Novel polymers containing amide moieties are produced by reaction of a spirodilactam precursor selected from 4-oxoheptanedioic acid compounds or 1,6-dioxa [4.4] spirodilactones, a primary diamine and an aromatic, aliphatic or alicyclic dicarboxylic acid compound. The polymer products have relatively high glass transition temperature.

FIELD OF THE INVENTION 
This invention relates to a class of novel polyamide polymers characterized 
by the presence of amide linkages within the polymer chain. More 
particularly, the invention relates to a linear, alternating polymer in 
which moieties derived from a primary diamine alternate with moieties 
derived from a dicarboxylic acid compound and with moieties of a 1,6-diaza 
[4.4] spirodilactam. 
BACKGROUND OF THE INVENTION 
The class of polyamide polymers is broadly well known in the art. A 
commercial example of this class of polymers is the polyamide 
illustratively produced from hexamethylenediamine and adipic acid known as 
Nylon 66. The nature of the reaction product of a carboxylic acid or 
related compound will vary, however, depending upon the chemical nature of 
the acid compound and the amine. 
The reaction of a ketobenzoic acid, i.e., benzoylbenzoic acid, and diamines 
is shown by Hovey et al, U.S. Pat. No. 2,149,678 and U.S. Pat. No. 
2,195,570. The reaction of aromatic dicarboxylic acids and photosensitive 
diamine compounds is shown by Nakama et al, U.S. Pat. No. 4,595,745 
Caldwell et al. U.S. Pat. No. 3,408,334, describe the reaction of 
dicarboxylic acids and diamines in the presence of a tin compound as 
catalyst. Reaction of .alpha.,.beta.-unsaturated aromatic dicarboxylic 
acids and primary and secondary diamines is disclosed by Conciatori, U.S. 
Pat. No. 3,637,602. The production of polyamideimides by reactions 
including that of a diacid and polyamides is shown by Emerick et al, U.S. 
Pat. No. 3,778,411. The use of a dicarboxylic acid of additional 
functionality, 4-oxoheptanedioic acids, in the production of polymers is 
shown by Ferstandig, U.S. Pat. No. 2,987,502, but reaction was with a 
polyhydroxylic alcohol and the product was a polyester. U.S. Pat. No. 
2,279,752 describes linear polyamides having recurring --NHRCO-- units 
such that a keto group, present in at least one reactant, is in the 
divalent organic radical separating the recurring amine units of the 
polyamide. 
A class of compounds that functions in some ways similar to dicarboxylic 
acids is the class of 1,6-dioxa [4.4] spirodilactones. The simplest member 
of this class, 1,6-dioxaspiro[4.4]nonane-2,7-dione, is known and has been 
prepared, among other procedures, by the process of Pariza et al, 
Synthetic Communications, Vol. 13(3). pp. 243-254 (1983). These 
spirodilactones have demonstrated utility as curing agents to produce 
cured compositions which do not shrink upon curing. This property probably 
results from opening of the spirodilactone rings during the curing 
process. It is characteristic of the spirodilactone ring system that 
reaction with active hydrogen compounds tends to produce ring-opened 
products, as further evidenced by the above Pariza et al article. See also 
Cowsar et al, U.S. Pat. No. 4,064,086 One reaction of 
1,6-dioxaspiro[4.4]nonane-2,7-dione in which the ring system is maintained 
is described and claimed in U.S. Pat. No. 4,939,251 wherein the 
spirodilactones are reacted with hydroxy-containing primary amino 
compounds to produce monomeric substituted spirodilactams. 
The polyamide polymers of the present invention are terpolymers as are many 
other polymeric polyamides. However, because of the relatively low melting 
point or glass transition temperatures exhibited by many polymeric 
polyamides, the thermoplastic polyamides are not generally useful as 
engineering thermoplastics where exposure to elevated temperatures is 
likely to be encountered. It would be of advantage to provide novel 
polymeric polyamides having relatively high glass transition temperatures. 
