WO1996001866A1 - Polyamides et encres ou vernis derives - Google Patents

Polyamides et encres ou vernis derives Download PDF

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Publication number
WO1996001866A1
WO1996001866A1 PCT/EP1995/002414 EP9502414W WO9601866A1 WO 1996001866 A1 WO1996001866 A1 WO 1996001866A1 EP 9502414 W EP9502414 W EP 9502414W WO 9601866 A1 WO9601866 A1 WO 9601866A1
Authority
WO
WIPO (PCT)
Prior art keywords
diamine
polyamide
ink
acid
inks
Prior art date
Application number
PCT/EP1995/002414
Other languages
English (en)
Inventor
Margaret Mills
Garth Bryan Simpson
Original Assignee
Cray Valley Limited
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
Application filed by Cray Valley Limited filed Critical Cray Valley Limited
Publication of WO1996001866A1 publication Critical patent/WO1996001866A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
    • C09D101/08—Cellulose derivatives
    • C09D101/16—Esters of inorganic acids
    • C09D101/18—Cellulose nitrate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D177/06—Polyamides derived from polyamines and polycarboxylic acids
    • C09D177/08—Polyamides derived from polyamines and polycarboxylic acids from polyamines and polymerised unsaturated fatty acids

Definitions

  • This invention is concerned with improvements in and relating to polyamides and, more particularly, is concerned with polyamides suitable for use as resinous vehicles in printing inks, especially flexographic printing inks containing such polyamides.
  • Thermoplastic polyamides derived, inter alia, from so-called “dimer acids” have been used as components of printing inks for some years.
  • polyamides may be used as components of flexographic inks and may be formulated to meet the requirements of such inks, namely good adhesion to a wide variety of substrates, rapid drying, the use of solvents which will not attack rubber stereos, low print odour and good resistance properties.
  • the polyamides may be used alone in flexographic inks or in combination with other resinous materials, especially nitrocellulose.
  • thermoplastic polyamides of the sort described above may be used in flexographic inks used in the packaging industry, for printing on polyethylene and other extruded film. In this application, the polyamide may be used to impart good adhesion and flexibility in combination with nitrocellulose which will impart good gloss and hardness to the final ink.
  • Polyamide resins are also used in gravure inks for printing treated polyolefin, nylon and polyesters films. Their main advantages are that they show excellent pigment wetting properties, high gloss, excellent water and deep freeze resistance. The suitability of resins for use in overprint varnishes (high gloss lacquers on various packaging designs) largely depends on the skill of the formulator. All these resins make extremely good starting point materials due to their high gloss, toughness and flexibility, combined with good grease and water resistance.
  • GB-A- 1.055.676 discloses a polyamide, suitable as an adhesive, being a condensation product of a polymeric fatty acid having a dimeric fatty acid content of at least 90%, and a diamine mixture comprising a major molar amount of ethyl ene diamine and a minor molar amount of an aliphatic diamine such as 2,2,4- trimethylhexamethylene diamine.
  • GB-A- 1.052.575 discloses a reaction product, useful in the formulation of printing inks, of 1,2-propane diamine (and possibly ethylene diamine), a polymeric fatty acid and an acid selected from acetic, lactic, glycolic and formic acid.
  • a polybasic acid component comprising a polymeric fatty acid, and optionally, one or more other polybasic acids which may be aliphatic or aromatic in character
  • polyamino component comprising a mixture of at least a straight-chain lower diamine and at least a branched chain diamine, and (iii) at least a monocarboxylic acid.
  • the polybasic acid component (i) preferably comprises only the polymeric fatty acid.
  • polymeric fatty acid as used herein, is intended to refer to the product of the polymerisation of ethylenically unsaturated monocarboxylic acids containing from about 8 to about 22 carbon atoms. These products may be obtained by the process described in US-A-3157681 and may be produced by a catalytic or non-catalytic polymerisation process.
  • unsaturated aliphatic monocarboxylic acids containing from 16 to 18 carbon atoms are preferred as starting materials and the most preferred starting materials are unsaturated aliphatic monocarboxylic acids containing 18 carbon atoms such as linoleic and oleic acids.
  • the resulting mixture contains predominantly dimeric fat acids, some trimeric and higher polymeric fat acids and some unpolymerised monomeric fat acids.
  • polymer acids typically contain from about 5 to about 15% by weight of monocarboxylic acids, from about 60 to about 80% by weight of dicarboxylic acids and from about 10 to about 35% by weight of higher carboxylic acids.
  • dimer acid polymeric fatty acids
  • these mixtures may be fractionated by high vacuum distillation or solvent extraction to obtain dimer acid cuts of higher concentration if desired.
  • the diamino component (ii) preferably consists of diprimary diamines and, especially, of a mixture of at least a straight chain lower diamine selected from ethylene diamine and 1 ,3-propane diamine together with at least a long chain (i.e. C 6 -C 12 ) branched chain diamine.
  • the lower straight chain diamine suitably forms from about 5 to about 95 mole % of the diamino component, preferably from about 50 to about 70% thereof, the branched chain diamine forming the balance.
  • the third component (iii) from which the polyamide is formed is, as noted above, a monocarboxylic acid, especially an aliphatic monocarboxylic acid containing from 2 to about 18 carbon atoms, most preferably from 2 to 4 carbon atoms such as acetic, propionic and isobutyric acids. It acts, of course, as a chain stopper and the amount thereof relative to the dimer acid will effectively control the molecular weight of the final polyamide.
  • the monomeric fatty acids suitably provides from about 10 to about 70 mole % of the total carboxyl functionality of the mixture, preferably from about 45 to about 65 mole % thereof. In general, it is preferred to use acid and amine components in substantially stoichiometric amounts.
  • the polyamides of the invention are produced in a conventional manner, i.e. by polycondensing the acid and amine components at elevated temperature, e.g. from about 80 to about 230°C, whilst distilling off water evolved during the condensation reaction. Reaction is suitably carried out until the reaction mixture has a maximum amine value of about 4 mgKOH/g and a maximum acid value of about 4 mgKOH/g.
  • the resultant polyamides may be used in printing inks, especially flexographic inks to give products having good adhesion, scratch resistance, water resistance and deep freeze resistance whilst, at the same time, having improved solution properties as indicated by a lower gel temperature and a lower gel recovery temperature.
  • an ink or varnish comprising a polyamide as defined above dissolved in a solvent (typically an alcoholic solvent or an ester solvent such as an acetate) and also containing in the case of an ink, a colorant such as a pigment or dyestuff.
  • a solvent typically an alcoholic solvent or an ester solvent such as an acetate
  • a colorant such as a pigment or dyestuff.
  • an ink or varnish may also contain other resinous material especially nitrocellulose and, in this latter instance, the weight proportion of polyamide to nitrocellulose is suitably from about 0.1 : 1 to about 20: 1.
  • Polyamides were prepared, following the process described above, from the components listed in Table 1 hereinafter.
  • Example 1 Example 2 Example 3 Example 4 Example 5 Example 6
  • Typical formulations for inks containing the above polyamides are as follows : a) White Flexographic ink

