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Патент USA US2410788

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Patented Nov. 5, 1946
2,410,788
UNITED STATES PATENT OFFICE :
2,410,788
FATTY AMIDE POLYMERS
Willard L. Morgan, Columbus, Ohio, and Earle D.
McLeod, Rumford, R. I., assignors to Arnold,
Hoffman & Co. Incorporated, Providence, R. 1.,
a corporation of Rhode Island
No Drawing. Application April 5, 1944,
Serial No. 529,687
16 Claims. (Cl. 260-22)
This application is a continuation in part of
our copending application Serial #357,443, ?led
September 19, 1940.
This invention relates to new condensation
2
.
have been ?nished with these materials have
frequently during a few months‘storage become
. seriously yellow due to the softener being sensi
tive to oxidation.
Many resinous materials have also been applied
modi?cation of the properties of textile ?bers.
to textiles for various types of modi?cations of
Many materials have been used as textile
their properties. Among these we ?nd the alkyds,
assistants for altering the softness, the easy wet
fatty alkyds, methacrylates, and vinyls which, due 7
ting or the repellency of textile ?bers, or for
to their general water insolubility and sticky na
increasing the stiffness or apparent weight, but 10 ture, cause ‘considerable’ difliculty as they must be
each has been subject to some fault; thus, tallows,
applied in the form of dispersions which are gen
oils, and sulfonated oils or tallows have long been
erally unstable. These materials leave much to
used in the ?nishing of textiles for softening ef
> be desired in their permanency on cloth due to
products which are suitable as assistants for the
fects, but these effects are not permanent and are
alteration on ageing and poor resistance to wash
lost the ?rst time the goods are washed. These 15 ing particularly in the case of the alkyds. Urea
materials also suffer from rancidity or objection
formaldehyde resins have also been widely applied
able odor development in the goods. Fatty
but these frequently impart odors to the cloth “
alcohols and fatty alkyd resins have also been
or tender it and the special high temperatures
used as textile softeners, but these also wash out.
necessary for its baking call for expensive equip
Fatty amides and the quaternary salts of these, 20 ment.
‘
as well as fatty quatemaries produced from
It is an object of this invention to provide a new
pyridine or the betaines, and fatty imidazoles,
class of textile assistants such as wetting, soften
have been suggested as textile modifying agents
ing, lubricating, waterproo?ng, ‘ and stiffening
and in particular as textile softeners. While
agents having improved properties. It is a further
these materials are mostly fairly expensive and 25 object to produce textile assistants which are
' dark in color, these substances have shown the
resistant to heat and to oxidation which permit
advantage of being somewhat resistant to wash
the ?nishing and storage of the ?nished goods for
ing. The quaternary salts of fatty acid conden
long periods without any yellowing, odor develop
sations with aliphatic polyamines have also been
ment, or tendering.
used, particularly as these have shown a maxi 30 As further objects of our invention, we de
mum resistance to washing up to this time. How
scribe condensation products which may be easily
ever, each of these types of materials has left
applied from aqueous solutions or dispersions to
considerable to be desired with regards to re
1_ give ?nishes on cloth of a maximum softness,
sistance to washing and as each of these materials
which effects are completely permanent to Wash
has been unstable with respect to heat and oxida- 35 ing and to dry cleaning.
tion, their use has been attended with the serious
A further object of our invention is to provide
di?iculty of the cloth being yellowed either by
condensation products of resinous nature which
reason of the initially dark color of the product,
givev permanent bodying or stiffness effects cou
or by its decomposition clue to the heat used in
pled with desirable soft feel. These materials, be
drying the fabric. Furthermore, goods which 40 cause of high 'e?ectiveness,.ca,n be economically
2,410,788
-
used to replace sulfonated tallows in textile
finishing.
A still further object of our invention_is to
describe new condensation products and resinous
materials which may be applied permanently to
textile materials from aqueous solution without
any special heating or baking of the treated cloth.
