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WO2025206490A1 - Composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (poss) ayant une nouvelle structure, son procédé de préparation et composition comprenant un composé oligomère - Google Patents

Composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (poss) ayant une nouvelle structure, son procédé de préparation et composition comprenant un composé oligomère

Info

Publication number
WO2025206490A1
WO2025206490A1 PCT/KR2024/014957 KR2024014957W WO2025206490A1 WO 2025206490 A1 WO2025206490 A1 WO 2025206490A1 KR 2024014957 W KR2024014957 W KR 2024014957W WO 2025206490 A1 WO2025206490 A1 WO 2025206490A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
silane
composition
poss
polyhedral oligomeric
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.)
Pending
Application number
PCT/KR2024/014957
Other languages
English (en)
Korean (ko)
Inventor
오상수
김명준
황모훈
전해리
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.)
Piocel Co ltd
Original Assignee
Piocel 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
Priority claimed from KR1020240130258A external-priority patent/KR20250148361A/ko
Application filed by Piocel Co ltd filed Critical Piocel Co ltd
Publication of WO2025206490A1 publication Critical patent/WO2025206490A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/32—Post-polymerisation treatment
    • C08G77/34—Purification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes

Definitions

  • Polysiloxane compounds are used in various industries due to their excellent advantages such as heat resistance, cold resistance, weather resistance, light resistance, chemical stability, electrical properties, flame retardancy, water resistance, transparency, colorability, non-stickiness, and non-corrosion.
  • the above-mentioned conventionally known polyhedral oligomeric silsesquioxane (POSS) compounds are all in the form where a functional group is substituted on a Si atom, and due to these multifunctional functional groups, the above-mentioned polyhedral oligomeric silsesquioxane (POSS) compounds are generally solid compounds, which makes it difficult to control the reaction and, in particular, has the problem of low handling and molding processability.
  • the present invention aims to provide a novel polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound having excellent weather resistance, physical properties, optical properties, chemical stability, low dielectric constant, handling properties, molding processability, etc., a method for producing the same, and a composition comprising the oligomer compound.
  • PES polyhedral oligomeric silsesquioxane
  • A can be expressed by the following general formula (2).
  • R 2 may be an alkyl group, preferably a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to C 15 , more preferably a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to C 5 .
  • a may be 8 to 24, and preferably a may be 8 to 20.
  • the new polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound represented by the general formula (1) above is an oligomer compound having a weight average molecular weight of 2,000 to 30,000, preferably 2,000 to 20,000.
  • composition comprising a polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane oligomer compound of the new structure of the present invention is characterized by comprising a polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane oligomer compound of the new structure represented by the general formula (1), a diluting monomer, an initiator, and an additive.
  • POSS polyhedral oligomeric silsesquioxane
  • novel polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound of the present invention and the composition containing the same can be applied to various industries, and in particular, it exhibits excellent heat resistance, thereby increasing its usability in industries such as electronic materials, optical materials, and electronic optical materials.
  • PES polyhedral oligomeric silsesquioxane
  • Figure 1 shows the structure of a typical POSS compound.
  • Figure 3 shows the NMR of a typical POSS compound.
  • FIG. 4 shows the NMR spectrum of a polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound of a novel structure obtained in Example 1 of the present invention.
  • PES polyhedral oligomeric silsesquioxane
  • Figure 5 is a typical device used in a method for producing a novel polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound having a new structure of the present invention.
  • PES polyhedral oligomeric silsesquioxane
  • R 3 is a substituted or unsubstituted alkyl group having C 1 to C 15 carbon atoms.
  • Examples of the above specific organo trialkoxy silane series compounds may include, but are not limited to, the following compounds.
  • the amount of the above organic trialkoxy silane to be used is 15 to 40 wt% of the total amount (weight parts, wt) of the catalyst, diluent, organic trialkoxy silane, and dialkyl dialkoxy silane or poly dialkyl siloxane, and is preferably 20 to 35 wt%.
  • the amount of the above dialkyl dialkoxy silane or poly dialkyl siloxane to be used may be 10 to 30 wt% of the total amount (weight parts, wt) of the catalyst, diluent, silane, and diol, and is preferably 15 to 30 wt%.
  • the above oligomeric compound produced by using the above organic trialkoxy silane:dialkyl dialkoxy silane or poly dialkyl siloxane mole ratio is such that a compound of “a” is produced according to the use of the organic trialkoxy silane:dialkyl dialkoxy silane or poly dialkyl siloxane mole ratio as the main produced compound, and a compound in which “a” exceeds 8 may also be produced together.
