WO2004092105A1 - Nouveaux monomeres acrylates, copolyacrylates multifonctionnalises perfluores durcissables aux uv et leurs procedes de synthese pour dispositifs photoniques - Google Patents

Nouveaux monomeres acrylates, copolyacrylates multifonctionnalises perfluores durcissables aux uv et leurs procedes de synthese pour dispositifs photoniques Download PDF

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Publication number
WO2004092105A1
WO2004092105A1 PCT/KR2004/000244 KR2004000244W WO2004092105A1 WO 2004092105 A1 WO2004092105 A1 WO 2004092105A1 KR 2004000244 W KR2004000244 W KR 2004000244W WO 2004092105 A1 WO2004092105 A1 WO 2004092105A1
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nmr
synthesis
yield
300mhz
title compound
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PCT/KR2004/000244
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English (en)
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Hwan-Kyu Kim
Bok-Joo Song
Jin-Kyu Bark
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Hwan-Kyu Kim
Bok-Joo Song
Jin-Kyu Bark
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Priority claimed from KR10-2004-0008113A external-priority patent/KR100538049B1/ko
Application filed by Hwan-Kyu Kim, Bok-Joo Song, Jin-Kyu Bark filed Critical Hwan-Kyu Kim
Publication of WO2004092105A1 publication Critical patent/WO2004092105A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
    • C08F222/1045—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate of aromatic tetraalcohols
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/0009—Materials therefor
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/02—Materials and properties organic material
    • G02F2202/022—Materials and properties organic material polymeric
    • G02F2202/023—Materials and properties organic material polymeric curable

