Process for preparing anti-static polyisocyanate-based polymers via incorporating a polyalkylene carbonate-salt mixture

This invention relates to a process for preparing polyisocyanate-based polymers which have the ability to dissipate static electrical charge. The polymers are rendered semi-conductive by having incorporated into them an anti-static additive which comprises an ionizable metal salt dispersed in a polyalkylene carbonate polyol.

BACKGROUND OF THE INVENTION 
This invention relates to a process for preparing polyisocyanate-based 
polymers, which have an improved ability to dissipate static electrical 
charge. 
The majority of organic polymers are poor conductors of electricity and 
therefore have a tendency to accumulate static electrical charge. As such 
they cannot be readily used in application areas which require 
semi-conductive properties unless further modified. 
Polyisocyanate-based polymers are useful in a wide variety of applications. 
Some of these applications are more sensitive than others to damage or 
discomfort caused by the accumulation of static electrical charges and 
their ultimate discharge. Areas where this may be critical include for 
example packaging of electronic components and medical applications where 
certain clean room operations require an essentially dust-free 
environment. Clothing and equipment prepared from or containing 
polyisocyanate-based polymers may be susceptible to the accumulation of 
static electricity and therefore will attract or be a means of 
transporting dust into the clean room or dust-free areas. 
It is known for example to incorporate conductive fillers such as fibers, 
powders and particles into a polymer to enhance its conductivity and thus 
reduce its potential to accumulate static electricity. However, loadings 
of such fillers are often in excess of 15 percent or more to obtain the 
good electrical semi-conductivity. Such high loadings are not beneficial 
to the polymer and its physical properties and may, for example, increase 
its brittleness. 
In U.S. Pat. Nos. 4,617,325 and 4,618,630 a means of obtaining polyurethane 
polymers which can dissipate electrical charge is taught by the use of 
anti-static additives consisting of ionizable salt in combination with 
"enhancers." The anti-static additive is prepared by dispersing an 
ionizable salt and enhancer into a polyether polyol. The enhancer compound 
is a certain carboxylic acid ester or salt of a fatty acid. However, in 
some instances, the enhancer compound acts as a plasticizer for the 
polyurethane polymer, altering its properties in an undesirable manner. 
For the preparation of certain polyisocyanate-based polymers, the use of 
polyalkylene carbonate polyols can be advantageous. Polyalkylene carbonate 
polyols are not readily miscible with the polyether polyols and the 
anti-static additive described in U.S. Pat. Nos. 4,617,325 and 4,618,630. 
Polyisocyanate-based polymers made with polyols may be modified to 
dissipate statical electrical charge by the incorporation of conductive 
fillers. 
It would therefore be desirable to provide a process whereby a 
polyisocyanate-based polymer formed by the reaction of an isocyanate with 
an active hydrogen-containing composition containing polyalkylene 
carbonate polyol and having excellent static electrical discharge 
properties and good physical properties are prepared. 
SUMMARY OF THE INVENTION 
It has now been discovered that such polyisocyanate-based polymers can be 
prepared with excellent static electrical discharge properties by a 
process employing a polyalkylene carbonate-salt mixture as an anti-static 
agent. 
In one aspect, this invention is a process for preparing a 
polyisocyanate-based polymer by the reaction of a polyisocyanate with an 
active hydrogen-containing composition characterized in that the said 
composition comprises a polyalkylene carbonate polyol having dispersed 
therein a non-volatile ionizable salt, and said reaction being conducted 
in the substantial absence of a carboxylic acid ester of C.sub.6-30 carbon 
atoms, a fatty acid salt and a phosphate ester compound. 
In a second aspect, this invention is a polyisocyanate-based polymer 
prepared by the reaction of a polyisocyanate with an active 
hydrogen-containing composition characterized in that the said composition 
comprises a polyalkylene carbonate polyol having dispersed therein a 
non-volatile ionizable salt, and said reaction being conducted in the 
substantial absence of a carboxylic acid ester of C.sub.6-30 carbon atoms, 
a fatty acid salt and a phosphate ester compound. 
