PHOTO-INITIATEURS

PHOTOINITIATORS

Abrégé anglais

ABSTRACT OF THE DISCLOSURE
Halogen onium salts, and onium salts of Group VA and
V1A elements having an MF6-anion, where M is selected
from P, As and Sb, have been found to exhibit unusual
activity under ultraviolet light. These onium salts can
be employed as cationic photoinitiators when used with
a variety of organic resins and cyclic organic compounds.

Revendications

The embodiments of the invention in which an exclu-
sive property or privilege is claimed are defined as follows:
1. Photoinitiators of the formula,
Y+ (MF6)-
where M is an element selected from the class consisting
of P, As and Sb, and Y is a cation selected from the class
consisting of
<IMG> ,
where R is a monovalent aromatic organic radical, R2 is
a monovalent organic aliphatic radical selected from alkyl,
cycloalkyl and substituted alkyl, R3 is a polyvalent organic
radical forming a heterocyclic or fused ring structure
selected from aliphatic radicals and aromatic radicals, R4
is a monovalent organic aliphatic radical selected from
alkyl, alkoxy, cycloalkyl and substituted derivatives
thereof, R5 is a polyvalent organic radical forming an
aromatic heterocyclic or fused ring structure with Z, X is a
Group V1a element selected from sulfur, selenium and tellurium,
Z is a Group Va element selected from N, P, As, Sb and Bi, c is
a whole number equal to 0 or 3, d is a whole number equal to 0
to 2 inclusive, e is a whole number equal to 0 or 1, where the
sum c + d + e times the valence of the radical associated there-
with is equal to 3; f is a whole number equal to 0 to 4 inclusive,
g is a whole number equal to 0 to 2 inclusive, and h is a whole
number equal to 0 to 2 inclusive, and the sum of f + g + h times
the valence of the radical associated therewith is equal to 4.
26

2. Group VA salts of the formula,
<IMG>
where M is an element selected from the class consisting of
P, As and Sb, R is a monovalent aromatic organic radical, R4
is a monovalent organic aliphatic radical selected from alkyl,
alkoxy, cycloalkyl and substituted derivatives thereof, R5 is
a polyvalent organic radical forming an aromatic heterocyclic
or fused ring structure with Z, Z is a Group VA element selected
from N, P, As, Sb and Bi, f is a whole number equal to 0 to 4
inclusive, g is a whole number equal to 0 to 2 inclusive, and
h is a whole number equal to 0 to 2 inclusive, and the sum of
f + g + h times the valence of the radical associated therewith
is equal to 4.
3. An ammonium salt in accordance with Claim 2,
where M is phosphorus.
4. An ammonium salt in accordance with Claim 2,
where M is arsenic.
5. An ammonium salt in accordance with Claim 2,
where M is antimony.
6. An ammonium salt in accordance with Claim 2,
selected from the formulae
<IMG> ,
<IMG> ,
27

<IMG>
<IMG> .
7. An ammonium salt in accordance with Claim 2
wherein the cationic portion thereof has the formula
<IMG> ,
8. A phosphonium salt in accordance with Claim 2,
where M is phosphorus.
9. A phosphonium salt in accordance with Claim 2,
where M is arsenic.
10. A phosphonium salt in accordance with Claim 2,
where M is antimony.
11. A phosphonium salt in accordance with Claim 2,
wherein the cationic portion has the formula
<IMG> .
12. A phosphonium salt in accordance with Claim 2,
wherein the cationic portion thereof has the formula
28