Definitions

  • the present invention relates to monomers to develop new, UV-curable, fluorinated polyacrylate compounds for information and electronic devices, and more particularly to, new acrylate monomers and polymers which are fluorinated at the polymeric main chain and thus show low optical transmission loss at
  • PMMA system has a T g of about 100 °C, which indicates low thermal stability.
  • Japan' s NTT developed and presented a deuterated polysiloxane (Electron. Lett., 30, 958 (1994)), and a fluorinated polyimide.
  • Fluorinated polyimide which was developed and commercialized for use in optical devices by Amoco Chemical Co. (USA) and sold under the trademark Ultradel 9000D, has problems of relatively high optical loss and high birefringence, but is designed to be photo-crosslinked such that it can be easily fabricated into optical devices by photolithography.
  • Allied Signal Co. USA
  • UV-curable fluorinated polyacrylate USP No. 6,306,563
  • thermo- optical devices having reliability in addition to this optical absorption characteristic
  • a multi-layer thin film must be able to be formed.
  • amorphous polymers need to be developed, which have excellent chemical resistance and thermal resistance, and low mechanical strength and dielectric properties and do not show optical absorption or scattering caused by the chemical structure itself .
  • the photocuring includes polymerization by the crosslinking of monomers or polymerization by radiation .
  • the polymerization mechanism can be described by radical or cationic polymerization, and radical initiation polymerization is most generally used.
  • Most of commercial photocuring systems consist of multifunctional acrylate monomers and a free radical photoinitia or .
  • the photocuring which utilizes ultraviolet rays , has many advantages, such as the simplification of a manufacturing process, and the reduction of costs . With a dramatic growth in electric and communication industries , the development of photocurable materials for optical waveguide and interconnect applications is urgently required.
  • polyacrylate- based compounds have been recently studied as optical waveguide- materials due to the low birefringence and optical loss of a wide - range of monomers .
  • halofluorinated acrylate which is a transparent monomer useful as a waveguide material having optical characteristics
  • the simplification of a process by direct irradiation and the improvement of thermal stability of a material still remain as problems to be solved.
  • FIG. 1 shows the IR spectrum of a (T4F8A/B4F8FA 70 : 30 ) copolymer, measured on a KBr pellet; and
  • FIG. 2 shows the absorption spectrum of photocrosslinked perfluorinated copolyacrylate in the near-infrared region .
  • An object of the present invention is to provide new fluorinated acrylate; monomers and polymers for optical waveguide materials , which have low birefringence , excellent thermal properties and very low optical transmission loss and used to develop UV-curable fluorinated polyacrylates , as well as methods for preparing them.
  • the present invention provides new fluorinated acrylate monomers and polymers for optical waveguide materials, as well as their preparation methods, which are described by chemical mechanisms in the following reaction schemes 1-13.
  • the concrete structure and preparing method of the monomers and polymers will be described in detail with reference to examples .
  • R f is one selected from and k is an integer selected from 2-10
  • Ri, R 2 , R 3 and R 4 which may be the same or different are each independently selected from the following group;
  • Ri, R 2 , R3, 4f a, b, c and d are the same as defined above;
  • Rii r R22/ R33 and R44 which may be the same or different are each independently selected from the following group;
  • k is an integer selected from 2-10
  • Y is one selected from H, F, CF 3 , and CI; and the remaining substituent groups and repeating units are the same as defined above.
  • R is one selected from the following group
  • R f i one selected from where k ir 3 an integer selected from 2-10.
  • R f is the same as defined above ,
  • R f is the same as defined above, and R h is one selected
  • N,N-dimethyl formamide, tetrahydrofuran, methylene chloride and benzene which are commercially available from Sam Jun Chemical Co., was used after purification, and substances, such as chlorobenzene, p-toluenesulfonic acid, n-hexane, and ethyl acetate, were used without separate purification.
  • the structure of prepared intermediates or monomers was examined by ⁇ -NMR, 13 C-NMR and FT-IR. The H-NMR results were recorded using a Varian 300 spectrometer, and all chemical shifts were recorded in ppm units per tetramethyl silane as the internal standard.
  • thermogravimetric analysis TGA
  • DSC differential scanning calorimetry
