Note: Descriptions are shown in the official language in which they were submitted.
~ 13,0?3
This ~nvention is directed to a curable com-
position of a cycloallphatic epoxide and a compatible
amount of a polyol.
~ Cycloaliphatic epoxide resins have inheren~ly
good electrical properties. Unmodified cycloaliphatic
epoxide resins when cured, however, produce inherently
brittle material~. Thus, modifications must be made in
~he cycloaliphatic epoxide resin systems ~o decrease
their brittleness as well as provide tough ~ystems in
order to provide the necessary thermal shock resis~ance
(TSR). Also, resin systems with good electrical pro-
perties at elevated temperatures ~re required in many
applications.
The problem, thens becomes one of developing
cycloaliphatic epoxide sys~ems with adequate thermal
shock resistance while retaining their excellent electrical
properties and high heat distortion temperature.
Modification of the cycloaliphatic epoxides with
low (~20Q0) molecular weight flexibilizers showed an
averaging effect betweerl the so~tening polnt o~ the un-
modified resin and that of the flexibilizer. The result
was a moderate improvement in the TSR accompanied by
a ra~her large redution in the heat distortion tempera-
ture.
Thus, a need exists to develop a cycloaliphatic
epoxide system with a high TSR, a high heat distor~ion
temperature which retains the excellent electrical
properties of the systems.
~,
2.
13,023
~ ~ ~ 3
THE INVENTION
_ . . .
The curable cycloaliphatic containing com
positions of this lnven~ion which when cas~ into
articles are characterized by an excellent b~lance of
physical properties, high TSR, high heat distortio~
temperature and good electrical proper~ies.
The compositions of this invention are useful
in making elec~rical components such as, for example,
outdoor insulation pplications and coil and trans-
former encap~ulation.
The curable cycloaliphatic composition of this
invention comprise a cycloalipha~ic epoxide and a
polyol having a molecular weigh~ of from about 1000
to that mQlecular weight which does not form a two
phase system wi~h the epoxide.
Suit:able cycloaliphatic epoxides for purposes
of ~his invention are those having an average of more
than one vicinal epoxy group per molecule. The epoxy
groups can be terminal epoxy groups or internal epoxy
groups as exemplified by the cycloaliphatic epoxides
which are subsequently described. Particularly desir-
able cyc~oaliphatic epoxides are the cyclohexane
diepoxides, that ls epoxides having at least one
cyclohexane ring to which is attached at least one .
vicinal epoxy group.
Illustrative of suitable cycloaliphatic
epoxides are the following:
~ ~ 3~ 3,~23
FORMULA I
Diepoxides of cyclo~lipha~ic es~ers of
dicarboxylic ac~ds h~ing the formul~:
0~~~ 0
R8 R7 R7, R8
wherein Rl through Rg, which can be ~he sa~e or
different are hydrogen or alkyl radicals generally
containing one to nine carbon atoms inclusive and
preferably containing one to three carbon atoms
inclusive as for example methyl, ethyl, n-pr~pyl,
n-butyl, n-hexyl, 2-ethylhexyl, n-octyl, n-nonyl and
~he like; R is a valence bond or a divalent hydro-
carbon radical generally containing one ~o nine ~arbon
atoms inclusive and preferably containing four to six
carbon atoms inclusive, as for e~ample, alkylene
radicals, such as trimethylene, tetramethylene,
pentamethylene, hexamethylene, 2-ethylhexamethylene,
octamethylene, nonamethylene, and the like; cyclo-
aliphatic radical~, 6uch as 1,4-cyclohexane, 1,3-
cyclohexane, 1,2-cyclohexane, and the like.
Par~icularly desirable epoxides, falling
within the scope of Formula I, are those wherein R
4.
~ ~364~ 13,023
through Rg are hydrogen and R is alkylene containing
four to 6iX car~on atoms.
