WO2015002427A1 - 폴리오르가노실록산 화합물, 제조방법 및 이를 포함하는 코폴리카보네이트 수지 - Google Patents

폴리오르가노실록산 화합물, 제조방법 및 이를 포함하는 코폴리카보네이트 수지 Download PDF

Info

Publication number
WO2015002427A1
WO2015002427A1 PCT/KR2014/005836 KR2014005836W WO2015002427A1 WO 2015002427 A1 WO2015002427 A1 WO 2015002427A1 KR 2014005836 W KR2014005836 W KR 2014005836W WO 2015002427 A1 WO2015002427 A1 WO 2015002427A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
bis
formula
group
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2014/005836
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
반형민
홍무호
황영영
김민정
박정준
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020140080439A external-priority patent/KR101566837B1/ko
Priority claimed from KR1020140080436A external-priority patent/KR101563269B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to EP14819695.9A priority Critical patent/EP3018165B1/en
Priority to CN201480003441.5A priority patent/CN104837895B/zh
Priority to PL14819695T priority patent/PL3018165T3/pl
Priority to JP2016523659A priority patent/JP6150945B2/ja
Publication of WO2015002427A1 publication Critical patent/WO2015002427A1/ko
Priority to US14/635,668 priority patent/US9267034B2/en
Priority to US14/823,756 priority patent/US9452969B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • 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
    • C08G64/186—Block or graft polymers containing polysiloxane sequences
    • 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
    • C08G64/307—General preparatory processes using carbonates and phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
    • C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • 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
    • 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
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • 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

