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EP2802609A1 - Réticulation photo-induite de polymères contenant des doubles liaisons au moyen d'une réaction péricyclique - Google Patents

Réticulation photo-induite de polymères contenant des doubles liaisons au moyen d'une réaction péricyclique

Info

Publication number
EP2802609A1
EP2802609A1 EP12801585.6A EP12801585A EP2802609A1 EP 2802609 A1 EP2802609 A1 EP 2802609A1 EP 12801585 A EP12801585 A EP 12801585A EP 2802609 A1 EP2802609 A1 EP 2802609A1
Authority
EP
European Patent Office
Prior art keywords
groups
formulation
component
polymer
group
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Withdrawn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
EP12801585.6A
Other languages
German (de)
English (en)
Inventor
Friedrich Georg Schmidt
Stefan Hilf
Christopher Barner-Kowollik
Nathalie GUIMARD
Kim Klaus ÖHLENSCHLÄGER
Jan Müller
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.)
Evonik Industries AG
Original Assignee
Evonik Industries 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 Evonik Industries AG filed Critical Evonik Industries AG
Publication of EP2802609A1 publication Critical patent/EP2802609A1/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Withdrawn legal-status Critical Current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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/28—Treatment by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/06—Crosslinking by radiation

Definitions

  • the present invention relates to a novel method for the photoinduced crosslinking of, for example, adhesive or coating compositions.
  • the present invention relates to a new, irreversible
  • Crosslinking mechanism in which, by irradiation with visible light, specific photoactive systems can be generated via photoenol reactions specifically highly reactive diene intermediates, the double bond-containing polymers by means of a Diels-Alder reaction.
  • photo-crosslinkable polymers are also of interest in sealants, coating compositions such as paints or coatings or in the production of moldings.
  • WO 201 1/101776 describes the reversible crosslinking of poly (meth) acrylates by means of a hetero-Diels-Alder reaction.
  • this reaction can only be thermally activated and deactivated.
  • the disadvantage of such a system, especially for paint applications is that a thermally re-releasable crosslinking severely limits the longevity and the possibility of using such a system.
  • the UV radiation curable coating compositions set forth in WO 98/033855 must be cured with very high irradiation energies, excluding oxygen. Without these high light energies or in the presence of oxygen, coatings are often obtained which show a low resistance to solvents. Accordingly, the processability of these coating compositions is relatively expensive.
  • US Pat. No. 7,829,606 discloses radiation curable reactive hot melt adhesives. These consist of polyacrylates and long-chain acrylate monomers. In doing so, the
  • Curing application-specific only with a relatively low degree of crosslinking This technology can not be transferred to other applications, such as UV-curable coatings.
  • Photoenol compounds for functionalization e.g. coupled with OH groups.
  • Triblock copolymers by the same mechanism as Gruendling et al.
  • PMMA or polystyrene polymers which have benzophenone groups at one chain end and cyclopentadiene groups at the other chain end are each coupled with maleimide-engroup-functional PEG or acrylate polymers to form triblock copolymers.
  • the coupling is photoinduced at one end of the chain, while the coupling at the other end of the chain, the cyclopentadiene group having thermally induced takes place.
  • the respective end-group-functional polymers have to be prepared cumbersomely by means of anionic or, in the case of poly (meth) acrylates, alternatively by means of a controlled radical polymerization.
  • only mono- or at best bifunctional polymer chains are available by means of these methods. However, crosslinking reactions are excluded.
  • Object of the present invention is to provide a new photo-inducible crosslinking method, which in different applications and in a broad
  • the object is to provide a photo-inducible crosslinking method which can be used for many polymer systems, in particular for poly (meth) acrylates or poly (meth) acrylates-containing mixed systems.
  • Binder for various polymers can be used.
  • the mechanism also provides new crosslinkable formulations. Surprisingly, it has been found that the stated objects can be achieved by a formulation which can be crosslinked by means of a photoinduced Diels-Alder reaction or a hetero-Diels-Alder reaction.
  • the formulations according to the invention contain a component A which has at least two dienophilic double bonds and a component B which has at least two diene group-forming functionalities.
  • the formulation is crosslinkable by means of UV radiation.
  • at least one of these two components A or B must have more than two, preferably at least three of the respective functionalities.
  • at least one of the components A or B is present as a polymer.
  • the component having at least three functionalities may be a polymer and the component having two functionalities may be a low molecular weight substance or an oligomer.
  • the formulation is crosslinkable by means of UV radiation.
  • at least one of these two components A or B must have more than two, preferably at least three of the respective functionalities.
