Note: Descriptions are shown in the official language in which they were submitted.
- 104~407
~his invention relates to a paper sizing agent.
In addition to colophony (rosin), a number of other
compounds have been used in the paper industry as sizing agents,
including by way of example such compounds as fatty acids, fatty
acid anhydrides, fatty amides, diketenes and the like. Compounds
which contain acid groups precipitate as aluminum salts onto the
paper fibers in the sizing procedure, for example, where aluminum
is commonly present in the aqueous siæing solution as when using
aluminum sulfate (alum) as a retention agent in an amount of
about 0.5 to 3.~ and preferably about 1.0 to 2.~/o by weight
based on the paper fibers. The sizing then succeeds only at a
relatively low pH-value, and these sizing agents containing acid
groups therefore have a poor resistance to aging. Also, the
amount of such sizing agents is relatively high, usually about
1.5 to 3% by weight with reference to the fibrous content of the
' paper.
`~` Agents with an acylating or acid-reacting effect, such
as fatty acid anhydrides or alkyl ketene dimers, are also dis- -
advantageous because of their limited stability. They react not
' 20 only with the hydroxyl groups of cellulosic materials but also
'f with all other nucleophilic substances including water. For this
reason, these sizing agents should not be added either at high
pH-values or in the presence of aluminum sulfate at low pH-values.
For a more detailed discus~ion of synthetic sizing
agents, attention is directed to Pulp and Paper Manufacture,
edited by MacDonald and Franklin, Second Edition, Vol. III,
~ McGraw-Hill Book Company, N.Y. (1970), pp. 50-53. This same
-~ reference also discu-~ses surface treatments, including surface
sizing, on pages 71-77, as well a~ internal sizing on pages 35-50
The papermaking proce~s is generally disclosed by this reference
. together with ~itabl~ apparatus, including that which may
be uJed for sizing operations.
"
- 1-
1044407
One object of the present invention is to provide a
synthetic paper size or sizing agent, especially for cellulo~ic
fibers, which overcomes the inadequacies and disadvantages of
the previously used paper sizes. Another object of the invention
is to provide improved paper sizing compositions and procedures
capable of providing better sizing effects and/or more widely
applicable siZing methods. These and other objects and
advantages of the invention will become more apparent upon con-
sideration of the following detailed specification.
It has now been found, in accordance with the present
invention that one can achieve substantially improved results in
the sizing of paper, especially a paper containing cellulosic
; fibers, by an addition to the paper of a synthetic sizing agent
in which the e~sential active component is an N,N'-dialkyl-
~ubstituted aspartimide in which at least one of the alkyl sub-
stituents consists essentially of an alkyl chain of at least 16
carbon atoms and preferably about 18 to 40 carbon atoms.
According to the invention there is provided a stable
~izing agent for paper comprising: a) water; b) an emulsifying
agent; and c) as the active sizing component an N,N'-dialkyl-
substituted aspartimide in which at least one of the alkyl ~ub-
stituents consi~ts essentially of an alkyl chain of at least
16 up to about 40 carbon atom~. -
In another aspect of the invention there is provided
;` a paper product internally or surface sized with a sizing agent
of the invention.
- In yet another aspect of the invention there is
provided a method of sizing paper which comprises applying to
a fibrous paper material a sizing agent of the invention. -~
Other than the ~uccinimido group itself
.'' ~ .
- 2 1
1044407
o
..
-CH - C
H2 C
o
which may be present once or twice, the aspartimide compounds of
the invention may contain a total of about 18 to 104 carbon atoms,
preferably about 40 to 80 carbon atoms, in the alkyl chain or
chains. Although the alkyl chain is preferably a straight chain
of essentially saturated hydrocarbon structure, it may be a
branched chain and it may also be interrupted by one or two
hetero atoms such as nitrogen, oxygen or sulfur. The alkyl
chain may also contain one or two functional groupq, especially
a primary, Qecondary or tertiary amino group. Other functional
groups include hydroxyl, ether, ester, carboxyl or carbonyl
groups. Also included are sulfur-derivatives such as thio-
ether, thioeqter and sulfonic or sulfonyl groups. The presence
-. , ,
of one or two such hetero atoms or functional groups in the
alkyl chain or chains can be tolerated without departing
~ubstantially from the essential hydrocarbon structure of these
chains and without imparing the paper sizing properties of
~ the N,N'-alkyl-subqtituted aspartimide compounds.
