USOO53992.

94A
United States Patent (19) 11 Patent Number: 5,399,294
Quednau 45 Date of Patent: Mar. 21, 1995
54) DISPERSINGAGENTS, THEIR USE AND FOREIGN PATENT DOCUMENTS
SOLDS COATED THEREWITH
0154678 1/1984 European Pat. Off. .
75 Inventor: P. H. Quednau, Hillegom, 0270.126 4/1987 European Pat. Off. .
Netherlands 0318999 1/1988 European Pat. Off. .
890691 3/1962 United Kingdom.
73 Assignee: EFKA-Chemicals B.V., Hillegom,
Netherlands OTHER PUBLICATIONS
21 Appl. No.: 634,401 European Search Report, Application No. 9020 3520,
Jun. 6, 1991.
22 Filed: Dec. 27, 1990 Primary Examiner-Robert L. Stoll
30 Foreign Application Priority Data Assistant Examiner-Daniel S. Metzmaier
Attorney, Agent, or Firm-Cooper & Dunham
Dec. 29, 1989 EP European Pat. Off. ........... 89203342 57 ABSTRACT
51) Int. Cl........................ C08G 18/30; C08G 18/72 The present invention relates to dispersing agents or
52 U.S. C. .................................... 252/357; 252/351; their salts, comprising
528/49; 528/83 A the reaction product of one or more polyisocya
58 Field of Search ....................... 252/.351, 356, 357; nates having an average functionality of from 2.0 to
528/28, 49, 69,83; 428/52 5, with
56) References Cited B a mixture from B monohydroxyl compounds and
B2 monohydroxy-, monocarboxylic acid com
U.S. PATENT DOCUMENTS pounds, or monoamino-, monocarboxylic acid
3,684,771 8/1972 Braun .................................... 260/77 compounds and
3,817,944 6/1974 Jones. C a compound containing at least one basic ring nitro
4,032,698 6/1977 Ashe.............................. 526/4 OR gen and an isocyanate-reactive group, in which of
4,070,388 1/1978 ... 560/158 X the isocyanate groups about 30-70% are reacted
4,647,647 3/1987 Haubennestel et al. .............. 528/83 with B and about 30-70% with C,
4,762,752 8/1988 Haubennestel . and the preparation of such dispersing agents.
4,795,796 1/1989 Haubennestel et al. .............. 528/28
4,933,417 6/1990 Yamamoto et al. ........... 528/69 OR
4,942,213 7/1990 Haubennestel et al. .............. 528/28 16 Claims, No Drawings
 5,399,294
1. 2
process stage 3 to the extent of a substantial formation
DISPERSING AGENTS, THEIR USE AND SOLIDS of gel particles and a gelatinization of the entire mass.
COATED THEREWTH The intermediate resulting from reaction stages 1 and
FIELD OF THE INVENTION
2, which is reacted in stage 3 with compounds of for
mula III to obtain a ready-for-delivery product, only
The present invention relates to dispersing agents or has a limited shelf life (about 24 hours) and is therefore
their salts, on the basis of a compound having at least not suitable for supply as a basis for further addition
one ring nitrogen-containing basic group. reactions.
The invention further relates to the use of the dispers 10
The products manufactured by the process described
ing agents and pulverulent or fibrous solids which are show a marked tendency towards gelatinization in the
coated with such dispersing agents and are to be incor third reaction stage so that these reactions can only be
porated in liquid systems. effected in highly diluted solutions, resulting in end
BACKGROUND OF THE INVENTION products which only have a relatively low solid con
15 tent. The increase in solid by subsequent vacuum distill
Powerful mechanical forces are required for intro lation is not possible in view of the marked tendency
ducing solids into liquid media. This depends to a large towards coagulation.
extent on the ease with which the solid can be wetted by The known dispersing agents further have a compati
the surrounding medium and on the affinity to this me bility, a solubility and a dispersing activity which are
dium. To reduce these dispersing forces, it is customary not very good.
to employ dispersing agents which facilitate incorpora 20
It is an object of the present invention to provide
tion. These are in most cases surface-active substances, dispersing agents which, as compared with the known
also known as tensides, which have an anion-active or dispersing agents, have improved properties, in particu
cation-active and nonionic structure. These substances
are added in relatively small quantities, either by direct lar improved compatibility with binding agents, im
application to the solid or by introduction into the dis 25 proved solubility and improved dispersing activity.
persing medium. The effort required for dispersion is It is further an object of the present invention to
substantially reduced by such a tenside. provide dispersing agents which do not have the above
It is also known that these solids tend to reagglomer disadvantages with regard to their preparation or to a
ate after the dispersion process, thus vitiating the effort substantially less extent, and which particularly result in
previously expended for dispersion and leading to seri 30 dispersions of solids which do not tend, or only to a
ous problems. This phenomenon is explained by Lon minor degree, to reagglomerate after the dispersion
