JP2023091758A - 有無機ハイブリッド組成物用表面処理剤{surface treatment agent for organic-inorganic hybrid composition} - Google Patents
有無機ハイブリッド組成物用表面処理剤{surface treatment agent for organic-inorganic hybrid composition} Download PDFInfo
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- JP2023091758A JP2023091758A JP2022199392A JP2022199392A JP2023091758A JP 2023091758 A JP2023091758 A JP 2023091758A JP 2022199392 A JP2022199392 A JP 2022199392A JP 2022199392 A JP2022199392 A JP 2022199392A JP 2023091758 A JP2023091758 A JP 2023091758A
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- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 239000012756 surface treatment agent Substances 0.000 title claims abstract description 53
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- 150000001875 compounds Chemical class 0.000 claims description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical group CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical group CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical group CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical group CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- FZXOVEZAKDRQJC-UHFFFAOYSA-N triethoxy(nonyl)silane Chemical group CCCCCCCCC[Si](OCC)(OCC)OCC FZXOVEZAKDRQJC-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical group CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical group CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- BBWMWJONYVGXGQ-UHFFFAOYSA-N triethoxy(undecyl)silane Chemical group CCCCCCCCCCC[Si](OCC)(OCC)OCC BBWMWJONYVGXGQ-UHFFFAOYSA-N 0.000 description 1
- JEPXSTGVAHHRBD-UHFFFAOYSA-N trimethoxy(nonyl)silane Chemical group CCCCCCCCC[Si](OC)(OC)OC JEPXSTGVAHHRBD-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical group CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical group CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- LIJFLHYUSJKHKV-UHFFFAOYSA-N trimethoxy(undecyl)silane Chemical group CCCCCCCCCCC[Si](OC)(OC)OC LIJFLHYUSJKHKV-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
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- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
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- 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
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- 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
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- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
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Abstract
Description
実施例1-1
モノマーとして、3-メタクリロキシプロピルトリメトキシシラン(MPTMS)と2-ヒドロキシエチルメタクリレート(2-HEMA)とを1:1の重量比となるようにメチルエチルケトン(MEK)溶媒下で混合した。重合開始剤として、AIBNを0.01g添加した。このとき、溶媒は、上記モノマーの総重量と同様に混合した。窒素雰囲気下で60℃に3時間成長させた後、常温で12時間混合物を撹拌してモノマーを重合して重合体を得た。
上記実施例1-1において、2-HEMAの代わりに2-ヒドロキシエチルアクリレート(2-HEA)を用いることを除いて、残りは同様に重合体を得た。
上記実施例1-1において、2-HEMAの代わりに2-ヒドロキシブチルアクリレート(2-HBA)を用いることを除いて、残りは同様に重合体を得た。
実施例2-1
平均粒子径が10nmであるジルコニア粉末40g、及び分散溶媒としてメチルエチルケトン(MEK)を60g、及び表面処理剤として実施例1-1による重合体をジルコニア粉末100重量部に対して、20重量部で添加して3時間分散して無機粒子分散液を製造した。
