WO2016036202A1 - 코폴리카보네이트 및 이를 포함하는 조성물 - Google Patents
코폴리카보네이트 및 이를 포함하는 조성물 Download PDFInfo
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- WO2016036202A1 WO2016036202A1 PCT/KR2015/009369 KR2015009369W WO2016036202A1 WO 2016036202 A1 WO2016036202 A1 WO 2016036202A1 KR 2015009369 W KR2015009369 W KR 2015009369W WO 2016036202 A1 WO2016036202 A1 WO 2016036202A1
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- WIPO (PCT)
- Prior art keywords
- formula
- bis
- copolycarbonate
- repeating unit
- hydroxyphenyl
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Oc1ccccc1 Chemical compound Oc1ccccc1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/18—Block or graft polymers
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
Definitions
- the present invention relates to a copolycarbonate and a composition comprising the same, and more particularly, to a copolycarbonate and a composition containing the same, which is economically manufactured, and has improved phase silver layer strength, low temperature impact strength and fluidity.
- Polycarbonate resins are prepared by condensation polymerization of aromatic di- like bisphenol A and carbonate precursors such as phosgene, and have excellent lamella strength, numerical stability, heat resistance and transparency, and exterior materials for automobiles, automobile parts, building materials, and optical parts. It is applied to a wide range of fields. In order to apply such polycarbonate resins in recent years, many studies have been attempted to obtain desired physical properties by copolymerizing two or more different types of aromatic dialkyl compounds to introduce units having different structures into the main chain of polycarbonate. .
- the present invention is to provide a copolycarbonate with improved phase silver layer strength, low silver impact strength and fluidity properties.
- the present invention is to provide a polycarbonate composition comprising the copolycarbonate and polycarbonate.
- the present invention also provides an article comprising the copolycarbonate or polycarbonate composition.
- Copolycarbonates having a weight average molecular weight of 1,000 to 100, 000 g / irol are provided.
- Ri to R 4 are independently hydrogen, d- 10 alkyl or halogen, Z is an unsubstituted alkylene group, a d- or 10 substituted with phenyl or C 3, respectively - 10 cycloalkylene, 0, S, SO, S0 2 Or CO,
- Ra is independently d- 10 alkylene
- 3 ⁇ 4 are each independently hydrogen or ( 13 alkyl,
- n is an integer from 1 to 40
- Each R b is independently d-) alkylene
- 3 ⁇ 4 are each independently hydrogen or d- 13 alkyl
- Copolycarbonate according to the present invention includes a polycarbonate structure formed of a repeating unit represented by the formula (1).
- the polycarbonate is excellent in overall mechanical properties, but phase impact strength, low temperature impact strength and fluidity properties are inferior, in order to improve this it is necessary to introduce a structure other than the polycarbonate structure.
- the polysiloxane formed by the repeating unit represented by the formula (2) and the repeating unit represented by the formula (3) has a structure co-condensed to polycarbonate, This significantly improves the room temperature impact strength, low temperature laminar strength and fluidity properties compared to the conventional polycarbonate.
- the repeating unit represented by Formula 2 and the repeating unit represented by Formula 3 are different from each other in the number of repeating units (n and m) of the silicon oxide in each formula.
- the repeating unit represented by Formula (2) and the repeating unit represented by the formula (3) compared to the case of including only one of the repeating unit represented by the formula (2) and the repeating unit represented by the formula (3), when it contains all the room temperature impact strength, low temperature impact strength and It was confirmed that the degree of improvement in the fluidity properties was significantly increased, which is attributable to the result of the complementary action of the properties improvement by each repeating unit.
- Repeat unit represented by Formula 1
- the repeating unit represented by Formula 1 is formed by reacting an aromatic di compound and a carbonate precursor.
- Z is straight or branched chain dw alkylene unsubstituted or substituted with phenyl, more preferably methylene, ethane-1,1-diyl, propane-2, 2-diyl, butane-2 ⁇ 2-diyl, 1-phenylethane-1,1_diyl, or diphenylmethylene.