It would be of further advantage to provide processes employing 
dicarboxylic acid compounds or alternatively spirodilactones to produce 
such polymeric polyamides. 
SUMMARY OF THE INVENTION 
The present invention provides a linear, alternating terpolymer which 
contains amide linkages within the polymer chain. More particularly, the 
invention provides a class of novel polyamide polymers wherein moieties 
corresponding to the non-amino portion of a primary diamine alternate with 
moieties of an amide derived from an aromatic, aliphatic or alicyclic 
dicarboxylic acid compound and with moieties of a 1,6-diaza [4.4] 
spirodilactam. The invention additionally provides a method for the 
production of such polymers.

DESCRIPTION OF THE INVENTION 
The novel polyamide polymers of the invention are the reaction product of a 
primary diamine, an aromatic, aliphatic or alicyclic dicarboxylic acid 
compound and a spirodilactam precursor. The spirodilactam precursor is a 
compound which, under the conditions of the process of the invention, 
reacts with the primary diamine reactant to produce the moiety of a [4.4] 
spirodilactam having spiro ring nitrogen atoms in the 1- and 6-spiro ring 
positions and is connected through the nitrogen atoms to the moieties 
derived from the primary diamine. In one embodiment of the invention the 
spirodilactam precursor is a ketodiacid compound and in another embodiment 
of the invention the spirodilactam precursor is an analogous 
spirodilactone. 
In the embodiment wherein the spirodilactam precursor is a ketodicarboxylic 
acid compound, the acid compound is a ketodicarboxylic acid compound 
having two carbon atoms between the keto group and each carboxy function. 
In other terms, the ketodicarboxylic acid is a 4-oxoheptandioic acid 
compound. Although a variety of substituents in addition to the keto group 
and the carboxy functions are suitable for use in the process of the 
invention, the preferred 4-oxoheptanedioic acid compounds have up to 30 
carbon atoms inclusive and are represented by the formula 
##STR1## 
wherein A independently is hydroxy, alkoxy, preferably lower alkoxy of up 
to 4 carbon atoms inclusive, or halo, preferably the middle halogens, 
chloro or bromo. The term Z independently is &gt;C(Z').sub.2 in which Z' 
independently is hydrogen, lower alkyl, preferably methyl, halo, 
preferably the lower halogens fluoro or chloro, or aryl of up to 10 carbon 
atoms, preferably phenyl, or Z is such that adjacent Z groups form a ring 
system Z" of from 1 to 2 rings, each ring having from 5 to 7 ring atoms up 
to two of which are heteroatoms selected from nitrogen, oxygen or sulfur 
with the remainder of the ring atom being carbon atoms, there being up to 
14 carbon atoms in each Z", two of which ring carbon atoms form a bridge 
between the spiro and/or the carbonyl carbon atom connected by the 
adjacent Z groups. When adjacent Z groups taken together form a ring 
system, Z" is otherwise hydrocarbyl containing only atoms of carbon and 
hydrogen besides any heteroatoms present or is substituted hydrocarbyl 
additionally containing other atoms present in the form of monovalent, 
inert, carbon atom substituents, e.g., halo atoms, preferably the middle 
halogens chloro or bromo, alkyl of 1 to 4 carbon atoms, or the like. 
Preferably, each Z" is 1 aromatic ring. 