The condensation products proposed by this
4
In this formula just given for the side chains
of the polyamino acid amide type, R1 corresponds
preferably to a saturated aliphatic chain such as
would result from the use of a saturated fatty
acid or any of the other various types of acids
already enumerated; thus, R1 may also represent
other hydrocarbon radicals such as a cyclo alkyl,
an unsaturated hydrocarbon, an aryl radical, or
a residue from a terpene acid. In each case the
invention are resinous or semi-resinous materials
in which dialkylol substituted carbamido com 10 .corresponding acid, acid chloride, or ester may be
used as a source to introduce this radical into
pounds carrying side chains containing polyamino
our condensation products as will be shown later.
acid amide radicals are linked together by reac
The letters 6 and m represent small integers,
tion with polybasic acids.
with e varying from 0 to 4 and m from 2 to 3,
These compounds are readily prepared by re
acting the carbamyl derivatives such as urea, 15 and any of the hydrogen in the CH2 group may be
substituted by a simple alkyl or hydroxy group.
thiourea, guanidine salts, biuret, diguanidine, or
It is evident from the two general formulas
guanyl urea with the acid amide condensation
products, secured from aliphatic polyamines
above that .the alkylol polyamine employed in
producing the product has the following general
carrying hydroxyl groups and acids or acid esters
or acid chlorides and thereafter reacting the prod 20
ucts thus secured with polycarboxylic acids.
formula:
-
-
As suitable: acids for forming the polyamino ‘
acid amides with the polyamines, we prefer those
containing six ormore carbons and preferably
saturated-aliphatic acids such as lauric, stearic,
palm oil acids, although we may use the lower
molecular weight aliphatic acids including acetic
and we may use the unsaturated or substituted
fatty acids, such as ricinoleic, oleic, sebacic or
chlorostearic,>or the cycloaliphatic, aromatic, or
resin acids may'also be used, such as naphthenic,
phthalic, benzolc, creosotinic, and al'bietic, or the
resin acid secured from rosin and maleic an
hydride. These acids may be condensed with any '
in which X represents a simple alkylene group of
from 2 to 3 carbon atoms and in which one of the
hydrogens attached to one of the carbon atoms is
replaced by hydroxyl and in which formula the
integer e varies from 0 to 4 and m from 2 to 3.
The condensation products of this invention
are in some cases directly water soluble or water
dispersible. In most cases the condensations are
readily dissolved after treatment with acids, such
as acetic, lactic, boric, oxalic,vbenzoic, salicylic,
furoic, citric, tartaric, formic, phthalic, succinic,
alkyl naphthalene sulphonic acids or after re
hydroxyl substituted polyamines such as hy 85 or
action with an alkylating agent, such as, ethyl
droxyethyl ethylene diamine, hydroxyethyl
chloride, benzyl chloride, ethylene oxide, ethylene
diethylene triamine, diamino propanols, such as
chlorohydrin, diethyl sulphate, or dimethyl sul
1-3 diamino propanols, N-3 amino .2 propanol
phate. The salts or alkylated products of our
ethylene diamine, or the allwlol substituted
substituted
new condensates are indicated in the
polyamines which are readily secured from
general ' formula given where B represents the
ethylene or propylene oxide by reaction with
polyamines. The polyamino acid amide products
thus secured are reacted with the carbamyl de
acid hydrogen or alkyl groups and X the acid
radical or halogen group, while for our primary
‘ condensations B and X disappear from the for
rivatives already indicated and thereafter the free
hydroxyl groups-are then reacted with polybasic 45 mula.
The condensation products of this invention
acids such as succinic, maleic, sebacic, phthalic,
are readily prepared by heating equimolal quan
and adipic.
titles of the acid and hydroxylated amine at tem
The condensation-products of ,this invention‘
peratures from 130 to 200° C. until the reaction
are materials of high molecular weight in which 50 is complete as shown by the loss of one molecule
units of the following general formula are linked
of water. The mix is then cooled back to 180°
together at the dotted line in large numbers: ‘
and one-half mol or more of the urea or other
carbamyl derivative added. Ammonia is rapidly
liberated as the urea becomes substituted, the
5: temperature being held between 170 and200° C.
After holding the product for a short period up to
p In this formula R1 is a hydrocarbon residue re- I
one-half hour during which time the ammonia is
sulting from the dicarboxylic acid which has been
driven 011,‘ preferably one mol of the polycar
boxylic acid is added at temperatures above 150°
R: and R4 represent simple alkylene groups of 59 C. and the temperature is rapidly raised to 200°- C.
from twotzo three carbon atoms. These groups
as the polybasic acid reacts and wateris lib
and the adjacent nitrogen originate from the
' erated. Depending upon the number of hydroxyl
amine used in the condensation and attached to
groups present in the primary condensation, we
the carbons R: and R4 is the ‘remaining part of
the fatty
i o a01d amide as a side (mam. The
may increase the molal proportions of the poly
basic acid used in order that allor part of these
fatty acid precondensed with the amine forms
may-be reacted with the polybasic acid. The
the terminal part of the side chain. The amino
product may be cooled, and used directly or at
acid amide side chains residues are-of the fol
temperatures of so .to 140° C. the various solu
lowing type in which the radicals may depend for
bilizing acid or alkylating agents may be added
their nature on the amine and the acid reacted 70 in quantities of .2 to .5 mol or more.
