A novel class of cyano-, cyanoalkyl-, carboxy- or carboxyalkylaryl-substituted 1,6-diaza [4.4] spirodilactams, having a cyano-, cyanoalkyl-, carboxy- or carboxyalkylaryl substituent attached to each spiro ring nitrogen atom, are useful for the preparation of polyesters and polyamides.

FIELD OF THE INVENTION 
This invention relates to a novel class of spirodilactams having cyano- or 
carboxy-containing moities on aryl substituents on the spiro ring nitrogen 
atoms and to polyesters and polyamides therefrom. 
BACKGROUND OF THE INVENTION 
Cyano- and carboxyaryl compounds are well-known classes of compounds that 
can be used as starting materials to make polyester and polyamide 
polymers, having a variety of uses. 
On some occasions, the polyester and polyamide products which provide the 
more desirable properties, particularly in high temperature applications, 
are produced from derivatives of aromatic carboxy-terminated compounds 
wherein some or all of the rings share common atoms with other rings of a 
polycyclic structure. 
It would be of advantage to provide a novel class of cyano- and carboxy 
compounds having a plurality of rings within the molecular structure and 
have such derivatives be used to produce polyester and polyamide polymers. 
SUMMARY OF THE INVENTION 
The present invention relates to a novel class of cyano-, cyanoalkyl-, 
carboxy- or carboxyalkylaryl-substituted [4.4] spirodilactams and to 
polyesters and polyamines thereof, including from 
1,6-diazaspiro[4,4]nonane-2,7-diones having cyano-, cyanoalkyl-, carboxy- 
or carboxyalkylaryl substituents on the ring nitrogen atoms of the 
spirodilactam ring system. 
DESCRIPTION OF THE INVENTION 
The novel compounds of the invention are cyano-, cyanoalkyl-, carboxy- or 
carboxyalkylaryl-substituted 1,6-diazaspiro[4.4]-nonane-2,7-dione having 
the cyano-, cyanoalkyl-, carboxy- or carboxyalkylaryl substituents on the 
spiro ring nitrogen atoms and optionally having acyclic or cyclic 
substituents in the 3-, 4-, 8- and 9-positions of the spiro ring system. 
Accordingly, the invention is directed to a cyano-, cyanoalkyl-, carboxy- 
or carboxyalkylaryl-substituted spirodilactam, comprising a spirodilactam 
compound having nitrogen atoms in the 1- and 6-positions of the spiro ring 
system and having a cyano-, cyano-alkyl-, carboxy- or carboxyalkylaryl 
substituent on each spiro ring nitrogen atom, said spirodilactam compound 
comprising up to about 60 carbon atom. As generically used herein, 
"carboxyaryl" or "carboxyalkylaryl" means an aryl or alkylaryl group 
substituted by a carboxylic acid group --C(O)OH or by a functional 
derivative of said carboxy moiety selected from acid chlorides and 
bromides, anhydrides, amides, esters or salts. 
The substituted spirodilactam of the invention includes those of the 
formula I 
##STR1## 
wherein Q is --CN or is --C(O)Y in which Y is chlorine or bromine, or Y is 
OY' in which Y' is hydrogen, a salt-forming cation or an unsubstituted or 
inertly substituted aliphatic or aromatic group of from 1 to 20 carbon 
atoms, or Y is --N(Y").sub.2 in which each Y" independently is a hydrogen 
atom or an unsubstituted or inertly substituted aliphatic or aromatic 
group of from 1 to 20 carbon atoms, Z is independently &gt;C(Z') in which Z 
independently is hydrogen, lower alkyl of up to 4 carbon atoms, preferably 
methyl, halogen, preferably the lower halogens, fluoro or chloro, or aryl, 
preferably phenyl, or Z is such that the two adjacent Z groups, taken 
together form a ring system Z" of 1 to 3 rings, each ring having from 5 to 
7 ring atoms, up to two of which are heteroatoms selected from nitrogen 
atoms, oxygen atoms or sulfur atoms with the remainder of the ring atoms 
being carbon atoms, there being up to 15 carbon atoms in each Z", two of 
which ring carbon atoms form a bridge between the two carbon atoms (spiro 
and carbonyl carbon atoms) connected by the adjacent Z groups. In the 
above formula I, R independently is an aromatic group of up to 18 carbon 
atoms which can have up to 4, preferably 2, aromatic rings, inclusive; R' 
is an aliphatic group of up to 10 carbon atoms, inclusive. Each of R and 
R' is hydrocarbyl, i.e., contains only atoms of carbon and hydrogen, or is 
substituted hydrocarbyl containing additional atoms in the form of inert 
substituents, such as halogen, preferably the middle halogens, chlorine or 
bromine. The terms n and r in the above formula I each independently is 0 
or 1 and X is a direct valence bond, or X is alkylene of up to 8 carbon 
atoms, inclusive, oxy, thio, sulfonyl, carbonyl, dioxyphenylene, 
2,2-di(oxyphenyl)propane, dioxyphenyl sulfone or dioxydiphenylene. 
