JP2020527634A - ポリエステルを調整するための方法 - Google Patents
ポリエステルを調整するための方法 Download PDFInfo
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- aluminosilicate
- dicarboxylic acid
- process according
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- esterification
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- 229920000728 polyester Polymers 0.000 title claims abstract description 24
- 229910000323 aluminium silicate Inorganic materials 0.000 claims abstract description 44
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 32
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims abstract description 31
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 238000005886 esterification reaction Methods 0.000 claims description 23
- 230000032050 esterification Effects 0.000 claims description 20
- 238000006068 polycondensation reaction Methods 0.000 claims description 17
- 239000012467 final product Substances 0.000 claims description 8
- 229910021536 Zeolite Inorganic materials 0.000 claims description 7
- 239000010457 zeolite Substances 0.000 claims description 7
- 230000006866 deterioration Effects 0.000 claims description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- -1 polyethylene terephthalate Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000004629 polybutylene adipate terephthalate Substances 0.000 description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 2
- 239000004631 polybutylene succinate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
ジカルボン酸とブタンジオールとのモル比が0.5〜1.5である、
エステル化温度が165℃〜260℃であるが、ジカルボン酸の熱劣化温度よりも低い、
圧力が1200mbar〜200mbarである、
触媒濃度が最終生成物を基準として25ppm〜200ppmである、
アルミノケイ酸塩の濃度が最終生成物を基準として100〜1000ppmである、
うちの少なくとも1つを適用することにより、エステル化を実施することができる。
温度が230℃〜260℃であるが、ジカルボン酸の熱劣化温度よりも低い、
圧力が600mbar〜20mbarである、
うちの少なくとも1つを適用することにより、予備重縮合を実施することができる。
温度が235℃〜265℃であるが、ジカルボン酸の熱劣化温度よりも低い、
圧力が1mbar未満であればよい、
うちの少なくとも1つを適用することにより、重縮合を実施することができる。
テレフタル酸(TPA)1265.5g、アジピン酸1352.8g、ブタンジオール266.1g、触媒であるTyzor TnBT(Dorf Ketal)すなわち、市販のオルトチタン酸テトラブチル触媒(最終生成物に関連してTiが50ppm)1.29g−式Na2O・Al2O3・2SiO2・nH2Oで表され、例えばKOESTROLITH(登録商標)4AP-TRから調製された、粒径d500.1〜0.5μm(最終生成物に関連して500ppm)のアルミノケイ酸塩粉末すなわち孔径4Åの4Aタイプのゼオライト粉末1.82gを、エステル化段階で55分間処理し、開始から10分後に目標圧力の600mbarに達した。水の分離であるエステル化反応を温度173℃(留出液の最初の一滴)で開始し、エステル化終了までの間に220℃まで上昇させた。
アルミノケイ酸塩を使用しなかったこと以外、実施例1と同じ手順を実施した。
Claims (14)
- 触媒の存在下でジカルボン酸をブタンジオールと反応させることを含み、アルミノケイ酸塩が存在する、ポリエステルを調製するためのプロセス。
- エステル化、予備重縮合、重縮合の工程を含む、請求項1に記載のプロセス。
- 前記アルミノケイ酸塩は、4A型ゼオライトである、請求項1または2に記載のプロセス。
- 前記アルミノケイ酸塩は、式Na2O・Al2O3・2SiO2・nH2Oで表される、請求項1〜3のいずれか1項に記載のプロセス。
- 前記アルミノケイ酸塩は、孔径が約4Åである、請求項1〜4のいずれか1項に記載のプロセス。
- 前記アルミノケイ酸塩は、粒径d50が0.1〜0.5μmである、請求項1〜5のいずれか1項に記載のプロセス。
- 前記アルミノケイ酸塩は、合成アルミノケイ酸塩および/または結晶性アルミノケイ酸塩である、請求項1〜6のいずれか1項に記載のプロセス。
