GB923429A - Reactive polymeric monochlorotriazine dyes - Google Patents

Reactive polymeric monochlorotriazine dyes

Info

Publication number
GB923429A
GB923429A GB4312159A GB4312159A GB923429A GB 923429 A GB923429 A GB 923429A GB 4312159 A GB4312159 A GB 4312159A GB 4312159 A GB4312159 A GB 4312159A GB 923429 A GB923429 A GB 923429A
Authority
GB
United Kingdom
Prior art keywords
dyes
formula
chromophore
azo
compounds
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
GB4312159A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 claimed from US781488A external-priority patent/US3027362A/en
Priority claimed from US781474A external-priority patent/US3027361A/en
Priority claimed from US781480A external-priority patent/US3117957A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB923429A publication Critical patent/GB923429A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/0644—Poly(1,3,5)triazines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065—Preparatory processes
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)

Abstract

The invention comprises polymeric monochlorotriazine dyes of the formula ...-NH-D-NH-G-NH-D-NH-G-... where G is <FORM:0923429/IV(a)/1> and the D's are radicals of compounds having at least one chromophore and at least one sulphonic or carboxylic acid group per chromophore, the polymer chains being terminated by group of formula H2N-D, G-Cl or G-OH, D and G being as above, the dyes being characterized by their capacity to dye, from an alkaline aqueous bath, materials having OH, NH or NH2 groups by direct reaction therewith and having a higher percentage fixation on the fibre than is obtainable with analogous monomeric reactive dyes. The dyes may be made in aqueous solution by condensing compounds of formula H2N-D-NH2 with a substantially equimolecular proportion of cyanuric chloride or bromide in the presence of an acid-absorbing agent first at 0 DEG -5 DEG C. and then at 10 DEG -70 DEG C., or by a similar condensation at 10 DEG -70 DEG C. of a compound of formula H2N-D-NH-G-Cl. Polymeric azo dyes may be obtained by conventional processes using tetrazo components and coupling components which will couple twice either type of component containing the group G. Specified residues corresponding to D are derived from mono- and dis-azo, anthraquinone, dioxazine, phthalocyanine, safranine, triarylmethane and rhodamine dyes. The dyes are used to colour materials such as paper, cellulosic fibres, wool, silk, leather, nylon and polyvinyl alcohol film. Examples are provided of the preparation of the dyes and their use in colouring processes. Specification 775,308 is referred to. Reference has been directed by the Comptroller to Specification 797,946.ALSO:The invention comprises polymeric monochlorotriazine dyes of formula ,,,-NH-D-NH-G-NH-D-NH-G-,,, where G is <FORM:0923429/IV(a)/1> and the D's are radicals of compounds having at least one chromophore and at least one sulphonic or carboxylic acid group per chromophore, the polymer chain being terminated by groups of formula H2N-D, G-Cl or G-OH, D and G being as above, the dyes being characterized by their capacity to dye, from an aqueous alkaline bath, materials having OH, NH or NH2 groups by direct reaction therewith and having a higher fixation on the fibre than is obtainable with analogous monomeric reactive dyes. The dyes may be made, in aqueous solution, by condensing compounds of formula H2N-D-NH2 with a substantially equimolar proportion of cyanuric chloride or bromide in the presence of an acid-absorbing agent first at 0 DEG -5 DEG C., and then at 10 DEG -70 DEG C., or by a similar condensation at 10 DEG -70 DEG C. of a compound of formula H2N-D-NH-G-Cl. Polymeric azo dyes may be obtained by conventional processes using tetrazo components and coupling components which will couple twice either type of component containing the group G. Specified residues corresponding to D are derived from mono- and dis-azo, anthraquinone, dioxazine, phthalocyanine, safranine, triarylmethane and rhodamine dyes. The dyes are used to colour materials such as paper, cellulosic fibres, wool, silk, leather, nylon and polyvinyl alcohol film. Examples are provided of the preparation of the dyes and their use in colouring processes. Specification 775,308 is referred to. p Reference has been directed by the Comptroller to Specification 797,946.
GB4312159A 1958-12-19 1959-12-18 Reactive polymeric monochlorotriazine dyes Expired GB923429A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US78147058A 1958-12-19 1958-12-19
US781488A US3027362A (en) 1958-12-19 1958-12-19 Process of producing reactive polymeric azo dyes
US781474A US3027361A (en) 1958-12-19 1958-12-19 Fiber-reactive polymeric azo dyes
US781480A US3117957A (en) 1958-12-19 1958-12-19 Reactive polymeric dyes containing triazine

Publications (1)

Publication Number Publication Date
GB923429A true GB923429A (en) 1963-04-10

Family

ID=27505754

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4312159A Expired GB923429A (en) 1958-12-19 1959-12-18 Reactive polymeric monochlorotriazine dyes

Country Status (2)

Country Link
DE (1) DE1155203B (en)
GB (1) GB923429A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102741357A (en) * 2010-02-09 2012-10-17 荷兰联合利华有限公司 Dye polymers
CN103172858A (en) * 2013-04-24 2013-06-26 苏州益可泰电子材料有限公司 Preparation method of electronic material for transmitting high-frequency signals
CN103260344A (en) * 2013-04-24 2013-08-21 苏州益可泰电子材料有限公司 Signal transmission electronic circuit of non-linear editing system
WO2017158302A1 (en) 2016-03-16 2017-09-21 Arjo Wiggins Fine Papers Limited Method for producing paper impregnated by a supercritical-pressure fluid, and impregnated, particularly coloured paper

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9523575D0 (en) * 1995-11-17 1996-01-17 Zeneca Ltd Organic chemical compounds and processes

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102741357A (en) * 2010-02-09 2012-10-17 荷兰联合利华有限公司 Dye polymers
CN102741357B (en) * 2010-02-09 2014-05-28 荷兰联合利华有限公司 Dye polymers
CN103172858A (en) * 2013-04-24 2013-06-26 苏州益可泰电子材料有限公司 Preparation method of electronic material for transmitting high-frequency signals
CN103260344A (en) * 2013-04-24 2013-08-21 苏州益可泰电子材料有限公司 Signal transmission electronic circuit of non-linear editing system
CN103172858B (en) * 2013-04-24 2015-05-20 苏州益可泰电子材料有限公司 Preparation method of electronic material for transmitting high-frequency signals
CN103260344B (en) * 2013-04-24 2015-09-30 苏州益可泰电子材料有限公司 A kind of nonlinear editing system Signal transmissions electronic circuit
WO2017158302A1 (en) 2016-03-16 2017-09-21 Arjo Wiggins Fine Papers Limited Method for producing paper impregnated by a supercritical-pressure fluid, and impregnated, particularly coloured paper
US11091878B2 (en) 2016-03-16 2021-08-17 Arjo Wiggins Fine Papers Limited Method for producing paper impregnated by a supercritical-pressure fluid, and impregnated, particularly coloured paper

Also Published As

Publication number Publication date
DE1155203B (en) 1963-10-03

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