  • Example 1 Synthesis of 2, 2, 3, 3, 4 , 4 , 5, 5-octafluoro- ( 6- tetrahvdro-pyran-2-yloxy) -hexan-1-ol
  • reaction was terminated by the addition of triethylamine.
  • Example 7 Synthesis of tetrakis- ⁇ 4' - [6- (2-tetrahydro-pyranyloxy) - 2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy] -2,3,5,6,2' ,3' ,5' , 6' - octafluoro- (4-biphenoxy) ethyl ⁇ methane
  • Example 11 Synthesis of tetrakis- ⁇ 4' - [6- (2-tetrahydro- pyranyloxy) -2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy] -2,3,5,6- tetrafluoro- (4-tetrafluorophenyloxy) -phenoxymethyl ⁇ methane
  • Example 12 Synthesis of tetrakis- [4' - (6-hydroxy- 2,2, 3, 3,4,4, 5, 5, 6, 6-octafluorohexyloxy) -2, 3, 5, 6-tetrafluoro- (4- tetrafluorophenyloxy) -phenoxymethyl]methane
  • Example 13 Synthesis of tetrakis- [4' - (6-acryloxy- 2,2,3,3,4,4,5, 5-octafluorohexyloxy) -2,3,5, 6-tetrafluoro- (4- tetrafluorophenyloxy) -phenoxymethyl]methane
  • Example 15 Synthesis of tetrakis- ⁇ 4' - [ 6- (2-tetrahydro- pyranyloxy) -2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy] -2,3,5,6- tetrafluoro- (4-tetrafluorophenylsulfanyl) -phenoxymethyl ⁇ methane
  • Example 16 Synthesis of tetrakis- [4' - (6-hydroxy- 2,2,3,3,4,4, 5, 5, 6, 6-octafluorohexyloxy) -2,3,5, 6-tetrafluoro- (4- tetrafluorophenylsulfanyl) -phenoxymethyl] methane
  • Example 17 Synthesis of tetrakis- [ A ' ⁇ ( 6-acryloxy- 2,2,3,3,4,4,5, 5-octafluorohexyloxy) -2, 3, 5, 6-tetrafluoro- (4- tetrafluorophenylsulfanyl) -phenoxymethyl] methane
  • the title compound was prepared at a 70% yield in the same manner as in Example 5.
  • the titl'3 compound was prepared at a 40% yield in the same manner as in Example 2.
  • Example 19 Synthesis of tetrakis- ⁇ 4' - [6- (2-tetrahydro- pyranyloxy) -2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy] -2,3,5,6- tetrafluoro- (4-tetrafluorobenzenesulfonyl) -phenoxymethyl ⁇ methane
  • the title compound was prepared at a 97% yield in the same manner as in Example 3.
  • Example 22 Synthesis of tetrakis ⁇ 2, 3, 5, 6-tetraf luoro-4- (2,2,3,3,4,4,5, 5-octaf luoro-6-hexyloxy) -phenoxy ⁇ methylmethane The title compound was prepared at a 42% yield in the same manner as in Example 2.
  • Example 23 Synthesis of tetrakis- ⁇ ' - [6- (2-tetrahydro- pyranyloxy) -2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy] -2,3,5,6- tetrafluoro-4- (2,2,3,3,4, 4,5, 5-octafluoro-6-hexyloxy) - phenoxymethyl ⁇ methane
  • the title compound was prepared at a 97% yield in the same manner as in Example 3.
  • Example 24 Synthesis of tetrakis- [4' -( 6-hydroxy- 2,2,3,3,4,4,5,5,6, 6-octafluorohexyloxy) -2,3,5, 6-tetrafluoro-4- (2, 2,3,3,4,4,5, 5-octafluoro-6-hexyloxy) -phenoxymethyl] ethane
  • Example 25 Synthesis of tetrakis- [4' - (6-acryloxy- 2,2,3,3,4,4,5, 5-octafluorohexyloxy) -2,3,5, 6-tetrafluoro-4- (2,2,3,3,4,4,5, 5-octafluoro-6-hexyloxy) -phenoxymethyl] methane
  • Example 26j 4,4' -bis ( 6-hydroxy-2 ,2,3,3,4,4,5,5- octafluorohexyloxy) -2, 3, 5, 6, 2' , 3' , 5' , 6' -octafluorobiphenyl
  • Example 3_3 j Synthesis of 4,4' -bis ( 6-acryloxy- 2,2,3,3,4,4,5, 5-octafluorohexyloxy) -2,3,5, 6-tetrafluoro- (4- tetrafluorobenzenesulfonyloxy) phenyl
  • Copolymers of T4F8A/B4F8FA and T8F8A/B4F8FA were synthesized in the presence of a photoinitiator at various monomer molar ratios (10:90, 20:80, 30:70, 50:50, 70:30 and
  • the structure of the copolymers synthesized by the photocrosslinking was analyzed by. an FR-IR spectrometer. As shown in FIG. 1, the comparison of FT-IR spectrum between the monomer mixture (a) , the photoinitiator (b) and the thermal crosslinked copolymer (c) (which are sequentially shown from downward to upward on the figure) indicated that, in the case of the copolymer of T4F8A/B4F8FA with a monomer molar ratio of 70:30, the band at 1650 cm -1 by CH-stretching of the ethylene group of the monomers was remarkably reduced, and the conversion of the copolymer was 90%.
  • the refractive index and birefringence of the photocrosslinked perfluorinated copolyacrylate thin films having various monomer molar ratios were measured with a PCA-200 prism coupler at a wavelength of 1,550 n .
  • the results are given in Table below.
  • the refractive index w ⁇ s in a range from 1.441 to 1.400, and the birefringence of the typical copolymer (T4F8A/B4F8A 2 : 8) was 0.0002.
  • the molar ratio between the monomer T4F8A or T8F8A and the monomer B4F8FA was important, and as the molar ratio of the monomer B4F8FA to the monomer T4F8A or T8F8A was increased, the birefringence of the resulting polyacrylates was reduced.
  • the thermal stability of the synthesized copolymers was analyzed with a thermogravimetric analyzer (TGA) in a nitrogen atmosphere.
  • TGA thermogravimetric analyzer
  • the glass transition temperature (T g ) of the copolymer was not measured.
  • Example 38 Synthesis of binder polymer (F9BPH-HPP) I
  • binder polymer F9BPH-HPP