  • the size of the oligomeric compound of the present invention is expressed by weight average molecular weight, and the weight average molecular weight is an oligomeric compound of 2,000 to 30,000, preferably 2,000 to 20,000.
  • the above catalyst may use at least one selected from among catalysts including strong acids such as HCl, HNO 3 , and H 2 SO 4 ; strong bases such as NaOH, KOH, and BaOH ; and ammonium salts such as tetrabutylammonium acetate, TMAA (Tetra Methyl Ammonium Acetate), TMAF (Tetra Methyl Ammonium Fluoride), TEAH (Tetra Ethyl Ammonium Hydroxide), TEAA (Tetra Ethyl Ammonium Acetate), TEAF (Tetra Ethyl Ammonium Fluoride), TBAH (Tetra Butyl Ammonium Hydroxide), TBAA (Tetra Butyl Ammonium Acetate), and TBAF (Tetara Butyl Ammonium Fluoride).
  • strong acids such as HCl, HNO 3 , and H 2 SO 4
  • strong bases such as NaOH, KOH, and BaOH
  • ammonium salts such
  • the above (b) heating temperature increasing step is a step of increasing the reaction temperature of the reaction mixture of the above (a) raw material input step to 30 to 100°C, preferably 40 to 60°C.
  • the above (c) synthesis step is a step in which the reaction is continued while maintaining the reaction temperature raised in the above (b) heating and temperature raising step, and the diluted solvent and the alcohol, which are reaction by-products, that are volatilized as the reaction proceeds are recovered.
  • the recovery can be performed using a conventional method, and preferably, the volatile substances, the diluted solvent that is volatilized and the alcohol, which are reaction by-products, are condensed and recovered in a condenser using a recovery still adapter (see Fig. 5).
  • the addition of the above diluting solvent may be performed at a time of 1/3 to 1/2 of the total reaction time, in an amount of 5 to 30 wt%, preferably 10 to 20 wt%, of the initially used amount of solvent.
  • This additional addition of the diluting solvent has the advantage of ensuring the uniformity of the reaction by maintaining an appropriate diluting solvent concentration within the reactor.
  • the reaction time of the i) reaction step including the above step may be 24 to 200 hours. Preferably, it may be 24 to 150 hours. More preferably, it may be 24 to 100 hours.
  • vacuum purification is a step of cooling the polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane-based oligomer compound of the present invention, which is a new structure, to room temperature, and purifying it by removing excess diluting solvent, alcohol produced by the reaction, and water by vacuum, thereby finally obtaining the polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane-based oligomer compound of the present invention, which is a new structure, represented by the general formula (1) of the present invention, which is a reaction product.
  • PPS polyhedral oligomeric silsesquioxane
  • the above diluted solvent and unreacted reactants can be reused after purification.
  • Another aspect of the present invention is a composition comprising a polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound having a novel structure manufactured by the manufacturing method of the present invention, characterized in that it comprises a polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound having a novel structure represented by the general formula (1) as described above, a diluting monomer, an initiator, and, if necessary, an additive.
  • PES polyhedral oligomeric silsesquioxane
  • A can be expressed by the following general formula (2).
  • R 1 of the general formula (1) is a functional group including an epoxy group, a (meth)acrylic group, a vinyl group, a hydrolyzable silyl group, an oxetanyl group, a phenyl group, an aminoalkyl group, an alkoxy, an alkyl group, a halogen alkyl group, a hydroxyalkyl group (-(CH2)o-OH, where o can be 1 to 10), or a thiolalkyl group (-(CH2)o-SH, where o can be 1 to 10).
  • the diluted monomer as described above comprises 1 to 40 wt%, preferably 5 to 35 wt%, of the total composition.
  • One or more of the above initiators may be used, and the initiators may include, but are not limited to, the following compounds.
  • Benzyldimethylketal hydroxycyclohexylphenyl ketone, hydroxydimethylacetophenone, methyl-[methylthiophenyl]-morpholine propanone, 2,4-diethylthioxane ethone, ethyl-4-dimethyl aminobenzoate, benzophenol, 4-phenylbenzophenone, 2,4,6-trimethylbenzoyl-diphenyl phosphine, methylbenzyl formate, bis[4-n-alkyl](C10 ⁇ 13)phenyl]iodonium hexafluorophosphate, bis[a-n-alkyl](C10 ⁇ 13)phenyl]iodonium hexafluoroantimonate, bis(4-butylphenyl)iodium hexafluorophosphate, bis[4-n-alkyl(C10 ⁇ 13)phenyl]iodonium tetrakispentafluor
  • an appropriate initiator can be selected depending on the oligomer and monomer used.
  • a cationic UV initiator can be used, and for example, Iodonium-methylphenyl-methylpropylphenyl Hexafluoro-phosphate can be used.
  • the initiator comprises 0.1 to 5 wt%, preferably 1 to 5 wt%, of the total composition.
  • polysiloxanes (silicones additives), polyacrylates(acrylate additives), Polyether modification polysiloxane, Silicone macromers, Polymethylalkylsiloxanes, thermostable modified polysiloxane, Reactive silicones, polyether-modified dimethylsiloxanes
  • the composition of the present invention may further contain various additives such as a curing retardant for improving the preservation stability of the composition; an adhesion accelerator for improving the adhesive strength; an inorganic filler; a pigment; a fluorescent substance; a colorant; a heat resistance improver; a release agent; a dispersant for packaging; and the like, as needed.
  • composition of the present invention can also be used as a low-k material such as an OLED insulating material; a touch screen insulating material; an insulating material for a mobile phone antenna; an LED encapsulation material; etc.
