US5350634A
Expired / Lapsed
US
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Thermochromic composition
Assignee: Sakura Color Products Corp
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Filing: 1993-08-10
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Granted: 1994-09-27
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Expires: 2013-08-10
Abstract
Abstract A thermochromic composition which comprises (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, and (3) at least one desensitizer selected from among diphenylamine derivatives of-the following formulas: ##STR1## wherein R 1 and R 2 each independently is H, an alkyl group containing 1 to 22 carbon atoms, ##STR2## (in which R 3 and R 4 each independently is H, an alkyl group containing 1 to 4 carbon atoms). A thermochromic composition which comprises (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, (3) at least one desensitizer selected from among diphenylamine derivatives mentioned above, and (4) a thermochromic transition temperature modifier. A thermochromic composition which comprises one of the thermochromic compositions mentioned above as enclosed in microcapsule.
Inventors
- 👤 Masaaki Sumii
- 👤 Fumiko Sakai
- 👤 Yasuyuki Yoshimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 21:50
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/26; B41M5/28; B41M5/282; B41M5/284; Y; Y10; Y10T; Y10T428/00; Y10T428/29; Y10T428/2982; Y10T428/2984; Y10T428/2985
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
71 words
A thermochromic composition which comprises: (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, and (3) at least one desensitizer selected from among diphenylamine derivatives of the following formula: ##STR9## wherein R 1 and R 2 each independently is H, an alkyl group containing 1 to 22 carbon atoms, ##STR10## in which R 3 and R 4 each independently is H, an alkyl group containing 1 to 4 carbon atoms.
Claim 2
Dependent Claim
71 words
A thermochromic composition which comprises: (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, and (3) at least one desensitizer selected from among diphenylamine derivatives of the following formula: ##STR9## wherein R 1 and R 2 each independently is H, an alkyl group containing 1 to 22 carbon atoms, ##STR10## in which R 3 and R 4 each independently is H, an alkyl group containing 1 to 4 carbon atoms.
Claim 3
Dependent Claim
26 words
A thermochromic composition as claimed in claim 1, wherein said desensitizer is a diphenylamine derivative having a molecular weight within the range of 169 to 900.
Claim 4
Dependent Claim
28 words
A thermochromic composition as claimed in claim 1, wherein said desensitizer is a diphenylamine derivative having a melting point within the range of 50° C. to 300° C.
Claim 5
Dependent Claim
55 words
A thermochromic composition as claimed in claim 1, wherein said desensitizer comprises at least one diphenylamine derivative selected from the group consisting of diphenylamine, 4,4'-dimethyl diphenylamine, 4,4'-diethyl diphenylamine, 4,4'-dipropyl diphenylamine, 4,4'-dibutyl diphenylamine, 4,4'-diisopropyl diphenylamine, 4,4'-dicapryl diphenylamine, 4,4'-dilauryl diphenylamine, 4,4'-dimyristyl diphenylamine, 4,4'-dicetyl diphenylamine, 4,4'-distearyl diphenylamine, 4,4'-dioctyl diphenylamine, 4,4'-bis(α,α-dimethylbenzyl) diphenylamine, 4,4'-bis(α,α-diethylbenzyl) diphenylamine, 4,4'-bis(α,α-dipropylbenzyl) diphenylamine, and 4,4'-bis(α,α-diebutylbenzyl) diphenylamine.
Claim 6
Dependent Claim
35 words
A thermochromic composition as claimed in claim 1, wherein said electron-donating chromogenic organic compound comprises at least one compound selected from the group consisting of diarylphthalides, polyarylcarbinols, leucoauramines, rhodamine B lactams, indolines, spiropyrans, and fluorans.
Claim 7
Dependent Claim
67 words
A thermochromic composition as claimed in claim 1, wherein said electron-donating chromogenic organic compound comprises at least one compound selected from the group consisting of crystal violet lactone, malachite green lactone, 3-(4-diethylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl) phthalide, Michler's hydrol, crystal violet carbinol, malachite green carbinol, N-(2,3-dichlorophenyl) leucoauramine, N-benzoylauramine, N-acetylauramine, N-phenylauramine, rhodamine B lactam, 2-(phenyliminoethylidene) 3,3-dimethylindoline, N-3,3-trimethylindolinobenzospiropyran, 8-methoxy-N-3,3-trimethylindolinobenzospiropyran, 3-diethylamino-6-methyl-7-chlorofluoran, 3-diethylamino-7-methoxyfluoran, 3-diethylamino-6-benzyloxyfluoran, 3-amino-5-methylfluoran, 2-methyl-3-amino-6,7-dimethylfluoran, 2-bromo-6-cyclohexylaminofluoran, 2-(o-chlorophenylamino)-6-dibutylaminofluoran, 1,3-dimethyl-6-diethylaminofluoran, 3,6-diphenylaminofluoran, 9-(diethylamino)-spiro(12H-benzoxanthene-12,1'(3'H)-isobenzofluoran)-3'-one, 2-(N-phenyl-N-methylamino)-6-(N-ethyl-N-phenylamino)fluoran, 3-diethylamino-6-methyl-7-chlorofluoran, and 3-diethylaminobenzo(a)-fluoran.
