WO2022220023A1 - 金属含有シリルオキシ化合物、金属含有シリルオキシ基被覆粒子、その製造方法、及び分散組成物 - Google Patents
金属含有シリルオキシ化合物、金属含有シリルオキシ基被覆粒子、その製造方法、及び分散組成物 Download PDFInfo
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- WO2022220023A1 WO2022220023A1 PCT/JP2022/013105 JP2022013105W WO2022220023A1 WO 2022220023 A1 WO2022220023 A1 WO 2022220023A1 JP 2022013105 W JP2022013105 W JP 2022013105W WO 2022220023 A1 WO2022220023 A1 WO 2022220023A1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229940075419 choline hydroxide Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- XTXCFTMJPRXBBC-UHFFFAOYSA-N methyl 4,4-dimethyl-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(C)(C)C XTXCFTMJPRXBBC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-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
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000011856 silicon-based particle Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G23/00—Compounds of titanium
- C01G23/04—Oxides; Hydroxides
- C01G23/047—Titanium dioxide
- C01G23/053—Producing by wet processes, e.g. hydrolysing titanium salts
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G23/00—Compounds of titanium
- C01G23/04—Oxides; Hydroxides
- C01G23/047—Titanium dioxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
Definitions
- the present invention relates to a metal-containing silyloxy compound, metal-containing silyloxy group-coated particles, a method for producing the same, and a dispersion composition.
- a high refractive index material is used to form the optical members.
- a high refractive index material for example, a composition in which metal oxide particles such as zirconium oxide are dispersed in an organic component is used.
- a method for improving the dispersibility of metal oxide particles a method of capping the surface of metal oxide particles with a capping agent is known.
- Organosilanes such as n-propyltrimethoxysilane are known as capping agents (see Patent Document 1).
- the present invention has been made in view of such conventional circumstances, a compound used as a capping agent to give particles excellent in dispersibility and refractive index, particles coated with the compound, a method for producing the same, and to provide a dispersion composition containing the particles.
- the present inventors have conducted extensive research to solve the above problems. As a result, the present inventors have found that the above-mentioned problems can be solved by a given metal-containing silyloxy compound, and have completed the present invention. Specifically, the present invention provides the following.
- a first aspect of the present invention is a compound having a structure represented by the following formula (1).
- R 1 represents an organic group having 1 to 30 carbon atoms
- R 2 represents a group represented by OR 3 or a group represented by the following formula (2)
- R 3 represents an organic group having 1 to 30 carbon atoms
- n1 and n2 each independently represent an integer of 0 or more, provided that n1+2 ⁇ n2 is a valence determined by the type of L
- L represents aluminium, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium or tantalum
- * represents a bond.
- R 4 and R 5 represent an organic group having 1 to 30 carbon atoms which may have an oxygen atom.
- a second aspect of the present invention is a particle having a structure represented by the above formula (1) on its surface.
- a third aspect of the present invention is a dispersion composition containing the above particles.
- a fourth aspect of the present invention is a method for producing particles having a surface structure represented by the above formula (1)
- the manufacturing method is a particle coating step of reacting particles having hydroxyl groups on their surface with a compound represented by the following formula (30) to obtain particles having a structure represented by the above formula (1) on the surface, or
- the manufacturing method is a first reaction step of reacting particles having hydroxyl groups on the surface with a compound represented by the following formula (4) to obtain particles having a structure represented by the following formula (5) on the surface; a second reaction step of reacting the particles obtained in the first reaction step with a compound represented by the following formula (6) to obtain particles having a surface structure represented by the above formula (1);
- R 1 , R 2 , n1, n2, and L are as defined above, and R 60 and R 70 each represent an organic group having 1 to 30 carbon atoms.
- R 1 , R 60 and R 70 are as defined above, and R 8 represents an organic group having 1 to 30 carbon atoms.
