Compositions – Electrically conductive or emissive compositions
Reexamination Certificate
1999-07-14
2001-11-13
Gupta, Yogendra (Department: 1751)
Compositions
Electrically conductive or emissive compositions
C252S501100, C252S502000, C252S512000, C252S518100
Reexamination Certificate
active
06315926
ABSTRACT:
The invention relates to an electrically conductive composition comprising a dispersion of electrically conductive particles and a radiation curable resin in a dispersing agent.
Such a composition is known from EP-A-591.951. EP-A-591.951 describes an electrically conductive composition consisting of a dispersion of polyaniline particles and a radiation curable resin in an organic solvent.
The drawback of the known composition is that an electrically conductive coating made of it shows increasing haze with improving electrical conductivity.
The aim of the invention is to provide a composition which does not exhibit said drawback.
This aim is achieved according to the invention in that the dispersion of electrically conductive particles contains a binder and an electrically conductive polymer and is stabilized by a non-ionic stabilization agent.
The radiation curable resin preferably contains the following components: a compound with a ethylenic unsaturation on an electron-attracting group (a), whether or not in combination with a compound comprising an ethylenic unsaturation on an electron-donating group (b), or an allyl-group-containing compound on an electron-donating group (c), or a mixture of compounds (b) and (c).
The ethylenic unsaturation on an electron-attracting group (a) is characterized by the following structure element.
X can for instance be one of the following groups: OR
4
, NR
4
R
5
, SR
4
, R
1
, R
2
, R
3
, can for instance be the following groups: H, C
1
-C
20
alkyl, aryl, substituted aryl, COOR
6
, CONR
6
R
7
, CH
2
COOR
6
, CH
2
OR
6
, OR
6
, NR
6
R
7
, SR
6
, Cl or CN. In these, R
4
, R
5
, R
6
and R
7
are chosen from the following groups:
H, C
1
-C
20
, alkyl (including linear and cyclic structures), aryl, substituted aryl, heterocycles containing O-, S-, N- or P-atoms, aromatic heterocycles containing O-, S-, N- or P-atoms, COY, CH
2
COY, CH
2
OY, CH
2
NYZ, CH
2
SY, CH
2
CH
2
OY, CH
2
CH
2
NYZ CH
2
CH
2
SY, CH
2
CH(CH
3
)OY, CH
2
CH(CH
3
)NYZ, CH
2
CH(CH
3
)SY, CH(CH
3
)CH
2
OY, CH(CH
3
)CH
2
NYZ, CH(CH
3
)CH
2
SY, (CH
2
O)
n
Y, (CH
2
NZ)
n
Y, (CH
2
S)
n
Y, (CH
2
CH
2
O)
n
Y, (CH
2
CH
2
NZ)
n
Y, (CH
2
CH
2
S)
n
Y, (CH
2
CH(CH
3
)O)
n
Y, (CH
2
CH(CH
3
)NZ)
n
Y, (CH
2
CH(CH
3
)S)
n
Y, (CH(CH
3
)CH
2
O)
n
Y, (CH(CH
3
)CH
2
NZ)
n
Y, (CH(CH
3
)CH
2
S)
n
Y, n being a number between 1 and 100. Y and Z can be chosen from the following groups: H, C
1
-C
20
alkyl (including linear and cyclic structures), aryl, substituted aryl, heterocycles containing O-, S-, N- or P-atoms, aromatic heterocycles containing O-, S-, N- or P-atoms. Derivatives of these compunds can also be used, such as for instance esters, urethanes, urea, thiourethanes and anhydrides.