<IMG> .
13. Group V1A salts of the formula,
<IMG>
where M is an element selected from the class consisting of
P, As and Sb, R is a monovalent aromatic organic radical,
R2 is a monovalent organic aliphatic radical selected from
alkyl, cycloalkyl and substituted alkyl, R3 is a polyvalent
organic radical forming a heterocyclic or fused ring structure
selected from aliphatic radicals and aromatic radicals, X is
a Group V1A element selected from sulfur, selenium and tellurium,
c is a whole number equal to 0 or 3, d is a whole number equal
to 0 to 2 inclusive and 3 is a whole number equal to 0 to 1,
where the sum of c + d + 3 times the valence of the radical
associated therewith is equal to 3.
14. A sulfonium salt in accordance with Claim 13,
where M is phosphorus.
15. A sulfonium salt in accordance with Claim 13,
where M is arsenic.
16. A sulfonium salt in accordance with Claim 13,
where M is antimony.
17. A sulfonium salt in accordance with Claim 13
having the formula
<IMG> .
29

18. A sulfonium salt in accordance with Claim 13
having the formula
<IMG> .
19. A sulfonium salt in accordance with Claim 13
having the formula
<IMG> .
20. A sulfonium salt in accordance with Claim 13
wherein the cationic portion has the formula
<IMG> .
21. A sulfonium salt in accordance with Claim 13
wherein the cationic portion has the formula
<IMG> .
22. A sulfonium salt in accordance with Claim 13
wherein the cationic portion is selection from the cations of
the formulae
<IMG> ,
and

<IMG> .
23. A sulfonium salt in accordance with Claim 13
wherein the cationic portion has the formula
<IMG> .
24. A sulfonium salt in accordance with Claim 13
wherein the cation portion has the formula
<IMG> .
25. A sulfonium salt in accordance with Claim 20,
21 or 22 wherein the anionic portion is AsF6-.
31

Description

RD-7735
10~0;~41
The present invention relates to onium salt photoini-
tiators of halogen, Group Va and Vla elernents having an
MF6 anion, where M is an element selected from P, As and
Sb.
The photoinitiator compositions of the present
invention can be used in combination with various organic
resins, such as epoxy resins, to produce UW curable com-
positions. The photoinitiators of the present invention
are included by the formula
(1) Y (MF6)
where M is an element selected from P, As and Sb, and Y
is a cation selected from
~(R)a(R )b Q ~ :
~R)C(R )d(R3)e X~
'
~ .
~R) f(R ) (R )h Z ~ '

10 ~ RD-7735
where R is a monovalent aromatic organic radical, R is
a divalent aromatic organic radical, R2 is a monovalent
organic aliphatic radical selected from alkyl,
cycloalkyl and substituted alkyl, R3 is a polyvalent
organic radical forming a heterocyclic or fused ring
structure selected from aliphatic radicals and aromatic
radicals, R4 is a monovalent organic aliphatic radical
selected from alkyl, alkoxy, cycloalkyl and substituted
derivatives thereof, R5 is a pol~valent organic radical
forming an aromatic heterocyclic or fused ring structure
with Z, Q is a halogen radical such as I, Br, Cl, etc., X
is a Group Vla element selected from sulfur, selenium
and tellurium, Z is a Group Va element selected from
~, P, As, Sb and Bi, a is a whole number equal to 0
or 2, b is a whole number equal to 0 or 1, the sum of
a + b is equal to 2 or the valence of Q, c is a
whole number equal to 0 or 3, d is a whole number
equal to 0 to 2 inclusive, e is a whole number equal to
0 or 1, where the sum of c + d + e times the valency
of the radical associated therewith is equal to 3;
f is a whole number equal to 0 to 4 inclusive, g
is a whole number equal to 0 to 2 inclusive, and
h is a whole number equal to 0 to 2 inclusive, and the
sum of f + g + h times the valency of the radical associated
therewith is equal to 4.
Radicals included by R can be the same or different,
aromatic carbocyclic or heterocyclic radical having from 6