In a third aspect, this invention is a poly(alkylene carbonate) polyol 
having dispersed therein a non-volatile ionizable salt characterized in 
that the salt is present in from about 0.01 to about 60 percent of total 
weight of polyol plus salt. 
DETAILED DESCRIPTION OF THE INVENTION 
As described in the summary of the invention, polyisocyanate-based polymers 
prepared by the reaction of an organic isocyanate with an active 
hydrogen-containing composition can be rendered conductive by 
incorporating into the active hydrogen-containing composition, or by 
forming an isocyanate prepolymer of an anti-static additive comprising a 
polyalkylene carbonate polyol containing dispersed therein a non-volatile 
ionizable salt. The polyalkylene carbonate polyol containing salt 
dispersed therein used as anti-static additive in the process of this 
invention comprises as one component, an ionizable salt. For the purpose 
of this invention, an ionizable salt is defined as a salt containing at 
least one metal cation which is in ionic association with at least one 
anion, and the ions in the presence of an electric field can be mobile. 
The cation can be any metal which forms an ionizable salt with one or more 
anions, including those metals in Row II, Groups I(a) and II(a); Row III, 
Groups I(a), II(a) and III(a); Row IV, Groups I(a) to IV(a) and I(b) to 
VIII(b); Rows V and VI, Groups I(a) to V(a) and I(b) to VIII(b); and the 
lanthanide series of the Periodic Table of the Elements. Preferably, the 
metal is an alkali metal, an alkaline earth metal, cobalt, nickel, iron, 
copper, cadmium, zinc, tin, aluminum or silver. More preferably, the metal 
is sodium or potassium. 
The anion is any which forms an ionizable salt with the metal cation. The 
anion is advantageously the conjugate base of an inorganic acid, a C.sub.2 
-C.sub.4 carboxylic acid or a tetraorganoboride ion. Suitable anions 
include, for example, the halides, i.e., fluoride, chloride, bromide and 
iodide; nitrate, thiocyanate, sulfate, hydrogen sulfate, sulfite, hydrogen 
sulfite, chlorate, carbonate, phosphate, hydrogen phosphate, dihydrogen 
phosphate, phosphite, hydrogen phosphite, dihydrogen phosphite, 
perfluoroalkylsulfonates where the alkyl is a methyl or a C.sub.6 -C.sub.9 
alkyl moiety, acetate, tetraorganoboride particularly tetraalkyl, and 
tetraphenylboride and the like. Of these, salts containing the anions 
tetraorganoborides, thiocyanates, trifluoromethylsulfonates and acetates 
are preferred on the basis of generally better performance and lower 
corrosion. Most preferred are the thiocyanate anion, 
trifluoromethylsulfonate and the tetraphenyl boride anion, which are less 
reactive with metals, water or other materials which are often present in 
the polymer or in the formation of the polymer. The most preferred salts 
are monovalent metal tetraphenylboride salts and sodium triflate 
(trifluoromethylsulfonate) salts. 
The most preferred monovalent metal tetraphenylboride salt used herein is 
any salt of a monovalent metal and the tetraphenylboride anion. Among the 
tetraphenylboride salts, the monovalent metal is preferably one in Group I 
of the Periodic Table of the Elements and is more preferably potassium or 
sodium. Most preferred are the alkali metal thiocyanate salts and 
tetraphenylboride salts comprising sodium and potassium. 
As stated before, a C.sub.6 -C.sub.30 carboxylic acid ester, a fatty acid 
salt and a phosphate ester are substantially absent from the reaction 
mixture. However, these materials may be used in very small amounts, i.e. 
1 or less part per 100 parts relatively high equivalent weight polyol, 
as for example surfactants. Most preferably, essentially none of these 
materials are present. 
A further component comprising the polyalkylene carbonate polyol containing 
therein dispersed salt is the polyalkylene carbonate polyol. The 
polyalkylene carbonate polyol, hereafter referred to as polyol, may 
have any functionality, molecular weight or carbon dioxide percentage. 
