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
  • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(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
  • C08F220/38—Esters containing sulfur
• • 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
• • 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
  • C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

Definitions

• composition of this disclosure relates to a composition containing a specific compound and a cured product obtained by curing the composition.
• the composition of this disclosure can be used for applications such as surface coating agents, paints, adhesives, and self-repairing materials.
• Polymer materials exhibit high mechanical strength and durability based on strong covalent bonds, but they are poorly reprocessable and reusable, and it is difficult to repair scratches or breaks, especially to self-repair.
• Patent Documents 1 to 3 have problems such as the need for complicated processes to manufacture the material, and the methods of Patent Documents 4 and 5 have problems such as limitations on the number of times self-repair can be performed due to the blending amount of microcapsules, etc.
• self-repairing materials that apply an external stimulus to a material using dynamic covalent bonds and use reversible bond dissociation-recombination have been known (see, for example, Patent Document 6 and Non-Patent Document 1).
• the materials containing these self-repairing materials described in patent documents, etc. do not have sufficient self-repairing properties.
• the present disclosure has therefore been made in consideration of the above problems and circumstances, and aims to provide a material with excellent self-repairing properties.
• the present disclosure is a composition characterized by containing (A) one or more compounds selected from the group of compounds represented by general formula (1) and compounds represented by general formula (2), (B) one or more compounds selected from the group of methacrylate compounds and acrylate compounds different from the above (A), and (C) a photoradical initiator.
• R 11 and R 12 each independently represent a hydrogen atom or a methyl group
• X 11 and X 12 each independently represent a direct bond, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the aliphatic hydrocarbon group in which one or more methylene groups have been replaced with a divalent group selected from the following Group I-1.
• one or more hydrogen atoms in the aliphatic hydrocarbon group having the above substituent are replaced with an atom or group selected from the following Group II-1.
• Group I-1 --O--, --COO--, --OCO--, --CO--CO--, --CO--CO--O--, --CS--, --S--, --SO--, --SO 2 --, --NR'--, --NR'--CO--, --CO--NR'--, --NR'--COO--, --OCO--NR'-- or --SiR'R"--.
• R' and R" each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group, and when a plurality of R' or R" are present, they may be the same or different.
• n1 is an integer from 1 to
• Group I-2 --O--, --COO--, --OCO--, --CO--CO--, --CO--CO--O--, --CS--, --S--, --SO--, --SO 2 --, --NR'--, --NR'--CO--, --CO--NR'--, --NR'--COO--, --OCO--NR'-- or --SiR'R"--.
• R' and R" each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group, and when a plurality of R' or R" are present, they may be the same or different.
• at least one of R 21 and R 22 represents a group represented by the following general formula (2-1)
• at least one of R 23 and R 24 represents a group represented by the following general formula (2-1).
• n2 is an integer from 1 to 10.
• R 31 represents a hydrogen atom or a methyl group
• L 31 represents a direct bond or an aliphatic hydrocarbon group having 1 to 20 carbon atoms
• L 32 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• n3 represents an integer of 0 to 5. When n3 is an integer of 2 or more, multiple L 32 may be the same group or different groups. * represents the bonding position with the nitrogen atom in general formula (2).
• the above (A) is a compound represented by general formula (1).
• the above (B) is one or more selected from the group consisting of bifunctional methacrylate compounds, trifunctional or higher polyfunctional methacrylate compounds, bifunctional acrylate compounds, and trifunctional or higher polyfunctional acrylate compounds.
• the present disclosure relates to a cured product obtained by curing the above composition with energy rays.
• the cured product is preferably used for coating film applications.
• This disclosure makes it possible to provide a material with excellent self-repairing properties.
• composition of the present disclosure is characterized by containing (A) one or more selected from the group of compounds represented by general formula (1) and compounds represented by general formula (2), (B) one or more selected from the group of methacrylate compounds and acrylate compounds different from the above (A), and (C) a photoradical initiator.
• the composition of the present disclosure may contain only the compound represented by general formula (1), may contain only the compound represented by general formula (2), or may contain both the compound represented by general formula (1) and the compound represented by general formula (2).
• the composition of the present disclosure can easily form a composition with excellent self-repairing properties by containing the above-mentioned specified compound.
• the content of (A) is not particularly limited, but is preferably 1 to 80 parts by mass, more preferably 1 to 60 parts by mass, and even more preferably 5 to 40 parts by mass, relative to a total of 100 parts by mass of (A) one or more selected from the group of compounds represented by general formula (1) and compounds represented by general formula (2), and (B) one or more selected from the group of methacrylate compounds and acrylate compounds different from the above (A).
• the content of (A) is within the above range, the composition of the present disclosure can easily form one having excellent self-repairing properties.
• R 11 and R 12 each independently represent a hydrogen atom or a methyl group.
