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Patented Oct. 29, 1946
2,410,124
I UNITED STATES PATENT OFFICE
PRODUCTION - OF PLASTICIZED PROLAMINE
AND DERIVATIVE COMPOSITIONS
Willard L. Morgan, Columbus, Ohio, assignor of
one-half to A. E. Staley Manufacturing Com
pany, Decatur, 111., a corporation of Delaware,
and one-half to American-Maize Products
Company, New York, N. Y., a corporation of
Maine
\
No Drawing. Application November 24. 1944.
-
I
Serial No. 565,065
18 Claims.
1
This invention relates to plasticizers for pro
lamines, and to the resultant plasticized pro.
lamine and “prolamine-base’-’_ compositions.
It is an object of this invention to provide novel
plasticized “prolamine-base” compositions.
' ~
It is another object of this invention toprovide
compositions with plasti
novel “prolamine-base"
(Cl. 106-153)
-
.
2
ticizers for this purpose have been proposed, but
most of such prior art materials have exhibited
low plasticizing activityor undesirable charac
teristics such as incomplete compatibility, high
melting point,‘ strong odors, water solubility or
rapid loss by volatilization from the prolamine,
thereby, and in other ways, resulting in composi
cizers exhibiting highly desirable compatibility
tions which are unsatisfactory commercially in
and solvency for the prolamines, thus permitting
one respect or another.
the preparation directly ofv plastic masses, coat 10 In this invention there is set forth the surpris
ings and ?lms with the prolamines.
ing discovery that alkyl branched-chain ‘satu
It is a still further object of this invention to
rated and unsaturated organic fatty acids in
provide novel “prolamine-base” compositions
which the total number of carbon atoms in a
having plasticizers for prolamines of improved
molecule lies in the range 4 to 18, inclusive, func
compatibility characteristics which compositions
may be applied in solvents as adhesives or coat
ings, or thus applied in forming ?lms or plastics.
Other and ancillary objects of this invention
15 tion as remarkably effective plasticizers for pro
lamines. Thus, for example, 2-methyl propenoic ’
acid, ,2-ethyl butanoic acid (2-ethyl butyric acid),
2-ethyl hexanoic acid (Z-ethyl caproic acid),
will be'apparent from the detailed description
2-ethyl octanoic acid (2-ethyl caprylic acid),
and examples thereof hereinbelow set forth.
2-ethy1 decanoic acid (Z-ethyl capric acid), 2-=tri
The prolamines have long been established as 20 methyl
acetic acid. (pivalic acid), 5-methyl hex
exhibiting certain properties unique among the
anoic
acid
(5-methyl caproic acid); 2-propyl bu
proteins, and as such have been classi?ed by
tanoic acid (2-propyl butyric acid), 2-octyl de
workers dealing with proteins as a separate group
canoic acid (2-octyl capric acid), are effective
thereof. By de?nition, the prolamines are those 25 plasticizers
for the prolamines.- Furthermore,
proteins characterized by solubility in aqueous
mixtures
of
these acids as, for example, 2-ethyl
ethyl alcohol. They are found only in cereal
butanoic and 5-methyl hexanoic acids, combined
grains and, contrasted to other proteins, are high
in any proportions whatever with each other con
in the amino acid proline and amide nitrogen
stitute
e?ective prolamine plasticizers. The
content, and are de?cient in free amino groups
30
branched-chain
fatty acids may also be employed
and in lysine. They are very nearly or entirely
as plasticizers in prolamine plastics in combina
insoluble in water and weak a/queous acid solu
tion with other known plasticizers such as dibutyl
tions, but are freely soluble in dilute alkali solu
> tartrate or para toluene’ sulfonamide.
tions in water.
.
