DK2013302T3 - Vandige strålehærdbare polyurethansammensætninger - Google Patents

Vandige strålehærdbare polyurethansammensætninger Download PDF

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DK2013302T3
DK2013302T3 DK07727581.6T DK07727581T DK2013302T3 DK 2013302 T3 DK2013302 T3 DK 2013302T3 DK 07727581 T DK07727581 T DK 07727581T DK 2013302 T3 DK2013302 T3 DK 2013302T3
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meth
acrylated
compound
curable composition
groups
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Michel Tielemans
Dirk Bontinck
Overvelt Jean-Claude Van
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ALLNEX Belgium SA
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    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • C09D175/14Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes
    • C09D175/06Polyurethanes from polyesters
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00Materials specially adapted for additive manufacturing
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
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    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/0804Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/67Unsaturated compounds having active hydrogen
    • C08G18/671Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C08G18/673Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
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    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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    • C09D4/00Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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    • BPERFORMING OPERATIONS; TRANSPORTING
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    • B29K2069/00Use of PC, i.e. polycarbonates or derivatives thereof, as moulding material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29KINDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
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    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04Polyurethanes
    • C08L75/14Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31554Next to second layer of polyamidoester
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31591Next to cellulosic
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31598Next to silicon-containing [silicone, cement, etc.] layer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31598Next to silicon-containing [silicone, cement, etc.] layer
    • Y10T428/31601Quartz or glass
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y10T428/00Stock material or miscellaneous articles
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Claims (17)