,.. ,~ , . . .
,,', , ~.
, ~ .
' :
.~
,~
1~)44407
~ he intentional inclusion of such hetero atoms and
especially the functional groups is of particular advantage
for the purpose of providing especially compatible compo~ition~
for paper treatment where similar lo~g chain alkyl-substituted
compound3 may be used as surface active agents in the sizing
operation or in previous or subsequent treatments of the
paper. Moreover, minor variations in the properties of the
sized paper can be achieved with an otherwise closely related
class of ~izing agents based upon the essential disubstituted
a~partimide structure.
A qingle generic ~tructural formula cannot be given
which will include a number of suitable variations of the .
aspartimide compounds, and in some instanceq it is ea~ier to
provide a mixture of these sizing agents rather than a qingle
. compound.
However, the ~,N'-dialkyl-substituted aspartimideq
of the pre~ent invention, sometimes referred to as
"aqparaginimides" may be generally illustrated by the structural
formula -
i 20 0
'. Il -.
i R -~H-CH-C ~ ::
(I)
CH-C
.~' ~-.
:
' ,,-. .
~ . .
.
~,,
, ~ '
_ 4 _
,
1~)444~7
wherein Rl and R2 each preferably represent a long chain alkyl
group of at least 16 and preferably about 18 to 24 carbon
atoms. It is also feasible, however, to provide somewhat more
complex tertiary amino compounds represented by the formula -
R -~R'-CH- C
1 I N-R2 (II)
2 ~
wherein Rl and R2 have the same meaning given above while R'
is hydrogen, Rl or another radical
O ..
Il
-CH - C ~
CH2- C ~ 2
o
with Rl and R2 again having the same meaning given above.
Two succinimido groups may also be joined by an
alkylene bridge between the imido nitrogen atom as represented
by the formula -
' O
11 11 --
; 1 1 ~ N-(CH2)m-N I 1 (III) ,
.j 2 11 11 2 -,
o . O , . ::
where R" is hydrogen or Rl and m is an integer of 2 up to :
about 8, preferably 3 to 6, and Rl is again a long chain
alkyl group.
.~ .. -,
~ .
:'
,
.. . .
_ 5 _
1044407
Still another representative class of aspartimide
compounds may be illustrated by the formulae
O O
11
/ C-CH-NH-(CH2)m-NH-CH -C \
R2 N \ l l N-R2 (IV)
Il-CH2 CH2--C
O O
wherein R2 i~ the long chain alkyl group and m is an integer
of 2 to 8, preferably 3 to 6.
In all of the noted formulae, it will be understood
that the alkyl chain may contain hetero atoms and/or functional
group~ as described above, i.e. so that Rl and R2 may be
further defined as being long chain radicals of the formulae
( ~2)n R or R4
in which: ~
, n i9 a whole integer of at least 2, ---
R is hydrogen, alkyl, alkoxy, alkoxyalkyl, hydroxy,
~ hydroxyalkyl, hydroxyalkoxyalkyl, thioalkoxy, alkanoyl,
;~ alkoxycarbonyl and alkylcarboxamido or alkylamidocarbonyl; -
and ~
~ n R3 and R4 each represent hydrogen, alkyl, hydroxyalkyl, ~1-
;~ alkoxyalkyl or alkyl ~ub~tituted by a terminal carboxylic
acid or it~ alkyl e~ter, provided however that at lea~t one
~! 20 alkyl radical, and preferably both alkyl radical~, contain~
a total of at lea~t 16 carbon atoms and preferably about 18
up to 40 carbon atoms.
