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Патент USA US2410294

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2,410,294
Patented Oct. 29,’ 1946
' UNITED
PATENT “OFFICE
‘ ': helm,‘ , Germany;
vested in the iAlienuiPi-operty _ 1:
Custodian‘:
‘ No‘nr'awiiig; App, cation-February 6;"1941, Serial
No. 377,711.
'
In‘G'ermanTFebruary 8,1940- H: g:
' " '
V 1'3 Claims.
‘.
’
vi1‘ i;
=
‘r’
i“ ‘F’
xi
wd-i
>
.J.
i
The present invention ‘relates to valuable ‘ “ passes over at 1.5 mms. pressure at 180 tov 8,5?l
assay colorless and todourless; oil." iwhichcissndt
softening agents more particularly to those of
miscible withuiivatertv
H
the general formula:
H2C———-CH1
I -~Corresp_ondin_g products are obtained whenlire
H2C———CH1
5, placing the acetic acid; by other aliphaticjacids
" such] as. caproic; caprylic or capric acid
to
.
v
a
‘
A mixture of 228fzpartsrof the alcohol
| -,
Mai
m
V.
wherein R stands for a member of the group con
sisting of a methine ‘radical and the methine
used
‘10 in‘ Example, _1 and 250a parts of benzoic acid an
hydride;
the
esteri'?cation
is usiowiyjiifeated
has ‘, beenmfihished.
atj2oofito 220°,‘
the‘? eact n
radical forming a part, of-‘ai-‘cjyclohexane ringz‘and
product is digested with afdilute ‘sodium carbi
R1 stands for a ‘radical ‘selected frp'rntheialiphatic
.
.
solution-in
order to 'r'emoveathe
formed‘ 10qii'zl'oi'c
and benzene series ~ the essential; characteristic 15 acid._. ,Then the residue is distilled invacuoq ‘ The
of the‘ methine radical being ‘the existenceoi three
esterfthus obtained ofthfe formula; ' ‘ " "
linkages. each'iof whichis satisfied by‘ other sep
‘Him-Leon,
arate alkylene or arylene‘sub'stituentsr ' ’
_ V The'new softeningiagents, are obtained by con
densing two molecular" proportionsofyiuriural
cycloaliphatic ketone?containi'ng reactive alkyl
29
.
>
'
1-
o
'v
_
‘
,
wind-5cm
(‘:0
with one molecularf proportion of an aliphatic or
I
groups, entirely hydrogenating the formed con
densation products and esterifying the secondary
I
alcoholsrthus obtainedrbny means of jcarboxylic
acids of the aliphatic and ‘benzene series or-their
reactive
derivatives._
‘
‘
,
boils at 1 mm.;15iessjii'reatf2oo_ to 721p“ asayiscquvs,
'
The present new ester compounds exhibit an
excellent softening effect on the various thermo
plastic compounds of a highamolecularl weight
and the arti?cial masses-obtained therewith,
such as highly polymerised vinyl compounds,
polyacrylic acid esters and mixed polymerisation
products therefrom, moreover cellulosicderiva
tives.
30 *C““rrespo'ndin‘g‘ estersare obtained'wh'eri‘ steifif
fying with derivatives of benzoic acid‘bei'ngfs v‘b-l
iiiilltei by’ methyl girl“ 191: Helped:
>, or - if; mamas»
4 50 partsjoithealcohol asji‘is‘d
i
by oxidising the higher aicohb‘isiwhich are ‘wen
parts being by weight 1 and all temperatures in
7
known lay-products“ of thelimethanol synthesis.
I
‘Example!
( _ vLe‘gfcregoin'it;
ex" mp1es__ ‘re'lmiie'd with 310 "parts‘gof alfmixliulfe
er'éai-boiiyiic‘ acids ‘of'ac'id mining; 324-, oh?aih'able
presentuin- ‘
In order to furtherillustrate
vention the following examples are given, the
degrees centigrade.
a? ‘i
a) 11153113111‘? isslqvlv-hcaied 15? 209 to 250° While
introducing? nitrogen into the reaction 'yvve'ssel.
,
. ith the nitrogen" which passes- through also
furyl-3-_hydroxypentane" and 6.6 parts oiFa'cetic'
‘acid anhydride isfheated vfor about ~2v hours ‘in’ an
apparatus provided‘ with ‘a? 'r‘e?u
‘
' ‘
condenser.
Then the formediacetic acidis'i re'i'no whac
tional distillation. Subsequently1Iitlie'““reaction
product of'theformulaz
111. 15:;
'1
wateris-jrernovédnw
7'
,
;,
,,
The same estefisobtain .‘accordingi-‘toqthe
45
.
following method: A mixture‘ of equal quantities
of the alcohol and the aforesaid mixturerofv car
boxylic acids-_-is">subiected'lin ‘the-1 presence of
toluene as assistant liquor and a small amount
of benzene sulfonic acid to the aceotropic dis
tillation. ,When the splitting off of water has
been ?nished the reaction product is isolated'as
described in'iExa'mple 2.
ifiieicrmeadmixtiire pfesiarsyboils.
‘pressure ammo
5?? less 011.
240?.v-asa1c0lqr1e ‘am 0d
s '
l -
2,410,294
3
Example 4
4
A similar ester is obtained when using the
phenoxy Propionic acid as esterifying agent.
