EP0444065A1 - Produits de condensation a base de colophane-maleinimides - Google Patents

Produits de condensation a base de colophane-maleinimides

Info

Publication number
EP0444065A1
EP0444065A1 EP19890912450 EP89912450A EP0444065A1 EP 0444065 A1 EP0444065 A1 EP 0444065A1 EP 19890912450 EP19890912450 EP 19890912450 EP 89912450 A EP89912450 A EP 89912450A EP 0444065 A1 EP0444065 A1 EP 0444065A1
Authority
EP
European Patent Office
Prior art keywords
condensation products
rosin
groups
reaction
molar ratio
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.)
Withdrawn
Application number
EP19890912450
Other languages
German (de)
English (en)
Inventor
Bernhard Prantl
Erich Frank
Walter Koch
Gerd LÖBBERT
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.)
BASF Farben und Fasern AG
Original Assignee
BASF Lacke und Farben AG
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 BASF Lacke und Farben AG filed Critical BASF Lacke und Farben AG
Publication of EP0444065A1 publication Critical patent/EP0444065A1/fr
Withdrawn legal-status Critical Current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
    • 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
    • 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
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
    • C09F1/04—Chemical modification, e.g. esterification

Definitions

  • the present invention relates to condensation products based on rosin-maleimides, obtainable by reacting an excess of rosin with maleic anhydride, subsequent condensation with organic diprimeric diamines and esterification with P. polyalcohols of functionality 3 to 6, a process and its preparation and the use in printing inks .
  • resins for offset printing inks consist largely of rosin-modified phenolic resins that are esterified with polyalcohols.
  • J-61264-014A From J-61264-014A, JA-7111 354 and US-A 4 643 848 are condensation products of rosin, maleic anhydride and
  • Phenolic resins known that are recommended as binders for printing inks are recommended as binders for printing inks.
  • a disadvantage of these resins is that they do not dry quickly enough (become tack-free) and in some cases have a low gloss.
  • the object of the present invention was to develop condensation products which are soluble in non-polar solvents and with which printing inks can be produced which have good printability, rapid drying and thus rapid freedom from tack, high gloss and low odor nuisance.
  • the task was solved by rosin-maleimides which are esterified in a mixture with rosin with alcohols having a functionality of 3 to 6.
  • the present invention relates to condensation products based on rosin-maleimides, obtainable from
  • the invention also relates to the production of these condensation products and their use in printing inks.
  • reaction of rosin with maleic anhydride of stage A is known and is carried out at a temperature of 150 to 250 ° C., preferably 180 to 230 ° C.
  • a molar excess of rosin * is used, 1 to 20 parts by weight, preferably 5 to 12 parts by weight, of maleic anhydride being used per 100 parts by weight of rosin.
  • the rosin-maleic anhydride adduct in a mixture with rosin is condensed in stage B with an organic diamine at temperatures from 130 to 35 250 ° C., preferably 140 to 200 ° C.
  • a molar ratio of anhydride groups to amino groups of 0.8 to 1.2: 1, preferably 0.9 to 1.1: 1 is set. This produces a bis-rosin-maleimide in excess rosin.
  • Step B can also be prepared by reacting a rosin-maleic acid adduct with an organic diprimary diamine in the molar ratio indicated above and dissolving it in a corresponding excess of melted rosin, or by Maleic anhydride is condensed with an organic diprimary diamine in the above molar ratio to a bismaleimide, which is reacted with a more than double molar excess of rosin or is reacted with the approximately double molar amount of rosin and the rosin-maleimide formed in this way is melted in excess Rosin is dissolved, however, the first method described is preferred.
  • Suitable organic diprimary diamines are aliphatic diamines such as ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, neopentanediamine, 1,4-butanediamine, hexamethylenediamine, 9-aminomethylstearylamine, cycloaliphatic diamines such as cyclohexanediamine-1,6 , 4'-diamino-dicyclohexyl ethane, 3, 3'-dimethyl-4, 4'diaminodicyclohexylmethane, ether diamines such as 4, 7-dioxadodecane-l, 10-diamine, 4, 9-dioxadodecane-l, 12-diamine , 4, 7, 10-trioxatridecane-1, 13-diamine, diaminoamines such as bis-aminopropylmethylamine or 1, 4 ⁇ bis (3-aminoprop l)
  • oligomeric or polymeric polyamines with an average molecular weight M n of up to 3000 can also be used.
  • examples of such polyamines are diamines which can be prepared by reductive cyanoethylation of polyols, such as polytetrahydrofuran. Products of this type contain terminal primary amino groups in the form of aminopropoxy groups.
  • diamines with additional amide groups can be used according to the invention by condensation of primary aliphatic or cycloaliphatic diamines with dicarboxylic acids such as adipic acid, sebacic acid or dimeric fatty acid.
  • dicarboxylic acids such as adipic acid, sebacic acid or dimeric fatty acid.
  • the amines described above can be used alone or in a mixture with one another.
  • Hexamethylenediamine, 4,4'-diamino-dicyclohexylmethane, 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane and reaction products of dicarboxylic acids with diamines are preferably used.
  • stage C the further condensation takes place with a polyalcohol of functionality 3 to 6, at temperatures from 230 to 300 ° C., preferably 250 to 280 ° C., optionally in the presence of conventional esterification catalysts, with a molar ratio of carboxyl groups of the reaction mixture B. ) to hydroxyl groups of the polyalcohol from 0.7 to 1.5: 1, preferably 0.8 to 1.1: 1.
  • Suitable polyalcohols are aliphatic polyalcohols with a functionality of 3 to 6 such as trimethylolpropane, glycerol, pentaerythritol, dipentaerythritol or sorbitol or aminoalcohols such as triethanolamine or triisopropanolamine or reaction products of these polyalcohols with ethylene oxide and / or propylene oxide or mixtures of these polyalcohols. Trimethylolpropane, glycerol, pentaerythritol or mixtures thereof are preferably used.
  • the resulting resins are solid products at room temperature with melting points that are between about 80 and 160 ° C, depending on the resin structure.
  • the resins dissolve in mineral oil, which may contain other non-polar solvents, to give clear mineral oil varnishes.
  • mineral oil which may contain other non-polar solvents, to give clear mineral oil varnishes.
  • these varnishes can be used to formulate printing inks which are stable in storage, ie which do not show an increase in viscosity with storage times of a few months, can be easily printed, dry quickly to tack-free prints, which have a high gloss and very high have a slight odor.
  • a varnish made of 49.5 g resin, 19.6 linseed oil and 30.9 g mineral oil in the boiling range 260 to 290 ° C had a viscosity of 100 Pas at 23 ° C with low to medium tack (tackiness, tack).
  • the resin had a melting point of 105 ° C.
  • the resin had a melting point of 120 ° C, the viscosity at 23 ° C in a 50 wt .-% toluene solution was 25 mPas.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