Thus, in addition to the preferred hetero atoms -N-,
-O- and -S- as bridging group~, the~e long chain radical~ may i~
also contain othér functional bridging group~ such as
.
: - - 6 -
,~ . .
1044407 :-
o o o o
-C-O-, -O-C-, -NHC- or -CHN-
or the methylene bridge Y
-CH-
in which Y is hydrogen, alkyl, hydroxy or even other functional
substituents which are essentially inert under a wide range
of sizing conditioniq and up to temperatures of about 200C.
In general, it is preferable to employ those long
chain radicals which are derived from readily available ali-
phatic amineq, especially qaturated fatty amines, but aliqo
diamines and polyalkylpolyamine~.
~he N,N'-dialkyl-subqtituted aspartimides can be -
j easily obtained by melting together at least one amine and
maleic acid anhydride or the lower alkyl esters of maleic
or fumaric acid, followed by heating for a short period of
time, e.g. up to one hour, at a temperature of about 150C. '
` ~ to 200C. In general, the reaction product may be used
directly in its crude form without purification, or it may
7 be recrystallized from a suitable solvent such as acetone.
By way of example, the following types of amines ;~
3 can be identified as being especially suitable for the pre-
`~ 20 paration of the deqired aspartimide compounds. Where the com-
~' pound iq defined by a number, this is its Règistry No. see
Chemical Abstractq Index, 1967-1971, Vols. 66-75.
,,;~
,~ .
,
;i~3
'~!
, ,;
~.i;
,
- 7 -
i
.,
~044407
1. Alkylamines, for example:
HexadecylamQne
Octadecylamine
Eicosylamine
Docosylamine
Tetracosylaminoe
(These amines or their mixtures are commercially
available.)
2. Alkylamines containing an imino (-NH-) bridge in the carbon
chain, for example compounds of the formula
R-NH-(CH2)a-NH2 (V)
wherein a is a ~mall whole integer of about 2 to 6, pre-
: ferably 2 or 3, R preferably being an alkyl chain of
14 29 24 49' :
3. Alkylamines containing a tertiary nitrogen atom in the
~ chain, for exampie compounds of the formula: -
; R
.~ ~ N (CH2)a NH2 (VI) A .,
.~ :
wherein a has the meaning previously given and R is pre-
ferably an alkyl chain of about C6H13 to C24H49. Examples
of ~uch compounds are: .
~ N,N-ditetradecylethylenediamine-1,2 ~ .:
. N,N-dihexadecylpropylenediamine-1,3 ~- -
! N,N-dioctadecylpropylenediamine-1,3
-! N,N-dioctylhexamethylenediamine-1,6 ~ :
~ 4. Amines with an oxygen (-O-) bridge in the carbon chain of ~; -
¦ the formula .
' R-O-(CH2)a-NH2 (VII) .
wherein a has the meaning previously given, especially 2 or
3, and R is an alkyl chain of about C14H29 to C32H65.
Examples of such compounds are:
....
. .
; , . . . . . . . ..
~044407
3-octadecyloxypropylamine (No. 7617-75-6)
3-hexadecyloxypropylamine (~o. 4673-33-0).
: 5. Amines with a sulfur (-S-) bridge in the carbon chain of the
formula
R-S-(CH2)a ~H2 (VIII)
wherein a has the meaning previously given, especially 2 or
3, and R iq again preferably C14H29 to C32H65,*
6. Amine~ containing an ester group in the carbon chain, for
example of the formula
~ 10R-c-o-(cH2)a-NH2 (IX)
wherein a i9 again a ~mall whole integer of about 2 to 6,
preferably 2 or 3, and R is alkyl of about C8H17 to C26H53,
preferably C13H27 to C17H35, Examples of such compounds are
C15H31-c-O~H2)3 ~H2
,'i 0
C17H35-C-O-(cH2)2 ~H2
C17H35-C-0-(CH2)3-NH2 (No. 21632-92-8)
7. Amines with an amide group in the carbon chain, as repre- ~.
sented by the formula
.' ~ .