• X11 and X12 each independently represent a direct bond, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or the aliphatic hydrocarbon group in which one or more methylene groups have been replaced with a divalent group selected from the following Group I-1.
• One or more hydrogen atoms in the aliphatic hydrocarbon group having the above substituent are replaced with an atom or group selected from the following Group II-1.
• R 11 and R 12 are preferably methyl groups, because the composition of the present disclosure can be easily formed to have excellent self-repairing properties.
• examples of the halogen atom in group II-1 represented by X 11 and X 12 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• X 11 and X 12 are groups in which one or more methylene groups in the above-mentioned aliphatic hydrocarbon group are replaced with a divalent group selected from group I-1
• the group replaced with a divalent group selected from group I-1 is preferably -O-, -CO-NH-, or -NH-CO-, because the composition of the present disclosure can easily be formed into one having excellent self-repairing properties.
• the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R 21 , R 22 , R 23 , and R 24 in general formula (2) may be any group that does not contain an aromatic hydrocarbon ring or a heterocycle, and examples thereof include alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkylalkyl groups having 4 to 20 carbon atoms, and groups in which one or more hydrogen atoms of these groups are substituted with the substituents described below.
• L 31 is preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms, and more preferably an aliphatic hydrocarbon group having 1 to 5 carbon atoms, because the composition of the present disclosure can easily be formed with excellent self-repairing properties.
• the bifunctional methacrylate compound, the trifunctional or higher polyfunctional methacrylate compound, the bifunctional acrylate compound, and the trifunctional or higher polyfunctional acrylate compound are preferably compounds that contain a urethane bond in the molecule, i.e., compounds that have a urethane bond and a methacryl group or an acrylic group in the same molecule (hereinafter, these may be referred to as a urethane methacrylate compound and a urethane acrylate compound, respectively).
• a urethane methacrylate compound and a urethane acrylate compound are preferably compounds that contain a urethane bond in the molecule, i.e., compounds that have a urethane bond and a methacryl group or an acrylic group in the same molecule (hereinafter, these may be referred to as a urethane methacrylate compound and a urethane acrylate compound, respectively).
• the cumulative dose may be appropriately changed depending on the thickness of the object, but if the cumulative dose is insufficient, the curing reaction may not proceed sufficiently, and if the cumulative dose is too large, the object may be colored.
• the cumulative dose is preferably in the range of 1 mJ/cm 2 to 100,000 mJ/cm 2 .
• a composition comprising: (A) one or more compounds selected from the group consisting of compounds represented by general formula (1) and compounds represented by general formula (2); (B) one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds different from (A); and (C) a photoradical initiator.
• R' and R" each independently represent a hydrogen atom or an unsubstituted aliphatic hydrocarbon group, and when a plurality of R' or R" are present, they may be the same or different.
• at least one of R 21 and R 22 represents a group represented by the following general formula (2-1)
• at least one of R 23 and R 24 represents a group represented by the following general formula (2-1).
• n2 is an integer from 1 to 10.
• R 31 represents a hydrogen atom or a methyl group
• L 31 represents a direct bond or an aliphatic hydrocarbon group having 1 to 20 carbon atoms
• L 32 represents an aliphatic hydrocarbon group having 1 to 5 carbon atoms.
• n3 represents an integer of 0 to 5. When n3 is an integer of 2 or more, multiple L 32 may be the same group or different groups.
• * represents the bonding position with the nitrogen atom in general formula (2).
• Example ⁇ Each composition obtained by mixing the components of the Examples and Comparative Examples shown in Tables 1 and 2 was applied onto a substrate (easy-adhesion treated PET film, Toyobo Co., Ltd., Cosmoshine A4360, thickness 100 ⁇ m) using a #8 bar coater, and the solvent was removed by drying in an oven at 80°C for 1 minute. After that, irradiation with 250 mJ/ cm2 was carried out twice using a belt conveyor type high pressure mercury lamp line without using a mask, to produce each sample coating.
• the blend amounts in the tables indicate parts by mass of each component.
• A1 Compound No. 1-1 prepared by the method described in Preparation Example 1
• A2 Compound No. 2-1 prepared by the method described in Preparation Example 2
• A3 Compound No. 1-8 prepared by the method described in Preparation Example 3
• B1 Urethane acrylate (UN-333 (manufactured by Negami Chemical Industries, Ltd.), functional group number 2, polyester type, weight average molecular weight (Mw) 5000)
• B3 Urethane acrylate (UN-2601 (manufactured by Negami Chemical Industries, Ltd.), functional group number 2, adduct-type urethane acrylate, weight average molecular weight (Mw) 1600)
• B4 Urethane acrylate (UN-2310 (manufactured by Negami Chemical Industries
• composition disclosed herein can produce a material with excellent self-repairing properties.

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• 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)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Indole Compounds (AREA)

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Citations (5)

• 2023
  • 2023-12-19 WO PCT/JP2023/045535 patent/WO2024143072A1/ja not_active Ceased
  • 2023-12-19 JP JP2024567660A patent/JPWO2024143072A1/ja active Pending
  • 2023-12-27 TW TW112150977A patent/TW202432616A/zh unknown

Patent Citations (5)

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