[go: up one dir, main page]

WO2020116161A1 - Copolymère séquencé - Google Patents

Copolymère séquencé Download PDF

Info

Publication number
WO2020116161A1
WO2020116161A1 PCT/JP2019/045411 JP2019045411W WO2020116161A1 WO 2020116161 A1 WO2020116161 A1 WO 2020116161A1 JP 2019045411 W JP2019045411 W JP 2019045411W WO 2020116161 A1 WO2020116161 A1 WO 2020116161A1
Authority
WO
WIPO (PCT)
Prior art keywords
repeating unit
polymer block
mol
polymer
present
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.)
Ceased
Application number
PCT/JP2019/045411
Other languages
English (en)
Japanese (ja)
Inventor
雄 新家
依慶 米山
和也 上西
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.)
Yokohama Rubber Co Ltd
Original Assignee
Yokohama Rubber Co Ltd
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 Yokohama Rubber Co Ltd filed Critical Yokohama Rubber Co Ltd
Publication of WO2020116161A1 publication Critical patent/WO2020116161A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule

Definitions

  • the present invention relates to a block copolymer.
  • Patent Document 1 discloses that a hydrophilic polymer portion obtained by polymerizing a monomer mixture containing N,N-dimethylacrylamide and N-methylolacrylamide and methylmethacrylate (methacrylic acid). Block copolymers comprising a hydrophobic polymer portion obtained by polymerizing a monomer mixture containing (methyl acid)) (Examples, etc.). Patent Document 1 describes that the N-methylolacrylamide is dehydrated and condensed by heating to form a crosslinked structure.
  • an object of the present invention is to provide a block copolymer having excellent fast curability.
  • the present inventors have found that the above problems can be solved by introducing a repeating unit having an alkoxysilyl group, and have reached the present invention. That is, the present inventors have found that the above problems can be solved by the following configurations.
  • the numerical range represented by “to” means a range including the numerical values before and after “to” as the lower limit value and the upper limit value.
  • each component may be used alone or in combination of two or more.
  • the content of the component means the total content unless otherwise specified.
  • the block copolymer of the present invention is A polymer block A having a repeating unit A1 represented by the following formula (A1) or a repeating unit A2 represented by the following formula (A2), A polymer block B having a repeating unit represented by the following formula (B1), At least one of the polymer block A and the polymer block B is a block copolymer (hereinafter, also referred to as “polymer of the present invention”) having a repeating unit C1 represented by the following formula (C1). is there.
  • R represents a hydrogen atom or a methyl group.
  • R A1 represents a hydrogen atom or a hydrocarbon group. The two R A1 may be the same or different.
  • R A2 represents a hydrogen atom or a hydrocarbon group.
  • p represents an integer of 1 or more.
  • R B1 represents a hydrocarbon group.
  • L represents a single bond or a divalent linking group.
  • R C11 and R C12 each independently represent a hydrocarbon group.
  • m represents an integer of 1 to 3.
  • n is an integer of 2 or more, a plurality of R C11 existing may be the same or different.
  • n is 2, the two R C12 may be the same or different.
  • the polymer of the present invention has such a constitution, it can be considered that the above-mentioned effects can be obtained. Although the reason is not clear, it is presumed that the alkoxysilyl group contained in the repeating unit C1 has high reactivity.
  • the polymer of the present invention may be a diblock copolymer of one polymer block A and one polymer block B, or a multiblock copolymer in which at least one of each polymer block is present in plural. Good. Further, the polymer of the present invention may have a polymer block that does not correspond to either the polymer block A or the polymer block B.
  • the polymer of the present invention is excellent in quick-curing property, and when formed into a cured film, it is excellent in antifogging property, adhesion property, durability, water resistance, warm water resistance and appearance. It is preferably a diblock copolymer of A and one polymer block B.
  • the polymer of the present invention "excellent in quick-curing property, and when formed into a cured film, it is excellent in antifogging property, adhesiveness, durability, water resistance, warm water resistance and appearance” Is more effective.”
  • the shape of the polymer of the present invention include a linear shape, a graft shape, and a star shape. Among them, the linear shape is preferable because the effects of the present invention are more excellent.
  • the polymer block A is generally more hydrophilic than the polymer block B, and the polymer block B is relatively more hydrophobic than the polymer block A.