The
amount of plasticizer which may e?'ectively be
Althoughlin the following description and ex
with the prolamine to result in a
amples I shall refer to the particular prolamine 35 incorporated
useful, plasticized composition occupies an ex
zein which is derived from corn, it is to be under~v
tremely broad range of percentages based on total.
stood that this invention is equally applicable to
product composition, and the amount employed
the other prolamines, and “prolamine-base” pro
will depend upon the properties desired in the
teins, that is, to hordein, derived from barley; to 40 plastic to be produced. For example, if 5 per
ka?rin, derived from sorghum; to gliadin, which
cent (bylweight of the resultant composition) of
is derived from wheat; to secalin, derived from
branched-chain fatty acid plasticizer be incor- rye, and to the cereal glutens generally;
porated with, say, the prolamine zein, the plasti
The diverse and potentially large-scale utiliza
tion of plasticized prolamine compositions has 45 cized product is hard and tough in character.
When on the other hand. increasingly greater
long been attractive, and the discovery of satis
percentages of plasticizer are incorporated with
factory plasticizers for the prolamines in gen
the zein, the resultant compositions exhibit in
eral, and, in particular, for the prolamine zein
creased flexibility and softness such that at a
which is of industrial importance, has been the
content of 50 percent by weight in the product,
object of extensive investigation. Various plas 50 the
plastics often resemble many rubber articles.
2,410,124 '
4
3
ing; utilized for impregnating and coating, par
manently soft and tacky. Fundamental product
ticularly for grease and water-proo?ng purposes;
and applied to the production of flexible ?lms,
lacquers, wall and floor paints, deck enamels,
grease and moisture-proof lacquers for applica~
When 80 to 95 percent by weight of the resultant
composition is plasticizer, the products are per
characteristics may be regarded, then, as a func
tion of plasticizer content, and it therefore fol
. .tion to metallic surfaces, protective varnishes for
lows that the amount of plasticizer to be incor
printed and other paper surfaces, adhesives, lami
porated with a prolamine will be ‘determined by
nated products of various types, plastic compo
the use to which the product is to be put. Fur
sitions, linoleum, oilcloth, and the like. These
ther in this regard, it has been discovered that
uses are, of course, cited as being illustrative only
10
product hardness is de?ned to a certain extent
of the diverse applications of the novel composi
by the nature of the branched-chain fatty acid
tions, and as in no way imposing limitations
plasticizer itself. Thus, in general, the greater
thereon, there being many related and other uses
the length of the branched-chain, or the more
which will at once be apparent to those skilled in
complex the branched nature of the fatty acid,
such
arts.
15
the harder the plasticized prolamine composition
In practicing this invention, the optimum
for any given amount of plasticizer. The pres
quantities of plasticizer to be incorporated to se
ence of hydroxyl or of amino groups, or of un
cure the qualities desired for the use to which the
saturation in the acid structure, is found to im
resultant composition is to be put, will at once be
prove the softening or plasticizing action and
apparent to those skilled in the respective arts
compatibility with the prolamine. It is evident, 20 from the further description and examples here
then, that a wide range of plasticized composi
inafter set forth'.
tions are obtainable ‘by- means of this discovery,
As a general procedure, the prolamine and
and, further, that product characteristics may be
plasticizer may be thoroughly mixed in the de
modi?ed at will by judicious choice of plasticizer
sired proportions at room temperature. The mix
and the quantity thereof incorporated with the 25 ture may then be heated and maintained at a
prolamine.
more or less elevated temperature until homo
It has previously been proposed to plasticize
geneity has been attained, as evidenced by disap
various proteins, including the prolamine zein,
pearance of the prolamine and plasticizer as in
with saturated and unsaturated straight-chain
dividual entities with consequent formation of a
fatty acids such as, for example, butyric acid,
single, homogeneous mass. This may be carried
caprylic acid, caproic acid, capric acid, stearic
out in internal mixing machines or upon plastic
acid, linoleic acid, oleic acid, and the like. How
milling rolls. Pigments, dyes, ?llers, resins and
ever these present various disadvantages, thus:
the like may be added to the masses while in these
the problem of offensive odor practically pre
machines. Upon cooling to room temperature,
cludes use of the shorter-chain acids; longer
the plasticized composition will be more or less
chain acids of this type are very poorly com
hard and pliable, depending upon the amount and
patible and exhibit negligible plasticizing activity.
