KR20080047731A - Transparent heat-resistant composition and preparing method thereof - Google Patents
Transparent heat-resistant composition and preparing method thereof Download PDFInfo
- Publication number
- KR20080047731A KR20080047731A KR1020060117567A KR20060117567A KR20080047731A KR 20080047731 A KR20080047731 A KR 20080047731A KR 1020060117567 A KR1020060117567 A KR 1020060117567A KR 20060117567 A KR20060117567 A KR 20060117567A KR 20080047731 A KR20080047731 A KR 20080047731A
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- parts
- resin composition
- group
- transparent heat
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title abstract description 4
- 239000011342 resin composition Substances 0.000 claims abstract description 44
- 239000000178 monomer Substances 0.000 claims abstract description 42
- -1 aromatic vinyl compound Chemical class 0.000 claims abstract description 40
- 229920006015 heat resistant resin Polymers 0.000 claims abstract description 32
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000003287 optical effect Effects 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000012769 display material Substances 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000003607 modifier Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 claims description 2
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 claims description 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 2
- KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 claims description 2
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 claims description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 2
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 claims description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical compound FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 claims description 2
- ULYIFEQRRINMJQ-UHFFFAOYSA-N 3-methylbutyl 2-methylprop-2-enoate Chemical compound CC(C)CCOC(=O)C(C)=C ULYIFEQRRINMJQ-UHFFFAOYSA-N 0.000 claims description 2
- GQEFPXSNRRKUHO-UHFFFAOYSA-N 4-methylpent-1-enylbenzene Chemical compound CC(C)CC=CC1=CC=CC=C1 GQEFPXSNRRKUHO-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000005453 pelletization Methods 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims 2
- 239000002994 raw material Substances 0.000 claims 2
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 claims 1
- KUOHXNJVGHDRIZ-UHFFFAOYSA-N 3,3-dichloroprop-2-enenitrile Chemical compound ClC(Cl)=CC#N KUOHXNJVGHDRIZ-UHFFFAOYSA-N 0.000 claims 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000005520 cutting process Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- UZVPIXBMGPDIIQ-UHFFFAOYSA-N tert-butyl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)(C)C UZVPIXBMGPDIIQ-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B9/00—Making granules
- B29B9/02—Making granules by dividing preformed material
- B29B9/06—Making granules by dividing preformed material in the form of filamentary material, e.g. combined with extrusion
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/026—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising acrylic acid, methacrylic acid or derivatives thereof
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
본 발명은 투명 내열 수지 조성물 및 그 제조방법에 관한 것으로, 보다 상세하게는 투명성, 내열성 및 가공성이 모두 우수하여 광학용 및 디스플레이용 소재로 적합한 투명 내열 수지 조성물 및 그 제조방법에 관한 것이다.The present invention relates to a transparent heat-resistant resin composition and a method for manufacturing the same, and more particularly, to a transparent heat-resistant resin composition and a method for producing the same, which are excellent in transparency, heat resistance and processability, suitable for optical and display materials.
방향족 비닐 화합물과 메타크릴레이트계 단량체의 공중합체는 투명성, 가공성 및 기계적 물성의 밸런스가 우수하고, 폴리카보네이트 수지보다 가격이 저렴하여 가장 널리 이용되는 투명수지 중 하나에 속한다. 그러나, 도광판, 확산판 등의 디스플레이용 소재나 조명기구, 광학용 렌즈 등 내열성이 특히 요구되는 소재에서는 그 사용이 제한적이었다.Copolymers of aromatic vinyl compounds and methacrylate monomers have excellent balance of transparency, processability and mechanical properties, and are inexpensive than polycarbonate resins and thus belong to one of the most widely used transparent resins. However, its use has been limited in display materials such as light guide plates and diffusion plates, and materials requiring particularly heat resistance such as lighting devices and optical lenses.
이러한 공중합체에 내열성을 부여하기 위한 방법으로 미국특허 제4,558,098호(2001.01.02 공개) 및 제6,916,951호(2003.11.13 공개)에서는 메틸 메타크릴레이트, 스티렌 또는 알파 메틸 스티렌, 및 무수 말레인산을 공중합시키는 방법에 대하여 개시하고 있다. 상기 방법은 유리전이온도 및 열변형온도를 증가시킬 수 있는 효과가 있으나, 열에 의한 변색이 쉽게 발생하여 투명성을 저하시킬 수 있고, 일정 한 메틸 메타크릴레이트와 스티렌의 조성비에 제한된다는 문제점이 있다.US Pat. Nos. 4,558,098 (published Jan. 02, 2001) and 6,916,951 (published Nov. 13, 2003) provide copolymerization of methyl methacrylate, styrene or alpha methyl styrene, and maleic anhydride. The method is disclosed. The method has an effect of increasing the glass transition temperature and the heat deformation temperature, but there is a problem that discoloration due to heat can easily occur to decrease the transparency, and is limited to a constant composition ratio of methyl methacrylate and styrene.