When Y' is a salt-forming cation, it is selected from alkali metals, 
alkaline earth metals, aluminum, heavy metals, such as copper, silver, 
nickel and the like, ammonia or a tetrahydrocarbylammonium compound in 
which the total number of carbon atoms in the hydrocarbyl groups is 
between 4 and 70 carbon atoms. The hydrocarbyl groups can be alkyl, aryl, 
aralkyl and the like. Preferably, the hydrocarbyl groups are selected from 
alkyl groups containing from 1 to 10 carbon atoms and aralkyl groups 
containing from 7 to 10 carbon atoms. 
Q is preferably --C(O)Y in which Y is chlorine, OY' in which Y' is hydrogen 
or alkyl of from 1 to 4 carbon atoms, e.g., methyl or ethyl or N(Y").sub.2 
in which each Y" is a hydrogen atom. 
Spirodilactams of a considerable variety of structures are included in the 
compounds of the invention. In the embodiment of the invention wherein Q 
is --C(O)OH and the moieties of the above compounds of the formula I are 
not part of a fused ring system and are therefore acyclic, i.e., Z is 
&gt;C(Z').sub.2, the spirodilactam is illustrated by 
1,6-di(4-carboxyphenyl)-1,6-diazaspiro[4.4]nonane-2,7-dione, 
1,6-di(3-carboxy-4-chlorophenyl)-3,8-dimethyl-1,6-diazapiro[4.4]-nonane-2, 
7-dione, 
1,6-di(3-carboxyphenyl)-3,8-diphenyl-1,6-diazaspiro[4.4]nonane-2,7-dione, 
1,6-di[4-(4-carboxybenzyl)phenyl]-1,6-diazaspiro[4.4]nonane-2,7-dione, 
1,6-di(4-carboxyphenyl)-3,3,4,4,8,8,9,9-octamethyl-1,6-diazaspiro[4.4]nona 
ne-2,7-dione, 
1,6-di[4-(4'-carboxybiphenyl)]-3,3-dimethyl-1,6-diazaspiro[4.4]nonane-2,7- 
dione, 1,6-di(4-carboxymethylphenyl)-1,6-diazaspiro[4.4]nonane-2,7-dione, 
1,6-di[4-(4-carboxyphenyl)propyl]1,6-diazaspiro[4.4]nonane-2,7-dione, 
1,6-di[4-(4-carboxyphenylisopropyl)phenyl]- 
1,6-diazaspiro[4.4]-nonane-2,7-dione and the like. In the embodiment 
wherein Q is --C(O)OH, and the adjacent Z moieties on each ring form a 
cyclic structure fused to the spiro ring system, illustrative 
spirodilactams include 
1,6-di(4-carboxyphenyl)-3,4,8,9-dibenzo-1,6-diazaspiro[4.4]nonane-2,7-dion 
e, 
1,6-di(4-carboxymethylphenyl)-3,4,8,9-dibenzo-1,6-diazaspiro[4.4]nonane-2, 
7-dione, 
1,6-di[4-(4-carboxyphenyl)phenyl]-3,4,-8,9-dipyrido-1,6-diazaspiro[4.4]-no 
nane-2,7-dione and 
1,6-di[4-(4-carboxyphenyloxy)phenyl]-3,4,8,9-di(cyclopentano)-1,6-diazaspi 
ro[4.4]nonane-2,7-dione and the like. Also suitable are those 
spirodilactams wherein one spiro ring has a fused ring substituent and the 
other spiro ring is free of fused ring substituents, e.g., 
1,6-di(4-carboxyphenyl)-3,4-benzo-8-methyl-1,6-diazaspiro[4.4]nonane-2,7-d 
ione, 1,6-di 
[1-(4-carboxynaphthyl)]-3,4-cyclo-hexano-1,6-diazaspiro[4.4]-nonane-2,7-di 
one and the like. 
