JP6371278B2 - ポリエステル樹脂の製造方法 - Google Patents
ポリエステル樹脂の製造方法 Download PDFInfo
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- JP6371278B2 JP6371278B2 JP2015513896A JP2015513896A JP6371278B2 JP 6371278 B2 JP6371278 B2 JP 6371278B2 JP 2015513896 A JP2015513896 A JP 2015513896A JP 2015513896 A JP2015513896 A JP 2015513896A JP 6371278 B2 JP6371278 B2 JP 6371278B2
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- polyester resin
- zinc
- esterification reaction
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- diol
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- 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
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, 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
- 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
- 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
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—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
- C08G63/78—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
- C08G63/86—Germanium, antimony, or compounds thereof
- C08G63/863—Germanium 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/916—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
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-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
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
また、本発明は、短い反応時間内に反応物質を高い効率で反応させ、前述した特性のポリエステル樹脂が提供できる製造方法を提供するためのものである。
7L容積の反応器に表1の含量で反応物及び亜鉛アセテート(エステル化反応触媒)を添加して混合し、前記混合物を2.0kg/cm2の圧力及び255℃条件で下記表1のES反応時間行なった(エステル化反応)。
比較例1及び2
下記表2による反応物の組成で使用し、リン系安定剤をエステル化反応初期に添加した点を除いて、実施例と同様な方法でポリエステルを製造した。
下記表2による反応物の組成で使用し、エステル化反応で亜鉛系触媒を使用しない点を除いて、実施例と同様な方法でポリエステルを製造した。
前記実施例及び比較例で得られたポリエステル樹脂の物性を下記方法で測定し、その結果を表1及び表2にそれぞれ示した。
150℃オルトクロロフェノール(OCP)に0.12%濃度にポリマーを溶解させた後、35℃の恒温槽でウベロード型粘度計を用いて測定した。
ポリエステル樹脂を300℃で5分間アニーリング(Annealing)し、常温に冷却させた後、昇温速度10℃/minで再びスキャン(2nd Scan)時のガラス転移温度(Glass−rubber transition temperature:Tg)を測定した。
Claims (13)
- テレフタル酸を含むジカルボン酸成分の残基;及び、
ジオール成分を基準として、イソソルビド5乃至60モル%、シクロヘキサンジメタノール10乃至80モル%、及び残量のその他のジオール化合物を含むジオール成分の残基を含み、
全体樹脂中に、中心金属原子基準に1乃至100ppmの亜鉛系触媒及び150ppm乃至300ppmのリン系安定剤を含有し、
1以下のカラーb値を有するポリエステル樹脂。 - 前記その他のジオール化合物は、脂肪族ジオール化合物及び芳香族ジオール化合物からなる群より選択された1種以上の化合物を含む請求項1に記載のポリエステル樹脂。
- 前記リン系安定剤は、リン酸、トリメチルホスフェート、トリエチルホスフェート、トリフェニルホスフェート、及びトリエチルホスホノアセテートからなる群より選択された1種以上の化合物を含む請求項1に記載のポリエステル樹脂。
- 前記亜鉛系触媒は、亜鉛アセテート、亜鉛アセテートジハイドレート、塩化亜鉛、硫酸亜鉛、硫化亜鉛、炭酸亜鉛、亜鉛シトレート、及びグルコン酸亜鉛からなる群より選択された1種以上を含む請求項1に記載のポリエステル樹脂。
- チタン系化合物、ゲルマニウム系化合物、アンチモン系化合物、アルミニウム系化合物及びスズ系化合物からなる群より選択された1種以上の重縮合反応触媒を全体樹脂中の1乃至100ppmの含量でさらに含む請求項1に記載のポリエステル樹脂。
- 亜鉛系化合物を含むエステル化反応触媒の存在下に、ジオール成分を基準として、イソソルビド5乃至60モル%、シクロヘキサンジメタノール10乃至80モル%及び残量のその他のジオール化合物を含むジオール成分とテレフタル酸を含むジカルボン酸成分をエステル化反応させる段階;
前記エステル化反応が80%以上行われた時点において、前記エステル化反応が進行している反応液にリン系安定剤を添加する段階;及び
前記エステル化反応生成物を重縮合反応させる段階を含み、
前記リン系安定剤は、合成される樹脂重量対比150ppm乃至300ppmの量で使用され、
前記ジオール成分またはジカルボン酸成分中の前記エステル化反応に参与しない未反応残量が20%未満である、請求項1に記載のポリエステル樹脂の製造方法。 - 前記エステル化反応でジカルボン酸成分:ジオール成分のモル比は、1:1.05乃至1:3.0である請求項6に記載のポリエステル樹脂の製造方法。
- 前記亜鉛系触媒は、合成される樹脂重量対比中心金属原子基準に1乃至100ppmの量で使用される請求項6に記載のポリエステル樹脂の製造方法。
