Patent · US9353215B2 · B2 · US

Production method of polycarbonate resin

(11) Publication number

US9353215B2

(21) Application number

14/041,397

(22) Filing date

2013-09-30

(30) Priority date

2011-03-31

(43) Publication date

2016-05-31

(45) Date of grant

2016-05-31

(51) IPC

B29C 48/37; B29C 48/395; B29C 48/40; B29C 48/57; B32B 1/00; C08G 64/08; C08G 64/38; B29B 9/06; C08G 64/30; C08J 5/18

(52) CPC

C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 64/083, 64/305, 64/38
B29B Preparation or pretreatment of the material to be shaped; making granules or preforms; recovery of plastics or other constituents of waste material containing plastics: 7/002, 7/16, 7/28, 7/72, 7/7461, 7/748, 7/7485, 7/82, 7/845, 7/86, 9/06
B29C Shaping or joining of plastics; shaping of material in a plastic state, not otherwise provided for; after-treatment of the shaped products, e.g. repairing: 47/364, 47/385, 47/6056, 48/37, 48/397, 48/40, 48/57
B29K Indexing scheme associated with subclasses B29B, B29C or B29D, relating to moulding materials or to materials for {moulds, } reinforcements, fillers or preformed parts, e.g. inserts: 2069/00
C08J Working-up; general processes of compounding; after-treatment not covered by subclasses C08B, C08C, C08F, C08G or C08H: 2369/00, 5/18

(73) Assignee

Mitsubishi Chemical Corp

(72) Inventors

Masashi Yokogi; Shingo Namiki; Takehito Nagao; Masanori Yamamoto

(54) Title

Production method of polycarbonate resin

(57) Abstract

The present invention is a method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction by using a catalyst and using a dihydroxy compound and a carbonic acid diester as raw material monomers, and feeding the produced polycarbonate resin to an extruder, wherein the dihydroxy compound contains at least a dihydroxy compound having a moiety represented by formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by formula (1) contains a compound having a cyclic ether structure, and the temperature at the time of feeding the polycarbonate resin to the extruder is from 180° C. to less than 250° C., with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H CH 2 - O (1).

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Claims (17)

A method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester, and continuously feeding the produced polycarbonate resin to an extruder, wherein the polycarbonate is not solidified after the polycondensation and before being fed to the extruder, the dihydroxy compound contains a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by the following formula (1) contains a compound having a cyclic ether structure, and the temperature at the time of feeding the polycarbonate resin to the extruder is from 180° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H, wherein a barrel constituting the extruder has a plurality of heaters and all of the heaters are set to a temperature of 100° C. to less than 250° C.
The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin obtained via the extruder is from 80° C. to less than 145° C.
The method for producing a polycarbonate resin according to claim 1, wherein each of the heaters is set to a temperature not higher than the preset temperature of the heater adjacent to the polycarbonate resin feed side of the extruder.
The method for producing a polycarbonate resin according to claim 1, wherein the polycarbonate resin produced by polycondensation through a transesterification reaction is fed in a molten state to the extruder.
The method for producing a polycarbonate resin according to claim 1, wherein the extruder comprises a screw and wherein the screw of the extruder is composed of a plurality of elements, at least one of the elements is a kneading disc, and the total length of the kneading disc is 20% or less of the length of the screw as a whole.
The method for producing a polycarbonate resin according to claim 1, wherein assuming that the weight of the resin extruded per hour from the extruder is W (kg/h) and the cross-sectional area of the barrel of the extruder is S (m 2), the following formula (5) is satisfied: 12000≦ W/S≦ 60000 (5).
The method for producing a polycarbonate resin according to claim 1, wherein the reduced viscosity (η sp /c) of the polycarbonate resin obtained via the extruder, as measured in methylene chloride under the conditions of a concentration of 0.6 g/dL and a temperature of 20.0° C.±0.1° C., is from 0.3 to 1.2 dL/g.
The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin obtained via the extruder is from 90 to 140° C.
The method for producing a polycarbonate resin according to claim 1, wherein the content of an aromatic monohydroxy compound contained in said polycarbonate resin obtained via said extruder is less than 0.1 wt %.
The method for producing a polycarbonate resin according to claim 1, wherein the raw material monomers are filtered through a filter for raw material filtration before polycondensation.
The method for producing a polycarbonate resin according to claim 1, wherein said extruder kneads a heat stabilizer.
The method for producing a polycarbonate resin according to claim 1, wherein said catalyst is a compound of at least one metal selected from the group consisting of metals belonging to Group 2 of the long-form periodic table and lithium.
The method for producing a polycarbonate resin according to claim 1, wherein the dihydroxy compound having a moiety represented by formula (1) is isosorbide.
The method for producing a polycarbonate resin according to claim 1, wherein an alicyclic dihydroxy compound is further used as said dihydroxy compound.
A method for producing a polycarbonate resin pellet, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester, and continuously feeding the produced polycarbonate resin to an extruder, wherein said polycarbonate is not solidified after said polycondensation and before being fed to said extruder said dihydroxy compound contains at least a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the glass transition temperature of the polycarbonate resin fed to said extruder is from 80° C. to less than 145° C., and the temperature at the time of feeding said polycarbonate resin to said extruder is from 180° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H, wherein a barrel constituting the extruder has a plurality of heaters and all of the heaters are set to a temperature of 100° C. to less than 250° C.
A method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester as raw material monomers, and continuously feeding the produced polycarbonate resin to an extruder, wherein said polycarbonate is not solidified after said polycondensation and before being fed to said extruder, said dihydroxy compound contains at least a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by formula (1) is a compound having a cyclic ether structure, the barrel constituting said extruder has a plurality of heaters, and all of the heaters is set to a temperature of 100° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by the formula (1) is a part of - CH 2 - O - H.
The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin fed to said extruder is from 80° C. to less than 145° C., and the glass transition temperature of the polycarbonate resin obtained from said extruder is from 80° C. to less than 145° C.