In one embodiment employing the ketodicarboxylic acid compound as the 
spirodilactam precursor, each Z moiety is &gt;C(Z').sub.2 and the ketodiacid 
compound is an acyclic 4-oxoheptanedioic acid compound, i.e., a 
4-oxoheptanedioic acid compound free from fused, cyclic substituents. Such 
4-oxoheptanedioic acid compounds are represented by the formula 
##STR2## 
wherein A and Z' have the previously stated meanings. These 
4-oxoheptanedioic acid compounds include 4-oxoheptanedioic acid, dimethyl 
4-oxoheptanedioic, 2,6-dimethyl-4-oxoheptanedioic acid, 
2,3,5,6-tetramethyl-4-oxoheptandioyl chloride, di-n-propyl 
2,6-di-n-butyl-4-oxoheptandioyl chloride, di-n-propyl 
2,6-di-n-butyl-4-oxoheptanedioate, 
7-carbomethoxy-3,3,5,5-tetramethyl-4-oxoheptanoic acid and the like. The 
preferred compounds of formula Ia are those wherein each Z' is hydrogen or 
methyl, especially hydrogen, and each A is hydroxy or alkoxy, especially 
hydroxy. 
These ketodiacid compounds are known compounds or are prepared by known 
methods. Certain of the esters of formula Ia, i.e., the compounds wherein 
each A is alkoxy and at least one Z' on each carbon atom adjacent to a 
carboxy function is hydrogen, are produced by reacting formaldehyde with 
an .alpha.,.beta.-ethylenically unsaturated carboxylic acid ester such as 
methyl acrylate or ethyl methacrylate. The reaction is conducted in the 
presence of a catalyst system which comprises a thiazolium salt and a 
tertiary amine and produces the 4-oxoheptanedioate compound in good yield. 
This process is described and claimed in greater detail in U.S. Pat. No. 
4,800,231 incorporated herein by reference. Conversion of the esters 
thereby obtained to corresponding free acids or acid halides is by 
conventional methods as is the general interconversion of the acids, 
esters or acid halides of formula Ia. 
In a second embodiment of the ketodiacid as the spirodilactam precursor, 
the 4-oxoheptanedioic acid compound is cyclic, that is, incorporates 
cyclic substituents between the keto group and the carboxy functions, 
i.e., the adjacent Z moieties form a cyclic ring system Z". Such 
ketodicarboxylic acid compounds are represented by the formula 
##STR3## 
wherein A and Z" have the previously stated meanings. Illustrative of such 
cyclic ketodiacid compounds are di(2-carboxycyclohexyl) ketone. 
di(2-carboxyphenyl) ketone, di(2-carbopropoxycyclo-4-pentenyl) ketone, 
di(2-chlorocarbonylphenyl) ketone, di(2-carboxypyridyl) ketone, 
2-carboxyphenyl N-methyl-3-carboxy-2-pyrryl ketone, 
di(3-carboethoxy)-2-morpholyl ketone, di(2-carbomethoxy-3-chlorophenyl) 
ketone and the like. The preferred ketodiacid compounds with cyclic 
substituents are those compounds of from 5 to 6 ring atoms and up to 1 
nitrogen and/or oxygen heteroatom. Most preferred as a cyclic substituent 
is benzo. 
The cyclic ketodiacid compounds of formula Ib are known compounds or are 
produced by known methods such as the method of U.S. Pat. No. 1,999,181 or 
the method of Cava et al, J. Am. Chem. Soc., 77, 6022 (1955), incorporated 
herein by reference or the like. 
In yet another embodiment of the ketodiacid compound as the spirodilactam 
precursor, the ketodiacid compound incorporates one cyclic substituent 
with the remainder of the Z moieties being acyclic, i.e., the compounds 
represented by the formula 
##STR4## 
wherein A, Z' and Z" have the previously stated meanings. Such ketodiacids 
of one cyclic moiety are illustrated by 3-(2-carboxybenzoyl)propionic 
acid, 3-(3-carboethoxy-2-pyridyloyl)-2-ethylpropionic acid, ethyl 
3(2-carboxy-4-methylbenzoyl)propionate, 3-(2-carboxybenzoyl)butyrl 
chloride and the like. The ketodiacids of formula Ic are known compounds 
or are produced by known methods. For example, 2-carbomethoxybenzaldehyde 
reacts with methyl acrylate according to the general teachings of U.S. 
Pat. No. 4,800,231 to produce methyl 3-(2-carbomethoxybenzoyl)propionate. 