On the other hand, the branched-chain fatty
acids of the present invention are not only ef
fective prolamine plasticizers, but are character
ized by practically unnoticeable, bland, mild
odors. Furthermore, these branched-chain com
pounds exhibit relatively high boiling points, gen
erally increasing with molecular weight, and are
consequently subject to very slow evaporation
from the compositions in which they are incor
porated. For example, of the suitable plasticizers
nature of ,plasticizer incorporated therein, as
hereinabove set forth. In the incorporation of
other materials with plasticized prolamlne com
40 positions for the production of lacquers, sizing,
coating or impregnating materials, printing inks,
adhesives, or the like, it is frequently advanta
geous to mix all of the individual components
45 thereof including solvents at the outset of opera
tions, rather than to plasticize the prolamine pre
liminarily and thereafter to incorporate the plas
ticized product with the other compounding ma
for the present invention, at normal pressures
terials, although such may be done. However the
(760 mm. of mercury), trimethyl acetic acid boils
sequence of such operations is not at all critical,
at a temperature of about 163.8° C. 2-ethyl 50 and'in general will be governed by the character
butyric acid (2-ethyl butanoic acid) in the range
of the technical operations involved, by the ar
195 to 197° C. Z-methyl propanoic acid (isobutyric
rangement thereof which results in optimum
0.,
2-ethy1
ca
‘acid) at a temperature of 154.4”
process economies, and by the established pro
proio acid (Z-ethyl hexanoic acid) in the range
duction methods conventionally practiced in each
223 to 225° Gui-methyl propenoic acid (meth 55 particular industry.
acrylic acid) at a temperature of 163° C., and
As hereinabove set forth, the plasticizers of
2-octy1 capric acid (Z-octyl decanoic acid) boils
the present invention may be employed, alone or
at a temperature of 270 to 275° C. under a pres
in conjunction with other known plasticizers, for
sure of 100 mm. of mercury. Branched-chain
various plastic modi?ed prolamine compositions,
fatty acids having a total number of carbon 60 such as, for example, aldehyde reacted prolamine
atoms outside of the preferred range of 4 to 18
plastics. It is well known to react prolamines
inclusive hereinabove set forth are not particu
with aldehydes, particularly formaldehyde, to
larly well suited for plasticizing prolarnines since
form solutions, coatings, and thermosetting
acids of this type of greater than 18 carbon
plastic compositions of improved water resistance
atoms exhibit little if any plasticizing activity.
Further, branched-chain fatty acid compounds
within this preferred range are substantially wa
ter-insoluble save for the lowest members there
- of, which are soluble to a certain extent.
The plasticized compositions resulting from
practice of this invention have been found of ver
satile utilities not only as plastic rods, sheets and
molded articles, but also as coatings of various
types. Thus, for example, these compositions
may be made into solutions and applied as a siz
and widely varying properties depending upon
the nature and amount of ingredients incorpo
rated therein, and upon the temperature and
duration of aldehyde reaction. If_ desired, the
0 plasticized prolamine compositions of this in
vention may be aldehyde-cured according to con
ventional techniques, to result in useful plastics
and coating compositions which, after curing, are
no longer thermoplastic, but are thermosetting
75 in nature, and by reason of the plasticizers set
2,410,124
forthin the present invention are ?exible and
portant practical applications thereof. It is to
be explicitly understood that the. present inven
tough. It is apparent that while aldehyde cur
ing operations with plastics and coatings are
preferably carried out upon conclusion of plasti
cization of the prolamine material, it is possible
to add the plasticizers to solutions of prolamines
which have been ?rst reacted with the aldehydes.
The prolamines constitute a large‘ portion of
tion is in no way limited to the applications
thereof set forth in these examples,'nor to the
particular ingredients or to the amounts therein
speci?ed, since equivalent ingredients in varying
the protein found in the starchy or endosperm
parts of the cereal grains and they are commonly 10
isolated from such starchy portions after the
I grains have been de-germinated, as for example
in cornstarch manufacture by the wet-milling
process or in the manufacture of wheat or other
?ours by the dry-milling process. The starches
may be removed by mechanical washing action 15
as in the preparation of wheat gluten, by wet 4 materials. Thus, for example, methyl Cellosolve,
kneading of the ?oury mixture, or they may be
aqueous ethyl alcohol, aqueous isopropyl alcohol,
20
aqueous diacetone alcohol, carbitol, methyl
carbitol, are individually solvents both for zein
and for the plasticizers used in this invention, and
purposes functioning as auxiliary solvents of
which many are known in the prolamine solvent
?eld.
