EP4396301A1 - Masse thermodurcissable à base de (méth)acrylates et de peroxodicarbonates - Google Patents

Masse thermodurcissable à base de (méth)acrylates et de peroxodicarbonates

Info

Publication number
EP4396301A1
EP4396301A1 EP22758433.1A EP22758433A EP4396301A1 EP 4396301 A1 EP4396301 A1 EP 4396301A1 EP 22758433 A EP22758433 A EP 22758433A EP 4396301 A1 EP4396301 A1 EP 4396301A1
Authority
EP
European Patent Office
Prior art keywords
weight
meth
acrylate
composition
carbon
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
EP22758433.1A
Other languages
German (de)
English (en)
Inventor
Marko Briem
Katharina Maier
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.)
Delo Industrieklebstoffe GmbH and Co Kgaa
Original Assignee
Delo Industrieklebstoffe GmbH and Co Kgaa
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 Delo Industrieklebstoffe GmbH and Co Kgaa filed Critical Delo Industrieklebstoffe GmbH and Co Kgaa
Publication of EP4396301A1 publication Critical patent/EP4396301A1/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
    • 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
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (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
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • 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
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1065—Esters of polycondensation macromers of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C08F4/34—Per-compounds with one peroxy-radical
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides
    • 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
    • C09J133/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters

Definitions

  • WO 2018/089494 A1 describes both heat-curing and dual-curing (meth)acrylate systems. These are characterized by low curing temperatures of 80 °C or less, while at the same time having a high glass transition temperature of 85 °C or higher in the cured state. The high reactivity is achieved through the use of aliphatic peroxodicarbonates.
  • the masses described have insufficient stability at room temperature, which can be disadvantageous and expensive in industrial processes when downtimes occur, especially when using large adhesive containers. After correspondingly long dwell times at room temperature, the masses already tend to partially harden and can therefore no longer be dosed reliably.
  • the object of the invention is to avoid the disadvantages of the compositions known from the prior art and to provide compositions based on (meth)acrylates and peroxodicarbonates which can also be used in complex industrial processes as sealants, adhesives and/or potting compositions can be used.
  • this object is achieved by a heat-curing composition as claimed in claim 1 .
  • composition according to the invention are each described individually below. However, the respective components can be combined with one another and with one another in any desired manner.
  • compositions contain at least one free-radically polymerizable compound (A) which comprises at least one (meth)acrylate.
  • (meth)acrylate within the meaning of the invention includes both acrylates and the analogous methacrylates.
  • heterocyclic, ethoxylated and other monofunctional meth(acrylates) are tetrahydrofurfuryl (meth)acrylate, (2-ethyl-2-methyl-1,3-dioxolate-4-yl)methyl acrylate, 5-ethyl-1,3-dioxane -5-yl)methyl acrylate, caprolactone (meth)acrylate, 2-(2-ethoxyethoxy)ethyl (meth)acrylate and alkoxylated lauryl acrylate.
  • difunctional or higher (meth)acrylates examples include hexanediol di(meth)acrylate, di(trimethylpropane)tetraacrylate, 4-butanediol di(meth)acrylate, tripropylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth) acrylates 1, 10-decanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, cyclohexanedimethylol di(meth)acrylate, nonanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tris-(2-hydroxyethyl)isocyanurateT tri(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol hexa(meth)acrylate, BPA diepoxypropane di
  • the (meth)acrylates mentioned are commercially available, for example, from Arkema Sartomer, BASF, IMG Resins, Sigma Aldrich or TCI.
  • peroxoesters examples include cumene peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, tert-amyl peroxyneodecanoate, tert-butyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxypivalate, tert-amyl peroxypivalate , tert-butyl peroxypivalate, didecanoyl peroxide, dilauroyl peroxide, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, tert-amyl peroxy-2-ethylhexanoate, dibenzoyl peroxide, tert-butyl peroxy-2-ethylhexanoate, tert
  • the customary, commercially available compounds can be used as free-radical photoinitiators (B2), for example ⁇ -hydroxyketones, benzophenone, ⁇ , ⁇ '-diethoxyacetophenone, 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone, 4-isopropylphenyl -2-Hydroxy-2-propyl ketone, 4,4-bis(diethylamino)benzophenone, 2-ethylhexyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate, 2-butoxyethyl-4-
  • the free radical photoinitiator (B2) is optionally present in the compositions of the invention in an amount of from 0.01 to 7% by weight based on the total weight of components (A) to (E) of the composition.
  • compositions according to the invention comprise at least one stabilizer (C) which comprises at least one sterically hindered phenol (C1).
  • Particularly advantageous combinations of reactivity of the curable compositions with a simultaneously long processing time at room temperature can be achieved by using sterically hindered phenols (C1) which have a molar mass of less than 500 g/mol and/or preferably have at most one phenol group per molecule.
  • C1 sterically hindered phenols
  • Suitable examples of sterically hindered phenols (C1) are 2,4-di-tert-butylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4-methylphenol, 2,6-di-tert-butyl- 4-methylphenol, 2,4,6-tri-tert-butylphenol, 2,4,6-trimethylphenol, 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4- ethylphenol, 4,4'-methylenebis(2,6-di-tert-butylphenol), 3,5-di-tert-butyl-4-hydroxybenzyl alcohol, 3,5-di-tert-butylcatechol, 2,2-methylenebis( 4-methyl-6-tert-butylphenol), 6-tert-butyl-2,4-xylenol, (Ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl
  • the sterically hindered phenol (C1) is present in the compositions according to the invention in a proportion of 0.001 to 3% by weight, preferably 0.01 to 1% by weight, based on the total weight of components (A) to (E). Dimensions.
  • the other stabilizers can be present in the composition in a proportion of 0 to 5% by weight, also based on the weight of components (A) to (E).
  • the presence of the synergist (D) in the compositions according to the invention means that processing times at room temperature of at least 48 hours, preferably at least 120 hours, particularly preferably at least 168 hours, can be achieved.
  • Component (D) is preferably present in solid form in the compositions according to the invention.
  • the synergist (D) and can be selected from the usual allotropic modifications of carbon, provided that the carbon modifications have unsaturated carbon-carbon bonds.
  • the synergist (D) can be selected from the group consisting of carbon black, graphite, graphene, fullerene, carbon nanotubes (CNT), carbon nanohorns (CNH) and mixtures thereof.
  • carbon black, graphite and/or graphene is particularly preferred.
  • the synergist (D) is present in the compositions according to the invention in a proportion of 0.01 to 10% by weight, preferably 0.05 to 5% by weight, based on the total weight of components (A) to (E). Dimensions.
  • the masses described can also contain optional components as further additives (E).
  • the additives (E) are preferably selected from the group consisting of fillers, dyes, pigments, aging inhibitors, fluorescent agents, polymerization accelerators, sensitizers, adhesion promoters, drying agents, crosslinking agents, flow improvers, wetting agents, thixotropic agents, diluents, flexibilizers, polymeric thickeners, flame retardants, corrosion inhibitors, plasticizers and tackyfier and combinations thereof.
  • the additives (E) can be present in the compositions according to the invention in a proportion of 0 to 85% by weight, preferably 1 to 65% by weight, based on the total weight of the composition.
  • thermosetting composition according to the invention formed from the components (A) to (E) described above, can be used alone or together with other reactive resin compositions.
  • the chemical structure and composition of the other reactive resin masses are not further restricted.
  • the further reactive resin compositions can comprise, as reactive components, additional reactive resins (F), curing agents (G) and/or initiators (H) for the polymerization or crosslinking of the additional reactive resins (F).
  • the other reactive resin compositions present in a mixture with the inventive thermosetting composition of components (A) to (E) can then be fixed in a dimensionally stable state by heating to activate the inventive thermosetting composition at low temperature and fed to further treatment steps.
  • component (F) for example, at least one cationically polymerizable or addition-crosslinking compound can be used, which is selected from the group of epoxide-containing compounds (F1), oxetanes (F2) and vinyl ethers (F3) and combinations thereof.
  • monofunctional epoxides can also be used as reactive diluents.
  • epoxide-containing compounds of which at least one is difunctional or higher.
  • oxetanes bis(1-ethyl-3-oxetanylmethyl)ether (DOX), 3-allyloxymethyl-3-ethyloxetane (AQX), 3-ethyl-3-[(phenoxy)methyloxetane (POX), 3-ethyl-3-hydroxymethyl-oxetanes (OXA), 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene (XDO), 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane (EHOX).
  • DOX 1-ethyl-3-oxetanylmethyl)ether
  • AQX 3-allyloxymethyl-3-ethyloxetane
  • POX 3-ethyl-3-[(phenoxy)methyloxetane
  • OXA 3-ethyl-3-hydroxymethyl-oxetanes
  • XDO 1,4-bis[(
  • the additional reactive resins preferably include one or more at least difunctional vinyl ethers. "At least difunctional" means here that the vinyl ether contains at least two vinyl groups.
  • the addition-crosslinking reactive resin compositions preferably contain no initiator (H) for cationic polymerization.
  • Photoinitiators based on diaryliodonium which are commercially available as photolatent acids include those available under the trade names LIV1242 or LIV2257 from Deuteron and Bluesil 2074 from Bluestar.
  • an additional reactive resin (F) comprising at least one difunctional epoxide-containing compound (F1) selected from the group of cycloaliphatic epoxides, aliphatic and/or aromatic glycidyl ethers; and
  • thermosetting composition with components (A) to (E) in the formulation is from 10 to 90% by weight and the proportion of the cationically polymerizable reactive resin composition from components (F) and (H) is from 10 to 90% by weight .-% amounts to.
  • compositions can be cured within a short time at a temperature of below 100° C., preferably below 90° C., more preferably below 80° C.
  • the masses are fully cured within less than 5 minutes at a temperature of 100 °C, within less than 15 minutes at 90 °C and within less than 30 minutes at 80 °C. Curing at 60 °C is also possible.
  • the heat-curing mass is used in a method for joining, casting or coating substrates, the method comprising the following steps: a) providing the mass according to the invention; b) dispensing the mass onto a first substrate; c) selectively supplying a second substrate to the mass; d) optionally fixing the composition by exposure to actinic radiation; and e) heating the mass and the substrate and/or the substrate composite to a temperature of 60 to 100° C. for 5 to 60 minutes, with the mass curing.
  • Room temperature is defined as 23 ⁇ 2 °C.
  • the viscosity was measured using a Physica MCR302 rheometer from Anton Paar with a standardized measuring cone PP20 at 23° C. with a 200 ⁇ m gap and determined at a shear rate of 10/second.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention se rapporte à une masse thermodurcissable, la masse comprenant les constituants suivants : (A) au moins un composé durcissable par durcissement radicalaire, le composé durcissable par durcissement radicalaire comprenant au moins un (méth)acrylate, (B) au moins un amorceur radicalaire à base d'un composé peroxo, le composé peroxo comprenant au moins un peroxodicarbonate, (C) au moins un stabilisant comprenant au moins un phénol à empêchement stérique et (D) au moins un synergiste à base d'un polymorphe du carbone ayant des liaisons carbone-carbone insaturées.
EP22758433.1A 2021-09-03 2022-07-26 Masse thermodurcissable à base de (méth)acrylates et de peroxodicarbonates Pending EP4396301A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102021122835.2A DE102021122835A1 (de) 2021-09-03 2021-09-03 Warmhärtende Masse auf Basis von (Meth)Acrylaten und Peroxodicarbonaten
PCT/EP2022/070914 WO2023030763A1 (fr) 2021-09-03 2022-07-26 Masse thermodurcissable à base de (méth)acrylates et de peroxodicarbonates