Preferably the following compounds or combinations thereof are used: acrylates (X═OR
4
, R
1
═H, R
2
═H, R
3
═H), methacrylates (X═OR
4
, R
1
═CH
3
, R
2
═H, R
3
═H), acrylamides (X═NR
4
R
5
, R
1
═H, R
2
═H, R
3
═H), fumarates (X═OR
4
, R
1
═H, R
2
═COOR
6
, R
3
═H), maleates (X═OR
4
, R
1
═H, R
2
═H, R
3
═COOR
6
), itaconates (X═OR
4
, R
1
═CH
2
COOR
6
, R
2
═H, R
3
═H), citraconates (X═OR
4
, R
1
═CH
3
, R
2
═H, R
3
═COOR
6
), or mesaconates (X═OR
4
, R
1
═CH
3
, R
2
═COOR
6
, R
3
═H) and derivatives thereof, including for instance fumaramide-esters, maleamide-esters and fumaramides. Cyclic structures in which X is bonded to R
1
, R
2
or R
3
can also be used. Examples of such cyclic structure are the maleimides which are characterized by the following structure element:
in which R
4
can be chosen from the following groups: H, C
1
-C
20
, alkyl (including linear and cyclic structures), aryl, substituted aryl, heterocycles containing O-, S-, N- or P-atoms, aromatic heterocycles containing O-, S-, N- or P-atoms, COY, CH
2
COY, CH
2
OY, CH
2
NYZ, CH
2
SY, CH
2
CH
2
OY, CH
2
CH
2
NYZ CH
2
CH
2
SY, CH
2
CH(CH
3
)OY, CH
2
CH(CH
3
)NYZ, CH
2
CH(CH
3
)SY, CH(CH
3
)CH
2
OY, CH(CH
3
)CH
2
NYZ, CH(CH
3
)CH
2
SY, (CH
2
O)
n
Y, (CH
2
NZ)
n
Y, (CH
2
S)
n
Y, (CH
2
CH
2
O)
n
Y, (CH
2
CH
2
NZ)
n
Y, (CH
2
CH
2
S)
n
Y, (CH
2
CH(CH
3
)O)
n
Y, (CH
2
CH(CH
3
)NZ)
n
Y, (CH
2
CH(CH
3
)S)
n
Y, (CH(CH
3
)CH
2
O)
n
Y, (CH(CH
3
)CH
2
NZ)
n
Y, (CH(CH
3
)CH
2
S)
n
Y, n being a number between 1 and 100. Y and Z can be chosen from the following groups: H, C
1
-C
20
alkyl (including linear and cyclic structures), aryl, substituted aryl, heterocycles containing O-, S-, N- or P-atoms, aromatic heterocycles containing O-, S-, N- or P-atoms. Derivatives of these compunds can also be used, such as for instance esters, urethanes, urea, thiourethanes and anhydrides.
A compound with an ethylenic unsaturation on an electron-donating group (b) preferably is a vinyl ether, a vinyl ester, a vinyl amide, a vinylamine, a vinyl thioether or a vinyl thioester. Derivatives of these can also be used.
An allyl-group-containing compound on an electron-donating group (c) preferably is an allyl ether, an allyl ester, an allyl alcohol, an allyl amine or an allyl amide. Derivatives of these can also be used.
The amount of ethylenic unsaturation on an electron-attracting group (a) of the radiation curable resin is in general between 25% and 100%. The amount of ethylenic unsaturation on an electron-donating group (b) or an allyl-group-containing compound on an electron-donating group (c) or a mixture of these (b+c) of the radiation curable resin is between 0% and 75%, depending on the amount of ethylenic unsaturation on an electron-attracting group (a) of the radiation curable resin.
According to a preferred embodiment the radiation curable resin consists entirely of a compound with the ethylenic unsaturation on an electron-attracting group (a) or consists of a mixture of 50 mol % of a compound (a) and 50 mol % of a compound with an ethylenic unsaturation on an electron-donating group (b), or an allyl-group-containing compound (c) or a mixture of (b) and (c). The mol % mentioned here are relative to the radiation curable ethylenic unsaturation. The compound with the ethylenic unsaturation (a) preferably is an acrylate, a metacrylate, a maleate, a fumarate, an itaconate, a citraconate, or a mesaconate group.
The compound with the ethylenic unsaturation on an electron-attracting group (a) can be connected to polymers or oligomers via R
4
. Examples of such polymers or oligomers are polyurethanes, polyesters, polyacrylates, polyethers, hydrocarbon polymers such as for instance polyolefines which for instance contain units from the group of ethene, propene, butadiene and styrene, (co)polymers of cyclopentadiene, polysilicates, polycarbonates, polyvinyl esters, rubbers such as polyisoprene, natural rubber and polyepoxides. Mixed polymers such as polyether urethanes, polyester urethanes, polyether carbonates and polyepoxide esters. Combinations of polymers or oligomers can also be used. In case the ethylenic unsaturation on the electron-attracting group (a) comprises, besides R
4
, an additional functionality in the form of R
1
, R
2
or R
3
such as for instance COOR
6
, CONR
6
R
7
, CH
2
COOR
6
or CH
2
OR
6
, the ethylenic unsaturation can be incorporated in the polymer or oligomer chain. Examples of such polymers or oligomers are unsaturated polyesters, with fumarate, maleate, itaconate, citraconate or mesaconate functionalities having been used in the synthesis of the polymer or oligomer.
Preferably, the number of ethylenic unsaturation on an electron-attracting group on a polymer or oligomer is higher than 1.
The ethylenic unsaturation on an electron-donating group (b) or the allyl-group-containing compound on an electron-donating group (c) can be connected to the above-described polymers or oligomers via ether, ester amine or amide compounds or, in the case of bifunctional ethylenic unsaturation on an electron-donating group or a bifunctional allyl compound, can also be incorporated in a polymer or oligomer chain.
Besides the above-described ethylenic unsaturations on or in a polymer or oligomer, the
DSM N.V.
Gupta Yogendra
Hamlin Derrick
Pillsbury & Winthrop LLP
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