Process for the preparation of high molecular thermoplastic epoxide-amine-polyadducts

High molecular linear, thermoplastic, epoxide-amine-adducts containing the structural segment ##STR1## are prepared by a solvent-free reaction of equivalent amounts at 20 to 200.degree. C. of N,N'-bis(aralkyl) diamines (for example, N,N'-dibenzyl-ethylenediamine, N,N'-dibenzyl-p-xylylenediamine, N,N'-dibenzyl-4,4'-diamino-diphenylmethane, N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8) with diepoxides (for example, 2,2-bis(4-glycidyloxyphenyl)propane). The polyadducts are soluble and may be processed by thermoplastic methods. The polyaddition process may be conducted for the forming of shaped objects in a form-shaping vessel, for the production of coatings directly upon the surface to be coated and also in the presence of inserted materials and has, due to these characteristics, the nature of a casting system.

FIELD OF USE OF THE INVENTION 
The invention relates to a method of preparing high molecular thermoplastic 
epoxide-amine-polyadducts containing as polyhydroxylpolyamine-compounds 
the following characteristic structural segment: 
##STR2## 
High molecular polymers of this kind, possess as do 
three-dimensionally-crosslinked epoxide-amine-polyadducts, high mechanical 
stability, good electrical properties and good adhesion, all properties 
which allow manifold uses for molded goods, adhesives, lacquers, coatings, 
films, for embedding and insulating electronic components, as a laminating 
agent or a casting resin and many other purposes. 
Due to their thermoplasticity and solubility, the epoxide-amine-polyadducts 
according to the invention are even more all-encompassing and more 
advantageous in their technological uses than the 
three-dimensionally-crosslinked epoxide-amine-polyadducts and are 
particularly useful for the production of films and fibers from melts or 
solutions and also for casting, extrusion, pressing and drawing. 
CHARACTERISTICS OF KNOWN PRIOR ART 
While polymeric lattices consisting of epoxide resins and polyamines are 
well researched and are being used in many technical applications, the 
polyaddition of diepoxides to disecondary diamines yielding unbranched and 
uncrosslinked polyadducts of the aforegiven structure was obtained up to 
now in exceptional cases only (related to R, R' and R") and under specific 
processing conditions, usually by reacting in appropriate solvents. 
Hereinbelow, "DRP" means Federal Republic of Germany Pat. no., "USP" means 
U.S. Pat. No., "DDR" means German Democratic Republic and preceded by "WP" 
means application. 
DRP Pat. No. 676,117 already teaches how to prepare addition products of 
impure diepoxides and various disecondary diamines in solvents containing 
hydroxyl groups. According to the disclosure, these are resinous products, 
which are neither high molecular products nor can they be called 
thermoplastic according to the specific terminology of high molecular 
materials. Furthermore, it is obvious that the respective addition 
products may be produced only by reaction in a solvent and that such a 
method makes the preparation of castable products impossible. 
Later appearing literature concurs that the synthesis of non-crosslinked 
polyadducts in the absence of solvents is a subject presenting large 
difficulties (Methoden der Organischen Chemie (Houben-Weyl), vol. XIV/2, 
page 499, Georg Thieme Publishers, Stuttgart 1971; K. Jellinek, II. 
Internat. Tagung ueber glasfaserverstaerkte Kunststoffe und Giessharze, 
Berlin, Mar. 13 to 18, 1967). That seems to be caused by the catalytic 
action of the tertiary amine groupings upon the ring opening 
polymerization of the epoxide groups which should be excluded here or 
because the hydroxyl groups arising here interfere with the reaction. 
Particularly the partial polymerization of the epoxide, which is so 
undesirable, would cause a disturbance of the molar equivalency of the 
components of the polyaddition system and would also cause crosslinking. 
Therefore, it was up to now not possible, particularly due to the high 
tendency of the epoxide groups to homopolymerization, to create high 
molecular non-crosslinked casting resins similar to the systems leading to 
polyurethane thermoplastics. That forced the experts to find other methods 
for the solution of the technical demands, for instance in order to obtain 
flexibilization and toughening. On the other hand, in cases where 
solubility, thermoplasticity or meltability are demanded, oligomers had to 
be used, where the known disadvantages, due to the low molecular weight 
(brittleness, structural weakness) had to be taken in the bargain or had 
to be cured by additional reactions. 