- Z is cyclonucleic acid # 1,1-diyl, 0, S, SO, S0 2 , or CO.
- the repeating unit represented by Formula 1 is bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) ) Sulfoxide, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1,1-bis (4-hydroxyphenyl) ethane, bisphenol A, 2, 2-bis (4-hydroxy) Oxyphenyl) butane, 1,1- Bis (4-hydroxyphenyl) cyclonucleic acid, 2, 2-bis (4-hydroxy—3, 5-dibromophenyl) propane, 2, 2-bis (4-hydroxy-3, 5-dichlorophenyl Propane, 2, 2-bis (4-hydroxy-3-bromophenyl) propane, 2, 2-bis (4-hydroxy-3-chlorophenyl) propane, 2, 2-bis (4-hydroxy 3-Methylphenyl) propane, 2, 2-bis (4-hydroxy-3, 5-dimethylphenyl) propane, 2, 2-
- Examples of the carbonate precursors include dimethyl carbonate, diethyl carbonate dibutyl carbonate, dicyclonuclear carbonate, diphenyl carbonate, ditoryl carbonate, bis (chlorophenyl) carbonate, di-m-cresyl carbonate, dinaphthyl carbonate, and bis.
- At least one selected from the group consisting of (diphenyl) carbonate, phosgene, triphosgene, diphosgene, bromophosgene, and bishaloformate can be used.
- triphosgene or phosgene can be used.
- the repeating unit represented by the formula (2) and the repeating unit represented by the formula (3) are formed by reacting a siloxane compound and a carbonate precursor, respectively.
- Ra is preferably each independently C 2 - 4 alkylene and is, most preferably, propane-1,3-diyl eu-10 alkylene, more preferably C 2.
- 3 ⁇ 4 is preferably each independently d- 6 alkyl, more preferably each independently d- 3 alkyl, most preferably methyl.
- Rb are preferably each independently C 2 - 4 alkylene and is, most preferably, propane-1,3-diyl-10 alkylene, more preferably C 2.
- 3 ⁇ 4 is preferably each independently d-6 alkyl, more preferably each independently d- 3 alkyl, most preferably methyl.
- Ra and Rb are the same as each other.
- Rs and 3 ⁇ 4 are identical to each other.
- Chemical Formula 2 is represented by the following Chemical Formula 2-1:
- Chemical Formula 3 is represented by the following Chemical Formula 3-1: [Formula 3-1]
- n is 10 or more, 15 or more, 20 or more, or 25 or more, and an integer of 35 or less.
- m is 45 or more, 50 or more, or 55 or more, 100 or less, 95 or less, 90 or less, 85 or less, 80 or less, 75 or less, 70 or less, or an integer of 65 or less.
- the repeating unit represented by Formula 2 and the repeating unit represented by Formula 3 are each derived from a siloxane compound represented by Formula 2-2 and a siloxane compound represented by Formula 3-2.
- Ra, R 5 and n are as defined above,
- Rb, R 6 and m are as defined above.
- the term “derived from the siloxane compound” means that the hydroxyl group and the carbonate precursor of each of the siloxane compounds react with each other to form a repeating unit represented by Formula 2 and a repeating unit represented by Formula 3 do.
- R 5 and definition of n are as previously defined, R a 'is C 2 - 10 alkenyl, and Al, [banung formula 2]
- R 6 and m is as defined above and is Rb 'C 2 -io alkenyl.
- the reactions of the reactions 1 and 2 are preferably carried out under a metal catalyst.
- Pt catalyst is preferably used.
- As the Pt catalyst an ashby catalyst, a Karlstedt catalyst, a moreaux catalyst, a spier catalyst, a PtCl 2 (C0D),
- At least one selected from the group consisting of PtCl 2 (benzonitrile) 2 , and 3 ⁇ 4PtBr 6 can be used.
