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WO2002046263A1 - Formulation de resine, procede permettant son durcissement et son utilisation - Google Patents

Formulation de resine, procede permettant son durcissement et son utilisation Download PDF

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Publication number
WO2002046263A1
WO2002046263A1 PCT/DE2001/004649 DE0104649W WO0246263A1 WO 2002046263 A1 WO2002046263 A1 WO 2002046263A1 DE 0104649 W DE0104649 W DE 0104649W WO 0246263 A1 WO0246263 A1 WO 0246263A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin formulation
curing
formulation according
resin
activator
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.)
Ceased
Application number
PCT/DE2001/004649
Other languages
German (de)
English (en)
Inventor
Andreas Hartwig
Monika Sebald
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.)
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
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 DE10127704A external-priority patent/DE10127704A1/de
Application filed by Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Publication of WO2002046263A1 publication Critical patent/WO2002046263A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/09—Use of materials for the conductive, e.g. metallic pattern
    • H05K1/092—Dispersed materials, e.g. conductive pastes or inks
    • H05K1/095—Dispersed materials, e.g. conductive pastes or inks for polymer thick films, i.e. having a permanent organic polymeric binder
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives

Definitions

  • the invention relates to a resin formulation according to the preamble of the main claim, a process for its catalytic curing and its use. Due to the high speed of curing and the moderate temperatures used, as well as the high storage stability of the uncured resin formulation at room temperature, the formulations curing by this process are particularly suitable for use in electronics, electrical engineering, precision engineering and optics.
  • onium salts are usually used as catalysts for curing epoxy resins and vinyl ethers. These are mostly iodonium or sulfonium salts with the non-nucleophilic anions SbF 6 ⁇ AsF 5 " , PF 6 “ or BF 4 " .
  • the reactivity of these initiators decreases in the order given Anions assuming the same organic substituents on the anion.
  • the influence of the anion on the reactivity is attributed to the following three factors: starch of Lewis or Bronsted acid; Degree of ion pair separation between the growing cationic polymer chain and the anion; Ability of the anion to cleave fluoride to form a nucleophilic anion that terminates the reaction.
  • the addition of a photosensitizer is necessary.
  • Can split off fluoride which is particularly corrosive in the presence of moisture.
  • these fluoride ions can cause corrosion of the metal and subsequent delamination of the adhesive bond.
  • hydrophobic anions For use as phase transfer catalysts in heterogeneous aqueous / organic reaction media, hydrophobic anions have been developed that are chemically stable and do not release fluoride. Examples include tetrakis [3,5-bis (trifluoromethyl) phenyl] borate and the corresponding fluoro- or trifluoromethyl-substituted tetraphenylborates. These anions are also part of initiators which are used for the photochemical cationic curing of epoxides and have good solubility in resins, in particular in silicone epoxides. US 5,468,902 and EP 0 562 897 disclose syntheses of these photoinitiators. The optimal effect of these photoinitiators can be achieved by adding photosensitizers such as anthracene or its derivatives.
  • Formulations are introduced, from which the media resistance suffers, and which promote the corrosion of the substrates to be bonded.
  • the object of the present invention is to overcome the disadvantages of the prior art and to provide a resin formulation based on vinyl ethers and / or epoxides which can be cured in particular thermally at a high reaction rate at low temperatures and which has a high storage stability
  • the resin formulation should not contain any compounds or anions that promote corrosion and contain no toxic antimony or arsenic compounds.
  • epoxides and / or vinyl ethers can be cured not only photochemically, but also thermally by adding a whole range of substances, using onium salts with boron organic counterions at moderate temperatures. These substances act as activators and increase reactivity, i.e. the reaction rate is increased and / or the onset temperature is lowered.
  • the onset temperature is the temperature at which a chemical reaction takes place at a technically reasonable rate. The exact determination of the onset temperature is described in DIN53765, thermal analysis.
  • the curable resin formulations of the invention include: one or more monomers containing one or more epoxy groups and / or vinyl ether groups.
  • - - X is selected from the group consisting of nitrogen, oxygen, phosphorus, sulfur, selenium, bromine and iodine - - R 1 and R 2 are the same or different and are carbocyclic or heterocyclic
  • - - Y are fluorine, chlorine and / or hydroxyl groups
  • - - R 3 is the same or different and is an aryl radical which is substituted by one or more electron-withdrawing substituents.
  • an activator in an amount of 0.005 to 10%; comprising one or more components selected from the group consisting of sulfimides, hydroperoxides, peroxides, carboxylic acids, esters with the exception of ⁇ -hydroxycarboxylic esters, carboxylic acid anhydrides, aromatic aldehydes, nitriles, lactones, lactides, N-bromosuccinimide, hydroquinone, glucose, glucose derivatives, amylose or amylose derivatives.
