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US3963429A Expired / Lapsed US ⏱️ 0.0 years remaining

Coloring of organic materials with asymmetric thioindigoid compounds

Assignee: Mitsui Toatsu Chemicals Inc
•
Filing: 1974-01-09
•
Granted: 1976-06-15
•
Expires: 1994-01-09
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Abstract

Abstract Method of coloring a synthetic or semisynthetic organic high molecular weight material with a asymmetric thioindigoid compound having the formula WHEREIN R1, R2 and R3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, benzyl group and styryl group, the benzene nucleus of the phenyl and benzyl group may be optionally substituted with a methyl group or chlorine atom, R1 and R2 may together form a tetramethylene ring, R4 is a hydrogen atom or methyl group with the proviso that R4 is a methyl group when R1, R2 and R3 are each a hydrogen atom and R4 is a hydrogen atom when R1 is a methyl group and R2 and R3 are each a hydrogen atom. The colored organic high molecular weight materials exhibit brilliant nuance with characteristic fluorescence.

Inventors

  • 👤 Michihiro Tsujimoto
  • 👤 Kisuke Osawa
  • 👤 Ichiro Okubo

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 09:31
CPC Classifications
C; C09; C09B; C09B23/00; C09B23/14; C08; C08K; C08K5/00; C08K5/36; C08K5/45; C09B7/00; C09B7/10; D; D06; D06P; D06P1/00; D06P1/0004; D06P1/0012; D06P1/16; D06P1/22; D06P1/228; Y; Y10; Y10S; Y10S8/00; Y10S8/92; Y10S8/922