~O~Z41
RD-7735
to 20 carbon atoms, which can be substituted with from 1 to
4 monovalent radicals selected from C(l 8) alkoxy, C(l 8)
alkyl, nitro, chloro, etc., R is more particularly phenyl,
chlorophenyl, nitrophenyl, methoxyphenyl, pyridyl, etc.
Radicals included by Rl are divalent radicals such as
~CH )
R2 radicals include C(l 8) alkyl such as methyl, ethyl,
etc., substituted alkyl such as -C2H4OCH3, -CH2COOC2H5,
-CH2COCH3, etc. R radicals include such structures as:
J ' ~OJ
~, 13 . ~ . etc
/
., ' ~
R4 radicals include C(1_8) alkyl, C(3_8) y
stituted alkyl such as haloalkyl, for example, chloroethyl;
alkoxy such as OCH2C6H5 and OCH3; alkoxyalkyl such as
-C2H4OCH3 , etc Radicals included by R5 are, for example,
~ 3

lV8l)241
RD- 773s
X~ '
~ <Q~'
R'-N
N ~ N
R'
where Q' is selected from 0, CH2, N, R and S; Z is selected
: R'
from -O-, -S- and -N-, and R' is a monovalent radical
selected from hydrogen and hydrocarbon.
Halonium salts included by Formula 1 are, for
example, CH3 C H5
~) _ [~ _
: I PF6 ~ AsF6
~' ~
CH3 C2H5
'

1080Z4~
RD 7735
PF6 ~ SbF6
2 ~) AsF6
Group VIa onium salts included by Formula 1
are, for example,
: ~H3 H3
HO ~ ~ AsF6
3 H3
~ C-CH2- ~ PF6-
02N{~C-CH2-~ A9F6-
Br ~ C-CH2- ~ 6
<~ S bF6
, ~
~ -C-CH2S O PF ~
~ ~ A9F6 SbF6 , etc.
_5_

RD--7735
~08(~Z~l
Group Va onium salts included by Formula 1 are,
for example,
L ~ 2 C `\ 1 SbF6 ~ ~ N-CH2C ~ I PF-
N -CH2C ~ AsF6-
H ~ ~ As ~ ; ~ ~ 3
r ~ ¦ 6
L CH -C ~
+
P-CH--C-(~ I AsF ~
~(( ~ CH 2--c o o c 2 H~3 PF 6
As shown in my U.S. Patent 3,981,897, dated September ~
21, 1976, and assigned to the same assignee as the present inven-
tion, where Y in Formula 1 contains a Q radical, the photoinitia~r
can be made by effecting contact under aqueous conditions between
an arylhaloniumbisulfate and the corresponding hexafluoro acid
-~ -- 6 --

~08~4~
RD-7735
or salt, s~ch as yl M F6, where yl can be hydrogen, an alk~li
metal ion, alkaline earth metal ion or transition metal ion.
In additlon to the aboYe-described metathesis for
making the corresponding halonium salts, the halonium salts
of the present invention, also can be prepared by using
silver compounds, such as silver oxide, or silver tetra-
fluoroborate, which were reacted with the appropriate
diarylhalonium salt, as shown by M. C Ca~erio et al., J.
Am Chem. Soc 81, 336 (19S9) or M C. Beringer et al.,
J Am Chem. Soc 81, 342 (1959). Methods for making Group
VIa compounds, such as sulfonium, selenium and tellurium
compounds, where Y of Formula 1 contains an X radical can
be made by procedures shown in J W. Knapczyk and W E
McEwen, J Am Chem. Soc., 91 145, (1969); A L Maycock
and G A Berchtold, J Org Chem., 35 No 8,2532 (1970);
H. M Pitt, U S Patent 2,807,648, E Goethals and P.
De Radæetzky, Bul. Soc Chim Belg , 73 546 ~1964); H. M.
Leichester and F. W. Bergstrom, J Am Chem. Soc , 51
3587 (1929), etc.
Among the procedures which can be used to make
Group Va onium salts, arsonium, antlmonium and bimuthonium
salt, where Y in Formula 1 is a Z radical can be found in
Goerdeler, Methoden der Organishen Chimie 1l/2 , 591-640
(1958) and K Sasse, idid, 12/1 79-112 (1963).
--7--