  • the curable resin formulation according to the invention preferably comprises, as monomers, cycloaliphatic epoxides (for example cyclohexene epoxide, 3,4-epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexane carboxylate, vinylcyclohexene diepoxide), glycidyl ethers (for example phenylglycidyl ether, bisphenol A diglyomeric diglycidylphenol oligomeric diglycidylphenol ether) , polymeric epoxides (eg poly (methyl methacrylate-co-3,4-epoxycyclohexylmethyl methacrylate), isobutyl vinyl ether and / or polytetrahydrofuran divinyl ether.
  • cycloaliphatic epoxides for example cyclohexene epoxide, 3,4-epoxycyclohexylmethyl-3 ', 4
  • R 1 and R 2 are the same or different and are phenyl, tolyl or xylyl radicals, and / or linear or branched alkyl or alkylene radicals with 1 to 30 carbon atoms; the radicals R 1 and R 2 are with one or more groups, in particular with alkyl, alkenyl, alkoxy, nitro, fluoro, chloro, bromo, cyano, carboxyl, hydroxyl and / or carbonyl groups, substituted alone or in combination, and / or contain heteroatoms, such as in particular nitrogen, oxygen and / or sulfur.
  • R 3 is the same or different and is a phenyl, biphenyl, naphthyl or anthracenyl radical with the electron-withdrawing substituents F, OCF 3 , CF 3 , N0 2 , CN and / or Cl.
  • Particularly preferred onium borates are sulfonium or iodonium salts with borate anions of the formula [B (C 6 F 5 ) 4 ] ⁇ [B (C 5 H 3 F 2 ) 4 ] -, [B (C 6 F 4 OCF 3 ) 4 ] -, [BF 2 (C 6 F 5) 2] ", [B (C 6 F 4 CF 3) 4] -and / or [B (C 6 H 3 (CF 3) 2) 4] -.
  • the onium borates [X (R 1 ) n (R 2 ) J + [BY a (R 3 ) b ] " have the same radicals R ⁇ R 2 , B, Y and R 3 in the following order for X increasing activity: 0 "S" Se ⁇ P ⁇ N ⁇ S ⁇ 1.
  • the initiator is contained in a curable resin formulation with particularly high activity, preferably in an amount of 0.1 to 5% by weight.
  • the stated activators bring about a reduction in the curing temperature (at which curing can be carried out) or the onset temperature and / or an increase in the reaction rate.
  • the use of the specified activators and the possibility to choose from a large number of activators which can be used offers several advantages.
  • the desired reactivity of the resin formulation can be influenced in a targeted manner by suitable selection of the activators on the one hand and the ratio of activator, initiator and monomer on the other hand. It is possible to set the onset temperature or to lower the onset temperature while the reaction rate remains the same. With a suitable formulation, curing of the resin formulations containing vinyl ether and / or epoxy groups is also possible at room temperature or lower. Likewise, the duration of the hardening can be reduced to the second range while the reaction temperature remains the same.
  • the activity of the activators increases in the following order: sulfimides «hydroperoxides * peroxides « N-bromosuccinimide »hydroquinones» aromatic aldehydes »nitriles * lactides ⁇ Lactones ⁇ glucose * glucose derivatives «amylose» amylose derivatives ⁇ esters ⁇ carboxylic acids ⁇ carboxylic anhydrides.
  • the curable resin formulations according to the invention have high storage stability at room temperature. For example, storage stabilities of more than one week are achieved if the storage temperature is at least 60 ° C below the curing temperature.
  • the resin formulation according to the invention also offers the advantage that it contains no compounds with components such as BF 3 , PF 5 “ , SbF 6 " , AsF 6 " or BF 4 " , and therefore no corrosive fluoride ions can form under the action of moisture.
  • the resin formulation according to the invention contains no toxic components such as antimony or arsenic compounds.
  • the activator is selected from the group consisting of o-benzoic acid sulfimide, terephthalic acid, maleic acid, ethyl acetate, methyl salicylate, maleic anhydride,
  • Ascorbic acid Ascorbic acid derivatives, ⁇ -butyrolactone, glucose, glucose acetates and
  • the activator is contained in a particularly advantageous curable resin formulation in an amount of 0.1 to 5% by weight.
  • the activator can furthermore be a component of the monomer as a functional group. This means that the activator cannot be extracted when exposed to media. For example, in the hardened state there can be no undesirable change in properties (e.g. optical, mechanical or electrical properties) of the resin formulation due to the extraction of the activator.
  • the resin formulation according to the invention additionally contains mono- and / or polyhydric alcohols or mixtures thereof.
  • alcohols which are added to the resin formulation according to the invention are incorporated into the resulting polymer or polymer network during curing. It is therefore possible to adjust the degree of polymerization or the network density when curing epoxides and vinyl ethers using onium salts and thus to influence the dynamic mechanical properties of the cured polymer and also to control the viscosity of the resin formulation by adding alcohols.
  • monohydric or polyhydric alcohols such as poly (ethylene glycol), poly (tetrahydrofuran) and / or polyester polyols, can be used for this purpose.
  • it additionally contains one or more photosensitizers in an amount of 0.05 to 5% based on the overall formulation.
  • Suitable photosensitizers are, in particular, anthracene, phenanthrene and isopropylthioxanthone or mixtures thereof, which are particularly preferably added in an amount of 0.1 to 2% based on the overall formulation.
  • the resin formulation according to the invention additionally contains a stabilizer in an amount of 0.001 to 5% by weight.
  • a stabilizer in an amount of 0.001 to 5% by weight.
  • Amines or amine derivatives are preferably used as stabilizers, which are particularly preferably incorporated into the resin formulation in an amount of 0.05 to 0.5%.
