WO1996026074A1 - Mordants pour les feuilles receptrices de jets d'encre - Google Patents

Mordants pour les feuilles receptrices de jets d'encre Download PDF

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Publication number
WO1996026074A1
WO1996026074A1 PCT/US1996/000127 US9600127W WO9626074A1 WO 1996026074 A1 WO1996026074 A1 WO 1996026074A1 US 9600127 W US9600127 W US 9600127W WO 9626074 A1 WO9626074 A1 WO 9626074A1
Authority
WO
WIPO (PCT)
Prior art keywords
mordants
mordant
carbon atoms
ink
alkyl
Prior art date
Application number
PCT/US1996/000127
Other languages
English (en)
Inventor
Omar Farooq
Original Assignee
Minnesota Mining And Manufacturing Company
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 US08/548,580 external-priority patent/US5686602A/en
Application filed by Minnesota Mining And Manufacturing Company filed Critical Minnesota Mining And Manufacturing Company
Priority to EP96902085A priority Critical patent/EP0776272A1/fr
Publication of WO1996026074A1 publication Critical patent/WO1996026074A1/fr

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/42—Structural details
    • G03C8/52—Bases or auxiliary layers; Substances therefor
    • G03C8/56—Mordant layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5245—Macromolecular coatings characterised by the use of polymers containing cationic or anionic groups, e.g. mordants
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
    • C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/835—Macromolecular substances therefor, e.g. mordants

Definitions

  • This invention relates to mordants for ink-jet receptors and the like and more particularly, it relates to various types of novel mordants based upon a poly(alkylene oxide) backbone.
  • Mordants well-known in the photographic art, generally comprise materials containing quaternary ammonium groups as disclosed in U.S. Pat.
  • Quaternary phosphonium groups have also been incorporated with certain polymer backbones to obtain different classes of mordants such as those disclosed in U.S. Pat. Nos. 3,547,649; 4,820,608; and 4,855,211; and
  • the basic polymeric mordants useful to mordant a dye in a hydrophilic colloidal layer between a base and a photographic emulsion layer disclosed in
  • R is hydrogen or a methyl group
  • A is a -COO- or a -COO- alkylene group, e.g., -COOCH 2 -, -COOCH 2 CH 2 -, -COOCHOHCH 2 -
  • R 2 is a hydrogen or a lower alkyl group having from 1-4 carbon atoms
  • X ⁇ is an anion, e.g. , acetate, oxalate, sulfate, chloride, or bromide.
  • Mordant I can comprise units derived from vinylic monomers, for example, acrylates, acrylamides, vinyl acetates, styrenes, vinyl ethers, vinyl ketones, vinyl alcohols, unsaturated chlorides, and nitriles with the proviso that such copolymerizable units be in a quantity of 10-20% by weight. Similar mordants with the exclusion of A in I are also disclosed in GB Patent No. 850,281.
  • U.S. Pat. No. 5,354,813 discloses several classes of polymeric mordants having a pendent heterocyclic aromatic moiety, e.g. , a pyridyl or an imidazolyl group, as represented by the fomula U below:
  • X " represents an anion and n represents an integer of 2 or greater.
  • Mordants prepared by polymerizing or copolymerizing vinyl pyridine or N-alkyl pyridinium salts are also known in the art (see, for example, Italian Patent No. 931 ,270).
  • Non-diffusive mordants based on poly(N-vinylimidazole) of the type in are known in the art (see U.S. Patent No. 4,500,631) and have been used in certain radiographic image-forming processes wherein the mordants were coupled with water-soluble dyes. Mordants of the type in as well as IV are also disclosed in Japanese Publn. No. 63-307979.
  • mordants I, p-MePhSO 3
  • Other types of mordants for dyes are also known in the imaging arts.
  • U.S. Pat. No. 3,429,839 discloses mordants having pendant groups V, such as the mordant of formula VI :
  • R,, R 2 , and R 3 are alkyl, aryl, or aralkyl groups, or any two of R, , R 2 , or R 3 are part of a 5- or 6-membered heterocyclic ring and X " is an anion, usually an anion of a mineral acid or a carboxylic acid having from 2 to 20 carbon atoms.
  • R 1 , R , and R are alkyl, aryl, or aralkyl groups or any two of R] , R 2 , or R 3 are part of a 5- or 6-membered heterocyclic ring and X " is an anion.
  • R 1 is an alkyl group having 1 to 6 carbon atoms, preferably 1 to 2 carbon atoms and R 2 is an alkyl, aryl, aralkyl, or alkaryl group having up to 10 carbon atoms inclusive; preferably alkyl having up to 6 carbon atoms inclusive or phenyl; 1 and n are integers of 2 or greater, preferably 2-3, most preferably 3; m is an integer of 5 or greater, preferably 30-50, most preferably 40; and Q represents — (CH 2 ) y — wherein y is 1-20, preferably 3- 4.
  • X " is independently an anion, preferably CH 3 SO 3 _ , Br _ , NO 3 ⁇ , Cl ⁇ ,
  • alkyl group is intended to include not only pure open-chain and cyclic saturated hydrocarbon alkyl substituents, such as methyl, ethyl, propyl, t-butyl, cyclohexyl, adamantyl, octadecyl, and the like, but also alkyl substituents bearing further substituents known in the art, such as hydroxyl, alkoxy, vinyl, phenyl, halogen atoms (F, Cl, Br, and I), cyano, nitro, amino, carboxyl, etc.
  • alkyl moiety is limited to the inclusion of only pure open-chain and cyclic saturated hydrocarbon alkyl substituents, such as methyl, ethyl, propyl, t-butyl, cyclohexyl, adamantyl, octadecyl, and the like.
  • the Jeffamine primary amine mate ⁇ als used in the present invention are low average molecular weight materials and are commercially available from Texaco Chemical Co.
  • Two different types of Jeffamine materials are used in the present invention: Jeffamine ED-2001 [poly(propylene glycol-b- ethylene glycol-b-propylene glycol)bis(2-aminopropyl ether], weight average MW 2,000 (XIa. and Jeffamine” T-5000 [Glycerol tris(poly(propylene glycol), amine-terminated)ether], weight average MW 5,000, (Xlb).
  • Example 1 To a solution of 5g Jeffamine * ED-2001 (XIa) in 20g methanol was added a solution of the chloroacetone hydrazone (2.2 molar equiv.) of aminoguanidinium chloride in 10 mL methanol. The solution was heated to about 45°C for 10-15 minutes. Mordant Xlla (where X " and Y " are Cl-) was precipitated from ether as a semi-solid and dried in vacuum.
  • Example 1(a) The reaction in Example 1(a) was repeated using chloromethyl triphenylphosphonium bromide in place of the hydrazone to obtain the mordant X ⁇ I(b) wherein Q is -CH 2 - and Y " is Cl " .
  • Example 2 The reaction in Example 2(a) was repeated using bromopropyl triphenylphosphonium bromide in place of chloromethyl triphenylphosphonium bromide to obtain the mordant XIKb, where Q is - CH 2 CH 2 CH 2 - and Y " is Br " .
  • Example 3 To a solution of 5g of Jeffamine ® T-5000 (Xlb. in 20g methanol was added a solution of the chloroacetone hydrazone (3.3 molar equiv.) of aminoguanidinium chloride in 10 L methanol. The solution was heated to about 45-50 °C for 15 minutes to obtain the mordant XIII.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