Claim 8
Dependent Claim
62 words
A thermochromic composition as claimed in claim 1, wherein said electron-accepting compound comprises at least one compound selected from the group consisting of phenols, phenol resins, metal phenolates, aromatic carboxylic acids, aliphatic carboxylic acids containing 2 to 5 carbon atoms, metal salts of carboxylic acids, acid phosphoric esters, metal salts of acid phosphoric esters, triazole compounds, thiourea, diphenylthiourea, di-o-toluoylthiourea halohydrins, and benzothiazoles.
Claim 9
Dependent Claim
82 words
A thermochromic composition as claimed in claim 7, wherein said electron-accepting compound comprises at least one compound selected from the group consisting of bisphenol A, p-phenylphenol, dodecylphenol, o-bromophenol, ethyl p-hydroxybenzoate, methyl gallate, sodium phenolate, potassium phenolate, lithium phenolate, calcium phenolate, zinc phenolate, aluminum phenolate, magnesium phenolate, nickel phenolate, cobalt phenolate, tin phenolate, copper phenolate, iron phenolate, titanium phenolate, lead phenolate, molybdenum phenolate, phthalic acid, benzoic acid, acetic acid, propionic acid, sodium oleate, zinc salicylate, nickel benzoate, 1,2,3-triazole, 1,2,3-benzotriazole, thiourea, diphenylthiourea, and di-o-toluoylthiourea.
Claim 10
Dependent Claim
77 words
A thermochromic composition which comprises: (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, (3) at least one desensitizer selected from among diphenylamine derivatives of the following formula: ##STR11## wherein R 1 and R 2 each independently is H, an alkyl group containing 1 to 22 carbon atoms, ##STR12## in which R 3 and R 4 each independently is H, an alkyl group containing 1 to 4 carbon atoms, and (4) a thermochromic transition temperature modifier.
Claim 11
Dependent Claim
77 words
A thermochromic composition which comprises: (1) an electron-donating chromogenic organic compound, (2) an electron-accepting compound, (3) at least one desensitizer selected from among diphenylamine derivatives of the following formula: ##STR11## wherein R 1 and R 2 each independently is H, an alkyl group containing 1 to 22 carbon atoms, ##STR12## in which R 3 and R 4 each independently is H, an alkyl group containing 1 to 4 carbon atoms, and (4) a thermochromic transition temperature modifier.
Claim 12
Dependent Claim
26 words
A thermochromic composition as claimed in claim 9, wherein said desensitizer is a diphenylamine derivative having a molecular weight within the range of 169 to 900.
Claim 13
Dependent Claim
28 words
A thermochromic composition as claimed in claim 9, wherein said desensitizer is a diphenylamine derivative having a melting point within the range of -50° C. to 300° C.
Claim 14
Dependent Claim
55 words
A thermochromic composition as claimed in claim 9, wherein said desensitizer comprises at least one diphenylamine derivative selected from the group consisting of diphenylamine, 4,4'-dimethyl diphenylamine, 4,4'-diethyl diphenylamine, 4,4'-dipropyl diphenylamine, 4,4'-dibutyl diphenylamine, 4,4'-diisopropyl diphenylamine, 4,4'-dicapryl diphenylamine, 4,4'-dilauryl diphenylamine, 4,4'-dimyristyl diphenylamine, 4,4'-dicetyl diphenylamine, 4,4'-distearyl diphenylamine, 4,4'-dioctyl diphenylamine, 4,4'-bis(α,α-dimethylbenzyl) diphenylamine, 4,4'-bis(α,α-diethylbenzyl) diphenylamine, 4,4'-bis(α,α-dipropylbenzyl) diphenylamine and 4,4'-bis(α,α-diebutylbenzyl) diphenylamine.
Claim 15
Dependent Claim
47 words
A thermochromic composition as claimed in claim 9, wherein said thermochromic transition temperature modifier comprises at least one compound selected from the group consisting of alcohols, esters, ketones, ethers, acid amides, fatty acids, aromatic hydrocarbons, thiols, sulfides, disulfides, sulfoxides, sulfones, azomethines, and fatty acid primary amine salts.