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 235 words
In a method of coloring synthetic or semisynthetic organic high molecular weight material in brilliant nuance with characteristic fluorescence by (A) fixation of the coloring material on the synthetic or semisynthetic high molecular weight organic material by (i) heating the organic material in an aqueous dispersion of the coloring material; (ii) printing the coloring material onto the organic material; or (iii) impregnating the organic material with an aqueous dispersion of the coloring material; or (B) admixing the coloring material with the molten synthetic or semisynthetic high molecular weight organic material, the improvement comprising using as said coloring material an asymmetric thioindigoid compound having the formula: ##SPC5## wherein R 1 , R 2 and R 3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group, R 1 and R 2 may together form a tetramethylene ring, R 4 is a member selected from the group consisting of a hydrogen atom and methyl group with the proviso that R 4 is a methyl group when R 1 , R 2 , and R 3 are each a hydrogen atom and R 4 is a hydrogen atom when R 1 is a methyl group and R 2 and R 3 are each a hydrogen atom.
Claim 2
Dependent Claim 235 words
In a method of coloring synthetic or semisynthetic organic high molecular weight material in brilliant nuance with characteristic fluorescence by (A) fixation of the coloring material on the synthetic or semisynthetic high molecular weight organic material by (i) heating the organic material in an aqueous dispersion of the coloring material; (ii) printing the coloring material onto the organic material; or (iii) impregnating the organic material with an aqueous dispersion of the coloring material; or (B) admixing the coloring material with the molten synthetic or semisynthetic high molecular weight organic material, the improvement comprising using as said coloring material an asymmetric thioindigoid compound having the formula: ##SPC5## wherein R 1 , R 2 and R 3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group, R 1 and R 2 may together form a tetramethylene ring, R 4 is a member selected from the group consisting of a hydrogen atom and methyl group with the proviso that R 4 is a methyl group when R 1 , R 2 , and R 3 are each a hydrogen atom and R 4 is a hydrogen atom when R 1 is a methyl group and R 2 and R 3 are each a hydrogen atom.
Claim 3
Dependent Claim 57 words
The method as claimed in claim 1, wherein R 2 , R 3 and R 4 are each a hydrogen atom and R 1 is a member selected from the group consisting of a lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group.
Claim 4
Dependent Claim 47 words
The method as claimed in claim 2, wherein R 1 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group, ethoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group and chlorobenzyl group.
Claim 5
Dependent Claim 16 words
The method as claimed in claim 3, wherein the asymmetric thioindigoid compound has the formula: ##SPC6##
Claim 6
Dependent Claim 16 words
The method as claimed in claim 3, wherein the asymmetric thioindigoid compound has the formula: ##SPC7##
Claim 7
Dependent Claim 16 words
The method as claimed in claim 3, wherein the asymmetric thioindigoid compound has the formula: ##SPC8##
Claim 8
Dependent Claim 83 words
The method as claimed in claim 1, wherein R 3 and R 4 are each a hydrogen atom, R 1 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group, ethoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group and chlorobenzyl group and R 2 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group and ethoxy group.
Claim 9
Dependent Claim 16 words
The method as claimed in claim 7, wherein the asymmetric thioindigoid compound has the formula: ##SPC9##
Claim 10
Dependent Claim 16 words
The method as claimed in claim 7, wherein the asymmetric thioindigoid compound has the formula: ##SPC10##
Claim 11
Dependent Claim 29 words
The method as claimed in claim 1, wherein R 3 and R 4 are each a hydrogen atom and R 1 and R 2 together form a tetramethylene ring.
Claim 12
Dependent Claim 31 words
The method as claimed in claim 1, wherein R 4 is a hydrogen atom, R 1 is a methoxy group and R 2 and R 3 are each a methyl group.
Claim 13
Dependent Claim 12 words
The method of claim 1 wherein said organic material is a polyester.
Claim 14
Dependent Claim 163 words
A synthetic or semisynthetic organic high molecular weight material having brilliant nuance and characteristic fluorescence comprising a synthetic or semisynthetic high molecular weight organic material colored with an asymmetric thioindigoid dyestuff having the formula ##SPC11## wherein R 1 , R 2 and R 3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group, R 1 and R 2 may together form a tetramethylene ring, R 4 is a member selected from the group consisting of a hydrogen atom and methyl group with the proviso that R 4 is a methyl group when R 1 , R 2 and R 3 are each a hydrogen atom and R 4 is a hydrogen atom when R 1 is a methyl group and R 2 and R 3 are each a hydrogen atom.
Claim 15
Dependent Claim 163 words
A synthetic or semisynthetic organic high molecular weight material having brilliant nuance and characteristic fluorescence comprising a synthetic or semisynthetic high molecular weight organic material colored with an asymmetric thioindigoid dyestuff having the formula ##SPC11## wherein R 1 , R 2 and R 3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group, R 1 and R 2 may together form a tetramethylene ring, R 4 is a member selected from the group consisting of a hydrogen atom and methyl group with the proviso that R 4 is a methyl group when R 1 , R 2 and R 3 are each a hydrogen atom and R 4 is a hydrogen atom when R 1 is a methyl group and R 2 and R 3 are each a hydrogen atom.
Claim 16
Dependent Claim 57 words
The colored organic material of claim 13 wherein R 2 , R 3 and R 4 are each a hydrogen atom and R 1 is a member selected from the group consisting of a lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group, chlorobenzyl group and styryl group.
Claim 17
Dependent Claim 47 words
The colored organic material of claim 14 wherein R 1 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group, ethoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group and chlorobenzyl group.
Claim 18
Dependent Claim 16 words
The colored organic material of claim 15 wherein the asymmetric thioindigoid compound has the formula: ##SPC12##
Claim 19
Dependent Claim 16 words
The colored organic material of claim 15 wherein the asymmetric thioindigoid compound has the formula: ##SPC13##
Claim 20
Dependent Claim 16 words
The colored organic material of claim 15 wherein the asymmetric thioindigoid compound has the formula: ##SPC14##
Claim 21
Dependent Claim 83 words
The colored organic material of claim 13 wherein R 3 and R 4 are each a hydrogen atom, R 1 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group, ethoxy group, cyclohexyl group, phenyl group, tolyl group, chlorophenyl group, benzyl group, methylbenzyl group and chlorobenzyl group and R 2 is a member selected from the group consisting of a methyl group, ethyl group, isopropyl group, tert.-butyl group, methoxy group and ethoxy group.
Claim 22
Dependent Claim 16 words
The colored organic material of claim 19 wherein the asymmetric thioindigoid compound has the formula: ##SPC15##
Claim 23
Dependent Claim 16 words
The colored organic material of claim 19, wherein the asymmetric thioindigoid compound has the formula: ##SPC16##
Claim 24
Dependent Claim 29 words
The colored organic material of claim 13, wherein R 3 and R 4 are each a hydrogen atom and R 1 and R 2 together form a tetramethylene ring.
Claim 25
Dependent Claim 31 words
The colored organic material of claim 13 wherein R 4 is a hydrogen atom, R 1 is a methoxy group and R 2 and R 3 are each a methyl group.
Claim 26
Dependent Claim 14 words
The colored organic material of claim 13 wherein said organic material is a polyester.

References Cited (Backward Citations)

US2096140A Cited
US2882277A Cited
US3793341A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-15 1979-12-15 1980-06-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-15 1983-12-15 1984-06-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-15 1987-12-15 1988-06-15 $7700.00 Window Closed / Lapsed

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