- 前記触媒は、オルトチタン酸テトラブチルである、請求項1〜7のいずれか1項に記載のプロセス。
- 前記ジカルボン酸は、1つまたは2つの芳香環を有する芳香族ジカルボン酸であるか、2〜16個の炭素原子を有する脂肪族ジカルボン酸である、請求項1〜8のいずれか1項に記載のプロセス。
- 前記触媒の濃度の前記アルミノケイ酸塩の濃度に対する関係は、2:1から1:40である、請求項1〜9のいずれか1項に記載のプロセス。
- 前記エステル化は、以下のパラメーターの少なくとも1つを適用することにより実施することができる、請求項1〜10のいずれか1項に記載のプロセス:
ジカルボン酸とブタンジオールとのモル比が0.5〜1.5である;
エステル化温度が165℃〜260℃であるが、前記ジカルボン酸の熱劣化温度よりも低い;
圧力が1200mbar〜200mbarである;
触媒の濃度が最終生成物を基準として25ppm〜200ppmである;及び
前記アルミノケイ酸塩の濃度が最終生成物を基準として100〜1000ppmである。 - 前記予備重合は、以下のパラメーターすなわち、
温度が230℃〜260℃であるが、前記ジカルボン酸の熱劣化温度よりも低い、
圧力が600mbar〜20mbarである、
うちの少なくとも1つを適用することにより実施することができる、請求項1〜11のいずれか1項に記載のプロセス。 - 前記縮重合は、以下のパラメーターの少なくとも1つを適用することにより実施することができる、請求項1〜12のいずれか1項に記載のプロセス
温度が235℃〜265℃であるが、前記ジカルボン酸の熱劣化温度よりも低い、
圧力が1mbar未満である、
。 - 触媒の存在下でジカルボン酸をブタンジオールと反応させることを含む、請求項1〜13のいずれか1項に規定するポリエステルを調製するためのプロセスにおける、アルミノケイ酸塩の使用。
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PCT/EP2017/068057 WO2019015745A1 (en) | 2017-07-17 | 2017-07-17 | PROCESS FOR THE PREPARATION OF POLYESTERS |
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JP2020527634A true JP2020527634A (ja) | 2020-09-10 |
JP7499173B2 JP7499173B2 (ja) | 2024-06-13 |
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Country Status (13)
Country | Link |
---|---|
US (1) | US20200157277A1 (ja) |
EP (1) | EP3655459B1 (ja) |
JP (1) | JP7499173B2 (ja) |
KR (1) | KR102374426B1 (ja) |
CN (1) | CN110914332B (ja) |
BR (1) | BR112020000601B1 (ja) |
DK (1) | DK3655459T3 (ja) |
EA (1) | EA202090271A1 (ja) |
ES (1) | ES2914682T3 (ja) |
LT (1) | LT3655459T (ja) |
PH (1) | PH12020550022A1 (ja) |
PL (1) | PL3655459T3 (ja) |
WO (1) | WO2019015745A1 (ja) |
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CN113354928B (zh) * | 2021-06-29 | 2022-02-15 | 浙江中邦塑胶股份有限公司 | 一种用于制作降解膜的生物塑料及制备方法 |
Citations (5)
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JPS5275684A (en) * | 1975-11-26 | 1977-06-24 | Emery Industries Inc | Transition metal catalysts*manufacture and use thereof |
JPH05310902A (ja) * | 1992-01-21 | 1993-11-22 | Eastman Kodak Co | 高分子量ポリエステルの製造方法 |
DE19627591A1 (de) * | 1996-07-09 | 1997-01-02 | Thueringisches Inst Textil | Verfahren zur katalytischen Beschleunigung der Polykondensation von Polyestern mit Silikaten |
JP2016132721A (ja) * | 2015-01-19 | 2016-07-25 | 三菱化学株式会社 | フィルム用ポリブチレンテレフタレートペレット及びその製造方法 |
JP2017193687A (ja) * | 2016-04-22 | 2017-10-26 | 三菱ケミカル株式会社 | フィルム用ポリブチレンテレフタレートペレット |
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US4032550A (en) * | 1975-11-26 | 1977-06-28 | Emery Industries, Inc. | Process for the production of esters |
DE4316138A1 (de) | 1993-05-14 | 1994-11-17 | Basf Ag | Verfahren zur Herstellung von Polytetrahydrofuran |
US5342902A (en) * | 1993-09-07 | 1994-08-30 | Eastman Chemical Company | Poly(ester-ether) compositions having increased thermal stability |
