United
‘
2,871,135
Patented Jan. 27, was
2
1
found in the patent one mole of the aluminum-alcoholate '
reacts with one mole of the enalic compound according
to the equation:
2,871,135
METHOD FUR PRODUCING DRYING OILS
AND THE OIL S0 PRQDUCED
OR
Josef Weiss, Vallingby, Sweden, assignor to Richard Nils
{
gon Aktiebolag, Stockholm, Sweden, a corporation of
1'11OOH
"
A—OR+CH
weden
OR
OR
00.0112
No Drawing. Application August 6, 1956
Serial No. 602,439
Claims priority, application Sweden November 7, 1955
(
——-> A—OR
+ROH
("30.131
(11H
10
00.0132
The enolized aluminum-alcoholate then reacts with 2
moles of a fatty acidv thus forming a drying oil the con
6 Claims. (Cl. 106-252)
This invention has for its objects a method for pro 15 stitution of which is explained by the replacement of the
2 moles alcohol by 2 moles fatty acids while the enolic
ducing drying oils and the oil so made.
compound remains in its place bonded to the aluminum
Many methods are known for producing drying oils
via the O-bridge.
and for the improvement of such drying oils.
The mixture of the natural and the synthetic oils is
Apart from the use of metallic driers which only act
carried out either at room temperature or at an elevated
as catalysts during the drying process the object of all
temperature. Mixing may be elfected by agitating or
known methods is not only to accelerate the drying, but
stirring until the components are intimately mixed and
also to improve the ?lm properties of the oil. In all
from a homogenous composition. Driers such as lead-,
known processes this effect is attained by encroaching
on the chemical structure of the glyceride molecule.
few examples of these methods are.
’
A
(l) Producing of standoils by boiling drying oils with
cobalt- and/or manganese salts, and/or pigments, may
25 be added in known manner.
The action of the addition of the synthetic oils, for
instance on linseed oil and other drying natural oils
consists in a considerable acceleration of the drying
(2) Conjugation of the isolated double bonds accord
process of the oils so that the duration of this process
ing to different methods,
(3) Accumulation of glycerides with more unsaturated 30 may be reduced to about 1/5-% of the drying time of
the original drying oils used in the mixture. Thus the
fatty acids by selective extraction or by other methods,
non drying oils will be converted into drying oils having
(4) Transformation of non-drying castor oil into a
shorter drying times than boiled linseed oil. In addi
drying oil with conjugated double bonds,
tion to this advantage, there are also obtained important
(5) Removal of saturated glycerides by a splitting
process, removing the saturated acids and re-esterfying 35 improvements of the ?lm properties. The water and
weather resistance of the oil is considerably improved
the unsaturated acids by means of polyalcohols, etc.
by the addition of said synthetic oil. The ?lms ob
The object of these processes is to achieve one or
tained from linseed oil and other drying oils swell in
several of the following improvements:
water and are spoiled after a few days. The ?lms of
(a) Acceleration of the drying process,
40 expensive isomerized linseed oils are dim already after
(b) Avoiding after-stickiness of the ?lms,
having'been exposed to the in?uence of water for one
(c) Improving the water-and weather resistance, etc.
day. The ?lms produced by oils according to the pres
The methods mentioned require expensive equipments,
ent invention remain clear even after having been ex
a great consumption of energy and chemicals, and they
posed to water for months and they do not swell in
involve very complicated and expensive processes.
It is also known to improve drying oils by mixing 45 water. The pigmentation properties, the adhesion, the
or without the use of vacuum,
them with organic Al-compounds, for instance alumin
?exibility etc. are excellent.
iumalcoholates but these compounds cause a poor sta
The oil composition according to the invention is com
patible with all other raw materials conventionally used
bility of the mixture.
_
The inventor has found, that additional improvements
in producing lacquers and varnishes.
Certain valuable properties of the oils and their ?lms
can be attained by mixing a natural drying or natural 50
can be attained by changing the ratio between the quan
nondrying oil of vegetabilic or animalic origin with
tities of the natural oil and the synthetic oil. Among
a synthetic oil, produced by condensation of one or
these properties which are attained the range of viscosity
more fatty acids with an organicaluminium compound
of the oils which are produced may vary from a low
in enolic form, i. e. a compound in which Al is partly
linked to oxygen of an enolic group, for instance ac
55 viscosity oil like the known natural oils to the viscosity
of standoils. As an entirely new property for drying
oils of this kind can be mentioned, that all ?lms of oils
produced according to the present invention are repel
which became abandoned on or about January 10, 1957,
lent to fungi.
or its continuation-in-part-application Ser. No. 600,729
The following table gives a survey on the possibilities
that was ?led June 30, 1956. The last named patent ap 60
cording to the U. S. patent application of Kurt Hans
Reisinger, Serial No. 258,539 ?led November 27, 1951,
, plication corresponds to British Patent No. 761,536, com
plete speci?cation published November 14, 1956. As
and the most important properties of different oils within
the scope of the invention.