30
_
Example 1 I
and 30 parts of
placed in a jacketed
35
0.,
temperature in the general
0., for a period of about
60 minutes, at which time plasticization of the
40 zein had been substantially completed vas evi~
denced by disappearance .of the zein and of
considerable proportion of a prolamine.
as a suitable corn protein for forming plastics
we may use the corn gluten resulting from the
commercial separation of cornstarch in the wet
milling process, which gluten may contain from 45
40 to 65% by weight of corn proteins primarily
of prolamine nature, a large part being the al
starch with small quantities of cellulosic bodies 50
and fatty substances. Partially ‘puri?ed corn
glutens such as those produced in Shildneck
Patent U. S. No. 2,274,004 by further removal of
starch with acids or as shown in Schopmeyer
55
Patent, U. S. No. 2,310,104, wherein fatty mate
By weight 10 parts of Z-ethyl hexanoic acid, Q
5 parts of 2-ethyl decanoic acid, 15 parts of oleic
acid, 5 parts of 2-methyl propanoic acid, and 10
rials are removed and which contain'60 to 100% -
by weight of protein content, may also be used in
60
mixer to a temper
ature in the general range of 120° to 135° C., while
60 parts of zein were gradually mixed in during
protein is
the course of an hour.
used in the description here given and in the
The plastic dough wash
appended claims, I include by such term not
further
worked for a period of about 20 minutes,
65
alone the puri?ed prolamines isolated
zein was substantially complete. Upon cooling a
small portion to room temperature the product
70
and pliable at
vordinary temperatures, and thus directly usable
to a more or less limited extent, the scope of the
present invention, and the presently more im
as a plastic. When cooled to below 70° C., there
was incorporated in the main plastic batch by
75 weight 30 parts of rosin and thereafter 1 part of
' 2,410,124
Example 5
By weight 40 parts of zein and 60 parts of
trioxymethylene. The batch was then sheeted
at about 70° to 80° C. on rubber rolls and pieces
' 2-ethyl hexanoic acid were dissolved at room tem
perature in a solvent mixture comprised of about
were then pressed in a heated press at 250 lbs.
per square inch at 135° C., for one halt hour.
This gave aldehyde-cured plastic articles gener
ally similar to those produced by Example 1 but
30 parts by weight of methyl Cellosolve and about
'70 parts by weight of 95% (by weight) ethyl a1
distinguished therefrom by not being thermo
directly applicable for‘ many uses; for example,
cohol. The resulting solution was found to be
plastic and by having greater water-resistance.
for sizing, coating, impregnating and waterproof
ing textiles, paper, wood, tinplate and the like.
Example 3
As a coating material, the solution was emi
A rubber-like plastic suitable for use as a shoe
sole was made by mixing in an internal mixer
the following ingredients:
nently suited for application ‘to varnished, lac
quered, and the like surfaces. Furtheryit was
found to form removable strong, tough, pliable,
Parts by weight
Zein _________________ __, ________________ ..-
3'1
2-ethyl hexanoic acid ___________________ __
35
15 transparent films when cast upon an oiled or
waxed glass surface. In addition to these proper
ties, the films were oil-resistant, hard and non
tacky in nature, and furnished an excellent sur
Dibutyl butanoic acid _______ __' __________ __ 91/2
Trioxymethylene _______________________ __ 11/2
Clay ________ _'______' ____________________ __
face for printing purposes.
12
Carbon black ___________________________ __
When applied to
20 paper there resulted excellent grease- and mois
5
ture-proof coatings, giving ?exible wrappings
The zein and plasticizer were first entered into
the internal mixer and‘after working for ap
proximately one hour the pigments were added
suitable for food-stuff packaging. Coated upon
tinplate the coating was found to withstand can,
forming operations and repeated flexing without
in small portions at a time more readily to pro 25 cracking. The coating was excellent in grease- '
vide a homogeneous mixture. The working of
resistance.
the mass readily provides heat which was removed
by cooling to. below 80° C., by a water-cooled
jacket upon the internal mixer. Thereafter the
Example 6.
