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US5234887A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermal transfer printing

Assignee: Illinois Tool Works Inc
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Filing: 1988-11-15
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Granted: 1993-08-10
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Expires: 2008-11-15
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Abstract

Abstract A thermal transfer printing sheet comprising a substrate having a coating comprising a dye of the formula: A-N=N-E wherein A is a phenyl group substituted by at least one electron-withdrawing group selected from NO2, CN, CF3, halogen, -SO2-C1-4-alkyl, -SO2F, -SO2CF3, -SO2NRR1, -CONRR1, -COOR, -CO-CO-R, wherein R and R1 are independently selected from H and C1-4 alkyl, provided that where A carries only two halogen atoms these are not in the 2- and 6- positions in relation to the azo link; and E is the radical of an aniline, a tetrahydroquinoline, a lilolidine or a julolidine coupling component, and a thermal transfer printing process for the coloration of a polymeric substrate using the thermal transfer printing sheet.

Inventors

  • 👤 Peter Gregory
  • 👤 Raymond White
  • 👤 Geoffrey Rothwell
  • 👤 Roy Porter

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 18:20
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/26; B41M5/382; B41M5/385; B41M5/388; Y; Y10; Y10S; Y10S428/00; Y10S428/913; Y10S428/914; Y10T; Y10T428/00; Y10T428/26; Y10T428/263; Y10T428/264; Y10T428/265

