WO2020032056A1 - Composition durcissable contenant un monomère de polypseudorotaxane - Google Patents

Composition durcissable contenant un monomère de polypseudorotaxane Download PDF

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Publication number
WO2020032056A1
WO2020032056A1 PCT/JP2019/030960 JP2019030960W WO2020032056A1 WO 2020032056 A1 WO2020032056 A1 WO 2020032056A1 JP 2019030960 W JP2019030960 W JP 2019030960W WO 2020032056 A1 WO2020032056 A1 WO 2020032056A1
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group
monomer
molecule
polypseudorotaxane
curable composition
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PCT/JP2019/030960
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English (en)
Japanese (ja)
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康智 清水
川崎　剛美
誉夫 野口
光喜 戸知
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株式会社トクヤマ
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B24—GRINDING; POLISHING
    • B24B—MACHINES, DEVICES, OR PROCESSES FOR GRINDING OR POLISHING; DRESSING OR CONDITIONING OF ABRADING SURFACES; FEEDING OF GRINDING, POLISHING, OR LAPPING AGENTS
    • B24B37/00—Lapping machines or devices; Accessories
    • B24B37/11—Lapping tools
    • B24B37/20—Lapping pads for working plane surfaces
    • B24B37/24—Lapping pads for working plane surfaces characterised by the composition or properties of the pad materials
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/23—Photochromic filters
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting

Definitions

  • the polyrotaxane has a cyclic molecule, and a linear molecule (axial molecule) penetrating the cyclic molecule in a skewered manner, and is disposed at both ends of the axial molecule to separate (eliminate) the cyclic molecule from the axial molecule. ) And a bulky group (blocking group) for preventing the compound molecule.
  • polypseudorotaxane has a cyclic molecule, and is composed of a linear molecule (axial molecule) penetrating the cyclic molecule in a skewered manner, and at least one of the terminal of the linear molecule has a bulky group. Have no complex molecular structure.
  • a method of generally supplying a slurry (polishing liquid) in which abrasive grains are dispersed in an alkali solution or an acid solution during polishing is generally employed. That is, the object to be polished is flattened by the mechanical action by the abrasive grains in the slurry and the chemical action by the alkali solution or the acid solution.
  • the slurry is supplied to the surface of the object to be polished, and the surface of the object to be polished is planarized by sliding the polishing pad material into contact with the surface.
  • Patent Document 6 As a material of such a polishing pad, an abrasive obtained from a urethane-based curable composition is known (see Patent Document 5). Recently, a polishing pad using polyrotaxane has been disclosed (see Patent Document 6). In Patent Document 6, by incorporating a polyrotaxane structure into a urethane resin, not only good wear resistance but also excellent polishing characteristics (high polishing rate, low scratch property, and high flatness) are exhibited.
  • polyrotaxane monomers exhibit excellent properties by reacting with other polymerizable monomers to form a cured product (polymer).
  • polymer polymerizable monomers
  • Non-patent Document 1 a method is known in which a polyrotaxane composed of 2-hydroxypropyl- ⁇ -cyclodextrin and a copolymer of polyethylene glycol and polypropylene glycol is converted into a polyrotaxane by the One-Pot method (Non-patent Document 1). ).
  • polyrotaxane monomers are capable of imparting excellent functions to cured products (polymers) using the same, and have been studied in various fields.
  • the curable composition of the present invention contains a polypseudorotaxane monomer.
  • the polypseudorotaxane monomer does not need to introduce a bulky group into the terminal of the shaft molecule as compared with a conventionally used polyrotaxane monomer. Therefore, the manufacturing process can be simplified and the number of reagents can be reduced, so that cost and production efficiency can be improved. As a result, the curable composition containing the polypseudorotaxane monomer is industrially very effective.
  • the polypseudorotaxane monomer may have a polymerizable group at a terminal of the axis molecule.
  • the polymerizable functional group does not need to be a sufficiently bulky group that can prevent the cyclic molecule from detaching from the axial molecule. If a polymerizable group has been introduced into the shaft molecule, the shaft molecule can be introduced into a polymer chain forming a matrix by reacting with another polymerizable monomer. And the obtained hardened
  • the curable composition of the present invention has a complex molecular structure consisting of a cyclic molecule having a polymerizable functional group and a shaft molecule penetrating through the ring of the cyclic molecule, and has no bulky group at at least one end of the shaft molecule ( A) a polypseudorotaxane monomer, and The curable composition contains (B) a polymerizable monomer other than the (A) polypseudorotaxane monomer.