don/van der Waal's forces by which the solids attract process.
each other. To overcome these forces of attraction, it is SUMMARY OF THE INVENTION
necessary to apply adsorption layers on the solids. This
is achieved by using such tensides. 35 It has now surprisingly been found that this problem
During and after dispersion, however, an interaction may be solved by means of the dispersing agents defined
between the solid particle and the surrounding medium below.
takes place and desorption of the tenside occurs, accom The invention thus relates to dispersing agents or
panied by its replacement by the surrounding medium, their salts comprising
which is present at a higher concentration. This sur A the reaction product of one or more polyisocya
rounding medium, however, is in most cases not capable nates having an average functionality of 2.0 to 5,
of building up such stable adsorption layers, and the with
whole system breaks down. This manifests itself by a B a mixture from B1 monohydroxyl compounds, and
rise in viscosity in liquid systems, loss of gloss and shift B2 monohydroxy-, monocarboxylic acid com
in colour tone in lacquers and coatings, insufficient 45 pounds, or monoamino-, monocarboxylic acid
development of colour power in pigmented plastics, compounds, and
and decrease of mechanical strength in reinforced plas Ca compound containing at least one basic ring nitro
tics.
European patent application 154,678 discloses a dis gen and an isocyanate-reactive group, wherein of
persing agent comprising the reaction product of a 50 the isocyanate groups about 30-70% are reacted
polyisocyanate having a valence of from 2.5 to 6 with a with B and about 30-70% with C.
monohydroxyl compound, a difunctional component It has now surprisingly been found that the dispersing
and a compound containing a basic ring nitrogen. agents according to the invention show a better com
Due to the nature of the compounds and the reactions patibility with, e.g., alkyd resins and oil-free polyester
connected therewith, it is essential for the product to be 55 resins, a better solubility and a better dispersing activity
manufactured by a multistage method. With regard to of different pigments that are hard to stabilize.
the production efficiency this is not desirable. More The above advantages are very important in using
over, the problem occurs that both the intermediate and these dispersing agents. In consequence thereof, the
the end product are not very stable and tend to gelatini binding agents can be better used for the dispersion of
zation. pigments in binding agents. More in particular, the bet
More in particular, it may be noted that it is necessary ter solubility offers the possibility of using the dispers
according to the known method to use a multistage ing agents in high-solids lacquers because it is advanta
process wherein after stage 1, in which the polyisocya geous in such systems to use fewer solvents.
nate must first be reacted with the monomer com When monohydroxycarboxylic acids or monoamino
pounds, a difunctional compound cannot be used until 65 carboxylic acids are used instead of the known di- and
in stage 2. If this uneconomical process is not used and trimeric compounds described, the following advan
the components from stages 1 and 2 are therefore re tages can be obtained in the preparation of the dispers
acted from the beginning, complications will occur in ing agents:
 5,399,294
3 4
The laborious and uneconomical 2-stage process for or which may be obtained by the biuret reaction,
preparing the intermediate described in European pa- trade product: DESMODURN (TM), having the for
tent application 154,678 can be carried out in one stage mula
when using monohydroxycarboxylic acids without the
occurrence of gelatinization with the reaction in the 5 O
third stage. I
The initial products manufactured with monohydrox- C-NH-(CH2)6-NCO
ycarboxylic acids or monoaminocarboxylic acids have a OCN-(CH2)5-N
substantially improved shelf life (several weeks) so that
the most different end products can be manufactured 10
from an intermediate, also after a prolonged intermedi- O
ate Storage.
or the polyisocyanates obtainable by the cyclization
DETAILED DESCRIPTION OF THE of diisocyanates and having an isocyanurate basic struc
PREFERRED EMBODIMENTS 15 ture, trade product: DESMODURHL (registered trade
In view of the low tendency towards gelatinization in mark), having the formula
the third reaction stage, it is possible to manufacture end
products having an increased solid content, which is
advantageous in the manufacture of lacquers having a H3C
high solid content. 20 -CN -CS
According to the invention a polyisocyanate having a OCN techn eCH3NCO,
functionality of from 2,0 to 5, preferably about 4, is used --...-a, -Si-CN
in the dispersing agents. Suitable polyisocyanates are O N OO N O
those which may be obtained, e.g., by the addition of
diisocyanates to polyols, trade product: DESMODUR 25
L (TM), having the formula NCO NCO
NCO CH3 CH3

