EP4536720A1 - Résine de réaction à base de méthacrylate d'éthyle - Google Patents

Résine de réaction à base de méthacrylate d'éthyle

Info

Publication number
EP4536720A1
EP4536720A1 EP23731248.3A EP23731248A EP4536720A1 EP 4536720 A1 EP4536720 A1 EP 4536720A1 EP 23731248 A EP23731248 A EP 23731248A EP 4536720 A1 EP4536720 A1 EP 4536720A1
Authority
EP
European Patent Office
Prior art keywords
weight
reaction resin
meth
initiator
accelerator
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.)
Pending
Application number
EP23731248.3A
Other languages
German (de)
English (en)
Inventor
Alexander Klein
Janos LOTZ
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.)
Roehm GmbH Darmstadt
Original Assignee
Roehm GmbH Darmstadt
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 Roehm GmbH Darmstadt filed Critical Roehm GmbH Darmstadt
Publication of EP4536720A1 publication Critical patent/EP4536720A1/fr
Pending 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
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers 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
    • 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
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • 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
    • C09D4/00—Coating 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
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00

Definitions

  • the present invention relates to a reaction resin which contains at least ethyl methacrylate, a prepolymer with an acid number in the range from 1 to 12 mg (KOH)/g. and optionally contains either an initiator or an accelerator.
  • the invention relates to a 2K system which comprises the reaction resin according to the invention and a hardener component, and the use of the 2K system as a road marking, road repair compound, intumescent coating, floor coating, casting resin, building protection, membrane, sealing, coating agent and/or laminating agent.
  • 2K systems containing the reaction resins according to the invention cure without tack even at low ambient temperatures and in contact with atmospheric oxygen. They also have a particularly low level of dirt absorption on their surface, especially when used to produce road markings and/or floor coatings.
  • the particularly low dirt absorption is due in particular to the use of ethyl methacrylate in combination with a prepolymer with an acid number in the range of 1 to 12 mg (KOH)/g.
  • reaction resin and the 2K system can be applied with reduced emissions, in particular reduced monomer emissions. This is particularly the case if the reaction resins in a particularly preferred embodiment of the invention are essentially free of methyl (meth)acrylate. The health risks can be further reduced, particularly when using phthalate-free hardeners to process the new 2K systems. This represents a further particularly preferred embodiment.
  • the reaction resin and 2K system according to the invention have a sufficiently long processing time for manual surface applications, in particular as road marking, road repair compound, intumescent coating, floor coating, casting resin, building protection, sealing, membrane, coating agent and/or laminating agent .
  • reaction resin is understood to mean a mixture of at least one monomer and at least one prepolymer, which can be easily cured when used as a 2-component system.
  • reaction resin is therefore also preferred, the reaction resin containing the following components:
  • the prepolymer preferably has an acid number in the range of 3 to 10 mg (KOH)/g.
  • the acid number is determined according to the invention according to DIN EN ISO 2114:2002 Plastics (polyesters) and coating materials (binders) - Determination of the partial acid number and the total acid number.
  • the at least one prepolymer can be used, for example, to improve the polymerization properties, the mechanical properties, the adhesion to the substrate and the optical properties of the reaction resin and 2K systems produced therefrom.
  • Both polyesters and polyalkyl (meth)acrylates which can be used as the at least one prepolymer, can have additional functional groups, such as double bonds, for example to promote adhesion or for copolymerization.
  • the prepolymers preferably have no double bonds.
  • the reaction resin contains 0 to 50% by weight of at least one oligomer, based on the total weight of the reaction resin.
  • a reaction resin is therefore also preferred in which the at least one oligomer is selected from the group consisting of polyurethane (meth)acrylates, polyethylene glycol, polypropylene glycol and polytetraydrofuran.
  • a reaction resin is therefore also preferred in which the at least one crosslinker is selected from the group consisting of difunctional, trifunctional, tetrafunctional, pentafunctional and hexafunctional (meth)acrylates.
  • a “C3-Ci8-alkyl (meth)acrylate” is understood to mean an alkyl ester of (meth)acrylic acid which has 3 to 18 carbon atoms in the alkyl radical.
  • the alkyl radical can be linear, cyclic or branched.
  • the alkyl radical can also contain aromatics.
  • C3-Ci8-alkyl (meth)acrylates that contain aromatics in the alkyl radical include, for example, benzyl (meth)acrylate.
  • the alkyl radical can contain heteroatoms.
  • the reaction resin optionally contains either at least one initiator or at least one accelerator. In one embodiment of the present invention, the reaction resin contains no initiator and no accelerator.
  • either at least one initiator or at least one accelerator means that preferably the reaction resin only contains the at least one initiator and no accelerator or the reaction resin only contains the at least one accelerator and no initiator.