Of course, the corresponding compounds of formula I, wherein the --C(O)OH 
group in the above-named compounds is replaced by the corresponding 
anhydride, salt, ester or amide of the acid or by the acid chloride or 
bromide or Q is --CN, are also illustrative of the compounds of the 
invention. 
In general, compounds of the above formula I wherein R is aromatic and 
hydrocarbyl are preferred, especially such compounds wherein each n and r 
is O. The class of 1,6-di(carboxyphenyl) spirodilactam compounds is 
particularly preferred. Within the spirodilactam portion of the compounds 
of formula I spirodilactam rings which are substituted with hydrogen or 
methyl or fused with benzo rings are generally preferred, particularly the 
1,6-diazaspiro[4.4]nonane-2,7-dione compounds. 
The carboxyaryl-substituted spirodilactam derivatives of the above formula 
I are prepared by reaction of at least one "Q"-containing primary amino 
compound and a spirodilactam precursor. In terms of the spirodilactam of 
the above formula I, the "Q"-containing primary amino compound is 
represented by the formula II 
EQU Q-(R').sub.n R(X-R).sub.r NH.sub.2 (.HY).sub.m (II) 
wherein Q, R, R',X and r have the previously stated meanings; m is 0 or 1 
and 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, for example, hydrochloric and hydrobomic; sulfur 
acids, for example, surfuric or sulfonic; phosphorus acids, for example 
phosphoric or phosphonic; and carboxylic acids, for example, oxalic and 
the like. Preferably, Y is halogen, e.g., fluorine, chlorine, bromine or 
iodine and especially chlorine or bromine. Examples of compounds of 
formula II include 4-aminobenzonitrile, 4-aminobenzoic acid, 
4-aminobenzoic acid chloride, methyl 4-aminobenzoate, p-aminophenylacetic 
acid, p-aminophenylacetonitrile or salts thereof and the like. Such amines 
are known in the art as, for example, aminobenzoic acids as in U.S. Pat. 
No. 4,844,834, or are prepared by known techniques. 
The spirodilactam precursor is a 4-oxoheptanedioic acid compound or a 
1,6-dioxospiro[4.4]nonane-2,7-dione. In terms of the spirodilactam of the 
above formula I, the 4-oxoheptanedioic acid compound spirodilactam 
precursors are represented by the formula III 
##STR2## 
wherein Z has the previously stated meaning and A is hydroxy, lower alkoxy 
or halo, preferably middle halo. 
When the Z moieties are linked together to form a ring system the ring 
system is aromatic, cycloaliphatic or heterocyclic and is hydrocarbyl 
containing only atoms of carbon and hydrogen besides any heteratoms or 
substituted hydrocarbon containing additional atoms such as halogen, 
preferably middle halogen, in the form of inert carbon atom substituents. 
In one embodiment employing the ketodiacid compound spirodilactam 
precursor, each Z moiety is &gt;C(Z').sub.2 and the ketodiacid compound is an 
4-oxoheptanedioic acid compound. In one such embodiment, largely because 
of a particularly convenient method of producing the spirodilactam 
precursor, a preferred 4-oxoheptanedioic acid compound has at least one 
hydrogen on the carbon atom adjacent to each carboxy function, that is, at 
least one Z' on each carbon atom adjacent to a carboxy function is 
hydrogen. Such 4-oxoheptanedioic acid compounds are represented by the 
formula IIIa 
##STR3## 
wherein Z' and A have the previously stated meanings. Such 
4-oxoheptanedioic acid compounds include 4-oxoheptanedioic acid, dimethyl 
4-oxoheptanedioate, 2,6-dimethylheptanedioic acid, 
2,3,5,6-tetramethyl-4-oxoheptanedioyl chloride, di-n-propyl 
2,6-di-n-butyl-4-heptanedioate, 
7-carbomethoxy-3,3,5,5-tetramethyl-4-oxohexanoic acid and the like. The 
preferred ketodiacids of the above formula IIIa are those wherein each Z' 
is hydrogen or methyl, especially hydrogen, and each A is hydroxy or 
methoxy, especially hydroxy. 