Among speclfic diepoxide~ of cycloaliphatic
esters of dicarboxylie acids ar the following:
bis(3,4-epoxycyclohexylmethyl)oxalate,
bis(3,4-epoxycyclohexylmethyl)adipate,
bis~3,4-epoxy-6-methylcyclohexylmethyl)adipate,
bis(3,4-epoxycyclohexylmethyl)pi~elate,
~nd the like. Other suitable compounds are
described in U.S. Pat. No. 2,750,395 to
B. Phillips et al.
FORMULA II
A 3,4-epoxycyclohexylmethyl 3,4-epoxyeyclo-
hexane carboxylate havlng the formula:
wherein Rl through R9 which can be the same or
different are as defined for Rl in formula I.
Particularly desirable compounds are those wherein
Rl ~hrough R9 are hydrogen.
Among specific compounds falling within the
3~;42 D-13, 023-C
. scope of Fc~rmuls II are the following: 3,4-epoxy-
cyc`loh~ylme~hy~, 3, 4-ep~ys~yclollexanecarboxylate,
3, 4-epoxy-l-methyl cyr~ ohe~ylmethyl, 3, 1~-epoxy-l-
methyleyclohexylmethyl, 3, 4-epoxv-1-methylcvclo-
hexanecarboxylate, 6-methyl-3,4-epoxycyclohexyl-
methyl, 6-methyl-3,4-epoxycyclohexanecarboxylate,
3,4-epoxy-3-methylcyclohexylmethyl, 3,4-epoxy-3-
methylcyclohexanecarboxylate, 3,4-epoxy-5-methyl-
cyclohexylmethyl, 3,4-epoxy-5 methylcyclohexanecar-
boxylate. Other suitable compounds are described in
U.S. Pat. No. 2,890,194 to B. Phillips et al.
FO~M~LA III
Diepoxides having the formula:
Rl' ~ 3'R /
~ 1~ 0 CH2 R I ~
Rg~ ~ \ R5, 8R / ~ ~R4"
8'R7,R6' 71'R / R5"
wherein the R ~ingle end double p~imes, which can be
t~e ~ame or different, are monov21ent substituents
~uch as hydrogen, halogen, i.e. chlorine, bromine,
iodine or flusri~e~ or monovalent hydrocarbon radicals,
or radicals as further defined in U.S. Pat No.
3,3189822 to Rans Batzer et al. issued May 9, 1967.
13,023
~ 3~ ~ ~
Particularly desirable compound~ ~re those wherein
all the R' 5 are hydrogen.
Other suitable cycloaliphatic epoxides are
the following:
~ ~
~f~
and the like.
The preferred cycloaliphatic epoxides are
the following:
3,4 Epoxycyclohexylmethyl-3,4-Epoxy-
cyclohexane caboxylate
~0 ~ C -~ ~o
Bi~(3,4-Epoxycyclohexylmethyl)Adipate
a
~~ -C4H8-C-~
2-(3,4-Epoxycyclohexyl-5,5-spiro-3,4-
epoxy)cyclohexane-meta-dioxane
~o~{~
~ ~ ~ 3~ 39~23
Vinyl cyolohexene Dioxide
CH2-CH2
or mixtures thereof .
Epoxides with six menibered ~ing structures may
also be used, such as diglycidyl esters of ph~halic acid,
partially hydrogenated ph~halic ~cid or fully hydrogena~ed
phtha:Lic acid. Diglycidyl esters of hexahydrophthalic
aeids being preferredO
The glyeol suitable for use in thi inven-
tlon has a molecular weight of from about 1000 to that
molecular weigh~ which does not form a two phase
system with the epoxide, which is about 4000.
The glycols include polycaprolac~one polyols
as well as alk:ylene oxide adducts of polyhydroxyalkanes.
Illustrative of the polycaprolactone polyols
that can be u~ed one can mention the reaction pro-
ducts of a polyhydroxyl compound having from 2 to 6
hydroxyl groups with caprolactone. The manner in
whieh these polycaprolactone polyol compositions are
produced is shown in U.S. 3,169,945 and many such
compositions are commercially available. In the
following table there are listed illustrative poly-
caprolactone polyol~. The first column lists the
organic functional initiator that is reacted wlth
the caprolactone and the average molecular weight of
the polycaprolactone polyol is shown in the second
column.