  • the reaction resin can contain 0.1 to 10% by weight, preferably 1 to 5% by weight, of at least one initiator, based on the total weight of the reaction resin.
  • the at least one initiator is selected from the group consisting of peroxides, azo compounds and persulfates.
  • a reaction resin is therefore also preferred in which the at least one initiator is selected from the group consisting of peroxides, azo compounds and persulfates.
  • Suitable persulfates are, for example, selected from the group consisting of lithium peroxodisulfate, sodium peroxodisulfate, potassium peroxodisulfate and ammonium peroxodisulfate.
  • At least one accelerator means both exactly one accelerator and a mixture of two or more accelerators. Exactly one accelerator is preferred according to the invention.
  • tertiary aromatic substituted amines includes both symmetrical tertiary aromatic substituted amines and asymmetric tertiary aromatic substituted amines.
  • Suitable symmetrical tertiary aromatically substituted amines are, for example, selected from the group consisting of N,N-dimethyl-p-toluidine, N,N-dimethylaniline, N,N-diethylaniline, over-ethoxylated N,N-dihydroxyethyl-p-toluidine, over-propoxylated N, N-Dihydroxypropyl-p-toluidine, N,N-bis-(2-hydroxyethyl)-p-toluidine and N,N-bis-(2-hydroxypropyl)-p-toluidine.
  • Suitable phosphites are, for example, selected from the group consisting of tri-2-ethylhexyl phosphite, tri-2-ethylhexyl trithiophosphite, triisooctyl phosphite, triisooctyl trithiophosphite, tridecyl phosphite, tridecyl trithiophosphite, trilauryl phosphite, trilauryl trithiophosphite, trioctadecyl phosphite, trioctadecyltrithi ophosphite, phenyl didecyl phosphite, phenyl didecyl trithiophosphite, phenyl dilauryl phosphite, phenyl distearyl phosphite, phenyl distearyl trithiophosphite,
  • cold plastics can be produced from two or three components.
  • Cold plastics made of two components so-called 2K systems, are preferred.
  • Cold plastics made of three components are also referred to as 3K systems.
  • a 2K system comprises the following components: a reaction resin according to the invention and a hardener component which contains either 0.1 to 10% by weight of at least one initiator or 0.1 to
  • reaction resin is part of a 2K system
  • the reaction resin usually contains either the at least one initiator or the at least one accelerator.
  • the hardener component contains, for example, 0.1 to 10% by weight, preferably 1 to 5% by weight, of at least one initiator, based on the total weight of the reaction resin contained in the 2K system.
  • the statements and preferences described above for the at least one initiator that may be contained in the reaction resin apply accordingly.
  • the hardener component contains, for example, 0.1 to 5% by weight, preferably 0.5 to 3% by weight, of at least one accelerator, based on the total weight of the reaction resin contained in the 2K system.
  • Particularly suitable dyes are, for example, white, red, blue, green and/or yellow inorganic pigments.
  • White, inorganic pigments such as titanium dioxide are particularly preferred.
  • Fillers are in particular mineral fillers.
  • Mineral fillers are preferably selected from the group consisting of calcium carbonate, barium sulfate, quartz, quartz powder, precipitated silicas, fumed silicas, corundum, glass beads and Cristo balites.
  • Total weight of the 2K system is auxiliary materials and additives for 2K systems.
  • auxiliary materials and additives for 2K systems are known as such and, for example, selected from the group consisting of regulators, plasticizers, paraffins, stabilizers, inhibitors, waxes and/or oils.
  • UV stabilizers in particular come into question as stabilizers.
  • the UV stabilizers are preferably selected from the group consisting of benzophenone derivatives, benzotriazole derivatives, thioxanthonate derivatives, piperidinol carboxylic acid ester derivatives and cinnamic acid esters derivatives.
  • the 2K systems according to the invention can be used, for example, as road markings, as road repair compounds, as a membrane, as a seal, as an intumescent coating, as a floor coating, as a casting resin, as building protection, as a coating agent and/or as a laminating agent.
  • the 2K system was poured into a flat aluminum dish (diameter 5 cm) (1.5 mm layer thickness) and the weight was determined exactly on an analytical balance. After 60 minutes, the weight loss was determined gravimetrically.
  • Dispersing additive 0.2% by weight Disperbyk 167
  • the cold plastic mass is intensively mixed with 2% by weight of hardener component in powder form (50% dibenzoyl peroxide, Perkadox GB-50X, Nouryon company) and applied to a surface at 23 ° C using a drawing shoe with a 1 mm gap width. After one hour, the hardened cold spray plastics are tested for their tendency to become dirty.
  • hardener component in powder form (50% dibenzoyl peroxide, Perkadox GB-50X, Nouryon company) and applied to a surface at 23 ° C using a drawing shoe with a 1 mm gap width. After one hour, the hardened cold spray plastics are tested for their tendency to become dirty.
  • Comparative Examples 11 and 12 show that when using methyl methacrylate as
  • Monomer does not have a negative influence on the acid number of the polymer component Dirt pickup of the marking shows.
  • Comparative Example 8 shows that when using ethyl methacrylate as a monomer, the dirt absorption results in strong dirt absorption due to the absence of acid in the polymer component.
  • Comparative example 10 shows that the use of ethyl methacrylate as a monomer and a polymer component with a high acid number results in strong dirt absorption.
  • the acid number of the polymer component must be in the range according to the invention.