일본공개특허공보 제2002-328240호(2002.11.15 공개)에서는 메틸 메타크릴레이트, 스티렌 또는 알파 메틸 스티렌, 및 말레이미드를 공중합시키는 방법에 대하여 개시하고 있다. 그러나, 상기 방법에서 말레이미드로 페닐말레이미드를 사용하는 경우에 페닐말레이미드(phenyl maleimide)의 노란색으로 인해 공중합체의 투명성이 저하되는 문제점이 있고, 시클로헥실말레이미드를 사용하는 경우에는 투명성을 저하시키지 않으면서 내열성을 어느 정도 향상시킬 수는 있으나, 고가이기 때문에 가격 경쟁력이 떨어진다는 문제점이 있다.Japanese Laid-Open Patent Publication No. 2002-328240 (published Nov. 15, 2002) discloses a method of copolymerizing methyl methacrylate, styrene or alpha methyl styrene, and maleimide. However, when the phenyl maleimide is used as the maleimide in the above method, there is a problem that the transparency of the copolymer is lowered due to the yellow color of phenyl maleimide, and when the cyclohexyl maleimide is used, the transparency is lowered. It is possible to improve the heat resistance to some extent without making it, but there is a problem that the price competitiveness is low because it is expensive.
일본공개특허공보 제 2006-137911(2006.06.01 공개)에서는 스티렌, 메틸 메타크릴레이트 및 메타크릴산의 공중합체를 제조하는 방법에 대하여 개시하고 있다. 그러나 상기 공중합체는 가공성이 좋지 않고, 후가공시 발포체, 가소제 등을 첨가하여 발포시트를 제조하고, 이를 식품용기로 사용하는 것으로써, 광학용 투명소재로서의 사용에는 제한적이라는 문제점이 있다.Japanese Laid-Open Patent Publication No. 2006-137911 (published on June 1, 2006) discloses a method for producing a copolymer of styrene, methyl methacrylate and methacrylic acid. However, the copolymer is poor in workability, and by adding a foam, a plasticizer, etc. in post-processing to prepare a foam sheet, and use it as a food container, there is a problem that it is limited to use as an optical transparent material.
따라서, 높은 투명성, 가공성 및 내열성을 가지고 있어 광학용 또는 디스플레이용 소재로 이용될 수 있는 투명 내열 수지로서 방향족 비닐 화합물과 메타크릴레이트계 단량체의 공중합체에 대한 연구가 더욱 필요한 실정이다.Therefore, as a transparent heat-resistant resin that has high transparency, processability and heat resistance and can be used as an optical or display material, further studies on copolymers of aromatic vinyl compounds and methacrylate monomers are needed.
상기와 같은 종래기술의 문제점을 해결하고자, 본 발명은 투명성, 가공성 및 내열성이 우수하여 광학용 또는 디스플레이용 소재로 적합한 투명 내열 수지 조성 물 및 그 제조방법을 제공하는 것을 목적으로 한다.In order to solve the problems of the prior art as described above, an object of the present invention is to provide a transparent heat-resistant resin composition and a method of manufacturing the same that are excellent in transparency, processability and heat resistance and suitable for optical or display materials.
본 발명의 상기 목적 및 기타 목적들은 하기 설명된 본 발명에 의하여 모두 달성될 수 있다.The above and other objects of the present invention can be achieved by the present invention described below.
상기 목적을 달성하기 위하여, 본 발명은 In order to achieve the above object, the present invention
a) ⅰ) 메틸 메타크릴레이트계 단량체 50 내지 87 중량부; ⅱ) 방향족 비닐화합물 10 내지 40 중량부; 및 ⅲ) 메타크릴산 단량체 3 내지 10 중량부;로 이루어지는 총 단량체 100 중량부; a) 50 to 87 parts by weight of iii) methyl methacrylate monomer; Ii) 10 to 40 parts by weight of an aromatic vinyl compound; And iii) 3 to 10 parts by weight of methacrylic acid monomers; 100 parts by weight of total monomers;
b) 분자량 조절제 0.1 내지 3.0 중량부; b) 0.1 to 3.0 parts by weight of a molecular weight modifier;
c) 폴리실록산 오일 0.01 내지 2.0 중량부; 및c) 0.01 to 2.0 parts by weight of polysiloxane oil; And
d) 용매 15 내지 100 중량부;를 포함하여 중합되는 것을 특징으로 하는 투명 내열 수지 조성물을 제공한다.d) 15 to 100 parts by weight of a solvent; to provide a transparent heat-resistant resin composition characterized in that the polymerization.
또한 본 발명은 상기 투명 내열 수지 조성물의 제조방법을 제공한다.The present invention also provides a method for producing the transparent heat resistant resin composition.
또한 본 발명은 상기 투명 내열 수지 조성물을 포함하는 광학용 및 디스플레이용 소재를 제공한다.The present invention also provides an optical material and a display material containing the transparent heat-resistant resin composition.