Experiments to prepare high molecular, thermoplastic and non-crosslinked 
epoxide-amine-adducts were frequently undertaken. Makromolekulare Chemie 
116, 158-172 (1968) describes the polyaddition of 
N,N'-bis(2,3-epoxy-propyl)piperazine (analogous to DRP Pat. No. 676,117 
(example 2)) with primary aliphatic and aromatic amines and with 
aliphatic, aromatic and cycloaliphatic, heterocyclical disecondary 
diamines. The polyreaction is again executed in solvents and leads to low 
molecular products, having relative molecular weights of 2000 to 6900. 
Piperazine and N,N'-dialkylsubstituted aliphatic diamines react with 
2,2'bis(4-glycidyloxyphenyl)propane in dilute solutions yielding 
oligocycles and not high molecular polymers (S. Ore, O. G. Tjugum, Acta 
chim. Scand. 24, 2397 (1970)). It is within the state of the art (U.S. 
Pat. No. 3,554,956) to prepare thermoplastic 
polyhydroxyl-polyamine-compounds by mixing an epoxide compound with 
terminal 1,2 epoxide groups and a disecondary diamine at a molecular ratio 
0.9-1.1:1, said mixture containing an inert dilution agent as an essential 
component. It is exceedingly disadvantageous and severely restricting that 
this synthesis can only be performed in the presence of the aforementioned 
dilution agent. As shown in example 1 of the patent, the absence of a 
dilution agent causes the appearance of nonmelting products, useless as 
thermoplastics. High molecular thermoplastic casting systems or similar 
compounds cannot be prepared by this method and the present state of the 
art does not generally allow the preparation of high molecular 
thermoplastic polyadducts by using disecondary amines. 
Furthermore, it is known that the special case of the reaction of 
N,N'-dimethylethylenediamine with resorcinol-diglycidylether leads to a 
soluble polyadducts (U.S. Pat. No. 3,592,946). The disadvantages of this 
method are that it applies to one special case only, that many 
elastomeric, non-thermoplastic by-products occur and that the reaction of 
the aforementioned disecondary diamine with the resorcinol-diglycidylether 
occurs very rapidly so that the control of the reaction becomes very 
complicated. Furthermore, the high volatility and the CO.sub.2 
-sensitivity of the amine cause considerable technical difficulties in the 
preservation of the stoichiometry of the reaction partners. 
It was furthermore proposed to prepare optical adhesives for the low-strain 
glueing of optical parts, hardening at room temperature and separable in 
the temperature range of 120.degree. to 200.degree. C., based upon 
unmodified, low molecular epoxide resins, containing at least two epoxide 
groups per molecule and N,N'-dibenzyl-ethylenediamine (DDR Patent 
Application No. CO9J/202908) and also other disecondary diamines (WP-DDR 
Pat. No. 122,258, WP-DDR Pat. No. 130,580). Here, though, it was not the 
aim to prepare high molecular thermoplastic epoxide-polyadducts, so that 
these methods were not even aimed at solving the task of the present 
invention. The relative molecular weights of the polyadducts useful as 
optical adhesives lie generally below 6000, so that even hardened optical 
adhesives according to these patents will not have the properties which 
are so typical for the high molecular thermoplastic epoxide-amine-adducts 
and which make these polymers so valuable as raw materials. Some 
mechanical properties like impact resistance, resistance to tear, 
toughness are functions of the molecular weight; the desired properties of 
interest to industry are obtained in this special case only at M.sub.n 
&gt;8000 values. 
Several other epoxide-amine-hardening systems were proposed, using also 
secondary diamines but not leading to thermoplastic high molecular 
epoxide-amine-polyadducts and are thus not conducive to a solution of the 
present problem. They have generally the disadvantage that their hardening 
leads to insoluble, unmeltable crosslinked products (German Pat. No. 
1019481, German Pat. No. 1038278, German Off. No. 2164099. Brit. Pat. No. 
868,733). 
OBJECT OF THE INVENTION 
The object of the invention is to find a generally usable method for the 
preparation of high molecular (M.sub.n &gt;8000) thermoplastic 
epoxide-amine-polyadducts without the use of diluents and where variation 
of the addition components leads to a broad gamut of polyadducts having 
various physical properties, where particularly thermoplastic materials 
with glass transition temperatures T.sub.g of 0.degree. to 150.degree. C. 
result. 