Full details relating to polyols are disclosed by publication U.S. No. 
4,686,276, which is herein incorporated by reference. Suitable polyols 
are those containing up to about 30 percent by weight carbon dioxide and 
preferably from about 5 to 25 percent by weight carbon dioxide. For 
reasons of solubility of the salt, it is preferred that the polyol 
contains polyoxyethylene linkages. 
The polyol containing the ionizable salt dispersed therein and which is 
used as an anti-static additive in the formation of the 
polyisocyanate-based polymer can be prepared by stirring the salt directly 
into the polyol. To facilitate the dispersion of the salt in the 
polyol, the mixing can be conducted at elevated temperatures. Temperatures 
sufficient to reduce polyol viscosities and provide a mobile mixture 
without being detrimental to the product and inducing for example thermal 
degradation, can be employed. Advantageously, the ionizable salt can be 
dispersed in the polyol in the presence of a liquid as described 
below. The liquid serves to reduce the viscosity of the polyol, thus 
assisting the mixing and dispersing of the salt into the polyol. 
The liquid is one in which (a) the polyol is miscible, (b) is 
non-detrimental to the polyol and salt or the process of dispersing the 
salt in the polyol and (c) can readily be removed after the salt has been 
dispersed in the polyol. Suitable liquids are the low boiling point 
organic compounds and include, for example, alcohols, ketones and 
halocarbons. Examples of suitable alcohols include methanol, ethanol, 
propan-1-ol, propan-2-ol, isomers of butanol and mixtures thereof. 
Examples of suitable ketones include acetone, methylethyl ketone, 
cyclopentanone, cyclohexanone and mixtures thereof. Examples of suitable 
halocarbons include dichloromethane, trichloromethane, tetrachloromethane, 
1,1-dichloroethane, 1,2-dichloroethane, trichloroethane and its various 
isomers, 1,1-dichloroethylene, 1,2-dichloroethylene, trichloroethylene 
ethylene and mixtures thereof. The preferred low boiling solvents include 
methanol, dichloromethane and acetone. 
The quantity of liquid employed is sufficient to reduce the viscosity of 
the polyol and allow efficient mixing with the salt. Advantageously, 
the quantity of liquid is more than about 25, preferably more than about 
40 and most preferred from about 50 to 90 weight percent of the total 
weight of polyol and liquid. 
Any quantity of a non-volatile ionizable salt can be dispersed in the 
polyol-liquid mixture. The upper limit is only restricted by the resulting 
viscosity of the polyol/salt dispersion after the removal of the 
liquid. The higher the salt quantity the greater viscosity of the 
resulting product. The salt content dispersed in the polyol is 
advantageously not greater than 60 weight percent based on the weight of 
the polyol, and preferably is from about 0.01 to about 50, and more 
preferably from about 1 to about 30, and most preferably from about 1 to 
about 20 weight percent. For convenience, the polyols having the 
ionizable salt dispersed therein at these concentrations will be referred 
to as the antistatic additive or "concentrate." 
In preparing polyisocyanate-based polymers, by the process of the 
invention, the "concentrate" ( polyol containing the salt dispersed 
therein) is formulated with other active hydrogen-containing compounds to 
give the active hydrogen-containing composition which is reacted with the 
polyisocyanate. Advantageously, the quantity of concentrate present in the 
polyisocyanate-based polymer is such that the polymer contains from 0.001 
to 10.0, preferably 0.001 to 5.0 and most preferably from 0.001 to 0.1 
percent by weight of the ionizable salt. This quantity of salt present in 
the polymer is sufficient to confer electrical semi-conductivity to the 
polymer and provide for the dissipation of static electrical charge. 
Accordingly, to achieve this concentration of ionizable salt in the 
polymer, sufficient quantity of concentrate needs to be formulated with 
the active hydrogen-containing composition to be reacted with the organic 
polyisocyanate. Alternatively, the required quantity of concentrate may be 
reacted with polyisocyanate to prepare a prepolymer which is then 
subsequently used in preparing the polyisocyanate-based polymer of the 
invention. It is preferred to blend the concentrate with the active 
hydrogen-containing composition because of the convenience of monitoring 
and controlling only one isocyanate-active hydrogen reaction. 