- R 9 OL(R 2 ) n1 (O) n2 (6) (In the formula, R 2 , n1, n2, and L are as defined above, and R 9 represents an organic group having 1 to 30 carbon atoms.)
- a compound according to the present invention has a structure represented by the above formula (1).
- the above compound can be used as a capping agent that provides particles with excellent dispersibility and refractive index.
- the organic group having 1 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include an alkyl group having 1 to 30 carbon atoms and a cycloalkyl group having 3 to 30 carbon atoms. , an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkoxyalkyl group having 2 to 30 carbon atoms. An alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms is preferred.
- the alkyl group having 1 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, n-pentyl group and isopentyl group.
- alkyl groups having 6 to 24 carbon atoms are preferable, and alkyl groups having 8 to 20 carbon atoms are preferred. Alkyl groups are more preferred.
- the cycloalkyl group having 3 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl and cyclododecyl cyclooctadecyl group, cycloicosyl group, etc., and from the viewpoint of ease of synthesis of the above compounds and dispersibility of the obtained particles, cycloalkyl groups having 6 to 24 carbon atoms are preferred, and cycloalkyl groups having 8 to 20 carbon atoms are preferred. is more preferred.
- the alkenyl group having 2 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include a vinyl group, an allyl group, and the like. , is preferably an alkenyl group having 6 to 24 carbon atoms, more preferably an alkenyl group having 8 to 20 carbon atoms.
- the aryl group having 6 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, and the like. , preferably an aryl group having 8 to 24 carbon atoms, more preferably an aryl group having 10 to 20 carbon atoms.
- the alkoxyalkyl group having 2 to 30 carbon atoms represented by R 1 is not particularly limited, and examples thereof include a methoxymethyl group, a methoxyethyl group, an ethoxymethyl group, an ethoxyethyl group and the like.
- an alkoxyalkyl group having 6 to 24 carbon atoms is preferable, and an alkoxyalkyl group having 8 to 20 carbon atoms is more preferable.
- n1 represents an integer of 2 or more
- a plurality of R 2 may be the same or different.
- R 2 is represented, for example, by OR 3 , where R 3 is the alkyl group having 1 to 30 carbon atoms, the cycloalkyl group having 3 to 30 carbon atoms, or the cycloalkyl group having 3 to 30 carbon atoms.
- a 2,4-pentanedionato group ie, an acetylacetonato group
- a 2,2,6,6-tetramethyl-3,5-heptanedionato group are also included.
- the alkylacetoacetate group having 5 to 30 carbon atoms represented by R 2 is not particularly limited, and examples thereof include a methylacetoacetate group, an ethylacetoacetate group and the like. , ethyl acetoacetate groups are preferred.
- R 2 is preferably a group represented by the above formula (2) from the viewpoint of the dispersibility of the resulting particles.
- L is preferably yttrium, titanium, zirconium, or hafnium, more preferably titanium or zirconium, from the viewpoint of the refractive index of the resulting particles.
- the organic group having 1 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include alkyl groups having 1 to 30 carbon atoms, cycloalkyl groups, alkenyl groups having 2 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, and alkoxyalkyl groups having 2 to 30 carbon atoms.
- An alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms is preferred.
- R 4 or R 5 has an oxygen atom
- an organic group having 1 to 30 is bonded to the P, and the organic group is preferably an alkyl group having 1 to 30 carbon atoms or an alkoxyalkyl group having 2 to 30 carbon atoms.
- the alkyl group having 1 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 . From the standpoint of dispersibility, etc., an alkyl group having 4 to 18 carbon atoms is preferable, and an alkyl group having 6 to 12 carbon atoms is more preferable.
- the cycloalkyl group having 3 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 .
- a cycloalkyl group having 4 to 18 carbon atoms is preferable, and a cycloalkyl group having 6 to 12 carbon atoms is more preferable from the viewpoint of dispersibility of particles.
- the alkenyl group having 2 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 .
