WO2016089134A2 - Copolycarbonate et composition le contenant - Google Patents

Copolycarbonate et composition le contenant Download PDF

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Publication number
WO2016089134A2
WO2016089134A2 PCT/KR2015/013156 KR2015013156W WO2016089134A2 WO 2016089134 A2 WO2016089134 A2 WO 2016089134A2 KR 2015013156 W KR2015013156 W KR 2015013156W WO 2016089134 A2 WO2016089134 A2 WO 2016089134A2
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WO
WIPO (PCT)
Prior art keywords
formula
bis
copolycarbonate
repeating unit
hydroxyphenyl
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PCT/KR2015/013156
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English (en)
Korean (ko)
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WO2016089134A3 (fr
Inventor
황영영
박정준
홍무호
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020150170792A external-priority patent/KR101786568B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2017500068A priority Critical patent/JP6454774B2/ja
Priority to US15/316,727 priority patent/US9902853B2/en
Priority to EP15866220.5A priority patent/EP3228648B1/fr
Priority to PL15866220T priority patent/PL3228648T3/pl
Priority to CN201580040675.1A priority patent/CN106574044B/zh
Publication of WO2016089134A2 publication Critical patent/WO2016089134A2/fr
Publication of WO2016089134A3 publication Critical patent/WO2016089134A3/fr