8.
3~,9L;~ 139 0~3
Knowing the molecular weights of 'che
initiator and of the polycaprolactone polyol one
can readily dPtermine the average number of molecules
of caprolactone (CPL Units) that reacted to produce
- the compound; thi~ figure ls ~hown in the third
co lumn .
9.
13,023
Average No.
~er ge MW of CPL Units
Initineor . ~ in moleeules
1 Ethylene glycol 290 2
2 Ethylene glycol ~ ~ 803 6~5
3 Ethylene glycol 2,114 18
4 Propylene glycol 874 7
5 Octylene glycol 602 4
6 Deca~ence glycol 801 5,5
7 Diethylene glycol 527 3.7
8 Dieth~lene ~lycol ~47 6.5
9 Dlethylene ~lycol 1,246 10
Diethylene glycol 1,998 16,6
11 Diethylene glycol 3j526 30
12 Triethylene glycol 754 5.3
13 Polyethylene glycol (MW 20n~* 713 4.5
14 Polyethylene glycol ~M~ 600)* 1,396
Polyethylene glycol (MW 1500)* 2,868 12
16 1,2-Propylene glycol 646 5
17 1~3-Propylene glycol 988
18 Dipropylene glycol 476 3
19 ~Polypropylene glycol ~MW 425~*824 3~6
20 Polypropylene glycol (MW 1000)*1,684 6
21 Polypropylene glycol (MW 200Q)*29456 4
22 Hexylene ~lycol 916 7
23 2 Ethyl-1,3-hexanediol 602 4
24 l,S-Pentanediol 446 3
25 1,4-Cyclohexanediol 629 4.5
26 1,3-Bis(hydroxyethyl)-benzene 736 5
27 Glycer~l 548 4
28 1,2,6-Hex~metriol 476 3
29 Tr~methylolpropane 590 4
30 Trimethylolpropane 761 5,4
31 Trimethylolpropane 1,103 8, 5
32 Triethanolamine 890 6. S
33 Erythritol 920 7
34 Pentaerythr~tol 1,219 9.5
Avera~e molecular weight~of glycol~
The structures of the compounds in the above
~abul~tion are obvious to one skilled in the art
ba~ed on the informa~ion given. The structure of
compound ~o. 7 is:
10.
13, 023
O O
.~ ..
HC) [ ~CH2) sC~ rCH2CH20~H2CH2 [ OC (CH2~ 5 ] rOH
wherein the variable r is an ~nteger, the su~ of r +
r has an avera~e value of 3 7 and ~he average
molecular weight is 527. The ~tructure of compound
No. 20 is:
O O ''
H0[(CH2~C0]~(C3H6~n C3H61o~H2)s]roH
wherein the sum of r ~ r has an average value of 6
and the average molecular weight i~ 1,684. This
explanation makes explicit ~he s~ructural formulas of
compounds 1 l:o 34 set forth above.
Il:Lustrative alkylene oxide adducts of
polyhydroxya:Lkanes incll~de, among others, the alkylene
oxide adducts o ethylene glycol, propylene glycol,
1,3-dihydroxypropane, 1,3-dihydroxybutane, 1,4-dihydroxy-
butane~ 1,4-1,5~ and 1,6~dihydroxyhexane, 1,2-, 1,3-,
1,4-, 1,6-, and 1,8-dihydroxyoctane, l,10-dihyd-roxy-
decane~ glycerol, 1,2,4-trihydroxybutane, 1,2,6-
trihydroxyhexane, l,l,l-trimethylolethane, 1,1,1-
trimethylolpropane, pentaçrylthritol~ caprolackone~
polycaprolactone, xylitol, arabitol, sorbitol, mannitol,
and the like; preferably the adducts of ethylene oxide,
propylene oxide, epoxybutane, or mixtures thereof. A
preerred cl~ss of alkylene oxide adducts of poly-
hydroxyalkanes are the ethylene oxide, propylene oxide,
butylene oxide, or mixtures thereof, adduets of
trihydroxyalkanes.