The quantity of concentrate that is blended with the active 
hydrogen-containing composition will depend on the weight of salt 
dispersed in the polyol. Advantageously, the quantity of concentrate 
present in the active hydrogen-containing composition is from about 0.01 
to about 25, preferably from about 0.01 to about 10 and most preferably 
from about 0.01 to about 5.0 weight percent based on total weight of the 
active hydrogen-containing composition including the concentrate. 
For the purposes of this invention, an active hydrogen-containing compound 
is one containing a hydrogen atom that, because of its position in the 
molecule, displays significant activity according to the Zerewitinoff test 
described by Kohler in the Journal of American Chemical Society, Vol. 49, 
p. 3181 (1927). Illustrative of such active hydrogen-containing groups are 
--COOH, --OH, --NH.sub.2, --NH--, --CONH.sub.2, --SH and --CONH--. Typical 
active hydrogen-containing compounds include polyols, polyamines, 
polyamides, polymercaptans and polyacids, collectively these may be 
referred to as polyahls. 
Polyahls suitable for use in the process according to this invention and 
the preparation of the active hydrogen-containing composition are those in 
which the concentrate is miscible. For the purpose of this invention, 
miscible is intended to mean components which can be mixed together to 
give a stable composition without, for example, phase separation. 
Exemplary of suitable polyahls include polyalkylene carbonate polyols, 
polyester polyols, polycaprolactones and polyamides. When the concentrate 
is formulated with a polyalkylene carbonate polyol, this polyol may be the 
same as that used in preparing the concentrate. 
The molecular weight and functionality of the suitable polyahl will depend 
on the properties desired in the polyisocyanate-based polymer. For 
example, the formation of flexible polyurethanes is favored by using 
polyahls having relatively high equivalent weights (i.e., 250 to 10,000) 
and relatively low (i.e., 2 to 4) functionalities. More rigid 
polyurethanes are generally prepared fom low equivalent weight (i.e., 50 
to 250 ) polyahls and those having a higher functionality (i.e., 3 to 16). 
Organic polyisocyanates which may be employed include aromatic, aliphatic, 
and cycloaliphatic polyisocyanates and combinations thereof. 
Representative of these types are diisocyanates such as metaphenyl 
diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, 
hexamethylene-1,6-diisocyanate, tetramethylene-1,4-diisocyanate, 
cyclohexane-1,4-diisocyanate, hexahydrotoluene diisocyanate and isomers, 
naphthalene-1,5-diisocyanate, 1-methoxyphenyl-2,4-diisocyanate, 
diphenylmethane-4,4'-diisocyanate, 4,4'-biphenylene diisocyanate; 
3,3'-dimethoxy-4,4'-biphenyl diisocyanate, 3,3'-dimethyl-4,4'-diphenyl 
diisocyanate and 3,3'-dimethyldiphenylpropane-4,4',4'-diisocyanate; 
triisocyanate such as toluene-2,4,6-triisocyanate and 
dimethyldiphenyl/methane-2,2',5',5'-tetraisocyanate and the diverse 
polymethylene polyphenyl polyisocyanates. A crude polyisocyanate may also 
be used in making the polyisocyanate-based polymers, such as the crude 
toluene diisocyanate obtained by the phosgenation of a mixture of toluene 
diamines or the crude diphenylmethane diisocyanate obtained by the 
phosgenation of crude diphenylmethane diamine. Polyisocyanate prepolymers 
prepared from any of the above polyisocyanates may also be employed. 
The preferred polyisocyanates for use in the practice of the present 
invention include toluene diisocyanate, methane diphenylisocyanate, 
polymethylene polyphenylisocyanate and mixtures thereof. When a mixture of 
polyisocyanates is employed, the mixture will comprise essentially one 
polyisocyanate in at least 50, preferably at least 60 and most preferred 
at least 70 percent by weight of the total polyisocyanate mixture. 
