EP3383932A1 - Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques - Google Patents

Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques

Info

Publication number
EP3383932A1
EP3383932A1 EP16819348.0A EP16819348A EP3383932A1 EP 3383932 A1 EP3383932 A1 EP 3383932A1 EP 16819348 A EP16819348 A EP 16819348A EP 3383932 A1 EP3383932 A1 EP 3383932A1
Authority
EP
European Patent Office
Prior art keywords
polyester
units
dianhydrohexitol
temperature
naphthalenediol
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.)
Pending
Application number
EP16819348.0A
Other languages
German (de)
English (en)
French (fr)
Inventor
Nicolas JACQUEL
Gabriel DEGAND
René SAINT-LOUP
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.)
Roquette Freres SA
Original Assignee
Roquette Freres SA
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
Application filed by Roquette Freres SA filed Critical Roquette Freres SA
Publication of EP3383932A1 publication Critical patent/EP3383932A1/fr
Pending legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/724—Permeability to gases, adsorption
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/726—Permeability to liquids, absorption
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/70—Other properties
    • B32B2307/732—Dimensional properties
    • B32B2307/734—Dimensional stability
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/202—LCD, i.e. liquid crystal displays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2551/00—Optical elements
    • 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
    • C08G2250/00—Compositions for preparing crystalline polymers
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses

Definitions

  • the haze and the transmittance of the sample are measured according to the ASTM D1003 and ASTM D1003-95 methods on a polyester injected part according to the invention.
  • the number of ABBE is calculated according to the formula below from three refractive index measurements taken at 589 nm (nD: sodium D-line), 486 nm (nF: hydrogen F-line) and 656 nm (nC: C line of hydrogen).
  • the unit (A) is 1, 4: 3,6-dianhydrohexitol.
  • the 1,4: 3,6-dianhydrohexitols have the disadvantage of being secondary diols that are not very reactive in the manufacture of polyesters.
  • 1,4: 3,6-Dianhydrohexitol (A) may be isosorbide, isomannide, isoidide, or a mixture thereof.
  • 1,4: 3,6-dianhydrohexitol (A) is isosorbide.
  • Isosorbide, isomannide and isoidide can be obtained respectively by dehydration of sorbitol, mannitol and iditol.
  • isosorbide it is marketed by the Applicant under the brand name POLYSORB® P.
  • the polyester according to the invention is free of cyclohexanedimethanol units.
  • the invention also relates to a method of manufacturing the polyester according to the invention. This process comprises:
  • the additive useful for the composition according to the invention may also comprise opacifying agents, dyes and pigments. They can be chosen from cobalt acetate and the following compounds: HS-325 Sandoplasl® RED BB (which is a compound carrying an azo function also known as Solvent Red 195), HS-510 Sandoplasl® Blue 2B which is an anthraquinone, Polysynthren® Blue R, and Clariant® RSB Violet.
  • the thermal properties of the polyesters were measured by differential scanning calorimetry (DSC): the sample is first heated under a nitrogen atmosphere in an open crucible of 10 to 320%: (1 ⁇ m-1), cooled to 10%: (10%: min-1) then heated to 320%: under the same conditions as the first stage.
  • the glass transition temperatures were taken at the midpoint of the second heating.
  • the possible crystallization temperatures are determined on the exothermic peak (onset of the peak).
  • the possible melting temperatures are determined on the endothermic peak (onset of the peak) in the second heating. In the same way the determination of the enthalpy of fusion (area under the curve) is carried out at the second heating.
  • the polymer obtained is an amorphous material whose glass transition is ⁇ 49 ° C and the reduced viscosity of 54.9 ml / g (concentration at 5 g / l in 2-chlorophenol 35 ⁇ ).
  • Analysis of the final polyester by NMR shows that 27% of Isosorbide (relative to the diols) were introduced into the polymer chains.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyesters Or Polycarbonates (AREA)
EP16819348.0A 2015-12-02 2016-12-02 Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques Pending EP3383932A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR1561753A FR3044665A1 (fr) 2015-12-02 2015-12-02 Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques
FR1651205A FR3044667B1 (fr) 2015-12-02 2016-02-15 Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques
PCT/FR2016/053180 WO2017093685A1 (fr) 2015-12-02 2016-12-02 Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques

Publications (1)

Publication Number Publication Date
EP3383932A1 true EP3383932A1 (fr) 2018-10-10

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EP16819348.0A Pending EP3383932A1 (fr) 2015-12-02 2016-12-02 Copolyesters thermoplastiques aromatiques comprenant du 1,4 : 3,6-dianhydrohexitol et divers diols cycliques

Country Status (9)

Country Link
US (1) US20180362707A1 (ko)
EP (1) EP3383932A1 (ko)
JP (1) JP2018536073A (ko)
KR (1) KR20180089418A (ko)
CN (1) CN108431078B (ko)
CA (1) CA3006905A1 (ko)
FR (2) FR3044665A1 (ko)
MX (1) MX2018006685A (ko)
WO (1) WO2017093685A1 (ko)

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KR102670942B1 (ko) 2016-02-04 2024-05-31 에스케이케미칼 주식회사 내열성 및 용제 용해성이 우수한 폴리에스테르 수지 및 이를 함유하는 코팅 조성물
FR3065958B1 (fr) * 2017-05-05 2020-09-04 Roquette Freres Procede de fabrication d'un materiau composite
CH715228A1 (de) * 2018-08-02 2020-02-14 Alpla Werke Alwin Lehner Gmbh & Co Kg Preform aus Polyester.
KR102478598B1 (ko) * 2019-08-30 2022-12-15 코오롱인더스트리 주식회사 바이오매스 유래 환형 단량체를 포함하는 고분자 화합물 및 그의 제조방법
CN111072940B (zh) * 2019-11-28 2021-09-28 中国科学院宁波材料技术与工程研究所 基于螺环乙二醇的共聚酯及其制备方法、制品
FR3105232B1 (fr) 2019-12-20 2021-12-24 Roquette Freres Procédé de fabrication d’un polyester contenant au moins un motif 1,4 : 3,6-dianhydrohexitol à coloration réduite et taux d’incorporation dudit motif améliorés
CN111303394A (zh) * 2020-04-20 2020-06-19 河南功能高分子膜材料创新中心有限公司 一种改性耐高温聚酯的制备方法及改性耐高温聚酯
CN111471167B (zh) * 2020-05-12 2022-08-09 河南功能高分子膜材料创新中心有限公司 一种改性耐高温抗水解共聚聚酯
TWI800981B (zh) * 2021-11-16 2023-05-01 南亞塑膠工業股份有限公司 聚合物樹脂及其製造方法

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Publication number Publication date
CA3006905A1 (fr) 2017-06-08
WO2017093685A1 (fr) 2017-06-08
JP2018536073A (ja) 2018-12-06
CN108431078A (zh) 2018-08-21
FR3044667B1 (fr) 2020-02-14
US20180362707A1 (en) 2018-12-20
CN108431078B (zh) 2021-08-06
KR20180089418A (ko) 2018-08-08
FR3044665A1 (fr) 2017-06-09
MX2018006685A (es) 2018-08-24
FR3044667A1 (fr) 2017-06-09

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