EP1709094A2 - Melanges thermiquement polymerisables composes de macromonomeres multifonctionnels, initiateurs de polymerisation et utilisation de ces melanges comme liants pour des substrats - Google Patents

Melanges thermiquement polymerisables composes de macromonomeres multifonctionnels, initiateurs de polymerisation et utilisation de ces melanges comme liants pour des substrats

Info

Publication number
EP1709094A2
EP1709094A2 EP05700913A EP05700913A EP1709094A2 EP 1709094 A2 EP1709094 A2 EP 1709094A2 EP 05700913 A EP05700913 A EP 05700913A EP 05700913 A EP05700913 A EP 05700913A EP 1709094 A2 EP1709094 A2 EP 1709094A2
Authority
EP
European Patent Office
Prior art keywords
macromonomers
thermally polymerizable
polymerizable mixtures
contain
multifunctional
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Withdrawn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
EP05700913A
Other languages
German (de)
English (en)
Inventor
Kathrin Michl
Matthias Gerst
Yvonne Heischkel
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1709094A2 publication Critical patent/EP1709094A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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 end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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 end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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 end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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 end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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 end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
    • 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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the invention relates to thermally polymerizable mixtures of multifunctional macromonomers and polymerization initiators and their use as binders for substrates.
  • US Pat. No. 5,932,665 discloses polycarboxy polymer-based binders, with this system it being possible to harden at lower temperatures by adjusting the molecular weight and the copolymer composition than in comparable systems made from homopolyacrylic acids.
  • multifunctional acrylic or methacrylic compounds are suitable, for example oligomers or polymers with polymerizable, unsaturated functional groups such as acrylate, methacrylate, vinyl, vinyl ether, allyl or maleate groups, which in the sense of chain extension and / or Cross-linking react.
  • the binder can be a mixture of such oligomers and contain a photoinitiator.
  • the epoxy compounds are generally added to the reaction product obtained in the first stage in amounts of 1 to 20% by weight, preferably 5 to 15% by weight, based on the reaction product in the first stage. Equimolar amounts of epoxy compounds are particularly preferably used, based on the amounts of acid equivalents still present in the reaction product of the first stage.
  • excess or unreacted acid in particular acrylic acid and / or methacrylic acid, but also, for example, dicarboxylic acid still present in a mixture as a starting material or monoesters of dicarboxylic acids formed with a free acid group are bound as epoxy esters ,
  • the reaction with epoxy compounds is preferably carried out at 90 to 130, preferably at 100 to 110 ° C.
  • reaction of the epoxy compounds with the acid groups of the reaction products obtained in the first stage is preferably carried out in the presence of quaternary ammonium or phosphonium compounds, cf. EP-A-0686 621. They are described in Amounts of, for example, 0.01 to 5, in particular 0.1 to 2,% by weight, based on epoxy compounds.
  • Suitable polymerization initiators are, for example, peroxides, hydroperoxides, peroxydisulfates, percarbonates, peroxiesters, hydrogen peroxide and azo compounds.
  • initiators which can be water-soluble or water-insoluble, are hydrogen peroxide, dibenzoyl peroxide, dicyclohexyl peroxidicarbonate, dilauroyl peroxide, methyl ethyl ketone peroxide, di-tert-butyl peroxide, acetylacetone peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, tert-butyl peroxide,.
  • the known redox initiator systems can also be used as polymerization initiators.
  • Such redox initiator systems contain at least one peroxide-containing term compound in combination with a redox coinitiator, for example reducing sulfur compounds, for example bisulfites, sulfites, thiosulfates, dithionites and tetrathionates of alkali metals and ammonium compounds.
  • a redox coinitiator for example reducing sulfur compounds, for example bisulfites, sulfites, thiosulfates, dithionites and tetrathionates of alkali metals and ammonium compounds.
  • Combinations of peroxodisulfates with alkali metal or ammonium bisulfites can be used, for example ammonium peroxydisulfate and ammonium disulfite.
  • the amount of the peroxide-containing compound to the redox coinitiator is, for example, 30: 1 to 0.05: 1.
  • Bound nonwovens are used, for example, as insulation material in the form of sheets or panels in the construction sector.
  • the binders according to the invention are also suitable for the production of pot cleaners and pot scrapers based on bonded nonwovens.
  • the solvent was then distilled off in vacuo (20 mbar) at 100.degree. After the distillation, the acid number of the resin was approximately 1 mg KOH / g. It had a viscosity of 90 mPas according to DIN 53019.
  • the polyether acrylate resin thus obtained was then mixed with 2% t-butyl perbenzoate.
  • Formulation of the binder 1% each (based on solids) of Silquest A-1100 (-aminopropyltriethoxysilane).
  • the glass fleece was placed in a 5% solution of the binder (a mixture of multifunctional macromonomers and peroxide prepared according to Examples 1 to 4) in acetone.
  • the impregnated material was predried at 60 ° C. for 5 min after the solution had drained off.
  • the amount of binder was set to 20% + - 2%.
  • the impregnated nonwovens were cured for 3 minutes at 200 ° C. on a PES store as a carrier in a Mathis dryer (hot air was set to maximum).
  • test specimens for testing the tensile strength and 6 test specimens for testing the bending stiffness in the longitudinal direction were cut out of the impregnated nonwovens.
  • the size of the fleeces for testing was
  • the averaged test values were given in N / 5cm, the clamping length was 200mm for testing the tensile strength "dry” and “wet”, 140mm for testing the tensile strength.
  • the pull-off speed was set to 25 mm / min When measured “hot”, the sample was heated to 180 ° C. in a sample chamber within one minute. After another minute at 180 ° C the tear strength was determined.
  • the tensile strengths were weight-corrected to 60 g / m 2 (calculation formula: F max * 60 [g / m 2 ] / “actual weight” [g / m 2 ]). They are given in the tables.
  • test strips were each fastened in a clamping device and bent at a distance of 10 mm over a holder at an angle of 20 °.
  • the height of the test strip was 30 mm.
  • the measured force represented the bending stiffness.
  • a total of 6 test specimens were measured from the front and rear and an average was determined. The results obtained are given in the tables.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention concerne des mélanges thermiquement polymérisables composés de macromonomères multifonctionnels qui contiennent au moins un groupe radicalement polymérisable. L'invention concerne également des initiateurs de polymérisation ainsi que l'utilisation de ces mélanges comme liants pour des substrats, notamment comme liants pour des fibres de verre, la laine minérale, des fibres naturelles, des fibres synthétiques et la liaison du sable à noyaux.
EP05700913A 2004-01-21 2005-01-14 Melanges thermiquement polymerisables composes de macromonomeres multifonctionnels, initiateurs de polymerisation et utilisation de ces melanges comme liants pour des substrats Withdrawn EP1709094A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004003262A DE102004003262A1 (de) 2004-01-21 2004-01-21 Thermisch polymerisierbare Mischungen aus multifunktionellen Makromonomeren und Polymerisationsinitiatoren und ihre Verwendung als Bindemittel für Substrate
PCT/EP2005/000311 WO2005070982A2 (fr) 2004-01-21 2005-01-14 Melanges thermiquement polymerisables composes de macromonomeres multifonctionnels, initiateurs de polymerisation et utilisation de ces melanges comme liants pour des substrats

