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DK2764037T3 - En tværbindelig sammensætning, der er tværbindelig ved reaktionen real michael-addition, og resiner til anvendelse i sammensætningen. - Google Patents

En tværbindelig sammensætning, der er tværbindelig ved reaktionen real michael-addition, og resiner til anvendelse i sammensætningen. Download PDF

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DK2764037T3
DK2764037T3 DK12772905.1T DK12772905T DK2764037T3 DK 2764037 T3 DK2764037 T3 DK 2764037T3 DK 12772905 T DK12772905 T DK 12772905T DK 2764037 T3 DK2764037 T3 DK 2764037T3
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component
resin
reactive
crosslinkable
groups
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Richard Hendrikus Gerrit Brinkhuis
Antonius Johannes Wilhelmus Buser
Petrus Johannes Maria David Elfrink
Ferry Ludovicus Thys
Nicole Mangnus-Verhagen
Wolf Elwin Aloysius Cornelius Adrianus De
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Allnex Netherlands Bv
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    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0205—Oxygen-containing compounds comprising carbonyl groups or oxygen-containing derivatives, e.g. acetals, ketals, cyclic peroxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
    • C—CHEMISTRY; METALLURGY
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C08J3/246—Intercrosslinking of at least two polymers
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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    • C08K5/00—Use of organic ingredients
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    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
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    • 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
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    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
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    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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    • C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
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  • Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Claims (15)