DESCRIPTION OF THE INVENTION 
It was surprising and not possible to foresee that high molecular 
thermoplastic epoxide-amine-polyadducts may be synthesized according to 
the invention as follows: a diepoxide, preferably a diglycidylether, e.g., 
2,2'bis(4-glycidyloxyphenyl) propane, is reacted without solvent or 
diluent with a diamine of the structure DA 
##STR3## 
at a molar ratio 1.0:1.0 where R is an aralkyl, preferably a benzyl, and 
R' radical is a difunctional branched or unbranched hydrocarbon, either an 
alkylene, a cycloalkylene, an arylene or a difunctional heterocyclic 
compound, and where R' may be a mixed radical of these classes or also 
hetero-atoms (for instance O, S, N) or other respective radicals 
containing multiple bonds. 
According to the invention, high molecular polyaddition-products are 
obtained when the molar ratio of the polyaddition-components lies between 
0.95:1.0 and 1.0:1.05 (diepoxide:diamine) even when mixtures of diamines 
of the invention or mixtures of diepoxides of the invention are used. 
The method may also be used in such a manner that the poly-addition process 
leads to the forming of shaped products directly in a form-shaping mold or 
to the development of coatings directly upon a surface to be coated. One 
can also produce adhesive bonds and gaskets directly between the parts to 
be bonded or gasketed, and it is possible to reinforce fibers, to produce 
combined materials or laminations by a direct poly-addition process. 
Very well suited diepoxides for use in this invention are 
2,2'-bis(4-glycidyloxy-phenyl)propane, bis(glycidyl)-alkyl-ether or 
-arylether, bis(glycidyl)amine and similar compounds. 
The process of the invention may, of course, be extended also for use with 
diepoxide-resins which contain a mixture of several diepoxides. Here a 
difficulty arises because admixtures containing one epoxide group only or 
more than two epoxide groups per molecule have to be excluded and also in 
the preservation of the equivalency of the partners of reaction. The 
optimal amount of diamine is here determined by the determination of the 
equivalent weight or by experimental trials. 
The polyaddition according to the invention is realized in a simple manner 
by mixing well the equivalent amounts of diepoxide and disecondary amine 
and keeping them reacting, if needs be by heating, until the desired 
molecular weight (above 8000) is obtained. Depending on the radicals R and 
R', it is advantageous to keep the temperature of reaction between 
20.degree. and 200.degree. C. It is practical to increase the temperature 
of reaction slowly to the glass transition temperature of the 
polyproducts, to keep it there for a prolonged time and finally to 
increase it to a point lying about 50.degree. C. above T.sub.g. The 
thermoplastic polyadducts according to the invention may be used by all 
techniques known for thermoplastic materials, like casting, extruding, 
injection molding, pressing, drawing. Instead of pure individual (single) 
components (diepoxide, diamine), also mixtures of the diamines and/or 
mixtures of various diepoxides may be used as long as the equivalency of 
the functional groups is maintained according to the invention. For 
instance, it is advantageous to use mixtures containing N,N'-dibenzyl 
derivatives of aromatic diamines in order to obtain polyadducts having 
glass transition temperatures above 80.degree. C. As a considerable 
improvement following U.S. Pat. No. 3,554,956, it was found that the 
method according to the present invention allows, without incurring any 
problems, the forming of polyadducts without the addition of any diluents 
so that shaped bodies may be created, like casts, gaskets, pressed shapes 
or laminates or plane shapes like surface coatings or laminants. These 
epoxide-amine-polyadducts show, due to their non-crosslinked structure, 
other properties than the known crosslinked epoxide resins. They show, 
when used as surface coatings, adhesives, gaskets and as components of 
polymers in reinforced and filled materials and compositions, particularly 
lower inner tension or stress and less brittleness, which is, in 
comparison to the known epoxide-amine-crosslinked material, a considerable 
advantage because the danger of the occurrence of tension or stress cracks 
is reduced. Such cracks are a common cause of mechanical and electrical 
failures and are the cause of poor ageing characteristics. The method of 
this invention also allows the formation of fibers or films directly from 
a molten polyadduct. 
The diepoxides used may be produced in known manner and also be purified by 
conventional methods like distillation, recrystallization or other 
methods. 
The diamines according to the invention are produced according to known 
synthetic methods, for instance by the reaction of dichloro-compounds with 
benzylamine or by the reaction of diprimary diamines with benzaldehyde and 
subsequent hydrogenation of the Schiff-bases. Several disecondary diamines 
are already commercially produced (e.g., N,N'-dibenzylethylenediamine). 