2,871,135
a
a
4i
Drying Time for a
film with a thickness
of 40;;
After
Water-
sticki-
resistance
Yellowing
Attack of
fungi
ness
At 20° 0 ,
ours
At 100° 0.,
hours
Raw Linseed Oil, siccativated ________________ __
very poor _____ ._
Raw Linseed Oil, with synthetic oil
Raw Linseed Oil, with:synthetic oil
Raw Linseed Oil, isomerized
Boiled‘ Linseed Oil _______ __
_
Boiled linseed Oil, with synt
attacks.
llent__
_-
repellent.
D0
attacks.
2-4 days_..
Do.
no ------- --
repellent
Boiled linseed Oil, with synthetic oil and pigment"
Raw Chine Wood Oil:
Raw
Chine
Row
Wood
D0.
I
Oil,
siccativated _ _ _ _ _ _ _ _ _
----~ -- - - - --
Chine Wood Oil, with synthetic oil___.
- - - --_------_- ---------------- -
no _______ __ not investlgated- 110 ------- --
D0.
Raw Soybean Oil:
Raw Soybean Oll,'siccativated ________________ __
_
Raw Soybean Oil, with synthetic oil _________ __
4-
feebIe..."
no _______ ..
Do.
Raw ?goybean Oil, withtsynthetic oil ondpigrv
;
I10 ------------ --d0 --------- -- I10 ------- --
excellent ______ -_
Do.
men .
Raw Herring Oil:
Raw Herring Oil. siccativated ____________ _.
Raw Herring Oil, with synthetic oil ......... ._
D0.
Row lien-inn Oil, with synthetic oiland pigsozlgxol treated Herring Oil (Iodine Number
130.
men .
Solexol treated Herring Oil (Iodine Number
220); siccativated.
non drying
'
SoleIoI treated Herring -Oil (Iodine, Number
220), with synthetic oil._,
6 ________ ..
110 ------- --
D0.
51/§—6;_____ about 1---. I10 ------------ "d0 --------- -- n0 ------- __
1 ________ -_
I10 ------------ “d0 --------- __
D0.
.
Solezol treated Herring Oil (Iodine Number
220), with synthetic oil and pigment.
Raw Cottonseed Oil:
Raw Cottonseed Oil, siccatlvated _________ __
non drying '
Row Cottonseed Oil, with synthetic; Oil _ _
_ _ __ . 8-9 ______ __ 1—.2%-T.___-
Raw Whale Oil:
Raw Whale Oil, siccativated;_Raw -Whale Oil, with synthetic oi _
Raw W'hale Oil, with synthetic oil on
-- ---- feeble -------- --d0 --------- -- n0 ------- __
D0.
14%;"-.- feeble -------- -_d0 --------- -- n0 _______ __
bout.1._._ 110 ------------ --d0 --------- -- 1J0 ....... __
DO.
D0.
rvins
v7 9
The italicized compositions include, according to the invention, a mixture of the respective oil with synthetic oils produced by a
condensation improved properties in all respects.
Examples
(7) 50 kgs. raw whale oil‘are mixed, at room tempera
ture, with 50 kgs. of a synthetic oil, produced bycon
In~the following examples all drying times are meas
densation of the residue fromthe distillation .of ?shoil"
fatty acids with an'organic aluminium compound of the
kind speci?ed above. The drying time of ‘the mixture
ured in-hours for a ?lm of 40p at 20° C., and the viscos
ity is measured in DIN-seconds. The organicalumin
ium compound ‘consists of. an cnolic compound, the: en-.
is 8 hours and the viscosity 70 sec.
olic component of which is i. e.-. aceto-acetic ester; ma 40
(8) >90 kgs.‘ cottonseed oil are mixed, at 40450°' C.,
lonio diethyl ester or acetonylacetom Any of‘ these‘
with 10 kgs. of a synthetic oil, produced by condensa
tion of linseed acid with an organic aluminiun‘i?com‘i
pound of the kind speci?ed above. The dryingltime of
the mixture is 8 hours and the viscosity 100‘scc.
compounds may be used in the ,dilferent‘examplcs.