R-c-NH-(cH2)a-NH2 (X) :
20wherein a has the meaning previously given and R is an alkyl
H17 to C26H53, preferablY C13H27 to C H
Examples of these compoundq are:
* Examples of such compounds are:
Dodecylthiopropylamine (No. 29873-33-4)
Tetradecylthiopropylamine (No. 29873-32-3)
' , ' , ' : ,
1044407
C17H35-C-NH-(CH2)6 NH2 (No. 29474-30_4)
C17H35-C-NH-(cH2)2-NH2 (No. 871-79-4)
8. Amines which carry hydroxy groups on the carbon chain, for
example
9- or 10-hydroxyoctadecylamine (see U.S. 2,712,558)
4-amino-2-methyl-eicosanol (No. 19698-17-0)
10-amino-9-octadecanol (No. 19698-16-9)
l-amino-2,6,10,14-tetramethyl-pentadecanol-2
(No. 2788S-72-9).
9. Amines which carry acid or ester groups on the carbon chain,
for example:
22-amino-docosanoic acid (No, 27306-09-8)
12-amino-stearic acid (No. 30616-18-3)
2-amino-2,6,10,14-tetramethyl-pentadecanoic acid
; (No. 6169-48-8)
9- or 10-amino-stearic acid methyl ester -
(No. 29156-48-7)
6-amino-stearic acid methyl ester (No. 30616-17-2)
All of the above-noted amines represent suitable --
starting materials provided that there is at least one and pre- ~ --
ferably two long chains of at least 16 carbon atoms associated
with one to two of the succinimido rings. However, where one
of the Rl or R2 substituents repre~ents a chain of at least
16 carbon atom~, one may also employ lower alkylamines, alkyl- -
diamines or polyalkylenepolyamines having less than 16 carbon
atoms, e.g. from 2 to 10 and preferably 2 to 6 carbon atoms,
t such as ethylene diamine, hexylamine, hexamethylenediamine,
dipropylenetriamine or the like, The lower alkylene diamines ~ -
are of particular value in forming the bridging group
~(CH2)m~ in formulae III and IV above, Such variations
are possible because the initial acid
~ - 10-
. .
. 104440~
reactant, e.g. maleic acid anhydride, can first be reac-
ted at a relatively low temperaute, e.g. up to 100 C, to
form an amide using one mono- or diamine reactant
H0 - L: - CH
followed by addition of another mono- or diamine reactant
and heating at the higher recommènded temperature of about
150C to 200C to make the addition of the amine group to
the double bond and to close the imide ring.
.`.'
', .
O . .
R - NH - C - CH
+R' -NH2---~ R - NH - C - CH - NH - R'
H0 - ,C, - CH
j O HO - ~ - CH2 .`
~ ' ~
.' 200C
~ O
.~ - ~ C - CH - NH - R'
t R - Nj
Cl - CH~ - -
~:~ O
` i: r; :;
~ ~ '
Z
~, .
,~ ,
~ - lOa -
' 1044407 ~,
Variations in the required temperature depend upon
the initial reactants being used, and it is advisable to employ ;:~
approximately stoichiometric additions at each stage of the reaction
when using di~erent amines.
Surprisingly, even mixed products or products in
relatlvely crude form still possess good paper sizing properties
wlthin the prescribed requirement of at least one long alkyl chain
substituent on the N,N-dialkyl-aspartimide compounds. Preferred ~-
heteroatoms or bridging groups in this alkyl chain are -NH-, -NR-,
, -O- and -CO-, where R is alkyl which may also extend up to 26 carbor
;~ atoms or more, Two or more o~ these bridges may be combined ,
to yield the amide and ester groups -NHCO- or -CO-NH- and -O-CO-
, or -CO-O- as indicated above. Other minor variations such as the
presence of one or two hydroxyl substituents or a number of ~-
lower alkyl substituents are also preferred. ` --
Once the aspartimide compounds have been prepared,
they are preferably made up in the form of aqueous emulsions for ~- -
application as a paper sizing agent. Such emulsions are best ¦ -
produced by thorough mixing with the addition of an emulsifying ¦ --
agent or other components which ensure a uniform stable emulsion ¦ :
II sultable for the treatment of paper. The emulsification of the ¦ ~
¦ aspartimide can thus take place in the presence of one or more of I -
I! the following preferred components;
:
:
., -, .