Others were synthesized according to known methods (Makromol. Chem. 17, 
77-130 (1955). Suitable disecondary diamines, having the structure DA are: 
N,N'-dibenzylethylenediamine/R'=--CH.sub.2 --CH.sub.2 --/ 
N,N'-dibenzyltetramethylenediamine-1,4/R'=--(CH.sub.2).sub.4 --/ 
N,N'-dibenzylhexamethylenediamine-1,6/R'=--(CH.sub.2).sub.6 --/ 
N,N'dibenzyl-2,2,4(2,4,4)trimethyl-hexamethylenediamine-1,6/R'=--CH.sub.2 
--C(CH.sub.3).sub.2 --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 --CH.sub.2 --/ 
N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8/R'=--(CH.sub.2 --CH.sub.2 
--O).sub.2 --CH.sub.2 --CH.sub.2 --/ 
N,N'dibenzyl-p-xylylenediamine/R'= 
##STR4## 
N,N'dibenzyl-2,7-bis(aminomethyl)-fluorene/R'= 
##STR5## 
N,N'-dibenzyl-4,4'-diaminodiphenylmethane/R'= 
##STR6## 
N,N'-dibenzyl-4,4'-diaminodicyclohexylmethane/R'= 
##STR7## 
N,N'-dibenzyl-but-2-ene-diamine-1,4/R'=--CH.sub.2 --CH.dbd.CH--CH.sub.2 
--/ 
N,N'-dibenzyl-2,5-bis(aminomethyl)thiophene/R'= 
##STR8## 
N,N'-diphenethylethylenediamine/R'=--CH.sub.2 --CH.sub.2 --/R=C.sub.6 
H.sub.5 --CH.sub.2 --CH.sub.2 -- 
N,N'-dibenzyl-1-phenylethylenediamine/R'=CH(C.sub.6 H.sub.5)--CH.sub.2 --/ 
Observing that the process of this invention does not lead to a crosslinked 
polyadduct, it is justified to call it surprising that 
N,N'-dimethylbenzylamine catalyzes as is well known crosslinking of 
epoxides while being structurally quite analogous to the 
nitrogen-containing polymer-chains of the present invention. According to 
the invention, the N,N'-dibenzyldiamines particularly are the most 
preferred addition partners for the preparation of non-crosslinked high 
molecular polyadducts. Extensive experiments showed that various 
substituents R, which did not belong to the aralkyl-species, caused 
crosslinking or lead to low molecular polyadducts only. 
Furthermore, it is most important, for the end uses of this invention, that 
the volume contraction after the addition of, e.g., 
2,2-bis(4-glycidyl-oxyphenyl)propane to the disecondary diamines DA of the 
invention is smaller than 5% (3-5%) of the volume of the mixture of the 
monomers. By adding partially reacted monomer mixtures of the invention 
and by admixture of fillers like silica gel or quartz powder, this effect 
of the polyaddition causing volume contraction may be still more reduced. 
In certain cases, casting or hot-pressing of the completely reacted 
thermoplastic polyadducts is able to reduce this change of volume down to 
the size of the thermal expansion of the polymers, a very desirable 
solution for various technical problems.

EXAMPLES OF THE INVENTION 
Example 1 
34.040 g crystalline 2,2-bis(4-glycidyloxyphenyl) propane (DDGE), melting 
at 42.5.degree. to 43.degree. C., are melted in a closable gastight, 
flat-bottomed flask. After cooling, 24.034 g N,N'-dibenzylethylenediamine, 
BP.sub.0.08 156.degree.-157.degree. C., n.sub.D.sup.20 =1.5652, are added. 
The mixture is stirred in an inert atmosphere, becoming fluid and 
homogeneous. Subsequently, the mixture is degassed in vacuo, again exposed 
to an inert gas and kept 72 hours at 80.degree. C. 
A colorless glassy solid polyadduct is obtained. T.sub.g (DSC-1, 
Perkin-Elmer) is 51.degree. C. 
It dissolves in THF, pyridine, toluene/cyclohexanone, chloroform/methanol. 
The relative molecular weight is found by vapor pressure to be 16,200 
(chloroform/methanol=4/1). The limiting viscosity value (25.degree. C., 
chloroform/methanol=4/1) is [n]=41.4 (in ml. g..sup.-1). 
The following elemental analysis was obtained after dissolving the 
polyadduct in toluene/cyclohexanone (4/1) and precipitation with petrol 
ether and drying of the colorless powder at 50.degree. C.: Calculated: C, 
76.52%; H, 7.64%; N, 4.82%. Found: C, 76.28%; H, 7.93%; N, 4.48%. 