108~)2~
RD-7735
The fol~owing examples are given by way of illu9-
tration and not by way of limitation. All parts are by
weight.
Example 1
There was added a cooled solution of about 100
ml of acetic ac i d and 70 ml of concentrated sulfuric
acid to a suspension of 100 g of potassium iodate in 100
ml of acetic anhydride and 90 ml of benzene During the
addition, the mixture was stirred and maintained below
5C. When the addition was complete, the reaction mixture
was allowed to warm to room temperature and stirred for 48
hours There was then added 400 ml of distilled water.
The aqueous portion of the reaction mixture was extracted
three times with diethyl ether and petroleum ether to re-
move unreacted organic materials A pale yellow crystalline
product formed upon addition of ammonium chloride to the
aqueous reaction mixture There was obtained a 48% yield
of diphenyliodonium chloride having a m.p. of 180-185C.
After recrystallization, the pure salt had a m.p. of 228-
229C
- A photoinitiator was prepared within the scope
of Formula 1, having a Q containing Y cation as follows:
A mixture of 20 g of moist, freshly prepared Ag20,
10 ml of water and 31.7 g of diphenyliodonium chloride was
ground together in a slurry. The wet mixture was filtered

1080241
RD-7735
and washed with water to produce 360 ml of filtrflte. The
filtrate was cooled until a substantial amount of the solu-
tion had frozen. 'rhere was slowly added 25 ml 45-50% HBF4
cooled to -15C, The cold solution was stirred and allowed
to warm to room temperature, A white crystalline solid
separated and was collected by filtration, There was
obtained a 60% yield of diphenyliodonium fluoroborate, m,p,
136C when the solid was dried overnight in vacuo at 60C,
Replacement in the above procedure of HBF4 with
HPF6 and HSbF6, yielded the corresponding diphenyliodonium
hexafluorophosphate mp, 138-141C, and diphenyliodonium
hexafluoroantimonate mp 58-57C,
The salts were dissolved in acetonitrile (3 g
salt to 10 ml acetonitrile) and then added to 4-vinyl-
cyclohexene dioxide such that there was present 3% by weight
of the salt, The solutions were coated as 3 mil films onto
glass slides and exposed to W irradiation from a GE H3T7
lamp at a distance of 6 inches, The minimum time required
to produce a tack-free film was recorded as the cure time,
~ 20 By tack free is meant that the film was no longer tacky
- and an imprint was not left when a thumb was impressed on
its surface,
Under these conditions, the following results
were recorded:

1080Z41
RD-7735
Salt Cure Time (sec.)
BF4 30
6 20
6 5
Clearly, those salts po~sessing the MF6 anion
were much faster than the salts having the BF4 anion.
Example 2
A solution of about 200 parts of sulfuric acid
in about 300 parts of acetic acid was added at a temperature
between 0 to 3C to a mixture,while it was being agitated,
of 200 parts of potassium iodate, about 300 parts of toluene,
about 900 parts of acetic acid, and about 400 parts of acetic
anhydride. The mixture was then stirred for 11 hours after
all of the sulfuric acid and the acetic acid had been added.
The resulting inorganic salts were removed by filtration
and then washed with a small amount of cold glacial acetic
acid. A pale yellow solution was obtained which was diluted
to twice its volume with water and extracted three times
with ether. A small amount (0~3 part) of sodium sulfide
was added as a reducing agent.
Based on method of preparation, there was obtained
a quantitative yield of 4,4'-dimethyldiphenyliodonium
bisulfate. A slightly warm solution of substantially equal
-10-