Definitions

  • the present invention relates to a polyorganosiloxane compound, a preparation method, and a copolycarbonate resin including the same, and more particularly, can be applied to various uses, and in particular, can be used as an impact modifier, modifier or comonomer of a copolycarbonate resin. It relates to a polyorganosiloxane compound, a method for producing the same, and a copolycarbonate resin having excellent transparency to molecular weight while improving mechanical properties including low temperature impact strength.
  • Polyorganosiloxane is a kind of silicone and refers to a polymer mainly composed of siloxane bonds substituted with organic groups.
  • polyorganosiloxane is prepared by condensation polymerization of an aromatic diol such as bisphenol A and a carbonate precursor such as phosgene. It is a colorless, odorless, slow oxidation and stable at room temperature. It is a hypoallergenic insulator. It is used in electric, electronics, automobile, machinery, medical, cosmetics, caring agent, adhesives, gaskets, molding aids, etc.
  • 2002-0016922 discloses polyorganosiloxanes endblocked with trimethylsilyl useful as hydrogel contact lens materials.
  • copolycarbonate resins have recently been attempted to obtain desired physical properties by copolymerizing two or more kinds of aromatic diols having different structures to introduce a different structure into the main chain of the polycarbonate. .
  • the present invention is applicable to a variety of applications, in particular, including polyorganosiloxane compound and co-carbonate used as an impact modifier, modifier or comonomer, while maintaining the transparency It is an object to provide a copolycarbonate resin having improved low temperature impact properties.
  • R 1 , R 2 , R 3 , R ' 1 , R' 2 , R ' 3 is independently hydrogen, an alkyl group having 1 to 3 carbon atoms or an aryl group
  • R 4 is and R' is An alkyl group having 1 to 3 carbon atoms, an aryl group, or , R 5 , R ' 5 and R 7 are independently one of -OH and the other are hydrogen
  • R 6 is hydrogen or an alkoxy group having 1 to 4 carbon atoms
  • R 8 is a linear or branched alkylene group having 2 to 8 carbon atoms
  • n and m are integers 0 ⁇ n + m ⁇ 99
  • the present invention uses alkenyl alcohol and hydroxybenzoic acid having 2 to 8 carbon atoms as a starting material,
  • H-PDMS a compound in which both terminal groups are hydrogen as a polyorganosiloxane.
  • R 1 , R 2 , R 3 , R ' 1 , R' 2 , R ' 3 is independently hydrogen, an alkyl group having 1 to 3 carbon atoms or an aryl group
  • R 4 is R ' 4 is an alkyl group having 1 to 3 carbon atoms, an aryl group or
  • R 5 , R ' 5 , R 7 are independently one of -OH and the rest are each hydrogen
  • R 6 is hydrogen or an alkoxy group having 1 to 4 carbon atoms
  • R 8 is a linear or branched carbon atoms of 2 to 8 It is an alkylene group
  • n and m are integers 0 ⁇ n + m ⁇ 99
  • the present invention uses alkenyl alcohol and hydroxybenzoic acid having 2 to 8 carbon atoms as a starting material,
  • Preparing the polyorganosiloxane compound comprising the step of preparing the polyorganosiloxane compound represented by Chemical Formula 1 by adding the hydroxybenzoic acid to the OH-PDMS and performing esterification under an acid catalyst.
  • the present invention provides a polymerized copolycarbonate resin including an aromatic diol compound, a carbonate precursor, and a polyorganosiloxane compound represented by Chemical Formula 1.
  • a polyorganosiloxane compound which can be applied to various applications, in particular, can be used as an impact modifier, modifier or comonomer of a copolycarbonate resin and a low temperature impact strength while maintaining the transparency It is effective to provide a copolycarbonate resin containing improved mechanical properties.
  • Example 1 is a 1 H NMR spectrum of the polyorganosiloxane compound prepared in Example, (a) corresponds to Example 1, (b) corresponds to Example 2.
  • Example 2 is a 1 H NMR spectrum of a polydimethylsiloxane-polycarbonate modified with a polyorganosiloxane compound prepared in Example, where (a) is the use of Example 1, and (b) is the use of Example 2. This is an example.
  • the polyorganosiloxane compound of the present invention is represented by the following Chemical Formula 1
  • R 1 , R 2 , R 3 , R ' 1 , R' 2 , R ' 3 is independently hydrogen, an alkyl group having 1 to 3 carbon atoms or an aryl group
  • R 4 is R ' 4 is an alkyl group having 1 to 3 carbon atoms
  • an aryl group or R 5 , R ' 5 , and R 7 are independently one of which is -OH and the other are each hydrogen
  • R 6 is hydrogen or an alkoxy group having 1 to 4 carbon atoms
  • R 8 is linear having 2 to 8 carbon atoms or It is a branched alkylene group
  • n and m are compounds represented by 0 ⁇ n + m ⁇ 99 as an integer.
  • the polyorganosiloxane compound may be a monomer used in at least one selected from the group consisting of comonomers, modifiers and impact modifiers.