1. RMA-tværbindelig sammensætning omfattende mindst én tvær-bindelig komponent, hvilken mindst ene tværbindelige komponent omfatter reaktive komponenter A og B hver omfattende mindst 2 reaktive grupper, hvori de mindst 2 reaktive grupper af komponent A er sure protoner (C-H) i aktiverede methylen- eller methingrupper, og de mindst 2 reaktive grupper af komponent B er aktiverede umættede grupper (C=C) og en base-katalysator (C), hvilke reaktive komponenter A og B tværbindes ved reaktionen Real Michael Addition (RMA) under base-katalysatorens virkning, kendetegnet ved, at den mindst ene tværbindelige komponent omfattende reaktive komponenter A og B i sammensætningen har et samlet hydroxy-antal på mindre end 60, fortrinsvis mindre end 40 og mere fortrinsvis mindre end 20 mg KOH/g faststoffer.
2. Tværbindelig sammensætning ifølge krav 1, hvori katalysatoren C er et carbonatsalt ifølge formlen X+R0C02-, hvori X+ er en ikke-sur kation, fortrinsvis kvaternær ammonium eller phosphonium, og R er hydrogen eller en substitueret eller ikke-substitueret alkyl-, aryl- eller aralkylgruppe.
3. Tværbindelig sammensætning ifølge kravene 1 - 2, hvori den tværbindelige komponent omfattende komponent A er en polymer omfattende gennemsnitligt 2 til 20, fortrinsvis 4 til 10 aktive C-H-funktioner pr. molekyle.
4. Tværbindelig sammensætning ifølge kravene 1 - 3, hvori mere end 50, fortrinsvis 60, 70, 80, 90 eller 95 % af de reaktive komponenter A i den tværbindelige komponent er malonatgrupper.
5. Tværbindelig sammensætning ifølge kravene 1 - 4 hvori komponenten B omfatter en umættet funktionel acryloyl- eller maleatgruppe, fortrinsvis acryloyl eller en acrylamid.
6. Tværbindelig sammensætning ifølge et hvilket som helst af kravene 1 - 5 omfattende a. mellem 5 og 95 vægt-% af en tværbindelig komponent omfattende komponent A med mindst 2 sure protoner C-H i aktiveret methylen eller methin og b. mellem 5 og 95 vægt-% af en tværbindelig komponent omfattende komponent B med mindst 2 aktiverede umættede grupper (vægt-% i forhold til den tværbindelige sammensætnings samlede vægt) og c. et katalysatorsystem C, der indeholder eller er i stand til at generere en basisk katalysator, der er i stand til at aktivere RMA-reaktionen mellem komponent A og B, fortrinsvis i niveauer på 0,0001 og 0,5 meq/g faststofkomponenter, d. eventuelt en X-H-gruppe indeholdende komponent (D) der også er en Michael-additionsdonor, der er omsættelig med komponent B under virkning af katalysator C, hvori X er C, N, P, O eller S, fortrinsvis C, N eller P, fortrinsvis til stede i mængder på mindst 50 mol-% i forhold til base genereret af komponent C og mindre end 30 mol-% aktive CH-grupper fra komponent A, e. eventuelt mellem 0,1 og 80 vægt-% opløsningsmiddel, fortrinsvis et organisk opløsningsmiddel, som fortrinsvis indeholder mindst 1 vægt-% af en primær alkohol og eventuelt mindst 0,1 -10 vægt-% vand, hvori summen af ovennævnte komponenter er 100 vægtprocent, og hvori den mindst ene tværbindelige komponent omfattende reaktive komponenter A og B i sammensætningen har et samlet hydroxy-antal på mindre end 60, fortrinsvis mindre end 40 og mere fortrinsvis mindre end 20 mg KOH/g faststoffer.
7. Kit med dele til fremstilling af den tværbindelige sammensætning ifølge kravene 1-6 omfattende en del 1 omfattende de tværbindelige komponenter omfattende reaktive komponenter A og/eller B men ingen C og del 2 omfattende komponent C.
8. Polymerisk eller oligomerisk resin A til anvendelse i en RMA-tværbindelig sammensætning ifølge kravene 1 - 7 omfattende en eller flere reaktive komponenter A med en struktur ifølge formel 1:
hvori R er hydrogen eller en alkyl-, aralkyl- eller arylsubstituent, og Y og Y’ er samme eller forskellige substituentgrupper, fortrinsvis alkyl, aralkyl eller aryl (R*), alkoxy (-R*) eller et polymer-backbone, eller hvori -C(=0)-Y og/eller -C(=0)-Y’ er erstattet med CN eller phenyl, og hvilken polymerisk eller oligomerisk resin A har et hydroxy-antal på mindre end 60, fortrinsvis mindre end 40 og mere fortrinsvis mindre end 20 mg KOH/g faststoffer, hvori den polymeriske eller oligomeriske resin er en polyester, polyether, polyepoxy, polyurethan eller polycarbonat, fortrinsvis polyether, polyacrylat, polyester eller polyurethan omfattende reaktiv komponent A.
9. Resin A ifølge krav 8, hvori mere end 50, fortrinsvis 60, 70, 80, 90 eller 95 % af de reaktive komponenter A i den tværbindelige komponent er malonatgrupper.
10. Resin A ifølge kravene 8 til 9 med et molekylvægttal mellem 100 - 20000 gr/mol, fortrinsvis mellem 250 og 10000, endnu mere fortrinsvis mellem 300 og 6000 gr/mol, og fortrinsvis en ækvivalent vægt pr. reaktiv komponent A på 100 - 2000 gr/mol, og fortrinsvis et syre-antal på mindre end 4, fortrinsvis mindre end 3, 2 eller 1 mg KOH/gr.
11. Polymerisk eller oligomerisk resin B til anvendelse i en RMA-tværbindelig sammensætning ifølge kravene 1 - 7 omfattende mindst en eller flere reaktive komponenter B omfattende aktiverede umættede grupper (C=C), fortrinsvis umættede funktionelle acryloyl- eller maleatgrupper (fortrinsvis acryloyl) eller en acrylamid, og hvilken polymeriske eller oligomeriske resin har et hydroxy-antal på mindre end 60, fortrinsvis mindre end 40 og mere fortrinsvis mindre end 20 mg KOH/g faststoffer, hvori den polymeriske eller oligomeriske resin B er en polyester, polyether, polyepoxy, polyurethan eller polycarbonat omfattende reaktive komponent B.
12. Resin B ifølge krav 11 med et molekylvægttal mellem 300 og 20000 gr/mol, fortrinsvis mellem 300 og 10000 eller 6000 gr/mol, fortrinsvis med en ækvivalent vægt pr. reaktiv komponent A eller B på 100 - 2000 gr/mol, og et syre-antal på mindre end 4, fortrinsvis mindre end 3, 2 eller 1 mg KOH/gr.
13. Anvendelse af resin A eller resin B ifølge kravene 8 til 12 eller af en resinblanding af resin A og resin B som tværbindelige komponenter i en RMA-tværbindelig sammensætning ifølge et hvilket som helst af kravene 1 til 7.
14. Anvendelse af den tværbindelige sammensætning ifølge et hvilket som helst af kravene 1 - 7 til fremstilling af belægningssammensætninger, film eller farvestoffer.
15. Belægningssammensætning omfattende den tværbindende sammensætning ifølge et hvilket som helst af kravene 1 - 7 og endvidere omfattende et eller flere belægnings-additiver som pigmenter, co-bindere, opløsningsmidler osv.
DK12772905.1T 2011-10-07 2012-10-08 En tværbindelig sammensætning, der er tværbindelig ved reaktionen real michael-addition, og resiner til anvendelse i sammensætningen. DK2764037T3 (da)

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EP11184439 2011-10-07
PCT/EP2012/069904 WO2013050622A1 (en) 2011-10-07 2012-10-08 A crosslinkable composition cross-linkable by real michael addition reaction and resins for use in said composition

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DK15188769.2T DK2995636T3 (da) 2011-10-07 2012-10-08 Sammensætning til anvendelse i en proces til fremstilling af en rma-tværbindelig sammensætning

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US (5) US20140221542A1 (da)
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KR (1) KR102131463B1 (da)
CN (3) CN103974999B (da)
DK (2) DK2764037T3 (da)
ES (3) ES2629029T3 (da)
PL (3) PL2995636T3 (da)
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JP6373965B2 (ja) 2013-04-08 2018-08-15 オールネックス・ネザーランズ・ビー．ブイ．Ａｌｌｎｅｘ Ｎｅｔｈｅｒｌａｎｄｓ Ｂ．Ｖ． 真マイケル付加（ｒｍａ）反応により架橋可能な組成物
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DE102015105983A1 (de) 2015-04-20 2016-10-20 Mankiewicz Gebr. & Co. Gmbh & Co. Kg Verbesserte Beschichtungssysteme, deren Verwendung zur Beschichtung von Bauteilen sowie damit beschichtete Bauteile für Land- und Baumaschinen
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