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Патент USA US2112556

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Patented Mar. 29, 1938
nEsmous comrzigrl'i‘fggrs AND raocizss
James B. Bullitt, Jr., Swarthmore, and Donald
E. Edgar, Philadelphia, Pa., assignors to E. I.
du Pont de Nemours a; Company, Wilmington,v
DeL, a corporation of Delaware
No Drawing. Application October 9, 1935,
Serial No. 44,270
2 Claims.
p (01.
This invention relates to resinous compositions
and more particularly to a combination of oil or
oil acid modi?ed polyhydric alcohol-polybasic
acid resin and urea-formaldehyde condensation
treatment of the solution of polyhydric alcohol
polybasic acid resin withthe urea-formaldehyde
condensation product is continued, usually at a
temperature of 95° C. to 125° C., until the urea~
formaldehyde condensation product is dissolved
Resinous products obtained from the reaction
of urea and formaldehyde possess certain dis
advantages in' their use as coating compositions
as such, among which may be noted the lack of
or dispersed in the solution.
The following examples are illustrative of
methods which may be used for carrying out the
10 ?exibility.
Example I
Further the resins are sparingly
soluble in the usual organic solvents which intro
ducesv di?iculties in their applications. These
45 parts of a blown linseed oil, '9 parts of 95%
resinous materials, however, possess certain desir- . glycerol and 0.04 part of litharge as an alcoholysis
able properties of being relatively colorless and catalyst were heated with agitation in a suitable
' hardening rapidly under the in?uence of heat. container to a temperature of 220-240“ C. The
Attempts have been made to prepare coating material was held within this temperature range
compositions from resinous materialsobtained until a sample removed therefrom was clear and
from the reaction of urea and aldehydes but with homogeneous and soluble in 2 parts of methyl
apparently little commercial success.. The fatty 'alcohol. 42.5 parts of phthalic anhydride and
20 oil and fatty oil modi?ed polyhydric alcohol
9.9 parts of 95% glycerol were then added and
polybasic acid resins are used as protective and the material maintained at a temperature of
decorative coating compositions quite satisfac
220-225" C. until the product possessed an acid
torily but require longer heat treatments to pro
number of between 50 and 60.
‘,duce satisfactorily hard ?lms than is often prac
1 part of the resinous product thus obtained
was dissolved in 2 parts of monoethyi ether of '
I9 in tical. A combination of the resinous product
obtained from urea and formaldehyde and fatty ethylene glycol. To this was added 1 part of the
oil modi?ed polyhydric alcohol-polybasic acid reaction product of urea and formaldehyde and.
resins has been proposed but this practice has the material heated to 100° C.—_I-5° C. until sub
been limited speci?cally to the use of so-called stantially all of the solid material was in solu
non-drying oil modi?ed polyhydric alcohol
polybasic acid resin because of the di?iculties
encountered whenyattempting to produce com
binations of urea-formaldehyde resinous products
and other fatty oil modi?ed polyhydric alcohol
polybasic acid resins than the non-drying oil
modi?ed resin. Many of the fatty oil modi?ed
ing removed by straining, ?ltering or centrifug
Example II
satisfactorily compatible with the reaction prod
50 parts of a heavy blown cottonseed oil, 10v
parts of 95% glycerine and 0.05 part of sodium
hydroxide were heated with agitation in a suitable
uct of urea and formaldehyde as is evidenced by
the non-homogeneous compositions which are
ing within this ‘temperature range was continued
until a sample drawn from the material was clear
polyhydric alcohol-polybasic acid resins are not
This invention has as an object the manufac
ture of. new and useful resinous compositions com
prising a combination of the reaction product of
urea and formaldehyde with fatty oil modi?ed
polyhydric alcohol-polybasic acid ‘resins. A fur
> ther object is the provision of a process for pre
paring these resinous compositions which is suc—
cessfully and advantageously used with the dry
50 ing and semi-drying oils as well as with the non
drying oils. Other" objects will appear herein
tion. The material was then allowed to cool 30
and any slight amount of solid material remain
container to a temperature of 220-240° C. Heat
and homogeneous and soluble in 2 parts of meth
yl alcohol. To this-was then added 38.6 parts of
phthalic anhydride, 7.2 parts of 95% glycerol and
the heating continued at 220—é225° C. until. the 45
material possessed an acid number of between 30
and 40.
1 part of the resinous product thus obtained
was dissolved in 2 parts of butyl alcohol. To this
was then added one part of the reaction product 50
of urea and formaldehyde and the mixture heat
ed at 100° C.‘:5° C. until substantially all of the
These objects are accomplished according to
solid material was in solution. Any'undissolved
the present invention by preparing the fatty oil
modi?ed polyhydric alcoholrpolycarboxylic- acid
material may be removed by straining, ?ltering
or centrifuging.
resin with oils which have been subjected to an
' The resulting resinous combination when ap
oxidizing treatment as ‘by blowing with air, and
then heating this resin in solution with urea
plied as prqtective coating produces a hard, tough
and durable ?lm after vbaking, for example, for
formaldehyde condensation product. The‘heat z'o'mmutesat 100° 0.
lose dispersions to produce lacquers Such lac
quers may contain, in addition, other lacquer in
Example III
45 parts oi blown soya bean oil, Qparts of 95%
gredients as‘soi'teners, ‘plasticizers, other natural
or synthetic resins, pigments, ?llers, dyes, etc. _
The enamels prepared from the resinous com-,
a suitable container to 220-240’ C. until a sample
' of the material was clear and homogeneous and
bination may be applied to'suitable surfaces by
soluble in 2 parts of methyl alcohol. 42.5 parts of
well known means as for example swaying,
phthalic anhydride and 9.9 parts of 95% glycerol. brushing. dipping, etc. If desired the coatings
were then added and the heating continued at
220-225? C. until the material possessed an acid
number of 601-5.