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  • the present invention relates to a copolycarbonate and a composition comprising the same, to include a branched repeat unit in the copolycarbonate structure, to a technique for improving the flame resistance and chemical resistance while maintaining the impact strength and fluidity of the copolycarbonate will be.
  • Polycarbonate resin is prepared by condensation polymerization of aromatic diols such as bisphenol A and carbonate precursors such as phosgene, and has excellent impact strength, numerical stability, heat resistance and transparency, and are used for exterior materials, automotive parts, building materials, and optical parts of electric and electronic products. 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. . In particular, research into introducing a polysiloxane structure into the backbone of polycarbonate is underway, but most of the technologies are expensive to produce. It is disadvantageous in that flame resistance and chemical resistance are poor. The inventors hereby include branched repeat units as described below. The present invention was completed by confirming that the intrinsic laminar strength and fluidity of copolycarbonate can be improved while maintaining flame resistance and chemical resistance. [Content of invention]
  • the present invention is to provide a copolycarbonate with improved flame retardancy and chemical resistance while maintaining the inherent impact strength and fluidity of the copolycarbonate.
  • the present invention is to provide a composition comprising the copolycarbonate.
  • the present invention provides the following copolycarbonate:
  • At least one repeating unit of formula 1 to 3 is connected to each other by a branched repeating unit of formula 4,
  • Ri to R 4 are each independently hydrogen. Ci-! O alkyl, alkoxy. Or halogen,
  • Z is C- 10 alkylene unsubstituted or substituted with phenyl.
  • CO
  • Each R 5 is independently hydrogen; Unsubstituted or oxiranyl. D- 10 alkoxy substituted with oxiranyl. Or C 6 - 20 alkyl substituted with aryl; Halogen: alkoxy; Allyl; d-w haloalkyl; 20 is an aryl, - or C 6
  • n is an integer from 1 to 200.
  • 3 ⁇ 4 are each independently d-K) alkylene
  • Yl is each independently hydrogen. Ci-6 alkyl. Halogen, heat special. ( 6 alkoxy. Or C 6-20 aryl,
  • Each 3 ⁇ 4 is independently hydrogen: unsubstituted or oxiranyl.
  • n is an integer from 1 to 200.
  • R S to 1 are each independently hydrogen, d-K) alkyl. Halogen, CHO alkoxy: allyl; CHO haloalkyl: or C 6-20 aryl,
  • nl to n4 are each independently an integer of 1 to 4; .
  • Polycarbonate is prepared by condensation polymerization of an aromatic diol compound such as bisphenol A and a carbonate precursor such as phosgene. It has excellent impact strength, numerical stability, heat resistance and transparency, and is applied to a wide range of fields such as exterior materials for automobiles, automobile parts, building materials, and optical parts. In order to further improve the physical properties of the polycarbonate, it is possible to introduce a polysiloxane structure in the main chain of the polycarbonate, thereby improving the various physical properties. However, in spite of the above, in order to be suitable for various applications, the polycarbonate having a polysiloxane structure should be excellent in flame retardancy and chemical resistance.
  • a polysiloxane structure is introduced into the main chain of the polycarbonate, and a branched repeating unit is introduced as described below, thereby maintaining the physical properties of the copolycarbonate to the maximum and at the same time flame retardant and chemical resistance. It can be improved.
  • Recurring Unit of Formula 1 Recurring Unit of Formula 1
  • the repeating unit represented by the formula (1) is formed by reacting an aromatic di compound with a carbonate precursor.
  • Chemical Formula 1 preferably. Are each independently hydrogen, methyl, chloro, or bromo.
  • Z is a straight or branched chain c wo alkylene unsubstituted or substituted with phenyl, more preferably methylene, ethane- ⁇ , ⁇ -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 Phenyl) 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 ⁇ hydroxythoxy—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, 1,1-bis (4-hydroxyphenyl) -1 ⁇ phenylethane, bis (4-hydroxyphenyl) diphenylmethane, and 01, 0) -bis [3- (0 -hydroxyphenyl) propyl] polydimethylsiloxane can be derived from any one or more aromatic diol compounds selected from the group consisting of.
  • Said "derived from the aromatic diol compound” means. It means that the hydroxyl group of the aromatic di compound and the carbonate precursor react to form a repeating unit represented by the formula (1).
  • the repeating unit represented by Formula 1 is represented by the following Formula 1-1:
  • Examples of the carbonate precursors include dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclonuclear carbonate, diphenyl carbonate, and ditoryl carbonate. 1 selected from the group consisting of bis (chlorophenyl) carbonate, di-111-cresyl carbonate, dinaphthyl carbonate, bis (diphenyl) carbonate, phosgene, triphosgene, diphosgene, bromophosgene and bishaloformate More than one species can be used. Preferably, triphosgene or phosgene can be used.
  • 3 ⁇ 4 are each independently C 2 - 4 alkylene and is, most preferably, propane-1,3-diyl-10 alkylene, more preferably C 2.
  • ⁇ 3 ⁇ 4 is each independently hydrogen , methyl , ethyl , propyl, 3-phenylpropyl, 2-phenylpropyl, 3— (oxyranylmethoxy) propyl. Fluoro, chloro, bromo. Iodo, Meeshi. Ethoxy. Propoxy, allyl, 2, 2, 2- Trifluoroethyl ⁇ 3, 3, 3-trifluoropropyl, phenyl, or naphthyl.
  • ⁇ 3 ⁇ 4 is each independently d- ⁇ alkyl, more preferably C alkyl, more preferably alkyl, and most preferably methyl.
  • n is 10 or more, 15 or more, 20 or more, 25 or more, 30 or more, 31 or more, or 32 or more, 50 or less, 45 or less, 40 or less, 39 or less, 38 or less, or 37 or less Is an integer.
  • 3 ⁇ 4 are each independently a C 2 - to 10 alkylene, more preferably C 2 - 6 alkylene and most preferably isobutylene.
  • ⁇ is hydrogen.
  • 3 ⁇ 4 is each independently hydrogen , methyl , ethyl , propyl, 3-phenylpropyl, 2-phenylpropyl, 3- (oxyranylmethoxy) propyl, fluoro, chloro, bromo, iodo, medo Ci, ethoxy, propoxy, allyl, 2, 2, 2-trifluoroethyl, 3, 3, 3-trifluoropropyl, phenyl, or naphthyl.
  • each R 6 is independently d- 10 alkyl, more preferably d- 6 alkyl, still more preferably d- 3 alkyl, most preferably methyl.