  • at least one of the components A or B is present as a polymer.
  • the component having at least three functionalities may be a polymer and the component having two functionalities may be a low molecular weight substance or an oligomer.
  • both components have at least three functionalities, regardless of which of the two components is a polymer.
  • both components are polymers having at least three functionalities.
  • component B is a compound which is the
  • Diene groups forms and to at least two substituted carbonyl groups of the structure
  • R 1 is hydrogen, an aryl group or an alkyl group, preferably hydrogen.
  • R 2 is a benzyl group or a
  • Carbonyl functionalities can serve.
  • the carbonyl groups are connected to one another via one of the groups R 3 to R 6 or R 1 .
  • the linkage preferably takes place via the group R 4 or R 6 , more preferably via R 6 .
  • this group is preferably bonded to the aromatic radical of the carbonyl group (I) by means of an oxygen or sulfur atom, particularly preferably as ether.
  • component B is in a form according to formula (II):
  • R 1 could be formed from an appropriately substituted benzene ring.
  • R 7a is preferably an at least 2-membered group which is an aromatic, an alkyl group, a combination of aromatics and alkyl groups or a polymer or oligomer.
  • P is a number between 2 and 50, preferably a number between 2 and 30.
  • the number p of low molecular weight compounds is generally an integer between 2 and 5, preferably 2 or 3.
  • R 7a is a polymer
  • p is preferably a number between 2 and 50, preferably between 3 and 30 and particularly preferably between 5 and 30.
  • component B is a compound of the structure
  • R 7 is an at least 2-membered aryl or alkyl group or a polymer.
  • R 7 is a 2- to 3-membered aryl group.
  • component B is a polymer having more than 2 carbonyl groups.
  • Component A is a compound having at least two dienophilic groups.
  • the dienophilic groups have the general structure
  • Z is an electron-withdrawing group.
  • R 10 , R 11 and R 12 are each independently hydrogen, alkyl or aryl groups.
  • R 8 is CR 12 R 13 or a sulfur atom.
  • R 12 and R 13 may independently be hydrogen, alkyl or aryl groups.
  • R 9 is an SR 10 group.
  • the group Z is a 2-pyridyl group.
  • Phosphoryl group or a sulfonyl group are particularly suitable.
  • particularly suitable are: cyano or trifluoromethyl groups and any other group Z, which the
  • Electron density of the R 8 -C double bond is greatly reduced, thus allowing a rapid Diels-Alder reaction.
  • dithioesters examples include benzylpyridin-2-yl dithioester (BPDT, V), 1-phenylethyl (diethoxyphosphoryl) dithioester (PDEPDT, VI) and cumyl benzyl dithioester (CBDT, VII)
  • R 9 may be alkyl, aryl, phosphoryl, ether, amino, or thioether groups.
  • the linkage with the other dienophile groups can take place via the groups R 8 , R 9 or Z, preferably via the group R 9 .
  • the carriers for the individual groups may preferably be alkyl or aryl groups, as well as polymers. These are necessarily polymers when component B is present as a low molecular weight compound.
  • dienophile groups are maleic acid ester, maleic acid half ester or maleimide groups (IX):
  • R is the group through which several of the maleimide groups are linked. It is preferably a polymer.
  • the maleimide group can be incorporated in the form of a protected monomer into a poly (meth) acrylate. The following synthetic route is shown as an example:
  • a protected monomer (X) is first copolymerized and then removed the protective group in vacuo.
  • acrylic groups are present in side groups and / or at the chain ends.
  • acrylic groups are very suitable dienophiles.
  • the acrylate groups are equally suitable for polyethers or polybutadienes prepared by ionic polymerization.
  • Methacrylic groups are also suitable, even if they are less active than acrylic groups.
  • Particularly suitable are also blocks which during a
  • polymer chain such as: a polyester incorporated.
  • building blocks are maleic acid, fumaric acid or itaconic acid and anhydrides of maleic acid or itaconic acid.
  • vinyl halide groups, vinylbenzyl groups, acrolein or Cyyanacrylat phenomenon be used
  • copolymerizable diene compounds which are in particular for polyolefins, such as EPDM, are common, and to double bonds, which could be under very strong activation by a particularly electron-rich diene and by catalysis suitable , are 1, 4-hexadiene, ethylidene norbornene or bicyclopentadiene.
  • component A as component A a
  • low molecular weight organic compound having at least 2, preferably 2 to 4
  • component B is present as a polymer.
  • these polymers may be different or the same polymers, differing only in functional groups.
  • the polymers may be polyacrylates, polymethacrylates, polystyrenes,
  • Star copolymers of these polymers act. These star polymers can have over 30 arms. The composition of the arms may vary and be composed of different polymers. Again, these arms may in turn have branching points. The comb polymers may have a block structure and variable
  • (meth) acrylates is alkyl esters of acrylic acid and / or methacrylic acid.
  • formulation and all related percentages in this case refer only to components A and B.
  • Formulation ingredients such as in a coating or
  • Adhesive composition can be added, are not considered in this consideration.
  • formulation in the context of this document exclusively describes components A and B and also an optional crosslinking catalyst.