1080Z41
RD- 773s
molar amounts of 4,4'-dimethyldiphenyliodonium bisulfate
and potassium hexafluoroarsenate was allowed to cool.
There was obtained a white crystalline deposit. The pro-
duct was filtered and washed with distilled wa~er. A second
crop of crystals was obtained on further standing. After
the crystals were dried overnight, there was obtained 27
parts of a product having a melting point of 148-152C.
Recrystalli~ation of the product from a water ethanol mix-
ture resulted in a product having a melting point of 163-
166C Based on method of preparation and NMR spectra and
elemental analysis for C14H14IAsF6 calculated: percent
C, 33 74; percent H, 2 81; percent As, 15.06, found: percent
C, 33 70; percent H, 2.92; percent As, 15.28, the product
was 4,4'-dimethyldiphenyliodonium hexofluoroarsenate
By a similar procedure, treatment of 4,4'-
dimethyldiphenyliodonium bisulfate with KSbF6 and KPF6
resulted in 4,4'-dimethyldiphenyliodonium hexafluoro-
antimonate m.p. 75-80C and 4,4'-dimethyldiphenyliodonium
hexafluorophosphate mp 169-172C.
4,4-dimethyldiphenyliodonium tetrafluoroborate
was prepared by treatment of the 4,4'-dimethyldiphenylio-
donium bisulfate with ammonium chloride in water and isolat-
ing the resulting 4,4'-dimethyldiphenyliodonium chloride.
The dry chloride salt (34.5 g) was slurried together with
20 g freshly prepared silver oxide and 10 ml water. The
-11-

108UZ41
RD-7735
mixture was then filtered and washed to produce 360 ml
filtrate The filtrate was cooled until nearly the entire
solution had been frozen, and then a cold solution of 25 ml
45-50% HBF4 was added. The mixture was stirred snd 810wly
allowed to warm to room temperature. The white crystalline
product which separated was 4,4'-dimethyldiphenyliodonium
fluoroborate mp 95-100C
A comparative study of the cure ratio was performed
on 3% of each of the salts dissolved directly in 4-vinyl-
cyclohexene dioxide, as described in Example 1. The results
obtained were a~ follows:
Salt Cure Time (~ec.
H3 ~ 1 BF4 60
6 20
" AsF6 5
: :
" SbF6 3
The above results chow that the MF6 salts provided
unexpected results over the prior art BF4 salt.
Example 3
Triphenylselenonlum chloride was prepared accord-
ing to the procedure of H. M Leicester and F. W Bergstrom,
J Am. Chem Soc., 51 3587 (1929) starting with diphenyl
selenide. The corresponding fluoroborate, hexafluoroarsenate
-1~-

1080241
RD-7735
and hexafluoroantimonate salts were prepared by adding
sodium hexafluoroarsenate, sodium tetrafluoroborate or
potassium hexafluoroantimonate to an aqueous solution of
triphenylselenonium chloride. The products which contained
Y radicals as shown in Formula l,where Y was an X contain-
ing cation, were white crystalline solids which were dried
in vacuo.
Three percent solutions of the above salts in 4-
vinylcyclohexene dioxide were cured as 2 mil films at a
distance of six inches from a GE H3T7 lamp. The following
cure times were observed:
Salt Cure Time
( 6 5)3 4 10 sec.
( 6 5)3 s 6 5 sec
(C6H5)3Se sbF63 sec.
The above results show that the hexafluoro salt
is a superior photosensitizer with respect to cure time as
compared to the tetrafluoroborate salt.
Example 4
Additional curable compositions were prepared
using the epoxy resin mixture of Example 1 and a variety
of phosphonium salt~ as shown as follows where cation is
the organic portion corresponding to Y of Formula 1, where
Y contains a Z radi~al, anion is the Lewis Acid por~ion,
-13-

1~8024~
RD-7735
m.p. is the melting point of the crystalline onium salt and
"cure tLme" is as previously defined.
~ .
.. . . . .
.
.
- .
'' ' :' ,
.
`'` ~. .