In a second embodiment of the process of the invention the spirodilactam 
precursor is a 1.6-dioxaspiro[4.4]nonane-2.7-dione compound wherein the 
spirodilactone ring system is substituted with hydrogen, alkyl, halo or 
aryl, or the ring system incorporates fused ring substituents which 
include the 3- and 4- spiro ring positions and/or the 8- and 9- spiro ring 
positions. One class of such 1,6-dioxa [4.4] spirodilactones is 
represented by the formula 
##STR5## 
wherein Z has the previously stated meaning. 
In the embodiment of these spirodilactam precursors wherein each Z is 
acyclic, the spirodilactone is represented by the formula 
##STR6## 
wherein Z' has the previously stated meaning. Illustrative of such 
spirodilactones are 1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3.8-dimethyl-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,4,8,9-tetramethyl-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,3,8,8-tetramethyl-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,3,4,4,8,8,9,9-octamethyl-1,6-dioxospiro[4.4]nonane-2,7-dione and 
3,4,8,9-tetrafluoro-1,6-dioxaspiro[4.4]nonane-2,7-dione. Preferred 
spirodilactones of the formula IIa are those wherein at least one Z' of 
each Z'-substituted carbon atom is hydrogen and further preferred are the 
spirodilactones of formula IIa wherein each Z' is hydrogen. The compounds 
of formula IIa are known compounds or are produced by known methods such 
as by the process of Pariza et al, Synthetic Communications, Vol. 13(3), 
pp. 243-254 (1983), incorporated herein by reference. 
In the embodiment of the invention wherein the spirodilactone of formula II 
incorporates one cyclic substituent fused to each spiro ring, the 
spirodilactones are represented by the formula 
##STR7## 
wherein Z" has the previously stated meaning. Typical compounds of formula 
IIb are 3,4,8,9-dibenzo-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,4,8,9-dibenzo- 1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,4,8,9-di(cyclopentano)-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,4,8,9-di(4-methylbenzo)-1,6-dioxaspiro[4.4]nonane-2,7-dione and 
3,4,8,9-di(pyrido)-1,6-dioxaspiro[4.4]nonane-2,7-dione. These compounds 
are known compounds or are produced by known methods, for example, the 
process of the above Cava et al article or the process of U.S. Pat. No. 
1,999,181. 
In the embodiment where the spirodilactam precursor is a spirodilactone 
incorporating a fused cyclic substituent in one of the spiro rings but the 
other spiro ring is free of fused cyclic substituents, the spirodilactones 
are represented by the formula 
##STR8## 
wherein Z' and Z" have the previously stated meanings. Such 
spirodilactones are illustrated by 
3-methyl-8,9-benzo-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
3,4-benzo-1,6-dioxaspiro[4.4]nonane-2,7-dione and 
3,3,4,4-tetramethyl-8,9-(2-morpholyl)-1,6-dioxaspiro[4.4]nonane-2,7-dione. 
The spirodilactones of the above formula IIc are known compounds or are 
produced by known methods such as the dehydration of the corresponding 
ketodiacid compound. By way of specific illustration, 
3,4-benzo-1,6-dioxaspiro[4.4]nonane-2,7-dione is produced by dehydration 
of 3-(2-carboxybenzoyl)propionic acid through application of heat. 
In general, the preferred spirodilactones for use as spirodilactam 
precursors are hydrocarbon except for the oxygen atoms of the lactone 
moieties, particularly those spirodilactones which are free from fused 
cyclic substituents (formula IIa) or those which have a fused cyclic 
substituent on each of the spiro rings (formula IIb). The spirodilactone 
1,6-dioxaspiro[4.4]nonane-2,7-dione is an especially preferred member 
among members of the former class whereas 
3,4,8,9-dibenzo-1,6-dioxaspiro[4.4]-nonane-2,7-dione is an especially 
preferred member of the latter class. 