  • the in is 40 or more, 45 or more, 50 or more, 5 or more. 56 or more, 57 or more, or 58 or more. It is an integer of 80 or less, 75 or less, 70 or less, 65 or less, 64 or less, 63 or less, or 62 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 2-1 and a siloxane compound represented by Formula 3-1.
  • .V is a C 2 - 10 alkenyl, and Al,
  • Xi. R 5 and n are as defined above,
  • X 2 , Yi, 3 ⁇ 4 and m are as defined above. It is preferable that the reactions of the reaction systems 1 and 2 are carried out under a metal catalyst. It is preferable to use Pt catalyst as the metal catalyst, Ashby catalyst, Karlstedt catalyst as Pt catalyst. Lamoreaux catalyst, Spe i er catalyst. PtCl 2 (C0D),
  • the metal catalyst is 0.001 part by weight, 0.005 part by weight, or 0.01 part by weight or more, 1 part by weight, 0.1 part by weight, or 0.05 part by weight based on 100 parts by weight of the compound represented by Formula 7 or 9. It can be used in parts or less.
  • 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 9 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 reactant.
  • 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, nuxamethyldisil, siloxane and nuxaphenyldisiloxane can be used.
  • an organocyclotetrasiloxane can be used as an example, and examples thereof include octamethylcyclotetrasiloxane, octaphenylcyclotetrasiloxane, and the like.
  • the organodisiloxane is 0.01 part by weight or more, or 2 parts by weight or more, based on 100 parts by weight of the organocyclosiloxane, and 10 parts by weight or less. Or 8 parts by weight or less.
  • the acid catalyst at least one selected from the group consisting of H 2 SO 4 , HC10 4 , AICI 3, SbC 1 5 , SnCl 4, and acidic clay may be used.
  • the acid catalyst is 0.01 parts by weight based on 100 parts by weight of the organocyclosiloxane It is more than 0.5 weight part or more, or 1 weight part or more. 10 parts by weight or less. 5 parts by weight or less, or 3 parts by weight or less can be used. Especially .
  • the weight ratio between the repeating units may be 1:99 to 99: 1. Preferably from 3:97 to 97: 3, from 5:95 to 95: 5, from 10:90 to 90:10. Or 15:85 to 85:15.
  • the weight ratio of the repeating units are siloxane compounds, such as siloxane compounds, and repetition (unit represented by Advantageously, the formula (2) to increase the ratio of the siloxane compound represented by Formula 3-1 represented by the above formula (2) eu 1, It is represented by the following formula 2-2:
  • R 5 and n are as defined above.
  • R 5 is methyl.
  • the repeating unit represented by the formula 3 is represented by Formula 3-2:
  • R 6 and m are as defined above.
  • R 6 is methyl.
  • the weight ratio of the total weight of the repeating unit represented by Formula 2 and the repeating unit represented by Formula 3 (Formula 1: (Formula 2 + Formula 3)) is 1: 0.001 to 1: 0.2, more preferably 1 : 0.01 to 1: 0.1.
  • the increase ratio of the repeating unit is based on the weight ratio of the aromatic dialkyl compound used to form the repeating unit of Formula 1 and the siloxane compound used to form the repeating unit of Formulas 2 and 3.
  • Copolycarbonate according to the present invention in addition to the above-described repeating units of the formula 1 to 3 includes a branched repeating unit, such as the formula (4). Accordingly, one or more of the above-described repeating units of Formulas 1 to 3 are connected to each other by branched repeating units of the following Formula 4 so that the main chain is branched, thereby maintaining the impact strength and fluidity of the copolycarbonate, while maintaining flame resistance and flame resistance. It can improve chemistry.
  • R 7 is C H3 alkyl, or More preferably. Ci-4 alkyl. Is methyl and most preferably ⁇
  • 3 ⁇ 4 to R U are each independently, hydrogen, C alkyl. Or halogen, more preferably hydrogen.
  • the repeating unit represented by Chemical Formula 4 is derived from an aromatic polyhydric alcohol compound represented by Chemical Formula 4-1.
  • R 7 is hydrogen, du) alkyl, or Rs to Rii and nl to n4 are as defined above.
  • the meaning of “derived from an aromatic polyhydric alcohol compound” means that the hydroxy group and the carbonate precursor of the aromatic polyhydric alcohol compound react to form a repeating unit represented by the formula (4). for example.
  • the aromatic polyhydric alcohol compound is THPE (ll, l-tris (4-hyc-oxyphenyl) ethane), polymerized with the tricarbonate, a carbonate precursor.
  • the repeating unit represented by Formula 4 is represented by the following Formula 4-2:
  • the aromatic polyhydric alcohol compound is 4.4 ', 4'',4' 1 '- Methanetetrayltetraphenol (4.4 '.4''.4''' -methanetetrayltetraphenol).
  • a carbonate precursor When polymerized with the tricarbonate, a carbonate precursor.
  • the repeating unit represented by Formula 4 is represented by the following Formula 4-3:
  • the carbonate precursor which can be used for formation of the repeating unit of Formula 4 above As described above for the carbonate precursor that can be used to form the repeating unit of Formula 1 described above.
  • the weight ratio of the repeating unit represented by Formula 1 and the repeating unit represented by Formula 4 is 1: 0.001 to 1: 0.1. It is excellent in the physical-property improvement effect of a copolycarbonate in the said range.
  • the weight ratio as defined above is based on the weight ratio of the aromatic dialkyl compound and the aromatic polyhydric alcohol compound used to form the repeating units of Formulas 1 and 4.
  • Copolycarbonate according to the present invention. It can be prepared by polymerizing the aforementioned aromatic diol compound, aromatic polyhydric alcohol compound, carbonate precursor and one or more siloxane compounds.
  • the aromatic dihydric compound, aromatic polyhydric alcohol compound, carbonate precursor and one or more siloxane compounds are as described above.
  • the weight ratio of each compound is as above-mentioned.
  • an interfacial polymerization method can be used. In this case, the reaction can be combined at normal pressure and low temperature, and the molecular weight can be easily adjusted.
  • the interfacial polymerization is preferably carried out in the presence of an acid binder and an organic solvent. Also.
  • the interfacial polymerization may include, for example, prepolymerization (1 ) 1-6-[) 01-
  • the materials used for the interfacial polymerization are not particularly limited as long as the materials 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, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine compound such as pyridine can be used.
