Thermal Recording Color Developer Plasticizer Resistance

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Solution Overview

Problem

Existing non-phenolic color developers, such as N-(phenylureidophenyl)benzenesulfonamide and phenylureidophenyl-benzenesulfonate compounds, exhibit low plasticizer resistance, leading to potential fading of printed parts when exposed to plasticizers.

Innovation Solution

A color developer combination comprising a compound of formula (I), either an N-(phenylureidophenyl)benzenesulfonamide or a phenylureidophenyl-benzenesulfonate, and an N-substituted amino acid derivative of formula (II), such as N-(m-tolylaminocarbonyl)-phenylalanine or N-(phenylaminocarbonyl)-phenylalanine, is used to enhance plasticizer resistance in thermal recording materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If non-phenolic color developers (N-(phenylureidophenyl)benzenesulfonamide or phenylureidophenyl-benzenesulfonate compounds) are used, then endocrine disruption concerns are reduced, but plasticizer resistance deteriorates

Engineering Contradiction:
Improveendocrine disruption riskVSAvoidplasticizer resistance
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The invention uses a composite color developer system combining a phenylureidophenyl compound (formula I) with an N-substituted amino acid derivative (formula II). This composite approach allows the first compound to provide good printing properties and the second compound to enhance plasticizer resistance, resolving the contradiction between endocrine safety and plasticizer resistance.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention modifies the chemical structure by introducing specific substituents (R1-R6 groups) at defined positions on the phenyl rings and by selecting specific amino acid derivatives. These parameter changes in molecular structure optimize both the safety profile and the plasticizer resistance of the color developer system.

Inventive Principle:
Principle #35Parameter changes

2Manufacturing precision

If N-(phenylureidophenyl)benzenesulfonamide or phenylureidophenyl-benzenesulfonate compounds are used as color developers, then printing properties are improved, but plasticizer resistance deteriorates

Engineering Contradiction:
Improveprinting propertiesVSAvoidplasticizer resistance
Core Design Contradiction:
Manufacturing precisionVSReliability

Solution Approach 1:

The patent combines two different color developer compounds with complementary properties. The phenylureidophenyl compound (formula I) provides excellent printing properties, while the N-substituted amino acid derivative (formula II) provides enhanced plasticizer resistance. Together they form a composite system that achieves both goals simultaneously.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The color developer function is segmented into two separate compounds, each optimized for a specific function. Formula I is optimized for printing properties while formula II is optimized for plasticizer resistance, and their effects are combined in the thermal recording material.

Inventive Principle:
Principle #1Segmentation

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The proposed solution significantly improves the plasticizer resistance of thermal recording materials without compromising other essential properties like color development density, whiteness, and storage stability, making them suitable for various applications including POS register paper and food labels.

Implementation Method 1

a color developer for developing color upon contact with the basic dye by heating

Methodology Applied
Scientific EffectThermal decomposition: Pyrolysis

Data Source

PatentEP4269119B1Colour developer, thermal recording material, and coating material for thermal recording layers
Publication Date: 2025.05.07 SANKO CO LTD
  • EP4269119B1 patent drawing
  • EP4269119B1 patent drawing
  • EP4269119B1 patent drawing

AI summary

The present invention provides a color developer which is excellent in plasticizer resistance. A color developer for a thermal recording layer of the present invention, includes: a compound of formula (I); and an N-substituted amino acid derivative of formula (II), wherein in the formula (I), L represents an imino group (-NH-) or an oxy group (-O-); R1, R2 and R3 each represent a hydrogen atom, a halogen atom, a nitro group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an alkenyl group, a fluoroalkyl group, an N(R4)2 group (wherein R4 represents a hydrogen atom, a phenyl group, a benzyl group, or an alkyl group having 1 to 6 carbon atoms), an NHCOR5 group (wherein R5 represents an alkyl group having 1 to 6 carbon atoms), an optionally substituted phenyl group, an optionally substituted benzyl group, an aryloxy group, an alkylcarbonyloxy group, an arylcarbonyloxy group, an alkylcarbonylamino group, an arylcarbonylamino group, an alkylsulfonylamino group, or an arylsulfonylamino group; n1, n2 and n3 each independently represent an integer of 0 to 5; R1, R2 and R3 are identical to or different from one another; when two or more R1s are present, R1s are identical to or different from each other; when two or more R2s are present, R2s are identical to or different from each other; and when two or more R3s are present, R3s are identical to or different from each other,         (R0-X)-Y-(Z)     (II) wherein in the formula (II), R0 represents an alkyl group having an aryl group having 6 to 10 carbon atoms or an aryl group optionally substituted with a substituent of an alkyl group having 1 to 8 carbon atoms, an aralkyl group having 7 to 11 carbon atoms, an aryl group having 6 to 10 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms; X represents a group bonded to an N-terminal of Y and represents -OCO-, -SO2NHCO-, - NHCO-, -NHCS-, or -SO2-; Y represents an amino acid residue or a peptide residue, and an OH group of a serine residue, a threonine residue, an aspartic acid residue, a glutamic acid residue, or a tyrosine residue in the Y group is optionally substituted with an OR0 group or an OR" group, and an SH group of a cysteine residue is optionally substituted with an SR0 group or an SR" group, an NH group of a histidine residue is optionally substituted with an NR0 group or an NR' group, an NH2 group of a lysine residue or an ornithine residue is optionally substituted with an NHR0 group or an NHR' group, R' represents an amino protecting group, and R" represents a carboxy protecting group, provided that Y is an amino acid residue other than a cystine residue or a peptide residue having no cystine residue; Z is a group bonded to a C-terminal of Y and represents an OH group or an OR" group; R0, R' and R" are identical to or different from one another; when two or more R0s are present, R0s are identical to or different from each other; when two or more R's are present, R's are identical to or different from each other; when two or more R"s are present, R"s are identical to or different from each other; and two or more groups of R0, R', and R" are optionally bonded to each other to form a ring.