108VZ~
RD- 773s
U~
a cr~ O
~)
,~ r~ c~r~ ~ C`
c~ ~ ~a~ o o ~
O o ~ ~ .~ ~ o C~l
U~ I I ~ I I ~ I
. ~ U~ O~ ~ ~ I`
o ~
a
ol, , ' ~ ' ~D,
C ~ ~ D a~
¢ ~ ' ¢ P~ ~ ~
'1 o I o ~ 0 ~ I
i~ ~
V ~, +p~ +~ +~, +~, +~ _
~ ~ ~
1--1 H H ~ ~ H H ~
H H ~ 1 H
~>
-15-

108~Z4~
RD-7735
Example 5
In accordance with the procedure of Example 1,
additional iodonium salts were prepared as sh~wn by the
~ I J) CH3 (~ / O
following table, where t is -C-CH3 and
CH3
5 3
i~ ~ H . .
CH3
... . .
..
!

1080Z41
RD-7735
o o. oo.~ ~
~ '`' . o ~
U~ ~ ~D
a~ o ~ _l ~ ~
a~ C a~ ~ o
u, ~ ~ . ~; ~ ~ ~ . ~ .~ . . ~n . .
~ U~ U~ ~ _~ o o~ ~ ~ ~ e
C~ C`~ C~l _
X ~ ~ ~ ~ ~ ~:
~-n
_~ ~ ~ oo ~ ~ U~ ~ C~l ~ U~
'D ~ C~ ~ ~~ C~ I~ ~o
~ ~ C~ ~ ~ C~ ~ ~ ~ o
E3 ~ `J `;t ~ ~ .. ~ ~ C`~
~ C U~ U ~ ~ ~
~ ~C ~ ~ ~ tO~
.` X O O C~ O O O
~ O I~ C~J O oo~ ~S)
X O O C~l _l O~ ~I
~ CO~ 0 ~ t'O CO ~0
ct: oC') r` t` Ir~ ~ u
~ ~ l l l ll l
H ~) ~O ~ ~D ~
O . -I _1 ~ ~ ~1
a ~ ,
o ~0 ~'0 1:~ ~`S) ~o t~
~C P~ ¢ ~ P~ ~1: ¢
,~ + I 1 + I + I ~ I + I
~ ~1 ~ ~ ~ ~
C.?
-17-

11~8(3'~1
RD- 7 7 3 5
~o
V~ ~00
C`J~ ¢
.,, ~ ~ ~ o~ U~
o o
I~ ~ C~ ~ ~ ~ ~ u~ U~
~:: C`J ~ O r` ~ o
I Z;0~ 0~ ~ ~ ~t
O I~ U~ l
oo O r~ oo l ~ O
E3 t) . . ~ ~) O O ~ u~ ~
.... .... .... ....
U ~ U
C ~ ~ ~ ~ ~ ~
o ~ o ~ o C~ o
X ô ô ô ôô
o o o ~ o o~
_ ~ ô ~ , u~ r~
X _, _, ~_ ~ `_ _,
~ ~o Ul ~ U~
_ U~ o
C~l ~ ~ ~o U~
- ~ ~ ~ ~
~D ~o
~: ~ ~ c`l ~
r~ ~ ~ ~ k~ ~
g ;~
-18-

10802~1
RD-7735
The above halonium salts were found to exhibit
substantially the same utillty with respect to a faster
rate of cure of 4-vinylcyclohexene dioxide a~ compared to
prior art photolnitiators as shown for Example 1.
ExamPle 6
Several sulfonium hexafluoroarsonium salts,.
sulfonium hexafluoroantimonate salts and selenium hexafluoro-
arsonium salts, where Y in Formula 1 is an X containing
cation, were prepared by adding the corresponding anion
in the form of the acid or salt, such as sodium hexafluoro-
arsenate to the corresponding cation structure, such as an
aqueous solution of tri(3,5-dimethyl-4-hydroxy)phenyl
sulfonium chloride. The procedure described by H. M
Leicecter and F, W, Bergstrom, J, Am. Chem Soc 51 3587
(1929) was employed. The following table shows the results
obtained
. ~ , ~ , . _ _ _
: .
~P~
' ,
. .