11.
13,0?3
3~2
The preferred alkylene oxide adducts of
polyhydroxyalkan~s are c~f 'che following formula:
~10~O~CH2o~H-o~nH] 3
H3
wherein ~10 is ~ll~ne of 3 to 10 carbon ~toms, prefer
ably 3 carbon atoms, and n is an lnteger of from
~bout 4 to abs)u~ 25.
The polyols constitu'ce from about 10 to
about 2S weight percent, preferably from about 10
~to ~bout 20 weight percent.
It is customary ~ dd appropriate hardeners
to epoxide compositions to effect cure.
Among suitable hardeners ~re khe ollowing:
1. phenolic hardeners ha~ing at least 2
phenolic hydroxyl groups and preferably having at
least 3 phenolic hydroxyl groups per molecule.
2. polybasic acids having at least 2
carboxylic acid groups per molecule.
3. anhydrides o~ acids having at least 2
carboxylic acid groups per molecul~.
Exemplary of suitable phenolic hardeners are
the following polyhydric phenols: catechol, hydro-
quinone, llydroxyhydroquinone, phloroglucinol,
resorcinol and pyrogallol; the di and polynuclear
phenols such as the bisphenol is described in Bender
et al., U.S. Pat. No. 2,506,~86 and polyphenylols
12.
13,023
~ ~ 3~ ~ ~
such as novolac condensates of a phenol and a
satura~ced or unsatura~ced aldehyde containing an average
of from three to 20 or more phenylol groups per
molecule ~cf. book by T. S. Carswell entitled
"Phenoplasts, tl published in 1947 by Interscience
Publishers of New York).
Examples of suitable polyphenylols derived
from a phenol and an unsaturated aldehyde such as
' acroleln are the triphenylols, pentaphenylols ~nd
heptaphenylols described in U.S. Pat. No. 2,885,385
to A.G. Farnham, issued May 5, 1959.
The phenols may eontain alkyl or ryl ring
substituents or halogens, as exemplified by the alkyl
resorcinols, the tribromo reso~cinol and the dlphenols
containing alkyl and halogen substituent~ on the
aromatic ring (Bender et al., U.S. Pat. No. 2,506,486).
The polyhydric phenols can consist of two or
more phenols connected by such groups as methylene,
alkylene, ether, ketone, or sulfone. The connecting
groups are further exemplified by the following com~
pounds: bis(p-hydroxyphenyl)ether; bis(p-hydrox-
yphenyl)ketone, bis(p-hydroxyphenyl)methane, bis(p-
hydroxyphenyl)dimethyl methane, bis(p-hydroxyphen-
yl)sulfone and the like.
For purposes of stoichiometric calculations
with rPspect to phenolic hardeners, one phenolic
hydroxyl group is deemed to react with one epoxy group.
13.
13,023
~ ~3~ ~ ~
Illustrat~ve of ~uitable polybasic acids
are the p~lycarboxylic acids of the formula:
HOOC-(CH2)f-COOH
wherein is an integer generally having a value of
rom 1 to 20 inclusive, as for example, malonic,
glu~aric, adipie, p~melic, suberic, azelaic, sebacic
and the like. Other examples of ~uitable aci~s are
phthalic acid, isophtha~ic acid, terephthalic acid
and the like. Further acids are enumerated in U.S.
Pat. No. 2,91~,444 to ~. Phillips et al., issued
Dec. 22, 1959.
Among ~ther suitable polybasic acids, having
at least two carboxylic group~ per molecule, can be
noted the following: tricarballylic acid, trimellitic
acid and the l~ke. Other ~uch sui~able polybasic
acids, ineluding polyesters thereof, are described in
U.5. Pat. No. 2,921,925 to B. Phillips et al.
Suitable anhydrides ~re the anhydride~ of the
acids listed above.