- the metal catalyst is 0.001 parts by weight, 0.005 parts by weight, or 0.01 parts by weight or more, 1 part by weight, 0.1 parts by weight, or 0.05 parts by weight or less based on 100 parts by weight of the compound represented by Formula 7 or 8 above.
- the reaction temperature is preferably 80 to 100 ° C.
- the reaction time is preferably 1 hour to 5 hours.
- the compound represented by Formula 7 or 8 may be prepared by reacting organodisiloxane and organocyclosiloxane under an acid catalyst, and n and m may be controlled by adjusting the content of the reaction compound.
- the reaction temperature is preferably 50 to 70 ° C.
- the reaction time is preferably 1 hour to 6 hours.
- the organodisiloxane one or more selected from the group consisting of tetramethyldisiloxane, tetraphenyldisiloxane, nuxamethyldisiloxane and nuxaphenyldisiloxane can be used.
- an organocyclotetrasiloxane may be used as an example, and examples thereof include octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, and the like.
- the organodisiloxane may be used in an amount of 0.01 parts by weight or more, or 2 parts by weight or more, 10 parts by weight or less, or 8 parts by weight or less, based on 100 parts by weight of the organocyclosiloxane.
- the acid catalyst at least one selected from the group consisting of 3 ⁇ 4SO 4 , HC10 4 , A1C1 3) SbCl 5 , SnCl 4, and acidic clay may be used.
- the acid catalyst is 0.1 part by weight or more, 0.5 parts by weight or more, or 1 part by weight or more, 10 parts by weight or less, 5 parts by weight or less, or 3 parts by weight or less based on 100 parts by weight of organocyclosiloxane. Can be used.
- the weight ratio of the repeating unit and the repeating unit represented by Formula 3 is 99: 1 to 1:99, more preferably 80:20 to 20:80.
- the weight ratio of the repeating unit corresponds to the weight ratio of the siloxane compound, for example, the siloxane compound represented by Formula 2-2 and the siloxane compound represented by Formula 3-2.
- the copolycarbonate according to the present invention includes a repeating unit represented by Chemical Formulas 1 to 3, preferably a random copolymer. Also preferably, the copolycarbonate according to the present invention has a weight average molecular weight of 15,000 to 35,000 g / ⁇ . More preferably, the weight average molecular weight is at least 20,000 g / mol, at least 21,000 g / mol, at least 22,000 g / mol, at least 23,000 g / mol, at least 24,000 g / mol, at least 25,000 g / mol, at 26,000 g / mol Or more, 27,000 g / mol or more, or 28,000 g / mol or more. Further, the weight average molecular weight is 34,000 g / mol or less, 33,000 g / mol or less, or 32,000 g / mol or less. In addition, the weight of the repeating unit represented by Formula 1 and the formula
- the weight ratio of the total weight of the repeating unit represented by 2 and the repeating unit represented by Formula 3 is preferably 1: 0.04-0.07.
- Copolycarbonate according to the present invention is prepared by a manufacturing method comprising the step of polymerizing a composition comprising an aromatic diol compound, a compound represented by the formula (2-2), a compound represented by the formula (3-2) and a carbonate precursor described above can do.
- the total amount of the compound represented by Formula 2-2 and the compound represented by Formula 3-2 in the composition is 0.1 wt% or more, 0.5 wt% or more, or 1 wt% or more with respect to 100 wt% of the composition.
- the aromatic di compound, 40 wt% or more, 50 wt% or more, or 55 wt% or more, 80 wt% or less, 70 wt% or less, or 65 wt% or less with respect to 100 wt% of the composition. have.
- the carbonate precursor, 10 to 100% by weight of the composition At least 20% by weight, at least 20% by weight, or at least 30% by weight, at most 60% by weight, at most 50% by weight, or at most 40% by weight.
- the polymerization method for example, an interfacial polymerization method may be used.
- the polymerization reaction is possible at atmospheric pressure and low temperature, and the molecular weight is easily controlled.
- the interfacial polymerization is preferably carried out in the presence of an acid binder and an organic solvent.