CH2OCONH CH3 30 trade product:: DE

DESMODUR IL (registered trade
mark), having the formula
NCO H3C CH, CH3
CH3-CH2-C-CH2OCONH CH3 OCN
C C C C
o1N1 No o1 NN1 No
NCO
40
NCO NCO
CH2OCONH CH3 CH3 CH3

trade product: POLURENE KC (registered trade

45 mark), having the formula

OCN O O O NCO

c-)--C-ai-O-Si-C-al-O---a
OC
C

CO OC
C

CO OC
C

CO

NCO NCO NCO

CH3 CH3 CH3

65

trade product: POLURENE HR (registered trade

mark), having the formula
 5,399,294
5
OCN O H3C

re--R
NN
as OC
R O H3C
C

CO 1N
C

C
NCO
oc-CO N1 na N O NCO
o na N1
bo N1 NN
C CH3;
CH3 NCO
OC CO
CH3 NCO NN1
CH3 NCO

CH3
toluylene diisocyanate-isophorone diisocyanate cyan
urate, having the formula
20
O Substituents reactive with isocyanates under the condi
tions of preparation of the dispersing agent according to
f C (
OC CO OC
Cy cCO
25
the invention.
The monohydroxyl compounds used may be ali
phatic, cycloaliphatic and/or araliphatic compounds.
CH3 N
Mixtures of such compounds may also be used. Straight
"sal
H3C CH2NCO
CH3
NCO
chained and branched aliphatic or araliphatic com
pounds may be used. They may be saturated or unsatu
rated. Saturated compounds are preferred. The hydro
gen atoms may be partly replaced by halogens, prefera
or trimeric isophorone diisocyanate (isocyanurate bly by fluorine and/or chlorine. When such substituted
T1890 of Chemische Werke Hils). having the formula compounds are used, they are preferably aliphatic mo
noalcohols. Such products are commercially available
and the carbon atoms close to the hydroxyl group, as is
35 well known to those skilled in the art, generally have no
halogen atoms. Examples of specially fluorinated alco
hols include heptadecafluorodecanol O
C6F13CH2CH2OH. The commercially available corre
sponding products are frequently not uniform but mix
tures of different fluorinated compounds as obtained
from technical synthesis.
OCN NCEO The monohydroxyl compounds may also contain at
least one -O- and/or COO- group, which means
they are polyethers, polyesters or mixed polyether
45 polyesters. Examples of polyesters include those which
may be obtained by the polymerization of a lactone
such as propiolactone, valerolactone, caprolactone or
As already mentioned above, the relevant com substituted derivatives thereof, using a monohydroxyl
pounds are trade products which frequently do not starting component. The starting components used are
have the above chemical formulae in their pure form 50 monoalcohols, suitably with 4 to 30, preferably 4 to 14
but are mixtures of certain compounds of a similar struc carbon atoms, such as n-butanol, relatively long
ture. By average functionality is meant that with regard chained, saturated and unsaturated alcohols such as
to the isocyanate groups, the trade products have the propargyl alcohol, oley alcohol, linoloy alcohol, oxo
given functionality of from 2.0 to 5, preferably about 4. alcohols, cyclohexanol, phenyl ethanol, neopentyl alco
The mixture of hydroxyl compounds anyhow con 55 hol, but also fluorinated alcohols of the kind mentioned
tains at least one monohydroxyl compound with an above. Alcohols of the type described above and substi
aliphatic and/or cycloaliphatic hydrocarbon which tuted and unsubstituted alcohols may also be converted
may or may not be substituted with aryland/or halogen into polyoxyalkylene monoalkyl-, aryl-, aralkyl- and
groups, or may contain one or more ether and/or ester cycloalkyl ethers by known methods of alkoxylation
groups. Preferably, the monohydroxyl compound has a with ethylene oxide and/or propylene oxide, and these
molecular weight of at least 500 and more in particular monohydroxypolyethers may be used in the manner
of from 750 to 3500. An optimum dispersing activity is prescribed as starting components for lactone polymeri
obtained with these molecular weights. It is also possi sation. Mixtures of the above-mentioned compounds
ble to incorporate one or more substituents in the may be used in all cases. These polyesters suitably have
monohydroxyl compound which increases the compati 65 a molecular weight within the range of from about 300