By weight 20 parts of cereal gluten derived
- trioxymethylene was quickly introduced and 30. from corn, 40 parts of Z-propyl butanoic acid, 10
parts of tetraethylene glycol and 25 parts of car
milled in during a short period of time of five
bon black were thoroughly ground together on
minutes or less, at below about 80° C. The plastic
a roller mill. The resultant product was found
mas'swas then removed from the internal mixer
to be suited for use as an ink for printing cotton
and sheeted out at below about 80° C. upon a
rubber milling roll and portions or the thermo 35 bags.
~
Example 7
plastic uncured sheet were then placed within
an ordinary shoe sole mold such as is used in’
By weight 4'1 parts of zein, 53 parts of 2-ethyl
the rubber trade. Curing was then carried out >
decanoic acid, 100 parts of clay, and about 50
by heating such mold to 130° C., for one-half hour
parts of 80% (by volume) aqueous ethyl alcohol
under a hydraulic pressure of 100 to 500 lbs. 40 and 15 parts of ethyl lactate were thoroughly
per square inch. Such pressures have been found 7
mixed together and ground in a ball mill for a
suitable in the manufacture of plastics from
period of about 24 hours. The resultant compo
prolamines. The product was tough and flexible
sitionwas knife-coated onto a sized woven sheet
and in general had qualities similar to ordinary
ing base, which was then force-dried'for about 1
.45
hour at a. temperature of about 150° F. The ,re- '
rubber shoe soles. Example 4
sultant “oilcloth” type of product exhibited‘ ex
cellent wearing qualities, resistance to ?exing
As an example wherein there is employed a
and to the action of water, acids, and greases.
crude mixture of cereal proteins ‘containing pro
lamines, hard prolamine plastic articles such as 60
Example 8
door knobs of‘ a black color were made by mold
By weight 95 parts of zein, 5 parts or 2-octyl
ing under similar conditions to those used in
Example 3 masses of the following plastic mix
ture:
'
decanoic acid, 0.1 part or oil-soluble dyestuff
Yellow OB, and about ‘240 parts'of a solvent mix- .
Parts by weight
Corn gluten, 60% protein content ________ __ 40 55
Nevillac 10° (coumarone indenephenol resin,
Neville 00., Pittsburgh, Pa.) ___________ __ 35
ture comprised of 80 parts by weight of diacetone
alcohol and 160 parts by weight of 95% (by vol
ume) ethyl alcohol, were mixed together over
night in a ball mill. The product was a shellac
substitute eminently suited for coating wooden
2-ethyl decanoic acid _____________________ -_ 10
Asbestine ___'____-_ _______________________ __
8
Channel black ______________________ _,______
5
Trioxymethylene ________________________ __
2
In making the plastic mixture the plasticizer,
surfaces.
'
Example
9
By weight75 parts of gliadin and 25 parts of
_ 2-ethyl hexanoic acid were thoroughly mixed, at
resin and gluten were ?rst mixed in a plastic
masticating machine. The pigments were then
incorporated by adding small portions at a time
and the mass worked until it was thoroughly
uniform. While still in the plastic machine, the
mass was then cooled to ‘75° C., and the tri
oxymethylene quickly introduced. After further 70
working for approximately ?ve minutes to dis
tribute the formaldehyde-curing compound uni
formly throughout the mass, the mass was re
moved from the mixer and sheeted at below ‘75°
to 80° C., in milling rolls, prior to actual molding
room temperature. The resultant mixture was
heated to a temperature of about 127° C., and
maintained at a temperature in the general range
120° C. to 135° C., for a period of about 35 min
utes, at which time a clear, homogeneous solution
indicating complete plasticization of the gliadin,
had resulted. Upon cooling to room temperature
a clear, transparent, substantially colorless, ther
moplastic product resulted. When all of the re
sulting material is dissolved at room temperature
in a volatile solvent mixture comprised of about
65 parts by weight of 95% (by volume) ethanol,
operations at temperatures above 120° C.