2~ For purposes of stoichiometric calculations
wit~ re~pect to acids, one carboxyl group is deemed
to react with one epoxy group; with respect to
anhydrides, one anhydride group is deemed to react
with one epoxy group.
Preferred hardeners include methyltetra-
hydrophthalie anhydride, hexahydrophthalic anhydride
and methylhexahydrophthalic anhydride.
14.
3~ ~ ~
13~023
In an embodiment of this invention, the
hardener such as the anhydride may be reacted with
the glycol and this reacted product added to the
epoxide.
It is to be understood that other addi-
tives can be added to the compositions of this
invention as is well known in the epoxy art. These
addi-tives include the following: catalysts or
accelerators, such as amines including (2~hydroxy
ethyl)trimethyl ammonium hydroxide t45 percent con-
centration in methanol, known as choline base,
benzyl dimethyl amine, 2-methyl imidazole, metallic
compounds, such as stannous octanoate, peroxides
or ethylene glycol; modifiers such as dimer acid
(made from unsaturated C18 fatty acids and is a
mixture of 3 percent mono basic acids, 75 percent
dimer acid and 22 percent trimer acid and sold under
the name of Empol* 1022 by Emery Industries), a
carboxyl terminated butadiene acrylonitrile (80~20)
random copolymer having a molecular weight of about
3300; fillers such as clay, silica or aluminum tri-
hydride which may be coated with, for example,
silanes, which fillers may be added in amounts of up
to about 60 percent; pigments such as carbcn black;
mold release agents, and the like.
The compositions of this invention are
prepared by simply mixing the epoxide, glycol,
hardener and other ingredients at room or higher
.
*Trademark. 15.
i~
13, 023
3~
temperatures in a suitable eontainer. Also, the
epoxide and glycol may be mixed ln one container
and the hardener, catalyst and/or accelerator in
another container and these two mixed. The composi~
tion is then heated in order to effect it~ cure.
The temperature to which the composition of this
inven~cion are heated to effect cure will, of course,
vary snd depend, in part upon the exac~ formulations
of the composition. Generally, temperatures in the
range of about 100C to about 200C are used for a
period of time ranging fxom about 1 '~o about ~ hours.
~ 7
/
16 .
13,023
~ ~ 36
EXAMPLES
The following Examples serve to give ~pecific
illustrstion of the practice of thls inYentisn but they
are not ~ntended in any way to act to lim~t the ~cope of
- this inventionO
The following design2tions used in the Examples
have the following meaning-
Epoxy 1: 394-epoxycyclohexylmethyi-3,4 epoxycyclohexane
carboxylate
Epoxy 2: bis(3,4-ep3xycyclohexylmethyl) adipate
Epoxy 3: 2~(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)-
cyclohexane-meta-dioxane
HHPA: hexahydrophthalic anhydride
MTHP~: methyltetrahydrophthalic anhydride
Choline base: (2-hydroxy ethyl~ trimethyl ammonium hydrox-
ide, 45 percent concentra~ion in methanol.
Polyol 1: R-EO~CH2 ~
CH3 3
R ~ropane~ having a molecular weight of 6000.
Polyol 2: same formula as Polyol 1 but having a molecular
weight of 5,000,
Polyol 3: same formula as Polyol 1 but having a molecular
weight of 4,200.
Polyol 4: same formula as Polyol 1 but having a molecular
weight of 2,500.
Poly~l 5: same formula as Polyol 1 but having a molecular
weight of 1,500.
Polyol ~: same ~ormula as Polyol 1 but having a molecular
weight of 710.
1~3~ 13, 023
The procedures llsed to test ~che cured composi~
tion were as follows:
Physical Property Test Method
Heat distortion temperature ASTM D648~72
Thermal shock resls~ance (TSR) Union Carbide Corpor-
~'cion Publica~cion F~44429
Tensile strength
Elongation at break3 ASTM D-638
Tens ile modulus
Dielectric constant, 60 hertz ~t 100C} ASTM D-150
Dissipation Fac~or, 60 hertz at 100 C
Examples 1 and 2 and Controls A to D
In these Examples and Controls, the type and
amount of epoxicle (grams) and type and amount of polyol
(grams) as shown in Table I were mixed in a container at
abou~ 25C. In a separate container the amount (grams)
of hexahydrophthallc anhydrid2 and the amount (grams) of
choline base as shown in Table I were mixed at about 55C.