These ketodiacid compounds are known compounds or are produced by known 
methods, but the esters of formula IIIa, i.e., the compounds wherein A is 
alkoxy, are produced by reaction of formaldehyde with an 
.alpha.,.beta.-ethylenically unsaturated carboxylic acid ester such as 
methyl acrylate, ethyl methacrylate, methyl crotonate, methyl ethacrylate, 
propyl 2,3-dimethylbutanoate and the like. This reaction is conducted in 
the presence of a catalyst system which comprises a thiazolium salt and a 
tertiary amine and produces the dialkyl 4-oxoheptanedioate derivative in 
good yield. This process is described in greater detail in U.S. Pat. No. 
4,800,231, incorporated herein by reference. Conversion of the esters 
thereby obtained to free acids or acid halides is by conventional methods 
as is the general interconversion of the acids, esters or acid halides of 
formula IIIa. 
In a second embodiment of the ketodiacid compound spirodilactam precursor, 
the 4-ketodiacid incorporates cyclic moieties between the keto group and 
the carboxy functions, i.e., two adjacent Z moieties form a fused cyclic 
ring structure Z". Such diacid compounds are represented by the formula 
IIIb 
##STR4## 
wherein A and Z" have the previously stated meanings. Illustrative of 
these 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-carbethoxy-2-morpholyl) ketone, di(3-carbomethoxy-2-napthyl) ketone 
and the like. The preferred cyclic ketodiacid compounds of formula IIIb 
are those wherein each Z" is a ring system of from 5 to 6 carbon atoms, 
inclusive, and up to one nitrogen atom, particularly benzo. 
Such ketodiacids are known compounds or are produced by known methods, such 
as the method of U.S. 1,999,181 or the method of Cava et al, J. Am. Chem. 
Soc., 77,6022 (1955). 
In yet another embodiment of the diketone compound spirodilactam precursor, 
the ketodiacid incorporates one fused cyclic moiety with the remainder of 
the Z moieties being &gt;C(Z').sub.2, i.e., the compounds are of the formula 
IIIc 
##STR5## 
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-(2-carbomethoxy-2-pyridyloyl)-2-ethylpropionic acid, ethyl 
3(2-carbethoxybenzoyl)propionate, 3-(2-carboxy-4-methylbenzoylbutyrl) 
chloride and the like. The ketodiacids of the above formula IIIc are known 
compounds or are produced by known methods. For example, 
2-carboxymethylbenzaldehyde 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 another embodiment of the invention, the spirodilactam precursor is a 
1,6-dioxaspiro[4.4]nonane-2,7-dione compound wherein the spiro ring system 
is substituted with hydrogen, alkyl or halogen, or which incorporates 
fused cyclic substituents which include the 3- and 4-spiro ring positions 
and/or the 8- and 9-spiro ring positions of the spiro ring system. 
The spirodilactone spirodilactam precursor, in terms of the spirodilactams 
of formula I, is represented by the formula IV 
##STR6## 
wherein Z has the previously stated meaning. 
In the embodiment of these spirodilactone spirodilactam precursors of the 
above formula IV wherein each Z is &gt;C(Z').sub.2, the spirodilactone is 
represented by the formula IVa 
##STR7## 
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, 
4,9-diphenyl-1,6-diazaspiro[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-dioxaspiro[4.4]nonane-2,7-dione, 
3,4,8,9-tetrafluoro-1,6-dioxaspiro[4.4]nonane-2,7-dione and the like. The 
preferred spirodilactones of the above formula IVa are those wherein at 
least one Z' of each Z'-substituted carbon atom is hydrogen. 
The compounds of formula IVa are known compounds or are produced by known 
methods such as the process of Pariza et al, Synthetic Communications, 
Vol. 13(3), pp. 243-254 (1983), herein incorporated by reference. 
In the embodiment of the spirodilactone spirodilactam precursors of the 
above formula IV which incorporates a fused cyclic moiety as a part of the 
two rings of the spiro ring system, the spirodilactones are represented by 
the formula IVb 
##STR8## 
wherein Z" has the previously stated meaning. Typical compounds of this 
formula IVb are 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, 
3,4,8,9-di-(pyrido)-1,6-dioxaspiro[4.4]nonane-2,7-dione and the like. 