Publications (1)

Publication Number Publication Date
EP4396301A1 true EP4396301A1 (fr) 2024-07-10

Family

ID=83059373

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22758433.1A Pending EP4396301A1 (fr) 2021-09-03 2022-07-26 Masse thermodurcissable à base de (méth)acrylates et de peroxodicarbonates

Country Status (5)

Country Link
EP (1) EP4396301A1 (fr)
KR (1) KR20240054336A (fr)
CN (1) CN117897461A (fr)
DE (1) DE102021122835A1 (fr)
WO (1) WO2023030763A1 (fr)

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5089536A (en) 1982-11-22 1992-02-18 Minnesota Mining And Manufacturing Company Energy polmerizable compositions containing organometallic initiators
JPH0689052B2 (ja) 1985-10-30 1994-11-09 アクゾ・ナ−ムロ−ゼ・フエンノ−トシヤツプ 安定化パ−オキシジカ−ボネ−ト組成物
DE3616176A1 (de) 1986-05-14 1987-11-19 Roehm Gmbh Verfahren zur herstellung einer kratzfesten und witterungsbestaendigen beschichtung auf einem formkoerper
US5070161A (en) 1988-05-27 1991-12-03 Nippon Paint Co., Ltd. Heat-latent, cationic polymerization initiator and resin compositions containing same
US5548046A (en) 1994-02-16 1996-08-20 Elf Atochem North America, Inc. Stabilized dialkyl peroxydicarbonate compositions and their uses
DE10131147A1 (de) 2001-06-28 2003-01-16 Peroxid Chemie Gmbh & Co Kg Stabilisierte Peroxidicarbonatzubereitung
US6893584B2 (en) 2003-04-25 2005-05-17 Crompton Corporation Stabilized organic peroxide composition and process for making the same
US20050215713A1 (en) 2004-03-26 2005-09-29 Hessell Edward T Method of producing a crosslinked coating in the manufacture of integrated circuits
WO2015200706A1 (fr) 2014-06-25 2015-12-30 Rensselaer Polytechnic Institute Polymères d'oxétane et leurs procédés de préparation
KR102396869B1 (ko) 2016-09-06 2022-05-10 가부시끼가이샤 쓰리본드 열경화형 도전성 접착제
US10968367B2 (en) 2016-11-08 2021-04-06 H.B. Fuller Company Low temperature curable adhesive composition and articles including the same
KR102149045B1 (ko) * 2017-02-22 2020-08-28 주식회사 엘지화학 접착제 조성물
EP3401928B1 (fr) * 2017-05-09 2021-08-18 Henkel AG & Co. KGaA Adhésif électriquement conducteur pour fixer des cellules solaires
WO2019043778A1 (fr) 2017-08-29 2019-03-07 三菱重工業株式会社 Composition durcissable, matériau de pâte durcissable, matériau de feuille durcissable, matériau durcissable de fabrication de moule, procédé de durcissement, et objet durci
EP3848179A1 (fr) * 2020-01-10 2021-07-14 Carl Zeiss Vision International GmbH Procédé à jet d'encre pour fabriquer un verre de lunettes
KR102144075B1 (ko) * 2020-06-05 2020-08-12 주식회사 아이델 태양전지가 적용된 방음터널용 패널

Also Published As

Publication number Publication date
CN117897461A (zh) 2024-04-16
WO2023030763A1 (fr) 2023-03-09
KR20240054336A (ko) 2024-04-25
DE102021122835A1 (de) 2023-03-09

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