The spirodilactam precursor is reacted, according to the process of the 
invention, with an aromatic, alicyclic or aliphatic dicarboxylic acid 
compound and a primary diamine or an acid addition salt thereof. Primary 
diamines are those organic compounds which have two primary amino groups, 
i.e., --NH.sub.2 groups, as carbon atom substituents. While reaction to 
produce the polyamideimide polymers of the invention will take place with 
a variety of primary diamines of varying structure, best results are 
obtained in the process of the invention of the two amino groups are not 
located on adjacent carbon atoms, that is, at least three atoms separate 
the two primary amino groups. One such class of primary diamines comprises 
diamines of up to 30 carbon atoms inclusive which are represented by the 
formula 
EQU H.sub.2 N--R--NH.sub.2 (.HY).sub.m (III) 
wherein m is 0 or 1; HY is an acid which forms a salt with the amine, 
including both inorganic and organic acids which do not interfere with the 
reaction, such as hydrohalogenic acids, such as hydrochloric and 
hydrobromic; sulfur acids, such as sulfuric or sulfonic; phosphorus acid, 
such as phosphoric or phosphonic; and organic acids, such as oxalic acid 
and the like, preferably Y is halogen, e.g., fluorine, chlorine, bromine 
or iodine, but is preferably middle halogen chlorine or bromine; R is a 
divalent organic radical of up to 30 carbon atoms inclusive and is 
divalent alkylene or divalent arylene of from 1 to 2 aromatic rings 
inclusive which, when two aromtic rings are present, incorporates rings 
which are fused or which are connected by a moiety X wherein X is a direct 
valence bond, alkylene of up to 8 carbon atoms inclusive, oxy, thio, 
sulfonyl, carbonyl, dioxyphenylene, i.e. 
##STR9## 
with the proviso that the two amino groups are not located on adjacent 
atoms. R is preferably hydrocarbyl containing only atoms of carbon and 
hydrogen besides the additional atoms of divalent linking groups but may 
also be substituted hydrocarbyl containing other atoms such as halogen, 
preferably middle halogen, as inert monovalent carbon atom substituents. 
Illustrative of the alkylene-containing primary diamines of formula III 
include trimethylenediamine, tetramethylenediamine, hexamethylenediamine, 
octamethylenediamine, 1 7-diamino-4-methyloctane, 1,4-diaminocyclohexane, 
di(4-amino-cyclohexyl)methane, dodecamethylenediamine, 
1,6-diamino-3-4-diethylhexane and the like. Arylene diamines of the above 
formula III include 1,4-phenylenediamine, 2,4-toluenediamine, 
4,4'-diaminobiphenyl, 1,5-diaminonaphthalene, di(3-aminophenyl) ether, 
di(4-aminophenyl)methane, 2,2-di(3-amino-4-methylphenyl)propane, 
di(4-amino-2-ethylphenyl) sulfone, di(3-amino-4-bromophenyl) ketone, 
di(2-aminophenyl) sulfide, 1,3-di(3-aminophenyloxy)benzene, 
2,2-di[4-(4-aminophenyloxy)phenyl)]propane, 
4,4,-di(4-aminophenyloxy)biphenyl and the like. The preferred primary 
diamines of the above formula III are those wherein R is divalent arylene 
and which are otherwise hydrocarbyl execpt for any additional atoms of 
divalent linking groups. Particularly preferred are the 
di(aminophenyl)alkanes, especially the di(4-aminophenyl)alkanes, such as 
di(4-aminophenyl)methane. 
