3,-CH2CH3, and -(CH2CH20)n, wherein n is
an integer from 1 to 11. Preferably, Rs and R6 are hydrogen.
The most preferable class of compounds is represented by`
the foregoing formula wherein R1 is an alkyl group containing
from about 4 to about 22 carbon atoms, preferably from about 8 to
about 18, and most preferably it is derived from tallow, R2 is
hydrogen, R3 and R4 are both methyl, and Rs and R6 are
both hydrogen. The most preferable compound is therefore
l-(N-tallowamino)-2-alnino-2-methyl propane.
Other compounds which are useful in the practice of the
present invention include l-(N-dodecylamino)-2-amino-2-methyl
propane, l-(N-phenylstearylamino)-2-amino-2-methyl propane,
~ l~g601
l-(benzyl-N-tallow amino)-2-amino-2-methyl propane,
l-(N-morpholino)-2-amino-2-methyl propane, l-(N-di-n-butyl
amino)-2-amino2-methyl propane, l-(tallow-N-ethanolamino)-Z-
diethanolamino2-methyl propane, l-~methy~ N-oc~adecyl
amino)-2amino-2-methyl propane, l-(N-n-butyl amino)-2-amino-2-
methyl propane, and l-(N- eicosylamino)-2-amino-2-methyl propane.
The compounds of the present invention may be
synthesized in accordance with chemical techniques known to those
skilled in the art. One may refer for guidance to A. G. Johnson,
JACS. 68,14(1946).
To prepare the N-tallow-2-methyl-1,2-propane-diamine
utilized in the present invention, one may, for example, react 393
grams of primary tallow amine with 147 grams of nitropropane in a
~ ~ .
t~ one-liter stainless steel stirred Parr autoclave heated to 90C.
121 grams of formalin (37Y) may be added under pressure and the
reaction mixture heated at 90C for approximately six hours to
obtain 95YO of the desired nitro-intermediate. 500 grams of the
intermediate may then be reacted with hydrogen utilizing 22.5
grams of nickel catalyst and 35 grams of a filter aid, in a
rn~
one-liter stainless steel, stirred Parr autoclave. The
hydrogenation may be accomplished at 60C, 1000 psig hydrogen for
sever hours. The product may contain approximately 83~ of the
desired diamine and 15% of the corresponding monoamine.
As used herein and in the appended claims, the term
"complexing" is used to mean any chemical, physical or other
interaction between the complexing agent of the present invention
and the metal oxide particle being complexed to cause a chemical,
physical or other association to occur between the complexing
agent and the metal oxide particle. The formation of true
organo-metallic complexes is thus not necessary.
-- .. . . , . ~ ,
~149~01
In the present application and the appended claims the
term "dispersing" is meant to include physically stablizing the
metal oxide particles against either settling, in the case of
liquid~ sUcpensions~; nr migrating, as in the case of metal oxides
which are dispersed throughout a polymeric material. The term
"flocculating" is used to mean precipitation, a~glomerationor
other physical association of the metal oxide particles so as to
form a recognized increased density of the metal oxide particles.
The organic medium which is utilized in the present
process may vary widely and includes liquid and solid organic
substances in which finely divided metal oxide particles are
incorporated. Thus, useful organic media may include organic
liquids, such as mineral oil, synthetic oils, petroleum oils, and
typical organic solvents such as methylethyl ketone,
methylisobutyl ketone, and toluene. Of course, mixtures of
various organic materials may be utilized as the organic medium
for the purpose of practicing the present invention. For
example, a mixture l:l:l of methylethyl ketone, methylisobutyl
ketone, and toluene may be utilized.
With respect to the finely divided metal oxide particles
which are useful in the practice of the present invention,
typically particles having sizes from about O.Ol microns to about
lO0 microns are useful in the practice of the present invention
when dispersion of the particles is desired. Such particles may
have any physical shape, regular or irregular. Thus such
particles may be spherical or may be acicular such as Fe203
and CrO2 particles which genera!ly have a length of about O.l to
l.0 micron and a thickness of about O.Ol to about 0.2 micron. The
type of metal oxide particles utilized is not critical. Thus, for
examplej,-the metal oxide particles may be any of the known oxides
of iron, nickel, copper, vanadium, molybdenum, uranium, mercury,
~ cl n tilnony
~ chromium, magnesium, titanium, and rn~KI~ as well as others.