- 前記エステル化反応は、0乃至10.0kg/cm2の圧力及び150乃至300℃の温度で行なわれる請求項6に記載のポリエステル樹脂の製造方法。
- 前記エステル化反応時間が600分以下である請求項6に記載のポリエステル樹脂の製造方法。
- 前記エステル化反応が200分乃至300分間行われる請求項6に記載のポリエステル樹脂の製造方法。
- 前記エステル化反応生成物を重縮合反応させる段階は、150乃至300℃の温度及び600乃至0.01mmHgの減圧条件で1乃至24時間行なわれる請求項6に記載のポリエステル樹脂の製造方法。
- 前記重縮合反応に、チタン系化合物、ゲルマニウム系化合物、アンチモン系化合物、アルミニウム系化合物、及びスズ系化合物からなる群より選択された1種以上の触媒化合物を追加的に添加する段階をさらに含む請求項6に記載のポリエステル樹脂の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020120056282A KR101995457B1 (ko) | 2012-05-25 | 2012-05-25 | 폴리에스테르 수지의 제조 방법 |
KR10-2012-0056282 | 2012-05-25 | ||
PCT/KR2013/004451 WO2013176467A1 (ko) | 2012-05-25 | 2013-05-21 | 폴리에스테르 수지의 제조 방법 |
Publications (2)
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JP2015517606A JP2015517606A (ja) | 2015-06-22 |
JP6371278B2 true JP6371278B2 (ja) | 2018-08-08 |
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JP2015513896A Active JP6371278B2 (ja) | 2012-05-25 | 2013-05-21 | ポリエステル樹脂の製造方法 |
Country Status (9)
Country | Link |
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US (1) | US9284405B2 (ja) |
EP (1) | EP2857431B1 (ja) |
JP (1) | JP6371278B2 (ja) |
KR (1) | KR101995457B1 (ja) |
CN (1) | CN104302688A (ja) |
ES (1) | ES2755824T3 (ja) |
HK (1) | HK1206373A1 (ja) |
TW (1) | TWI618730B (ja) |
WO (1) | WO2013176467A1 (ja) |
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KR101969004B1 (ko) * | 2012-06-05 | 2019-04-15 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 및 이의 제조 방법 |
JP2015147830A (ja) * | 2014-02-05 | 2015-08-20 | 帝人株式会社 | 全脂環族ポリエステルおよびその製造方法 |
JP6342673B2 (ja) * | 2014-02-26 | 2018-06-13 | 帝人株式会社 | ポリエステル組成物およびその製造方法 |
KR102119445B1 (ko) * | 2014-10-31 | 2020-06-16 | 에스케이케미칼 주식회사 | 오버헤드콘솔용 내화학성 고분자 수지 조성물 |
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2012
- 2012-05-25 KR KR1020120056282A patent/KR101995457B1/ko active IP Right Grant
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2013
- 2013-05-21 EP EP13793953.4A patent/EP2857431B1/en active Active
- 2013-05-21 ES ES13793953T patent/ES2755824T3/es active Active
- 2013-05-21 WO PCT/KR2013/004451 patent/WO2013176467A1/ko active Application Filing
- 2013-05-21 JP JP2015513896A patent/JP6371278B2/ja active Active
- 2013-05-21 US US14/403,639 patent/US9284405B2/en active Active
- 2013-05-21 CN CN201380025902.4A patent/CN104302688A/zh active Pending
- 2013-05-24 TW TW102118343A patent/TWI618730B/zh active
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Publication number | Publication date |
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CN104302688A (zh) | 2015-01-21 |
WO2013176467A1 (ko) | 2013-11-28 |
KR20130132138A (ko) | 2013-12-04 |
ES2755824T3 (es) | 2020-04-23 |
KR101995457B1 (ko) | 2019-07-02 |
US20150141612A1 (en) | 2015-05-21 |
EP2857431A1 (en) | 2015-04-08 |
TWI618730B (zh) | 2018-03-21 |
EP2857431A4 (en) | 2016-02-10 |
JP2015517606A (ja) | 2015-06-22 |
TW201406816A (zh) | 2014-02-16 |
EP2857431B1 (en) | 2019-08-28 |
US9284405B2 (en) | 2016-03-15 |
HK1206373A1 (en) | 2016-01-08 |
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