. ~ '. . '.
',._,. .... . .
~044407
(a) An inorganic or organic acid, e.g. hydrochloric,
ulfuric or phosphoric acids, or acetic, propionic or butanoic
acids or longer chain alkanoic acids:
(b) Cationic or nonionic emulsifiers or surface active
agents of a wide variety known to be useful in paper sizing com-
positions and readily selected from any standard reference, e.g.
quaternary alkyl ammonium chlorides such as hexadecyl- or
octadecyltrimethyl ammonium chloride or the oxyethylated and/or
oxypropylated polyalkylenepolyamines; and
(c) Protective colloids, usually in the form of water-
soluble or water-dispersible polymers, such as gelatin, sodium
alginate, carboxymethyl cellulose (CMC), polyvinyl alcohol (PVA),
or a degraded or cationic starch preparation.
; Other preferred combinations of the paper sizing
aspartimide compounds of the invention are those aqueous com-
positions which may further include one or more of the following
components:
(d) "Alum", the common deqignation for aluminum sulfate, ~;
preferably of a good commercial grade which is low in iron con-
tent this ~ubstance being particularly useful as a complexing
agent in the 3izing liquor;
(e) "Rosin", which consists primarily of abietic acid or
clo~ely related acidq, preferably in smaller amounts as a
"fortified' qizing agent, i.e. a~ compared to where rosin may
be used alone, especially for internal sizing: with the aspart-
imide ~izing agent, rosin can-be added in preferred smaller
'! amounts of 0.01 up to 1%, preferably about 0.1 to 0.5%, based
on the fibrous content of the paper being sized;
(f) Sodium aluminate (~a2A12O4) as an exte d er of
aluminum sulfate;
(g) Wet-end additives such aq polyacrylamides may also be
included in small amounts
- 12 -
.. . .
1044407
(h) Coloring agents, i.e. any compatible dyes or pigment~
useful for imparting color to the paper, and
(i) Fillers and special fibers of all types, especially
cheap materials such as calcium carbonate.
It is of particular value that one can achieve very
good results in paper sizing with relatively small amounts of
the aspartimide sizing agent after it has been emulsified, pre-
ferably with a cationic emulsifier, and then diluted to form a
sizing liquor. In general, it iq sufficient to add less than
1.5% by weight of the aqpartimide sizing agent with reference
` to the fibrous content of the paper and very good results withinternal sizing can be achieved in amounts of about 0.1 to 1% by
weight, and with surface sizing in amounts of about 0.2 to 0.~/0
by weight, again with reference to the dry weight of the fibers -
in the paper. When used in combination with rosin or other
_izing agents, one can uqe even smaller amounts of the aspart- - -
imide while also qubqtantially reducing the required amount of
, the more conventional sizing agent. -
j It i~ eqpecially surprising that the N,N-dialkyl- -
substituted aspartimides of the invention provide good sizing
t properties because other aspar~ic acid derivatives with ~imilar
structures exhibit no qizing activity at all or only an incon-
qequential ~izing effect. Thus, very good ~izing is obtained
with N,N'-dioctadecyl-aspartimide while a similar compound, N-
octadecyl-aspartic acid dioctadecyl ester exhibits no sizing
activity at all. Also, melts of dioctadecylamine and maleic
acid anhydride, which react without formation of the imide ring,
dev-lop only a very incomplete and unsatisfactory sizing effect. :~
:
'
- 13 _
,
, '"t . . , . ~ , . . . . ~ .
0444~7
A special a~vantage Or the invention also resides
in the fact that the aspartimide sizing agents are much more
stable than the acid-forming agents. The sizing compositions
can therefore be prepared as concentrates or a~ diluted liquors
which are very stable in storage and in a wide variety of useful
sizing compositions and under a wide range of sizing conditions.