  • composition of the present invention can also be used for medical purposes, such as hydro gel type adhesive medical patch materials containing drugs such as patches; contact lenses; medical adhesives; and silicone for insertion into the human body.
  • medical purposes such as hydro gel type adhesive medical patch materials containing drugs such as patches; contact lenses; medical adhesives; and silicone for insertion into the human body.
  • composition of the present invention can be used as a semiconductor encapsulation material such as EMC encapsulation of an ultra-thin semiconductor package, or as an optical material such as an optical adhesive; an optical fiber coating agent; a cladding material; and a wave guide resin.
  • a semiconductor encapsulation material such as EMC encapsulation of an ultra-thin semiconductor package
  • an optical material such as an optical adhesive; an optical fiber coating agent; a cladding material; and a wave guide resin.
  • Example 1 ⁇ Preparation of a polyhedral oligomeric silsesquioxane (POSS) modified polysiloxane oligomer compound having a novel structure of the present invention>
  • PPS polyhedral oligomeric silsesquioxane
  • the reaction temperature of the reaction mixture to which the catalyst was added was increased to 50°C and the reaction was carried out.
  • the reaction temperature was maintained at 50°C, and MeOH and IPA volatilized during the reaction were recovered.
  • IPA which was a diluting solvent, was removed from the reaction mixture, thereby obtaining 280 g of the target product, a polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane-based oligomer compound having a novel structure of the present invention (yield: 83%).
  • the weight average molecular weight of the obtained target product is 2,432.
  • the above 1), and 2) are added to a reactor and stirred at room temperature until completely transparent, thereby preparing a resin oligomer solution (1).
  • the above 3), and 4) are added to another reactor and stirred at room temperature until completely transparent, thereby preparing a semi-finished product solution (2) with an additive added and stirred.
  • the above solutions (1) and (2) are mixed, stirred at room temperature, and then filtered to prepare a composition (A1).
  • the monomer ratio of the above solutions (1) and (2) is 1:1.
  • the above 1), 3), 4), and 5) are added to a reactor and stirred at room temperature until completely transparent, thereby preparing a resin oligomer solution (1).
  • the above 2), 6), 7), and 8) are added to another reactor and stirred at room temperature until completely transparent, thereby preparing a semi-finished product solution (2) with an additive added and stirred.
  • the above solutions (1) and (2) are mixed, stirred at room temperature, and then filtered to prepare a composition (A2).
  • composition (B1) was obtained by proceeding in the same manner as in 1), except that a compound represented by the following chemical formula (b), which is a conventional basket-type silsesquioxane resin (conventional POSS oligomer) compound, was used instead of the polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane-based oligomer compound having a novel structure of the present invention as the resin oligomer.
  • a compound represented by the following chemical formula (b) which is a conventional basket-type silsesquioxane resin (conventional POSS oligomer) compound, was used instead of the polyhedral oligomeric silsesquioxane (POSS, polyhedral oligomeric silsesquioxane) modified polysiloxane-based oligomer compound having a novel structure of the present invention as the resin oligomer.
  • composition of Comparative Example 1 (Composition B1) and the composition of Example 2 (Composition A1) were coated on a slide glass, a PET (Polyethylene Terephthalate) film was covered thereon, and after curing with UV, the PET film was pulled in the 180° direction to the attached surface to measure the initial peel-off force.
  • the conditions of the slide glass, PET film, coating thickness, and UV light intensity are as follows.
  • composition B1 manufactured by the method of Comparative Example 1
  • composition A1 manufactured by the method of Example 2, respectively, and the measurement results are shown in Table 3 below.
  • composition of Comparative Example 1 As shown in Table 3, which is the result of the adhesion test, the composition of Comparative Example 1 (Composition B1) was coated and cured, and as a result of the 180° peel off test, cracks occurred on the coated surface immediately after curing, or peeling occurred after curing. From the above results, the composition of Comparative Example 1 (Composition B1) peeled off with only a very weak force of 1.0 g f /cm.
  • composition A1 the adhesive strength of the composition of Example 2 of the present invention is about 15 times stronger than that of the composition of Comparative Example 1 (Composition B1).
  • composition of Comparative Example 1 (Composition B1) and the composition of Example 2 (Composition A1) were coated on PET film, and after UV curing, the cured film was bent to measure the maximum radius of curvature without cracking. That is, the measurement of the inner radius of curvature is to measure the minimum radius of curvature without cracking when the coated specimen is rolled and folded so that the coating surface is inward. Starting from a radius of curvature of 20 mm, the radius of curvature is reduced in 1 mm units and measured by folding it down to 0.5 mm. The smaller the radius of curvature, the greater the flexibility of the composition.