erably dried by subjecting for a short period 0!
air drying if desired and then baking at elevated
temperature oi’, for example, 220'’ l". for a period
oi’ 30 minutes after which treatment a hard,
tough and durable ?lm is formed. The coating
1 part .01’ the resinous product thus obtained
glycol.- Tothiswas addedlpartoithereaction
product of ,urea and formaldehyde and the mix
may be baked at a lower temperature of between 15
ture heated at 100° 0.15’ C. until the solid mate- . 140-150’ 1". with a corresponding increase in time
rialwassubstantiallyalldissolved, Anysmall
or_ at a higher temperature, for example, 300°
amoimt oi’- undissolved material may be removed
by suitable means.
In place oi’ the reaction product of urea and
20 anvaldehydethe reaction product of thiourea and ,
an aldehydemaybe combined with theblownoil
or oil acid modi?ed polyhydric alcohol-polybasic
acid resins.
1''. with a corresponding decrease in time.
The products of the present invention are use
ful in preparing coating compositions for pro 20
tective and decorative purposes on various types
of surfaces such as wood, metal, glass, etc. either
pigmented or non-pigmented. The products
Thereaction' product 01' urea‘and - may be further used in- combination with cellu
formaldehyde for‘ example may include methylol
urea, dimethylol urea, methylene urea, a mixture
of ,these or polymerisation products thereot.
The term reaction-product of urea and i'ormalde
hyde for the present purpose, therefore, em
braces any or all products which may be pre
pared according to the well known
according "to procedures well known in the art
of treating oils and the acids derived therefrom.
Fbr example, a typical procedure consists in heat
lose derivatives as the esters or ethers to pro
duce various types oi" lacquers. Other uses for
the products because of the very desirable prop
erties possessed by them will readily suggest
As will be seen from the foregoing description,
we have disclosed a new method for producing
improved combinations oi’ the fatty 'oil- modi?ed
polyhydric alcohol-polybasic
.. urea-aldehyde
compositions described herein produce coating
compositions yielding hard, tough and water re
mately mil-220° F. and while maintaining tem- ' sistant ?lms. These resinous compositionsare
peraturepassingairthroughthebodyoithe oil.
further advantageous in that the enamel com
This operation‘ is commonly known as blowing positions made therefrom can be converted into
the oil. The air is passed throughqthe oil: hard, ‘tough and durable protective coatings by 40
until the. desired properties with ‘respect , to, baking at relatively low temperatures.
for example, reduced iodine value and increased
As'many apparently widely
viscosity are obtained. Blown oils are well known menis of thisinvention may
and the production of oils having particular 9 parting from the spirit and scope thereoikit isto
properties will be readily apparent to those skilled
beuhderstoodthatwedonotlimitoi'ii's'elvestov @
in the art of preparing such oils.
thespeci?c embodiments thereof except as de
The examples note the use 01’ blown linseed and _ ?ned in the appended claims.‘ '
blown cottonseed and blown soya bean oil as
the modi?ers for the polyhydric alcohol-polybasic
acidresins. Otberblownoilsmayhoweverbe
used satisfactorily as for example perilla oil,
castor oil, China-wood oil, etc., as well as any 01'. ,
theblownoilsintheclassoidryingand semi
drying oils.
Instead of the solvents mention’ed'in the ex
amples,‘we may use various other solvents such
as propyl, isopropyl, and isobutyl alcohols; sec
ondary- alcohols, such as secondary butyl, amyl
and hexyl alcohols; and the aromatic alcohols
such as benzyl, cyclohexyl‘ alcohols, etc. The
choice of solvent will depend to some extent upon
the solvent contents‘ desired in the ?nished _
resinous composition and upon the availability
We claim:
1. A process for making compatible composi—
tions of urea-formaldehyde condensation prod
not and polyhydric alcohol-polybasic acid resin
modi?edwithai'attyoil ottheclassoonsis?ngof
drying and semi-drying oils. said process com5
prising ,i'orming said polyhydric .alcohol-poly
basicacidresinbyreactingpolybasic acid'with
the product obtained by heat treating in the pres;
ence of an alcoholysis catalyst polyhydric alcohol
and an oxidised oil or said class which is obtain-'
able by blowing the ‘oil and
it 180-200‘
F., and heating a solution or the polyhydric alco-'
hol-polybasic acid resin thus obtained with-the
urea-formaldehyde reaction product.
2. A compatible resinous compodtion obtained
of the material.
heating in solution urea-formaldehydejcon
The resin compositionsdescribed above may be densation product and the resinous reaction
used as unpigmented coatings‘or there may be product
of polybasic acid with the product ob-'
incorporated therewith pigments to - produce
tained by heating polyhydric alcohol and anoxi
colored coating compositions or enamels. Fillers
fatty oil which is selected fromthe class
may also be used with pigments if desired. The dized
choice of pigments and ?llers will be readily consisting of drying and semi-,drylng oils and
which isqbtainable by heating the oil at 160-200'
70 understood by those skilled in the art or pre
paring pigmented resinous coating compositions. F. while blowing air‘ therethrough.
The resin solutions may be used with cellulose
derivative combinations, for example, nitrocellu
JAMES B. auxin-r, 'Ja.
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