  • Particularly suitable stabilizers are diethylaniline, aniline, dicyandiamide and methylimidazole.
  • the resin formulation according to the invention additionally contains fillers, pigments, plasticizers, adhesion promoters, solvents, non-reactive polymers or oligomers and / or further cationically and / or free-radically curable monomers.
  • the fillers are silver flakes, graphite, metal-coated polymer balls, metal-coated polymer particles, metal-coated glass balls and / or metal-coated glass particles.
  • the curable resin formulations according to the invention are advantageously cured in a process in which the curing is carried out either thermally or thermally and photochemically.
  • curing takes place in a catalytic reaction.
  • a lowering of the curing temperature or the onset temperature is possible due to the contained activators; Due to the moderate temperatures during curing, thermal curing of resin formulations that contain temperature-sensitive additives is also possible. Due to the many different activators, it is possible to set the curing temperature while maintaining the same reaction rate. Likewise, the duration of the hardening can be reduced to the second range while the reaction temperature remains the same.
  • the method according to the invention is particularly suitable for resin formulations for use in electronics, electrical engineering, precision engineering and optics.
  • the process according to the invention is furthermore considerably less cost-intensive and more economical.
  • Another advantage of the method according to the invention is that many different activators are available. Therefore, the curing temperature and / or the curing rate can be controlled by the choice and the amount of activator or activator mixture added.
  • the process according to the invention is advantageously carried out in such a way that the curing temperature is below 130 ° C. and the curing takes less than one hour at this temperature.
  • This makes it possible, in particular, to thermally harden resin formulations which contain temperature-sensitive additives. The danger of unwanted Side reactions such as decomposition due to excessive temperatures can be reduced in this way.
  • the process according to the invention is particularly advantageously carried out in such a way that the curing temperature is below 100 ° C. and the curing takes less than two hours at this temperature.
  • This makes it possible, in particular, to thermally harden resin formulations which contain particularly temperature-sensitive additives, and to connect or coat temperature-sensitive components or materials by means of thermal hardening.
  • This is particularly advantageous when the resin formulation is used in electronics, electrical engineering, precision engineering and optics.
  • the risk of undesirable side reactions such as Decomposition due to excessively high temperatures can be greatly reduced when hardening with the process parameters just mentioned.
  • the resin formulation according to the invention is advantageously used as an adhesive, lacquer,
  • the resin formulation according to the invention is also advantageously used as an underfiller,
  • a particularly preferred form of application is use in electronics, precision engineering or optics, since the resin formulation according to the invention does not
  • Polymer balls, metal-coated polymer particles, metal-coated glass balls and / or metal-coated glass particles are particularly suitable for the production of electrically conductive adhesives or printing pastes. These can be used, for example, for electronic circuits in automotive engineering. applications
  • Epikote 828 LV (Shell) are mixed with 0.1 g tolylcumyliodonium tetrakis entafluorophenyl) borate and 0.1 g ascorbic acid 6-hexadecanate. And stirred until the initiator and activator are dissolved. The 0.2 g samples are completely hardened after 4 h at 90 ° C or after 30 min at 1 10 ° C in the oven and have a non-stick surface. IR spectroscopy shows complete hardening.
  • Example 8 Adjusting the reactivity by varying the activator concentration and combining different activators
  • the results show that the reactivity increases both with increasing catalyst content and with increasing activator content.
  • the curing temperature can be adjusted by combining activators. Ascorbic acid 6-hexadecanate is more reactive in combination with phthalic anhydride than with maleic anhydride.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une formulation de résine durcissant par voie thermique ou thermique et photothermique, qui contient des résines époxy à durcissement cationique ou des vinyléthers, un sel d'onium comme initiateur et un activateur qui accélère le durcissement thermique. L'invention concerne également un procédé permettant de durcir ladite formulation de résine. L'invention vise à ce que ces formulations durcissent rapidement à températures moyennes et soient très stables au stockage. A cet effet, il est prévu de choisir de manière appropriée un activateur d'un genre nouveau et d'avoir un rapport molaire de l'activateur, de l'initiateur et du monomère. Ce procédé permet de procéder au durcissement à température ambiante, d'abaisser le temps de réaction pour qu'il se situe dans la plage des minutes et d'augmenter également la stabilité au stockage à température ambiante en le portant à plus d'une semaine.
PCT/DE2001/004649 2000-12-08 2001-12-07 Formulation de resine, procede permettant son durcissement et son utilisation Ceased WO2002046263A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE10061089.7 2000-12-08
DE10061090 2000-12-08
DE10061090.0 2000-12-08
DE10061089 2000-12-08
DE10127704.0 2001-06-07
DE10127704A DE10127704A1 (de) 2000-12-08 2001-06-07 Harzformulierung, Verfahren zu ihrer Härtung und ihre Verwendung