1~8l)241
RD-7785
U~
u~ u~ ~ ~ In
.,, o~ ~ U~ U~
U~ o ~ o~
~:
o ~ a~
. ~ o~
. . U
al ~ ~ ~ a~
~1 .~................... ....
t. ~ ~ ~
~ g ~d ~
u ~o u o
ô~
o o o o o o o
o o o o ~ I~ U~
~ o ~ ~o ~ .
_ ~ ~ o
~ ~ ~ CS~ ~ C~l,
X ~ ,
~ o ~ a~ ~ ~ o ,~
X o oo 1~ u~ `D 00
~: ~ ~ ~ C~ C~l C`J
E~
¢ C~ U~ U~
V~ o
. l
U~
:~ . U~
o ~:
tn
o ~o
~r~
~¢ ¢ ¢
:~ ~ +U~ .
U V ~ W
-20-

1080Z4~
RD-7735

~ ~ ~ U~
~ ::C o a~
s
~)
.... ....
t~
~aO ~
X o ~ U~ o ~ o o o o o o
o~ o~ oo oo oo
a~ oo ~ o~ I~ e~l r~
..
_ o~ o~C~l~ ~o~ ~o ~
X ~ ~ _,_, _,_, ~ ~,
o~ o~ o oo o X o X
~: u~ u~ O ~ O ~ O
~ C~ ~ ~ C~I ~ ~ ~ ~
., ~ ~ ~ o ~ ~
~) 00 ~ ~ ~D
~ ~ o ~ ~ o
:, . o~ ~ ~ ~ ~D
~ l
O ~D
.~ ~ ~ ~D ~ ~
e ~
-21 _

1080Z4~
RD-7735
. It was found that 4-vinylcyclohexene dioxide
compositions containing the above onium salts exhibited
a faster rate of cure, as compared to comparable prior art
tetrafluoroborate anium salts.
Example 7
In addition to the aforementioned haloni~m salt - -
and sulfonium ~alts falling within the scope of Formula 1,
where Y is a Q containing and X containing cation, several
phosphonium salt~ and ammonium salts were prepared by the
procedure shown by J Goerdeler, Methoden der Organishen
Chimie, ltl2 591-640 (1958) The latter onium salts, where
Y in Formula 1 is a cation containing a Z radical are shown
as follows:
.. . . .... .. . . . . _
,
', ',,.' ~ . ~ '
. ~ : .
; ~
~ .

108~)~4~ .
RD-7735
0~ ~ ~o
(n P~ . ~ ~ P~ O
.~ ~ ~ U~ U~U~ U~
~ o o
C~l ~1 ~O ~ `D 1~
~ X . . ~ ~ . .
¢ ~ ~ . .
~ o
J~ ~ u~ I~ o~ co r~
~ C~ . . C~ . . C~ .
a~ a~ o~. ~ ~ o o
U~ U~ U~ U~ ~ U~
.... .... ....
tJ ~ U ~ U
,-1 ~ ~ ~
o ~J o t~ o
~ 4~ ~U
,~
.' ~d O
. C~ . _
X
U~ _` ~D I~ ~
C~ o cr~
X ~ o
P~
~ l ~
~1 ~ ~D ~
~C U~
~1 -
'1 ~
-23--

RD--7735
1~)802
~ ~ 0~l ~ Z ~1
~ ~ ~r ~ ~ ~ ~
~ or~ oo ~o
o
~1 ~ ~ ~ ~ ~ '.
$ Ln ~D ~ ~ a~
~ ~ ~ o~i
~ .... .... ....
~,~ V~ ~,~
~, o ~, o ~, o
æ~ O
æ U~
~ ~9
~ ~ .
: ol , I~D '~
~1 ~9
-- 24 --

108~4~ RD-7735
In addition to using the photoinitiators of the present
invention for curing epoxy resins, these onium salts of
halogen, Group Va and Vla elements can be used to polymerize
a varity of cyclic organic compounds and cyclic organo-
silicon compounds as shown in Canadian Serial Numbers
226,108, 226,107, and 266,109 filed May 2, 1975 and
assigned to the same assignee as the present invention.
- 25