The isocyanate index (ratio of equivalents of isocyanates to equivalents of 
active hydrogen-containing groups) is advantageously from about 0.8 to 
5.0, preferably from about 0.8 to 3.0, and most preferably from about 0.8 
to about 1.3. 
Prepolymers or quasi prepolymers of the foregoing polyisocyanates are also 
useful herein. 
The reaction of polyisocyanate and active hydrogen-containing composition 
to give a polyisocyanate-based polymer may be conducted in the presence of 
various other additional components. Additional components commonly used 
in the preparation of polymers include catalysts, surfactants, blowing 
agents as required, pigments, fillers, flame retardants, stabilizers and 
the like. 
Any suitable urethane catalyst may be used including tertiary amines such 
as, for example, triethylene diamine, N-methylmorpholine, 
N-ethylmorpholine, diethylethanolamine, N-cocomorpholine, 
1-ethyl-4-dimethylaminoethyl piperazine, 3-methoxy-N-dimethylpropylamine, 
N,N-dimethyl-N',N'-methylisopropylpropylene diamine, 
N,N-diethyl-3-diethylaminopropylamine, dimethylbenzylamine and the like. 
Other suitable catalysts are, for example, tin compounds such as stannous 
chloride, tin salts of carboxylic acids such as dibutyltin 
di-2-ethylhexoate, as well as other organometallic compounds such as are 
disclosed in U.S. Pat. No. 2,846,408. Catalysts for the trimerization of 
polyisocyanates, such as alkali metal alkoxides, may also optionally by 
employed herein. 
If the polyisocyanate-based polymer to be prepared is required to be a 
foam, a blowing agent is employed. Such a blowing agent comprises an inert 
gas, a low boiling organic liquid such as methylene chloride or 
trichlorofluoromethane, and/or a chemical blowing agent such as water, 
peroxide or azo compounds which react during the urethane polymerization 
reaction to generate a gas. Suitable blowing agents are described in U.S. 
Pat. Nos. 4,125,487 and 3,753,933 incorporated herein by reference. 
Sufficient quantity of blowing agent is used to provide a cellular 
polymer, foam, with the desired density. Larger quantities of blowing 
agents provide for lower density foams. Preferably, a blowing agent is not 
present in the reaction mixture. 
A surfactant may be used in the reaction mixture to stabilize the 
polymer-forming reaction mixture until it is sufficiently cured to 
maintain its cellular structure, if so desired. Numerous surfactants have 
been found satisfactory. Nonionic surfactants are preferred. Of these, the 
nonionic surface active agents prepared by the sequential addition of 
propylene oxide and then ethylene oxide to propylene glycol and the solid 
or liquid organosilicones have been found particularly desirable. In 
addition, components such as fillers, fibers, internal mold release 
additives, cell openers, preservatives, pigments and other colorants, 
anti-oxidants and the like may be employed as is well-known in the art. 
The polyisocyanate-based polymers prepared here may be made in either a 
one-step or two-step process. In the one-step process, the polyisocyanate 
and active hydrogen-containing composition and any optional components are 
brought together in one step and mixed to give the polymer-forming 
reaction mixture. The reaction mixture may be poured, sprayed or injected 
into or onto suitable containers, molds or designated application areas. 
U.S. Pat. Nos. 4,218,543 and 4,552,945 illustrate the process of making a 
polymer by a one-step method and are incorporated herein by reference. 
In the two-step process, all or a major portion of the active 
hydrogen-containing composition is reacted with the polyisocyanate in a 
preliminary step to form a prepolymer or quasi prepolymer. This prepolymer 
or quasi prepolymer is then reacted in a second step with the remaining 
portion of polyisocyanates and optional other additives to give the 
polyisocyanate-based polymer reaction mixture which can then be directed 
to the appropriate application. 