  • Glycol polyvinyl acetal, polyvinyl methyl ether, polyamine, polyethylene imine, casein, gelatin, starch, olefin resin (polyethylene, polypropylene, etc.), polyester, polyvinyl chloride, styrene resin (polystyrene, acrylonitrile-styrene copolymer resin, etc.) , Acrylic resin (poly (meth) acrylate acid, polymethyl methacrylate Polymethyl acrylate, acrylonitrile-methyl acrylate copolymer resin), polycarbonate, polyurethane, vinyl chloride-vinyl acetate copolymer resin, polyvinyl butyral, polyisobutylene, polytetrahydrofuran, polyaniline, acrylonitrile-butadiene-styrene copolymer (ABS resin) , Polyamide (such as nylon), polyimide, polydiene (such as polyisoprene and polybutadiene
  • those suitable as a polymer forming an axis molecule include polyethylene glycol, polypropylene glycol, polytetramethylene ether glycol, polyisoprene, polyisobutylene, polybutadiene, polypropylene glycol, and poly (ethylene glycol). Tetrahydrofuran, polydimethylsiloxane, polyethylene, polypropylene, polyvinyl alcohol or polyvinyl methyl ether.
  • the axis molecule is more preferably a copolymer obtained by polymerizing a plurality of monomers.
  • the most preferably used axial molecule preferably includes at least part of a site having a structure represented by the following formula (I).
  • R 14 , R 15 , and R 16 are each a linear or branched alkylene group having 2 to 20 carbon atoms; i, j, and k indicate the degree of polymerization (each repeating unit), and are each an integer of 1 to 200.
  • R 14 , R 15 , and R 16 may be the same group or different groups. Among them, it is preferable that the number of carbon atoms of R 15 be larger than the number of carbon atoms of R 14 and R 16 from the viewpoint that the cyclic molecule is less likely to be eliminated. In this case, R 14 and R 16 may have the same carbon number. Specifically, R 14 is an ethylene group having 2 carbon atoms, R 15 is a propylene group having 3 carbon atoms, or a trimethylene group, and R 16 is a group such as an ethylene group having 2 carbon atoms. It is preferable that the relationship be established.
  • the structure of the formula (I) may be present at one position or at a plurality of positions in the axis molecule.
  • the axis molecule itself has the structure of the formula (I). Is preferred.
  • the weight average molecular weight Mw of the shaft molecule is preferably from 400 to 100,000, particularly preferably from 1,000 to 50,000, particularly preferably from 2,000 to 30,000.
  • this weight average molecular weight Mw is a value measured by the GPC measurement method described in the following Examples.
  • the cyclic molecule (A) of the polypseudorotaxane monomer may be any as long as it has a ring having a size that can include the above-mentioned axial molecule.
  • a ring include a cyclodextrin ring, a crown ether ring, a benzocrown ring, a dibenzocrown ring, and a dicyclohexanocrown ring.
  • a cyclodextrin ring is particularly preferred.
  • the maximum number of inclusions of a cyclic molecule with respect to one axial molecule can be calculated from the length of the axial molecule and the thickness of the ring of the cyclic molecule.
  • the maximum inclusion number is calculated as follows. That is, the two repeating units [—CH (CH 3 ) —CH 2 O—] of polypropylene glycol approximate the thickness of one ⁇ -cyclodextrin ring.
  • Lactone compounds 4-membered ring lactones, for example, ⁇ -propiolactone, ⁇ -methylpropiolactone, L-serine- ⁇ -lactone and the like.
  • 5-membered ring lactones for example, ⁇ -butyrolactone, ⁇ -hexanolactone, ⁇ -heptanolactone, ⁇ -octanolactone, ⁇ -decanolactone, ⁇ -dodecanolactone, ⁇ -hexyl- ⁇ -butyrolactone, ⁇ -heptyl - ⁇ -butyrolactone, ⁇ -hydroxy- ⁇ -butyrolactone, ⁇ -methyl- ⁇ -decanolactone, ⁇ -methylene- ⁇ -butyrolactone, ⁇ , ⁇ -dimethyl- ⁇ -butyrolactone, D-erythronolactone, ⁇ -methyl- ⁇ -Butyrolactone, ⁇ -nonanolactone, DL-pantolactone, ⁇ -phenyl- ⁇ -butyrolactone, ⁇ -undecanolactone, ⁇ -valerolactone, 2,2-pentamethylene-1,3-dioxolan
  • 6-membered ring lactones for example, ⁇ -valerolactone, ⁇ -hexanolactone, ⁇ -octanolactone, ⁇ -nonanolactone, ⁇ -decanolactone, ⁇ -undecanolactone, ⁇ -dodecanolactone, ⁇ -tridecanolactone, ⁇ -tetradecanolactone, DL-mevalonolactone, 4-hydroxy-1-cyclohexanecarboxylic acid ⁇ -lactone, monomethyl- ⁇ -valerolactone, monoethyl- ⁇ -valerolactone, monohexyl- ⁇ -valerolactone, 1,4-dioxane -2-one, 1,5-dioxepan-2-one and the like.
  • the side chain-introducing compound preferably used is 1,2-propylene oxide, ⁇ -caprolactone, ⁇ -acetyl- ⁇ -butyrolactone, ⁇ -methyl- ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -butyrolactone, or the like. Is particularly preferred, and most preferred are 1,2-propylene oxide and ⁇ -caprolactone.
  • a side chain When a side chain is introduced into a cyclic molecule using a radical polymerizable compound, if the radical polymerizable compound has another functional group, the side chain has a group having the functional group as it is. Will be. Even when only the radical polymerizable group is present in the side chain, after forming the side chain with the radical polymerizable compound, a part of the side chain may be modified with a group having a functional group other than the radical polymerizable group. For example, a functional group other than the radical polymerizable group can be introduced into the side chain.
  • the polymerizable functional group of the cyclic molecule is not particularly limited as long as it is a group capable of polymerizing with a polymerizable monomer other than the polypseudorotaxane monomer.
  • a hydroxyl group, a thiol group, an amino group, a carboxyl group, a (meth) acrylate group, or an allyl group preferred are a hydroxyl group and a (meth) acrylate group.
  • the polymerizable functional group is, depending on the case, the one possessed by the above-described cyclic molecule or the one introduced using the above-mentioned side chain. Among them, in consideration of the reactivity, it is preferable that the terminal of the side chain be a polymerizable functional group, and that two or more be present.
  • the upper limit of the number of the polymerizable functional groups is not particularly limited, but the number of moles of the polymerizable functional groups introduced into the terminal of the side chain is determined based on the weight average molecular weight of the (A) polypseudorotaxane monomer. On the other hand, the number is 10 mmol / g.
  • the iso (thio) cyanate compound is a monomer having at least one type of isocyanate group or isothiocyanate group.
  • a monomer having two groups of an isocyanate group and an iso (thio) cyanate group is also selected.
  • compounds having 2 to 6 iso (thio) cyanate groups in the molecule are preferable, compounds having 2 to 4 are more preferable, and compounds having 2 are more preferable.
  • the (B1) iso (thio) cyanate compound is prepared by reacting a bifunctional polyiso (thio) cyanate compound described below with a bifunctional poly (thio) ol compound (B12) urethane prepolymer (B12).
  • B12 bifunctional poly (thio) ol compound
  • (B12) component it may be simply referred to as “(B12) urethane prepolymer” or “(B12) component”.
  • the urethane prepolymer (B12) corresponding to the iso (thio) cyanate compound one generally used containing an unreacted iso (thio) cyanate group can be used in the present invention without any limitation.
  • Alicyclic isocyanate; component (B1) isophorone diisocyanate, (bicyclo [2.2.1] heptane-2,5-diyl) bismethylene diisocyanate, (bicyclo [2.2.1] heptane-2,6-diyl) Bismethylene diisocyanate, 2 ⁇ , 5 ⁇ -bis (isocyanate) norbornane, 2 ⁇ , 5 ⁇ -bis (isocyanate) norbornane, 2 ⁇ , 6 ⁇ -bis (isocyanate) norbornane, 2 ⁇ , 6 ⁇ -bis (isocyanate) norbornane, 2,6-di ( Isocyanatomethyl) furan, 1,3-bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane-4,4′-diisocyanate, 4,4-isopropylidenebis (cyclohexylisocyanate), cyclohexanediisocyanate, methyl
  • urethane prepolymer (B12) obtained by reacting the (B13) bifunctional polyiso (thio) cyanate group-containing monomer with the (B32) bifunctional poly (thio) ol described below is used as the (B1) It can also be used as a polyiso (thio) cyanate monomer.
  • the (B12) urethane prepolymer is obtained by reacting the (B13) bifunctional polyiso (thio) cyanate group-containing monomer with the number of moles (n5) of iso (thio) cyanate groups and the active hydrogen of (B32) bifunctional poly (thio) ol. It is preferable that the number of moles of the group having the formula (n6) is within the range of 1 ⁇ (n5) / (n6) ⁇ 2.3.
  • the number of moles (n5) of the iso (thio) cyanate group is determined by the number of (B13) bifunctional polyiso (thio) cyanate group-containing monomers. Is the total number of moles of iso (thio) cyanate groups.
  • the number of moles (n6) of the group having an active hydrogen is determined by the total activity of the (B32) bifunctional poly (thio) ol. It is the number of moles of hydrogen.
  • the equivalent of the iso (thio) cyanate is preferably 300 to 5,000. That is, the average iso (thio) cyanate equivalent in the (B1) iso (thio) cyanate compound comprising the (B12) urethane prepolymer and the (B13) bifunctional polyiso (thio) cyanate group-containing monomer is 300 to 5000. Preferably. When the average iso (thio) cyanate equivalent is 300 to 5000, a polyiso (thio) cyanate compound having a certain molecular weight is used, and it is considered that an excellent effect is exhibited.
  • the method for producing a prepolymer used in the present invention is characterized in that (B32) 2 having two active hydrogen groups in the molecule and (B13) 2 having two functional poly (thio) ol and iso (thio) cyanate groups in the molecule.
  • the urethane prepolymer (B12) having an iso (thio) cyanate group at the terminal of the molecule may be produced.
  • There is no limitation as long as a prepolymer having an iso (thio) cyanate group at a terminal can be obtained.
  • it can be produced by heating or adding a urethanization catalyst as necessary.
  • Such epoxy compounds are roughly classified into aliphatic epoxy compounds, alicyclic epoxy monomers, and aromatic epoxy monomers, and preferred examples thereof are described in WO 2015/068798. Can be used.
  • the (thio) ol compound is a monomer having at least one group selected from the group consisting of an OH group and an SH group in one molecule.
  • a monomer having two groups, an OH group and an SH group is also selected.
  • the (thio) ol compounds can be roughly classified into aliphatic alcohols, alicyclic alcohols, aromatic alcohols, polyester polyols, polyether polyols, polycaprolactone polyols, polycarbonate polyols, polyacryl polyols, thiols, and OH / SH types. It is classified as a polymerizable group-containing monomer. The following are specific examples.
  • Polyester polyol; (B3) component A compound obtained by a condensation reaction between a polyol and a polybasic acid is exemplified.
  • the number average molecular weight is preferably from 400 to 2,000, more preferably from 500 to 1500, and most preferably from 600 to 1200.
  • Those having hydroxyl groups only at both ends of the molecule (two in the molecule) correspond to the (B32) bifunctional poly (thio) ol constituting the (B12) urethane prepolymer.
  • the number average molecular weight is preferably from 400 to 2,000, more preferably from 500 to 1500, and most preferably from 600 to 1200.
  • Those having hydroxyl groups only at both ends of the molecule (two in the molecule) correspond to the (B32) bifunctional poly (thio) ol constituting the (B12) urethane prepolymer.
  • Polyacrylic polyol; component (B3) a polyol compound obtained by polymerizing a (meth) acrylate ester or a vinyl monomer. Those having hydroxyl groups only at both ends of the molecule (two in the molecule) correspond to the (B32) bifunctional poly (thio) ol constituting the (B12) urethane prepolymer.
  • Thiol As a preferable specific example of the thiol, those described in International Publication WO2015 / 068798 can be used. Among them, the following can be mentioned as examples of particularly preferable ones.
  • component (B3) 2-mercaptoethanol, 1-hydroxy-4-mercaptocyclohexane, 2-mercaptohydroquinone, 4-mercaptophenol, 1-hydroxyethylthio-3-mercaptoethylthiobenzene , 4-hydroxy-4'-mercaptodiphenylsulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethylsulfide mono (3-mercaptopropionate), dimercaptoethane mono (sulfylate) (the (B12) urethane press (Corresponds to (B32) bifunctional poly (thio) ol constituting the polymer).
  • Curable composition containing component (B1), component (B2), component (B3), and component (B4)
  • component (B1), component (B2), component (B3), and component (B4) In other words, when the curable composition contains (A), the polymerizable functional group in the polypseudorotaxane monomer is not a radical polymerizable group, but is polymerized and cured by a polycondensation or polyaddition reaction to produce a cured product. Is preferably set to the following compounding ratio.
  • the total amount of the component (B1), the component (B2), the component (B3), and the component (B4) (hereinafter, sometimes simply referred to as “the total amount of the component (B)”), and ( It is preferable that the component (A) is contained in an amount of 3 to 50 parts by mass and the total amount of the component (B) is contained in an amount of 50 to 97 parts by mass based on 100 parts by mass in total with the component (A).
  • the polypseudorotaxane monomer in this ratio, the obtained cured product can exhibit excellent polishing characteristics and mechanical characteristics when it is a polishing pad.
  • radical polymerizable monomer (B5) radical polymerizable monomer> (B5)
  • the radically polymerizable monomer (hereinafter sometimes simply referred to as the component (B5)) is not particularly limited as long as it has a radically polymerizable group. Radical polymerizable monomers can be broadly classified into (meth) acrylate compounds having a (meth) acrylate group, vinyl compounds having a vinyl group, and allyl compounds having an allyl group.
  • the polymerizable monomer represented by the above formula (3) is usually obtained in the form of a mixture of molecules having different molecular weights. Therefore, e and f are shown as average values.
  • the silselquioxane monomer has various molecular structures such as cage, ladder, and random, and is radically polymerizable such as (meth) acrylate group. Monomers having groups are preferred.
  • silselquioxane compounds include those represented by the following formula (5).
  • a composite polymerizable compound having a plurality of different types of polymerizable groups in the molecule can also be used.
  • specific compounds include the following.
  • the compound falls under this classification.
  • polymerizable monomers can be used without any limitation.
  • episulfide monomers, thietanyl monomers, and mono (thio) ol monomers can also be used.
  • episulfide monomer, the thietanyl monomer, and the mono (thio) ol monomer those described in International Publication No. WO2015 / 068798 can be used.
  • the polymerizable monomer other than (A) the polypseudorotaxane monomer and (B) the polymerizable monomer other than the polypseudorotaxane may be appropriately selected depending on the intended use.
  • the polymerizable functional group of the cyclic molecule of the polypseudorotaxane monomer is an OH group or an SH group
  • the (B3) (thio) ol compound Is preferably used in combination By doing so, excellent mechanical properties and photochromic properties can be exhibited.
  • the (B1) iso (thia) cyanate compound is used as the polymerizable monomer (B).
  • polymerization accelerators (C1) to (C5) that can be suitably used in the present invention, those described in International Publication No. WO2015 / 068798 can be used as specific examples.
  • each of these various (C) polymerization curing accelerators can be used alone or in combination of two or more.
  • the amount used may be a so-called catalyst amount.
  • (A) polypseudorotaxane and The amount may be a small amount in the range of 0.001 to 10 parts by mass, particularly 0.01 to 5 parts by mass, per 100 parts by mass of the polymerizable monomer (B) in total.
  • Each of these various (D) photochromic compounds can be used alone or in combination of two or more.
  • the amount used may be appropriately determined according to the intended use. For example, 0.001 to 20 parts by mass, particularly 0.01 to 100 parts by mass per 100 parts by mass of the total of (A) the polypseudorotaxane and (B) the polymerizable monomer. It is preferably in the range of 10 parts by mass.
  • a known polymerization method can be adopted.
  • the conditions described in WO 2015/068798, WO 2016/143910, and JP-A-2017-48305 can be employed.
  • the conditions described in WO2014 / 136804 and WO2015 / 068798 can be employed.
  • a photochromic cured body can be produced by polymerizing and curing as it is.
  • the cured product obtained by curing the curable composition of the present invention may have pores in the cured product depending on the use.
  • a polishing pad is known.
  • a known and known foaming method or the like can be used without any limitation. Examples of these methods include a method of dispersing and hardening a volatile foaming agent such as a low-boiling hydrocarbon or the like, and a method of dispersing and hardening a minute hollow body (microballoon). Or a mechanical floss foaming method in which an inert gas such as air or nitrogen is blown during mixing.
  • the cured product of the curable composition of the present invention When the cured product of the curable composition of the present invention is used for a polishing pad or the like, the cured product preferably contains hollow particles such as the above-described minute hollow body (microballoon). That is, it is preferable that a curable composition containing hollow particles is polymerized and cured to produce a cured product containing hollow particles.
  • the matrix resin in the cured product is preferably a urethane resin, and as the curable composition for obtaining the cured product, a curable composition capable of forming a urethane resin is preferably used.
  • the hollow particles known ones can be used without any limitation. It is preferable that the hollow particles include an outer shell and a hollow surrounded by the outer shell.
  • the outer shell is usually formed of a resin. Specific examples thereof include vinylidene chloride resin, (meth) acrylic resin, a copolymer of acrylic monomer and vinylidene chloride, and a copolymer of acrylonitrile and vinylidene chloride. Examples thereof include polymers, epoxy resins, phenol resins, melamine resins, and urethane resins.
  • the outer shell of the hollow particles is preferably made of a urethane-based resin, and specifically, a hollow shell composed of an outer shell made of a urethane-based resin and a hollow surrounded by the outer shell. It is preferably a particle.
  • the urethane resin is a resin having a urethane bond and / or a urea bond.
  • the hollow particles may have a hydrophilic group.
  • a cured product made of the curable composition of the present invention for example, a cured product in which the matrix resin is a urethane resin is used as a polishing pad
  • a polishing slurry is used. Compatibility can be improved, and polishing characteristics can be improved.
  • the average particle size of the hollow particles is not particularly limited, but is preferably in the following range. Specifically, the thickness is preferably 1 ⁇ m to 500 ⁇ m, more preferably 5 ⁇ m to 200 ⁇ m.
  • the density of the hollow particles is not particularly limited, but is preferably in the following range. Specifically, it is preferably 0.01 g / cm 3 to 0.5 g / cm 3 , more preferably 0.02 g / cm 3 to 0.3 g / cm 3 .
  • the density is the density of the hollow particles when expanded. If it is an unexpanded type particle, and it is a hollow particle which is mixed with the curable composition and expands by heat at the time of curing, it is preferable that the density when expanded is the above density.
  • the blending amount of the hollow particles may be appropriately determined according to the intended use. That is, since it is not an essential component, it may not be included.
  • the amount of the hollow particles is as follows based on the total amount of each monomer component.
  • the total amount of each monomer component refers to the total amount of the component (A) and the component (B).
  • the compounding amount of the hollow particles is preferably from 0.001 to 20 parts by mass based on 100 parts by mass of the total amount of each monomer component.
  • the following blending amount is particularly preferable. Specifically, the amount is preferably 0.02 parts by mass or more and 20 parts by mass or less, more preferably 0.03 parts by mass or more and 10 parts by mass or less based on 100 parts by mass of the total amount of each monomer component.
  • the cured product of the present invention can have any appropriate hardness. Hardness can be measured according to the Shore method, for example, according to JIS standard (hardness test) K6253.
  • the cured product of the present invention is used for a polishing pad or the like, it preferably has a Shore hardness of 20A to 90D. Further, it is preferably 30A to 70D, more preferably 40A to 50D ("A" indicates the Shore "A” scale, and "D” indicates the hardness on the Shore “D” scale). .
  • the cured product of the present invention when used as a polishing pad, it is preferably 20 or more in Shore A hardness, more preferably 30 or more in Shore A hardness, still more preferably 40 or more in Shore A hardness, and preferably Has a Shore D hardness of 90 or less, more preferably a Shore D hardness of 70 or less, and still more preferably a Shore D hardness of 50 or less.
  • the hardness may have any hardness by changing the blending composition and blending amount as needed.