Films and lacquer-like coatings were prepared from solutions of the 
polyadduct. The polyadduct softens at 80.degree. C. yielding a highly 
viscous mass, which may be fabricated according to known methods into 
films, rods and other shapes. 
If, after mixing and degassing, the polyreaction is carried out in a 
shaping vessel, for instance in a hollow Teflon cylinder, a round rod is 
obtained having good mechanical properties. 
Example 2 
N,N'-dibenzyl-hexamethylenediamine-1,6,BP.sub.0.2 189.degree.-193.degree. 
C.; MP: 30.5.degree. C.; n.sub.D.sup.20 =1.5452, is prepared from 
bis(benzylidene)-hexamethylenediamine-1,6 by reduction with sodium 
borohydride in ethanol as a solvent. The diamine is obtained, after 
repeated distillation, as a colorless oily liquid, which is homogeneous as 
proven by TLC (DC upon Silufol, flowing fluid ethanol/isobutylacetate/25% 
hydrous ammonia=10/10/3). 
Analysis: C.sub.20 H.sub.28 N.sub.2 (296.5). Calculated: C, 81.03%; H, 
9.52%; N, 9.45%. Found: C, 81.15%; H, 9.82%; N, 9.56%. 
10.700 g. crystalline 2,2-bis(4-glycidyloxyphenyl) propane, MP=42.5.degree. 
to 43.degree. C., colorless crystals, are mixed with 9.118 g 
N,N'-dibenzyl-hexamethylenediamine-1,6 and kept at room temperature for 24 
hours, and then maintained for 120 hours at 60.degree. C. After 24 hours, 
a relative molecular weight of 6500 is obtained, which rises to about 
12,000 within 100 hours. 
The product is a colorless, glassy solid material (T.sub.g =35.degree. C.), 
which begins to flow above 60.degree. without decomposition. The 
polyadduct is soluble in chloroform/methanol. Well adhering films can be 
cast from this solution. The polyadduct may be shaped thermoplastically. 
Example 3 
N,N'-dibenzyl-3,6-dioxa-octanediamine-1-8, BP.sub.0.1 =207.degree. to 
210.degree. C., n.sub.D.sup.20 =1.5406, is prepared from 
1,8-dichloro-3,6-dioxa-octane by reaction with benzylamine. For that 
purpose, 1 mole (187.1 g) 1,8-dichloro-3,6-dioxa-octane are added dropwise 
while stirring during one hour to 10 moles (1071.5 g) benzylamine. The 
mixture is heated for one hour at 140.degree. C. and further for 3 hours 
at 90.degree. C. After cooling, 4 moles (224 g) KOH are added as an 
aqueous 25% solution. The mixture is shaken vigorously in a separatory 
funnel. After the separation of the phases, the upper layer is separated, 
dried above solid potassium hydroxide and distilled in vacuo. Excess 
benzylamine is distilled off and the remaining liquid is fractionated. The 
diamine is colorless liquid, which is homogeneous as proven by TLC (DC 
upon Silufol, flowing fluid ethanol/isobutylacetate/25% aqueous 
ammonia=10/10/3); yield: 50%. 
C.sub.20 H.sub.28 N.sub.2 O.sub.2 (328.5). Calculated: C, 73.13%; H, 8.59%; 
N, 8.53%. Found: C, 73.14; H, 8.72%; N, 8.40%. 
Dihydrochloride: MP 189.5.degree. to 190.degree. C. 
C.sub.20 H.sub.30 N.sub.2 O.sub.2 Cl.sub.2 (401.4). Calculated: C, 59.85%; 
H, 7.53%; N, 6.98%; Cl, 17.67%. Found: C, 60.02%; H, 7.75%; N, 6.77%; Cl 
17,30%. 
10.000 g crystalline 2,2-bis(4-diglycidyloxyphenyl)-propane, 
MP=42.5.degree. to 43.degree. C., are mixed, as in example 1, with 9.439 g 
N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8, and allowed to stand for 24 
hours at room temperature and then heated for 120 hours at 60.degree. C. A 
faintly yellow glassy material results (relative molecular weight=10,000, 
T.sub.G =14.degree. C.) which begins to flow above 45.degree. C. without 
decomposition. The polyadduct is soluble in chloroform/methanol. Well 
adhering films may be poured from such solutions. The polyadduct may be 
shaped by known methods. 