Publications (1)

Publication Number Publication Date
EP1709094A2 true EP1709094A2 (fr) 2006-10-11

Family

ID=34745003

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05700913A Withdrawn EP1709094A2 (fr) 2004-01-21 2005-01-14 Melanges thermiquement polymerisables composes de macromonomeres multifonctionnels, initiateurs de polymerisation et utilisation de ces melanges comme liants pour des substrats

Country Status (5)

Country Link
US (1) US20070161765A1 (fr)
EP (1) EP1709094A2 (fr)
JP (1) JP4348370B2 (fr)
DE (1) DE102004003262A1 (fr)
WO (1) WO2005070982A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6899660B2 (ja) * 2017-02-07 2021-07-07 株式会社日本触媒 硬化性樹脂および硬化性樹脂組成物

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3704098A1 (de) * 1987-02-11 1988-08-25 Basf Ag Strahlungshaertbare acrylate
DE3738079A1 (de) * 1987-11-10 1989-05-18 Basf Lacke & Farben Verfahren zur herstellung von makromonomeren und nach diesem verfahren hergestellte makromonomere
WO1991012284A1 (fr) * 1990-02-14 1991-08-22 Elf Atochem S.A. Macromonomeres multisequences fonctionnalises et leur procede de fabrication
DE4119857A1 (de) * 1991-06-17 1992-12-24 Basf Lacke & Farben Ueberzugsmittel auf der basis von carboxylgruppenhaltigen polymeren und epoxidharzen
US5275874A (en) * 1991-12-23 1994-01-04 Owens-Corning Fiberglas Technology Inc. Glass fiber insulation bonded with a UV cured system
JP3087871B2 (ja) * 1992-06-02 2000-09-11 東亞合成株式会社 多分岐構造を有するマクロモノマーの製造方法
US5661213A (en) * 1992-08-06 1997-08-26 Rohm And Haas Company Curable aqueous composition and use as fiberglass nonwoven binder
DE4420012A1 (de) * 1994-06-08 1995-12-14 Basf Ag Verfahren zur Herstellung von strahlungshärtbaren Acrylaten
DE4421254A1 (de) * 1994-06-17 1995-12-21 Gruenzweig & Hartmann Verfahren und Vorrichtung zum Polymerisieren von Substanzen in Fasermaterialien, insbesondere Bindemittel in Mineralwollematerialien für Dämmzwecke
JPH095991A (ja) * 1995-06-23 1997-01-10 Japan Synthetic Rubber Co Ltd ドライフィルム製造用放射線硬化性組成物
DE19614845A1 (de) * 1996-04-15 1997-10-16 Basf Ag Verfahren zur Herstellung von mit Acrylkautschuk modifizierten Formmassen und so erhältliche Formmassen
US5932665A (en) * 1997-02-06 1999-08-03 Johns Manville International, Inc. Polycarboxy polymer acid binders having reduced cure temperatures
DE19800676A1 (de) * 1998-01-10 1999-07-15 Henkel Kgaa Verwendung ausgewählter Klebstoffgemische für die Überlappungsverklebung von Rundumetiketten bei ihrem Auftrag auf Kunststoff-Flaschen
EP1137728A1 (fr) * 1998-10-31 2001-10-04 BASF Coatings AG Agent de recouvrement avec unite macromere pour la realisation de revetements multicouches
DE19938759A1 (de) * 1999-08-16 2001-02-22 Basf Coatings Ag Beschichtungsstoff und seine Verwendung zur Herstellung hochkratzfester mehrschichtiger Klarlackierungen
DE10015262A1 (de) * 2000-03-28 2001-10-04 Basf Ag Papierstreichmassen, enthaltend Bindemittel mit Makromonomeren
DE10259673A1 (de) * 2002-12-18 2004-07-01 Basf Ag Verfahren zur Herstellung von strahlungshärtbaren Urethan(meth)acrylaten

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005070982A2 *

Also Published As

Publication number Publication date
JP4348370B2 (ja) 2009-10-21
JP2007518858A (ja) 2007-07-12
US20070161765A1 (en) 2007-07-12
WO2005070982A3 (fr) 2006-08-10
WO2005070982A2 (fr) 2005-08-04
DE102004003262A1 (de) 2005-08-11

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