  • the cured product of the curable composition of the present invention when used for a polishing pad or the like, the cured product preferably has a hysteresis loss of 60% or less, more preferably 50% or less, and more preferably 40% or less. More preferably, The hysteresis loss can be measured, for example, by a method based on JIS K6251. Specifically, the test piece prepared in the form of a dumbbell is stretched by 100% and then returned to its original state, thereby obtaining a hysteresis loss (elongation when stretched and returned to the original state and the area of stress / elongation when stretched. Stress area ⁇ 100) can be measured.
  • a polishing layer formed of a plurality of layers may be provided.
  • the polishing layer includes a first layer having a polishing surface that comes into contact with an object to be polished during polishing, and a surface facing the polishing surface of the first layer.
  • a second layer in contact with the first layer may be used.
  • the physical properties of the first layer can be adjusted by making the second layer have a different hardness and elastic modulus from the first layer. For example, by changing the hardness of the first layer and the hardness of the second layer, it is possible to adjust the polishing property of the object to be polished.
  • the cured product of the present invention may be a so-called fixed abrasive cured product in which abrasive grains are contained as a component.
  • abrasive grains include particles made of a material selected from cerium oxide, silicon oxide, alumina, silicon carbide, zirconia, iron oxide, manganese dioxide, titanium oxide, and diamond, or two or more kinds of particles made of these materials. Is mentioned. Furthermore, these abrasives whose surface is modified can also be used.
  • the cured product of the present invention when used for a polishing pad or the like, by using abrasive particles having a hydrophilic group modified on the surface, the compatibility with slurry or water during polishing is improved, and the polishing characteristics are improved. Becomes possible.
  • the hydrophilic group a hydroxyl group, a thiol group, or an ionic group (at least one ion selected from the group consisting of a carboxyl ion, a sulfonate ion, a phosphate ion, a phosphonate ion, and a quaternary ammonium cation) A group capable of forming).
  • the method of holding these abrasive grains is not particularly limited.
  • the abrasive grains can be held in the urethane resin by being dispersed in the curable composition and then cured.
  • the curable composition used in the present invention is applied to or impregnated into a nonwoven fabric and then cured, whereby the nonwoven fabric polishing pad described above, a cushioning material, a vibration damping material, and a sound absorbing material can be applied. .
  • Production Example 1 ⁇ (A) Method for producing polypseudorotaxane monomer (pRX-1)> (1-1) Preparation of F 108-Dinh 2 terminal amine; As a polymer for forming an axial molecule, a triblock copolymer (Pluronic F108) of linear polyethylene glycol (PEG) -polypropylene glycol (PPG) -polyethylene glycol (PEG) having a weight average molecular weight of 14,600 was prepared.
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PEG polyethylene glycol
  • PEG-PPG-PEG (Pluronic F108) 14g 1.6 g of CDI (1,1′-carbonyldiimidazole) was dissolved in 30 mL of dehydrated dichloromethane, and the mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. Thereafter, 30 mL of water was slowly added dropwise to terminate the reaction. Then, after removing the aqueous layer, the resultant was washed twice with a saturated saline solution, and then water was removed with sodium sulfate. In the obtained dichloromethane solution, 0.6 g of ethylenediamine Was added and stirred at room temperature for 15 hours.
  • the physical properties of the obtained polypseudorotaxane monomer (pRX-1) were as follows from the result of NMR.
  • Axle molecule triblock copolymer of polyethylene glycol (PEG) -polypropylene glycol (PPG) -polyethylene glycol (PEG) having amino groups (polymerizable groups) at both ends.
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PEG polyethylene glycol
  • PEG polyethylene glycol
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PEG polyethylene glycol
  • i 120
  • j 60
  • k 120 on average.
  • Inclusion amount of cyclic molecules 9% (13 ⁇ -cyclodextrins are introduced per one axis molecule).
  • Polymerizable group of the cyclic molecule hydroxyl group.
  • Degree of modification of side chain 0.24 (side chain introduced into 24% of all hydroxyl groups of ⁇ -cyclodextrin).
  • Number average molecular weight of side chain about 59 on average. All the terminals of the modified side chains are hydroxyl groups (polymerizable groups).
  • NBDI (bicyclo [2.2.1] heptane-2,5 (2,6) -diyl) bismethylene diisocyanate.
  • prepolymer (Pre-1) Under a nitrogen atmosphere, a flask equipped with a nitrogen inlet tube, a thermometer, and a stirrer was charged with 500 g of 2,4-tolylene diisocyanate, 900 g of polyoxytetramethylene glycol (number average molecular weight; 1000) and 65 g of diethylene glycol at 80 ° C. for 8 hours. The reaction was carried out to obtain a terminal isocyanate urethane prepolymer having an iso (thio) cyanate equivalent of 540 (Pre-1).
  • TMP trimethylolpropane.
  • DEG diethylene glycol.
  • HP-BCD 2-hydroxypropyl- ⁇ -cyclodextrin (HP- ⁇ CD in which 24% of all hydroxyl groups of ⁇ -cyclodextrin are hydroxypropylated).
  • HP- ⁇ CD 2-hydroxypropyl- ⁇ -cyclodextrin (HP- ⁇ CD in which 19% of all hydroxyl groups of ⁇ -cyclodextrin are hydroxypropylated).
  • PL1 Duranol (registered trademark, polycarbonate diol, number average molecular weight 500) manufactured by Asahi Kasei Chemicals Corporation.
  • Hollow particles Microcapsules 920-40 (manufactured by Nippon Philite). Hollow particles made of a copolymer of an acrylic monomer and vinylidene chloride. Hollow particles 2: hollow urethane ⁇ balloon having a particle size of 30 ⁇ m, the production method is described below.
  • Example 1 Using the polypseudorotaxane monomer (pPX-1) produced in Production Example 1, a curable composition was prepared according to the following formulation. The components were mixed to form a uniform liquid (curable composition). Table 1 shows the compounding amounts.
  • the urethane resin obtained above had an A hardness of 35 and a Young's modulus in a tensile test of 0.5 MPa (elastic modulus) elongation of 740%. Each evaluation method is shown below.
  • Example 1 the cured product produced using the polypseudorotaxane monomer has excellent mechanical properties that are soft and well stretched while having high surface hardness.
  • These physical properties are close to those of the reference example using a polyrotaxane (RX-1) having a bulky group introduced at the terminal, and therefore, in Example 1, as in Reference Example 1, the polypseudorotaxane was used. It can be presumed that the monomer is incorporated into the molecules forming the matrix without leaving the cyclic molecule. However, the elongation rate of Example 1 using the polypseudorotaxane was higher and exhibited an excellent effect. Therefore, the cured product obtained in Example 1 can be suitably used as a polishing pad.
  • Axial molecule triblock copolymer of polyethylene glycol (PEG) -polypropylene glycol (PPG) -polyethylene glycol (PEG) having hydroxyl groups (polymerizable groups) at both ends.
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • PEG polyethylene glycol
  • PEG polypropylene glycol
  • PEG polyethylene glycol
  • Inclusion amount of cyclic molecules 9% (13 ⁇ -cyclodextrins are introduced per one axis molecule).
  • Polymerizable group of the cyclic molecule hydroxyl group.
  • Degree of modification of side chain 0.24 (side chain introduced into 24% of all hydroxyl groups of ⁇ -cyclodextrin). Number average molecular weight of side chain: about 59 on average. All the terminals of the modified side chains are hydroxyl groups (polymerizable groups). Compared with Reference Production Example 1, there is no step of modifying the terminal of the shaft molecule, and the production time can be reduced even in the process in which the cyclic molecule includes the shaft molecule, and the production can be performed at low cost.
  • the physical properties of the obtained polypseudorotaxane monomer (pRX-3) were as follows from the result of NMR.
  • Axial molecule random copolymer of polyoxytetramethylene glycol (PTMG) -polyethylene glycol (PEG) having amino groups (polymerizable groups) at both ends.
  • PTMG polyoxytetramethylene glycol
  • PEG polyethylene glycol
  • R 14 is an ethylene group
  • R 15 is a butylene group
  • R 16 is an ethylene group, and such a structure exists at random.
  • Inclusion amount of cyclic molecules 32% (11 ⁇ -cyclodextrins are introduced into one axis molecule).
  • Polymerizable group of the cyclic molecule hydroxyl group.
  • Degree of modification of side chain 0.19 (side chain introduced into 19% of all hydroxyl groups of ⁇ -cyclodextrin).
  • Number average molecular weight of side chain about 59 on average. All the terminals of the modified side chains are hydroxyl groups (polymerizable groups).
  • polypseudorotaxane monomer (pRX-4).
  • the physical properties of the obtained polypseudorotaxane monomer (pRX-4) were as follows from the result of NMR.
  • Axle molecule triblock copolymer of polyethylene glycol (PEG) -polypropylene glycol (PPG) -polyethylene glycol (PEG) having amino groups (polymerizable groups) at both ends.
  • Examples 2-4, Comparative Examples 2-3, Reference Examples 2-3 A cured product was prepared and evaluated in the same manner as in Example 1 except that a curable composition having the composition shown in Table 2 was used. The results are shown in Table 2.
  • Example 5 The following mass parts of the hollow particles were added to the curable composition of Example 1 to prepare a mixture, and the polishing characteristics were confirmed.
  • the above curable composition was stirred and mixed, defoamed, poured into a mold having a thickness of 10 mm, and heated at 100 ° C. for 15 hours. Cured.
  • Polishing rate The polishing conditions are shown below. Polishing pad: 380 ⁇ . (A spiral groove is formed.) Object to be polished: Three 2-inch sapphire wafers. Slurry: FUJIMI COMPOL 80 stock solution. Pressure: 411 g / cm 2 . Rotation speed: 60 rpm. Time: 1 hour. The polishing rate when polishing was performed under the above conditions was measured.
  • Taber abrasion Measured with a 5130 type device manufactured by Taber. A Taber abrasion test was performed with a load of 1 kg, a rotation speed of 60 rpm, a rotation number of 1000 rotations, and a worn wheel of H-18. Comparative Example 4 A cured product was prepared and evaluated in the same manner as in Example 5, except that a curable composition having the composition shown in Table 3 was used. Table 3 summarizes the mixing ratio of each component and the results.