Description

The present invention relates to a method for efficiently and stably producing a polycarbonate resin excellent in the thermal stability, hue and mechanical strength and less contaminated with an extraneous matter.

A polycarbonate resin is generally produced using bisphenols as a monomer ingredient and by making use of its superiority such as transparency, heat resistance and mechanical strength, is widely utilized as a so-called engineering plastic in the fields of electric•electronic parts, automotive parts, optical recording mediums, optics such as lens, and the like. However, in the application to an optical compensation film of, for example, a flat panel display that is rapidly spreading in recent years, higher optical characteristics such as low birefringence and low photoelastic coefficient are required, and the conventional polycarbonate resin using bisphenols as a monomer ingredient becomes incapable of meeting the requirement.

Also, the conventional polycarbonate resin is produced using a raw material derived from petroleum resources, but in recent years, depletion of petroleum resources is feared, and it is demanded to provide a polycarbonate resin using a raw material obtained from biomass resources such as plant. In addition, because of a concern that global warming due to increase or accumulation of carbon dioxide emissions may bring about climate change or the like, development of a polycarbonate resin using a plant-derived monomer as a raw material and being carbon neutral even when discarded after use is demanded.

Citations (28)

US4265852A
JPH05239333A
WO2004111106A1
JP2006028441A
JP2006232897A
JP2008024919A
WO2008120493A1
JP2008247953A
JP2009091404A
JP2009091417A
US20110003101A1
JP2009161745A
US20110034646A1
JP2010058410A
JP2010150539A
EP2371877A1
JP2011021171A
JP2010189581A
JP2011001454A
JP2011006553A
US8481625B2
US20120328855A1
US20130075480A1
US20130116365A1
US20130131271A1
JP2012046628A
US20130237649A1
US20140030505A1