1. Vandig strålehærdbar sammensætning omfattende - mindst en (meth)acryleret polyurethan-præpolymer (A) opnået fra reaktionen af: - mindst en polyisocyanatforbindelse (i), - mindst en polyol (ii), - mindst en hydrofil forbindelse (iii), der indeholder mindst en reaktiv gruppe, der er i stand til at reagere med isocyanatgrupper, og som er i stand til at gøre polyurethan-præpolymeren opløselig i vandigt medium enten direkte eller efter reaktionen med et neutraliseringsmiddel for at tilvejebringe et salt, - mindst en (meth)acryleret forbindelse (iv), der indeholder mindst to reaktive grupper, der er i stand til reagere med isocyanatgrupper, - mindst en (meth)acryleret forbindelse (v), der indeholder i det væsentlige en reaktiv gruppe, der er i stand til at reagere med isocyanatgrupper udvalgt blandt poly(meth)acryloyl-mono-hydroxyforbindelser, og - eventuelt, mindst en ethylenisk umættet forbindelse (B), hvor sammensætningen omfatter en samlet mængde af (meth)acrylerede og, eventuelt, polymeriserbare ethylenisk umættede grupper på mindst 3 meq pr. g af den samlede vægt af (i), (ii), (iii), (iv), (v) og (B) som målt ved hjælp af 1H kernemagnetisk resonansspektroskopi.
2. Strålehærdbar sammensætning ifølge krav 1, hvor sammensætningen omfatter en samlet mængde af (meth)acrylerede og, eventuelt, polymeriserbare ethylenisk umættede grupper på mindst 3,5 meq 4 pr. g af den samlede vægt af (i), (ii), (iii), (iv), (v) og (B) som målt ved hjælp af 1H kernemagnetisk resonansspektroskopi.
3. Strålehærdbar sammensætning ifølge krav 1 eller 2, hvor den (meth)acry-lerede polyurethan-præpolymer (A) omfatter en samlet mængde af (meth)acrylerede grupper på mindst 3,0 meq af (meth)acrylerede grupper pr. g af samlet vægt af forbindelser (i), (ii), (iii), (iv) og (v) som målt ved hjælp af 1H kernemagnetisk resonansspektroskopi.
4. Strålehærdbar sammensætning ifølge et af de foregående krav opnået ved hjælp af en fremgangsmåde omfattende - et første trin omfattende reaktionen af forbindelser (i), (ii), (iii) og (iv), - et andet trin, omfattende reaktionen af produktet fra det første trin med en forbindelse (v), således at der opnås en endekappet (meth)acryleret poly-urethan-præpolymer (A), - dispergeringen i et vandigt medium af den endekappede (meth)acrylerede polyurethan-præpolymer (A) opnået efter det andet trin, - et valgfrit trin omfattende reaktionen med et neutraliseringsmiddel med henblik på at omdanne de hydrofile grupper tilvejebragt ved hjælp af forbindelse (iii) til anioniske salte, - et valgfrit trin, hvor den (meth)acrylerede polyurethan-præpolymer (A) opnået efter det andet trin reageres med en kædeforlænger (vii), - eventuelt tilsætning afen ethylenisk umættet forbindelse (B).
5. Strålehærdbar sammensætning ifølge krav 4, hvor sammensætningen omfatter en samlet mængde af (meth)acrylerede og, eventuelt, polymeriserbare ethylenisk umættede grupper på mindst 3,5, fortrinsvis mindst 4 meq pr. g af den samlede vægt af (i), (ii), (iii), (iv), (v) og (B) som målt ved hjælp af 1H kernemagnetisk resonansspektroskopi.
6. Strålehærdbar sammensætning ifølge krav 4 eller 5, hvor den (meth)acry-lerede polyurethan-præpolymer (A) omfatter en samlet mængde af (meth)acrylerede grupper på mindst 3,0 meq af (meth)acrylerede grupper pr. g af samlet vægt af forbindelser (i), (ii), (iii), (iv) og (v) som målt ved hjælp af 1H kernemagnetisk resonansspektroskopi.
7. Strålehærdbar sammensætning ifølge et af de foregående krav, hvor poly-olen (ii) har en molekylvægt (middeltal) på mindst 400.
8. Strålehærdbar sammensætning ifølge krav 7, hvor polyolen (ii) er en poly-esterpolyol med en molekylvægt (middeltal) på mindst 400.
9. Strålehærdbar sammensætning ifølge et af de foregående krav, hvor poly-isocyanatet (i) er udvalgt blandt alifatiske og cykloalifatiske polyisocyanater.
10. Strålehærdbar sammensætning ifølge et af de foregående krav, hvor den hydrofile forbindelse (iii) er udvalgt blandt hydroxycarboxylsyrer repræsenteret ved den almene formel (HO)xR(COOH)y, hvor R repræsenterer en carbonhy-dridrest med lige eller forgrenet kæde med 1 til 12 carbonatomer, og x og y uafhængigt er heltal fra 1 til 3.
11. Strålehærdbar sammensætning ifølge et af de foregående krav, hvor den (meth)acrylerede forbindelse (iv) er udvalgt blandt reaktionsprodukterne af dig-lycidylforbindelser med (meth)acrylsyre.
12. Strålehærdbar sammensætning ifølge krav 11, hvor den (meth)acrylerede forbindelse (iv) er diacrylatesteren af bisphenol A-diglycidylether.
13. Strålehærdbar sammensætning ifølge et af de foregående krav, hvor den (meth)acrylerede forbindelse (v) er udvalgt blandt esterificeringsprodukterne af alifatiske og/eller aromatiske polyoler med (meth)acrylsyre med en resterende gennemsnitlig hydroxyl-funktionalitet på ca. 1.
14. Strålehærdbar sammensætning ifølge et af de foregående krav, omfattende en ethylenisk umættet forbindelse (B) udvalgt blandt esterificeringsprodukterne af (meth)acrylsyre med tri-, tetra-, penta og/eller hexahydriske polyoler og deres blandinger.
15. Fremgangsmåde til fremstilling afen strålehærdbar sammensætning ifølge et af de foregående krav omfattende: - et første trin omfattende reaktionen af forbindelser (i), (ii), (iii) og (iv), - et andet trin, omfattende reaktionen af produktet fra det første trin med en forbindelse (v), således at der opnås en endekappet (meth)acryleret polyurethan-præpolymer (A), - dispergeringen i et vandigt medium af den endekappede (meth)acrylerede polyurethan-præpolymer (A) opnået efter det andet trin, - et valgfrit trin omfattende reaktionen med et neutraliseringsmiddel med henblik på at omdanne de hydrofile grupper tilvejebragt ved hjælp af forbindelse (iii) til anioniske salte, - et valgfrit trin, hvor den (meth)acrylerede polyurethan-præpolymer (A) opnået efter det andet trin reageres med en kædeforlænger (vii), - et valgfrit trin omfattende tilsætning af en ethylenisk umættet forbindelse (B).
16. Fremgangsmåde ifølge det foregående krav, yderligere omfattende et trin, hvor der tilsættes en ikke-ethylenisk umættet forbindelse (C) udvalgt blandt silikoneret og/eller hydroxylerede polyacrylater, hvor forbindelsen (C) tilsættes inden, under eller efter det andet trin af reaktionen.
17. Fremgangsmåde til fremstilling af en coatet artikel omfattende et trin, hvor artiklen coates med en strålehærdbar sammensætning ifølge et af kravene 1 til 14.
DK07727581.6T 2006-04-14 2007-03-30 Vandige strålehærdbare polyurethansammensætninger DK2013302T3 (da)

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