# US 5,346,878 A · Recording material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,346,878 A - Document ID: US5346878A - Status: Granted - Kind: A - Application number: 08/108,500 - Filed: 1993-08-18 - Granted: 1994-09-13 - Earliest claimed: 1991-09-24 - Assignees: Mitsui Toatsu Chemicals, Inc.; Mitsubishi Paper Mills Limited - Inventors: Masakatsu Nakatsuka; Naomasa Koike; Akinori Okada - Web page: https://patentgrep.com/patent/US5346878A ## CPC - C07C 333/24: having nitrogen atoms of dithiocarbamate groups bound to carbon atoms of six-membered aromatic rings - B41M 5/3335: {Compounds containing phenolic or carboxylic acid groups or metal salts thereof} - B41M 5/3375: {Non-macromolecular compounds} - C07C 271/28: to a carbon atom of a non-condensed six-membered aromatic ring - C07C 271/58: with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring - C07C 333/08: having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings - B41M 5/3336: {Sulfur compounds, e.g. sulfones, sulfides, sulfonamides} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P) ## Abstract The heat-sensitive recording material disclosed comprises a colorless or pale colored dyestuff precursor, one or more salicylic acid derivative of the formula (1) or metal salt of the derivative and an aliphatic amide compound having 18.about.60 carbon atoms in molecular structure, and is excellent in thermal response and preservation stability of white portions and images. ##STR1## wherein X.sub.1 and X.sub.2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y.sub.1 and Y.sub.2 are an oxygen atom or a sulfur atom, R.sub.1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R.sub.2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group. ## Claims ### Claim 1 A heat-sensitive recording material comprising a substrate having at least one layer thereon comprising: a colorless or pale colored dyestuff precursor; an electron accepting compound which develops the color of said dyestuff precursor by heat-reaction, wherein said electron accepting compound is one or more compounds selected from a salicylic acid derivative represented by the formula ( 1 ) ##STR7## wherein X.sub.1 and X.sub.2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y.sub.1 and Y.sub.2 are an oxygen atom or a sulfur atom, R.sub.1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R.sub.2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group, or a metal salt of said salicylic acid derivative, and an aliphatic amide compound having 18.about.60 carbon atoms. ### Claim 2 (depends on 1) The heat-sensitive recording material of claim 1 wherein the salicylic acid derivative represented by the formula (1) or the metal salt of said salicylic acid derivative is a salicylic acid derivative of the formula (2-c): ##STR8## wherein X.sub.1 and X.sub.2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, and R is an alkyl group, alkenyl group, an aralkyl group or an aryl group, or a metal salt of the salicylic acid derivative. ### Claim 3 (depends on 2) The heat-sensitive recording material of claim 2 wherein the aliphatic amide compound is represented by the formula (3): R.sub.3 CONH.sub.2 ( 3) wherein R.sub.3 is an alkyl group or an alkenyl group and has 17.about.59 carbon atoms. ### Claim 4 (depends on 2) The heat-sensitive recording material of claim 2 wherein the aliphatic amide compound is represented by the formula (4): R.sub.4 CONHR.sub.5 ( 4) wherein R.sub.4 is an alkyl group or an alkenyl group, R.sub.5 is an alkyl group, an alkenyl group or a hydroxymethyl group, and the sum of carbon atoms in R.sub.4 and R.sub.5 is 17.about.59. ### Claim 5 (depends on 2) The heat-sensitive recording material of claim 2 wherein the aliphatic amide compound is represented by the formula (5): R.sub.6 CONHR.sub.7 NHOCR.sub.6 ( 5) wherein R.sub.6 is an alkyl group or an alkenyl group, R.sub.7 is a divalent aliphatic group, and the sum of carbon atoms in R.sub.6 and R.sub.7 is 16.about.58. ### Claim 6 (depends on 2) The heat-sensitive recording material of claim 2 wherein the aliphatic amide compound is represented by the formula (6): R.sub.8 NHOCR.sub.9 CONHR.sub.8 ( 6) wherein R.sub.8 is an alkyl group or an alkenyl group, R.sub.9 is a divalent aliphatic group, and the sum of carbon atoms in R.sub.8 and