Record as JSON

{
  "publication_number": "US9353215B2",
  "country": "US",
  "kind": "B2",
  "title": "Production method of polycarbonate resin",
  "abstract": "The present invention is a method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction by using a catalyst and using a dihydroxy compound and a carbonic acid diester as raw material monomers, and feeding the produced polycarbonate resin to an extruder, wherein the dihydroxy compound contains at least a dihydroxy compound having a moiety represented by formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by formula (1) contains a compound having a cyclic ether structure, and the temperature at the time of feeding the polycarbonate resin to the extruder is from 180° C. to less than 250° C., with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H CH 2 - O (1).",
  "claims": [
    "1. A method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester, and continuously feeding the produced polycarbonate resin to an extruder, wherein the polycarbonate is not solidified after the polycondensation and before being fed to the extruder, the dihydroxy compound contains a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by the following formula (1) contains a compound having a cyclic ether structure, and the temperature at the time of feeding the polycarbonate resin to the extruder is from 180° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H, wherein a barrel constituting the extruder has a plurality of heaters and all of the heaters are set to a temperature of 100° C. to less than 250° C.",
    "2. The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin obtained via the extruder is from 80° C. to less than 145° C.",
    "3. The method for producing a polycarbonate resin according to claim 1, wherein each of the heaters is set to a temperature not higher than the preset temperature of the heater adjacent to the polycarbonate resin feed side of the extruder.",
    "4. The method for producing a polycarbonate resin according to claim 1, wherein the polycarbonate resin produced by polycondensation through a transesterification reaction is fed in a molten state to the extruder.",
    "5. The method for producing a polycarbonate resin according to claim 1, wherein the extruder comprises a screw and wherein the screw of the extruder is composed of a plurality of elements, at least one of the elements is a kneading disc, and the total length of the kneading disc is 20% or less of the length of the screw as a whole.",
    "6. The method for producing a polycarbonate resin according to claim 1, wherein assuming that the weight of the resin extruded per hour from the extruder is W (kg/h) and the cross-sectional area of the barrel of the extruder is S (m 2), the following formula (5) is satisfied: 12000≦ W/S≦ 60000 (5).",
    "7. The method for producing a polycarbonate resin according to claim 1, wherein the reduced viscosity (η sp /c) of the polycarbonate resin obtained via the extruder, as measured in methylene chloride under the conditions of a concentration of 0.6 g/dL and a temperature of 20.0° C.±0.1° C., is from 0.3 to 1.2 dL/g.",
    "8. The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin obtained via the extruder is from 90 to 140° C.",
    "9. The method for producing a polycarbonate resin according to claim 1, wherein the content of an aromatic monohydroxy compound contained in said polycarbonate resin obtained via said extruder is less than 0.1 wt %.",
    "10. The method for producing a polycarbonate resin according to claim 1, wherein the raw material monomers are filtered through a filter for raw material filtration before polycondensation.",
    "11. The method for producing a polycarbonate resin according to claim 1, wherein said extruder kneads a heat stabilizer.",
    "12. The method for producing a polycarbonate resin according to claim 1, wherein said catalyst is a compound of at least one metal selected from the group consisting of metals belonging to Group 2 of the long-form periodic table and lithium.",
    "13. The method for producing a polycarbonate resin according to claim 1, wherein the dihydroxy compound having a moiety represented by formula (1) is isosorbide.",
    "14. The method for producing a polycarbonate resin according to claim 1, wherein an alicyclic dihydroxy compound is further used as said dihydroxy compound.",
    "15. A method for producing a polycarbonate resin pellet, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester, and continuously feeding the produced polycarbonate resin to an extruder, wherein said polycarbonate is not solidified after said polycondensation and before being fed to said extruder said dihydroxy compound contains at least a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the glass transition temperature of the polycarbonate resin fed to said extruder is from 80° C. to less than 145° C., and the temperature at the time of feeding said polycarbonate resin to said extruder is from 180° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by formula (1) is a part of - CH 2 - O - H, wherein a barrel constituting the extruder has a plurality of heaters and all of the heaters are set to a temperature of 100° C. to less than 250° C.",