  • the polyorganosiloxane compound may be, for example, a monomer used to prepare a copolycarbonate resin.
  • the R 1 , R 2 , R 3 , R ' 1 , R' 2 , R ' 3 may each be, for example, CH 3 -or C 6 H 5- .
  • R 6 may be, for example, hydrogen.
  • R 5 and R ′ 5 may be hydrogen, and R 7 may be —OH.
  • the chain is longer, but the produced final water impact strength and flame retardancy is improved, the number of carbon atoms and diminish the 8 exceeds the glass transition temperature, having 2 to 8 alkylene, or alkyl renil of 3 to 5 carbon atoms in the And in particular branched alkylene having 3 to 5 carbon atoms.
  • N is an integer of 10 to 90, or an integer of 25 to 75
  • m is an integer of 10 to 90, or an integer of 25 to 75
  • the n + m is 1 to 99, or 50 to 99, this range It is effective in mechanical properties and transparency within.
  • the compound represented by Formula 1 may be represented by the following Formula 2
  • the compound represented by Formula 1 may be represented by the following Formula 3
  • the starting material may be prepared using orthohydroxybenzoic acid or parahydroxybenzoic acid and alkenyl alcohol having 2 to 8 carbon atoms, and specific examples thereof may include parahydroxybenzoic acid and alkenyl alcohol having 2 to 8 carbon atoms.
  • the method for preparing the polyorganosiloxane compound represented by Chemical Formula 2 may be represented by the following Scheme 1.
  • Catalyst is not particularly limited in the case of an acid catalyst that can be used for polyorganosiloxane synthesis, for example at least one selected from the group consisting of H2SO4, HClO4, AlCl3, SbCl5, SnCl4, and acidic clay Can be.
  • the acid catalyst may be used in an amount of 0.1 to 10 parts by weight, 0.5 to 5 parts by weight, or 1 to 3 parts by weight based on 100 parts by weight of H-PDMS.
  • the acid catalyzed reaction may be carried out, for example, for 1 to 6 hours at 50 to 70 °C.
  • the acid catalyzed reaction can be carried out with dioxane, tetrahydrofuran, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether, dichloromethane, trichloromethane, tetrachloromethane, 1,2-dichloroethane and trichloro, if necessary.
  • Chlorinated hydrocarbons such as ethylene; Aprotic solvents such as pentane, n-hexane, hexane isomer mixtures, hydrocarbons such as heptane and octane, solvent naphtha, petroleum ether, benzene, toluene and xylene range from 1 to 10 times based on polyorganosiloxane ( By weight).
  • the hydrosilylation reaction may be carried out under a metal catalyst, for example.
  • the metal catalyst is not particularly limited as long as it is a metal catalyst that can be used for the terminal modification reaction of the polyorganosiloxane, and may be, for example, a Pt catalyst.
  • the Pt catalyst is not particularly limited as long as it is a Pt catalyst that can be used in polyorganosiloxane synthesis, for example, an Ashby catalyst, a Karlstedt catalyst, a Lamoreaux catalyst, and a Spire catalyst. , PtCl 2 (COD), PtCl 2 (benzonitrile) 2, and H 2 PtBr 6.
  • the metal catalyst may be used in an amount of 0.001 to 1 part by weight, 0.005 to 0.1 part by weight, or 0.01 to 0.05 part by weight based on 100 parts by weight of polyorganosiloxane such as H-PDMS.
  • the hydrosilylation reaction can be carried out with dioxane, tetrahydrofuran, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether, dichloromethane, trichloromethane, tetrachloromethane, 1,2-dichloroethane and trichloro as needed.
  • Chlorinated hydrocarbons such as roethylene; Pentane, n-hexane, hexane isomer mixtures, Hydrocarbons such as heptane, octane, solvent naphtha, petroleum ether, aprotic solvents such as benzene, toluene and xylene are used in a 1 to 10-fold range (by weight) based on polyorganosiloxanes such as H-PDMS Can be done.
  • the hydrosilylation reaction may be performed at 60 to 100 ° C. for 1 to 5 hours.
  • H-PDMS refers to capping polydimethylsiloxane (PDMS) with hydrogen (-H) as H-PDMS-H unless otherwise specified, and the term “OH-PDMS”.
  • PDMS polydimethylsiloxane
  • OH-PDMS OH-PDMS
  • a step of performing a hydrosilylation reaction by reacting an alkenyl alcohol having 2 to 8 carbon atoms with H-PDMS;
  • Hydroxybenzoic acid may be added to the hydrosilylation reaction and esterified to obtain a polyorganosiloxane compound represented by Chemical Formula 1.
  • the acid (Acid) of Scheme 3 is not particularly limited in the case of an acid catalyst that can be used in the polyorganosiloxane synthesis, the reaction conditions are also sufficient to carry out the reaction under conventional esterification conditions.
  • the hydrosilylation reaction may be carried out under a metal catalyst, for example.
  • the metal catalyst is not particularly limited as long as it is a metal catalyst that can be used for the terminal modification reaction of the polyorganosiloxane, and may be, for example, a Pt catalyst.