- the interfacial polymerization may include a step of introducing a coupling agent after prepolymerization (pre-polymer i zat ion), and then polymerizing again, in which case, a high molecular weight copolycarbonate may be obtained.
- the materials used for the interfacial polymerization are not particularly limited as long as they are materials that can be used for the polymerization of polycarbonate, and the amount of the materials used may be adjusted as necessary.
- the acid binder for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, or pyridine and the amine compound may be used.
- the organic solvent is not particularly limited as long as it is a solvent usually used for polymerization of polycarbonate. For example, halogenated hydrocarbons such as methylene chloride and chlorobenzene may be used.
- the interfacial polymerization is a reaction such as triethylamine, tetra-n-butylammonium bromide, tertiary amine compound such as tetra-n-butylphosphonium bromide, quaternary ammonium compound, quaternary phosphonium compound, etc. Accelerators may additionally be used.
- the reaction temperature of the interfacial polymerization is preferably 0 to 4 (rc, and the reaction time is preferably 10 minutes to 5 hours.
- the pH is preferably maintained at 9 or more or 11 or more.
- the interfacial polymerization may be performed by further including a molecular weight regulator.
- the molecular weight regulator may be added before the start of polymerization, during the start of polymerization, or after the start of polymerization.
- Mono-alkylphenols may be used as the molecular weight modifier.
- the mono-alkylphenols include, for example, p-tert-butylphenol, P-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, nucledecylphenol, and octadecyl. It is at least one selected from the group consisting of phenol, eicosylphenol, docosylphenol and triacontylphenol, preferably p-tert-butylphenol, in which case the molecular weight control effect is large.
- the molecular weight modifier may be, for example, 0.01 parts by weight or more, 0, 1 parts by weight or more, or 1 part by weight or more, 10 parts by weight or less, 6 parts by weight or less, or 5 parts by weight or less based on 100 parts by weight of aromatic diol compound.
- the desired molecular weight can be obtained within this range.
- the present invention also provides a polycarbonate composition, comprising the copolycarbonate and polycarbonate.
- a polycarbonate composition comprising the copolycarbonate and polycarbonate.
- the copolycarbonate may be used alone, the physical properties of the copolycarbonate can be controlled by using a polycarbonate together if necessary.
- the polycarbonate includes a repeating unit represented by Formula 4 below:
- R'i to R'4 are each independently hydrogen, d- 10 alkyl or halogen, Z 'is unsubstituted or substituted with phenyl ( 10 alkylene, Cs-io cycloalkylene, 0, S, SO, S0 2 or CO.
- the repeating unit represented by Chemical Formula 4 is formed by reacting an aromatic diol compound and a carbonate precursor, and the aromatic diol compound and carbonate precursor which can be used are described above in the repeating unit represented by Chemical Formula 1.
- R 4 and Z 'of Formula 4 are the same as Ri to 4 and 2 of Formula 1, respectively, and preferably, the repeating unit represented by Formula 4 is , Is represented by the following formula (4-1).
- the increase ratio of copolycarbonate and polycarbonate is preferably 99: 1 to 1:99, more preferably 90:10 to 50:50, and most preferably 80:20 to 60: 40.
- the present invention also provides an article comprising the copolycarbonate or the polycarbonate composition.
- the article is an injection molded article.
- the article may be, for example, an antioxidant, a heat stabilizer, a light stabilizer, a plasticizer, an antistatic agent, a nucleating agent, a flame retardant, a lubricant, an impact enhancer, a fluorescent brightener, an ultraviolet absorber, a pigment and a dye. It may further comprise one or more selected from the group consisting of.
- the mixture is extruded by an extruder to produce a pellet, and the pellet is dried It may include the step of injection into an injection molding machine.
- the copolycarbonate in which a specific siloxane compound is introduced into the polycarbonate main chain according to the present invention has an effect of improving phase silver impact strength, low temperature impact strength and fluidity properties.