The contents of the two containers were combined and poured
into appropriate molds. The contents of the moLds were
then heated for 2 hours at 100C and then for our hours
at 160C~
The cured composition ~as then cut into test
~amples and tested for heat distortion temperature3 TSR,
tensile strength, elongation, tensile modulus, dielectric
constant and dissipation factor. The appearance of the
cured composition was noted. An appearance of opacity
indicates that a second phase has been formed.
The results are shown in Table I.
18.
36~
139023
.
~ 0~ ~
.a fD 3 ~ ~ J ~ o o ~ ~ O O t~
fD ~ ~ ~ P ~~ ~ O ~ O O ~e
~o n ,~ ~ ~~ ~ ~ r~
P It . ID r~ ~D
~- n g ~ ~~ ~ ~ ~ ~ ,_ ::
3 ~ D
O
F~ 00 'U
C~
~I
O ~ ~ O ~ 1~ ~ P
OD ~ o ~ O O p It
O
S-
o ~ :a
o o ,a 0 o
O ~ 9 ~ :~ ~;
~1 ~-- O p~ O ~ I I I t~ I I O ~
'~ Co O H
O ~I g ~ n
~ ~ I~~
~ ~ O
O ~ ~ ~ ~ 1
~ ~ D O ~a I ~ ~ I t ~ o I
~ ~ o ~ P
0~ Ln ~ I' '
O
~I tD O ~ ~ ~ 9 ~ ~ I O ~
O ,~ , P ,~ O
19 .
36~t~ 13, ~23
amples 3 and 4 and Controls F to H
In ~chese Examples and Controls, the ~ype and
amount of epoxide (grams) ~nd type and amount of polyol
(grams) ~s ~hown ill Table II wer mixed in ~ contairle~
at about 25C. In a separate container ~he
amount (grams) of hexahydrophthalic anhydrlde and ~che
amount (grams) of choline ba~e as ~hown irl Table II
were mixed at about 55 C . me contents o the two con-
tainers were combined and poured into appropriate molds.
The contents of the molds were then heated for 2 hours
at 100C and then for four hours at 160C.
The cured composition was ~hen cut lnto test
samples and tested for heat distortion temperature, TSR,
tensile strength9 elongation; tensile modulus, dielectric
constant and di ssipation factor. The appeara~ce of the
cured composition was noted.
The results are shown in Table II.
20.
3~ 13,023
.
p ~ ~ ~
D 'O ~ Y t~ O O ~g ~ a
~D O ~ ~ æ
.. ~ ~ ~ ~ ~ P ~ ~ O O O C~ ~ O
,
.. ~ ~ p g~
r
P
S-h O
P
O ~ ~ rt
4,
~" o
-
n
C~
O
C o ~
O o ~ , 3 o
I~ O CS~ 3 ~_
, O ~-
~ ~ ~ ~ It
0 3!~ 0 ~ O I O
. ~ o ~ Z ~ X ~_
~n o ~ V~
~n O
oo ~
~ ~ ~ o ,- a~ ,. ~ r
O ~ O~ ~ W O t1 ~
Ln ~ O C~ ~ C~
C~
O ~ ~ ~
~ W O ~D ~ ~ I ~n I I I ~ IW
O ~ ~ ~ ~ ~ O~ O
O . ~ W Go
W ~ O
O
O ~D o~D W ~ ~ O
O t~ " .~ ~ ~ 00
i~ (Jl O
n
~ a o ~ Cl~ 3
., , ~ . Ç~ ~1~ . ~ ~ ~ O r~
O ~U ~ ~ ;~
~-
,~ O :~:
2 ~ .
139 023
~ ~ ~3~
In these Examples ~ a mixture of epoxides of
the type and amount (grams j and Polyol 4 in the amount
(grams) as ~hown in Ta~le III were mixed ~t about 25C.