bility with alkyd resins. to 8000, preferably 500 to 5000.
It may be important that in addition to the hydroxyl There may also be used monohydroxypolyethers
group the relevant monohydroxyl compound has no obtained by the alkoxylation of alkanols, cycloalkanols
 5,399,294
7 8
and phenols. These polyethers suitably have a molecu atom, which preferably reacts with the isocyanate
lar weight within the range of from about 350 to 1500. groups, and that they in addition contain a basic group
The mixture of hydroxyl compounds also contains at which contains nitrogen and which is not capable of
least one monohydroxy-monocarboxylic acid com reacting with isocyanate groups to form urea. These
pound. Preferably, a hydrocarbon compound is suitably basic groups are also characterised according to the
used with at least 8 carbon atoms contained between the state of the art by their pKa-value (compare U.S. Pat.
hydroxyl group and the carboxylic acid group. If de Nos. 3,817,944; 4,032,698 and 4,070,388). Compounds
sired, this carbon chain may be interrupted by amide, with basic groups having a pKa-value of from 2 to 14
ether, ester, S, SO2 and/or urethane groups. To im are preferred, especially those with pKa-values of from
prove the compatibility of the dispersing agent with O 5 to 14 and most especially those with pKa-values of
different materials, it is generally preferred that the
molecular weight of the monohydroxy-monocarboxylic from 5 to 12. The pKa-value can be obtained from ta
acid compound is at least 500, more in particular of bles. The limiting values given above refer to the mea
from 750 to 4000. surement of the pKa-value at 25 C. at an 0.01 molar
Suitable monohydroxy-monocarboxylic acid com 15 concentration in water. These basic groups also impart
pounds may be obtained by the esterification of hydrox a basicity to the addition compounds according to the
ycarboxylic acids, by the reaction of a diol with a dicar invention, as is also known in this field of the art (com
boxylic acid or an anhydride. It is possible to start from pare the above-mentioned U.S. patent specifications).
a diol of higher molecular weight such as a polyethyl Due to these basic groups, the addition compounds are
ene glycol and to react it with a single dicarboxylic acid 20capable of salt formation. According to the invention,
or a dicarboxylic anhydride. It is also possible to react a they may also be used in the form of such salts as dis
dicarboxylic acid of high molecular weight with a diol persing agents.
of low molecular weight. Finally, it is also possible to These salts are obtained from the resulting reaction
react almost stoichiometric quantities of diol of low product by neutralisation with organic or inorganic
molecular weight and dicarboxylic acid of low molecu 25 acids or by quaternisation. Salts with organic monocar
lar weight with each other under such conditions as to boxylic acids are preferred.
form as much monohydroxy-monocarboxylic acid as It is to be noted that it may also be possible to incor
possible and anyhow no or substantially no dihydroxyl porate a minor quantity of a dihydroxyl compound in
compound. Preferred is the use of the reaction product the dispersing agent according to the invention. The
of dicarboxylic acid of low molecular weight with a 30 quantity thereof is, however, always such that only a
diol of higher molecular weight such as polyethylene
glycol. fraction, i.e. less than 5%, preferably less than 2.5% of
The monohydroxy-monocarboxylic acids may be the isocyanates groups is reacted therewith. Preferably,
replaced in whole or in part by monoamino-monocar however, no dihydroxyl compound is present.
boxylic acids. Analogous remarks apply to the 35 The reaction of isocyanate groups takes place by
monoamino-monocarboxylic acid as to the monohy applying known methods. In general, it is preferred to
droxycarboxylic acid. carry out the reaction in such a manner that in a first
The ratio of the quantities of hydroxyl groups con stage the polyisocyanate is reacted with a mixture of a