For example, the new sizing compositions in which the N,Nt-
disubstituted aspartimide is the active sizing component can be
utili~ed in much wider pH ranges.
By comparison to rosin sizlng agents, fatty acids or
thelr anhydrides or fatty amides, the required amounts Or the
N,N'-disubstituted aspartlmide compounds of the present invention
~ are considerably smaller. Thus, as a general rule, it is ~uffi-
i~ cient and especially preferred to use these aspartimides in an ~;
amount of about 0.~ - 0.7% by welght for internal sizing and
about 0.2 to 0.~ by weight for surface sizing, the percentages
being with reference to the fibrous content of the paper.
The fact that these aspartimides can be applied at
hlgher pH-values, for example at a pH of about 4.5 or more,
prererably above 6, for example about 6 to 9, is of particular~
value in producing papers having a ~ery good resistance to aging.
Finally, the new sizing material and the methods of
application permissible therewith offer a coemplo-Jment o~ very
inexpensive fillers such as calcium carbonate or other additives,
` something which cannot ordinarily ~e achieved with ~ r known
natural or synthetic sizing agents.
The use Or specific sizing compositions and the method
of applying them to a cellulosic paper are illustrated in the - ~
following specific examples. The values given for ink resistance - -
: ' "~
., . ~:'
: .: . . ,
10~4407
were determined witht he aid of a "~lercules" sizing tester,explained in Hercules Bulletin PM515, using the ink test
according to German Industrial Standard DIN 53 126. The
time in seconds was measured up to a remission of 80%.
For the Cobb-test, there was used water at 20 C. with
treatment time of one minute. The Cobb value was deter-
mined according to the method described in "TAPPI Mono-
graph", Series No. 33 (1971), pages 108-11~.
The following examples are illustrative only and are
not intended as restrictions on the use of the paper
sizing agent of the invention.
~ ~ .
EXAMPLE 1
580 grams of N,N-dioctadecylpropylenediamine-1,3 and
86 grams of maleic acid diethyl ester were heated for one-
half hour at 200 C., ethanol being distilled off. There
were formed a light colored, pasty substance which con-
sists primarily of N,N'-bis-(N,N-dioctadecylaminopropyl)-
aspartimide as the desired sizing agent. It has the
formula
18H37
CH2CH2CH2-~H
C 1 3H3 7 ~ CH2 CH2 CH2 N--C 1 8H3 7
100 grams of this substance were melted, heated up to
about 100C. And admixed under intensive stirring with
a solution of 20 grams of Arquad 16/50 in 880 grams of
water. (The Arquad 16/50 composition is a trademarked
product obtained from
- 15 -
1044407
Armour & Hes~ Ltd. and is a biodegradable cationic emul~ifier
consisting of a 5~/0 ~olution of hexadecyltrime~hylammonium
chloride in iqopropanol). The resulting emulsion was sent
through a flask homogenizer while hot at about 300 atm. gauge.
From this original emulsion, an aqueous sizing liquor was pro-
duced which contained 4% by weight of degraded starch in addition
to 0.3% by weight of the active sizing agent.
A neutral paper o 70 g/m2 in weight per unit area was
selected for sizing, the paper being produced from 70Y0 coniferous
cellulo~e sulfite pulp and 30Y0 beechwood cellulose sulfite pulp
and 40 SR (the Schopper-Riegler degree of freeneqs of the pulp).
This paper was surface sized on a conventional sizing press
with the sizing liquor with an approximately 10~/o by weight
absorption of the liquor by the paper. Accordingly, the sized
paper contained about 0.3% by weight of the active sizing sub-
stance beside-~ the starch, taken with reference to the cellulosic
fibers. The sized paper, after drying, exhibited an ink re-
sistance of 1.949 sec. and a Cobb value of 21.4.
Example 2
The aspartimide obtained in Example 1 was again made
up into an emuision in the same manner except that the solution
added to make up the original emul~ion contained 20 grams of a -
cationic starch. The surface sizing was carried out exactly
as in Example 1 and resulted in a paper with an ink resistance
of 1.726 sec. and a Cobb value of 19.2.