On obtient lesdits produits par (A) transformation de 100 parties en poids de colophane avec entre 1 et 20 parties en poids d'anhydride d'acide maléique à une température comprise entre 150 et 250°C; (B) retransformation du produit d'addition (A) obtenu lors de la phase (A) avec une diamine organique diprimaire à des températures comprises entre 130 et 250°C, le rapport molaire entre groupes anhydrides et groupes amino étant compris entre 0,8 et 1,2 pour 1; (C) retransformation du produit de condensation (B) obtenu lors de la phase (B) avec un polyol dont la fonctionnalité est comprise entre 3 et 6 à des températures comprises entre 230 et 300°C, le rapport molaire entre groupes carboxyles et hydroxiles étant compris entre 0,7 et 1,5 pour 1.
EP19890912450 1988-11-04 1989-10-31 Produits de condensation a base de colophane-maleinimides Withdrawn EP0444065A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3837520 1988-11-04
DE3837520A DE3837520A1 (de) 1988-11-04 1988-11-04 Kondensationsprodukte auf basis von kolophonium-maleinimiden

Publications (1)

Publication Number Publication Date
EP0444065A1 true EP0444065A1 (fr) 1991-09-04

Family

ID=6366528

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890912450 Withdrawn EP0444065A1 (fr) 1988-11-04 1989-10-31 Produits de condensation a base de colophane-maleinimides

Country Status (6)

Country Link
EP (1) EP0444065A1 (fr)
JP (1) JPH04503219A (fr)
AU (1) AU630126B2 (fr)
DE (1) DE3837520A1 (fr)
ES (1) ES2019495A6 (fr)
WO (1) WO1990005158A1 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1232058A (fr) * 1967-10-10 1971-05-19

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9005158A1 *

Also Published As

Publication number Publication date
JPH04503219A (ja) 1992-06-11
DE3837520A1 (de) 1990-05-10
AU4511889A (en) 1990-05-28
ES2019495A6 (es) 1991-06-16
WO1990005158A1 (fr) 1990-05-17
AU630126B2 (en) 1992-10-22

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Legal Events

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Effective date: 19910322

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Designated state(s): AT BE CH DE FR GB IT LI NL

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Owner name: BASF LACKE + FARBEN AG

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Effective date: 19921124

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