DE19638549A1 (de) | 1996-09-20 | 1998-03-26 | Zimmer Ag | Zeolith-Katalysator zur Polykondensation von Polyester |
JPH11106364A (ja) * | 1997-10-01 | 1999-04-20 | Teijin Ltd | ポリエステル中間原料の製造方法 |
DE19929790A1 (de) * | 1999-06-29 | 2001-01-04 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Polybutylenterephthalat aus Terephthalsäure und Butandiol |
DE19929791A1 (de) * | 1999-06-29 | 2001-02-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Polybutylenterephthalat aus Terephthalsäure und Butandiol |
JP2001172379A (ja) * | 1999-12-17 | 2001-06-26 | Toray Ind Inc | ゼオライトを用いたポリエステルの製造装置及びその製造方法 |
JP2006104292A (ja) * | 2004-10-04 | 2006-04-20 | Nippon Shokubai Co Ltd | ポリエステルの製法 |
US20060135668A1 (en) * | 2004-12-21 | 2006-06-22 | Hayes Richard A | Polyesters containing natural mineral materials, processes for producing such polyesters, and shaped articles produced therefrom |
JP5275684B2 (ja) | 2008-05-21 | 2013-08-28 | 花王株式会社 | 容器入り歯磨き組成物 |
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- 2017-07-17 EP EP17752012.9A patent/EP3655459B1/en active Active
- 2017-07-17 US US16/630,943 patent/US20200157277A1/en active Pending
- 2017-07-17 BR BR112020000601-7A patent/BR112020000601B1/pt active IP Right Grant
- 2017-07-17 LT LTEPPCT/EP2017/068057T patent/LT3655459T/lt unknown
- 2017-07-17 ES ES17752012T patent/ES2914682T3/es active Active
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- 2017-07-17 DK DK17752012.9T patent/DK3655459T3/da active
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JPS5275684A (en) * | 1975-11-26 | 1977-06-24 | Emery Industries Inc | Transition metal catalysts*manufacture and use thereof |
JPH05310902A (ja) * | 1992-01-21 | 1993-11-22 | Eastman Kodak Co | 高分子量ポリエステルの製造方法 |
DE19627591A1 (de) * | 1996-07-09 | 1997-01-02 | Thueringisches Inst Textil | Verfahren zur katalytischen Beschleunigung der Polykondensation von Polyestern mit Silikaten |
JP2016132721A (ja) * | 2015-01-19 | 2016-07-25 | 三菱化学株式会社 | フィルム用ポリブチレンテレフタレートペレット及びその製造方法 |
JP2017193687A (ja) * | 2016-04-22 | 2017-10-26 | 三菱ケミカル株式会社 | フィルム用ポリブチレンテレフタレートペレット |
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JP7499173B2 (ja) | 2024-06-13 |
KR20200032687A (ko) | 2020-03-26 |
EP3655459A1 (en) | 2020-05-27 |
KR102374426B1 (ko) | 2022-03-14 |
ES2914682T3 (es) | 2022-06-15 |
BR112020000601A2 (pt) | 2020-07-14 |
DK3655459T3 (da) | 2022-05-30 |
BR112020000601B1 (pt) | 2022-08-02 |
CN110914332A (zh) | 2020-03-24 |
EP3655459B1 (en) | 2022-03-02 |
CN110914332B (zh) | 2022-07-08 |
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US20200157277A1 (en) | 2020-05-21 |
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