!____-_
' 2,410,124
about 20 parts by weight of glacial acetic acid,
.
and about 15 parts by weight of water, the result
ant composition exhibited excellent properties as
a quick-drying adhesive. In place of ‘the 75
parts of gliadin a similar glue may be made by
substituting 75 parts of hordein. '
.
10
merous ?exings. The mixture may also be em
pioyed as an interior wall paint preferably after
adding per one part by weight thereof 0.5 part
by weight of water;
'
Example 14
Example ‘ 10
A zein dispersion in water'with ammonium ros
inate was prepared according to the method of
Drewsen and Little (U. S. Patent No. 2,247,531)
dissolved in the plasticlzer the mixture was ap- ' 10
To 5 parts of zein by weight there was added
95 parts of 2-ethyl octanoic acid. After the zein
plied to rayon yarns as a size which provided such
and further to lubricate the yarns during spin
ning operations.
15
-
Then a stiff homogeneous mixture of am
monium rosinate was prepared by thoroughly
mixing for several hoursv at an elevated tempera
ture not in excess of 200° F., 4 parts by weight
(dry basis) of papermaker’s rosin and about 1
20 part by weight of aqua ammonia (26° Be).
mix thus prepared 2 parts by weight of Z-ethyl
.hexanolc acid to act as a plasticizer.
This fatty‘
‘weight of methyl Cellosolve and about 105 parts 25
acid was readily emulsi?ed into the mix. This
by weight of isopropyl'alcohol. The resultant
mix was then employed to clay coat paper by ?rst
homogeneous product was knife-coated onto a
mixing it ‘with a.clay.dispersion. A suitable clay
dispersion was prepared by slurrying together by
weight 400 parts of kaolin, 200 parts of water and
range 170° to 180°
F., for a period of about 2 30 5.5 parts of sodium pyrophosphate. To 3 parts
hours. The resultant material was a dull black
by weight of the clay slurry there was then added
arti?cial leather which was eminently adapted to
embossing operations.
plasticized zein dispersion,
'
Example 12
35
Twenty grams of zeinwere dissolved in 50 ml.
of 95% (by volume) ethyl alcohol and 18 ml. of
excellent qualities as a
paper coater and gave a clay-coated paper of sat
isfactory adhesion and wax-pick test.
The foregoing description and
commercial aqueous formalin (40% by volume),
and the solution was treated in an autoclave at
15 lbs. steam pressure or 121° C., for 1 hour.
40
the solution of prolamine reaction product thus
' 1. A plastic-ized “prolamine-base” composition
?exible clear coat
ings were secured, which if further heated for 3
hours at a temperature'above 130° C., became
. quite water-resistant as well as grease-resistant
and highly ?exible.
of matter comprising alkyi branched-chain
organic fatty acid in which the total number of
carbon atoms in the molecule is in the range
from 4 to 18 inclusive, and “proiamine-base" pro
tein.
.
-
2. A plasticized prolamine composition of mat
Example 13
ter comprising alkyl branched-chain organic fatty
acid in which the total number of carbon atoms
in the molecule is in the range from 4 to 18
inclusive, and zein.
‘
-
.
3. A plasticized prolamine composition of mat
ter comprising alkyl branched-chain organic fatty
' acid in which the total number of carbon atoms
in the molecule is in the range from 4 to ,18
inclusive, and gliadin.
was then introduced into this solution 15 parts
a de-starched, de-oiled corn gluten
4. A plasticized prolamine composition of mat
ter comprising alkyl branched-chain organic fatty I
acid in which the total number of carbon atoms
in the molecule is in‘ the range from.4 to 18
- inclusive, and hordein.
5. A plasticized prolamine composition of mat
.
ture of about 165° F. After being maintained at
a temperature in the general range 160° to 170° 65
atoms in the molecule is in the range from 4 to- 18 _
F., for about 2 hours, the mixture had become a
inclusive, and prola'mine-containing
smooth‘ paste. This was roller-coated onto a
gluten.
cereal
'
piece of cotton
square.
cloth of 80 x 80 ‘threads per inch
' 6. A plasticized “prolamine-base” composition
After drying, a stiffened fabric. exhibit 70
of matter comprising alkyl branched-chain or
ganic fatty acid in which the total number of car
shade/cloth having appropriate stiffness and ?ex
bon atoms in the molecule is in the range from
4 to 18 inclusive, and zein-base protein.