In the reaction of the invention the spirodilactam precursor and the 
primary diamine react with an aromatic, aliphatic or alicyclic 
dicarboxylic acid compound which will suitably have two of the carboxy 
functions on non-adjacent carbon atoms of the same aromatic ring as free 
carboxyl groups (--CO.sub.2 H groups), as halides thereof or together as a 
linear anhydride moiety. A preferred class of acids comprises aromatic, 
alicyclic, or aliphatic dicarboxylic acid compounds having up to 30 carbon 
atoms in each acid compound and up to 3 rings, inclusive, including those 
represented by the formula 
EQU HO.sub.2 C--R'--X'(R').sub.r --CO.sub.2 H (IV) 
wherein X' is X, R' is an aromatic, aliphatic or alicyclic divalent group 
of up to 15 carbon atoms and from 1 to 2 rings and r is 0 or 1. R' is 
preferably hydrocarbyl but may be substituted hydrocarbyl containing 
additional atoms as inert carbon atom substituents, e.g., halogen atoms 
and preferably the middle halogens, alkyl of 1 to 4 carbon atoms, and the 
like. As mentioned above, acid halides or anhydrides are also suitable 
acid compound reactants. 
Illustrative of the aromatic, aliphatic or alicyclic dicarboxylic acid 
compounds which are useful in the process of the invention include adipic 
acid, phthalic acid, 2,3-naphthalenedicarboxylic acid, terphthalic acid 
chloride, 2,2-di(4-carboxyphenyl)propane, isophthalic acid, phthalic 
anhydride, 4,4',-biphenyl ether dicarboxylic acid;, bis(4-carboxyphenyl) 
sulfone, 2,6-naphthalene-dicarboxylic acid, furandicarboxylic acid, 
pyridinedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, malonic acid, 
oxalic acid, cyclopentanedicarboxylic acid, pimelic acid and the like or 
any of the acids disclosed in U.S. Pat. Nos. 4,866,155, 4,876,327, 
4,868,062 and 4,829,144, the disclosures of which are incorporated herein 
by reference. In general hyrocarbon R' groups are preferred as the 
reactant of formula IV, and particularly preferred are those where r is 0 
and X' is a direct valence bond. Such aromatic dicarboxylic acid compounds 
of one aromatic ring give best results, particularly isophthalic acid. 
The reaction of the spirodilactam precursor, the primary diamine and the 
dicarboxylic acid compound is conducted in the liquid phase in the 
presence of an inert reaction diluent. Diluents which are liquid at 
reaction conditions and in which the reactants are at least partially 
soluble at reaction temperature are satisfactory. Suitable diluents 
include the N-alkylamides such as N,N-dimethylformamide, 
N,N-dimethylacetamide and N-methyl-2-pyrrolidone, phenols such as phenol 
and m-cresol, sulfur-containing diluents such as dimethylsulfoxide, 
sulfolane or the like. 
The polymerization is conducted by contacting the reactants in a suitable 
reactor under polymerization conditions and maintaining reactant contact 
by conventional methods such as shaking or stirring. The relative 
properties of the reactants may vary within certain limits and the 
properties of the resulting polymer will vary accordingly. The molar ratio 
of spirodilactam precursor to dicarboxylic acid compound is suitably from 
about 95:5 to about 5:95 but preferably will be from about 4:1 to about 
1:4. As the primary diamine reacts with both the spirodilactam precursor 
and the dicarboxylic acid compound, the molar quantity of the primary 
diamine should preferably be about equal to the total molar quantity of 
the other two reactants. Molar ratios of primary diamine to total 
spirodilactam precursor plus dicarboxylic acid compound from about 5:1 to 
about 1:5 are satisfactory but molar ratios of from about 2:1 to about 1:2 
are preferred. 
The polymerization is conducted at an elevated temperature. Reaction 
temperatures from about 80.degree. C. to about 250.degree. C. are suitable 
with preferred reaction temperatures being from about 120.degree. C. to 
about 200.degree. C. A suitable reaction pressure is one which will 
maintain the reaction mixture in a liquid phase. Such pressures are 
typically up to about 20 atmospheres but more often are from about 0.8 
atmospheres to about 10 atmospheres. During reaction, any water present or 
formed is preferably removed by conventional procedures such as selective 
extraction or distillation, preferably azeotropic distillation with a 
portion of the reaction diluent or with a second reaction diluent with 
which water forms an azeotrope, e.g., toluene or ethylbenzene. Subsequent 
to reaction, the polymer product is recovered by conventional methods such 
as solvent removal, extraction or precipitation. 