Example 4 
N,N'-dibenzyl-p-xylylenediamine (BP.sub.0.2 =130.degree. C., MP=53.degree. 
C., n.sub.D.sup.60 =1.5800) is prepared from p-xylylene-dichloride by 
reaction with benzylamine. For that purpose, 1 mole (175.0 g) 
p-xylylenedichloride is added during one hour drop-wise with stirring to 
10 moles (1071.5 g) benzylamine and kept for 2 hours at 150.degree. C. 
After cooling, 4 moles (224 g) potassium hydroxide are added as a 25% 
aqueous solution. Two phases form; the upper is removed from a separatory 
funnel and dried with potassium hydroxide until it becomes a clear liquid. 
The liquid is distilled in vacuo while protected by nitrogen. At 
68.degree. C. and 10 Torr benzylamine distills off, and, at 130.degree. 
C., 0.2 Torr, the diamine distills off. 
The diamine, a pale yellow oily liquid, is separated and crystallizes on 
standing as colorless crystals. It is identified by TLC as a homogeneous 
substance (DC upon Silufol, flowing fluid ethanol/isobutylacetate/25% 
aqeous ammonia 7/10/2); yield: 71%. 
C.sub.22 H.sub.24 N.sub.2 (316.4). Calculated: C, 83.50%; H, 7.64%; N, 
8.85%. Found: C, 84.12%; H, 7.88%; N, 8.73%. 
19.439 g crystalline 2,2'bis(4-glycidyloxyphenyl) propane (mp=42.5.degree. 
to 43.degree. C., colorless crystals) are, as described in example 1, 
heated for 50 hours at 80.degree. C. with 17.674 g 
N,N-dibenzyl-p-xylylene-diamine. A polyadduct (rel. molecular 
weight=10,000, yellowish, glassy, T.sub.G =57.degree. C.) is obtained, 
which begins to flow above 100.degree. C. without decomposing. Solutions 
of the polyadduct yield well adhering films. The polyadduct may be shaped 
using methods known in the plastics industry. 
Example 5 
4,4'-bis(N-benzylamino)-diphenylmethane (MP=115.degree. C.) is prepared by 
reacting 4,4'diamino-diphenylmethane with benzyl-alcohol and potassium 
hydroxide at 270.degree. C. After recrystallization in ethanol, the 
diamine occurs as a colorless crystalline product which is homogeneous as 
found by TLC (DC upon Silufol, flowing fluid ethanol, isobutylacetate, 25% 
aqueous ammonia 7/10/2). 
C.sub.27 H.sub.26 N.sub.2 (378.5). Calculated: C, 85.67%; H, 6.92%; N, 
7.41%. Found: C, 85.86%; H, 6.98%; N, 7.40%. 
10.508 g. crystalline 2,2'-bis(4-glycidyloxyphenyl) propane 
(MP=42.5.degree. to 43.degree. C., colorless crystals) are heated for 50 
hours at 105.degree. C. with 11.675 g 
4,4'-bis(N-benzylamino)-diphenylmethane. After 20 hours, a relative 
molecular weight of 5000 is obtained, which rises after another 30 hours 
to about 10,000. 
A yellow brown glassy solid (T.sub.G =95.degree. C.) is obtained, which 
begins to flow without decomposing above 120.degree. C. 
The polyadduct is soluble in chloroform/methanol. These solutions yield 
well adhering films. The polyadduct may be shaped like well known 
thermoplastic polymers. 
EXAMPLE 6 
N,N'-dibenzyl-2,2,4(2,4,4)-trimethylhexamethylenediamine-1,6 (BP.sub.0.15 
=200.degree. C.) is prepared by the reaction of 
2,2,4(2,4,4)-trimethylhexamethylenediamine-1,6 with benzaldehyde and 
subsequent reduction with NaBH.sub.4, as in Example 2. 
C.sub.23 H.sub.34 N.sub.2 (338.5). Calculated: C, 81.60%; H, 10.12%; N, 
8.28%. Found: C, 81.72%; H, 10.19%; N, 8.29%. 
10,000 g crystalline 2,2'-bis(4-glycidyloxyphenyl) propane were, as 
described in Example 1, heated for 72 hours at 60.degree. C. with 9.898 g 
N,N'-dibenzyl-2,2,4(2,4,4)-trimethylhexamethylenediamine-1,6. A soluble, 
thermoplastically shapeable polyadduct is formed (T.sub.g =36.degree. C., 
rel. molecular weight: 8200).