- Alkenyl groups having 4 to 18 carbon atoms are preferable, and alkenyl groups having 6 to 12 carbon atoms are more preferable, from the viewpoint of dispersibility of .
- the aryl group having 6 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 .
- An aryl group having 6 to 18 carbon atoms is preferable, and an aryl group having 6 to 12 carbon atoms is more preferable from the viewpoint of the dispersibility of .
- the alkoxyalkyl group having 2 to 30 carbon atoms represented by R 4 or R 5 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 .
- An alkoxyalkyl group having 4 to 18 carbon atoms is preferable, and an alkoxyalkyl group having 6 to 12 carbon atoms is more preferable from the viewpoint of dispersibility of particles.
- the compound having the structure represented by the above formula (1) is preferably represented by the above formula (3) in terms of ease of synthesis and reactivity as a capping agent, etc., and is represented by the above formula (30). more preferably.
- the organic group having 1 to 30 carbon atoms represented by R 6 or R 7 is not particularly limited, and examples thereof include alkyl groups having 1 to 30 carbon atoms, Examples include cycloalkyl groups, alkenyl groups having 2 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, and alkoxyalkyl groups having 2 to 30 carbon atoms. Among them, an alkyl group having 1 to 30 carbon atoms is preferable.
- the alkyl group having 1 to 30 carbon atoms represented by R 6 or R 7 is not particularly limited, and examples thereof include the groups specifically exemplified for R 1 , and from the viewpoint of reactivity as a capping agent, etc. , methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl Alkyl groups having 1 to 6 carbon atoms such as tert-hexyl groups are preferred.
- the organic group having 1 to 30 carbon atoms represented by R 60 or R 70 is described as the organic group having 1 to 30 carbon atoms represented by R 6 or R 7 in the above formula (3). is the same as
- Examples of the compound represented by the above formula (3) include the following compounds. (Wherein, R 1 , R 2 , n1, n2, L, R 60 and R 70 are as defined above.)
- R represents an alkylene group having 1 to 3 carbon atoms
- R′ represents an alkyl group having 1 to 3 carbon atoms
- n is a number of 0 or more, for example, a number of 0 or more and 10 or less, preferably represents a number from 0 to 5.
- a compound having a structure represented by the above formula (1) can be produced using any organic synthesis reaction, for example, according to Scheme 1 below.
- the catalyst may be either an acid catalyst or an alkali catalyst.
- acid catalysts include inorganic acids, aliphatic sulfonic acids, aromatic sulfonic acids, aliphatic carboxylic acids, aromatic carboxylic acids, and specific examples include hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, , nitric acid, perchloric acid, phosphoric acid, methanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, maleic acid, fumaric acid, and benzoic acid.
- alkaline catalysts include methylamine, ethylamine, propylamine, butylamine, ethylenediamine, hexamethylenediamine, dimethylamine, diethylamine, ethylmethylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, cyclohexylamine, dicyclohexylamine, mono ethanolamine, diethanolamine, dimethylmonoethanolamine, monomethyldiethanolamine, triethanolamine, diazabicyclooctane, diazabicyclocyclononene, diazabicycloundecene, hexamethylenetetramine, aniline, N,N-dimethylaniline, pyridine, N , N-dimethylethanolamine, N,N-diethylethanolamine, N-( ⁇ -aminoethyl)ethanolamine, N-methylethanolamine, N-methyldiethanolamine, N-ethylethanolamine, Nn-
- the amount of the catalyst used is preferably 10 -6 mol to 10 mol, more preferably 10 -5 mol to 5 mol, still more preferably 10 -4 mol, per 1 mol of the compound represented by the above formula (6). ⁇ 1 mol.
- the amount of water used is preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, and still more preferably 0 mol per 1 mol of the group represented by OR 9 in the compound represented by the above formula (6). .1 to 30 mol, particularly preferably 0.5 to 5 mol.