Claim 16
Dependent Claim
115 words
A thermochromic composition as claimed in claim 9, wherein said thermochromic transition temperature modifier comprises at least one compound selected from the group consisting of n-cetyl alcohol, n-octyl alcohol, cyclohexanol, hexylene glycol, ethyl myristate, stearyl laurate, dioctyl phthalate, methyl hexyl ketone, benzophenone, stearone, butyl ether, diphenyl ether, distearyl ether, oleamide, stearamide, N-octyl lauramide, caproanilide, lauric acid, stearic acid, 2-hydroxymyristic acid, isopropylbenzene, dodecylbenzene, biphenyl, trimethylbiphenyl, diphenylethane, dibenzyltoluene, propylnaphthalene, butyltetralin, n-decylmercaptan, n-myristylmercaptan, n-stearylmercaptan, isocetylmercaptan, dodecylbenzylmercaptan, di-n-octyl sulfide, di-n-decyl sulfide, diphenyl sulfide, diethylphenyl sulfide, dilauryl thiodipropionate, di-n-octyl disulfide, di-n-decyl disulfide, diphenyl disulfide, dinaphthyl disulfide, diethyl sulfoxide, tetramethylene sulfoxide, diphenyl sulfoxide, diethyl sulfone, dibutyl sulfone, diphenyl sulfone, dibenzyl sulfone, benzylidenelaurylamine, p-methoxybenzylidenelaurylamine, benzylidene-p-anisidine, stearylamine oleate, myristylamine stearate, and stearylamine behenate.
Claim 17
Dependent Claim
35 words
A thermochromic composition as claimed in claim 9, wherein said electron-donating chromogenic organic compound comprises at least one compound selected from the group consisting of diarylphthalides, polyarylcarbinols, leucoauramines, rhodamine B lactams, indolines, spiropyrans, and fluorans.
Claim 18
Dependent Claim
65 words
A thermochromic composition as claimed in claim 9, wherein said electron-donating chromogenic organic compound comprises at least one compound selected from the group consisting of crystal violet lactone, malachite green lactone, 3-(4-diethylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl)phthalide, Michler's hydrol, crystal violet carbinol, malachite green carbinol, N-(2,3-dichlorophenyl)leucoauramine, N-benzoylauramine, acetylauramine, N-phenylauramine, rhodamine B lactam, 2-(phenyliminoethylidene) 3,3-dimethylindoline, N-3,3-trimethylindolinobenzospiropyran, 8-methoxy-N-3,3-trimethylindolinobenzospiropyran, 3-diethylamino-6-methyl-7-chlorofluoran, 3-diethylamino-7-methoxyfluoran, 3-diethylamino-6-benzyloxyfluoran, 3-amino-5-methylfluoran, 2-methyl-3-amino-6,7-dimethylfluoran, 2-bromo-6-cyclohexylaminofluoran, 2-(o-chlorophenylamino)-6-dibutylaminofluoran, 1,3-dimethyl-6-diethylaminofluoran, 3,6-diphenylaminofluoran, 9-(diethylamino)-spiro(12H-benzoxanthene-12,1'(3'H)-isobenzofluoran)-3'-one, 2-(N-phenyl-N-methylamino)-6-(N-ethyl-N-phenylamino)fluoran, 3-diethylamino-6-methyl-7-chlorofluoran, and 3-diethylaminobenzo(a)-fluoran.
Claim 19
Dependent Claim
62 words
A thermochromic composition as claimed in claim 9, wherein said electron-accepting compound comprises at least one compound selected from the group consisting of phenols, phenol resins, metal phenolates, aromatic carboxylic acids, aliphatic carboxylic acids containing 2 to 5 carbon atoms, metal salts of carboxylic acids, acid phosphoric esters, metal salts of acid phosphoric esters, triazole compounds, thiourea, diphenylthiourea, di-o-toluoylthiourea halohydrins, and benzothiazoles.
Claim 20
Dependent Claim
82 words
A thermochromic composition as claimed in claim 9, wherein said electron-accepting compound comprises at least one compound selected from the group consisting of bisphenol A, p-phenylphenol, dodecylphenol, o-bromophenol, ethyl p-hydroxybenzoate, methyl gallate, sodium phenolate, potassium phenolate, lithium phenolate, calcium phenolate, zinc phenolate, aluminum phenolate, magnesium phenolate, nickel phenolate, cobalt phenolate, tin phenolate, copper phenolate, iron phenolate, titanium phenolate, lead phenolate, molybdenum phenolate, phthalic acid, benzoic acid, acetic acid, propionic acid, sodium oleate, zinc salicylate, nickel benzoate, 1,2,3-triazole, 1,2,3-benzotriazole, thiourea, diphenylthiourea, and di-o-toluoylthiourea.
Claim 21
Dependent Claim
16 words
A microencapsulated thermochromic composition which comprises the thermochromic composition of claim 1 enclosed within a microcapsule.
References Cited (Backward Citations)
JPS61283589A
Cited
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