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Polyamides (AREA)

Abstract

L'invention concerne un polyamide thermoplastique obtenu par polycondensation de (i) un composant d'acide polybasique comprenant un acide gras polymère éventuellement avec un ou plusieurs autres acides polybasiques, (ii) un composé polyamino comprenant un mélange d'au moins une diamine inférieure à chaîne droite et d'au moins une diamine à chaîne ramifiée; et (iii) au moins un acide monocarboxylique. L'invention concerne également l'utilisation de cette formulation pour des encres et des vernis.
PCT/EP1995/002414 1994-07-11 1995-06-21 Polyamides et encres ou vernis derives WO1996001866A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9413926A GB2291064A (en) 1994-07-11 1994-07-11 Polyamides
GB9413926.8 1994-07-11

Publications (1)

Publication Number Publication Date
WO1996001866A1 true WO1996001866A1 (fr) 1996-01-25

Family

ID=10758124

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002414 WO1996001866A1 (fr) 1994-07-11 1995-06-21 Polyamides et encres ou vernis derives

Country Status (2)

Country Link
GB (1) GB2291064A (fr)
WO (1) WO1996001866A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023933A1 (fr) * 2010-08-18 2012-02-23 Sun Chemical Corporation Encre pour impression rapide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5658968A (en) * 1996-12-09 1997-08-19 Sun Chemical Corporation Flexible packaging printing ink

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1052575A (fr) * 1964-05-14
FR1578455A (fr) * 1967-08-21 1969-08-14
DE1645407A1 (de) * 1964-10-15 1970-09-24 Schering Ag Verfahren zur Herstellung von Polyamiden
JPS56166276A (en) * 1980-05-27 1981-12-21 Kao Corp Printing ink
DE3243794A1 (de) * 1982-11-26 1984-05-30 Schering AG, 1000 Berlin und 4709 Bergkamen Alkoholloesliche druckfarben
GB2177411A (en) * 1985-06-28 1987-01-21 Labofina Sa Thixotropic agents, thixotropic paint compositions containing them, and process for preparing the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1520933B2 (de) * 1964-05-23 1974-05-09 Schering Ag Verfahren zur Herstellung von Copolyamiden und deren Verwendung als Schmelzkleber
US4661194A (en) * 1985-11-19 1987-04-28 Henkel Corporation Fabric bonding polyamide resins with lowered fusion point

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1052575A (fr) * 1964-05-14
DE1645407A1 (de) * 1964-10-15 1970-09-24 Schering Ag Verfahren zur Herstellung von Polyamiden
FR1578455A (fr) * 1967-08-21 1969-08-14
JPS56166276A (en) * 1980-05-27 1981-12-21 Kao Corp Printing ink
DE3243794A1 (de) * 1982-11-26 1984-05-30 Schering AG, 1000 Berlin und 4709 Bergkamen Alkoholloesliche druckfarben
GB2177411A (en) * 1985-06-28 1987-01-21 Labofina Sa Thixotropic agents, thixotropic paint compositions containing them, and process for preparing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 006, no. 054 (C - 097) 9 April 1982 (1982-04-09) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023933A1 (fr) * 2010-08-18 2012-02-23 Sun Chemical Corporation Encre pour impression rapide
US9016202B2 (en) 2010-08-18 2015-04-28 Sun Chemical Corporation High speed printing ink

Also Published As

Publication number Publication date
GB2291064A (en) 1996-01-17
GB9413926D0 (en) 1994-08-31

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