- Example 3 Prepared in the same manner as in Example 1, except that 55.2 g of polyorganosiloxane (20 wt of polyorganosiloxane (AP-30) of Preparation Example 1 and 80% of polyorganosiloxane (AP-60) of Preparation Example 2) Mixture) to prepare coplicarbonate and specimens thereof, respectively.
- polyorganosiloxane (20 wt of polyorganosiloxane (AP-30) of Preparation Example 1 and 80% of polyorganosiloxane (AP-60) of Preparation Example 2 Mixture
- MI Flowability
- Phase silver layer strength and low temperature layer strength (J / m): measured at 23 ° C and -30 ° C according to ASTM D256 (l / 8 inch, Notched Izod), respectively.
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Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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PL15838004T PL3045487T3 (pl) | 2014-09-05 | 2015-09-04 | Kompozycja obejmująca kopoliwęglan |
CN201580002901.7A CN105980445B (zh) | 2014-09-05 | 2015-09-04 | 共聚碳酸酯以及含有该共聚碳酸酯的组合物 |
US14/914,153 US9732186B2 (en) | 2014-09-05 | 2015-09-04 | Copolycarbonate and composition comprising the same |
EP15838004.8A EP3045487B1 (en) | 2014-09-05 | 2015-09-04 | Composition comprising a copolycarbonate |
JP2016541578A JP6615098B2 (ja) | 2014-09-05 | 2015-09-04 | コポリカーボネートおよびこれを含む組成物 |
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KR20140118991 | 2014-09-05 | ||
KR10-2014-0118991 | 2014-09-05 | ||
KR10-2015-0109123 | 2015-07-31 | ||
KR20150109123 | 2015-07-31 | ||
KR10-2015-0125111 | 2015-09-03 | ||
KR1020150125111A KR101687683B1 (ko) | 2014-09-05 | 2015-09-03 | 코폴리카보네이트 및 이를 포함하는 조성물 |
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Citations (5)
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KR20120050968A (ko) * | 2009-07-29 | 2012-05-21 | 테이진 카세이 가부시키가이샤 | 폴리카보네이트-폴리디오르가노실록산 공중합체 |
KR20130047332A (ko) * | 2011-10-31 | 2013-05-08 | 주식회사 삼양사 | 저온 내충격성이 향상된 폴리카보네이트 수지 조성물 및 그 제조방법 |
KR20130047612A (ko) * | 2011-10-31 | 2013-05-08 | 주식회사 삼양사 | 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법 |
KR20130090358A (ko) * | 2012-02-03 | 2013-08-13 | 주식회사 엘지화학 | 신규한 폴리오르가노실록산, 이를 포함하는 폴리카보네이트 수지 조성물 및 개질 폴리카보네이트 수지 |
WO2014058033A1 (ja) * | 2012-10-12 | 2014-04-17 | 出光興産株式会社 | ポリカーボネート-ポリオルガノシロキサン共重合体の連続的な製造方法 |
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2015
- 2015-09-04 WO PCT/KR2015/009369 patent/WO2016036202A1/ko active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20120050968A (ko) * | 2009-07-29 | 2012-05-21 | 테이진 카세이 가부시키가이샤 | 폴리카보네이트-폴리디오르가노실록산 공중합체 |
KR20130047332A (ko) * | 2011-10-31 | 2013-05-08 | 주식회사 삼양사 | 저온 내충격성이 향상된 폴리카보네이트 수지 조성물 및 그 제조방법 |
KR20130047612A (ko) * | 2011-10-31 | 2013-05-08 | 주식회사 삼양사 | 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법 |
KR20130090358A (ko) * | 2012-02-03 | 2013-08-13 | 주식회사 엘지화학 | 신규한 폴리오르가노실록산, 이를 포함하는 폴리카보네이트 수지 조성물 및 개질 폴리카보네이트 수지 |
WO2014058033A1 (ja) * | 2012-10-12 | 2014-04-17 | 出光興産株式会社 | ポリカーボネート-ポリオルガノシロキサン共重合体の連続的な製造方法 |
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