These compounds are known compounds or are produced by known methods, for 
example, the process of the above Cava et al article or by the process of 
U.S. Pat. No. 1,999,181. 
In another embodiment of the spirodilactone spirodilactam precursor, a 
cyclic moiety is fused to one spiro ring and the other spiro ring is free 
from fused ring substituents. Such spirodilactones are represented by the 
formula IVc 
##STR9## 
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-morphoyl-1,6-diazaspiro[4.4]nonane-2,7-dione and 
the like. The spirodilactones of the above formula IVc are produced by 
known methods, for example, the dehydration of the corresponding 
ketodiacid. By way of 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 spirodilactone spirodilactam precursors are 
hydrocarbon except for the oxygen atoms of the lactone moieties, and 
particularly preferred are those spirodilactones which are free from fused 
ring substituents (formula IVa) or those which have a fused ring 
substituent on each of the spiro rings (formula IVb). An especially 
preferred spirodilactone spirodilactam precursor of the first class is 
1,6-dioxaspiro[4.4]nonane-2,7-dione. 
The acyclic 4-oxoheptanedioic acid compounds are known or are produced by 
the methods described above, but certain of the esters are also produced 
by the reaction of formaldehyde and unsaturated carboxylic acid esters by 
the process disclosed and claimed in U.S. Pat. No. 4,800,231. 
Interconversion of the acids, esters or acid halides of formula III is by 
conventional methods. The production of 4-oxoheptanedioic acid compounds 
of formula IV which contain cyclic moieties is by the process of Cava et 
al, J. Am. Chem. Soc., 77, 6022 (1955). The spirodilactones of formula IIb 
are produced by the process of Pariza et al, Synthetic Communications, 
Vol. 13(3), pp. 243-254 (1983), or if the spirodilactones have additional 
fused rings by known methods including the method described by Conover et 
al., U.S. Pat. No. 1,999,181, Cava et al., J. Am. Chem. Soc., 77, 6022 
(1955), or Gourmelon et al., Bull. Soc. Chem. 4032 (1971). Such methods 
include (1) in Conover et al., the decarboxylation of dicarboxylic acid 
anhydrides in the presence of known decarboxylation catalysts, (2) in Cava 
et al., the chromic acid oxidation of cyclic (aryl) substituted dicyclic 
(diarylene) compounds, and (3) in Gourmelon et al., Friedel Crafts 
condensation of cyclic (aryl) acid with cyclic (aryl) dicarboxylic 
anhydride. Other methods include Cava et al., J. Am. Chem. Soc., 79, 1706 
(1957) in which a fused ring-cyclobutene dibromide is treated with 
potassium hydroxide followed by oxidation with chromic acid in acetic 
acid, and Sikes et al., Meeting Am. Chem. Soc., April 1988, p. 614, in 
which an aryl magnesium bromide having an o-tolyl group is reacted with an 
excess of a dicarboxylic acid anhydride in benzene-ether solution followed 
by oxidation with chromium (VI) oxide in glacial acetic acid. Using these 
methods, spirodilactones in which adjacent Z groups form a Z" ring system 
inertly substituted at the 3-, 3,5-, 3,4,5-or 3,4,5- and 6-positions can 
be prepared. Inert ring substituents include halogen, haloalkyl, alkyl, 
alkoxy, alkythio, tertiary-amino, tertiary-aminoalkyl, in which each alkyl 
group has up to 10 carbon atoms, preferably 4 carbon atoms, or aryloxy or 
up to 10 carbon atoms and 1 to 2 rings. 
The "Q"-containing primary amino compound and the spirodilactam precursor 
react in a molar ratio of 2:1 although in practice reactant ratios from 
about 8:1 to about 1:1.5 are satisfactory. Reactant ratios of 
"Q"-containing primary amino compound to spirodilactam precursor which are 
substantially stoichiometric are preferred. Reaction is conducted in a 
liquid phase solution in an inert reaction diluent such as an 
N-alkylamide, e.g., N,N-dimethylformamide, N,N-dimethylacetamide, 
N-methyl-2-pyrrolidone and the like. Reaction takes place under reaction 
conditions at an elevated temperature, typically from about 80.degree. C. 
to about 250.degree. C., and at a reaction pressure sufficient to maintain 
the reaction mixture in a liquid phase, e.g., pressures up to about 20 
atmospheres. Subsequent to reaction the spirodilactam product is recovered 
from the reaction product mixture by conventional methods such as solvent 
removal, precipitation and chromatographic separation and the like. 