tained in, on the one hand, the monohydroxyl com monohydroxyl compound and a monohydroxy
pound and, on the other hand, the monohydroxy monocarboxylic compound. This reaction generally
monocarboxylic acid compound may vary within rela occurs in a suitable solvent (e.g. hydrocarbons such as
tively broad limits, depending on their use. Preferably, xylenes, ethers such as dioxane, esters such as butyl
the monohydroxy-monocarboxylic acid compound is acetate, and dimethylformamide), optionally in the
present in a deficiency with respect to the monohy presence of a catalyst such as dibutyltin dilaurate, iron
droxyl compound. The ratio of the number of hydroxyl 45 acetyl acetonate or triethylenediamine. It is also possi
groups originating from both types of compounds var ble, but not preferred, to first react the polyisocyanate
ies from 1:1 to 10:1. Preferably, this ratio ranges from with the monohydroxyl compound and to further react
2:1 to 5:1. When using a monoamino-monocarboxylic the resulting reaction product with the carboxylic acid
acid compound, the ratio of the number of hydroxyl compound.
groups from the monohydroxyl compounds and the 50 After this reaction, in which in general about 40-80%
number of amino groups is from 1:1 to 10:1. Preferably, of the isocyanate groups will be reacted, the reaction is
this ratio is from 2:1 to 5:1.
An important component in the dispersing agent carried out with a compound containing a basic ring
according to the invention is a compound containing a nitrogen. This will lead to a reaction of about 20-60%
basic ring nitrogen. Suitable compounds are: N,N-dieth 55 of the isocyanate groups. Isocyanate groups that may
yl-1,4-butanediamine, 1-(2-aminoethyl)-piperazine, 2-(1- not have reacted are finally deactivated by the reaction
pyrrolidyl)ethylamine, 4-amino-2-methoxy-pyrimidine, with a lower alcohol or a comparable compound. Par
2-dimethylaminoethanol, 1-(2-hydroxyethyl)-pipera ticularly butanol is suitably used.
zine, 4-(2-hydroxyethyl)-morpholine, 2-mercap The invention will now be illustrated by some exam
topyrimidine, 2-mercaptobenzimidazole. Particularly ples but is not limited to them.
preferred are N,N-dimethyl-1,3-propanediamine, 4-(2- Example of preparation A
aminoethyl)-pyridine, 2-amino-6-methoxybenzo
thiazole, 4-(aminoethyl)-pyridine, N,N-diallyl-mela 31.92 g caprolactone, 10.40 g HD-Ocenol 45/50
mine, 3-amino-1,2,4-triazole, 1-(3-aminopropyl)- (Henkel & Cie., Disseldorf) are dispersed under an inert
imidazole, 4-(2-hydroxyethyl)-pyridine, 1-(2-hydroxye 65 gas. 0.0012g dibutyltin dilaurate are added and heated
thyl)-imidazole, 3-mercapto-1,2,4-triazole. to 170° C. with stirring until a solid of 99% is obtained
Characteristic of these compounds is that per mole (about 8 hours). The product is solid at room tempera
cule they contain at least one Zerewitinoff hydrogen ture and slightly yellowish in colour.
 5,399,294
9 10
Example of preparation B Example 3
60.0g polyethylene glycol having the average molec 4.42 g of a caprolactone polyester (Example A) and
ular mass of 1000 are molten under an inert gas. 17.10 g 8.40 g Desmodur IL (51% in butyl acetate) are dis
tetrachlorophthalic anhydride are added with stirring solved in 6.12 g butyl acetate and 7.20 g methoxypropyl
and heated to 150° C. The reaction is completely termi acetate with introduction of nitrogen and stirring. Then
nated as soon as an acid number of 43.6 is obtained; 1.71 g monohydroxycarboxylic acid (Example B) are
duration about 4 hours. The product is waxy at room added and the formulation is heated to 70° C. After a
temperature and is whitish-yellowish in colour. reaction time of 2 hours the addition has occurred,
O
Example of preparation C which is recognisable at the NCO content. A mixture of
75.00 g polyethylene glycol having the average mo 0.75 g 1-(3-aminopropyl)-imidazole dissolved in 2.95 g
lecular mass of 1000 are molten with introduction of
of N-methylpyrrollidone is added and further stirring
nitrogen. When the diol becomes liquid, 11.10 g takes place for one hour. At the end, an excess of n