- organic solvents examples include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, acetone, acetonitrile, tetrahydrofuran, toluene, hexane, ethyl acetate, cyclohexanone, Methyl amyl ketone, butanediol monomethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, butanediol monoethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether acetate ( PGMEA), propylene glycol monoethyl ether acetate, ethyl pyruvate, butyl acetate, methyl 3-methoxyprop
- the amount of the organic solvent used is preferably 0-1,000 ml, particularly preferably 0-500 ml, per 1 mol of the compound represented by the above formula (6).
- the reaction temperature is preferably 0 to 100°C, more preferably 5 to 80°C, and the reaction time is preferably 10 minutes to 3 hours, more preferably 20 to 1 hour.
- the compound represented by the above formula (3) can be produced, for example, according to Scheme 2 below.
- the organic group having 1 to 30 carbon atoms represented by R 8 is the same as the organic group having 1 to 30 carbon atoms represented by R 6 or R 7 in the above formula (3). It is the same.
- the organic group having 1 to 30 carbon atoms represented by R 9 is not particularly limited, and examples thereof include an alkyl group having 1 to 30 carbon atoms and a cycloalkyl group having 3 to 30 carbon atoms. , an alkenyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and an alkoxyalkyl group having 2 to 30 carbon atoms. Among them, an alkyl group having 1 to 30 carbon atoms is preferred.
- the alkyl group having 1 to 30 carbon atoms represented by R 9 is not particularly limited, and examples thereof include the groups specifically exemplified for R 6 or R 7 , and the ease of synthesis and OR 8 In terms of reactivity with groups, methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n- An alkyl group having 1 to 6 carbon atoms such as hexyl group, isohexyl group, sec-hexyl group and tert-hexyl group is preferable.
- the particles according to the present invention have a structure represented by formula (1) above. Since the above particles are excellent in dispersibility and refractive index, they can be suitably used as a high refractive index material.
- Particles having the structure represented by formula (1) on the surface are, for example, particles having no structure represented by formula (1) on the surface, and the structure represented by formula (1) is formed on the surface. It has an introduced form.
- Particles not having the structure represented by formula (1) on the surface are not particularly limited, and examples thereof include particles having hydroxyl groups on the surface.
- Particles having hydroxyl groups on their surfaces are not particularly limited, and examples thereof include metal oxide particles such as titanium oxide particles, zirconium oxide particles and hafnium oxide; and other particles having a high refractive index such as Si particles.
- the particle size of the particles according to the present invention is not particularly limited, and is preferably 1 to 20 nm, more preferably 2 to 15 nm, and even more preferably 4 to 10 nm in terms of dispersibility and the like.
- the particle size of a particle refers to the particle size measured by observing the particles with a TEM.
- the average diameter of the particles of the dispersion composition containing the particles according to the present invention can be measured with a dynamic light scattering (DLS) device such as Malvern Zetasizer Nano S.
- DLS dynamic light scattering
- the particles according to the present invention are dispersed in a dispersion medium such as PGMEA at a concentration of 5% by mass or less, the particles are monodisperse and the range of the average diameter is 20 nm or less.
- the dispersion composition according to the present invention has, for example, a combination of the particles according to the present invention and a known organic solvent or a known liquid monomer or the like, and maintains the dispersibility of the particles according to the present invention in the combination.
- the structure represented by formula (1) above binds to particles through at least one bond.
- the form of bonding between the structure represented by the above formula (1) and the particles is not particularly limited, and examples thereof include the following forms (F1a) and (F1b).
- the structure represented by the above formula (1) binds to particles through both bonds.
- the structure represented by the above formula (1) binds to the particles through one bond.
- Particles having a structure represented by formula (1) on their surface can be produced by, for example, a production method comprising a particle coating step (hereinafter also referred to as “production method 1”), or a first reaction step and and a second reaction step (hereinafter also referred to as “manufacturing method 2”).
- the particle coating step, the first reaction step, and the second reaction step can be performed, for example, in the absence or presence of a catalyst in water or a mixed solvent.