  • the Pt catalyst is not particularly limited as long as it is a Pt catalyst that can be used in polyorganosiloxane synthesis, for example, an Ashby catalyst, a Karlstedt catalyst, a Lamoreaux catalyst, and a Spire catalyst. , PtCl 2 (COD), PtCl 2 (benzonitrile) 2, and H 2 PtBr 6.
  • the metal catalyst may be used in an amount of 0.001 to 1 part by weight, 0.005 to 0.1 part by weight, or 0.01 to 0.05 part by weight based on 100 parts by weight of polyorganosiloxane such as H-PDMS.
  • the hydrosilylation reaction can be carried out with dioxane, tetrahydrofuran, diethyl ether, diisopropyl ether, diethylene glycol dimethyl ether, dichloromethane, trichloromethane, tetrachloromethane, 1,2-dichloroethane and trichloro as needed.
  • Chlorinated hydrocarbons such as roethylene; Aprotic solvents such as pentane, n-hexane, hexane isomer mixtures, hydrocarbons such as heptane and octane, solvent naphtha, petroleum ether, benzene, toluene and xylene are based on polyorganosiloxanes such as H-PDMS. It can be carried out by using in the range of ⁇ 10 times (by weight).
  • the hydrosilylation reaction may be performed at 60 to 100 ° C. for 1 to 5 hours.
  • the copolycarbonate resin of the present invention is characterized by including an aromatic diol compound, a carbonate precursor, and a polyorganosiloxane compound represented by the following formula (1).
  • R 1 , R 2 , R 3 , R ' 1 , R' 2 , R ' 3 is independently hydrogen, an alkyl group having 1 to 3 carbon atoms or an aryl group
  • R 4 is R ' 4 is an alkyl group having 1 to 3 carbon atoms
  • an aryl group or R 5 are each independently one of -OH and the others are hydrogen
  • R 6 is hydrogen or an alkoxy group having 1 to 4 carbon atoms
  • R 8 is a linear having 2 to 8 carbon atoms or Branched alkylene group, where n and m are integers, 0 ⁇ n + m ⁇ 99)
  • the copolycarbonate resin is, for example, 25 to 85% by weight of the aromatic diol compound, based on the total amount of 100% by weight of the aromatic diol compound, the carbonate precursor, and the polyorganosiloxane compound represented by Formula 1, represented by Formula 1 1 to 60% by weight of the polyorganosiloxane compound, which is polymerized with 10 to 70% by weight of the carbonate precursor, while maintaining the low-temperature impact strength within this range, there is an excellent transparency to the molecular weight.
  • the polycarbonate is represented by the aromatic diol compound 30 to 70% by weight, based on 100% by weight of the aromatic diol compound, the carbonate precursor, and the polyorganosiloxane compound represented by Formula 1 5 to 50% by weight of the polyorganosiloxane compound, and 20 to 60% by weight of the carbonate precursor may be polymerized.
  • aromatic diol compound examples include bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfoxide and bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1,1-bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A) , 2,2-bis (4-hydroxyphenyl) butane, 1,1-bis (4-hydroxyphenyl) cyclohexane (bisphenol Z), 2,2-bis (4-hydroxy-3,5-di Bromophenyl) 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,
  • the carbonate precursor is, for example, the formula
  • X 1 and X 2 are independently halogen, haloalkyl group, halocycloalkyl group, haloaryl group, alkoxy group or haloalkoxy group), and within this range to impart the essential properties of the polycarbonate resin It works.
  • the polycarbonate may be polymerized by further including, for example, a molecular weight regulator.
  • the molecular weight modifier is for example mono-alkylphenol.
  • the mono-alkylphenols are, for example, p-tert-butylphenol, p-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, ecosylphenol, docosylphenol and triacontyl. It is 1 or more types chosen from the group which consists of phenols, Preferably it is para-tert- butylphenol, In this case, a molecular weight control effect is large.
  • the molecular weight modifier is, for example, 0.01 to 10 parts by weight, 0.1 to 6 parts by weight, or 1 to 5 parts by weight based on 100 parts by weight of the total amount of the aromatic diol compound, the carbonate precursor, and the polyorganosiloxane compound represented by Formula 1 above. It may be included in the negative portion, and the target molecular weight can be obtained within this range.
  • the polycarbonate has a glass transition temperature of 145 to 160 ° C, or 145 to 155 ° C, and a weight average molecular weight of 10,000 to 80,000 g / mol, 15,000 to 80,000 g / mol, 20,000 to 60,000 g / mol, and 22,000 to 55,000 g / mol, while maintaining the low-temperature impact strength within this range, there is an excellent transparency compared to the molecular weight.
  • the method for preparing the copolycarbonate resin of the present invention may be, for example, an interfacial polymerization method, in which case the polymerization reaction is possible at atmospheric pressure and low temperature, and the molecular weight is easily controlled.