    "16. A method for producing a polycarbonate resin, comprising performing polycondensation through a transesterification reaction with a catalyst and with a dihydroxy compound and a carbonic acid diester as raw material monomers, and continuously feeding the produced polycarbonate resin to an extruder, wherein said polycarbonate is not solidified after said polycondensation and before being fed to said extruder, said dihydroxy compound contains at least a dihydroxy compound having a moiety represented by the following formula (1) in a part of the structure, the dihydroxy compound having a moiety represented by formula (1) is a compound having a cyclic ether structure, the barrel constituting said extruder has a plurality of heaters, and all of the heaters is set to a temperature of 100° C. to less than 250° C.: CH 2 - O (1) with the proviso excluding the case where the moiety represented by the formula (1) is a part of - CH 2 - O - H.",
    "17. The method for producing a polycarbonate resin according to claim 1, wherein the glass transition temperature of the polycarbonate resin fed to said extruder is from 80° C. to less than 145° C., and the glass transition temperature of the polycarbonate resin obtained from said extruder is from 80° C. to less than 145° C."
  ],
  "description_excerpt": "The present invention relates to a method for efficiently and stably producing a polycarbonate resin excellent in the thermal stability, hue and mechanical strength and less contaminated with an extraneous matter.\n\nA polycarbonate resin is generally produced using bisphenols as a monomer ingredient and by making use of its superiority such as transparency, heat resistance and mechanical strength, is widely utilized as a so-called engineering plastic in the fields of electric•electronic parts, automotive parts, optical recording mediums, optics such as lens, and the like. However, in the application to an optical compensation film of, for example, a flat panel display that is rapidly spreading in recent years, higher optical characteristics such as low birefringence and low photoelastic coefficient are required, and the conventional polycarbonate resin using bisphenols as a monomer ingredient becomes incapable of meeting the requirement.\n\nAlso, the conventional polycarbonate resin is produced using a raw material derived from petroleum resources, but in recent years, depletion of petroleum resources is feared, and it is demanded to provide a polycarbonate resin using a raw material obtained from biomass resources such as plant. In addition, because of a concern that global warming due to increase or accumulation of carbon dioxide emissions may bring about climate change or the like, development of a polycarbonate resin using a plant-derived monomer as a raw material and being carbon neutral even when discarded after use is demanded.",
  "cpc": [
    "C08G 64/083",
    "B29B 7/002",
    "B29B 7/16",
    "B29B 7/28",
    "B29B 7/72",
    "B29B 7/7461",
    "B29B 7/748",
    "B29B 7/7485",
    "B29B 7/82",
    "B29B 7/845",
    "B29B 7/86",
    "B29B 9/06",
    "B29C 47/364",
    "B29C 47/385",
    "B29C 47/6056",
    "B29C 48/37",
    "B29C 48/397",
    "B29C 48/40",
    "B29C 48/57",
    "B29K 2069/00",
    "C08G 64/305",
    "C08G 64/38",
    "C08J 2369/00",
    "C08J 5/18"
  ],
  "ipc": [
    "B29C 48/37",
    "B29C 48/395",
    "B29C 48/40",
    "B29C 48/57",
    "B32B 1/00",
    "C08G 64/08",
    "C08G 64/38",
    "B29B 9/06",
    "C08G 64/30",
    "C08J 5/18"
  ],
  "assignees": [
    "Mitsubishi Chemical Corp"
  ],
  "inventors": [
    "Masashi Yokogi",
    "Shingo Namiki",
    "Takehito Nagao",
    "Masanori Yamamoto"
  ],
  "filing_date": "2013-09-30",
  "publication_date": "2016-05-31",
  "grant_date": "2016-05-31",
  "priority_date": "2011-03-31",
  "application_number": "US-201314041397-A",
  "family_id": "46931546",
  "cited_by_count": 2,
  "citations": [
    "US4265852A",
    "JPH05239333A",
    "WO2004111106A1",
    "JP2006028441A",
    "JP2006232897A",
    "JP2008024919A",
    "WO2008120493A1",
    "JP2008247953A",
    "JP2009091404A",
    "JP2009091417A",
    "US20110003101A1",
    "JP2009161745A",
    "US20110034646A1",
    "JP2010058410A",
    "JP2010150539A",
    "EP2371877A1",
    "JP2011021171A",
    "JP2010189581A",
    "JP2011001454A",
    "JP2011006553A",
    "US8481625B2",
    "US20120328855A1",
    "US20130075480A1",
    "US20130116365A1",
    "US20130131271A1",
    "JP2012046628A",
    "US20130237649A1",
    "US20140030505A1"
  ]
}

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