- a catalyst in water or a mixed solvent.
- Examples of catalysts, organic solvents, reaction temperatures, and reaction times are the same as described in Scheme 1.
- Production method 1 can be carried out, for example, according to Scheme 3 or 4 below.
- the amount of the catalyst used is preferably 10 -6 mol to 10 mol, more preferably 10 -5 mol to 5 mol, still more preferably 10 -4 mol, per 1 mol of the compound represented by the above formula (3). ⁇ 1 mol.
- the amount of water used is preferably 0.01 to 100 mol, more preferably 0 mol per 1 mol of the group represented by OR 6 and the group represented by OR 7 in the compound represented by the above formula (3).
- the amount of the organic solvent used is preferably 0 to 1,000 ml, particularly preferably 0 to 500 ml, per 1 mol of the compound represented by the above formula (3).
- R 6 is preferably a group represented by L(R 2 ) n1 (O) n2 .
- the amount of water used is preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, still more preferably 0 mol per 1 mol of the group represented by OR 7 in the compound represented by the above formula (3). .1 to 30 mol.
- Production method 2 can be carried out, for example, according to Scheme 5 below.
- the amount of the catalyst used is, for the first reaction step, per mol of the compound represented by the above formula (4), or for the second reaction step, the compound represented by the above formula (6) It is preferably from 10 ⁇ 6 mol to 10 mol, more preferably from 10 ⁇ 5 mol to 5 mol, still more preferably from 10 ⁇ 4 mol to 1 mol, per 1 mol.
- the amount of water used in the first reaction step is per 1 mole of the group represented by OR 60 and the group represented by OR 70 in the compound represented by the above formula (4), or the second In the case of the reaction step of , preferably 0.01 to 100 mol, more preferably 0.05 to 50 mol, still more preferably It is 0.1 to 30 mol, particularly preferably 1 to 5 mol.
- the amount of the organic solvent used is represented by 1 mol of the compound represented by the above formula (4) in the case of the first reaction step, or by the above formula (6) in the case of the second reaction step 0 to 1,000 ml is preferable, and 0 to 500 ml is particularly preferable, with respect to 1 mol of the compound.
- the reaction temperature is preferably 0 to 100°C, more preferably 5 to 80°C, and the reaction time is preferably 10 minutes to 3 hours, more preferably is 20-1 hour.
- a compound represented by 4-A below (hereinafter also referred to as “compound 4-A”) and a compound represented by 6-A below (hereinafter also referred to as “compound 6-A”) were mixed for 60 minutes. , hydrolytically condensed at room temperature. The molar ratio of compound 4-A and compound 6-A was 1:1.
- compound 4-A or compound 6-A was not observed when subjected to GPC after being placed under the above conditions alone. A new peak appeared. The polystyrene-equivalent number-average molecular weight of this new peak was calculated to be 1,300.
- the centrifuged coated particles were collected, dispersed in tetrahydrofuran (THF), heptane was added to precipitate the coated particles, and then centrifuged. (Indicated as 2 in the row of washing conditions in Table 1.) 3.
- the centrifuged coated particles were collected again, dispersed in tetrahydrofuran (THF), heptane was added to precipitate the coated particles, and then centrifuged. (Indicated as 3 in the row of washing conditions in Table 1.)
- ⁇ XPS X-ray photoelectron spectroscopy
- the filtered coated particles were re-dispersed in a dispersion medium: PGMEA to prepare a 50% by mass dispersion. This dispersion is subjected to thermogravimetric analysis (TGA) to calculate the total ratio of the portion derived from compound 6-A and the portion derived from compound 4-A to the solid content in the dispersion, and the coated particles was used as the coverage (mass%). Table 1 shows the results.