The linking by ureaor other carbamyl com
pounds of two or more acid polyamine amide
groups which are thereafter linked into long con
used.
therewith.
<
'
‘
g
"
tinuous resin-like chains results in products of
75 very large molecular weight which are found tov
2,410,788
6
show high substantivi-ty to the various textile
'
-
'
fatty amides or fatty ethanol amides and we ?nd
?bers, such as, cotton, viscose, cellulose acetate,
linen, jute, wool, nylon, and protein ?bers and to
that it is only when we use the amide of an acid
and & polyamine containing either or both a pri
or secondary amino group that reaction to
washing and dry cleaning. This marked sub 5 mary
our substituted ureas can be secured. The con~
stantivit'y is found to arise from the presence of
densations go readily and are free of side reac
the urea or other similar carbamyl groups and
tions, thus,.leading to full yields of products which
particularly to the very high molecular weight
do not need to be puri?ed.
of the products secured by the polymeric chains
In view of the fact that polyamino acid amides
. formed by the polybasic acid linkages. The urea 10 change rapidly at elevated temperatures and that
group also increases the solubility in water which
urea compounds are relatively unstable, it could
is very important since such large molecules
not be ‘foreseen that the polyamino acid amide
which are desirable for substantivity are poorly
substituted carbamyl compounds could be heated.
soluble. Watersolubility is, also brought about
to the high temperatureinecessary for reaction or
by the formation of salts at the nitrogen groups.
that in view of their large molecular size they
We have found that the sensitiveness to oxida
would react further with polybasic acids. How
tion and to heat or light of the acid polyamine
ever, we have found that these reactions can be
amide condensations and other proposed nitro
carried out smoothly with theoretical yields giv-.
gen containing textile assistants which results in
ing products which need no further puri?cation.
yellowing either in processing, drying, storage, 20 The production of resinous like materials indi
or'use of the treated fabrics is mainly caused by
cates the formation of long polymeric chains
the presence of primary amino or —NH2 groups
which due to equimolar quantities of polybasic
in the compounds and to a much lesser extent by
acids used have one hydroxyl and one carboxyl
secondary amino —(NH)— groups. It is the
end group between which lie one or more repeat
primary amino group left in the acid polyamine 25 ing units as set forth in the aforementioned
amide condensations which is reacted upon by the
general formula. By reason of the resinous na
urea or other carbamyl compound and removed
ture of the products, many of these when applied
during the formation of our new reaction prod
to cloth show de?nite stiffening effects and the
ucts, and we are thus able to secure compounds
effects become permanently attached to the var
free of these diihculties. Likewise, the urea and 30 ious textile ?bers. As we have already indicated,
other carbamyl compounds will react with and
despite the large molecular weight of these com
eliminate secondary amino groups and the yel
pounds, the solubilizing groupspresent permit _
lowing arising from such groups and it is an
us to apply these in aqueous solutions or disper
alternative under this invention to use su?icient
sions and the materials become permanently ?xed
urea or other carbamyl compound to combine 35 to the textile ?bers by their substantivity on the
with all the primary and secondary amino groups
same, thus not requiring any special curing or
in the acid polyamine amide, as well as mere
baking beyond the normal drying to develop
ly the single groups as shown in the general for
stiffening and other effects. Where the side
mula already given. The resistance to scorching.
chains contain large fatty groups, various degrees
under heat is also found .to be lowered to some 40 of soft feel are permanently secured along with
degree by the use of unsaturated acids as the
the stiffness or bodylng effects. _
source of R1 and while we may usethem in many
The invention will be further illustrated, but is
types of application, for products of maximum
not limited by the following examples in which
resistance we prefer the use of the saturated fatty
the quantities are stated in parts by weight:
give textile treatments which are permanent to
acids.