phthalic anhydride are added and heated to 150 C. 15 butanol is added to react NCO groups that are not re
with stirring. The reaction is completely terminated acted. The product is light yellow in colour and vis
COS
when an acid number of 48.87 is obtained. The product In a parallel formulation 1.40 g of polyethylene gly
is waxy at room temperature. col 1000 were added instead of the 1.71 g of monohy
Example of preparation D 20 droxycarboxylic acid. In this formulation, addition of
394 g pentahydro-perfluorononanediol are molten. the 1-(3-aminopropyl)-imidazole NMP solution led to
266.30 g dodecenyl succinic anhydride are added under gelatinization, so that the product was unsuitable for
S.
an inert gas and with stirring and heated to 150 C. The
reaction is completely terminated as soon as an acid Example 4
number of 96 mg KOH/g is obtained. The resinous 25 In a synthesis apparatus 25.39 g caprolactone polyes
product is yellow in colour; it is used in 70% form as a
solution in methoxypropyl acetate. ter (Example A) and 42.00 g Desmodur IL (51% in
butyl acetate) are dissolved in 38.31 g butyl acetate and
Example 1 33.32 g methoxypropyl acetate with introduction of
41.06 g of a caprolactone polyester (Example A) and 30 nitrogen and stirring. Then 6.58 g monohydroxycar
63.00 g Desmodur IL (51% in butyl acetate) are dis boxylic acid (Example B) and 1.89 g monohydroxycar
solved in 42.48g butyl acetate and 40.99g methoxypro boxylic acid solution (Example D) are added and the
pyl acetate with introduction of an inert gas and stir formulation is heated to 70° C. After a reaction time of
ring. Then 1205 g monohydroxycarboxylic acid (Exam 2 hours the addition has occurred, which is recognisable
ple of preparation C) are added and the formulation is 35 at the NCO content. 14.10 g butyl acetate and 14.10 g
heated to 70° C. After a reaction time of 2 hours the methoxypropyl acetate are added, to which 21.94 g of a
addition has occurred, which is recognisable at the 22.79% solution of 1-(3-aminopropyl)-imidazole in
NCO content. 32.44 g of a 20% solution of 2-amino-4- NMP are added, and further stirring takes place for one
methylpyridine in MNP are added and further stirring hour. At the end, an excess of n-butanol is added to
takes place for 1 hour. At the end, an excess of n react NCO groups that are not reacted. The viscous end
butanol is added to react NCO groups that are not re product is straw yellow in colour.
acted. The viscous end product is yellowish in colour We claim:
and has a solid content of 39.54%. 1. Dispersing agents or salts, thereof, comprising:
In a parallel mode of experimental procedure the the reaction product of
equivalent proportion of polyethylene glycol 1000 ( 45 A. one or more polyisocyanates having an average
10.50 g) was used instead of the monohydroxycarboxy functionality of from 2.0 to 5, with
lic acid. Here addition of the 2-amino-4-methylpyridine B a mixture of
solution already led to gelatinization after only 50% of B1 at least one monohydroxyl compounds selected
the solution had been added from the group consisting of monohydroxyl com
50
Example 2 pounds with an aliphatic hydrocarbon, monohy
23.27g of a caprolactone polyester (Example of prep droxyl compounds with an aliphatic hydrocarbon
aration A) and 42.00 g Desmodur IL (51% in butyl substituted with aryl groups, monohydroxyl com
acetate) are dissolved in 30.62 g butyl acetate and 36.02 pounds with an aliphatic hydrocarbon substituted
g methoxypropyl acetate with introduction of nitrogen 55 with halogen groups, monohydroxyl compounds
and stirring. Then 7.68 g monohydroxycarboxylic acid with a cycloaliphatic hydrocarbon, monohydroxyl
(Example B) are added and the formulation is heated to compounds with a cycloaliphatic hydrocarbon
70° C. After the addition (about 2 hrs) has ocurred, substituted with aryl groups, and monohydroxyl
15.11 g of a 16.67% NMP solution of 3-amino-1,2,4- compounds with a cycloaliphatic hydrocarbon
triazole are added and further stirring takes place for 60 substituted with halogen groups, and