- ⁇ Refractive index The higher the content of titanium in the portion of the coated particles where the titanium oxide particles are coated (that is, the sum of the portion derived from compound 6-A and the portion derived from compound 4-A), The refractive index of the coated particles is more likely to improve. Since titanium is contained in the portion derived from compound 6-A, it can be rationally understood that the larger the amount of the portion derived from compound 6-A, the easier it is to improve the refractive index of the coated particles. . Therefore, the refractive index of the coated particles is calculated using the molar ratio of the portion derived from compound 6-A and the portion derived from compound 4-A (hereinafter also referred to as "compound 6-A/compound 4-A") obtained by XPS. Evaluation was made according to the following criteria.
- Table 1 shows the results. ++ (very good): Compound 6-A/Compound 4-A was 0.5 or more. + (good): compound 6-A/compound 4-A was more than 0 and less than 0.5. - (bad): compound 6-A/compound 4-A was 0. Alternatively, the dispersibility of the coated particles was poor.
- ⁇ Particle size in the dispersion composition Each coated particle of Examples 1 to 5 was dispersed in a dispersion medium such as PGMEA at a concentration of 5% by mass or less to obtain a dispersion composition, and a Malvern Zetasizer Nano S (dynamic light scattering ( DLS) apparatus) was used to measure the average diameter of the coated particles in the dispersion composition. As a result, the average diameter was 20 nm or less for all of Examples 1-5.
- a dispersion medium such as PGMEA at a concentration of 5% by mass or less
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Abstract
Description
R1は、炭素原子数1~30の有機基を表し、
R2は、OR3で表される基、又は下記式(2)で表される基を表し、
R3は、炭素原子数1~30の有機基を表し、
n1及びn2は、それぞれ独立に、0以上の整数を表し、但し、n1+2×n2は、Lの種類により決まる価数であり、
Lは、アルミニウム、ガリウム、イットリウム、チタン、ジルコニウム、ハフニウム、ビスマス、スズ、バナジウム、又はタンタルを表し、
*は結合手を表す。)
前記製造方法は、
水酸基を表面に有する粒子を、下記式(30)で表される化合物と反応させて、上記式(1)で表される構造を表面に有する粒子を得る粒子被覆工程
を有し、又は、
前記製造方法は、
水酸基を表面に有する粒子を、下記式(4)で表される化合物と反応させて、下記式(5)で表される構造を表面に有する粒子を得る第一の反応工程と、
第一の反応工程で得た粒子を、下記式(6)で表される化合物と反応させて、上記式(1)で表される構造を表面に有する粒子を得る第二の反応工程と、
