DK3074437T3 - Efterbehandlingsmiddel med blokerede polysocyanater - Google Patents

Efterbehandlingsmiddel med blokerede polysocyanater Download PDF

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Publication number
DK3074437T3
DK3074437T3 DK14811787.2T DK14811787T DK3074437T3 DK 3074437 T3 DK3074437 T3 DK 3074437T3 DK 14811787 T DK14811787 T DK 14811787T DK 3074437 T3 DK3074437 T3 DK 3074437T3
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group
hydrophobic
polyisocyanate
butyl
alkyl
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DK14811787.2T
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English (en)
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Dirk Sielemann
Christine Albert
Gunther Duschek
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Rudolf Gmbh
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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/808—Monoamines
    • 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
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/395—Isocyanates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (16)

1. Præparat der indeholder (i) mindst ét blokeret polyisocyanat med formel (I)
(i), hvor R1 uafhængigt er hydrogen, Ci-C4-alkyl eller C6-Cio-cycloalkyl, fortrinsvis hydrogen, R2 uafhængigt er hydrogen, CrC^alkyl eller C6-C10-cycloalkyl, fortrinsvis hydrogen, R3 uafhængigt er hydrogen, CrC^alkyl eller C6-C10-cycloalkyl, fortrinsvis hydrogen, R4 uafhængigt er CrC4-alkyl, C6-Ci0-cycloalkyl eller C7-Ci4-aralkyl, fortrinsvis methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, mere foretrukket tert-butyl, m er et helt tal, der er valgt fra 1, 2, 3, 4 eller 5, n er et tal fra 2 til 10, fortrinsvis fra 2 til 8, mere fortrinsvis fra 2 til 6, og Y er en polyisocyanatgruppe, der er substitueret med en hydrofob og eventuelt en anionisk, kationisk og/eller ikke-ionisk gruppe, hvilken hydrofobe gruppe er en lineær, cyklisk eller forgrenet, mættet eller mindst delvist umættet carbonhydridgruppe med 8-24 carbonatomer; og (ii) mindst ét oleofobt og/eller hydrofobt efterbehandlingsmiddel.
2. Præparat ifølge et hvilket som helst af de foregående krav, hvor R1, R2 og R3 hver er H og R4 er tert-butyl.
3. Præparat ifølge krav 1 eller 2, hvor polyisocyanatgruppen Y er en alifatisk, cycloalifatisk og/eller aromatisk carbonhydrid med 6-200 carbonatomer, hvilken gruppe eventuelt indeholder mindst en urethan-, allophanat-, urinstof-, biuret-, uretdion-, isocyanurat-, carbodiimid-, iminooxadiazindion- og/eller uretonimin-gruppe.
4. Præparat ifølge et hvilket som helst af de foregående krav, hvor den hydrofobe og/eller anioniske, kationiske og/eller ikke-ioniske gruppe er bundet til polyisocyanatgruppen via en urethangruppe og/eller via en urinstofgruppe.
5. Præparat ifølge et hvilket som helst af de foregående krav, hvor den anioniske gruppe omfatter et carboxylat og/eller et sulfonat, og den kationiske gruppe omfatter en kvaternær ammoniumion.
6. Præparat ifølge et hvilket som helst af de foregående krav, hvor den ikke-ioniske gruppe omfatter et polyalkylenoxid med en vægtgennemsnitlig molekylvægt på fra 200 til 2000 g/mol, fortrinsvis fra 400 til 1000 g/mol.
7. Præparat ifølge et hvilket som helst af de foregående krav, hvor det blokerede polyisocyanat har formlen (II)
hvor Z er en polyisocyanatgruppe, T er en hydrofob gruppe, W er en kationisk, anionisk og/eller ikke-ionisk gruppe, B er -O- og/eller -NH-, o er 0,1 til 4, fortrinsvis 0,1 til 1, p er 0 til 1, fortrinsvis 0,1 til 0,5 og R1 til R4, m og n er defineret som ovenfor.
8. Præparat ifølge et hvilket som helst af de foregående krav, hvor det oleofobe og/eller hydrofobe efterbehandlingsmiddel omfatter mindst en fluorcarbonpolymer, som fortrinsvis omfatter mindst en gentagelsesenhed med formel (III)
hvor R er H eller CH3, a er et helt tal mellem 0 og 6, fortrinsvis 2 og b er et helt tal mellem 0 og 6, fortrinsvis 4.