,. .
9601
In the practice of the present invention the complexing
agent may exist solely in the form identified by the formula
hereinabove. The complexing agent may also exist in a wholly or
parttal~y neutralized torm. lhus, dS the complexing agents of the
present invention are diamines, they may be wholly or partially
neutralized with acids, preferably fatty acids, such as oleic
acid. Thus, for every mole of diamine present, the complexing
agent may exist as either the mono- or di- salt thereof. An
especially useful dispersing agent appears to be
N-tallow-2-methyl-1,2-propane-diamine dioleate.
When the complexing agent is to function as a dispersing
agent the actual quantity of dispersing agent utilized for
dispersing finely divided metal oxides in any particular organic
medium will depend greatly upon many factors such as the size of
the metal oxide particles, the type of metal oxide particles, the
quantity of metal oxide particles present, and the nature of the
organic medium in which the metal oxide particles are to be
dispersed. In any event, the amount of dispersing agent present
should be an effective amount. By the term "effective amount"
there is meant a quantity of dispersing agent sufficient to at
least partially stablilize the metal oxide particles in the medium
against settling or migration. The amount need not be sufficient
to maintain the finely divided metal particles dispersed
throughout the organic medium indefinitely, but simply sufficient
to increase the stability of the system over that which would
otherwise be obtained without the presence of the dispersing
agent.
When the complexing agent is to function as a
flocculating agent, again the quantity utilized will also depend
upon the factors outlined above with respect to dispersing agents.
' '9 , I
960~
The amount utilized should he an "effective amount" which is meant
to indicate a quantity sufficient to cause at least some increased
degree of flocculation of the metal oxide particles over that
which would otherwise occur in the absence of the dispersing
agent.
~ hen the present invention is utilized in the field of
magnetic recording media, useful results are achieved. In such an
application area it is customary to utilize a magnetic recording
medium comprising a non-magnetic carrier as well as a magnetizable
coating which is provided on the carrier. The magnetizable
coating comprises a binder, as well as a magnetic pigment which is
maintained finely divided therein by means of a dispersing agent.
A typical carrier is manufactured from a synthetic resin, for
example polyester or polyvinyl chloride, but may alternatively be
paper, glass or metal. The carrier may have the shape of a tape,
plate, disk, or the like. For the purpose of dispersing a
magnetic pigment in a binder, it is believed that a suitable
quantity of dispersing agent of the present invention is from
about l to about lO percent, by weight, calculated on the weight
of the magnetic pigment, preferably from about 2 to about 5
percent, by weight. Typical binders which are utilized include
polyvinyl chloride, polyvinyl acetate, polyacrylate, polyester,
polyester amides, polyurethanes and copolymers of at least two
monomers selected from the group consisting of vinyl chloride,
vinyl acetate, acrylonitrile, vinyl alcohol, vinyl butyral, and
vinylidene chloride. Readily useful binders in particular are
polyurethane and partially hydrolyzed copolymers of vinyl chloride
and vinyl acetate.
The magnetizable particles present in the binder are
conventional and typically are, for example, iron powder,
Fe203 particles, and CrO2 particles.
'10
96Vl
To practice the present invention, by use of a ball
mill, one may thoroughly mix the magnetizable particles, the
dispersing agent of the present invention, and a part of the
binder in a s~lven~ for the bin~r. The remainuer of the binder
dissolved in a suitable solvent and a lubricant may then be added
and the whole may be further ground in the ball mill for a few
hours. Typical solvents for the binder include organic liquids,
such as esters, for example ethyl acetate, ethers, for example
tetrahydrofuran, ketones, for example methylethylketone,
methylisobutyl ketone, and cyclohexanone, hydocarbons, for
example, toluene and chlorinated hydrocarbons, for example,
1,2-dichloroethane. Certainly, the mixing of the materials may be
accomplished in one step in which all of the ingredients are
simultaneously supplied to the ball mill. The quantity of
magnetizable particles (pigment) is approximately 60 to 85
percent, by weight, calculated on the overall amount of the
magnetizable coating. After thoroughly grinding the dispersion in
the ball mill, the larger magnetizable particles may be sieved out
and the resulting magnetizable coating provided on the carrier in
a uniform layer. The whole structure may then be dried and the
solvent evaporated and a recording layer having a thickness, for
example, from about 2 to about 10 microns may remain on the
carrier. The layer may be hardened, if desired, or may be
subjected to a calendering process in which the surface of the
layer becomes smoother.