を有する
製造方法。
本発明に係る化合物は、上記式(1)で表される構造を有する。上記化合物は、分散性及び屈折率に優れる粒子を与えるキャッピング剤として用いることができる。
(式中、Rは炭素原子数1~3のアルキレン基を表し、R’は炭素原子数1~3のアルキル基を表し、nは0以上の数、例えば、0以上10以下の数、好ましくは0以上5以下の数を表す。)
本発明に係る粒子は、上記式(1)で表される構造を有する。上記粒子は、分散性及び屈折率に優れるため、高屈折率材料に好適に用いることができる。
式(1)で表される構造を表面に有する粒子は、例えば、上述の通り、粒子被覆工程を有する製造方法(以下、「製造方法1」ともいう。)、又は、第一の反応工程と第二の反応工程とを有する製造方法(以下、「製造方法2」ともいう。)により製造することができる。
下記4-Aで表される化合物(以下、「化合物4-A」ともいう。)と下記6-Aで表される化合物(以下、「化合物6-A」ともいう。)とを、60分間、室温で加水分解縮合させた。化合物4-Aと化合物6-Aとのモル比は、1:1であった。加水分解縮合後の反応混合物をゲルパーミエーションクロマトグラフィー(GPC)に供したところ、化合物4-A又は化合物6-Aを単独で上記条件下に置いた後にGPCに供した場合には観察されなかった新規ピークが出現した。この新規ピークについて、ポリスチレン換算の数平均分子量を算出したところ、1300であった。上述の結果及び1H-NMR測定の結果から、上記新規ピークに該当する生成物として、下記3-Aで表される化合物が得られたことが確認された。なお、上記新規ピークは肩を有しており、その肩に基づき算出されるポリスチレン換算の数平均分子量から、下記3-Bで表される化合物が生成していることも確認された。また、生成物を13C-NMR測定に供した結果においては、原料を同様の測定に供した際にはピークが現れなかった領域である5~7ppmにかけて、生成物中の(CH3O)1、(CH3O)2、又はSiCH2と考えられるピークが確認された。
(酸化チタン粒子の調製)
国際公開第2020/106860号の実施例8を参照して、酸化チタン粒子を回収した。酸化チタン粒子をTEMで観察したところ、形状は球形であり、粒径は7nmであった。表1において、上記酸化チタン粒子を「TiO2」と表記する。
20ccバイアル中で、表1に示す割合で、上記酸化チタン粒子と化合物4-Aとを混合した後、110℃で30分間、撹拌した。その後、上記バイアル中に、更に、化合物6-Aを添加し、110℃で20分間、撹拌して、被覆粒子を得た。なお、比較例1では、この段階で、ゲル化してしまい、続く評価を行えなかった。また、上記反応は、PGMEA中で行った。また、被覆粒子の洗浄条件を以下のように場合分けした。
1.PGMEAを含む反応系中にn-ヘプタンを添加して、被覆粒子を沈殿させた後、遠心分離した。(表1中の洗浄条件の行において、1と示す。)
2.次いで、遠心分離した被覆粒子を採取後、テトラヒドロフラン(THF)で分散し、ヘプタンを添加して、被覆粒子を沈殿させた後、遠心分離した。(表1中の洗浄条件の行において、2と示す。)
3.再度、遠心分離した被覆粒子を採取後、テトラヒドロフラン(THF)で分散し、ヘプタンを添加して、被覆粒子を沈殿させた後、遠心分離した。(表1中の洗浄条件の行において、3と示す。)
・分散性
濾別した被覆粒子について、洗浄液:n-ヘプタンによる洗浄、濾別後に25℃での乾燥、分散媒:PGMEAへの再分散、及び濾過を試みた。
被覆粒子の分散性を下記の基準で評価した。結果を表1に示す。
+(良好):洗浄、乾燥、再分散、及び濾過の全てが可能であった。
-(不良):被覆粒子はゲル化しており、洗浄、乾燥、再分散、及び濾過の少なくとも1つが不可能であり、以降の測定はできなかった。
調製した被覆粒子について、X線光電子分光分析(XPS分析)を行い、当該被覆粒子に含まれるリンとケイ素とのモル比を算出し、更に、それに基づき、当該被覆粒子において、化合物6-Aに由来する部分と化合物4-Aに由来する部分とのモル比を算出した。結果を表1に示す。
濾別した被覆粒子を分散媒:PGMEAに再分散させ、50質量%の分散液を調製した。この分散液について、熱重量分析(TGA)を行い、該分散液中の固形分に占める化合物6-Aに由来する部分及び化合物4-Aに由来する部分の合計の割合を算出し、被覆粒子の被覆率(質量%)とした。結果を表1に示す。
被覆粒子中で酸化チタン粒子を被覆している部分(即ち、化合物6-Aに由来する部分と化合物4-Aに由来する部分との合計)において、チタンの含有量が多いほど、被覆粒子の屈折率がより向上しやすい。チタンは化合物6-Aに由来する部分に含まれているので、化合物6-Aに由来する部分の量が多いほど、被覆粒子の屈折率がより向上しやすくなると合理的に理解することができる。そこで、被覆粒子の屈折率を、XPSによる化合物6-A由来部分と化合物4-A由来部分とのモル比(以下、「化合物6-A/化合物4-A」ともいう。)を用いて、下記の基準で評価した。結果を表1に示す。