9. Fremstilling ifølge et hvilket som helst af de foregående krav, hvor det hydrofobe efterbehandlingsmiddel er fluorfrit og fortrinsvis indeholder voks, poly(meth)acrylat, polyurethan, fedtsyremodificeret melamin, organopolysiloxan, metalsalt affedtsyrer, fedtsyrekondensationsprodukter eller blandinger deraf.
10. Præparat ifølge et hvilket som helst af de foregående krav, hvilket præparatet yderligere omfatter mindst ét organisk opløsningsmiddel, vand eller blandinger deraf.
11. Blokeret polyisocyanat med formel (II)
hvor Z, W, T, B, R1 til R4, m, n, o og p er defineret som ovenfor, hvor den hydrofobe gruppe T er en lineær, cyklisk eller forgrenet, mættet eller mindst delvist umættet carbonhydridgruppe med 8-24 carbonatomer.
12. Fremgangsmåde til fremstilling af et blokeret polyisocyanat med formel (II), hvilken fremgangsmåde omfatter trinnene: (i) at tilvejebringe et polyisocyanat (ii) at omsætte polyisocyanatet med benzylamin med formel (IV)
hvor R1 uafhængigt er hydrogen, CrC4-alkyl eller C6-C10-cycloalkyl, fortrinsvis hydrogen, R2 uafhængigt er hydrogen, CrCValkyl eller C6-C10-cycloalkyl, fortrinsvis hydrogen, R3 er uafhængigt hydrogen, CrCU-alkyl eller C6-C10-cycloalkyl, fortrinsvis hydrogen, R4 er uafhængigt Ci-C4-alkyl, C6-Ci0-cycloalkyl eller C7-Ci4-aralkyl, fortrinsvis methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, mere foretrukket tert-butyl, m er et helt tal valgt fra 1,2, 3, 4 eller 5, med en forbindelse der indeholder en hydrofob og eventuelt anionisk, kationisk og/eller ikke-ionisk gruppe, hvilken forbindelse indeholder et isocyanatreaktivt hydrogenatom, hvor den hydrofobe gruppe er en lineær, cyklisk eller forgrenet, mættet eller i det mindste delvist umættet carbonhydridfunktionsgruppe med 8-24 carbonatomer.
13. Kit der omfatter (i) mindst et blokeret polyisocyanat med formel (I) og/eller (II) som defineret i et hvilket som helst af kravene 1-7 eller 11, og (ii) mindst ét oleofobt og/eller hydrofobt efterbehandlingsmiddel som defineret i krav 8 eller krav 9.
14. Anvendelse af et præparat ifølge et hvilket som helst af kravene 1-10, en forbindelse ifølge krav 11 eller et kit ifølge krav 13 til oleofob og/eller hydrofob efterbehandling af stoffer, især tekstiler.
15. Fremgangsmåde til efterbehandling af stoffer, især tekstiler, hvilken fremgangsmåde omfatter trinnene: (a) at tilvejebringe et præparat ifølge et hvilket som helst af kravene 1-10 eller at blande kitkomponenterne (i) og (ii) ifølge krav 13; (b) at påføre præparatet eller blandingen opnået i trin (a) på et stof, og (c) at behandle stoffet termisk.
16. Oleofobt og/eller hydrofobt efterbehandlet stof, især et tekstil, der kan opnås ved trinnene: (i) at påføre et præparat ifølge et hvilket som helst af kravene 1-10 eller en blanding af kitskomponenterne (i) og (ii) ifølge krav 13 på et stof, især et tekstil; og (ii) behandle stoffet termisk.
DK14811787.2T 2013-11-26 2014-11-24 Efterbehandlingsmiddel med blokerede polysocyanater DK3074437T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102013224140.2A DE102013224140A1 (de) 2013-11-26 2013-11-26 Ausrüstungsmittel mit blockierten Polyisocyanaten
PCT/EP2014/075397 WO2015078811A1 (de) 2013-11-26 2014-11-24 Ausrüstungsmittel mit blockierten polyisocyanaten

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DK3074437T3 true DK3074437T3 (da) 2018-04-23

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US (1) US10253450B2 (da)
EP (1) EP3074437B1 (da)
JP (1) JP6649886B2 (da)
KR (1) KR101956377B1 (da)
DE (1) DE102013224140A1 (da)
DK (1) DK3074437T3 (da)
ES (1) ES2658141T3 (da)
MX (1) MX357782B (da)
PE (1) PE20160876A1 (da)
TR (1) TR201802299T4 (da)
WO (1) WO2015078811A1 (da)
ZA (1) ZA201603357B (da)

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EP3074437A1 (de) 2016-10-05
US20170022657A1 (en) 2017-01-26
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DE102013224140A1 (de) 2015-05-28
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MX2016006797A (es) 2017-02-17
KR20160091947A (ko) 2016-08-03
EP3074437B1 (de) 2018-01-17
CN105980427A (zh) 2016-09-28
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PE20160876A1 (es) 2016-09-10
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