'
Inasmuch as urea, thiourea, and guanidine are
I each decomposed readily at temperatures below
45
Example 1
568 parts (2 mols) of stearic acid were heated
with 133 parts of N-3 amino-2 propanol ethylene
diamine until 1 mol of water was collected after
50 which 30 parts (‘/2 mol) of urea was slowly added
at; 180-185° C. and the temperature raised to
190° C. during which time ammonia was evolved.
At 190° C. 101 parts (1 mol equivalent) of sebacic
180° C. or the reaction temperatures employed, it
was impossible to foresee that the large molecule
substituted urea condensations would be stable
at these temperatures or could be formed. Thus,
the heating of’ urea and fatty acids at 160° does
not lead to substituted ureas, but decompositions
occur yielding only fatty amides as shown in U. S.
acid were slowly added and the temperature raised
1,989,968 and U. S. 2,109,941. In a similar way 55 to 200° C. while water was distilled off. The prod
we have been unable to react urea with simple
uct had the following unit formula:
H,
11111
(‘1:0
H:
H:
NH
"His I
H3
H:
NH
JJuHu
H3
NH ‘
=0
2,410,788
.
7
.
.
The acetate salt of this condensate when ap
plied to cotton fabric in the ratio of 6 parts in 50
gallons, gave a permanent ?nish resistant to
washing and dry cleaning. The fabric possessed
180° C. and the temperature gradually raised to
190°C. during which time ammonia was liberated.
1142 parts (1 mol) of the above condensate hav
ing the formula:
H:
H
was heated to 190° C. at which point 202 parts
20 (1 mol) of sebacic acid was added and the tem
Example 2
perature raised to 200° C. during whichtime wa
ter was split off. The product obtained was res
90 parts (1 moi) of 143 diamine isopropanol
increased weight with some stillness.
were heated with 284 parts (1 mol) of stearic
acid until one moi of water was driven oil. 30
inous in nature and water soluble when treated
' with acids or alkyiating agents.
Its formula con
parts (‘/2 mol) of urea were then slowly added 25 sisted of repeating unitsasfollowsz
HI
’
NH
‘
Hg
NH
Hg
JlHg
H:
/
NE
H1
NH
H:
H:
H:
15!
its
Ha
'
E:
H:
H:
11TH
H:
HI
NH
(‘3H1
JJH:
H
NH
=0
"Hat
1
a?g' I
=0
‘(lJUHu
Example 4
at 180485“ C. and the temperature'raised to 190°
C. during which'time ammonia was evolved. At
282 parts (1 mol) of oleic acid was heated with
190° C. 101 parts (1 mol equivalent) of sebacic
204 parts (1 mol) of 1 amino 3 dipropylene tri
acid was slowly added and the temperature raised
amine isopropanol until one moi of water was
to 200° 'C. The product was a sticky resin which 55 driven oil. At 180° C. 30 parts (‘/2 mol) of urea
was slowly added and the temperature gradually
was soluble in water after treatment with acetic
increased to 190° C. during which time ammonia
acid and had the following formula:
H:
2513
'
H:
v 11111
"Bu
nHu
Example 3
284 parts (1 mol) of stearic acid was heated
was evolved. To the above condensate at 190°
C., 74 parts (1 moi equivalent) phthalic anhy
dride was added and the temperature raised to
pentamine isopropanol until one mol of water was 70 200° C. during which time water was removed.
The product obtained was soluble'in water after
i evolved.’ 30 parts (% moi) of urea was added at
‘ with 262 parts (1 mol) of 1 amino 3 tetraethylene
2,410,788
10
treatment with acids or aikylating agents and
had the following‘ unit formula:
’
°
°
. /-O—CE—CH;—NH—P1—NK—CHg-CH-O-g
50 gallons vor water possessed a soft handle with‘
considerable increased weight noticeable which‘
0 tL/
was resistant to washing and dry cleaning proc
I
H,
I'm
11m
'
5
esses.
'
(gm
_
$3‘,
m with 204 parts (1 mol) 01' 1 amino 3 dipropylene
.
NH
(lira
tn.
driven 011'. At 180° C. 30 parts We mol) of urea
EH
was added and the temperature gradually raised
I
'
$3,
H:
It};
11m
JJ=0
(5:0
-
.
triamine isopropanol until one moi of water was
|H’
Hi
Hi
_
'
284 parts (1 mol) of stearic acid was heated
é
-
Example 6
.