이하 본 발명을 상세하게 설명한다. Hereinafter, the present invention will be described in detail.
본 발명의 투명 내열 수지 조성물은, The transparent heat resistant resin composition of the present invention,
a) ⅰ) 아크릴레이트계 단량체 50 내지 87 중량부; ⅱ) 방향족 비닐화합물 10 내지 40 중량부; 및 ⅲ) 메타크릴산 단량체 3 내지 10 중량부;로 이루어지는 총 단량체 100 중량부; a) 50 to 87 parts by weight of acrylate monomer; Ii) 10 to 40 parts by weight of an aromatic vinyl compound; And iii) 3 to 10 parts by weight of methacrylic acid monomers; 100 parts by weight of total monomers;
b) 분자량 조절제 0.1 내지 3.0 중량부; b) 0.1 to 3.0 parts by weight of a molecular weight modifier;
c) 폴리실록산 오일 0.01 내지 2.0 중량부; 및c) 0.01 to 2.0 parts by weight of polysiloxane oil; And
d) 용매 15 내지 100 중량부;를 포함하여 중합되는 것을 특징으로 한다.d) 15 to 100 parts by weight of a solvent; characterized in that the polymerization.
본 발명에 사용되는 아크릴레이트계 단량체로는 메틸 아크릴레이트, 에틸 아크릴레이트, 프로필 아크릴레이트, 이소프로필 아크릴레이트, 부틸 아크릴레이트 등과 같은 알킬 아크릴레이트계 단량체, 메틸 메타크릴레이트, 에틸 메타크릴레이트, 프로필 메타크릴레이트, 이소프로필 메타크릴레이트, 부틸 메타크릴레이트, 이소부틸 메타크릴레이트, 이소아밀 메타크릴레이트 등과 같은 알킬 메타크릴레이트 단량체 등으로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있고, 바람직하게는 메타 메틸크릴레이트를 사용하는 것이다.The acrylate monomers used in the present invention include alkyl acrylate monomers such as methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, and propyl. At least one selected from the group consisting of alkyl methacrylate monomers such as methacrylate, isopropyl methacrylate, butyl methacrylate, isobutyl methacrylate, isoamyl methacrylate, and the like can be used, preferably Is using methyl methyl acrylate.
상기 메틸 메타크릴레이트계 단량체는 수지 조성물의 사용목적에 따라 그 함량을 조절하여 사용할 수 있지만, 통상적인 광학용 수지 조성물의 굴절율 범위를 고려할 때, 본 발명에 사용되는 총 단량체 100 중량부에 대하여 50 내지 87 중량부로 포함되는 것이 바람직하다. 그 함량이 50 중량부에 가까울수록 굴절율이 1.54에 근접하고, 87 중량부에 가까울수록 1.50에 근접한다. The methyl methacrylate monomer may be used by adjusting the content according to the purpose of use of the resin composition, but considering the refractive index range of a typical optical resin composition, 50 to 100 parts by weight of the total monomer used in the present invention It is preferably included to 87 parts by weight. The closer the content is to 50 parts by weight, the closer the refractive index is to 1.54, and the closer to the 87 parts by weight, to 1.50.
상기 메틸 메타크릴레이트계 단량체는 이와 공중합 가능한 단량체를 혼합하여 사용할 수 있다.The methyl methacrylate monomers may be used by mixing monomers copolymerizable therewith.
본 발명에 사용되는 방향족 비닐화합물로는 스티렌, α-메틸 스티렌, ο-메 틸 스티렌, ρ-메틸 스티렌, m-메틸 스티렌, 에틸 스티렌, 이소부틸 스티렌, t-부틸 스티렌, ο-브로보 스티렌, ρ-브로모 스티렌, m-브로모 스티렌, ο-클로로 스티렌, ρ-클로로 스티렌, m-클로로 스티렌, 비닐톨루엔, 비닐크실렌, 플루오로스티렌, 비닐나프탈렌 등으로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있고, 바람직하게는 스티렌을 사용하는 것이다.Aromatic vinyl compounds used in the present invention include styrene, α-methyl styrene, ο-methyl styrene, ρ-methyl styrene, m-methyl styrene, ethyl styrene, isobutyl styrene, t-butyl styrene, ο-brobo styrene , ρ-bromo styrene, m-bromo styrene, ο-chloro styrene, ρ-chloro styrene, m-chloro styrene, vinyltoluene, vinyl xylene, fluorostyrene, vinyl naphthalene, or the like May be used, and preferably styrene is used.
상기 방향족 비닐 화합물은 수지 조성물의 사용목적에 따라 함량을 조절하여 사용할 수 있지만, 통상적인 광학용 수지 조성물의 굴절율 범위를 고려할 때, 본 발명에 사용되는 총 단량체 100 중량부에 대하여 10 내지 40 중량부로 포함되는 것이 바람직하다. 그 함량이 10 중량부에 가까울수록 굴절률은 1.50에 근접하고, 40 중량부에 가까울수록 굴절률은 1.54에 근접한다.The aromatic vinyl compound may be used by adjusting the content according to the purpose of use of the resin composition, in consideration of the refractive index range of a conventional optical resin composition, 10 to 40 parts by weight based on 100 parts by weight of the total monomers used in the present invention It is preferred to be included. The closer the content is to 10 parts by weight, the closer the refractive index is to 1.50, and the closer to the 40 parts by weight, the closer to the refractive index is 1.54.