Publications (1)

Publication Number Publication Date
WO2002046263A1 true WO2002046263A1 (fr) 2002-06-13

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PCT/DE2001/004649 Ceased WO2002046263A1 (fr) 2000-12-08 2001-12-07 Formulation de resine, procede permettant son durcissement et son utilisation

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WO (1) WO2002046263A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006096476A3 (fr) * 2005-03-03 2007-09-07 Exciton Inc Compositions de colorants infrarouges
CN104312510A (zh) * 2014-11-10 2015-01-28 沈阳理工大学 一种热固性树脂胶粘剂的磁热固化方法
CN106687499A (zh) * 2014-09-17 2017-05-17 株式会社大赛璐 固化性组合物、以及使用其的光学元件

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468902A (en) * 1992-03-23 1995-11-21 Rhone-Poulenc Chimie Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith
US5703137A (en) * 1996-03-14 1997-12-30 Rhone-Poulenc Chimie Initiators for the cationic crosslinking of polymers containing organofunctional groups
WO1998028375A1 (fr) * 1996-12-24 1998-07-02 Rhodia Chimie Compositions stables a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents
US5973020A (en) * 1998-01-06 1999-10-26 Rhodia Inc. Photoinitiator composition including hindered amine stabilizer

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5468902A (en) * 1992-03-23 1995-11-21 Rhone-Poulenc Chimie Onium borates/borates of organometallic complexes and cationic initiation of polymerization therewith
US5703137A (en) * 1996-03-14 1997-12-30 Rhone-Poulenc Chimie Initiators for the cationic crosslinking of polymers containing organofunctional groups
WO1998028375A1 (fr) * 1996-12-24 1998-07-02 Rhodia Chimie Compositions stables a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents
US5973020A (en) * 1998-01-06 1999-10-26 Rhodia Inc. Photoinitiator composition including hindered amine stabilizer

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006096476A3 (fr) * 2005-03-03 2007-09-07 Exciton Inc Compositions de colorants infrarouges
US7498123B2 (en) 2005-03-03 2009-03-03 Exciton, Inc. Infrared dye compositions
CN106687499A (zh) * 2014-09-17 2017-05-17 株式会社大赛璐 固化性组合物、以及使用其的光学元件
EP3196222A4 (fr) * 2014-09-17 2018-05-02 Daicel Corporation Composition durcissable et élément optique obtenu à l'aide de celle-ci
US10351663B2 (en) 2014-09-17 2019-07-16 Daicel Corporation Curable composition and optical element obtained using same
CN106687499B (zh) * 2014-09-17 2019-07-19 株式会社大赛璐 固化性组合物、以及使用其的光学元件
CN104312510A (zh) * 2014-11-10 2015-01-28 沈阳理工大学 一种热固性树脂胶粘剂的磁热固化方法

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