  • the organic solvent is not particularly limited as long as it is a solvent usually used for polymerization of polycarbonate, and halogenated hydrocarbons such as methylene chloride and chlorobenzene can be used as an example.
  • the interfacial polymerization is a reaction such as a tertiary amine compound such as triethylamine, tetra-n-butylammonium bromide, 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 40 ° C, the reaction time is preferably 10 minutes to 5 hours.
  • interfacial polymerization reaction pH is It is preferable to keep it at 9 or more or 11 or more.
  • the interfacial polymerization may be performed by further including a molecular weight regulator.
  • the molecular weight modifier may be added before the start of the polymerization, during the start of the polymerization or after the start of the polymerization.
  • Mono-alkylphenol can be used as the molecular weight regulator.
  • the mono-alkylphenols are, for example, p-tert-butylphenol, P-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, nuxadecylphenol, octadecylphenol, eicosylphenol, docosylphenol and triacontyl. It is 1 or more types chosen from the group which consists of phenols, Preferably it is p-tert- butylphenol, In this case, a molecular weight control effect is large.
  • the molecular weight modifier is, for example, 0.01 part by weight, 0,1 part by weight, or 1 part by weight or more based on 100 parts by weight of the aromatic diol compound. 10 parts by weight or less, 6 parts by weight or less, or 5 parts by weight or less and the desired molecular weight can be obtained within this range.
  • the copolycarbonate may have a weight average molecular weight
  • the extended average molecular weight (g / mol) is at least 20.000, at least 21,000, at least 22,000, at least 23,000, at least 24,000, at least 25.000, at least 26,000, at least 27,000, or at least 28,000.
  • the said weight average molecular weight is 34,000 or less, 33,000 or less, or 32,000 or less.
  • the present invention comprises the aforementioned copolycarbonate and polycarbonate. It provides a polycarbonate composition.
  • the copolycarbonate may be used alone, but the physical properties of the copolycarbonate may be controlled by using a polycarbonate together as necessary.
  • the polycarbonate is distinguished from the copolycarbonate according to the present invention in that a polysiloxane structure is not introduced into the main chain of the polycarbonate.
  • the delicarbonate includes a repeating unit represented by Formula 5 below:
  • R'i to R'4 are each independently hydrogen. du) alkyl, d- 10 alkoxy. Or halogen,
  • Z ' is d- 10 alkylene unsubstituted or substituted with phenyl. 15 cycloalkylene, 0, S, SO, S0 2, CO, or - unsubstituted or Cwo alkyl substituted with C 3.
  • the polycarbonate may have a weight average molecular weight
  • the weight average molecular weight (g / mol) is at least 20.000, at least 21,000, at least 22,000, at least 23,000. 24.000 or more, 25.000 or more, 26,000 or more, 27.000 or more. Or 28.000 or more. In addition, the said weight average molecular weight is 34,000 or less. 33,000 or less, or 32,000 or less.
  • the repeating unit represented by Formula 5 is formed by reacting an aromatic diol compound and a carbonate precursor.
  • the aromatic diol compound and carbonate precursor which can be used are The same as described above in the repeating unit represented by the formula (1).
  • R ' 4 and Z' of the formula (5) respectively, The same as in Formula 1 to R 4 and Z.
  • the repeating unit represented by Formula 5 is represented by the following Formula 5-1:
  • the increase ratio of the copolycarbonate and the polycarbonate is preferably 99: 1 to 1:99, more preferably 90:10 to 50:50, most preferably 80:10 to 60: 40.
  • the present invention is the above-mentioned copolycarbonate or :
  • An article comprising a polycarbonate composition is provided.
  • the article is an injection molded article.
  • the article is for example an antioxidant.
  • Light stabilizer. Plasticizers, antistatic agents.
  • Nuclear floor may further comprise one or more selected from the group consisting of flame retardants, lubricants, impact modifiers, optical brighteners, ultraviolet absorbers, pigments and dyes.
  • the additives such as copolycarbonate and antioxidant according to the present invention are mixed using a mixer, and then the mixture is extruded into an extruder to produce pellets, and the pellets are dried, followed by an injection molding machine. It may include the step of injection into.
  • the copolycarbonate according to the present invention and the composition comprising the same, by introducing a polysiloxane structure in the main chain of the polycarbonate, and also by introducing a branched repeat unit, Maintaining maximum physical properties and improving flame retardancy and chemical resistance.
  • BPA bisphenol A
  • THPE 1, 1-tris (4-hydroxypheny 1) et hane
  • AP-30 previously prepared polyorganosiloxane
  • MB-60 polyorganosiloxane
  • a copolycarbonate resin was obtained in the same manner as in Example 1, except that 0.98 g of THPE was used.
  • Example 3 A copolycarbonate resin was obtained in the same manner as in Example 1, except that 0.98 g of THPE was used.
  • a copolycarbonate resin composition was prepared by mixing 80 parts by weight of the copolycarbonate prepared in Example 1 and 20 parts by weight of the polycarbonate prepared in Preparation Example 3. Comparative Example 1
  • a copolycarbonate resin was obtained in the same manner as in Example 1, except that 18.3 g of PTBP was used instead of 21.0 g without THPE. Comparative Example 2
  • a copolycarbonate resin was obtained in the same manner as in Example 1, except that the polyorganosiloxane of Preparation Example 1 (AP-30) and the polyorganosiloxane (MB-60) of Preparation Example 2 were not used. . Comparative Example 4
  • Polycarbonate resin prepared in Preparation Example 3 was used as Comparative Example 4.
  • the amount of the main reactants used in Examples and Comparative Examples was as shown in Table 1 below.
  • Phase Silver Hot Lapium Strength Measured at 23 ° C based on ASTM D256 (1/8 inch, Notched IzodHl).
  • MI Melt Index
  • Flame retardancy was evaluated based on UL 94V. Specifically, five flame retardant specimens having a thickness of 3.0 kPa required for application of the flame retardant test were prepared and evaluated as follows.