  • the interfacial polymerization method may be, for example, a method of reacting an aromatic diol monomer, a carbonate precursor, and a molecular weight modifier in the presence of an acid binder and an organic solvent.
  • the interfacial polymerization method may include a step of pre-polymerization, a coupling agent, and then polymerization again.
  • a high molecular weight copolycarbonate resin may be obtained.
  • the other materials used for the interfacial polymerization are not particularly limited as long as they are materials that can be used for the polymerization of copolycarbonate, and the amount of the materials used may be adjusted as necessary.
  • the acid binder is, for example, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine compound such as pyridine.
  • the organic solvent is not particularly limited in the case of a solvent usually used for polymerization of copolycarbonate, and may be, for example, a halogenated hydrocarbon such as methylene chloride and chlorobenzene.
  • the interfacial polymerization is, for example, reactions such as tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, tetra-n-butylphosphonium bromide, quaternary ammonium compounds, and quaternary phosphonium compounds to promote reaction. Accelerators may be used further.
  • tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, tetra-n-butylphosphonium bromide, quaternary ammonium compounds, and quaternary phosphonium compounds to promote reaction. Accelerators may be used further.
  • the reaction temperature of the interfacial polymerization is, for example, 0 to 40 °C
  • the reaction time is for example 10 minutes to 5 hours
  • the pH of the reaction may be preferably maintained at 9 or more or 11 or more, for example.
  • 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.
  • the molded article of the present invention is characterized by comprising the copolycarbonate resin.
  • the molded article may be, for example, an injection molded article.
  • the molded article may further include at least one selected from the group consisting of antioxidants, plasticizers, antistatic agents, nucleating agents, flame retardants, lubricants, impact modifiers, optical brighteners, ultraviolet absorbers, pigments and dyes.
  • the copolycarbonate resin of the present invention and an additive such as an antioxidant are mixed well by using a mixer, and then the mixture is extruded by an extruder to produce pellets, and the pellet is dried well. It may include the step of injection into the next injection molding machine.
  • the terminal modified polyorganosiloxane thus obtained ie, the polyorganosiloxane compound represented by 4 in Scheme 2, was a pale yellow oil, the repeating unit (p) was 55, and no further purification was necessary.
  • the structure of the polyorganosiloxane compound represented by 5 in Scheme 2 was confirmed by 1 H NMR (see FIG. 2 (a)).
  • Copolycarbonate resins and injection specimens containing the siloxane compounds of Examples 1 and 2 and Comparative Examples 1 and 2 were prepared as follows.
  • the obtained copolycarbonate resin was summarized in Table 1 by measuring the molecular weight by GPC using PC standard (Standard).
  • Haze 1.5 mm thick, 40 mm diameter disc specimens were fabricated and measured according to ASTM D1003.
  • MI Flowability
  • Tg Glass transition temperature
  • Example 1 33,500 66.3 60.2 1.3 12 148.4
  • Example 2 34,500 67.2 62.7 1.1 10 147.8
  • Comparative Example 1 31,500 56.4 17.1 0.6 30 145.3
  • Comparative Example 2 33,600 65.1 58.6 2.1 8 143.8
  • the copolycarbonate resin (Examples 1 to 2) of the present invention is a copolycarbonate resin (Comparative Example 1) and a conventional eugenol containing a conventional allylphenol-modified siloxane compound Compared with the copolycarbonate resin (Comparative Example 2) containing the compound it was confirmed that the physical properties, especially low-temperature impact strength while maintaining transparency.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Silicon Polymers (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/KR2014/005836 2013-07-01 2014-07-01 폴리오르가노실록산 화합물, 제조방법 및 이를 포함하는 코폴리카보네이트 수지 Ceased WO2015002427A1 (ko)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP14819695.9A EP3018165B1 (en) 2013-07-01 2014-07-01 Polyorganosiloxane compound, method for preparing same, and copolycarbonate resin comprising same
CN201480003441.5A CN104837895B (zh) 2013-07-01 2014-07-01 聚硅氧烷化合物及其制备方法以及包含它的共聚碳酸酯树脂
PL14819695T PL3018165T3 (pl) 2013-07-01 2014-07-01 Związek poliorganosiloksanowy, sposób jego wytwarzania i zawierająca go żywica kopoliwęglanowa
JP2016523659A JP6150945B2 (ja) 2013-07-01 2014-07-01 ポリオルガノシロキサン化合物、製造方法およびこれを含むコーポリカーボネート樹脂
US14/635,668 US9267034B2 (en) 2013-07-01 2015-03-02 Polyorganosiloxane compound, method for preparing the same, and copolycarbonate resin comprising the same
US14/823,756 US9452969B2 (en) 2013-07-01 2015-08-11 Polyorganosiloxane compound, method for preparing the same, and copolycarbonate resin comprising the same