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)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une résine de réaction qui contient au moins du méthacrylate d'éthyle, un prépolymère ayant un indice d'acide allant de 1 à 12 mg (KOH)/g, et éventuellement soit un amorceur soit un accélérateur. L'invention concerne en outre un système 2K qui comprend la résine de réaction selon l'invention et un composant de durcissement et l'utilisation du système 2K en tant que marquage de voie, composé de réparation de voie, revêtement intumescent, revêtement de sol, résine de coulée, protection de bâtiment, membrane, joint, agent de revêtement et/ou agent de stratification.
EP23731248.3A 2022-06-10 2023-06-07 Résine de réaction à base de méthacrylate d'éthyle Pending EP4536720A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22178286 2022-06-10
PCT/EP2023/065163 WO2023237574A1 (fr) 2022-06-10 2023-06-07 Résine de réaction à base de méthacrylate d'éthyle

Publications (1)

Publication Number Publication Date
EP4536720A1 true EP4536720A1 (fr) 2025-04-16

Family

ID=82358479

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23731248.3A Pending EP4536720A1 (fr) 2022-06-10 2023-06-07 Résine de réaction à base de méthacrylate d'éthyle

Country Status (6)

Country Link
US (1) US20250353945A1 (fr)
EP (1) EP4536720A1 (fr)
KR (1) KR20250022141A (fr)
CN (1) CN119256027A (fr)
AU (1) AU2023283651A1 (fr)
WO (1) WO2023237574A1 (fr)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19902685B4 (de) 1999-01-23 2006-08-10 Röhm GmbH & Co. KG Neuartige Urethan(meth)acrylate, Verfahren zu deren Herstellung und deren Verwendung
BR112012001050A2 (pt) 2009-07-16 2016-03-15 Evonik Roehm Gmbh agente de ligação para a produção de marcações de estrada rapidamente pronta para tráfego
DE102011109139A1 (de) 2011-08-02 2013-02-07 Evonik Röhm Gmbh Geruchsarme (meth)acrylische Reaktionsharze
DE102012210121A1 (de) 2012-06-15 2013-12-19 Evonik Industries Ag Härtung von Reaktionsharzen unter Verwendung von asymmetrischen Aminen als Beschleuniger
KR101729300B1 (ko) 2014-06-13 2017-04-21 주식회사 엘지화학 유기 아연 촉매, 이의 제조 방법 및 상기 촉매를 이용한 폴리알킬렌 카보네이트 수지의 제조 방법
EP2979851A1 (fr) 2014-07-28 2016-02-03 Evonik Degussa GmbH Fabrication efficace de demi-produits et composants composites dans le cadre du procédé de pressage à froid utilisant des (méth)acrylates hydroxyfonctionnalisés réticulés par duroplastie à l'aide d'isocyanates ou d'uretdions
EP2987837A1 (fr) 2014-08-20 2016-02-24 Evonik Röhm GmbH Étanchéification de résine de réaction pour marquages plastique à froid à faible potentiel de salissure
US10252290B2 (en) * 2015-08-02 2019-04-09 Dur-A-Flex Inc. Room temperature fast cure composition for low odor floor coating formulations
CN105753367B (zh) 2016-01-25 2018-09-14 重庆鹏方路面工程技术研究院有限公司 一种用于桥梁伸缩缝快速维修的树脂混凝土及其制备方法
EP3515402B1 (fr) 2016-09-23 2024-11-27 Roehm America LLC Composition de liant de résine à base de (méth)acrylate
CN111005287B (zh) 2019-12-25 2021-11-12 山西中涂交通科技股份有限公司 一种道路路面快速修复方法

Also Published As

Publication number Publication date
CN119256027A (zh) 2025-01-03
AU2023283651A1 (en) 2025-01-23
KR20250022141A (ko) 2025-02-14
US20250353945A1 (en) 2025-11-20
WO2023237574A1 (fr) 2023-12-14

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