R.sub.9 is 16.about.58. ### Claim 7 (depends on 2) The heat-sensitive recording material of claim 2 wherein the metal salt of the salicylic acid derivative represented by the formula (1-c) is a zinc salt. ### Claim 8 (depends on 2) The heat-sensitive recording material of claim 2 wherein the amount of the aliphatic amide compound is 10.about.300% based on the salicylic acid derivative or the metal salt of said derivative. ### Claim 9 (depends on 2) The heat-sensitive recording material of claim 2, wherein the electron accepting compound comprises one or more divalent, trivalent or tetravalent metal salts of said salicylic acid derivative of formula (2-c). ### Claim 10 (depends on 2) The heat-sensitive recording material of claim 2, wherein the X.sub.1 and X.sub.2 in the salicylic acid derivative of formula (2-c) or metal salt of said salicylic acid derivative are hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.14 alicyclic group, C.sub.1 -C.sub.20 alkoxy, C.sub.7 -C.sub.20 aralkyl, phenyl, fluorine, chlorine or bromine. ### Claim 11 (depends on 2) The heat-sensitive recording material of claim 2, wherein the electron accepting compound comprises one or more metal salts of said salicylic acid derivative of formula (2-c) selected from the group consisting of sodium, potassium, lithium, zinc, cadmium, mercury, magnesium, calcium, barium, nickel, tin, gallium, chromium, copper, molybdenum, wolfram, zirconium, strontium, manganese, cobalt, titanium, aluminum and iron salts. ### Claim 12 (depends on 1) The heat-sensitive recording material of claim 1 wherein the aliphatic amide compound is represented by the formula (3): R.sub.3 CONH.sub.2 ( 3) wherein R.sub.3 is an alkyl group or an alkenyl group and has 17.about.59 carbon atoms. ### Claim 13 (depends on 1) The heat-sensitive recording material of claim 1 wherein the aliphatic amide compound is represented by the formula (4): R.sub.4 CONHR.sub.5 ( 4) wherein R.sub.4 is an alkyl group or an alkenyl group, R.sub.6 is an alkyl group, an alkenyl group or a hydroxymethyl group, and the sum of carbon atoms in R.sub.4 and R.sub.6 is 17.about.59. ### Claim 14 (depends on 1) The heat-sensitive recording material of claim 1 wherein the aliphatic amide compound is represented by the formula (5): R.sub.6 CONHR.sub.7 NHOCR.sub.6 ( 5) wherein R.sub.6 is an alkyl group or an alkenyl group, R.sub.7 is a divalent aliphatic group, and the sum of carbon atoms in R.sub.6 and R.sub.7 is 16.about.58. ### Claim 15 (depends on 1) The heat-sensitive recording material of claim 1 wherein the aliphatic amide compound is represented by the formula (6): R.sub.8 NHOCR.sub.9 CONHR.sub.8 ( 6) wherein R.sub.8 is an alkyl group or an alkenyl group, R.sub.9 is a divalent aliphatic group, and the sum of carbon atoms in R.sub.8 and R.sub.9 is 16.about.58. ### Claim 16 (depends on 1) The heat-sensitive recording material of claim 1 wherein the metal salt of the salicylic acid derivative represented by the formula (1) is a zinc salt. ### Claim 17 (depends on 1) The heat-sensitive recording material of claim 1 wherein the amount of the aliphatic amide compound is 10.about.300% by weight based on the salicylic acid derivative or the metal salt of said derivative. ### Claim 18 (depends on 1) The heat-sensitive recording material of claim 1, wherein the electron accepting compound comprises one or more divalent, trivalent or tetravalent metal salts of said salicylic acid derivative of formula (1). ### Claim 19 (depends on 1) The heat-sensitive recording material of claim 1, wherein the X.sub.1 and X.sub.2 in the salicylic acid derivative of formula (1) or metal salt of said salicylic acid derivative are hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.14 alicyclic group, C.sub.1 -C.sub.20 alkoxy, C.sub.7 -C.sub.20 aralkyl, phenyl, fluorine, chlorine or bromine. ### Claim 20 (depends on 1) The heat-sensitive recording material of claim 1, wherein the electron accepting compound comprises one or more metal salts of said salicylic acid derivative of formula (1) selected from the group consisting of sodium, potassium, lithium, zinc, cadmium, mercury, magnesium, calcium, barium, nickel, tin, gallium, chromium, copper, molybdenum, wolfram, zirconium, strontium, manganese, cobalt, titanium, aluminum and iron salts.