In a separate container the amount (grams) of
hexahydrophthalic anhydride and ~he amount (~rams) of
choline base as shown in Table III were mixed at about
25 C . The contents o the ltWQ containers were combined
and poured into appropriate molds. The con~ents of the
mol.d were then heated for 3 hours at 100C and then for
our hours at 160 C~
The cured composition was then cut ints test
samples and tested for heat distortion temperature7 TSR,
tensile strength, elongation, tensile modulus, dielectric
constant and dissipation factor. The appear~nce of the
cured composi~ion w~s noted.
The results are sh~wn in Table IIIo
22.
3~ 13, 023
g ~ O ~ ~ o t~ t~ 0 ~
rt rD ~ ~_ ~ ~ X ~ ~
C: ~ ~ ~ tD
~_ rt
r~ (D ~ P r
~ ~ 3 o ~o ~ ' co ~ o
o :3 rt O
" ~ ~ rD t n>
~h O
~ r~ ~
O P ~ rt
~ ~o ~ 3
D
I_
O W `'
~ o
O ~D 1~ 0 0 ~-- ~ It *`
cs`
~n
W W ~ O~ D ~I O 10
o ~ ~ D ~ ~ ~ O
g
:~
~ c~ ~
o ~ ~ ~J ~ ~ ~ ~ ~
o ~ `~ ~ ~ cs' rD ~ w ~ ~ ~ l~J
o `~ ~ . . .
o o~ c~ o 1~~I CJ' ~S cr ~ ~ ~ :~
~ r
~n ~ 1~1l W I~ D ~ H
O ~ ~0 ~ ~ ~ O ~ ~ I 0
o ~ o ~ o ~I
cr o
o
o ~ ~ ~ D W ~ ~ ~-- ~ 1`
~ ~ 8 ~n o ~ ~ ~
oo
O W W ~ O ~ ~ C~ ~ W
o ~ ~ ~
~_ ~n O O ~ P' O
O ~ ~n
Go o
?~
w ~J ~ o I ~
~ W o o ~ . . ~ . . . o~. ,,_
W ~ O
o ~
\
3 6 ~ 13;023
~ Y~ Z t~ l9
In these examples9 Epoxy 2 and Polyol 4 in the
amounts (grams) shown ~n Table IV were mixed ln ~ con-
tainer at about 25C, In a sep rate eontainer the
amount (~rams) of hexahydrophthali.c anhydrlde ~r methyl-
~etr~hydrophthalic anhydride ~nd amount (grams) of choline
base as shown in Table IY were mixed at about 25C. The
contents of the two containers were combined and poured
into ~ppropriate molds. The contents of the molds were
then heated for 2 hours at 100C and ~hen for four hours
a~ 160C.
The cured composition was then cut into test
~amples and tested for heat di~tortion temperature, TSR,
tensile strength, elongation~ tensile modulus, dielectric
constan~ and dissipation factor~ The appearance of the
cured composition was noted. The percent of polyol 4 in
the formulation is also shown.
The results arP shown in Table IV.
1~3~2
., , ,13; 0~3
. ~ 3 ~ ~ o ~ 1~ ~
~ ~ ., ~ ~ ~ ~ ~ ~ ~ ~
~ ~ ~ a o ~ ~ O
~ o ~ ~ 8 ~ R ~ ~ ~
~ O ~ ~ 5 Z~ ~"
g~ It p ~
P~ ~
ô
~ C~
Pg
~ ,
~3 ~ n o ~ o ~ O ~
O C~ ~ ~ ~J ~ ~ O ~D
~ 1-- 0
.,. ~ C~
~ ~n n ~- w
o ~ ~ ~ o 1_ ~ ~ ~ , 1
~ ~ ~n C~ C~7
OD
o ~ O ~ ,~ o ~ ~ ~ 1'--
,~, ~ O O C~
~ .
9 0
O ~ O ~ 1~9
~0 ~
25 . . - .