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  • Polyesters Or Polycarbonates (AREA)
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Abstract

La présente invention concerne un copolycarbonate et une composition le contenant et, plus spécifiquement, une technique d'amélioration de l'ininflammabilité et de la résistance chimique tout en maintenant la résistance aux chocs et l'aptitude à l'écoulement intrinsèques du copolycarbonate en ce qu'il comprend une unité de répétition ramifiée dans une structure du copolycarbonate.
PCT/KR2015/013156 2014-12-04 2015-12-03 Copolycarbonate et composition le contenant WO2016089134A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2017500068A JP6454774B2 (ja) 2014-12-04 2015-12-03 コポリカーボネートおよびこれを含む組成物
US15/316,727 US9902853B2 (en) 2014-12-04 2015-12-03 Copolycarbonate and composition comprising the same
EP15866220.5A EP3228648B1 (fr) 2014-12-04 2015-12-03 Copolycarbonate et composition le contenant
PL15866220T PL3228648T3 (pl) 2014-12-04 2015-12-03 Kopoliwęglan i zawierające go kompozycje
CN201580040675.1A CN106574044B (zh) 2014-12-04 2015-12-03 共聚碳酸酯和包含该共聚碳酸酯的组合物

Applications Claiming Priority (4)

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KR10-2014-0173005 2014-12-04
KR20140173005 2014-12-04
KR10-2015-0170792 2015-12-02
KR1020150170792A KR101786568B1 (ko) 2014-12-04 2015-12-02 코폴리카보네이트 및 이를 포함하는 조성물

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WO2016089134A2 true WO2016089134A2 (fr) 2016-06-09
WO2016089134A3 WO2016089134A3 (fr) 2016-09-29

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JP3457805B2 (ja) * 1996-06-28 2003-10-20 三菱エンジニアリングプラスチックス株式会社 ポリカーボネート系樹脂組成物
JP5684548B2 (ja) * 2010-11-30 2015-03-11 帝人株式会社 ガラス繊維強化樹脂組成物
US9115283B2 (en) * 2011-03-31 2015-08-25 Sabic Global Technologies B.V. Heat resistant clear polycarbonate-polysiloxane compounds
US20130313493A1 (en) * 2012-05-24 2013-11-28 Sabic Innovative Plastics Ip B.V. Flame retardant polycarbonate compositions, methods of manufacture thereof and articles comprising the same
JP5823944B2 (ja) * 2012-10-16 2015-11-25 帝人株式会社 ポリカーボネート−ポリジオルガノシロキサン共重合体およびその製造方法

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