  • 1.0 g (0.79' mmol) of 2,2,3,3,4,4,5, 5-octafluoro-6- (2, 3, 5, 6, 2', 3', 4', 5', 6' -nonafluoro- biphenyl-4-yloxy) -hexyl acrylate and 2-hydroxy-3-phenoxy propyl acrylate were dissolved in 3 ml of anhydrous benzene under a nitrogen stream, to which 5 mg of azobisisobutyronitrile was
  • the synthesized polymer had a number-average molecular weight of 5.7 x 10 4 (g/mol) and a molecular weight distribution of 4.0-4.9.
  • Example 39 Synthesis of binder polymer (F9BPH-HPP) II with reactivity Under a nitrogen stream, 1.0 g of binder polymer (F9BPH-HPP) I was dissolved in a solvent mixture of 20 ml dichloromethane and 2 ml pyridine, to which 0.15 ml of acryloyl chloride was then slowly added dropwise. The solution was stirred for 12 hours at room temperature. The reaction solution was put in an excess of methanol, stirred in an ice bath for one hour. Then, the methanol layer was separated, to which 50 ml of a mixed solution (1:1) of ethyl acetate and hexane was ' added. The solution was stirred for one hour at room temperature.
  • the produced precipitate was removed by filter paper, and ' the filtrate was freeze-dried to give 0.7 g (70% yield) of the binder polymer (F9BPH-HPP) II having reactivity.
  • the synthesized polymer had a molecular weight of 7.3 x 10 4 (g/mol) and a molecular weight distribution of 3.1-3.4.
  • the thermal stability of the synthesized polymer was analyzed with a thermogravimetric analyzer (TGA) under a nitrogen atmosphere.
  • TGA thermogravimetric analyzer
  • the reactor was allowed to cool and the reaction solution was precipitated in an . excess of methyl alcohol.
  • the produced precipitate was filtered and dried under vacuum, and then its weight was measured to calculate the polymerization yield.
  • 0.9 g (90% yield) of the binder polymer (HBP) was obtained.
  • the synthesized polymer had a number-average molecular weight of 3.3 x 10 4 (g/mol) and a molecular weight distribution of 3.1.
  • TGA thermogravimetric analyzer
  • a copolymer of polymer HBP III and a monomer mixture (T8F8A/B4F8FA) was synthesized in the presence of a photoinitiator while changing the weight ratio between the HBP III and the monomer mixture (T8F8A/B4F8FA) from 20:80 to 30:70, 50:50, 70:30 and 80:20.
  • the molar ratio between the monomers T8F8A and B4F8FA was 50:50, and as the photoinitiator, 1 wt% of 2-benzo- (1,3) dioxol-5-yl-4, 6-bis-trichloromethyl- (1,3,5) triazine (TA2-107) was used.
  • the polymer and monomers were dissolved in chlorobenzene of an amount corresponding to 80 wt% relative to the total weight of the polymer and monomers, and the mixture was filtered through a thin film filter of Teflon.
  • the resulting solution was spin-coated on a silicon wafer at a speed of 1,100 rpm for 30 seconds, and the coated thin film was left to stand in a vacuum oven for 12 hours to remove the solvent.
  • the synthesized copolymer was analyzed by an FR-IR spectrometer. The result showed that the band at 1650 cm -1 by CH-stretching of the ethylene group of the monomers was remarkably reduced, and the polymerization conversion was more than 90%.
  • the photocrosslinked perfluorinated copolyacrylate of 50wt% HBP III and 50 wt% monomer mixture (T8F8A/B4F8FA) (50:50 monomer molar ratio) was measured for its physical properties.
  • the refractive index and birefringence of the copolymer thin film were measured using a PCA-200 prism coupler at a 1,550 nm wavelength. The results showed that the copolymer thin film had a TE mode refractive index of 1.4468, a TM mode refractive index of 1.4563, and a birefringence of 0.0005.
  • the copolyacrylate containing no binder polymer (HBP) III had a birefringence of 0.0017 whereas the copolyacrylate containing the binder polymer (HBP) III had a reduced birefringence of 0.0005.
  • the thermal stability of the synthesized copolymers was analyzed with a thermogravimetric analyzer (TGA) under a nitrogen analyzer. The initial decomposition temperature
  • the present invention provides a variety of the fluorinated acrylate monomers and polymers, which satisfy properties required for low-loss optical waveguide materials and are used ' .to develop new UV-curable polyacrylate compounds .
  • the fluorinated polyacrylate compounds synthesized by the present invention have the following effects. Namely, they show minimized optical loss in the near-infrared region, since they contain fluorine. Also, they have low birefringence caused by the fine control of refractive index. Moreover, by virtue of the aromatic compound introduced into their molecule, they show increased thermal stability and allow a device fabrication process to be simplified by UV-curing. In addition, the inventive copolymers containing the binder polymer have various advantages, such as remarkably reduced refractive index and birefringence , increased thermal stability, low optical loss , and reduced synthetic costs .