On décrit de nouveaux mordants basés sur une ossature de poly(oxyde d'alkylène) et sur des groupes latéraux phosphonium ou à azote quaternaire. Ces mordants sont utiles pour arrêter ou pour diminuer le débordement de l'encre dans les feuilles réceptrices de jets d'encre et dans les films photographiques.
PCT/US1996/000127 1995-02-23 1996-01-05 Mordants pour les feuilles receptrices de jets d'encre WO1996026074A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP96902085A EP0776272A1 (fr) 1995-02-23 1996-01-05 Mordants pour les feuilles receptrices de jets d'encre

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US39320895A 1995-02-23 1995-02-23
US08/393,208 1995-02-23
US08/548,580 US5686602A (en) 1995-10-26 1995-10-26 Crosslinked cellulose polymer/colloidal sol matrix and its use with ink jet recording sheets
US08/548,580 1995-10-26

Publications (1)

Publication Number Publication Date
WO1996026074A1 true WO1996026074A1 (fr) 1996-08-29

Family

ID=27014204

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/000127 WO1996026074A1 (fr) 1995-02-23 1996-01-05 Mordants pour les feuilles receptrices de jets d'encre

Country Status (2)

Country Link
EP (1) EP0776272A1 (fr)
WO (1) WO1996026074A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6764725B2 (en) 2000-02-08 2004-07-20 3M Innovative Properties Company Ink fixing materials and methods of fixing ink
US6974609B2 (en) 2000-02-08 2005-12-13 Engle Lori P Media for cold image transfer

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4695531A (en) * 1985-07-25 1987-09-22 Minnesota Mining And Manufacturing Company Light-sensitive elements for radiographic use in the formation of an X-ray image
US4855211A (en) * 1987-09-11 1989-08-08 Agfa-Gevaert, N.V. Polymeric phosphonium mordant and photographic element containing the same
US5354813A (en) * 1993-03-12 1994-10-11 Minnesota Mining And Manufacturing Company Polymeric mordants for dyes and the like

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4695531A (en) * 1985-07-25 1987-09-22 Minnesota Mining And Manufacturing Company Light-sensitive elements for radiographic use in the formation of an X-ray image
US4855211A (en) * 1987-09-11 1989-08-08 Agfa-Gevaert, N.V. Polymeric phosphonium mordant and photographic element containing the same
US5354813A (en) * 1993-03-12 1994-10-11 Minnesota Mining And Manufacturing Company Polymeric mordants for dyes and the like

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6764725B2 (en) 2000-02-08 2004-07-20 3M Innovative Properties Company Ink fixing materials and methods of fixing ink
US6974609B2 (en) 2000-02-08 2005-12-13 Engle Lori P Media for cold image transfer
US7005162B2 (en) 2000-02-08 2006-02-28 3M Innovative Properties Company Methods of fixing ink

Also Published As

Publication number Publication date
EP0776272A1 (fr) 1997-06-04

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