본 발명에 사용되는 메타크릴산 단량체로는 아크릴산 및 메타크릴산으로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있다.As methacrylic acid monomer used for this invention, 1 or more types chosen from the group which consists of acrylic acid and methacrylic acid can be used.
상기 메타크릴산 단량체는 그 함량이 증가함에 따라 유리전이온도가 증가하기 때문에 수지 조성물의 사용 목적에 따라 함량을 조절하여 사용할 수 있지만, 통상적인 광학용 수지 조성물의 굴절율 범위를 고려할 때, 본 발명에 사용되는 총 단량체 100 중량부에 대하여 3 내지 10 중량부로 포함되는 것이 바람직하다. 그 중량 범위 내에서 내열성 향상의 효과가 크고, 중합반응이 원활하게 진행되며, 시트 가공시 절단에 의한 파열불량을 개선할 수 있다.The methacrylic acid monomer may be used by adjusting the content according to the purpose of use of the resin composition because the glass transition temperature increases as the content thereof increases, in consideration of the refractive index range of a conventional optical resin composition, It is preferably included in 3 to 10 parts by weight based on 100 parts by weight of the total monomers used. Within the weight range, the effect of improving heat resistance is great, the polymerization reaction proceeds smoothly, and the failure of rupture due to cutting during sheet processing can be improved.
본 발명에 사용되는 분자량 조절제는 머캅탄계 화합물, 탄화수소염계 화합물, 아크롤레인, 알릴 알코올, 및 2-에틸 헥실 티오글리콜 등으로 이루어지는 군으 로부터 선택되는 1 종 이상을 사용할 수 있고, 바람직하게는 머캅탄계 화합물을 사용하는 것이며, 보다 바람직하게는 n-옥틸머캅탄을 사용하는 것이다.The molecular weight modifier used in the present invention may be one or more selected from the group consisting of mercaptan compounds, hydrocarbon salt compounds, acrolein, allyl alcohol, 2-ethyl hexyl thioglycol, and the like, and preferably mercaptan compounds. It is to use, More preferably, it uses n-octyl mercaptan.
상기 분자량 조절제는 본 발명에 사용되는 총 단량체 100 중량부에 대하여 0.1 내지 3.0 중량부로 포함되는 것이 바람직하다. 그 중량 범위 내에서 수지 조성물의 가공성 및 기계적 물성이 우수하다.The molecular weight modifier is preferably included in 0.1 to 3.0 parts by weight based on 100 parts by weight of the total monomers used in the present invention. Within the weight range, the processability and mechanical properties of the resin composition are excellent.
본 발명에 사용되는 폴리실록산 오일은 수지 조성물을 광학 또는 디스플레이 소재로 성형시 가공성을 향상시키는 역할을 한다. 상기 폴리실록산오일을 첨가함으로써 사출 성형시 이형성이 개선되고, 시트성형 절단시 파열에 의한 불량을 개선한다. The polysiloxane oil used in the present invention serves to improve processability when molding the resin composition into an optical or display material. By adding the polysiloxane oil, releasability is improved during injection molding, and defects due to rupture during sheet molding cutting are improved.
상기 폴리실록산 오일은 하기 화학식 1로 표시된 화합물을 구조반복단위로 하는 중합체인 것이 바람직하다.The polysiloxane oil is preferably a polymer having a compound represented by the following formula (1) as a structural repeating unit.
[화학식 1][Formula 1]
상기 화학식 1에서, x 및 y는 중합도이고, R1 내지 R4는 각각 수소원자, 탄소수 1 내지 5의 직쇄 또는 분지상의 알킬기, 사이클로헥실기를 포함하는 지환식 탄화수소기, 방향족기, 또는 상기 치환기들에 히드록시기, 알콕시기, 아미노기, 아미드기, 에폭시기, 카르복실기, 할로겐기 또는 에스테르기가 치환된 기들로 이루어 지는 군으로부터 선택될 수 있고, R1 내지 R4 중 적어도 1 종 이상은 페닐기를 가져야 한다.In Formula 1, x and y are degrees of polymerization, and R 1 to R 4 each represent a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, an alicyclic hydrocarbon group including a cyclohexyl group, an aromatic group, or the The substituents may be selected from the group consisting of hydroxy group, alkoxy group, amino group, amide group, epoxy group, carboxyl group, halogen group or ester group substituted, at least one of R 1 to R 4 should have a phenyl group .