  • composition additionally includes added components in addition to the formulation.
  • additional components may be additives specially selected for the respective application, such as, for example, fillers, pigments, additives, compatibilizers, co-binders, plasticizers, impact modifiers, thickeners, defoamers, dispersing additives, rheology improvers, adhesion promoters, scratch-resistant additives, catalysts or stabilizers.
  • components A and B are first brought together in the process.
  • the components A and / or B are at least one polymer according to the listing listed above.
  • the formulation in a first process step, is composed of at least two
  • the advantage of the present invention is that the formulation is storage-stable over a long period of time and is easy to apply. The latter arises from the fact that the person skilled in the art has many formulation degrees of freedom, for example in relation to the viscosity.
  • a further advantage is that the crosslinking itself is carried out very quickly, without release of volatile constituents and with known apparatus.
  • the crosslinking can be effected by means of any known and suitable crosslinking lamp or UV light source. The crosslinking takes place at a wavelength that is in the
  • Absorption range of the carbonyl group of component B for Photoenolretress This absorption range can be easily determined by spectroscopic methods. As a rule, the absorption maximum lies between 300 and 400 nm. Thus, the crosslinking also generally takes place at a wavelength between 300 and 400 nm.
  • the crosslinking reaction can be carried out at room temperature within 120 minutes, preferably within 60 minutes, more preferably within 30 minutes and most preferably within 10 minutes.
  • a crosslinking catalyst can be added.
  • the crosslinking is preferably carried out without addition of a crosslinking catalyst.
  • the person skilled in the art may preferably choose the radiation dose and / or the concentration of the
  • the networking takes place in two steps.
  • a first step will be from the
  • This dienol is a very active, electron-rich diene for a Diels-Alder reaction that can spontaneously undergo the same reaction with the component A dienophilic groups described above.
  • Particularly suitable carbonyl groups are the compounds XI to XVI.
  • the ether groups on the aromatic ring may preferably be the coupling sites to the other photoenol groups of the crosslinker or to the polymer containing the other photoenol groups:
  • paints, coatings and paint are examples from the application areas.
  • compositions e.g. porous materials in the expanded state can soak or wet particularly well and result in highly coherent materials as a result of the crosslinking reaction.
  • the weight average molecular weights of the polymers were determined by GPC
  • the NMR analyzes were carried out on a Bruker AM 400 MHz spectrometer.
  • Step 2 Ether Cleavage 4.2 g of 2-methoxy-6-methylbenzaldehyde from Step 1 (28 mmol, 1 eq) were dissolved in 70 ml_
  • Example 3 Crosslinking Reaction of the Polymer from Example 2 1 mg of the crosslinker from Example 1 (2.67 mmol, 2.14 eq) and 5 mg of the maleimide-functionalized polymer from Example 2 (1, 25 mmol, 1, 00 eq) weighed into headspace vials (Pyrex, diameter 20 mm) and dissolved in dichloromethane. The vials were then airtight sealed with a styrene / butadiene rubber seal with a PTFE inner coating.
  • the sample was irradiated by means of a low-pressure fluorescence lamp (Arimed B6, Cosmedico GmbH, Stuttgart, Germany) with a wavelength of 320 nm ( ⁇ 30 nm) from a distance between 40 and 50 mm in a photoreactor over a period of 60 min. After the reaction, the solvent was removed in vacuo. The resulting solid was insoluble in dichloromethane and thus crosslinked.
  • a low-pressure fluorescence lamp Arimed B6, Cosmedico GmbH, Stuttgart, Germany
  • a copolymer of hydroxyethyl methacrylate (HEMA) with other comonomers was prepared by methods known to those skilled in the art.
  • the polymer was dissolved in a suitable anhydrous solvent to give an easily stirrable polymer solution (for example, ethyl acetate) and one mole equivalent of maleic anhydride (calculated on the HEMA content contained) and 0.1 equivalent of triethylamine, followed by 60 ° C for four minutes Hours stirred.
  • the resulting polymer was precipitated in cold hexane, filtered off and dried in vacuo (polymer 585). The degree of reaction is determined by 1 H-NMR.
  • Example 5 Crosslinking Reaction of the Polymer of Example 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne en particulier un nouveau mécanisme de réticulation irréversible permettant de générer, par irradiation avec de la lumière visible, des systèmes photo-actifs spéciaux par l'intermédiaire des niveaux intermédiaires diènes hautement réactifs, de manière ciblée par des réactions énoliques photo-induites, ces niveaux intermédiaires diènes réticulant au moyen d'une réaction de Diels-Alder des polymères contenant des doubles liaisons.
EP12801585.6A 2012-01-10 2012-12-14 Réticulation photo-induite de polymères contenant des doubles liaisons au moyen d'une réaction péricyclique Withdrawn EP2802609A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012200235A DE102012200235A1 (de) 2012-01-10 2012-01-10 Photoinduzierte Vernetzung von Doppelbindungen-enthaltenden Polymeren mittels pericyclischer Reaktion
PCT/EP2012/075541 WO2013104486A1 (fr) 2012-01-10 2012-12-14 Réticulation photo-induite de polymères contenant des doubles liaisons au moyen d'une réaction péricyclique