Abstract

L'invention concerne des monomères destinés à élaborer de nouveaux composés de polyacrylate fluoré, durcissables aux ultraviolets (UV) conçus pour des dispositifs d'informations et électroniques. Plus précisément, l'invention concerne de nouveaux monomères et polymères acrylates fluorés, durcissables aux UV, représentés par les formules 1 ou 2 suivantes, qui sont fluorés au niveau de la chaîne polymère principale et qui présentent par conséquent une faible perte de transmission optique dans les zones de longueur d'onde de communication optique de 1,3 νm et 1,5 νm qui ont une faible biréfringence et une haute stabilité thermique du fait du réglage fin de l'indice de réfraction. L'invention concerne également un procédé permettant de les préparer.
PCT/KR2004/000244 2003-04-16 2004-02-07 Nouveaux monomeres acrylates, copolyacrylates multifonctionnalises perfluores durcissables aux uv et leurs procedes de synthese pour dispositifs photoniques WO2004092105A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2003-0024193 2003-04-16
KR20030024193 2003-04-16
KR10-2004-0008113A KR100538049B1 (ko) 2003-04-16 2004-02-06 자외선으로 경화가 가능한 정보·전자 소재용 불소 함유한 새로운 아크릴레이트 단량체, 중합체 및 그들의 제조 방법
KR10-2004-0008113 2004-02-06

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Cited By (4)

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JP2005170934A (ja) * 2003-11-21 2005-06-30 Chisso Corp フッ化アルキレンを有する重合性を有する液晶性化合物およびその重合体
WO2008026482A1 (fr) * 2006-08-29 2008-03-06 Asahi Glass Company, Limited Esters d'acides gras insaturés, et compositions de cristaux liquides polymérisables, matériaux optiquement anisotropes et éléments optiques, fabriqués en utilisant les esters
CN115710457A (zh) * 2022-11-10 2023-02-24 山西大学 一种紫外光固化组合物及其制备方法和应用
CN116004123A (zh) * 2022-12-20 2023-04-25 广州鹿山新材料股份有限公司 超耐水oca及其制备方法和应用

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JP2005170934A (ja) * 2003-11-21 2005-06-30 Chisso Corp フッ化アルキレンを有する重合性を有する液晶性化合物およびその重合体
JP4617837B2 (ja) * 2003-11-21 2011-01-26 チッソ株式会社 フッ化アルキレンを有する重合性を有する液晶性化合物およびその重合体
WO2008026482A1 (fr) * 2006-08-29 2008-03-06 Asahi Glass Company, Limited Esters d'acides gras insaturés, et compositions de cristaux liquides polymérisables, matériaux optiquement anisotropes et éléments optiques, fabriqués en utilisant les esters
CN115710457A (zh) * 2022-11-10 2023-02-24 山西大学 一种紫外光固化组合物及其制备方法和应用
CN115710457B (zh) * 2022-11-10 2023-09-22 山西大学 一种紫外光固化组合物及其制备方法和应用
CN116004123A (zh) * 2022-12-20 2023-04-25 广州鹿山新材料股份有限公司 超耐水oca及其制备方法和应用
CN116004123B (zh) * 2022-12-20 2023-08-22 广州鹿山新材料股份有限公司 超耐水oca及其制备方法和应用

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