++(極めて良好):化合物6-A/化合物4-Aが0.5以上であった。
+(良好):化合物6-A/化合物4-Aが0超0.5未満であった。
-(不良):化合物6-A/化合物4-Aが0であった。又は、被覆粒子の分散性が不良であった。
実施例1~5各々の被覆粒子を5質量%以下の濃度でPGMEA等の分散媒中に分散させて分散組成物を得、Malvern Zetasizer Nano S(動的光散乱(DLS)装置)により、該分散組成物における上記被覆粒子の平均径を測定した。その結果、平均径は、実施例1~5のいずれについても20nm以下であった。
Claims (6)
- 請求項4に記載の粒子を含む、分散組成物。
- 下記式(1)で表される構造を表面に有する粒子の製造方法であって、
前記製造方法は、
水酸基を表面に有する粒子を、下記式(30)で表される化合物と反応させて、下記式(1)で表される構造を表面に有する粒子を得る粒子被覆工程
を有し、又は、
前記製造方法は、
水酸基を表面に有する粒子を、下記式(4)で表される化合物と反応させて、下記式(5)で表される構造を表面に有する粒子を得る第一の反応工程と、
第一の反応工程で得た粒子を、下記式(6)で表される化合物と反応させて、下記式(1)で表される構造を表面に有する粒子を得る第二の反応工程と、
を有する
製造方法。
R1は、炭素原子数1~30の有機基を表し、
R2は、OR3で表される基、又は下記式(2)で表される基を表し、
R3は、炭素原子数1~30の有機基を表し、
n1及びn2は、それぞれ独立に、0以上の整数を表し、但し、n1+2×n2は、Lの種類により決まる価数であり、
Lは、アルミニウム、ガリウム、イットリウム、チタン、ジルコニウム、ハフニウム、ビスマス、スズ、バナジウム、又はタンタルを表し、
*は結合手を表す。)
R9O-L(R2)n1(O)n2 (6)
(式中、R2、n1、n2、及びLは、前記の通りであり、R9は、炭素原子数1~30の有機基を表す。)
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2010047452A (ja) * | 2008-08-22 | 2010-03-04 | Tohoku Univ | 無機骨格を有する高分子修飾ハイブリッドナノ粒子及びその合成方法 |
JP2016533533A (ja) * | 2013-09-23 | 2016-10-27 | ピクセリジェント・テクノロジーズ・エルエルシー | 高屈折率シリコーンナノ複合材 |
JP2019211773A (ja) * | 2018-06-04 | 2019-12-12 | Hoya Candeo Optronics株式会社 | 光学フィルターおよび撮像装置 |
WO2020106860A1 (en) * | 2018-11-20 | 2020-05-28 | Pixelligent Technologies Llc | Synthesis, capping, and dispersion of tio2 nanocrystals |
US20200255456A1 (en) * | 2014-12-05 | 2020-08-13 | Velox Flow, Llc | Multifunctional superhydrophobic particles for chemical adhesion and blooming |
Family Cites Families (1)
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010047452A (ja) * | 2008-08-22 | 2010-03-04 | Tohoku Univ | 無機骨格を有する高分子修飾ハイブリッドナノ粒子及びその合成方法 |
JP2016533533A (ja) * | 2013-09-23 | 2016-10-27 | ピクセリジェント・テクノロジーズ・エルエルシー | 高屈折率シリコーンナノ複合材 |
US20200255456A1 (en) * | 2014-12-05 | 2020-08-13 | Velox Flow, Llc | Multifunctional superhydrophobic particles for chemical adhesion and blooming |
JP2019211773A (ja) * | 2018-06-04 | 2019-12-12 | Hoya Candeo Optronics株式会社 | 光学フィルターおよび撮像装置 |
WO2020106860A1 (en) * | 2018-11-20 | 2020-05-28 | Pixelligent Technologies Llc | Synthesis, capping, and dispersion of tio2 nanocrystals |
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