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
KR10-2013-0076439 2013-07-01
KR20130076449 2013-07-01
KR10-2013-0076449 2013-07-01
KR20130076439 2013-07-01
KR1020140080439A KR101566837B1 (ko) 2013-07-01 2014-06-30 폴리오르가노실록산 화합물의 제조방법 및 이를 포함하는 코폴리카보네이트 수지
KR10-2014-0080436 2014-06-30
KR10-2014-0080439 2014-06-30
KR1020140080436A KR101563269B1 (ko) 2013-07-01 2014-06-30 폴리오르가노실록산 화합물 및 이를 포함하는 코폴리카보네이트 수지

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/635,668 Continuation US9267034B2 (en) 2013-07-01 2015-03-02 Polyorganosiloxane compound, method for preparing the same, and copolycarbonate resin comprising the same

Publications (1)

Publication Number Publication Date
WO2015002427A1 true WO2015002427A1 (ko) 2015-01-08

Family

ID=53814888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/005836 Ceased WO2015002427A1 (ko) 2013-07-01 2014-07-01 폴리오르가노실록산 화합물, 제조방법 및 이를 포함하는 코폴리카보네이트 수지

Country Status (6)

Country Link
US (2) US9267034B2 (enExample)
EP (1) EP3018165B1 (enExample)
JP (2) JP6150945B2 (enExample)
CN (2) CN104837895B (enExample)
PL (1) PL3018165T3 (enExample)
WO (1) WO2015002427A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016004286A1 (en) * 2014-07-03 2016-01-07 Momentive Performance Materials Inc. Ester-functional polysiloxanes and copolymers made therefrom
US20180334537A1 (en) * 2015-11-06 2018-11-22 Lg Chem, Ltd. Copolycarbonate and composition comprising the same (as amended)
CN111479848A (zh) * 2017-12-18 2020-07-31 科思创德国股份有限公司 使用基于氯代烃的有机溶剂制备聚碳酸酯的方法

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101779188B1 (ko) 2014-09-05 2017-09-15 주식회사 엘지화학 코폴리카보네이트 및 이를 포함하는 조성물
KR101685665B1 (ko) 2014-12-04 2016-12-12 주식회사 엘지화학 코폴리카보네이트 및 이를 포함하는 조성물
KR20160067714A (ko) * 2014-12-04 2016-06-14 주식회사 엘지화학 코폴리카보네이트 및 이를 포함하는 물품
CN108148202B (zh) * 2016-12-02 2021-01-01 广东生益科技股份有限公司 一种苯乙烯基聚硅苯醚树脂及其制备方法和应用
JP6920917B2 (ja) * 2017-07-28 2021-08-18 上野製薬株式会社 ６−ヒドロキシ−２−ナフトエ酸アルケニルエステルおよびその製造方法
JP2019026590A (ja) * 2017-07-28 2019-02-21 上野製薬株式会社 ４−（２−オキシラニルメトキシ）安息香酸アルケニルエステルおよびその製造方法
CN109836565B (zh) * 2017-11-29 2022-01-07 万华化学集团股份有限公司 一种硅氧烷共聚碳酸酯及其制备方法
JP7330975B2 (ja) * 2017-12-18 2023-08-22 コベストロ、ドイチュラント、アクチエンゲゼルシャフト 塩素化炭化水素に基づく有機溶媒を使用したポリカーボネートの製造方法
CN110804166A (zh) * 2019-10-30 2020-02-18 濮阳市盛通聚源新材料有限公司 一种新型抗紫外共聚聚碳酸酯的制备方法
KR20220005912A (ko) * 2020-07-07 2022-01-14 현대모비스 주식회사 광투과성 성형품 및 자동차 내장재
JPWO2022260078A1 (enExample) * 2021-06-09 2022-12-15