상기 폴리실록산 오일은 수지 조성물의 굴절률에 따라 선택할 수 있다. 수지 조성물의 투명성이 저하되지 않기 위해서는 상기 폴리실록산 오일의 굴절율이 수지 조성물의 굴절률에 근접해야 하고, 수지 조성물과 상용성이 있어야 한다.The polysiloxane oil can be selected according to the refractive index of the resin composition. In order not to reduce the transparency of the resin composition, the refractive index of the polysiloxane oil must be close to the refractive index of the resin composition, and must be compatible with the resin composition.
상기 폴리실록산 오일의 굴절률은 통상적인 광학용 수지 조성물의 굴절률 범위를 고려할 때, 1.49 이상이 바람직하고, 보다 바람직하게는 1.50 이상이다. The refractive index of the polysiloxane oil is preferably 1.49 or more, more preferably 1.50 or more, in consideration of the refractive index range of a conventional optical resin composition.
상기 폴리실록산 오일의 점도는 100 내지 1500 cst인 것이 바람직하다. 그 점도 범위 내에서 이형성 및 가공성의 상승효과가 크고, 수지 조성물과의 상용성이 좋아 투명성이 우수하다.It is preferable that the viscosity of the said polysiloxane oil is 100-1500 cst. The synergistic effect of mold release property and workability is large within the viscosity range, and compatibility with a resin composition is good, and it is excellent in transparency.
상기 폴리실록산 오일의 사용량은 본 발명에 사용되는 총 단량체 100 중량부에 대하여 0.01 내지 2.0 중량부가 바람직하다. 그 함량이 0.01 중량부 이상인 경우에 충분한 개선효과를 얻을 수 있고, 2.0 중량부 이하인 경우에 투명성이 우수하다.The amount of the polysiloxane oil is preferably 0.01 to 2.0 parts by weight based on 100 parts by weight of the total monomers used in the present invention. When the content is 0.01 parts by weight or more, a sufficient improvement effect can be obtained, and when the content is 2.0 parts by weight or less, the transparency is excellent.
본 발명에 사용되는 용매는 중합 공정 중에 용액의 점도를 낮추고, 발열량을 제어하며, 중합전환율 및 총 고형분 함량(total solid content)을 조절하는 작용을 한다.The solvent used in the present invention serves to lower the viscosity of the solution during the polymerization process, to control the calorific value, and to control the polymerization conversion rate and the total solid content.
상기 용매는 에틸벤젠, 톨루엔, 벤젠 등과 같은 방향족 탄화수소; 메틸 에틸 케톤, 아세톤 등과 같은 케톤류; 사염화탄소, 디클로로메틸렌 등과 같은 할로겐화 탄화수소; 아세토니트릴; 및 디메틸 포름 아마이드 등으로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있고, 바람직하게는 톨루엔을 사용하는 것이다.The solvent may be an aromatic hydrocarbon such as ethylbenzene, toluene, benzene and the like; Ketones such as methyl ethyl ketone, acetone and the like; Halogenated hydrocarbons such as carbon tetrachloride, dichloromethylene and the like; Acetonitrile; And one or more selected from the group consisting of dimethyl formamide and the like, and preferably toluene is used.
상기 용매의 사용량은 본 발명에 사용되는 총 단량체 100 중량부에 대하여 15 내지 100 중량부로 포함되는 것이 바람직하다. 그 중량 범위 내에서 고분자 용액의 점도 및 발열을 제어하기 용이하여 공정의 운전이 원활하고, 중합전환율 및 총 고형분 함량이 높아 생산성이 우수하다.The amount of the solvent is preferably included in 15 to 100 parts by weight based on 100 parts by weight of the total monomer used in the present invention. It is easy to control the viscosity and heat generation of the polymer solution within the weight range, the operation of the process is smooth, the polymerization conversion rate and the total solid content is high, the productivity is excellent.
본 발명의 투명 내열 수지는 중량 평균분자량이 150,000 내지 350,000인 것이 바람직하다. 상기 범위 내에서 가공성 및 기계적 물성이 우수하다.The transparent heat resistant resin of the present invention preferably has a weight average molecular weight of 150,000 to 350,000. It is excellent in workability and mechanical properties within the above range.
