Heat sensitive recording material

Details Heat sensitive recording material Heat sensitive recording material

2001-10-01

2003-09-23

Hess, Bruce H. (Department: 1774)

Record receiver having plural interactive leaves or a colorless

Having a colorless color-former, developer therefor, or...

Identified organic electron acceptor other than phenolic resin

C503S209000, C514S592000, C514S596000, C514S597000, C514S598000

Reexamination Certificate

active

06624117

ABSTRACT:

The present invention relates to heat sensitive recording materials. It more particularly relates to such recording material in the form of a supporting substrate, for example, a paper sheet, synthetic paper sheet or plastic resin film coated with colour-forming systems comprising a colorless or pale coloured electron donative compound (colour forming compound) and an organic electron acceptor (developer).
Heat sensitive recording has conventionally been used as a system for recording transferred information through the mediation of heat, by utilising a colour reaction between a colour forming compound and a developer.
The properties which are most desirable in a colour forming material, in addition to the effective development of colour, are thermal response, background whiteness and image stability, especially light fastness of the developed colour, heat and moisture fastness of the developed colour, oil fastness of the developed colour, plasticiser resistance of the developed colour and water fastness of the developed colour.
A need exists to improve the above properties and to improve the archival capabilities of such recording materials. It is an object of the present invention to provide heat sensitive recording materials with improved properties, especially to provide an increase in image stability whilst improving the background whiteness of the paper before imaging and the background whiteness of the undeveloped portion after imaging.
The present invention is directed to a heat sensitive recording material, comprising
a) at least one colour forming compound, and
b) at least one developer of the formula
 wherein
R
1
is unsubstituted or substituted phenyl, naphthyl or C
1
-C
20
alkyl,
X is a group of the formula
A is unsubstituted or substituted phenylene, naphthylene or C
1
-C
12
alkylene, or is an unsubstituted or substituted heterocyclic group,
B is a linking group of formula —O—SO
2
—, —SO
2
—O—, —NH—SO
2
—, —SO
2
—NH—, —S—SO
2
—, —O—CO—, —O—CO—NH—, —NH—CO—, —NH—CO—O—, —S—CO—NH—, —S—CS—NH—, —CO—NH—SO
2
—, —O—CO—NH—SO
2
—, —NH═CH—, —CO—NH—CO—, —S—, —CO—, —O—, —SO
2
—NH—CO—, —O—CO—O— and —O—PO—(OR
2
)
2
, and
R
2
is unsubstituted or substituted aryl or benzyl or C
1
-C
20
alkyl,
with the proviso, that, if B is not a linking group of formula —O—SO
2
—, R
2
is unsubstituted or substituted phenyl, naphthyl or C
1
-C
8
alkyl and that, if B is —O—, R
2
is not alkyl.
R
1
as phenyl or naphthyl can be unsubstituted or substituted by, for example, C
1
-C
8
alkyl, C
1
-C
8
alkoxy or halogen. Preferred substituents are C
1
-C
4
alkyl, especially methyl or ethyl, C
1
-C
4
alkoxy, especially methoxy or ethoxy, or halogen, especially chlorine. R
1
as naphthyl is preferably unsubstituted. R
1
as phenyl is preferably substituted, especially by one of the above alkyl substituents.
R
1
as C
1
-C
20
alkyl can be unsubstituted or substituted by, for example C
1
-C
8
alkoxy or halogen. Preferred substituents are C
1
-C
4
alkoxy, especially methoxy or ethoxy, or halogen, especially chlorine. R
1
as C
1
-C
20
alkyl is preferably unsubstituted.
Preferably, R
1
is phenyl which is unsubstituted or substituted by C
1
-C
8
alkyl, C
1
-C
8
alkoxy or halogen. Of most importance are the substituted phenyl groups. Highly preferred are phenyl groups which are substituted by C
1
-C
4
alkyl, preferably by methyl.
X is preferably a group of the formula
especially a group of the formula
A as a phenylene or naphthylene group can be unsubstituted or substituted by, for example, C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halogen-substituted C
1
-C
8
alkoxy, C
1
-C
8