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10204179A (ja) * 1997-01-21 1998-08-04 Toray Dow Corning Silicone Co Ltd ポリオルガノシロキサンおよびその製造方法
US5932677A (en) 1993-05-27 1999-08-03 General Electric Company Terpolymer having aromatic polyester, polysiloxane and polycarbonate segments
JP3195848B2 (ja) 1993-03-16 2001-08-06 出光興産株式会社 ポリカーボネート共重合体の製造方法
KR20020016922A (ko) 1999-07-27 2002-03-06 로버트 비. 스틸레스 콘택트 렌즈 재료
US20050187372A1 (en) * 2003-02-21 2005-08-25 General Electric Company Translucent thermoplastic composition, method for making the composition and articles molded there from
KR20120050968A (ko) * 2009-07-29 2012-05-21 테이진 카세이 가부시키가이샤 폴리카보네이트-폴리디오르가노실록산 공중합체
KR20120098769A (ko) * 2009-12-10 2012-09-05 이데미쓰 고산 가부시키가이샤 폴리카보네이트-폴리오르가노실록산 공중합체, 그 제조 방법 및 그 공중합체를 함유하는 폴리카보네이트 수지
WO2013058214A1 (ja) * 2011-10-18 2013-04-25 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及びその製造方法

Family Cites Families (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1693432A (en) * 1922-05-12 1928-11-27 Winthrop Chem Co Therapeutically-active aromatic compound containing mercury in a lateral chain and process of making the same
US4233208A (en) * 1978-07-12 1980-11-11 Ciba-Geigy Corporation Polymer compositions stabilized with hindered phenyl secondary phosphites
US4241011A (en) 1979-09-24 1980-12-23 Basf Wyandotte Corporation Antifreeze containing carboxysiloxane metal salts and hydroxybenzoic acid as pH buffer and corrosion inhibitor
JPS5673006A (en) * 1979-11-16 1981-06-17 Kuraray Co Ltd Fungicide for agriculture and horticulture containing benzoic ester
JPS5692247A (en) * 1979-12-27 1981-07-25 T Hasegawa Co Ltd 3-methyl-3-buten-1-ol ester, its preparation and application
US4387047A (en) * 1980-02-13 1983-06-07 Firmenich Sa Esters of 1,3-dimethyl-but-3-en-1-yl, their utilization as perfuming and flavoring ingredients and compositions containing same
US4788321A (en) * 1986-12-29 1988-11-29 Daikin Industries, Ltd. Perfluoroalkenyloxybenzoic acid derivative, process for preparing the same and prepolymer of the derivative
US5155253A (en) * 1988-06-30 1992-10-13 Union Carbide Chemicals & Plastics Technology Corporation Transvinylation process for the preparation of thermally labile vinyl compounds and for vinyl compounds prepared from thermally labile acids
JP2631739B2 (ja) * 1989-02-27 1997-07-16 信越化学工業株式会社 フェノール基含有シロキサン化合物
US5243009A (en) * 1989-03-06 1993-09-07 General Electric Company Hydroxyarylestersiloxanes
US4879378A (en) * 1989-03-30 1989-11-07 Union Carbide Chemicals And Plastics Company Inc. Polysiloxanes with pendant sterically hindered phenol moiety connected to the silicon atom via a carbonylyoxy-containing link
FR2649977B1 (fr) * 1989-07-18 1991-10-04 Cird Esters bi-aromatiques, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique
US5239018A (en) 1989-09-06 1993-08-24 Exxon Chemical Patents Inc. Liquid polymer and polyol compositions, and process for preparing phenol-functional polymer
LU87821A1 (fr) * 1990-10-12 1992-05-25 Cird Galderma Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique
IT1251572B (it) 1991-09-11 1995-05-17 Enichem Sintesi Stabilizzanti polisilossanici contenenti gruppi fenolici stericamente impediti e gruppi reattivi
DE4331608A1 (de) * 1993-09-17 1995-03-23 Goldschmidt Ag Th Mit Acrylatgruppen modifizierte Organopolysiloxane
JPH0873882A (ja) 1994-09-07 1996-03-19 Asahi Chem Ind Co Ltd 均一系の電気粘性流体
JP3601125B2 (ja) * 1995-08-31 2004-12-15 ユニマテック株式会社 新規なアクリル共重合体エラストマー、そのブレンドゴムおよびブレンドゴム組成物
JP3756576B2 (ja) * 1995-11-29 2006-03-15 東レ・ダウコーニング株式会社 ヒドロキシフェニル基含有ポリオルガノシロキサン
US6316500B1 (en) * 1999-01-05 2001-11-13 Isp Investments Inc. Aliphatically unsaturated hydroxy benzoates and preservative compositions thereof
JP4525951B2 (ja) * 1999-02-03 2010-08-18 塩野義製薬株式会社 ジアゾケトン基を有する固相粒子
JP4525881B2 (ja) 2000-03-29 2010-08-18 三菱瓦斯化学株式会社 ポリカーボネート樹脂および光学部材
DE60125670T2 (de) * 2000-09-14 2007-10-04 Firmenich S.A. Verwendung von ungesättigten Estern als Duftstoffe
US6630562B2 (en) * 2001-01-16 2003-10-07 Mitsubishi Gas Chemical Company, Inc. Polycarbonate resin
KR20040057404A (ko) * 2002-12-26 2004-07-02 주식회사 씨트리 알리벤돌 및 그 중간체의 제조방법
WO2004076512A2 (en) * 2003-02-21 2004-09-10 General Electric Company Transparent and high-heat polycarbonate-polysiloxane copolymers and transparent blends with polycarbonate and a process for preparing same
GB0416428D0 (en) * 2004-07-23 2004-08-25 Givaudan Sa Organic compound
KR100676301B1 (ko) 2004-10-21 2007-01-30 주식회사 엘지화학 실록산계 코폴리카보네이트의 제조방법
CN1272301C (zh) * 2005-04-28 2006-08-30 武汉大学 4,4'－二羟基二苯甲酮的制备方法
GB0509227D0 (en) * 2005-05-05 2005-06-15 Chroma Therapeutics Ltd Intracellular enzyme inhibitors
BRPI0617685A2 (pt) * 2005-11-17 2018-07-03 Firmenich & Cie uso de um composto, composto, composição perfumante, e, artigo perfumado
KR100713102B1 (ko) 2007-02-07 2007-05-02 주식회사 엘지화학 스프레이 결정화 방법을 사용한 실록산계코폴리카보네이트의 제조방법
CN101622219A (zh) * 2007-03-01 2010-01-06 日本瑞翁株式会社 可聚合的液晶化合物，可聚合的液晶组合物，液晶聚合物，和光学各向异性物质
US7888447B2 (en) 2007-03-29 2011-02-15 Sabic Innovative Plastics Ip B.V. Polycarbonate-polysiloxane copolymers, methods for the preparation thereof, and articles derived therefrom
MX2011001119A (es) * 2008-07-31 2011-03-02 Nicox Sa Glucocorticoides unidos a esteres de nitrato por medio de un enlazador aromatico en la posicion 21 y su uso en oftalmololgia.
JP2010083918A (ja) * 2008-09-29 2010-04-15 Dnp Fine Chemicals Co Ltd 活性エネルギー線硬化型樹脂組成物及びそれを用いてなる印刷物
US9458315B2 (en) 2009-08-25 2016-10-04 Sabic Global Technologies B.V. Flame retardant thermoplastic polycarbonate compositions and films made therefrom
CN102093220B (zh) * 2009-12-11 2014-12-10 Dic株式会社 羧酸的制备方法、羧酸烯丙酯
KR101332434B1 (ko) * 2010-08-26 2013-11-22 제일모직주식회사 비스하이드록시아릴실록산 및 그의 제조 방법
CN102153530A (zh) * 2011-02-12 2011-08-17 北京欧格瑞化学科技有限公司 一种合成决奈达隆关键中间体的新方法
JP2012177060A (ja) * 2011-02-28 2012-09-13 Mitsubishi Electric Corp 樹脂組成物及び樹脂硬化物
US9006324B2 (en) * 2011-03-31 2015-04-14 Sabic Global Technologies B.V. Flame retardant polycarbonate compositions, methods of manufacture, and articles formed therefrom
JP5966500B2 (ja) * 2011-05-02 2016-08-10 株式会社リコー シリコーン化合物、該シリコーン化合物を用いた光硬化型液体インク及びその製造方法
KR101448058B1 (ko) 2011-10-31 2014-10-10 주식회사 삼양사 저온 내충격성이 향상된 폴리카보네이트 수지 조성물 및 그 제조방법
CN102584683B (zh) * 2012-02-29 2014-12-24 中国人民解放军第四军医大学 Tempol类衍生物的合成及辐射防护作用