上記実施例2-1において、表面処理剤の添加量をジルコニア粉末100重量部に対して、30重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記実施例2-1において、表面処理剤の添加量をジルコニア粉末100重量部に対して、40重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記実施例2-1において、表面処理剤として、比較例1-1による重合体を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記比較例2-1において、表面処理剤の添加量をジルコニア粉末100重量部に対して、30重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記比較例2-1において、表面処理剤の添加量をジルコニア粉末100重量部に対して、40重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記実施例2-1において、表面処理剤として、比較例1-2による重合体を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記比較例2-4において、表面処理剤の添加量をジルコニア粉末100重量部に対して、30重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記比較例2-4において、表面処理剤の添加量をジルコニア粉末100重量部に対して、40重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
平均粒子径が10nmであるジルコニア粉末40g、及び分散溶媒としてメチルエチルケトン(MEK)を60g、及び表面処理剤としてメタクリロキシプロピルトリメトキシシランをジルコニア粉末100重量部に対して、10重量部で添加して3時間分散して無機粒子分散液を製造した。
上記比較例2-7において、表面処理剤の添加量をジルコニア粉末100重量部に対して、15重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記比較例2-7において、表面処理剤の添加量をジルコニア粉末100重量部に対して、20重量部を添加することを除いて、残りは同様に無機粒子分散液を製造した。
上記実施例2-1~2-3、及び比較例2-1~2-9による無機粒子分散液の光学的特徴を確認するために、総光透過率及びヘイズを測定して下記表1に示した。
実施例3-1
全組成物を基準に分散溶媒としてメチルエチルケトン(MEK)を50重量%、平均粒子径が10nmであるジルコニア粉末を40重量%、表面処理剤として実施例1-1による重合体を10重量%となるように混合した後、30分間撹拌した。その後、ジルコニア粒子がまんべんなく分散できるように、上記混合物100重量部を基準にジルコニアビーズ(平均粒子径:0.05mm)を200重量部仕込んだ後、ペイントシェーカー(paint shaker)で3時間分散して分散液を回収した。製造された分散液50重量部を基準にアクリル系モノマーとしてブチルアクリレート(butylacrylate)を45重量部、分散剤5重量部を添加した後、減圧して分散溶媒を除去して組成物を製造した。
上記実施例3-1において、アクリル系モノマーとして、2-エチルヘキシルアクリレート(2-ethylhexyl acrylate)を添加することを除いて、残りは同様に組成物を製造した。
上記実施例3-1において、アクリル系モノマーとして、イソボルニルアクリレート(isobornyl acrylate)を添加することを除いて、残りは同様に組成物を製造した。
上記実施例3-1において、アクリル系モノマーとして、4-アクリロイルモルホリン(4-acryloyl morpholine)を添加することを除いて、残りは同様に組成物を製造した。
上記実施例3-1において、表面処理剤として、メタクリロキシプロピルトリメトキシシランを添加することを除いて、残りは同様に組成物を製造した。
上記比較例3-1において、アクリル系モノマーとして、2-エチルヘキシルアクリレート(2-ethylhexyl acrylate)を添加することを除いて、残りは同様に組成物を製造した。
上記比較例3-1において、アクリル系モノマーとして、イソボルニルアクリレート(isobornyl acrylate)を添加することを除いて、残りは同様に組成物を製造した。
上記比較例3-1において、アクリル系モノマーとして、4-アクリロイルモルホリン(4-acryloyl morpholine)を添加することを除いて、残りは同様に組成物を製造した。
上記実施例3-1~3-4及び比較例3-1~3-4による組成物の物性を確認するために、屈折率、粘度、及びヘイズを測定して、下記表2に示した。
Claims (8)
- 上記R1~R3は、各々、C2-C12のアルキルトリメトキシシラン基、C2-C12のアルキルトリエトキシシラン基、及びC2-C12のアルキルジメトキシエトキシシラン基からなる群より選ばれる少なくとも1つを含むものである、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
- 上記R4は、H、2-ヒドロキシエチル基、3-ヒドロキシプロピル基、及び2-ヒドロキシブチル基からなる群より選ばれる少なくとも1つを含むものである、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
- 上記mとnは、1:2~2:1の間の整数比を有するものである、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
- BPO、AIBN、及びAIBAからなる群より選ばれる少なくとも1つを含む重合開始剤をさらに含むものである、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
- 上記重合開始剤は、上記表面処理剤中、0.1重量%~1重量%である、請求項5に記載の有無機ハイブリッド組成物用表面処理剤。
- 上記表面処理剤の光透過率は、40%以上である、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
- 上記表面処理剤のヘイズ(haze)は、80%以下である、請求項1に記載の有無機ハイブリッド組成物用表面処理剤。
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KR100214288B1 (ko) * | 1993-04-16 | 1999-08-02 | 성재갑 | 안개서림 방지용 내마모성 피복조성물 및 이를 도포한 합성수지 성형품 |
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EP1841803B1 (en) * | 2005-01-25 | 2009-07-22 | LG Chem, Ltd. | Thermally curable resin composition with extended storage stability and good adhesive property |
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WO2019151265A1 (ja) * | 2018-02-01 | 2019-08-08 | Agc株式会社 | 基材および共重合体 |
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US20230193071A1 (en) | 2023-06-22 |
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