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 288 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometers carrying a coating comprising a dye of the formula: ##STR13## wherein A is a phenyl group substituted by two or three electron withdrawing groups selected from NO 2 , CN and --SO 2 --C 1-4 -alkyl and optionally by one or more groups selected from C 1-4 -alkyl and C 1-4 -alkoxy; and E is selected from (i) an anilino group of the formula: ##STR14## wherein R 2 is selected from H, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylthio, NH 2 --CO--NH, NCONH--, phenyl-CONH--, C 1-4 -alkyl--CO--NH, C 1-4 -alkyl--SO 2 --NH--, CN, CF 3 , and halogen; R 3 and R 4 are independently selected from H; C 1-6 -alkyl and C 4-8 -cycloalkyl, each of which is unsubstituted or substituted by a group independently selected from halogen, CN, phenyl, mono- or bicyclic heteroaryl, --OCO--C 1-4 -alkyl, --COO--C 1-4 -alkyl, C 2-4 -alkenyl, and C 1-4 -alkoxy; or R 3 and R 4 together with the nitrogen atom to which they are attached form a heterocyclic ring, selected from morpholine, piperazine and thiomorpholine; and R 5 is selected from H, C 1-4 -alkyl and C 1-4 -alkoxy; (ii) a tetrahydroquinolinyl group of the formula: ##STR15## wherein R 3 is selected from H; C 1-6 -alkyl, C 4-8 -cycloalkyl, each of which is independently unsubstituted or substituted by a group selected from halogen, CN, phenyl, mono- or bicyclic heteroaryl, --OCO--C 1-4 -alkyl, --COO--C 1-4 -alkyl, C 2-4 -alkenyl, C 1-4 -alkoxy; and R 6 to R 9 are independently selected from H and C 1-6 -alkyl; and (iii) lilolidinyl or julolidinyl of the formula: ##STR16## wherein n=2 (lilolidine) or 3 (julolidine).
Claim 2
Dependent Claim 288 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometers carrying a coating comprising a dye of the formula: ##STR13## wherein A is a phenyl group substituted by two or three electron withdrawing groups selected from NO 2 , CN and --SO 2 --C 1-4 -alkyl and optionally by one or more groups selected from C 1-4 -alkyl and C 1-4 -alkoxy; and E is selected from (i) an anilino group of the formula: ##STR14## wherein R 2 is selected from H, C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylthio, NH 2 --CO--NH, NCONH--, phenyl-CONH--, C 1-4 -alkyl--CO--NH, C 1-4 -alkyl--SO 2 --NH--, CN, CF 3 , and halogen; R 3 and R 4 are independently selected from H; C 1-6 -alkyl and C 4-8 -cycloalkyl, each of which is unsubstituted or substituted by a group independently selected from halogen, CN, phenyl, mono- or bicyclic heteroaryl, --OCO--C 1-4 -alkyl, --COO--C 1-4 -alkyl, C 2-4 -alkenyl, and C 1-4 -alkoxy; or R 3 and R 4 together with the nitrogen atom to which they are attached form a heterocyclic ring, selected from morpholine, piperazine and thiomorpholine; and R 5 is selected from H, C 1-4 -alkyl and C 1-4 -alkoxy; (ii) a tetrahydroquinolinyl group of the formula: ##STR15## wherein R 3 is selected from H; C 1-6 -alkyl, C 4-8 -cycloalkyl, each of which is independently unsubstituted or substituted by a group selected from halogen, CN, phenyl, mono- or bicyclic heteroaryl, --OCO--C 1-4 -alkyl, --COO--C 1-4 -alkyl, C 2-4 -alkenyl, C 1-4 -alkoxy; and R 6 to R 9 are independently selected from H and C 1-6 -alkyl; and (iii) lilolidinyl or julolidinyl of the formula: ##STR16## wherein n=2 (lilolidine) or 3 (julolidine).
Claim 3
Dependent Claim 44 words
A thermal transfer printing sheet according to claim 1 wherein A is of the formula: ##STR17## wherein X 1 is NO 2 , CN or --SO 2 Ch 3 ; and X 2 is NO 2 , CN or --SO 2 CH 3 .
Claim 4
Dependent Claim 29 words
A thermal transfer printing sheet according to claim 1 where A is of the formula ##STR18## wherein X' is NO 2 , CN or SO 2 ,CH 3 .
Claim 5
Dependent Claim 40 words
A thermal transfer printing sheet according to claim 1 wherein A is of the formula: ##STR19## wherein Y 1 and Y 2 are independently selected from CN and NO 2 , provided that they are not both NO 2 .
Claim 6
Dependent Claim 69 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR20## wherein X 1 is NO 2 or CN; R 12 is selected from H, CH 3 and --NHCOCH 3 ; and R 14 and R 15 are each independently selected from C 2-4 -alkyl, C 1-4 -alkylene--OCO--C 1-4 -alkyland C 2 H 4 CN.
Claim 7
Dependent Claim 69 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR20## wherein X 1 is NO 2 or CN; R 12 is selected from H, CH 3 and --NHCOCH 3 ; and R 14 and R 15 are each independently selected from C 2-4 -alkyl, C 1-4 -alkylene--OCO--C 1-4 -alkyland C 2 H 4 CN.
Claim 8
Dependent Claim 82 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR21## wherein Y 1 is NO 2 or CN; Y 2 is CN; R 14 and R 15 are each independently selected from C 2-4 -alkyl and C 1-4 -alkylene--OCO--C 1-4 -alkyl; R 5 is selected from H, C 1-4 -alkyl and C 1-4 -alkoxy; and R 12 is selected from H, CH 3 or --NHCOCH 3 .
Claim 9
Dependent Claim 82 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR21## wherein Y 1 is NO 2 or CN; Y 2 is CN; R 14 and R 15 are each independently selected from C 2-4 -alkyl and C 1-4 -alkylene--OCO--C 1-4 -alkyl; R 5 is selected from H, C 1-4 -alkyl and C 1-4 -alkoxy; and R 12 is selected from H, CH 3 or --NHCOCH 3 .
Claim 10
Dependent Claim 84 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR22## wherein Z is H or --OCOCH 3 ; in admixture with a dye of the formula: ##STR23## wherein R is H or --OCH 3 ; Q is selected from H, --OCOCH 3 and --COOC 2 H 4 OCH 3 ; and Q 1 is selected from H, --Ch 2 H 5 and --C 2 H 4 OCOCH 3 .
Claim 11
Dependent Claim 84 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR22## wherein Z is H or --OCOCH 3 ; in admixture with a dye of the formula: ##STR23## wherein R is H or --OCH 3 ; Q is selected from H, --OCOCH 3 and --COOC 2 H 4 OCH 3 ; and Q 1 is selected from H, --Ch 2 H 5 and --C 2 H 4 OCOCH 3 .
Claim 12
Dependent Claim 130 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR24## wherein X 1 is NO 2 or CN; R 12 is selected from H, CH 3 and --NHCOCH 3 ; and R 14 and R 15 are each independently selected from C 2-4 -alkyl, C 1-4 -alkylene--OCO--C 1-4 -alkyl and C 2 H 4 CN; in admixture with a dye of the formula: ##STR25## wherein A 1 is selected from 3-methyl-4-cyanoisothiazol-5-yl, 4-cyano-isothiazol-5-yal and 1-cyanomethyl-3,4-dicyanopyrazol-5-yl; and E is of the formula: ##STR26## wherein R 2 is selected from H, chlorine and C 1-4 -alkyl; R 3 and R 4 are each independently C 2-4 -alkylene-OCO--C 1-4 -alkyl or C 2-4 -alkyl; and R 5 is H.
Claim 13
Dependent Claim 130 words
A thermal transfer printing sheet comprising a substrate having a thickness less than 10 micrometres carrying a coating including a dye of the formula: ##STR24## wherein X 1 is NO 2 or CN; R 12 is selected from H, CH 3 and --NHCOCH 3 ; and R 14 and R 15 are each independently selected from C 2-4 -alkyl, C 1-4 -alkylene--OCO--C 1-4 -alkyl and C 2 H 4 CN; in admixture with a dye of the formula: ##STR25## wherein A 1 is selected from 3-methyl-4-cyanoisothiazol-5-yl, 4-cyano-isothiazol-5-yal and 1-cyanomethyl-3,4-dicyanopyrazol-5-yl; and E is of the formula: ##STR26## wherein R 2 is selected from H, chlorine and C 1-4 -alkyl; R 3 and R 4 are each independently C 2-4 -alkylene-OCO--C 1-4 -alkyl or C 2-4 -alkyl; and R 5 is H.
Claim 14
Dependent Claim 79 words
A thermal transfer printing process which comprises contacting a thermal transfer printing sheet according to any one of claims 1-8 with a receiver sheet, so that the dye is adjacent to the receiver sheet, and selectively heating an area of the transfer sheet to a temperature from 250° C. to 400° C. for a period of from 0.5 to 30 msec whereby dye in the heated area of the transfer sheet may be selectively transferred to the receiver sheet.

References Cited (Backward Citations)

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EP0066278A1 Cited
JPS5978896A Cited
JPS6031565A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-08-09 1997-02-08 1997-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-08-09 2001-02-08 2001-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-08-09 2005-02-08 2005-08-10 $7700.00 Window Closed / Lapsed

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