Recovery of the spirodilactam product is not required, however, and 
particularly in cases where substantially stoichiometric quantities of 
reactants were employed the spirodilactam may be reacted further in situ 
to form Q-substituted spirodilactams of the invention. 
The cyanoaryl- or cyanoalkylaryl-substituted spirodilactams in which Q in 
Formula I is cyano find utility as precursors of the corresponding 
carboxylic acid into which they are converted by conventional acid or base 
hydrolysis. 
The spirodilactams having the carboxyaryl or carboxyalkylaryl substituents, 
for example, in Formula I wherein Q is --C(O)OH, or C(O)OY' wherein Y' is 
H or hydrocarbyl, are useful in the formation of polyester or polyamide 
polymers or can be converted by conventional techniques into the 
corresponding anhydrides, acid chlorides or bromides or salts, which also 
find utility in the preparation of polyester or polyamide polymers. The 
spirodilactams of Formula I wherein Q is --C(O)OH can be converted to the 
ester compounds of the invention, for example, by reaction with an 
appropriate hydrocarbyl halide, in the presence of triethylamine, in a 
solvent, such as ethyl acetate. 
The spirodilactams having the carboxyaryl or carboxyalkylaryl 
substitutents, for example, in Formula II wherein Q is --C(O)N(Y").sub.2, 
are useful for the preparation of polyamides or can be converted by 
conventional techniques into the corresponding carboxylic acids. 
Conversely, these amides can be prepared by conventional ammonalysis from 
the acid or acid chloride. 
In preparing polyesters, for example, 
1,6-di(4-carboxyphenyl)-1,6-diazaspiro[4.4]nonane-2,7-dione or the salt, 
acid halide, ester or anhydride thereof is condensed with a dihydroxy 
compound using melt, solution or interfacial polycondensation techniques. 
The dihydroxy compound can be an alkylene, alicyclic or arylene dihydroxy 
compound, such as ethylene glycol, 1,4-butenediol, 
bis(4-hydroxyphenyl)methane or any of the dihydroxy compounds and methods 
disclosed in U.S. Pat. Nos. 4,866,155 and 3,824,211, the disclosures of 
which are incorporated herein by reference. 
In another embodiment of polyesters, 
1,6-di(4-carboxyphenyl)-1,6-diazaspiro[4.4]-nonane-2,7-dione is condensed 
with a diepoxide compound using conventional melt or solution 
polymerization techniques. The diepoxide compound can be an alkylene, 
alicyclic or arylene diepoxide compound, such as the diepoxides of any of 
the dihydroxy compounds disclosed in the above-mentioned U.S. Pat. Nos. 
4,868,155 and 3,824,211. When the diepoxide compound is aliphatic, the 
polymerization usually takes place at room temperature and when the 
diepoxide compound is aromatic, the polymerization may require heating the 
reaction mixture, usually in the presence of a catalyst, such as a 
conventional acid, base or salt catalyst, to a temperature sufficient to 
initiate the reaction. When the molar ratio of the diepoxide compound to 
spirodilactam bis acid compound is essentially 1:1, a linear polyester 
polymer is obtained. However, when the molar ratio of diepoxide compounds 
to spirodilactam bis acid is greater than 1:1, a crosslinked polyester 
polymer is obtained. 
In preparing polyamides, for example, 
1,6-di(4-carboxyphenyl)-1,6-diazaspiro[4.4]nonane-2,7-dione, the amide or 
the acid halide thereof is reacted under conventional polymerizing 
conditions known in the art with an amine compound having at least two 
amino hydrogen substitutents using conventional conditions for the 
formation of polyamides. In some cases, a polymerization catalyst is used 
in the formation of the polyamide. The amine compound can be an aliphatic 
or aromatic di-primary or di-secondary amine, such as hexamethylene 
diamine, methylene dianiline or any of the amines and methods, disclosed 
in U.S. Pat. Nos. 4,595,745, and 4,933,423 or a continuation-in-part 
thereof, U.S. Ser. No. 474,954 filed Feb. 5, 1990, the disclosure of each 
being incorporated herein by reference. 