본 발명의 투명 내열 수지 조성물의 제조방법은, The manufacturing method of the transparent heat resistant resin composition of this invention,
a) 총 단량체 100 중량부에 대하여 아크릴레이트계 단량체 50 내지 87 중량부, 방향족 비닐화합물 10 내지 40 중량부, 메타크릴산 단량체 3 내지 10 중량부 및 용매 10 내지 50 중량부를 혼합하여 단량체 용액을 제조하는 단계; a) a monomer solution is prepared by mixing 50 to 87 parts by weight of acrylate monomer, 10 to 40 parts by weight of aromatic vinyl compound, 3 to 10 parts by weight of methacrylic acid monomer and 10 to 50 parts by weight of solvent based on 100 parts by weight of the total monomers. Doing;
b) 상기 a)단계에서 제조한 단량체 용액을 2 개 이상의 교반 반응기가 직렬로 연결된 연속중합장치에 투입하여 공중합시키는 단계; b) copolymerizing the monomer solution prepared in step a) into a continuous polymerization apparatus in which two or more stirring reactors are connected in series;
c) 폴리실록산 오일 0.01 내지 2.0 중량부, 분자량 조절제 0.1 내지 3.0 중량부, 및 용매 5 내지 50 중량부를 혼합한 용액을 b)단계의 반응기에 연속투입하여 공중합시키는 단계; 및 c) copolymerizing a solution of 0.01 to 2.0 parts by weight of polysiloxane oil, 0.1 to 3.0 parts by weight of a molecular weight regulator, and 5 to 50 parts by weight of a solvent by continuously introducing into a reactor of step b); And
d) 상기 c)단계에서 생성된 공중합체를 펠렛화시키는 단계;를 포함하여 이루어지는 것을 특징으로 한다.d) pelletizing the copolymer produced in step c).
상기 a) 단계는 라디칼 중합개시제를 추가로 사용할 수 있다. Step a) may further use a radical polymerization initiator.
상기 라디칼 중합개시제는 1,1-비스(t-부틸 퍼옥시)-3,3,5-트리메틸 시클로헥산 등의 퍼옥시 케탈류; 디-t-부틸 퍼옥사이드, 2,5-디메틸-2,5-디(t-부틸 퍼옥시)헥산 등의 디알킬 퍼옥사이드류; 디벤조일 퍼옥사이드 등의 디아실 퍼옥사이드류; t-부틸 퍼옥시 이소프로필 카보네이트 등의 퍼옥시 에스테르류; 시클로헥사논 퍼옥사이드 등의 케논 퍼옥사이드류; 및 2,2’-아조비스이소부티로니트릴 등의 아조화합물 등으로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있다.The radical polymerization initiators are peroxy ketals such as 1,1-bis ( t -butyl peroxy) -3,3,5-trimethyl cyclohexane; Dialkyl peroxides such as di- t -butyl peroxide and 2,5-dimethyl-2,5-di ( t -butyl peroxy) hexane; Diacyl peroxides such as dibenzoyl peroxide; peroxy esters such as t -butyl peroxy isopropyl carbonate; Kenon peroxides, such as cyclohexanone peroxide; And azo compounds such as 2,2'-azobisisobutyronitrile and the like can be used.
상기 라디칼 중합개시제는 본 발명에 사용되는 총 단량체 100 중량부에 대하여 0.01 내지 0.1 중량부로 사용되는 것이 바람직하다.The radical polymerization initiator is preferably used in 0.01 to 0.1 parts by weight based on 100 parts by weight of the total monomers used in the present invention.
상기 c)단계에서의 연속투입은 b)단계에서 중합되는 공중합체의 총 고형분 함량이 20 내지 30 %인 시점에서 시작되는 것이 바람직하다. 그 고형분 함량 범위에서 분자량 조절제와 폴리실록산 오일의 연속투입을 시작하는 경우에 가공성이 향상된 공중합 수지를 얻을 수 있다.Continuous dosing in step c) is preferably started when the total solid content of the copolymerized in step b) is 20 to 30%. In the case where the continuous addition of the molecular weight regulator and the polysiloxane oil is started in the solid content range, a copolymerized resin having improved processability can be obtained.
상기 중합반응 전체는 120 내지 140 ℃에서 3 내지 6 시간 동안 실시하는 것이 바람직하다.The whole polymerization is preferably carried out at 120 to 140 ℃ for 3 to 6 hours.
상기 중합반응으로는 연속 또는 회분식 괴상중합, 용액중합, 또는 괴상-현탁중합 등을 이용할 수 있고, 바람직하게는 연속 괴상중합 또는 용액중합을 이용하는 것이다. 연속 괴상중합 또는 용액중합의 경우에 생산성 및 품질의 균일성이 우수하고, 수질오염의 문제가 없다.As the polymerization reaction, continuous or batch bulk polymerization, solution polymerization, or block-suspension polymerization may be used, and preferably, continuous bulk polymerization or solution polymerization is used. In the case of continuous bulk polymerization or solution polymerization, the productivity and quality uniformity are excellent, and there is no problem of water pollution.
본 발명의 투명 내열 수지 조성물은 투명성, 가공성, 내열성 및 강성이 모두 우수하여 광학용 또는 디스플레이용 소재로 사용하기에 적합하다.The transparent heat resistant resin composition of the present invention is excellent in transparency, processability, heat resistance and rigidity, and is suitable for use as an optical or display material.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업자에게 있어서 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속하는 것도 당연한 것이다.Hereinafter, preferred examples are provided to aid the understanding of the present invention, but the following examples are merely for exemplifying the present invention, and it will be apparent to those skilled in the art that various changes and modifications can be made within the scope and spirit of the present invention. It is natural that such variations and modifications fall within the scope of the appended claims.