alkylsulphonyl, halogen, phenyl, phenoxy or phenoxycarbonyl. Preferred alkyl and alkoxy substituents are those containing 1 to 4 carbon atoms. Preferred substituents are C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkyl-sulphonyl or halogen. A as a naphthylene group is preferably unsubstituted.
A as a heterocyclic group is preferably pyrimidylene which is unsubstituted or substituted by C
1
-C
8
alkyl, especially by C
1
-C
4
alkyl.
A as a C
1
-C
12
alkylene group is preferably C
1
-C
8
alkylene, especially C
1
-C
4
alkylene.
Preferred groups A are phenylene groups which are unsubstituted or substituted by C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halogen-substituted C
1
-C
8
alkoxy, C
1
-C
8
alkylsulphonyl, halogen, phenyl, phenoxy or phenoxycarbonyl, especially C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkylsulphonyl or halogen.
Highly preferred groups A are phenylene groups which are unsubstituted or substituted by C
1
-C
4
alkyl or halogen, especially unsubstituted phenylene groups.
Preferred linking groups B are those of formulae —O—SO
2
—, —SO
2
—O—, —SO
2
—NH—, —S—SO
2
—, —O—, —O—CO— and —O—CO—NH—, especially linking groups of formulae —O—SO
2
—, —SO
2
—O— and —SO
2
—NH—. Highly preferred are the linking groups B of formula —O—SO
2
— and —O—.
R
2
as aryl is preferably phenyl or naphthyl which can be unsubstituted or substituted by, for example, C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halogen-substituted C
1
-C
8
alkoxy or halogen. Preferred alkyl and alkoxy substituents are those containing 1 to 4 carbon atoms. Preferred substituents are C
1
-C
4
alkyl and halogen. R
2
as naphthyl is preferably unsubstituted.
R
2
as benzyl can be substituted by the substituents given for R
2
as phenyl or naphthyl. Unsubstituted benzyl is preferred.
R
2
as C
1
-C
20
alkyl is preferably C
1
-C
8
alkyl, especially C
1
-C
6
alkyl, and can be unsubstituted or substituted by, for example, C
1
-C
8
alkoxy, halogen, phenyl or naphthyl. Preferred are the unsubstituted alkyl groups, especially C
1
-C
4
alkyl.
Preferred groups R
2
are C
1
-C
6
alkyl; halogen-substituted C
1
-C
6
alkyl; phenyl-substituted C
1
-C
6
alkyl; naphthyl-substituted C
1
-C
6
alkyl; phenyl which is unsubstituted or substituted by C
1
-C
8
alkyl, halogen-substituted C
1
-C
8
alkyl, C
1
-C
8
alkoxy-substituted C
1
-C
8
alkyl, C
1
C
8
alkoxy, halogen-substituted C
1
-C
8
alkoxy or halogen; naphthyl and benzyl which is substituted by C
1
-C
4
alkyl or halogen.
Highly preferred groups R
2
are C
1
-C
4
alkyl; halogen-substituted C
1
-C
4
alkyl; phenyl which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen; naphthyl and benzyl which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen, especially phenyl which is unsubstituted or substituted by C
1
-C
4
alkyl.
Preferred are developers of formula (1), wherein.
R
1
is phenyl which is substituted by C
1
-C
4
alkyl, preferably by methyl,
X is a group of the formula
A is phenylene which is unsubstituted or substituted by C
1
-C
8
alkyl or halogen, preferably unsubstituted phenylene, like 1,3-phenylene,
B is a linking group of formula —O—SO
2
— or —O— and
R
2
is phenyl, naphthyl or benzyl which is unsubstituted or substituted by C
1
-C
4
alkyl or halogen, especially phenyl which is substituted by C
1
-C
4
alkyl.
The compounds of formula (1) can be prepared in accordance with schemes 1-3 below;
where R
1
, R
2
, A, B and X are as defined above and E is alkyl or aryl.
Furthermore, in the case where the species H
2
N—A—B—H is available the compounds of formula (1) can be prepared in accordance with scheme 4 below;
In the case of schemes 1, 2 and 4 the R
1
-sulphonylisocyanate (or R
1
-sulphonamide) is reacted with R
2
-amine (or R
2
-isocyanate) in the presence or absence of an organic solvent. Preferably in the presence of an (apolar or polar) aprotic solvent such as aromatic hydrocarbons, chlorinated aromatic hydrocarbons, aliphatic or alicyclic hydrocarbons, chlorinated hydrocarbons, dialkylacylamides, aliphatic esters, aliphatic ketones, alicyclic ketones, aliphatic ethers, cyclic ethers, alkylnitriles and mixtures thereof. Most preferred are toluene, xylenes, petroleum ether, cyclohexane, dimethyl formamide, dimethylacetamide, ethylacetate, propyl acetat

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