(1m,
NH“
v
NH
(gm
In’
4
A
to 190° C. during which time ammonia was
l5 evolved. To the above condensate ‘at 190s c. 73
parts (1 mol equivalent) of adipic acid was added
and the temperature raised to 200° 0. during
"Ha
-
which time water was liberated. The condensate
v
20 obtained was water soluble atter'treatment with
Example 5
90 parts (1 mop of 1-3 diammo lsopropanol
acids or alkylating agents and had the following
unit formula after treatment with dimethyl sul
was heated with 200 parts (1 mol) of lauric acid
fate.
Ha
Ha
I'm
NH
H,
éH:
Ha
Ha
+HI -
+3:
NH
NH
HI
H
'
HI
H:
\rgr-soicm
cm/ =0
6H1
iHs
H:
gin
J7=
“Hid
"Ha
until one mol of water was driven oil. 30 parts
Equimolal quantities oi.’ linoleic, ricinoleic or soya
(‘/2 mol) of urea was then added at 180-185° C. 45 bean fatty acids maybe substituted for the stearic
and the temperature raised to 190° C. during
acid illustrated above
which time ammonia was evolved. ‘At 190° C.
Example 7
1071/2 parts (1 mol equivalent) of petrex acid,
‘
a polybasic acid which is de?ned by its producer
90 parts (1 moi) of 1-3 diamine isopropanol
Hercules Powder (20., as 3-isopropy1-6-methyl- 50 were heated with 284 parts (1 mol) of stearic acid
3,6-endoethylene A4 tetra hydro phthalic anhyuntil one mol of water was driven oil’. 30 parts
dride, was slowly added and the temperature
(1/2 mol) of urea was then slowly added at 180—
raised to 200° C. The condensate was a sticky
185° C. and the temperature raised to 190° C. dur
resin soluble in water after treatment with acetic
ing which time ammonia was evolved. At 190°
acid.- Its acetate salt had the following repeating 55 C. '74 parts (1 mol equivalent) of phthalic an
unit formula:
hydride was slowly added and the temperature
0'
o ‘
-/—O—CH-OHe—NH—-g—NH-—OHs—CH——O—p}
0
H1
onr-g-o-ili-n
‘
H]
11m 0
‘
“ERIE? °E
‘5:0
=0
o
- 1L- /
(gnHu
OH:
H‘
"Ha
Rayon fabric impregnated with a solution of the
above acetate salt in the ratio of 3 pounds per
raised to 200° C; The condensate was a waxy
solid, resinous innature and soluble in water after
2,410,788
_
,
12
treatment,- with acetic acid.
It had the follow-
ing unit formula:
'
1
i
_CH _NH_C_NH_CH
0 CH
1
_
-
60 parts (1 mol) of acetic acid was heated with
‘I
_ _ _
Example 10
l)
CH_O_
104 parts (1 mol) of 1,3 diamino 2 methylol Dro
_ ,_
pane to 180° C. until one mol of water was driven
'-
5 on,
At 180° 0. 30 parts we mol) of urea was
‘H’
In‘
slowly added and the temperature raised to 190° .
NE
(L10
NH
=0
C. during which time ammonia was evolved. To
one mol of the above condensate at 190° C. was
"H"
'
"Ha
-
10 added 118 parts (1 mol) of succinic acid and the
temperature raised to 200° (1., water being re
Cotton fabric impregnated with a bath containing 5 pounds to 50 gallons of the above com-
moved. The condensate obtained was resinous
innature and had the following unit formula:
H!
H!
NH
-
'
NH
HI
H:
pound in the form of its acetate salt possessed
Example 11
8' resinous type hand which was resistant to wash‘
282 parts (1 mol) of oleic acid was heated with
mg amid“ cleaning “mums0. 204 parts (1 mol) of 1 amino 3 dipropylene tri
Example 8
.
“' amine isopropanol until one mol of water was
driven off. At 180° C. 90 parts (1% mol) of
90 parts (1v mol)
of 1-3 diamine isopropanol
were heated with 284 parts (1 mol) of stearie
urea was slowly added and the temperature in
creased to 1900 Q during which time ammonia
acid until one moi of water was driven off. 30
0
parts (‘A mol) of urea was then slowly added at ‘10 was evolved- To the above C(mdensate at 190
o
o ' C. '74 parts (1 mol equivalent) of phthalic an-'
god 18.5 cémcg ‘ghee amgaggfglzals'agz‘ivg_ 92‘;
hydride was added and the temperature raised
190° C. '73 parts (1 mol equivalent) of adipic acid .
to 200° C. during which time water was removed.
.
_
an
(em
1
.
was slowly added and the temperature raised to
Ihe condensate Dbtamed was water soluble after
200. C_ The condensate was a sticky resin SOL 35 treatment with acids or alkylating agents and
uble in water after treatment with acids or 2.1had the following “mt formula:
kylating agents. It had the following unit for-
'0
mula:
o
"
o
o
40
H,
.1w-onmm-Nn-ii-m-cm-On-o-ii-m??i;.
m
15:.
'
?n
-
‘5:
_ “h
"Ha
4m,
o
45
7
8m
$5,
282 parts (1 mol) of oleic acid was heated with
104 parts (1 mol) 01' 1,3 diamino 2 methylol pro- 50
pane to 180° C. during which time one mol of
water was obtained. .At 180° C. 30 parts (‘A mol)
(‘1H1
(‘2a,
1!;
,.
.
-
(EH,
0
a
m
1!;
H
_
Am,
.
(EB
l a
NE
A
H:
(5:0
J1=o
H
w A H
‘7 "
‘
|
NE
of urea was slowly added and the temperature
To one mol of the above condensate 5,.
y
(BB,
raised to 190° C. during which time ammonia was
evolved.
g-l -
K,
(EH:
o
Anna
Example 9
0 '0
-l--O—CH-CHg-NH-Pl-NE-Clh-GH-O-g
" "
98 parts (1 mol) of maleic anhydride was added " As many apparently widely di?erent embodi
and the temperature raised to 200° (3., water bements of this invention may be ‘made without
ing removed. The condensate obtained was 501departing from ‘the spirit and scope thereof, it
uble in water after treatment with acids or ai-
is understood that we do not limit ourselves to *
kylating agents and had the following unit for- 60 the speci?c embodiments thereof except as de
mula:
'
"Ha
fined in the appended claims.
“Ha
2,410,788
We claim:
13
.
Y
14
I
' 8. A process for forming a condensation prod
uct as de?ned in claim 1 in which equimolar quan- ~
1. A condensation product having one hydroxyl
and one carboxyl end group and consisting of
titles 01' an organic monocarboxylic acid andqan
repeatingi units of the following general formula:
alkylol polyamine of the following generalfor
‘
wherein R1 is a hydrocarbon residue resulting
mula
in which X represents a simple alkylene group
from a polycarboxylic acid and in which R3 and
of from 2 to 3 carbon atoms andin which one
R4 represent simple alkylene groups of from 2 to m of
the hydrogens attached to one of the carbon
3 carbon atoms and in which there is attached
to one of the carbons in R: and R4 acid amide
atoms is replaced by hydroxyl and in which for
mula the integer e varies from 0 to 4 and m from
2 to 3 are condensed at temperatures between
side chains of the following general formula:
15 130—170° C. and thereafter reacted with one-half I
mol of urea at 170-200° C. and thereafter reacted
with equimolar quantities of a polycarboxylic acid
at temperatures from 150-200° C.
in which R1 represents a hydrocarbon radical re
sulting from an organic acid and in which the
9. A process for forming a condensation prod- '
letters e and m represent small integers with e
uct as defined in claim 1 in which equimolar
varying from 0 to 4 and m from 2 to 3.
20 quantities of an organic monocarboxylic acid and
2. The salt of an acid with a ‘condensation com
an alkylol polyamine of the following’ general
pound described by the general formula in
claim 1.
formula
~
'
3. The alkylated product of the condensate de
scribed in claim 1 obtained by alkylating with a 25
in which X represents a simple alkylene group
compound selected from the group consisting of
of from 2 to 3 carbon atoms and in which one
ethyl chloride, ethylene oxide, benzyl chloride, di
of the hydrogens attached to one of the carbon
ethyl sulfate and dimethyl sulfate.
atoms‘ is replaced by hydroxyl and in which for
4. The condensation products having one hy
droxyl and one carboxyl end group and con
sisting of repeating units of the following gen
30 mula the integer e varies from 0 to 4 and m from
2 to 3 are condensed at temperatures between
130-170“ C. and thereafter reacted with onerhalf
eral formula:
mol of urea at 170-200“ C. and thereafter further
reacted with su?lcient polycarboxylic acid to re
35 act with all of the hydroxyl groups present.
10. A process for forming a condensation prod
uct as‘ de?ned in claim 1 in which equimolar
quantities of an organic monocarboxylic acid and
an alkylol polyamine of the following general
wherein n ranges from 1 toul'? and R1 is the hy
drocarbon residue from a dicarboxylic acid.
5. A new chemical compound having one hy
droxyl and one carboxyl end group and consist
40
formula
.
'NHa-rwmm-mmP-cm-x-Nm
in which X represents a simple alkylene group
of from 2 to 3 carbon atoms and in which one
ing of repeating units of the following formula: 45 of the hydrogens attached to one of the carbon
Hg
NE
"Ha
H!
NH
"Has
6. A new chemical compound having one hy— 55 atoms is replaced by hydroxyl and in which for
droxyl and one carboxyl end group and consist
mula the integer e varies from 0 to 4 and m from
ing of repeating units of the following formula:
2 to 3 are condensed at temperatures between
130-1'70° C. and thereafter reacted’with one-half
mol of urea at temperatures between 170°—200° C.
H,
- NH
=0
"H"
H, p
60 and thereafter further reacted with an equimolar
1113
=0
"H"
quantity of a polycarboxylic acid at temperatures
from 150—200° C. and thereafter solubiiized by
adding one mol of acid.
.I_ A new chemical compound having one hy_ 65
and one carboxyl end group and consisting of repeating units of the following formula:
11. A process for forming a condensation prod
not as de?ned in claim 1 in which equimolar
quantities of an organic monocarboxylic acid and -
2, 4 10,788
16
an alkylol polyamine of the following general
13. A process for forming a condensation prod
uct as de?ned in claim 1 in which equimolar
_ quantities of an organic monocarboxylic acid and
an alkylol polyamine of the following general
in which X represents a simple aikylene group b formula
of from 2 to 3 carbon atoms and in which one
of the hydrogens attached to one of the carbon
atoms is replaced by hydroxyl and in which for
mula the integer e varies from 0 to 4 and m from
2 to 3 are condensed at temperatures between
130-170" C. and thereafter reacted with one-half
mol of urea at 170-200’ C. and thereafter reacted
with an equimolar quantity of polycarboxylic acid
at ISO-200° C. and solubilized by the addition of
one moi of a water soluble acid.
in which X represents a simple alkylene group
of from 2 to 3 carbon atoms and in which one.
of the hydrogens attached to one of the carbon
atoms is replaced by hydroxyl and in which for
mula the integer e varies from 0 to 4 and m from
2 to 3 are condensed at temperatures between
130-170° C. and thereafter reacted with one-half
15 moi of urea at 170-200“ C. and thereafter reacted
12. 'A process for forming a condensation prod
vuct as defined in claim 1 in which equimolar
with an equimolar quantity of polycarboxylic acid
at 150-200" C. and soiubilized by reacting with
‘quantities of an organic monocarboxylic acid and
an alkyklol‘polyamine of the following general
one moi of an aikylating agent as selected from
formula
the group consisting of ethyl chloride, ethylene
20 oxide, benzyl chloride, diethyl sulfate and di
methyl sulfate.-
‘
14. A textile material impregnated with a con
densation product as described in claim 1.
15. A textile material impregnated with an al
.in which X represents a simple aikylene group
of from 2 to 3 carbon atoms and in which one
of the'hydrogens attached to one of the carbon 25 kylated condensation product obtained by a]
atoms is replaced by hydroxyl and in which for
kylating a condensation product as described in
mula the integer e varies from 0 to 4 and m from
2 to 3 are condensed at temperatures between
claim 1 with a compound selected from a group
consisting of ethyl chloride, ethylene oxide, ben
zyl chloride, diethyl sulfate and dimethyl sulfate.
Bil-170° C., said condensate containing free sec
ondary amino groups which is then reacted with
16. A textile material impregnated with the salt
one-halt moi of urea for each secondary amino
which is the addition product of an acid to a
group at temperatures between 170-200" C. and
condensation product as described in claim 1. ,
thereafter further reacted with an equimolar
WILLARD L. MORGAN.
quantity of a polycarboxylic acid at temperatures
. EARLE D. MOLEOD.
between 150-200’ C.
85
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