Examole 3
The aspartimide obtained in Example 1 was again
. .
- emulsified as described therein except that 15 grams of acetic
acid were also present in the aqueous solution used for the s
emulsification besides the cationic emulsifier (arquad 16/50).
The surface sizing wa~ carried out as in Example 1 to yield a
paper with an ink resistance of 1.102 sec. and a Cobb value of
20Ø
- 16 -
10444~7
Example 4
2 mol~ of octadecylamine were melted together with 1
mol of maleic acid anhydride and heated at 180-200C. for one-
half hour. The solidified melt which consisted primarily of
N,N'-dioctadecylaspartimide having the formula
C~8H37 O
; NH-CH- ~ \
I / 18 37
CH2-C
o
was emulsified a~ in Example 1 and then made up into an aqueous
sizing liquor and applied to the paper exactly as described in
Example 1. In this case, a paper was obtained with an ink
resi~tance of 1.048 sec. and a Cobb value of 19.2.
~ Example 5
i The surface sizing described in Example 4 was carried
out with the aspartimide sizing agent as described therein but
using a paper which differed from Example 4 in that it con- ~
tained sufficient aluminum sulfate to yield a pH-value of 4 5. - --
The ~ized paper exhibited an ink resistance of 2.934 sec. and a --
` Cobb value of 16.8. -
Example 6 -
In a paper machine type "Kammerer" used for testing
io purpo~es, there wa~ processed a neutral pulp of 7~YO coniferous -;-
~ cellulose ~ulfite pulp and 30YO beechwood cellulose ~ulfite
;-¦ pulp of 42SR while adding the emulsion according to Example ~ -
4 such that there was incorporated 0.5% by weight of the aspart-
imide ~izing agent as well as 0.3% by weight of Kymene a~ a
retentiorl agent, calculated with reference to the cellulosic -
fiber~, thereby obtaining a sized paper of a weight per unit
,; `
.
- 17 _
.. . , .. , ~ . , : . ;.... . .
10~07
area of 70 g/m . (The Kymene substance is a trademarked product ;
of Hercules Powder, Inc. and is a reaction product of adipic
acid, polyalkylene polyamine and epichlorhydrin.)
The sized paper product in this case had an ink re-
sistance of 766 sec. and a Cobb value of 25.6.
Example ?
3 mols of octadecylamine were melted together with 2
mols of maleic acid anhydride and heated for one-half hour at a
temperature of 180-200C. The elementary analysis of the melt
recrystallized from acetone identified the composition as being
that of N,N-di-(N-octadecylsuccinimido)-octadecylamine having
; the formula
~ . :
O C118H37 0
C-CH - N - CH -C
' H37C18N ` I 18H37 : :.
C~-CH2CH2_CI
. O O
- The crude melt wa~ emulQified a~ in Example 1. It was then
added as a sizing agent to the pulp as in Example 6. The --
re~ulting paper had an ink resi~tance of 2.000 sec. and a
Cobb value of 21Ø -~
Example 8
` 1 mol of N,N-diotadecylpropylenediamine-1,3 was
melted together with 1 mol of maleic acid anhydride at the lowe~t
po~sible temperature. Into this melt, there was introduced 0.5
mol~ of 1.6-diaminohexane, and the mixture was then heated
for one-half hour at 180-200C. The re~ultirg compo~ition was
:`
; - 18 _
. ~, . . .. .
~a(J44~0~
identified by elementary analysis as being that of
N,N' - bis - (dioctadecylaminopropylsuccinimido) - 1,6-
diaminohexane ~f the formula
o
H37C18 C ---CH
- CH2CH2CH2 - ~ CH
O INH
NH
37 18 ~ fH
, N-CH2CH2CH2 - ~ -- CH2
H37C18 1~ :
.' , '
;:
,~ .
~, .' '"' ~
;~
' '
S
:~
,, .
: , . . ..