The polymer product is a polyamide containing amide linkages. The amide 
linkages result from spirodilactam moiety formation or from reaction of 
the carboxy functions of the carboxylic acid compound with the primary 
diamine. The polymer product thus contains moieties of the non-amino 
portion of a primary diamine alternating with (1) a 1,6-diaza [4.4] 
spirodilactam moiety connected to the remainder of the polymer chain 
through the spiro ring nitrogen atoms and with (2) a moiety of the 
aromatic or aliphatic dicarboxylic acid compound derived by the loss of 
hydroxyl groups or anhydride oxygen equivalent. In terms of the reactants 
as depicted above (formulas I or II, III and IV) the polymer products are 
represented by the repeating formula V 
##STR10## 
wherein Z, R, R', X and r have the previously stated meaning and the ratio 
of m:n is from about 95:5 to about 5:95, preferably from about 4:1 to 
about 1:4. Of particular interest are the polymers of formula V having a 
molecular weight from about 10,000 to about 100,000. 
The nomenclature of the polymer products of the formula V is not easily 
determined because of the complexity thereof, but the identity of the 
products will be apparent from the above discussion of the reactants and 
consideration of the formula for the products as depicted above. 
Illustrative of such products is the polymer illustratively produced from 
4-oxoheptanedioic acid or 1,6-dioxaspiro[4.4]nonane-2,7-dione, 
di(4-aminophenyl)methane and terephthaloyl acid chloride, the polymer 
product produced from 2,3,5,6-tetramethyl-4-oxoheptanedioic acid or 
3,4,8,9-tetramethyl-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
p-phenylenediamine and adipic acid and the polymer illustratively produced 
from di(2-carboxyphenyl)ketone or 
3,4,8,9-dibenzo-1,6-dioxaspiro[4.4]nonane-2,7-dione, 
2,2-di(4-aminophenyl)propane and phthalic anhydride. Preferred polymer 
products are those of the above formula V wherein Z is &gt;C(Z').sub.2 in 
which Z' is hydrogen or methyl, R is divalent arylene, r is 0 and R' is a 
direct valence bond. 
The polymer product is a thermoplastic polymer of relatively high glass 
transition temperature, typically over 150.degree. C. and often over 
250.degree. C. The polymer product is processed by the conventional 
techniques associated with thermoplastics such as injection molding and 
extrusion into sheets, films, fibers and shaped articles which demonstrate 
good resistance to common solvents. Because of the relatively high glass 
transition temperatures exhibited by the polymers they are useful as 
engineering thermoplastics where elevated temperatures are likely to be 
encountered. Such applications include the production of containers for 
food and drink and base materials for electrical and electronic 
applications. 
The invention is further illustrated by the following Illustrative 
Embodiment which should not be construed as limiting the invention. 
Illustrative Embodiment 
A mixture of 1.56 g (0.01 mole) of 1,6-dioxaspiro[4.4]nonane2,7-dione. 1.66 
g (0.01 mole) of isophthalic acid, 39.6 g (0.02 mole) of 
di(4-aminophenyl)methane. 10 ml of pyridine and 40 ml of 
N-methyl-2-pyrrolidone was heated, while being stirred, and the water 
present or formed was removed by azeotropic distillation. When the water 
removal was complete the temperature of the mixture was raised to 
170.degree.-180.degree. C. and maintained at that temperature for 12 
hours. After cooling, the resulting mixture was poured into methanol. The 
precipitated polyamide polymer product was and dried in a vacuum over at 
170.degree. C. for 24 hours. The nuclear magnetic resonance spectra were 
consistent with a polymer having diphenylenemethane units alternating with 
units of a 1,6-diaza [4.4] spirodilactam and units of 
##STR11##