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3195848B2 (ja) 1993-03-16 2001-08-06 出光興産株式会社 ポリカーボネート共重合体の製造方法
US5932677A (en) 1993-05-27 1999-08-03 General Electric Company Terpolymer having aromatic polyester, polysiloxane and polycarbonate segments
JPH10204179A (ja) * 1997-01-21 1998-08-04 Toray Dow Corning Silicone Co Ltd ポリオルガノシロキサンおよびその製造方法
KR20020016922A (ko) 1999-07-27 2002-03-06 로버트 비. 스틸레스 콘택트 렌즈 재료
US20050187372A1 (en) * 2003-02-21 2005-08-25 General Electric Company Translucent thermoplastic composition, method for making the composition and articles molded there from
KR20120050968A (ko) * 2009-07-29 2012-05-21 테이진 카세이 가부시키가이샤 폴리카보네이트-폴리디오르가노실록산 공중합체
KR20120098769A (ko) * 2009-12-10 2012-09-05 이데미쓰 고산 가부시키가이샤 폴리카보네이트-폴리오르가노실록산 공중합체, 그 제조 방법 및 그 공중합체를 함유하는 폴리카보네이트 수지
WO2013058214A1 (ja) * 2011-10-18 2013-04-25 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及びその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP3018165A4

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016004286A1 (en) * 2014-07-03 2016-01-07 Momentive Performance Materials Inc. Ester-functional polysiloxanes and copolymers made therefrom
US20160002410A1 (en) * 2014-07-03 2016-01-07 Momentive Performance Materials Inc. Ester-functional polysiloxanes and copolymers made therefrom
US9518182B2 (en) 2014-07-03 2016-12-13 Momentive Performance Materials, Inc. Ester-functional polysiloxanes and copolymers made therefrom
JP2017520663A (ja) * 2014-07-03 2017-07-27 モメンティブ パフォーマンス マテリアルズ インコーポレイテッド エステル官能性ポリシロキサンおよびそれから作られるコポリマー
US9957357B2 (en) 2014-07-03 2018-05-01 Momentive Performance Materials, Inc. Ester-functional polysiloxanes and copolymers made therefrom
EP3164447B1 (en) * 2014-07-03 2019-10-09 Momentive Performance Materials Inc. Ester-functional polysiloxanes and copolymers made therefrom
US20180334537A1 (en) * 2015-11-06 2018-11-22 Lg Chem, Ltd. Copolycarbonate and composition comprising the same (as amended)
US10526445B2 (en) * 2015-11-06 2020-01-07 Lg Chem, Ltd. Copolycarbonate and composition comprising the same
CN111479848A (zh) * 2017-12-18 2020-07-31 科思创德国股份有限公司 使用基于氯代烃的有机溶剂制备聚碳酸酯的方法
CN111479848B (zh) * 2017-12-18 2022-12-23 科思创德国股份有限公司 使用基于氯代烃的有机溶剂制备聚碳酸酯的方法

Also Published As

Publication number Publication date
JP2016190850A (ja) 2016-11-10
JP2016528327A (ja) 2016-09-15
EP3018165B1 (en) 2019-06-12
CN107266318A (zh) 2017-10-20
US20150315380A1 (en) 2015-11-05
JP6235067B2 (ja) 2017-11-22
EP3018165A4 (en) 2016-06-22
US9452969B2 (en) 2016-09-27
JP6150945B2 (ja) 2017-06-21
CN107266318B (zh) 2020-07-03
US20160145187A1 (en) 2016-05-26
US9267034B2 (en) 2016-02-23
PL3018165T3 (pl) 2019-11-29
EP3018165A1 (en) 2016-05-11
CN104837895A (zh) 2015-08-12
CN104837895B (zh) 2017-06-06

Similar Documents

Publication Publication Date Title
WO2015002427A1 (ko) 폴리오르가노실록산 화합물, 제조방법 및 이를 포함하는 코폴리카보네이트 수지
WO2015041441A1 (ko) 코폴리카보네이트 수지 및 이를 포함하는 물품
WO2013066002A1 (en) Polysiloxane-polycarbonate copolymer and method of manufacturing the same
WO2013066000A1 (en) Polycarbonate resin composition having improved low-temperature impact resistance and method of manufacturing the same
WO2011122767A2 (ko) 히드록시 말단 실록산, 폴리실록산-폴리카보네이트 공중합체 및 그 제조 방법
WO2013100494A1 (en) Method of preparing polysiloxane-polycarbonate copolymer
WO2012060516A1 (ko) 폴리카보네이트 수지 및 상기 폴리카보네이트 수지를 포함하는 열가소성 수지 조성물
WO2020055178A1 (ko) 디올 화합물, 폴리카보네이트 및 이의 제조방법
WO2013100606A1 (en) Flame-retardant thermoplastic resin composition and molded article thereof
WO2017126901A1 (ko) 폴리에스테르-폴리카보네이트 공중합체 및 그 제조방법
WO2014204146A1 (ko) 난연성과 투명성이 우수한 열가소성 공중합체 수지 및 그 제조방법
WO2015002429A1 (ko) 히드록시 캡핑 단량체, 이의 폴리카보네이트 및 이를 포함하는 물품
WO2013047955A1 (ko) 폴리카보네이트 및 그의 제조 방법
WO2020060148A1 (ko) 내충격성, 난연성 및 투명도가 우수한 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법
WO2014092243A1 (ko) 폴리카보네이트 수지, 그 제조방법 및 이를 포함하는 성형품
KR101637399B1 (ko) 폴리오르가노실록산 화합물 및 이를 포함하는 코폴리카보네이트 수지
WO2013100288A1 (ko) 분지상 폴리카보네이트-폴리실록산 공중합체 및 그 제조방법
WO2015178676A1 (ko) 투명성 및 내충격성이 향상된 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법
WO2016195312A1 (ko) 폴리카보네이트 수지 및 이의 제조방법
WO2013176349A1 (ko) 신규 폴리실록산, 그 제조방법 및 이를 포함하는 폴리카보네이트-폴리실록산 공중합체
WO2023234584A1 (ko) 폴리카보네이트 공중합체
WO2021215838A1 (ko) 히드록시 말단 폴리실록산 혼합물을 이용한 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법
WO2023282559A1 (ko) 히드록시페닐-말단 폴리실록산, 이를 반복 단위로서 포함하는 투명성이 우수하고 난연성이 향상된 폴리실록산-폴리카보네이트 공중합체, 및 그 공중합체 제조방법
WO2016003132A1 (ko) 투명성 및 저온 내충격성이 향상된 폴리실록산-폴리카보네이트 공중합체 및 그 제조방법
WO2020032721A1 (ko) 폴리카보네이트 및 이의 제조방법

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14819695

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2014819695

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2016523659

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE