Granted Patent B2

US 8,916,497 · App. 14/264,516 · Granted Dec 23, 2014

Abstract

Claims (37)

1. A thermally-responsive record material, substantially free of aromatic isocyanate, the record material comprising a support having provided thereon a heat-sensitive composition comprising:

a substantially colorless dye precursor;

a developer material selected from the group consisting of 4,4′-diaminodiphenylsulfone and 3,3′-diaminodiphenylsulfone;

in combination with N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide;

which upon being heated react with said dye precursor to develop color;

and a binder material.

2. The thermally-responsive record material according to claim 1 , wherein the substantially colorless dye precursor comprises a fluoran compound of the formula

wherein R 1 is hydrogen or alkyl

wherein R 2 is hydrogen or alkaryl;

wherein R 3 is aryl when R 2 is hydrogen, or alkaryl when R 2 is alkaryl;

R 4 and R 5 are each independently selected from alkyl, aralkyl; or R 4 and R 5 form a four carbon ring pyrrolidine structure.

3. The thermally-responsive record material according to claim 2 wherein the fluoran is selected from the group consisting of:

4. The thermally-responsive record material according to claim 1 wherein the heat sensitive composition is applied onto the support at from 0.5 to 8 gsm.

5. The thermally-responsive record material according to claim 1 wherein the amount of the N-[(butylamino)carbonyl]-4-metaylbenzenesulfoinamide is from 10% to 90% by weight of the combined weight of the sulfonamide and the developer material.

6. The thermally-responsive record material according to claim 1 having an ANSI grade of B or better.

7. The thermally-responsive record material according to claim 1 wherein the record material includes in addition a polymeric top coat.

8. The thermally-responsive record material according to claim 1 wherein the substantially colorless dye precursor selected from the group consisting of:

2-chloro-6-(diethylamino)-fluoran; 6-(diethylamino)-3-oxo-spiro[isobenzofuran-1(3H), 9′-[9H]xanthene]-2′-carboxylic acid ethyl ester; 3-(diethylamino)-7-(dibenzylamino)fluoran; 7-[4-(diethylamino)-2-ethoxyphenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl)furo[3,4-b]pyridin-5(7H)-one; 4,5,6,7-tetrachloro-3,3-bis[2-[4-dimethylamino]phenyl]-2-(4-methoxyphenyl)ethenyl]-1(3H)isobenzofuranone; and crystal violet lactone.

9. The thermally response record material according to claim 1 wherein the ratio by weight of developer and sulfonamide together to dye precursor is from 0.5:1 to 5:1.

10. The thermally responsive record material according to claim 1 comprising in addition a polymeric top coat over the heat sensitive composition.

11. The improved bar code according to claim 10 having an ANSI grading of C or better.

12. The improved bar code according to claim 10 wherein the developer is selected from 4,4′-diaminodiphenylsulfone and 3,3′-diaminodiphenylsulfone, and the dye precursor is selected from group consisting of:

3-diethylamino-6-methyl1-7-(2′,4′dimethyl aniline) fluoran,

3-dibutylamino-6-methyl-7-anilino fluoran,

3-diethylamino-6-methyl-7-(3′-methylanilino) fluoran,

3-diethylamino-6-methyl-7-anilinofluoran,

3-pyrrolidino-6-methyl-7-anilino fluoran,

3-diethylamino-7-(dibenzylamino) fluoran,

2-chloro-6-(diethylamino)-fluoran,

6-(diethylamino)-3-oxo-spiro[isobenzofuran-1(3H), 9′-[9H]xanthene]-2′-carboxylic acid ethyl ester,

3-(diethylamino)-7-(dibenzylamino)fluoran,

7-[4-(diethylamino)-2-ethoxyphenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl) furo[3,4-b]pyridin-5(7H)-one, and

4,5,6,7-tetrachloro-3,3-bis[2-[4-dimethylamino]phenyl]-2-(4-methoxyphenyl)ethenyl]-1(3H)isobenzofuranone;

and crystal violet lactone.

13. The thermally responsive record material according to claim 1 comprising in addition an insulating layer positioned between the heat sensitive composition and the support.

14. The thermally responsive record material according to claim 1 wherein the support comprises paper or film.

15. An improved bar code comprising a thermally responsive record material according to claim 1 .

Assignments (21)