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

Abstract

La présente invention concerne : un composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (POSS) ayant une nouvelle structure, qui est un corps modifié par silsesquioxane oligomère polyédrique (POSS) qui est un composé à base de polysiloxane ; son procédé de préparation ; et une composition comprenant le composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (POSS) ayant une nouvelle structure.
PCT/KR2024/014957 2024-03-27 2024-10-02 Composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (poss) ayant une nouvelle structure, son procédé de préparation et composition comprenant un composé oligomère Pending WO2025206490A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20240042048 2024-03-27
KR10-2024-0042048 2024-03-27
KR10-2024-0130258 2024-09-25
KR1020240130258A KR20250148361A (ko) 2024-03-27 2024-09-25 새로운 구조의 다면체 올리고머 실세스퀴옥산(POSS, polyhedral oligomeric silsesquioxane) 변성체 폴리실록산계 올리고머 화합물, 이의 제조방법, 및 상기 올리고머 화합물을 포함하는 조성물

Publications (1)

Publication Number Publication Date
WO2025206490A1 true WO2025206490A1 (fr) 2025-10-02

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ID=97215546

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Application Number Title Priority Date Filing Date
PCT/KR2024/014957 Pending WO2025206490A1 (fr) 2024-03-27 2024-10-02 Composé oligomère à base de polysiloxane modifié par silsesquioxane oligomère polyédrique (poss) ayant une nouvelle structure, son procédé de préparation et composition comprenant un composé oligomère

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Country Link
WO (1) WO2025206490A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020009018A (ko) * 2000-07-22 2002-02-01 김충섭 균일하게 분산된 다이메틸실록산을 포함하는폴리메틸실세스퀴옥산 공중합체의 제조방법
KR20020079075A (ko) * 2001-04-13 2002-10-19 이진규 폴리메틸실세스퀴옥산 공중합체와 이를 이용한 저유전성절연막 및 그 제조방법
KR20060012264A (ko) * 2003-03-11 2006-02-07 짓쏘 세끼유 가가꾸 가부시키가이샤 실세스퀴옥산 유도체를 이용하여 얻어지는 중합체
JP2013035918A (ja) * 2011-08-05 2013-02-21 Nagase Chemtex Corp ハードコート用組成物
KR20240014705A (ko) * 2022-07-26 2024-02-02 주식회사 파이오셀 신규한 meta-POSS(meta-polyhedral oligomeric silsesquioxane) 화합물, 이의 제조방법, 및 이의 제조방법으로 제조된 meta-POSS(meta-polyhedral oligomeric silsesquioxane) 화합물을 포함하는 조성물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020009018A (ko) * 2000-07-22 2002-02-01 김충섭 균일하게 분산된 다이메틸실록산을 포함하는폴리메틸실세스퀴옥산 공중합체의 제조방법
KR20020079075A (ko) * 2001-04-13 2002-10-19 이진규 폴리메틸실세스퀴옥산 공중합체와 이를 이용한 저유전성절연막 및 그 제조방법
KR20060012264A (ko) * 2003-03-11 2006-02-07 짓쏘 세끼유 가가꾸 가부시키가이샤 실세스퀴옥산 유도체를 이용하여 얻어지는 중합체
JP2013035918A (ja) * 2011-08-05 2013-02-21 Nagase Chemtex Corp ハードコート用組成物
KR20240014705A (ko) * 2022-07-26 2024-02-02 주식회사 파이오셀 신규한 meta-POSS(meta-polyhedral oligomeric silsesquioxane) 화합물, 이의 제조방법, 및 이의 제조방법으로 제조된 meta-POSS(meta-polyhedral oligomeric silsesquioxane) 화합물을 포함하는 조성물

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