Suitable process for preparing polyisocyanate-based polymers are disclosed 
in U.S. Pat. Nos. 2,764,565; 3,755,212; 3,821,130; and U.S. RE 24,514 
incorporated herein by reference. 
The resulting polyisocyanate-based polymer which is obtained by the process 
of this invention is substantially more conductive than a like polymer 
which is prepared in the absence of the ionizable salt. 
The polyisocyanate-based polymer prepared by the process of this invention 
displays good dissipative potential of static electrical charge and finds 
value in a wide number of applications. The polymers can, for example, be 
advantageously used in packaging of electronic components, packaging of 
agricultural and industrial products which are granular or powders, 
manufacturing of anti-static footwear and clothing, and the making of 
plastic feed bottles and transfer lines used in hospitals and 
laboratories, and preparing anti-static surfaces of, for example, walls, 
floors, desktops, working areas and shipping containers. The polymers may 
also be used as an adhesive where insulator properties in laminate 
structures are not desirable.

ILLUSTRATIVE EMBODIMENTS 
The following examples are provided to illustrate the invention and not to 
limit the scope thereof. All parts and percentages are given by weight, 
unless otherwise indicated. 
EXAMPLE 1 
A polyalkylene carbonate-salt complex is prepared by dissolving 900 parts 
of a polyethylene carbonate triol (equivalent weight 343, 20.9 weight 
percent CO.sub.2 content) in 6000 parts methanol and then adding 100 parts 
of sodium tetraphenylboride. The mixture is stirred about 15 minutes and 
then the methanol removed by distillation at reduced pressure and at a 
temperature of 50.degree. C. to 80.degree. C. Final traces of methanol and 
any residual water are removed from the polyethylene carbonate-salt 
complex by passing a steady stream of nitrogen through the solution at 
110.degree. C. for about 1 hour. This results in a polyalkylene 
carbonate-sodium tetraphenylboride mixture containing about 10 percent by 
weight of salt. This mixture, concentrate, is used as anti-static additive 
in the preparation of polyisocyanate-based polymers. 
Polyisocyanate-based coating polymers are prepared according to the 
formulation given below employing different quantities of the prepared 
anti-static additive. 
The polymer is prepared by mixing all components, except the isocyanate, on 
a roller until homogenous. The isocyanate is then added to the homogenous 
mixture which is then shaken vigorously for about 30 seconds. This 
resulting mixture is then further mixed on a roller until it passes from 
being opaque to a clear (about 5 minutes) liquid. The clear liquid is then 
applied to a 3".times.5" piece of cardboard using a #56 wire-wound roller 
or a 15-20 mil doctor blade. The coating is then allowed to cure overnight 
at room temperature prior to observing its physical properties. 
TABLE I 
______________________________________ 
Com- 
parative 
Poly- Poly- Poly- Poly- Poly- 
mer 1 mer 2 mer 3 mer 4 mer A* 
______________________________________ 
polyol.sup. .circle.1 
64.5 64.5 64.5 64.5 64.5 
Dowanol .RTM. 
2.86 2.86 2.86 2.86 2.86 
PMA.sup. .circle.2 
Surfactant.sup. .circle.3 
1.73 1.73 1.73 1.73 1.73 
Dibutyltin 
0.065 0.065 0.065 0.065 0.065 
dilaurate 
Concentrate 
0.2 0.5 1.0 5.0 0 
Percent 0.015 0.037 0.073 0.37 0 
ionizable 
salt in 
polymer 
Isocyanate 
67.1 67.1 67.1 67.1 67.1 
Index.sup. .circle.4 
Surface 13.34 13.14 12.43 12.32 13.88 
Resistivity 
log.sub.10 
(ohms/sq) 
Hardness 8H 8H 8H 8H 2H 
______________________________________ 
*Not an example of this invention 
.sup. .circle.1 Polyoxyethylene carbonate triol, (equivalent weight 343, 
CO.sub.2 weight percent 20.9) 
.sup. .circle.2 Propylene glycol methyl ether acetate sold by The Dow 
Chemical Company 
.sup. .circle.3 Silicone surfactant L5310 sold by Union Carbide, used as 
2 percent weight solution in Dowanol .RTM. PM acetate 
.sup. .circle.4 Desmodur N75, 75% solution produced by Bayer 
Surface resistivity is measured according to procedure ASTM D-257 using a 
Doctor Theidig MILLI TO-2 ohmmeter with guard ring electrode assembly. 