[실시예]EXAMPLE
실시예 1Example 1
메틸 메타크릴레이트 78 중량부, 스티렌 17 중량부, 메타크릴산 5 중량부, 톨루엔 20 중량부 및 t-부틸 이소프로필 모노퍼옥시카보네이트(t-Butyl isopropyl monoperoxycarbonate, Seki Arkema사, 1시간 반감기 온도 118 ℃) 0.015 중량부를 비이커에 넣어 혼합하였다. 상기 혼합된 용액을 2 개의 교반 반응기가 직렬로 연결된 연속중합장치의 첫 번째 교반 반응기에 투입하고, 온도를 125 ℃로 제어하면서 1 시간 동안 중합하여, 총 고형분 함량 28 %인 폴리머 용액을 얻었다. 페닐계 폴리실록산오일(동양실리콘사, 1000 cst, nD = 1.501) 0.05 중량부, n-옥틸머캅탄 0.2 중량부 및 톨루엔 10 중량부를 또 다른 비이커에 넣어 혼합한 후, 상기 첫 번째 교반 반응기에 투입하여 상기 총 고형분 함량 28 %인 폴리머 용액과 혼합하였다. 그런 다음, 135 ℃로 제어된 두 번째 교반 반응기로 이송시키고, 2.5 시간 동 안 중합하여 최종 폴리머 용액을 얻었다.Methyl methacrylate 78 parts by weight, styrene 17 parts by weight, methacrylic acid 5 parts by weight, toluene 20 parts by weight and t-butyl isopropyl monoperoxycarbonate (Seki Arkema, Seki Arkema, 1 hour half-life temperature 118 C) 0.015 parts by weight were mixed in a beaker. The mixed solution was introduced into a first stirred reactor of a continuous polymerization apparatus in which two stirred reactors were connected in series, and polymerized for 1 hour while controlling the temperature to 125 ° C. to obtain a polymer solution having a total solid content of 28%. 0.05 parts by weight of phenyl polysiloxane oil (Dongyang Silicon, 1000 cst, nD = 1.501), 0.2 parts by weight of n-octyl mercaptan and 10 parts by weight of toluene were mixed in another beaker, and then charged into the first stirring reactor. It was mixed with a polymer solution having the total solids content of 28%. It was then transferred to a second stirred reactor controlled at 135 ° C. and polymerized for 2.5 hours to give the final polymer solution.
상기 최종 폴리머 용액을 미니압출기를 통하여 잔류 단량체, 용제 등의 휘발분을 제거하고, 펠렛화하여 최종적으로 투명 내열 수지 조성물을 제조하였다.The final polymer solution was removed through a mini-extruder to remove volatile components such as residual monomers and solvents, and pelletized to finally prepare a transparent heat-resistant resin composition.
실시예 2Example 2
상기 실시예 1에서 메틸 메타크릴레이트 80 중량부, 스티렌 17 중량부, 메타크릴산 3 중량부로 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.Except for using 80 parts by weight of methyl methacrylate, 17 parts by weight of styrene, 3 parts by weight of methacrylic acid in Example 1 was carried out in the same manner as in Example 1.
실시예 3Example 3
상기 실시예 1에서 메틸 메타크릴레이트 75 중량부, 스티렌 17 중량부, 메타크릴산 8 중량부로 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.Except for using 75 parts by weight of methyl methacrylate, 17 parts by weight of styrene, 8 parts by weight of methacrylic acid in Example 1 was carried out in the same manner as in Example 1.
실시예 4Example 4
상기 실시예 1에서 폴리실록산오일을 0.01 중량부로 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.Except that the polysiloxane oil in 0.01 parts by weight in Example 1 was carried out in the same manner as in Example 1.
비교예 1Comparative Example 1
상기 실시예 1에서 메틸 메타크릴레이트 82 중량부, 스티렌 18 중량부를 사 용하며, 메타크릴산을 사용하지 않은 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.82 parts by weight of methyl methacrylate and 18 parts by weight of styrene were used in Example 1, except that methacrylic acid was not used.
비교예 2Comparative Example 2
상기 실시예 1에서 폴리실록산오일을 사용하지 않은 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.Except that the polysiloxane oil was not used in Example 1 was carried out in the same manner as in Example 1.
비교예 3Comparative Example 3
상기 실시예 1에서 폴리실록산오일을 3 중량부 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하였다.Except for using 3 parts by weight of polysiloxane oil in Example 1 was carried out in the same manner as in Example 1.
상기 실시예 1 내지 4 및 비교예 1 내지 3에서 제조한 투명 내열 수지 조성물을 각각 1/8˝의 두께로 프레스 몰딩 시편으로 제작하여, 하기와 같은 방법으로 물성을 측정하였고, 그 결과를 하기 표 1에 나타내었다.The transparent heat-resistant resin compositions prepared in Examples 1 to 4 and Comparative Examples 1 to 3 were each prepared as press-molded specimens at a thickness of 1 / 8˝, and the physical properties thereof were measured by the following methods, and the results are shown in the following table. 1 is shown.