  • the polymer block A has the repeating unit A1 represented by the above formula (A1) or the repeating unit A2 represented by the above formula (A2).
  • the polymer block A may have a repeating unit other than the repeating unit A1 and the repeating unit A2.
  • the repeating unit is not particularly limited.
  • at least one of the polymer block A and the polymer block B has the repeating unit C1 represented by the above formula (C1).
  • the polymer block A has a repeating unit A1 represented by the following formula (A1) or a repeating unit A2 represented by the following formula (A2).
  • R represents a hydrogen atom or a methyl group.
  • R A1 represents a hydrogen atom or a hydrocarbon group. The two R A1 may be the same or different.
  • R A1 represents a hydrogen atom or a hydrocarbon group.
  • the above-mentioned hydrocarbon group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic.
  • Specific examples of the aliphatic hydrocarbon group include a linear or branched alkyl group (especially 1 to 30 carbon atoms), a linear or branched alkenyl group (especially 2 to 30 carbon atoms), Examples thereof include a linear or branched alkynyl group (in particular, having 2 to 30 carbon atoms).
  • aromatic hydrocarbon group examples include an aromatic hydrocarbon group having 6 to 18 carbon atoms such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
  • R A1 is preferably a hydrocarbon group, more preferably an aliphatic hydrocarbon group, and further preferably a linear alkyl group, for the reason that the effects of the present invention are more excellent.
  • a linear alkyl group having 1 to 5 carbon atoms is particularly preferable.
  • R represents a hydrogen atom or a methyl group.
  • R A2 represents a hydrogen atom or a hydrocarbon group.
  • p represents an integer of 1 or more.
  • R A2 represents a hydrogen atom or a hydrocarbon group. Specific examples and preferred embodiments of the R A2 is the same as R A1 in the formula (A1).
  • p represents an integer of 1 or more.
  • the upper limit of p is not particularly limited, but is preferably 10 or less because the effects of the present invention are more excellent.
  • the total content of the repeating unit A1 and the repeating unit A2 in the polymer block A is preferably 50 mol% or more, and more preferably 70 mol% or more from the reason that the effects of the present invention are more excellent. It is preferably 90 mol% or more, and more preferably 90 mol% or more.
  • the upper limit of the total content of the repeating unit A1 and the repeating unit A2 in the polymer block A is not particularly limited and is 100 mol%.
  • the “total content of the repeating unit A1 and the repeating unit A2 in the polymer block A” (mol %) means the repeating unit A1 and the repeating unit A2 with respect to all the repeating units (the number of moles) of the polymer block A. It means the ratio (mol %) of the total (number of moles).
  • the content of the polymer block A is preferably 20 to 95 mol %, more preferably 30 to 90 mol %, for the reason that the effects of the present invention are more excellent. It is more preferably 40 to 80 mol %.
  • the “content of the polymer block A” means the ratio (mol %) of all the repeating units (mol number) of the polymer block A to all the repeating units (mol number) of the block copolymer. means.
  • the content of the polymer block A is preferably 20 to 95% by mass, more preferably 30 to 90% by mass, for the reason that the effects of the present invention are more excellent. It is more preferably 40 to 80% by mass.
  • the polymer block B has the repeating unit B1 represented by the above formula (B1).
  • the polymer block B may have a repeating unit other than the repeating unit B1.
  • the repeating unit is not particularly limited.
  • at least one of the polymer block A and the polymer block B has the repeating unit C1 represented by the above formula (C1).
  • the polymer block B has a repeating unit B1 represented by the following formula (B1).
  • R represents a hydrogen atom or a methyl group.
  • R B1 represents a hydrocarbon group.
  • R B1 represents a hydrocarbon group. Specific examples and preferred embodiments of the above hydrocarbon group are the same as R A1 in formula (A1).
  • the content of the repeating unit B1 in the polymer block B is preferably 50 mol% or more, more preferably 70 mol% or more, and 90 mol% or more for the reason that the effects of the present invention are more excellent. Is more preferable.
  • the upper limit of the content of the repeating unit B1 in the polymer block B is not particularly limited and is 100 mol%.
  • the “content of the repeating unit B1 in the polymer block B” (mol %) means the ratio (mol%) of the repeating unit B1 (mol number) to all the repeating units (mol number) of the polymer block B. means.
  • the content of the polymer block B is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, for the reason that the effects of the present invention are more excellent. It is more preferably 20 to 60 mol %.
  • the “content of the polymer block B” (mol %) means the ratio (mol %) of all the repeating units (mol number) of the polymer block B to all the repeating units (mol number) of the block copolymer. means.
  • the content of the polymer block B is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, for the reason that the effects of the present invention are more excellent. It is more preferably 20 to 60% by mass.
  • the ratio of the content of the polymer block A to the content of the polymer block B is a molar ratio because the effects of the present invention are more excellent. And is preferably 0.25 to 19, more preferably 0.42 to 9.0, and further preferably 0.67 to 4.0.
  • the total content of the polymer block A and the polymer block B is preferably 50 mol% or more, and 70 mol% or more for the reason that the effects of the present invention are more excellent. More preferably, it is more preferably 90 mol% or more.
  • the upper limit of the total content of the polymer block A and the polymer block B is not particularly limited and is 100 mol%.
  • the “total content of the polymer block A and the polymer block B” (mol %) means all the repeating units of the polymer block A and the polymer blocks with respect to all the repeating units (the number of moles) of the block copolymer. It means the ratio (mol %) of the total (mol number) of all repeating units of B.
  • the total content of the polymer block A and the polymer block B is preferably 50% by mass or more, and 70% by mass or more, for the reason that the effects of the present invention are more excellent. Is more preferable, and 90% by mass or more is further preferable.
  • the upper limit of the total content of the polymer block A and the polymer block B is not particularly limited and is 100% by mass.
  • At least one of the polymer block A and the polymer block B has the repeating unit C1 represented by the following formula (C1). From the reason that the effects of the present invention are more excellent, it is preferable that at least the polymer block B has the repeating unit C1, and it is more preferable that both the polymer block A and the polymer block B have the repeating unit C1.
  • L represents a single bond or a divalent linking group.
  • R C11 and R C12 each independently represent a hydrocarbon group.
  • m represents an integer of 1 to 3.
  • m is an integer of 2 or more, a plurality of R C11 existing may be the same or different.
  • n is 2, the two R C12 may be the same or different.
  • L represents a single bond or a divalent linking group.
  • the divalent linking group include linear, branched or cyclic divalent aliphatic hydrocarbon groups (eg, alkylene groups such as methylene group, ethylene group, propylene group) and divalent aromatic groups.
  • Hydrocarbon group (eg phenylene group), —O—, —S—, —SO 2 —, —NR L —, —CO—, —NH—, —COO—, —CONR L —, —O—CO— O—, —SO 3 —, —NHCOO—, —SO 2 NR L —, —NH—CO—NH— or a group combining two or more thereof (eg, alkyleneoxy group, alkyleneoxycarbonyl group, alkylenecarbonyloxy) Group) and the like.
  • R L represents a hydrogen atom or an alkyl group (preferably having 1 to 10 carbon atoms).
  • the above L is preferably an alkyleneoxycarbonyl group for the reason that the effects of the present invention are more excellent.
  • R C11 and R C12 each independently represent a hydrocarbon group.
  • Specific examples and preferred embodiments of the above hydrocarbon group are the same as R A1 in formula (A1).
  • n represents an integer of 0 to 2.
  • the content of the repeating unit C1 in the polymer block A is preferably 0.1 to 20 mol% and more preferably 0.2 to 10 mol% for the reason that the effects of the present invention are more excellent. It is preferably 0.5 to 5 mol% and more preferably 0.5 to 5 mol %.
  • the content of the repeating unit C1 in the polymer block B is preferably 0.1 to 20 mol% and more preferably 0.2 to 10 mol% for the reason that the effects of the present invention are more excellent. It is preferably 0.5 to 5 mol% and more preferably 0.5 to 5 mol %.
  • the “content of the repeating unit C1 in the polymer block A” (mol %) means the ratio (mol%) of the repeating unit C1 (mol number) to all the repeating units (mol number) of the polymer block A.
  • the “content of the repeating unit C1 in the polymer block B” means the ratio (mol%) of the repeating unit C1 (the number of moles) to all the repeating units (the number of moles) of the polymer block B.
  • the content of the repeating unit C1 is preferably 0.1 to 20 mol% with respect to all the repeating units of the block copolymer for the reason that the effects of the present invention are more excellent. , 0.2 to 10 mol% is more preferable, and 0.3 to 5 mol% is further preferable.
  • At least one of the polymer block A and the polymer block B preferably has a repeating unit C2 represented by the following formula (C2) for the reason that the effects of the present invention are more excellent. .. From the reason that the effects of the present invention are more excellent, it is preferable that at least the polymer block B has the repeating unit C2, and it is more preferable that both the polymer block A and the polymer block B have the repeating unit C2.
  • R represents a hydrogen atom or a methyl group.
  • R C2 represents a hydrogen atom or a hydrocarbon group having a hydroxy group.
  • R C2 represents a hydrogen atom or a hydrocarbon group having a hydroxy group.
  • Specific examples and preferred embodiments of the hydrocarbon group in the hydrocarbon group having a hydroxy group are the same as R A1 in formula (A1).
  • Examples of the hydrocarbon group having a hydroxy group include a 2-hydroxyethyl group.
  • the content of the repeating unit C2 in the polymer block A is preferably 0.1 to 20 mol% and more preferably 0.2 to 10 mol% for the reason that the effects of the present invention are more excellent. It is preferably 0.5 to 5 mol% and more preferably 0.5 to 5 mol %.
  • the content of the repeating unit C2 in the polymer block B is preferably 0.1 to 20 mol% and more preferably 0.2 to 10 mol% for the reason that the effects of the present invention are more excellent. It is preferably 0.5 to 5 mol% and more preferably 0.5 to 5 mol %.
  • the “content of the repeating unit C2 in the polymer block A” (mol %) means the ratio (mol %) of the repeating unit C2 (mol number) to all the repeating units (mol number) of the polymer block A.
  • the “content of the repeating unit C2 in the polymer block B” means the ratio (mol%) of the repeating unit C2 (the number of moles) to all the repeating units (the number of moles) of the polymer block B.
  • the content of the repeating unit C2 is preferably 0.1 to 20 mol% based on all the repeating units of the block copolymer, for the reason that the effects of the present invention are more excellent. , 0.2 to 10 mol% is more preferable, and 0.3 to 5 mol% is further preferable.
  • the total content of the repeating unit C1 and the repeating unit C2 is 0.1 to 20 mols based on the total repeating units of the block copolymer for the reason that the effects of the present invention are more excellent. %, preferably 0.2 to 10 mol %, more preferably 0.3 to 5 mol %.
  • the ratio of the content of the repeating unit C1 to the content of the repeating unit C2 is a molar ratio of 0. It is preferably 1 to 10, more preferably 0.2 to 5, and further preferably 0.3 to 3.
  • the number average molecular weight (Mn) of the polymer of the present invention is not particularly limited, but is preferably 1,000 to 1,000,000, and preferably 10,000 to 100, for the reason that the effects of the present invention are more excellent. It is more preferably 000, and even more preferably 20,000 to 80,000.
  • the weight average molecular weight (Mw) of the polymer of the present invention is not particularly limited, but is preferably 1,000 to 1,000,000, and preferably 10,000 to 100, for the reason that the effects of the present invention are more excellent. It is more preferably 000, and even more preferably 20,000 to 80,000.
  • the molecular weight distribution (Mw/Mn) of the polymer of the present invention is not particularly limited, but is preferably 10 or less, more preferably 5 or less for the reason that the effect of the present invention is more excellent.
  • the lower limit of the molecular weight distribution is not particularly limited, but is usually 1.0 or more.
  • Mn and Mw are standard polystyrene conversion values obtained by gel permeation chromatography (GPC) measurement under the following conditions.
  • GPC gel permeation chromatography
  • the method for producing the polymer of the present invention is not particularly limited, and a conventionally known method can be used. Among them, the method using the living radical polymerization method is preferable, and the method using the RAFT method (reversible addition fragmentation chain transfer polymerization method) (particularly the method using a trithiocarbonate compound as a chain transfer agent) is more preferable. ..
  • a monomer that becomes the repeating unit B1 for example, methyl methacrylate
  • a monomer that becomes the repeating unit C1 for example, 3-methacryloxypropyltrimethoxysilane
  • a monomer eg, 2-hydroxyethyl methacrylate
  • a monomer eg, N,N-dimethylacrylamide
  • a monomer for example, 3-methacryloxypropyltrimethoxysilane
  • a monomer for example, 2-hydroxyethyl methacrylate
  • the polymer block A and A method for producing a block copolymer containing the united block B in this case, both the polymer block A and the polymer block B have the repeating unit C1 and the like can be mentioned.
  • composition of the present invention is a composition containing the above-mentioned polymer of the present invention.
  • the composition may contain components other than the polymer of the present invention. Examples of the components include a leveling agent, a phosphate ester monomer, a solvent (for example, alcohol), and the like.
  • the composition of the present invention is useful, for example, as an anti-fog coating agent (coating agent for preventing fogging).
  • the cured film of the present invention is not particularly limited as long as it is formed from the composition of the present invention described above.
  • the method for producing the cured film of the present invention is not particularly limited, but for example, the composition of the present invention described above is applied onto a substrate (preferably a (meth)acrylate resin substrate) and heated (preferably 50 to 200). °C) and the like. By heating, the alkoxysilyl groups in the repeating unit C1 react (crosslink) with each other to form a cured film.
  • the polymer of the present invention has the repeating unit C2
  • the alkoxysilyl group in the repeating unit C1 and the —OH group in the repeating unit C2 are combined.
  • crosslinking Upon reaction (crosslinking), a cured film is formed.
  • the cured film of the present invention is useful, for example, as an anti-fog film (a film for preventing fogging).
  • Example 4 Methyl methacrylate (Tokyo Kasei: 16 mL), 2-hydroxyethyl methacrylate (Tokyo Kasei: 0.4 mL), 3-methacryloxypropyltrimethoxysilane (Shin-Etsu Silicone: 0.4 mL), azobisiso Butyronitrile (manufactured by Tokyo Chemical Industry: 10 mg), 4-cyano-4-(((dodecylthio)carbothioyl)thio)pentanoic acid (manufactured by Boron Molecular: 0.12 g) and N,N-dimethylformamide (manufactured by Kanto Kagaku: 50 mL) were mixed, heated to 70° C., and stirred.
  • the resulting block copolymer had a repeating unit derived from N,N-dimethylacrylamide (corresponding to the repeating unit A1 described above) (97 mol %) and a repeating unit derived from 3-methacryloxypropyltrimethoxysilane (described above.
  • Polymer block A (corresponding to polymer block A described above) consisting of (1 mol%) and 2-hydroxyethyl methacrylate (corresponding to repeating unit C2 described above) (2 mol%) And methyl methacrylate (corresponding to the repeating unit B1 described above) (97 mol %), a repeating unit derived from 3-methacryloxypropyltrimethoxysilane (corresponding to the repeating unit C1 described above) (1 mol %), and methacrylic acid A block copolymer (straight chain) containing a polymer block B (corresponding to the polymer block B described above) consisting of 2-hydroxyethyl (corresponding to the repeating unit C2 described above) (2 mol %).
  • the content of the polymer block A in the block copolymer is 50 mol%
  • the content of the polymer block B in the block copolymer is 50 mol%.
  • ⁇ Fast curability> Each of the obtained block copolymers is dissolved in a solvent, and this is coated on a methyl methacrylate resin substrate by a spray coating method so that the thickness of the coating film (cured film) after curing becomes 3 to 5 ⁇ m. After drying at 30° C. for 1 minute, heat curing was performed at 100° C. Then, the rapid curing property was evaluated according to the following 5 grades. In addition, if the evaluation is ⁇ or more, there is no practical problem, and ⁇ is more preferable, and ⁇ + is more preferable. ⁇ + : Cured within 4 minutes. ⁇ : Hardens within more than 4 minutes and within 5 minutes. ⁇ : Cured in more than 5 minutes and less than 10 minutes. (Triangle
  • ⁇ Warm water resistance> Each of the obtained block copolymers is dissolved in a solvent, and this is coated on a methyl methacrylate resin substrate by a spray coating method so that the thickness of the coating film (cured film) after curing becomes 3 to 5 ⁇ m. After drying at 30° C. for 1 minute, heat curing was performed at 100° C. until it was sufficiently cured. The obtained cured film was immersed in warm water of 40° C. for 240 hours, the water was removed by a blower, and the appearance of the cured film after drying at room temperature for 1 hour was visually evaluated. In addition, when the evaluation is ⁇ or more, there is no practical problem, and when ⁇ , it is more preferable. A: No whitening is observed. ⁇ : A slight whitening is observed. ⁇ : Remarkable whitening is observed. X: Elution of the cured film is observed.
  • Examples 1 to 5 in which at least one of the united block A and the polymer block B had the repeating unit C1 showed excellent fast curability and hot water resistance showed excellent fast curability and hot water resistance. From the comparison of Examples 1 to 5, Examples 1 and 3 to 5 in which the polymer block A has the repeating unit C1 showed more excellent fast curability. Further, from the comparison of Examples 1 to 5, Examples 2 to 5 in which the polymer block B has the repeating unit C1 showed more excellent hot water resistance. Further, from the comparison of Examples 1 to 5, Examples 4 to 5 in which at least one of the polymer block A and the polymer block B has the repeating unit C2 showed more excellent fast curability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

L'objet de la présente invention est de fournir un copolymère séquencé présentant une excellente aptitude au durcissement rapide. Ce copolymère séquencé comprend une séquence polymère A comportant un motif répété à base de (méth)acrylamide et similaire, et une séquence polymère B comportant un motif répété à base de (méth)acrylate, la séquence polymère A et/ou la séquence polymère B comportant un motif répété C1 possédant un groupe alcoxysilyle.
PCT/JP2019/045411 2018-12-04 2019-11-20 Copolymère séquencé Ceased WO2020116161A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-227202 2018-12-04
JP2018227202A JP6729667B2 (ja) 2018-12-04 2018-12-04 ブロック共重合体

Publications (1)

Publication Number Publication Date
WO2020116161A1 true WO2020116161A1 (fr) 2020-06-11

Family

ID=70973613

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/045411 Ceased WO2020116161A1 (fr) 2018-12-04 2019-11-20 Copolymère séquencé

Country Status (2)

Country Link
JP (1) JP6729667B2 (fr)
WO (1) WO2020116161A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022129140A (ja) * 2021-02-24 2022-09-05 株式会社カネカ 硬化性組成物および硬化物

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002060449A (ja) * 2000-08-11 2002-02-26 Kanegafuchi Chem Ind Co Ltd ブロック共重合体を含有する硬化性組成物
JP2002338625A (ja) * 2001-05-14 2002-11-27 Kanegafuchi Chem Ind Co Ltd ブロック共重合体
JP2017008217A (ja) * 2015-06-23 2017-01-12 日油株式会社 防曇剤組成物
JP2017179174A (ja) * 2016-03-31 2017-10-05 日油株式会社 防曇剤組成物用の触媒
JP2017179112A (ja) * 2016-03-30 2017-10-05 Dic株式会社 ブロックポリマー、並びにこれを含むコーティング剤および塗膜
WO2018067284A1 (fr) * 2016-10-06 2018-04-12 Johnson & Johnson Vision Care, Inc. Prépolymères triblocs et leur utilisation dans des hydrogels de silicone
WO2018181251A1 (fr) * 2017-03-31 2018-10-04 東亞合成株式会社 Composition de résine durcissable et son procédé de production
JP2018188627A (ja) * 2017-05-05 2018-11-29 ザ・スウォッチ・グループ・リサーチ・アンド・ディベロップメント・リミテッド エピラム処理剤およびそのようなエピラム処理剤を用いたエピラム処理方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002060449A (ja) * 2000-08-11 2002-02-26 Kanegafuchi Chem Ind Co Ltd ブロック共重合体を含有する硬化性組成物
JP2002338625A (ja) * 2001-05-14 2002-11-27 Kanegafuchi Chem Ind Co Ltd ブロック共重合体
JP2017008217A (ja) * 2015-06-23 2017-01-12 日油株式会社 防曇剤組成物
JP2017179112A (ja) * 2016-03-30 2017-10-05 Dic株式会社 ブロックポリマー、並びにこれを含むコーティング剤および塗膜
JP2017179174A (ja) * 2016-03-31 2017-10-05 日油株式会社 防曇剤組成物用の触媒
WO2018067284A1 (fr) * 2016-10-06 2018-04-12 Johnson & Johnson Vision Care, Inc. Prépolymères triblocs et leur utilisation dans des hydrogels de silicone
WO2018181251A1 (fr) * 2017-03-31 2018-10-04 東亞合成株式会社 Composition de résine durcissable et son procédé de production
JP2018188627A (ja) * 2017-05-05 2018-11-29 ザ・スウォッチ・グループ・リサーチ・アンド・ディベロップメント・リミテッド エピラム処理剤およびそのようなエピラム処理剤を用いたエピラム処理方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022129140A (ja) * 2021-02-24 2022-09-05 株式会社カネカ 硬化性組成物および硬化物
JP7674852B2 (ja) 2021-02-24 2025-05-12 株式会社カネカ 硬化性組成物および硬化物

Also Published As

Publication number Publication date
JP6729667B2 (ja) 2020-07-22
JP2020090577A (ja) 2020-06-11

Similar Documents

Publication Publication Date Title
US5401528A (en) Use of compositions based on organically modified silicic acid polycondensates for coating teeth and dental prostheses
JP6556128B2 (ja) 少なくとも２つの環式カルボナート基と１つのシロキサン基とを有する化合物を含む被覆材料
JP7202253B2 (ja) 放射線硬化性オルガノポリシロキサン組成物並びに剥離シート
JP4409397B2 (ja) シリコーン樹脂組成物及び成形体
JP2013525512A (ja) シリコーン（メタ）アクリルアミドモノマー、ポリマー、眼用レンズおよびコンタクトレンズ
JP5647176B2 (ja) 低い重合応力を有するラジカル重合性マクロ環状樹脂組成物
JP2013543038A (ja) 制御可能な架橋度を有する材料
TW201716236A (zh) 剝離紙或剝離薄膜用矽酮組成物、剝離紙及剝離薄膜
JP2021502445A (ja) 光硬化性組成物およびその硬化物を含むコーティング層
JP2001151831A5 (fr)
JP6729667B2 (ja) ブロック共重合体
JP2019167431A (ja) 高誘電率を有する官能基を有する酸性基含有重合性単量体
JPWO2020059726A1 (ja) ハードコート組成物、ハードコートフィルム、ハードコートフィルムを有する物品、画像表示装置、及びハードコートフィルムの製造方法
JP2535986B2 (ja) 塗料用組成物
US20210340415A1 (en) Admixed modifiers for adhesives
JP4215119B2 (ja) アクリル系のホットメルト型粘着剤樹脂組成物及びそれを用いる粘着シート
JPS62260868A (ja) 被覆組成物
CN105377911B (zh) 组合物、固化性组合物、其制造方法及固化物
JP2023155867A (ja) 装飾品の製造方法及びそれに用いる紫外線硬化樹脂組成物
JP2020172560A (ja) 組成物、硬化皮膜、及び、積層体
JPH07126332A (ja) ビニル系共重合体、その製造方法、及び常温硬化性樹脂組成物
JP2020172561A (ja) 組成物、硬化皮膜、及び、積層体
JP2019182747A (ja) 高誘電率を有する官能基を有する酸性基含有重合性単量体
US20040010110A1 (en) Adhesion promoters for silicone materials
JP5125100B2 (ja) 重合性不飽和結合を有するアクリル系重合体の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19894324

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19894324

Country of ref document: EP

Kind code of ref document: A1