GB630359A - Improvements relating to the manufacture of organic pigments and moulding powders - Google Patents

Improvements relating to the manufacture of organic pigments and moulding powders

Info

Publication number
GB630359A
GB630359A GB27008/47A GB2700847A GB630359A GB 630359 A GB630359 A GB 630359A GB 27008/47 A GB27008/47 A GB 27008/47A GB 2700847 A GB2700847 A GB 2700847A GB 630359 A GB630359 A GB 630359A
Authority
GB
United Kingdom
Prior art keywords
diazotized
aniline
hydroxy
nitro
naphthoic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB27008/47A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Calico Printers Association Ltd
Original Assignee
Calico Printers Association Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL68682D priority Critical patent/NL68682C/xx
Priority to NL67432D priority patent/NL67432C/xx
Priority to BE481887D priority patent/BE481887A/xx
Priority claimed from GB9208/44A external-priority patent/GB582019A/en
Priority to GB10253/47A priority patent/GB624491A/en
Priority to GB27008/47A priority patent/GB630359A/en
Application filed by Calico Printers Association Ltd filed Critical Calico Printers Association Ltd
Priority to US18083A priority patent/US2534136A/en
Priority to CH278187D priority patent/CH278187A/en
Priority to FR59528D priority patent/FR59528E/en
Priority to CH271033D priority patent/CH271033A/en
Publication of GB630359A publication Critical patent/GB630359A/en
Priority to DEC2593A priority patent/DE949309C/en
Priority to DEC2707A priority patent/DE947337C/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B39/00—Other azo dyes prepared by diazotising and coupling
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0061—Preparation of organic pigments by grinding a dyed resin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye

Abstract

Pigments and moulding powders are made by treating a finely-divided polyvinyl benzal prepared as in the parent Specification with an alkali salt of a coupling component, washing, and thereafter treating with a diazonium salt derived from an aromatic base having no water-solubilizing substituent. Any coupling component possessing the group <FORM:0630359/IV (a)/1> and devoid of water-solubilizing substituents may be used, particularly the Naphthols AS. The polyvinyl benzal is preferably one prepared from an aromatic aldehyde of the benzene or naphthalene series and polyvinyl alcohol in which the molecular ratio of aldehyde to alcohol is between 0.1 : 1.0 and 0.8 : 1.0. The polyvinyl alcohol used may contain ester or aliphatic acetal groups provided that it is still water-soluble, and the aromatic aldehyde may contain substituents such as chloro- and nitro groups. In a modification, the diazonium salt is converted to an isodiazotate and applied to the polyvinyl benzal simultaneously with the coupling component and the dyestuff developed by subsequent acidification. In examples, partial polyvinyl benzal in finely-divided form is treated with: (1) 2-naphthol, caustic soda and sodium ricinoleate and then with diazotized 4-nitro-2-methoxy-aniline; (2) 2-hydroxy-3-naphthoic acid anilide, caustic soda and sodium sulphoricinoleate and then with diazotized 4-chloro-2-methyl-aniline or diazotized 2-chloro-5 - trifluoromethyl - aniline; (3) 2 - hydroxy - 3-naphthoic acid anilide as in (2) and then with 4-nitro-2-methyl-aniline; (4) the sodium salt of 2-hydroxy-3-naphthoic acid p-anisidide and then with diazotized 4-nitro-2-methoxy-aniline; (5) the sodium salt of 2-hydroxy-3-naphthoic acid o-toluidide and then with diazotized 2,5-diethoxy-4-benzoylamino-aniline or 2-methoxy-5 - methyl - 4 - benzoylamino - aniline; (6) the sodium salt of 2-hydroxy-3-naphthoic acid anilide and then with diazotized 3,31-dimethyl-4,41-diamino-diphenyl or 4-(41-nitrobenzene-azo)-2,5-dimethoxy-aniline; (7) diacetoacetic acid-o-toluidide and then with diazotized 2-methoxy-aniline; (8) a mixture of 2-hydroxy-3-naphthoic acid anilide and the sodium derivative of 2,5-dichlorobenzene diazonium hydroxide and then developed with formic acid; (9) 2,2 - dihydroxy - 5,51 - dimethyl - diphenyl - methane and then with diazotized 2,51-dichloroaniline; (10) 2-hydroxycarbazole-3-carboxylic acid-p-chloroanilide and then with diazotized 4 - nitro - 2,2 - methoxy - aniline; and (11) 2 - hydroxy -3-naphthoic acid-p-aniside and then with diazotized 5-nitro-2-amino-toluene.ALSO:Pigments are made by treating a finely-divided polyvinyl benzal prepared as in the parent Specification with an alkali salt of a coupling component, washing, and thereafter treating with a diazonium salt derived from an aromatic base having no water-solubilizing substituent. Any coupling component possessing the group <FORM:0630359/IV (c)/1> and devoid of water-solubilizing substituents may be used, particularly the Naphthols AS. The polyvinyl benzal is preferably one prepared from an aromatic aldehyde of the benzene or naphthalene series and polyvinyl alcohol in which the molecular ratio of aldehyde to alcohol is between 0.1 : 1.0 and 0.8 : 1.0. The polyvinyl alcohol used may contain ester or aliphatic acetal groups provided that it is still water-soluble, and the aromatic aldehyde may contain substituents such as chloro- and nitro-groups. In a modification, the diazonium salt is converted to an isodiazotate and applied to the polyvinyl benzal simultaneously with the coupling component and the dyestuff developed by subsequent acidification. In examples, partial polyvinyl benzal in finely divided form is treated with (1) 2-naphthol, caustic soda and sodium ricinoleate and then with diazotized 4 - nitro - 2 - methoxy - aniline; (2) 2 - hydroxy 3-naphthoic acid anilide, caustic soda and sodium sulphoricinoleate and then with diazotized 4 - chloro - 2 - methyl - aniline or diazotized 2 - chloro - 5 - trifluoromethyl - aniline; (3) 2-hydroxy-3-naphthoic acid anilide as in (2) and then with 4-nitro-methyl-aniline; (4) the sodium salt of 2-hydroxy-3-naphthoic acid p-anisidide and then with diazotized 4-nitro-2-methoxy-aniline; (5) the sodium salt of 2-hydroxy-3-naphthoic acid o-toluidide and then with diazotized 2,5-diethoxy-4-benzoylamino - aniline or 2 - methoxy - 5 - methyl - 4-benzoylaminoaniline; (6) the sodium salt of 2-hydroxy-3-naphthoic acid anilide and then with diazotized 3,31-dimethyl-4,41-diamino-diphenyl or 4 - (41 - nitrobenzeneazo) - 2,5-dimethoxy-aniline; (7) diacetoacetic acid-o-tolidide and then with diazotized 2-methoxyaniline; (8) a mixture of 2-hydroxy-3-naphthoic acid anilide and the sodium derivative of 2,5-dichlorobenzene diazonium hydroxide and then developed with formic acid; (9) 2,21-dihydroxy-5,51-dimethyl-diphenyl-methane and then with diazotized 2,51 - dichloroaniline; (10) 2-hydroxycarbazole - 3 - carboxylic acid - p-chloroanilide and then with diazotized 4-nitro-2-methoxy - aniline, and (11) 2 - hydroxy - 3-naphthoic acid-p-anisidide and then with diazotized 5-nitro-2-amino-toluene.
GB27008/47A 1944-05-13 1947-10-08 Improvements relating to the manufacture of organic pigments and moulding powders Expired GB630359A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL68682D NL68682C (en) 1947-04-17
NL67432D NL67432C (en) 1947-04-17
BE481887D BE481887A (en) 1947-04-17
GB10253/47A GB624491A (en) 1944-05-13 1947-04-17 Improvements relating to the manufacture of organic pigments and moulding powders
GB27008/47A GB630359A (en) 1944-05-13 1947-10-08 Improvements relating to the manufacture of organic pigments and moulding powders
US18083A US2534136A (en) 1947-04-17 1948-03-30 Pigments and molding powders comprising polyvinyl acetal resins dyed with vat dyes
CH278187D CH278187A (en) 1944-05-13 1948-04-16 Process for preparing a colored organic polymer.
FR59528D FR59528E (en) 1944-05-13 1948-10-05 New organic compounds for use as pigments and molding products and their manufacturing process
CH271033D CH271033A (en) 1944-05-13 1948-10-06 Process for preparing a colored organic polymer, usable as pigment and molding powder.
DEC2593A DE949309C (en) 1947-04-17 1950-09-28 Process for the production of colored polyvinyl resin powder
DEC2707A DE947337C (en) 1947-04-17 1950-09-29 Process for the production of colored polyvinyl resin powder

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9208/44A GB582019A (en) 1944-05-13 1944-05-13 Improvements relating to the manufacture of organic pigments and moulding powders
GB1202445 1945-05-14
GB10253/47A GB624491A (en) 1944-05-13 1947-04-17 Improvements relating to the manufacture of organic pigments and moulding powders
GB27008/47A GB630359A (en) 1944-05-13 1947-10-08 Improvements relating to the manufacture of organic pigments and moulding powders

Publications (1)

Publication Number Publication Date
GB630359A true GB630359A (en) 1949-10-11

Family

ID=37103149

Family Applications (2)

Application Number Title Priority Date Filing Date
GB10253/47A Expired GB624491A (en) 1944-05-13 1947-04-17 Improvements relating to the manufacture of organic pigments and moulding powders
GB27008/47A Expired GB630359A (en) 1944-05-13 1947-10-08 Improvements relating to the manufacture of organic pigments and moulding powders

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB10253/47A Expired GB624491A (en) 1944-05-13 1947-04-17 Improvements relating to the manufacture of organic pigments and moulding powders

Country Status (2)

Country Link
CH (2) CH278187A (en)
GB (2) GB624491A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921592C (en) * 1951-07-20 1954-12-23 Hoechst Ag Process for coloring polyvinyl compounds

Also Published As

Publication number Publication date
CH271033A (en) 1950-09-30
CH278187A (en) 1951-09-30
GB624491A (en) 1949-06-09

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