Lower values indicate better conductivity. Hardness (shore) is measured 
according to procedure ASTM D-2632. 
As can be seen from the experimental data, the incorporation of very small 
amounts of the ionizable salt provide dramatic decreases in the surface 
resistivity and therefore enhance conductivity of the polymer. As can be 
seen from the experimental data associated with Polymer 4, it can be noted 
that substantially increasing the amount of concentrate does not greatly 
improve the electrical properties over and above the small quantities. 
EXAMPLE 2 
A polyisocyanate-based adhesive is prepared according to the formulation 
given below: 
______________________________________ 
polyol 12.18 parts 
Antistatic (as in Example 1) 
Additive 
1,4-butanediol 1.10 
glass 150-200 0.02 parts 
micron beads 
(Rubicon) LF-168 
9.53 
MDI* 
______________________________________ 
*Polymeric MDI sold by Rubicon 
The adhesive is smeared onto a 1.times.4.times.0.064 inch cold rolled steel 
plate. A second similar metal plate is pressed over the smeared adhesive 
to give a 0.5" overlap and the so formed laminate clamped together. The 
laminate is cured for about 1 hour at about 125.degree. C. and a further 
24 hours at ambient temperature. 
The laminate has a joint lap shear of 4000 psi (ASTM Method D-1002). 
When the cured adhesive was poured into a 1/8 inch thick mold and cured as 
above, an elastomeric casting is produced that has a surface resistivity 
(log.sub.10) of 11.00 ohm/square. 
COMATIVE EXAMPLE B 
A polymer adhesive is prepared as for Example 2, only in this case the 
antistatic additive contains no sodium tetraphenylboride. 
A laminate as in Example 2 is prepared with which exhibits a lap shear 
strength of 4097 psi. A casting similarly prepared exhibits a surface 
resistivity (log.sub.10) of 13.2 ohm/square. 
This illustrates the improved antistatic properties to be gained by 
preparing polymer by the process of this invention. Lap shear strength is 
approximately the same indicating little or no detrimental effect through 
incorporating the ionizable salt. 
EXAMPLE 3 
Following the procedure of Example 1, a polyalkylene carbonate 
polyol-sodium tetraphenylboride complex is prepared by adding to 900 parts 
of a polyoxyethylene carbonate diol (equivalent weight 1800, 20.4 weight 
percent CO.sub.2) dissolved in 6000 parts acetone, 100 parts of sodium 
tetraphenylboride. The resulting solvent-free concentrate contains about 
10 percent by weight salt. 
A flexible polyisocyanate-based foam is prepared according to the following 
formulation reacted with toluenediisocyanate (Index 1.05). 
______________________________________ 
99.1 polyoxyethylene carbonate 
parts triol 
(eq wt 1053, 10.sub.2 15%) 
0.9 concentrate 
parts 
3.5 water 
parts 
0.75 L-532 silicone-surfactant 
sold by Union Carbide 
0.05 Dabco 33LV hexamethyl- 
enediamine catalyst sold 
by Air Products 
0.12 Stannous octoate 
______________________________________ 
The resulting foam has a surface resistivity (log.sub.10) of 12.50 
ohm/square. 
COMATIVE EXAMPLE C 
A similar flexible polyisocyanate-based foam as in Example 3 is prepared 
only in this case the 0.9 part concentrate is only the polyoxyalkylene 
carbonate polyol, no sodium tetraphenylboride is present. 
The resulting foam has a surface resistivity (log.sub.10) of 12.90 
ohm/square, thus illustrating that semi-conductive properties of a 
flexible polyurethane foam can be improved by at least a factor of 2.5 
when prepared by the process of this invention.