  • Example 6 Reference Example 4, Comparative Example 4 A cured product was prepared and evaluated in the same manner as in Example 5, except that a curable composition having the composition shown in Table 3 was used. The results are shown in Table 3.
  • Example 7 According to the following formulation, each component was mixed to prepare a uniform liquid (a curable composition containing a photochromic compound).
  • Table 4 shows the compounding amounts.
  • the maximum absorption wavelength is related to the color tone at the time of color development.
  • Color density ⁇ (120) ⁇ (0) ⁇ difference between absorbance at the maximum absorption wavelength after light irradiation for 120 seconds ⁇ (120) ⁇ and light absorbance before light irradiation ⁇ (0) It is. It can be said that the higher this value is, the more excellent the photochromic property is. Further, when the color was developed outdoors, the color tone was evaluated visually.
  • Vickers hardness The Vickers hardness of the obtained photochromic layer was measured using a micro Vickers hardness meter PMT-X7A (manufactured by Matsuzawa Corporation). A quadrangular pyramidal diamond indenter was used as the indenter, and the evaluation was performed under the conditions of a load of 10 gf and an indenter holding time of 30 seconds. The measurement results were shown as an average value of three measurements, excluding the first value having a large measurement error, after performing the measurement four times in total.
  • Example 8 According to the following formulation, each component was mixed to prepare a uniform liquid (a curable composition containing a photochromic compound). Table 5 shows the compounding amounts.
  • the polymerization method is described below. After the uniform liquid of the curable composition has been sufficiently defoamed, it is poured into a mold made of a mold made of a glass mold subjected to a release treatment and a gasket made of an ethylene-vinyl acetate copolymer. did. Next, the mixture was cured for 15 hours while gradually raising the temperature from 30 ° C. to 95 ° C. After the polymerization was completed, the photochromic cured product was removed from the glass mold of the mold. The obtained photochromic cured product had a maximum absorption wavelength of 580 nm, a color density of 0.76, and a fading speed of 61 seconds.
  • the handling properties of the photochromic composition and the moldability of the obtained photochromic cured product were also good.
  • the L-scale Rockwell hardness (HL) of the obtained photochromic cured product was 75.
  • the L scale rock well hardness was measured as follows. ⁇ Evaluation item ⁇ (10) L-scale Rockwell hardness (HL): After keeping the above cured product in a room at 25 ° C. for 1 day, using an Akashi Rockwell hardness tester (model: AR-10), the L-scale of the photochromic cured product was obtained. Lurockwell hardness was measured.
  • Reference Example 6, Comparative Example 6 A cured product was prepared and evaluated in the same manner as in Example 8, except that a curable composition having the composition shown in Table 5 was used. Table 5 shows the results.

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Abstract

La présente invention concerne une composition durcissable comprenant : (A) un monomère de polypseudorotaxane qui présente une structure moléculaire composée d'une molécule annulaire comportant un groupe fonctionnel polymérisable et une molécule axe qui passe à travers l'intérieur annulaire de la molécule annulaire, au moins une extrémité terminale de la molécule axe de comportant pas de groupes volumineux ; et (B) un monomère polymérisable autre que (A) le monomère de polypseudorotaxane. La présente invention peut fournir une composition durcissable qui peut produire un matériau de haute qualité avec une grande productivité, en introduisant une caractéristique possédée par le polyrotaxane dans un article durci (la caractéristique selon laquelle la molécule annulaire se déplace le long de la molécule axe) et en conservant d'excellentes propriétés mécaniques. L'invention peut également fournir un article durci grâce à l'utilisation de la composition durcissable.
PCT/JP2019/030960 2018-08-08 2019-08-06 Composition durcissable contenant un monomère de polypseudorotaxane WO2020032056A1 (fr)

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JP2021105102A (ja) * 2019-12-26 2021-07-26 住友ゴム工業株式会社 ロタキサンポリウレア架橋体、ロタキサンポリウレア・ウレタン架橋体、およびこれらの製造方法
WO2021201089A1 (fr) * 2020-03-31 2021-10-07 株式会社トクヤマ Microballons creux
WO2022163756A1 (fr) * 2021-01-29 2022-08-04 株式会社トクヤマ Microballonnet creux
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KR20220113856A (ko) 2021-02-05 2022-08-17 강원대학교산학협력단 초분자화학 및 공유결합에 기반한 히알루론산 하이드로겔

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JP2021105102A (ja) * 2019-12-26 2021-07-26 住友ゴム工業株式会社 ロタキサンポリウレア架橋体、ロタキサンポリウレア・ウレタン架橋体、およびこれらの製造方法
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WO2022163756A1 (fr) * 2021-01-29 2022-08-04 株式会社トクヤマ Microballonnet creux
WO2022163766A1 (fr) * 2021-01-29 2022-08-04 株式会社トクヤマ Composition durcissable contenant un monomère cyclique multifonctionnel
KR20220113856A (ko) 2021-02-05 2022-08-17 강원대학교산학협력단 초분자화학 및 공유결합에 기반한 히알루론산 하이드로겔

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