Example 7
By condensing the alkali metal compound of
glycolmonobutylether with the sodium salt of
monochloroacetic acid there is obtained the di
When esterifying by means of adipic acid the
formed diester of the formula:
.10.
etheracetic’ acid of the formula:
CHr-O-CHz-COOH
‘
v'boiling'at 15 mm. pressure at 163 to 165°.
176 parts of thisacid are mixed with 246 parts
of 1:5-ditetrahydrofuryl-3-hydroxypentane and
the mixture is heated at reduced pressure. With
.an almost theoretical yield the ester of the for
is an odourless oil boiling above swat 151mm.’
pressure.
.
.7
Instead of adipic acid other dicarboxylic acids
such as succinic acid may be used as esterifying 20
agent.
I
,
V
,.
,
‘
,
.
In the manner as described in the Zforegoing
I a,
examples other entirely hydrogenated condensa
(5H:
l
tion products of furfural with suitable lketones
such as methylethylketone, ' diethyl-ketone, cyclo
_ hexanone and its alkylated derivatives such‘as
is obtained as a colorless and odourless oil, which
is not miscible with water and boils at 0.5 mm.
pressure at 215 to 220°.
isooctylcyclohexanone yield valuable products by
esteri?cation.
‘
O-CHrCHr-O-CHn-CHFCHz-CH:
25
‘
The ethercarboxylic acid derived from glycol
monophenylether yields an ester of similar prop
Avmixture of 246.parts of 1.5-ditetrahydrofur—
yl-3-hydroxypentane and 116 parts of isohept
oxyacetic acid is heated for about 6 hours at
erties.
_
,
I
'
‘
Example
8
'
'
300 parts of 2.6-di-trahydr0furfurylmethyl-cy
about 140° ‘in,a vacuo of 20 to 25 mm. pressure,
clohexanol obtainable by hydrogenating the yel
the-formed‘ water distilling 011“. Then the tem
perature is increased during about Ghours to 180° 35 low condensation product of two molecular pro
portions of furfural and one molecular propor-v
and the reaction mixture is held at this tempera
tion of cyclohexanone are mixed with 400 parts of
ture for 12 hours. The formed ester is isolated by
fractionating ‘distillation.
acetic acid anhydride and the mixture is heated
The ‘yield is nearly
theoretical. The ester thus obtained of the for
mula:
under ‘re?ux for about 3 hours. By a fractionat
40
\
I
0
Y
\ /
I
o
45 ' ‘HaC--—.-CH1 '
‘Ha’ \
CH:—Q—-C 1111:
-
_
-
g
n-cm-nc
0
is a colorless and odourless .oil, which is not mis
cible with‘water and boils at 1 mm. pressure at
H10
~
,
Y
H2C——-CH2
CH—ICHz—HC\_ /onl
011,
0
pressure at 190 to 200°.
'
I claim:
'
hols of a lower or higher number of carbon atoms,
1. Asoftening agent of the formula:
such as from a-ethylcyclohexanole or from. the
.mc-om
higher alcohols, which are well known :as by
_
g
,
.
Example 6
_
H,
‘
with water, and exhibits an excellent softening
o
‘i'
. o
e?ect on thermoplastic compounds of high mo
_'
iHlO--'_'CH2
' cn-cmom-on-omonrnc
\'/.r;
.
65
on,
-\_/
‘ 0
-
70
is obtained as a colorless and odourlesso'il, which
‘boils at‘223 to 226° at 0.7 mm. pressure and-is not
miscible with water.
Hz
being a colorless and odourless oil, which boils at
223 to 226° at 0.7 mm. pressure and is not miscible
an almost theoretical yield by fractional distil
lation the formed ester ofathe formula:
v
o
Ame-Q
yl-3-hydroxypentane and 152 parts of p‘henoxy
acetic acid is heated-at reduced pressure. With
? M
HaC-—CH:
'
A mixture of 246 parts of 'LS-ditetrahydrofur
mc-----_cn,
'
HIzQ\ 0 /CH—-CH2CH2—(|3H~—CH2CH2—H
0
productsof the methanol synthesis, very similar
'
‘
OH:
is obtained as a colorless oil boiling at 0.6 mm.
I
When replacing the isoheptoxyacetic acid by
other ether-carboxylic acids derived from alco
estersarelobtained.
"
000125 I '
(‘a 0
210to 215?.
ing distillation with an almost theoretical yield
the formed ‘ester ‘of ‘the formula;
HaC-CH:
H2C-——CHI
H20
n-cmom-cH-cmom-no
H:
‘
' ' ' ’
75
lecular weight and cellulose derivatives.
2.- A softening agent of the formula:
2,410,294
5
6
being a colorless and odourless oil, which boils at
3. Softening agents or the general formula
210 to 215° at 1 mm. pressure and is not miscible
H,Q.__CH,
with water, and exhibits an excellent softening
effect on thermoplastic compounds of high molecular weight and cellulose derivatives. .
H,Q___QH,
__
_
H’(B\ / H CHPCHPCH CHPCHPH \ / H’
5
0
to
°
H:
10
iv
wherein, R’ is selected from the group consisting
of alkyl and aryl.
ERNST KORTEN.
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