one hour. At the end, an excess of n-butanol is added to B2 at least one monohydroxy-monocarboxylic acid
react NCO groups that are not reacted. The product has compound, the monohydroxy-monocarboxylic
medium viscosity and is light yellow in colour. acid compound obtained by esterification of hy
In a parallel formulation 7.00 g polyethylene glycol drocarboxylic acids or by reaction of a diol with at
1000 were used instead of the 7.68 g monohydroxycar 65 least one dicarboxylic acid or anhydride com
boxylic acid. Here addition of the 3-amino-1,2,4,- pound,
triazole solution led to complete gelatinization of the to form an intermediate, followed by reacting the inter
mass, so that it was unsuitable for use. mediate with
 5,399,294
11 12
C. a compound containing at least one basic ring compound is less than the amount of monohydroxyl
nitrogen and a group which is capable of reacting compound.
with an isocyanate group, 12. Dispersing agents according to claim 11, wherein
wherein about 30–70% of the isocyanate groups of the the ratio of the number of hydroxyl groups of monohy
polyisocyanates are reacted with B1 and B2 and about 5 droxyl compound to the number of hydroxyl groups of
30-70% with C. monohydroxymonocarboxylic acid compound varies
2. Dispersing agents according to claim 1, wherein from 2:1 to 5:1.
the at least one monohydroxyl compound contains 13. Dispersing agents according to claim 11 wherein
ether groups. the compound containing at least one basic ring nitro
3. Dispersing agents according to claim 1, wherein O gen and group capable of reacting with an isocyanate
the monohydroxyl compound contains ester groups. group is 1-(2-aminoethyl)-piperazine, 2-(1-pyrrolidyl)-
4. Dispersing agents according to claim 1, wherein ethylamine, 4-amino-2-methoxy-pyrimidine, 2-dime
the monohydroxyl compound has a molecular weight thylaminoethanol, 1-(2-hydroxyethyl)-piperazine, 4-(2-
of at least 500. hydroxyethyl)-morpholine, 2-mercaptopyrimidine, or
5. Dispersing agents according to claim 4, wherein 5 2-mercaptobenzinidazole.
the at least one monohydroxyl compound has a molecu 14. Dispersing agents according to claim 1, wherein
lar weight ranging from 750 to 3500. the ratio of the number of hydroxyl groups of the at
6. Dispersing agents according to claim 5, wherein least one monohydroxyl compound to the number of
hydroxyl groups of monohydroxy-monocarboxylic acid
the carbon chain includes amide, ether, ester, S, SO2 or compound ranges from 1:1 to 10:1.
urethane groups. 15. Dispersing agents according to claim 1, wherein
7. Dispersing agents according to claim 1, wherein per molecule of the compound containing said at least
the at least one monohydroxy-monocarboxylic acid one basic ring nitrogen contains at least one Zerewitin
compound having at least eight carbon atoms contained off hydrogen atom reactive with the isocyanate groups,
between the hydroxyl group and the carboxylic acid 25 and wherein the nitrogen-containing basic group is not
group. capable of reacting with isocyanate groups to form
8. Dispersing agents according to claim 1, wherein ca
the molecular weight of the monohydroxy-monocar 16. Dispersing agents according to claim 1, wherein
boxylic acid compound is at least 500. the compound containing at least one basic ring nitro
9. Dispersing agents according to claim 8, wherein 30 gen and group capable of reacting with an isocyanate
the monohydroxyl compound has a molecular weight group is 4-(2-aminoethyl)-pyridine, 2-amino-6-4-(2-
of from 750 to 3500. aminoethyl)-pyridine, 2-amino-6-methoxybenzo
10. Dispersing agents according to claim 8, wherein thiazole, 4-(aminoethyl)-pyridine, N,N-diallylmela
the molecular weight of the monohydroxy-monocar mine, 3-amino-1,2,4-triazole, 1-(3-aminopropyl)-
boxylic acid compound is from 750 to 4000. 35 imidazole, 4-(2-hydroxyethyl)-pyridine, 1-(2-hydroxye
11. Dispersing agents according to claim 1, wherein thyl)-imidazole, or 3-mercapto-1,2,4-triazole.
the amount of monohydroxy-monocarboxylic acid k ck k sc

45

50

55

60

65