(1) '75 kgs. boiled- linseed oil are mixed at room
temperature with‘25 kgs. of a synthetic oiliwhich hasbeen
produced by condensation of coconut fatty acids with
(9) 50 kgs. raw herring'oil are mixed at room tem
an organic aluminium compound of the kind speci?ed 45 perature
with 50 kgs. of a synthetic oil, produced'by
above. The drying time of the mixture wasfound to be
condensation of talloil with an organic aluminium corn-'
3%. hours and‘thc viscosity 25 sec.
pound of the kin-d speci?ed above. The drying time
(2); 60 kgs. boiled linseed‘ oil is mixed, at 55° C.,
of the mixture is 71/2 hours and the viscosity 95' sec.
with_,40 ‘kgs. of a synthetic-oil,-.produced by condensa
(10) 60 kgs; raw 'codliver' oil are mixed, at room tem
50
tion of whale oil fatty acids with an organic aluminium
peraturc,'with'40 kgs. of 'a synthetic oil, produced by
compound of the kind speci?ed above. The drying
condensation of take-offs from the distillation of hydro-'
time of the composition is 41/2 hours and the viscosity
genated fatty acids with an organic aluminium com-'
30 sec.
pound of the kind speci?ed above. The drying time
(3) 5O kgs. raw linseed oil areimixed, at room‘ tem
of the mixture is 8 hours and the viscosity 110 sec.
(11) 60 kgs. raw Chinese Wood oil are mixed at room"
perature with SOV-‘kgs. of- a synthetic .oil, produced by
condensation of ,Whale oilfatty acids-With an'organic
aluminium compoundof the kind speci?ed'above. The
drying time of the mixture Was found to be 31/2 hours
and the viscosity-~50 sec.
(4) 60 kgs. raw’linseedoil are mixed,-.at 100° C.',
WithAOfkgS. of a synthetic oil, produced by condensation of-stearic acid with an organic aluminium compound
of the‘ kind speci?ed above. The drying time ‘of the:
60
temperature, with 50 kgs. of a synthetic oil; produced’
by condensation of cottonseed acid with an organic
aluminium compound of the kind speci?ed above. The"
drying time of the mixture is 1/2 hour and .the viscosity‘
160 sec.
(12) 40 kgs. raw Chinese Wood oil are'mixed'at 50°‘ '
C. with 60 kgs. of a synthetic oil, produced by‘ cont"
densation of Whale oil fatty acid with an organic alumin
mixture was 41/2 hours and the viscosity 65 sec;
(5) 75;kgsi. dehydrated castor oil are mixed, at 50'—60° 65 ium compound of the kind speci?ed above‘. The dry
ing time of the mixture is less than 1/2 hour and the
C., with -25 kgs. of a synthetic oil, produced by con
viscosity 230 sec.
densation of herring fatty acids with an organic alumin
In all examples the synthetic oil is producedin the‘~
iumj-compound of the kindlspeci?edz above; The dry
mannerdescribcd in one of theaforesaid U. S. patent
ing;timcof themixture is 31/2’ hours and'the-viscosity
applications Serial No. 258,539 now abandoned-or Serial
200 sec.
_
No. 600,729 and Serial No. 258,539.
(6) 80 kgs. raw soybean oil are mixed, at 75° C.,
I claim:
with 20 kgs. of a synthetic oil, produced by condensa
1. A method of producing improved drying oils com
tion of coconut fatty acid with an organic aluminium
prising the steps of condensing two moles of a fatty
compound of the kind speci?ed above. The drying time
75 acid selected from the group consisting of unsaturated
of the mixture is 41/2 hours and the viscosity 80 sec.
2,871,185
5
higher fatty acids and mixtures of unsaturated higher
fatty acids with one mole of an organic aluminum com
pound in which two valences of the aluminum are bonded
to alcohols while one valence of the aluminum is bonded
to oxygen of an enolic compound selected from the
5. A method as recited in claim 1 wherein pigment
is added to the mixture.
6. A drying oil comprising a mixture of glyceride
of a higher fatty acid and a synthetic oil obtained by
condensing two moles of a fatty acid selected from the
group consisting of acetoacetic ester, malonic diethyl
group consisting of unsaturated higher fatty acids and
ester and acetonyl acetone to form a synthetic oil and
mixtures of unsaturated higher fatty acids with sat
mixing it with a higher fatty acid triglyceride.
urated higher fatty acids with one mole of an aluminum
compound prepared by reacting one mole of aluminum
2. A method as recited in claim 1 wherein said glyc
10 alcoholate and one mole of an enolic compound se
eride is a drying oil.
lected from the group consisting of acetoacetic ester,
3. A method as recited in claim 1 wherein said mix
malonic diethyl ester and acetonyl acetone.
ing is carried out at room temperature.
4. A method as recited in claim 1 wherein a drier
is added to the mixture.
No references cited.