* 총 빛 투과율(total light transmittance) - Mippon Denshoku Kogyo사의 NDH-300A를 사용하여 측정하였다.Total light transmittance was measured using NDH-300A manufactured by Mippon Denshoku Kogyo.
* 유리전이온도(glass transition temperature) - Perkin Elmer사의 Pyris 6 DSC(Differential Scanning Calorimeter)를 사용하여 측정하였다.* Glass transition temperature-measured using a Pyris 6 Differential Scanning Calorimeter (DSC) from Perkin Elmer.
* 굴절률 - ASTM D-1298에 의거하여 Leika사의 아베 굴절기를 사용하여 측정하였다.* Refractive Index-Measured using an Abe refractor manufactured by Leika according to ASTM D-1298.
* 시트 절단 테스트 - 190 ℃의 롤(roll)을 이용하여 0.5 mm 두께의 시트를 제조하고 이를 절단기로 절단하여 파단면을 육안으로 관찰하고, 하기의 기준으로 평가하였다. * Sheet Cutting Test-A sheet having a thickness of 0.5 mm was prepared using a roll at 190 ° C., cut with a cutter, and the fracture surface was visually observed and evaluated according to the following criteria.
○: 파열단면 양호, △: 파열단면 보통, X: 파열단면 불량(Circle): A tearing cross section good, (triangle | delta): A tearing cross section normal, X: A tearing cross section bad
[표 1]TABLE 1
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 투명 내열 수지 조성물(실시예 1 내지 4)의 경우에 빛 투과율, 유리전이온도, 굴절율 및 시트 절단시 파단면이 모두 우수함을 확인할 수 있었다. 반면에 메타크릴산을 포함하지 않은 경우(비교예 1) 유리전이온도가 현저히 낮았고, 폴리실록산 오일을 사용하지 않은 경우(비교예 2) 시트 절단시 파단면이 불규칙했으며, 폴리실록산 오일을 과량 사용한 경우(비교예 3)에는 빛 투과율이 현저히 떨어져 투명성이 좋지 않음을 확인할 수 있었다. As shown in Table 1, in the case of the transparent heat-resistant resin composition (Examples 1 to 4) according to the present invention, it was confirmed that the light transmittance, glass transition temperature, refractive index and the fracture surface at the time of cutting the sheet are all excellent. On the other hand, when it did not contain methacrylic acid (Comparative Example 1), when the glass transition temperature was significantly low, and when polysiloxane oil was not used (Comparative Example 2), the fracture surface was irregular when cutting the sheet, and the polysiloxane oil was used excessively ( In Comparative Example 3) it was confirmed that the light transmittance was remarkably poor and the transparency was not good.
상기에서 살펴본 바와 같이, 본 발명의 투명 내열 수지 조성물은 방향족 비닐화합물 및 메틸 메타크릴레이트 단량체에 메타크릴산 단량체와 특정한 폴리실록산오일을 일정량 투입하여 중합함으로써 투명성, 내열성 및 가공성이 뛰어난 투명 내열 수지 조성물 및 그 제조방법을 제공하는 효과가 있다. As described above, the transparent heat-resistant resin composition of the present invention is polymerized by adding a certain amount of methacrylic acid monomer and a specific polysiloxane oil to the aromatic vinyl compound and methyl methacrylate monomer, and having excellent transparency, heat resistance and processability, and It is effective to provide the manufacturing method.
또한 본 발명에 따르면, 상기 투명 내열 수지 조성물을 포함하는 광학용 또는 디스플레이용 소재를 제공하는 효과가 있다. In addition, according to the present invention, there is an effect of providing an optical or display material containing the transparent heat-resistant resin composition.
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| US8455605B2 (en) | 2009-12-31 | 2013-06-04 | Cheil Industries, Inc. | Resin composition for transparent encapsulation material and electronic device formed using the same |
| US8512870B2 (en) | 2009-12-30 | 2013-08-20 | Cheil Industries, Inc. | Transparent resin for encapsulation material and electronic device including the same |
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| KR100385722B1 (en) | 1999-10-11 | 2003-05-27 | 주식회사 엘지화학 | Transparent thermoplastic resin composition having superior parting properties and method for preparing the same |
| KR100409077B1 (en) * | 2001-01-04 | 2003-12-11 | 주식회사 엘지화학 | Method for continuous preparation of rubber-modified styrene resin having superior environmental stress cracking resistance |
| JP2002212233A (en) | 2001-01-15 | 2002-07-31 | Denki Kagaku Kogyo Kk | Poly(meth)acryl/styrene resin, and sheet and food package container made thereof |
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| US8512870B2 (en) | 2009-12-30 | 2013-08-20 | Cheil Industries, Inc. | Transparent resin for encapsulation material and electronic device including the same |
| US8455605B2 (en) | 2009-12-31 | 2013-06-04 | Cheil Industries, Inc. | Resin composition for transparent encapsulation material and electronic device formed using the same |
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