Publications (1)

Publication Number Publication Date
EP2802609A1 true EP2802609A1 (fr) 2014-11-19

Family

ID=47358204

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12801585.6A Withdrawn EP2802609A1 (fr) 2012-01-10 2012-12-14 Réticulation photo-induite de polymères contenant des doubles liaisons au moyen d'une réaction péricyclique

Country Status (4)

Country Link
US (1) US20140323648A1 (fr)
EP (1) EP2802609A1 (fr)
DE (1) DE102012200235A1 (fr)
WO (1) WO2013104486A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012222742A1 (de) 2012-12-11 2014-03-27 Evonik Industries Ag Funktionsmaterialien mit reversibler Vernetzung
DE102014202947A1 (de) 2014-02-18 2015-08-20 Tesa Se UV-vernetzbare Polymerzusammensetzung
EP3053905A1 (fr) 2015-02-04 2016-08-10 Evonik Degussa GmbH Cycloaddition induite par la lumière visible destinée à la polymérisation ou la réticulation à l'aide de liaisons d'azirine
DE102015108358B3 (de) * 2015-05-27 2016-10-27 Karlsruher Institut für Technologie Hochaufgelöste Photochemie unterhalb des Beugungslimits mittels schaltbarer Photoenolisierung
DE102019113431B4 (de) 2018-06-28 2024-08-22 Bundesdruckerei Gmbh Verfahren und Vorrichtung zur Kennzeichnung einer Datenseite, insbesondere für ein Wert- und/oder Sicherheitsdokument
EP3622943A1 (fr) * 2018-09-11 2020-03-18 Ivoclar Vivadent AG Matières polymérisables à base de dérivés de benzaldéhyde pouvant être dimérisés

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Publication number Priority date Publication date Assignee Title
DE4325776A1 (de) * 1993-07-31 1995-02-02 Roehm Gmbh Verfahren zum Vernetzen von organischen Polymerisaten
EP0956318B1 (fr) 1997-01-30 2006-01-11 DSM IP Assets B.V. Composition pouvant durcir par rayonnement
US6593389B1 (en) * 2001-04-05 2003-07-15 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Polyimides by photochemical cyclopolymerization
CN101595191B (zh) 2006-11-07 2012-11-14 汉高股份两合公司 丙烯酸热熔粘合剂
DE102010001987A1 (de) 2010-02-16 2011-08-18 Evonik Röhm GmbH, 64293 Funktionsmaterialien mit reversibler Vernetzung

Non-Patent Citations (1)

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Title
See references of WO2013104486A1 *

Also Published As

Publication number Publication date
DE102012200235A1 (de) 2013-07-11
WO2013104486A1 (fr) 2013-07-18
US20140323648A1 (en) 2014-10-30

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