>
ibility for such use, and it evidenced only very
7. A plasticized prolamine composition of mat
slight tendencies to crack upon aging after nu
ing a black ?nish, resulted. This prepared mate- ‘
rlal was eminently suited for use as a window
75 ter consisting of prolamine and alkyl branched
'
2,410,124
11
chain organic fatty acid plasticizer therefor, in
which the total number of carbon atoms in the
fatty acid molecule is in the range from 4 to 18
inclusive.
'
'
8. A plastlcized prolamlne composition of mat
12
14. A composition comprising by weight at least
5 parts of “prolamine-base” protein derived from
corn and from 5 to 95 parts of alkyl branched
chain organic fatty acid in which the total num
ber of carbon atoms in the molecule is in the
ter consisting substantially of zein and alkyl
range from 4 to 18 inclusive.
branched-chain organic fatty acid piasticizer
tion form, “prolamine-base" protein, alkyl
branched-chain organic fatty acid plasticizer
therefor, in which the total number of carbon
atoms in the fatty acid molecule is in the range
from 4 to 18 inclusive.
9. A plasticized prolamine composition of mat
ter consisting substantially of gliadin and alkyl
branched-chain organic fatty acid plasticizer
15. A coating composition comprising in solu
therefor, in which the total number of carbon
atoms in the molecule is in the range from 4 to
18 inclusive, and a mutual solvent for said mate
rials.
-
16. A coating composition comprising in solu
therefor, in which the total number of carbon
tion form "prolamine-base” protein, alkyl
15
atoms in the fatty acid molecule is in the range
branched-chain fatty acid plasticizer therefor
from 4 to 18 inclusive.
in which the total number of carbon atoms in
10. A plasticized prolamine composition of mat
the fatty acid is in the range from 4 to 18 inclu
ter consisting substantially of hordein and alkyl
sive, and a mutual solvent for said materials, there
branched-chain organic fatty acid plasticizer
being ‘by weight at least 5 parts of the said pro
therefor, in which the total number of carbon 20 tein and from 5 to 95 parts of said ‘plasticizer.
atoms in the fatty acid molecule is in the range
17. A coating composition comprising in solution
from 4 to 18 inclusive.
.
m
form "zein-base,” protein, alkyl branched-chain
11. A plasticized prolamine composition of mat
fatty acid plasticizer therefor in which the total
ter consisting substantially of prolami'ne-contain
number of carbon atoms in the fatty acid is in
ing cereal gluten and alkyl branched-chain or 25 the range from 4 to 18 inclusive, and a mutual
ganic fatty acid plasticizer therefor, in which
solvent for said materials, there being by weight
the total number of carbon atoms in the fatty acid
‘ at least 5 parts of the said protein and from 5 to
molecule is in the range from 4 to 18 inclusive.
95 partsv of said plasticizer.
12. A plasticized “prolamine-base” composi
18. A coating composition comprising in solu
tion of matter consisting substantially of "pro 30 tion form zein, alkyl branched-chain fatty acid
‘ lamine-base” protein and alkyl branched-chain
organic fatty acid plasticizer therefor, in which
' plasticizer therefor in which the total number of
carbon atoms in the fatty acid is in the range
from 4 to 18 inclusive, and a mutual solvent for
said materials, there being by weight at least 5
13. A composition comprising by weight at 35 parts of the said zein and from 5 to 95 parts of
the total number of carbon atoms in the fatty acid
molecule is in the‘range from 4 to 18 inclusive.
least 5‘ parts of “prolamine-base” protein and
from 5 to 95 parts of alkyl branched-chain organic
fatty acid in which the total number of carbon
atoms in the‘ molecule is in the range from 4 to w
18 inclusive.
said plasticizer. '
'
WILLARD L. MORGANJ/ '
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