The polyester products are useful for injection or compression moldings, 
extrusions, melt-spun or solvent-spun fibers and filaments, melt-extruded 
or solution-cast films, coatings and paints. 
The polyamide products are useful for films, fibers, yarns and the like. 
The polyester and polyamide products comprising (a) moieties derived from a 
spirodilactam compound, said compound having nitrogen atoms in the 1- and 
6-positions of the spiro ring system and having a carboxyaryl or 
carboxyalkylaryl substituent on each spiro ring nitrogen atom alternating 
with (b) moieties derived from a dihydroxy compound, a diepoxide compound 
or from a primary diamine compound. For example, a polyester of the 
invention includes polyesters of the formula Va or Vb 
##STR10## 
and polyamides of the formula VI 
##STR11## 
wherein ASDL is a moiety of an aryl-or alkylaryl-substituted 1,6-diaza 
[4.4] spirodilactam having aryl or alkylaryl substituents on each spiro 
nitrogen atom and R" is an unsubstituted or inertly substituted aliphatic 
or aromatic group of up to 18 carbon atoms. The group ASDL is represented 
by the removal of both Q moieties from the compounds of formula I. In the 
polyesters and polyamides R" is preferably an alkylene group of 2 to 10 
carbon atoms or an arylene group of 6 to 10 carbon atoms. 
The polyester and polyamides are polymers having a molecular weight of from 
about 1,000 to about 100,000, preferably from about 10,000 to about 
50,000. 
The invention is further illustrated by the following Illustrative 
Embodiments which should not be construed as limiting the invention.

ILLUSTRATIVE EMBODIMENT I 
A mixture of 6.60 g (0.04 mole) of ethyl p-aminobenzoate, 3.12 g (0.02 
mole) of 1,6-dioxaspiro[4.4]nonane-2,7-dione and 50 ml of 
N-methyl-2-pyrrolidinone (NMP) was placed in a 250 ml round-bottomed flask 
equipped with a mechanical stirrer and a condenser and warmed with 
stirring to 160.degree.-170.degree. C. After keeping the reaction at 
160.degree.-170.degree. C. for 12 hours, the mixture was cooled and NMP 
was removed under reduced pressure. The product was then precipitated in 
ether and dried in a vacuum oven. A C.sup.13 NMR analysis indicated the 
formation of the desired spirodilactam bis-ethyl benzoate diester product 
in 48% yield. 
ILLUSTRATIVE EMBODIMENT II 
A mixture of 13.5 g (0.03 mole) of spirodilactam bis-ethyl benzoate of 
Embodiment I above, 4.5 g (0.03 mole) of 1,4-butanediol, ten drops of 
tert-butyl titanate and 50 ml of diglyme (2-methoxyethyl ether) was heated 
at 150.degree.-160.degree. C. in a nitrogen atmosphere. Ethanol by-product 
was removed by distillation. After the reaction was complete, the reaction 
mixture was poured into methanol to isolate the desired polyester polymer. 
Confirmation of the repeating polyester unit was made by IR and C.sup.13 
NMR spectral analyses. 
ILLUSTRATIVE EMBODIMENT III 
A mixture of 9.0 g (0.02 mole) of spirodilactam bis-ethyl benzoate of 
Embodiment I above or its corresponding diacid, 1.32 g (0.02 mole) of 
hexamethylene diamine, 2 drops of triethylamine and 25 ml of diglyme was 
heated at 170.degree.-180.degree. C. in a nitrogen atmosphere. Ethanol 
by-product was removed by distillation. After the reaction was complete, 
the reaction mixture was poured into methanol to isolate the polyamide 
polymer. Confirmation of the repeating polyamide unit was made by IR and 
R.sup.13 NMR spectral analyses. 
ILLUSTRATIVE EMBODIMENT IV 
A mixture of 0.01 mole of spirodilactam bis-benzoic acid of Embodiment I 
above, 0.01 mole of the diglycidyl ether of 2,2-(4-hydroxyphenyl)propane, 
a catalytic amount of an imidazole and 10 ml of diglyme is heated at 
170.degree.-180.degree. C. in a nitrogen atmosphere. Ethanol by-product is 
removed by distillation. After the reaction is complete, the reaction 
mixture is poured into methanol to isolate the polyester polymer.