The present invention will describe in further detail in
the following non-limiting examples.
EXAMPLE I
In this example the utility of a compound of the present
invention, 1-(N-tallowamino)-2-amino-2-methyl propane, as a
suspending agent for iron oxide (Fe203) in cosmetic grade
11 1
~ 1~96Vl
mineral oil is demonstrated and compared to the utility of a
A" previously known suspending agent, Sarkosyl NL which chemically is
sodium lauryl sarcosinate. As the Sarkosyl NL material is
available in a 30Zo aqueous solution, two prior-art compositions
5 were utilized in the comparison, one representing the material as
~ 7
available in the 30% solution, and the other utilizing Sarkosyl NL
which had been first dried to produce a 100% active material. The
components i n the systems were as fol 1 ows:
(1 ) 1% Fe203 (200-~00 mesh) ~2) 170 Fe203 ~
3.33% Sarkosyl NL (30%) 1% Sarkosyl NL (dried)
95 . 67% Mi neral Oi 1 98% Mineral Oil
(3) 1% Fe203 (200-400 mesh)
1% 1-(N-tallowamino)-2-amino-2-methyl propane
98% Mi neral Oi l
Suspensions were first stirred for 48 hours, usins a
~g
Teflon coated stirring bar and magnetic stirrer. The suspensions
were then stored in sealed jars and not disturbed for the durationO
After one day, approximately 90% of the Fe203 in both samples 1
and 2 had settled out, while sample 3 was still in suspension.
After 4 weeks duration, approximately 60% of the Fe203 in
sample 3 had settled out. Even after 8 weeks duration, notmore
than 90% of the Fe203 had settled o.~t of sarnple 3, containing the complexing agent
of the present invention.
EXAMPLE I I
In accordance with the procedure utilized in Example I~
several other complexing agents in accordance with the present
invention were utilized in combination with 0.1~O Fe203 in
mineral oil. The complexing agents utilized and the settling
rates are shown in Table I. In Table I the settling rates are
given in days and are broken down in accordance with the length of
time needed to settle lG%, 50Z, and 90%, respectively, of the
F e 2 0 3 i n t h e d i s p e r s i o n .
9601
EXAMPLE III
Following the procedure of Examples I and II, several
complexing agents of the present invention were utilized to
~. CrOa
t~b~ complex CrO~ in mineral oil. Table II contains the results
obtained in the same manner as in Table I.
Example IV
Following the procedure of Examples I and II, several
complexing agents of the present invention were utilized to
complex Sb203 in mineral oil. Table III contains the results
obtained in the same manner as in Table I.
EXAMPLE V
The same procedure as utilized in Example I and II was
used to complex TiO2 in mineral oil. The results are shown in
Table III in the same manner as in Table I.
, 13
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ILI ~ -- O _ I I~ Z
_1~1 C z >_~_ c~ C _~_
I ~ 1~1 0 cl
_ ~ I J ~ I I J JCl
t_~ ~ ~ Z OC~ Z Z ~ ~ 3
O ~ ) O
L~ 2 -- Q C 3 _ ~ J
~Il~:~- Q I O ~ ~ ~_) J
O I 1~1 0 -- _ I I ~_CC
C~ Q Z ~ ~ _ I-- c 1~11-- 0
z z a:~ z ::~ ~ _ z z 2 1--
.~ ~ ~ ~ Z
I I I I I I I I I I O
_ _ . ,~
. . .
- 17 -
~9601
From the foregoing tables it is evident that some of the
complexing agents of the present invention are effective at
A s~qbi~fy
increasing the dispersion stablility of Fe203 in mineral oil
over the same system withou~ d ~Isp~rslng agent, wnereas others,
1-(N-morpholino)-2-amino-2-methyl propane, are effective at
flocculating Fe203 in mineral oil.
18
il I
