JP5834050B2 - 中間分子量ポリエステルと高分子量ポリエステルの製造方法 - Google Patents
中間分子量ポリエステルと高分子量ポリエステルの製造方法 Download PDFInfo
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- JP5834050B2 JP5834050B2 JP2013142533A JP2013142533A JP5834050B2 JP 5834050 B2 JP5834050 B2 JP 5834050B2 JP 2013142533 A JP2013142533 A JP 2013142533A JP 2013142533 A JP2013142533 A JP 2013142533A JP 5834050 B2 JP5834050 B2 JP 5834050B2
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- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
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- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000000196 viscometry Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Images
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
- C08G63/81—Preparation processes using solvents
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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)
- Polyesters Or Polycarbonates (AREA)
Description
[0014]特に明記しない限り、下記の用語は、下記に説明する意味を有するものとし、単数形と複数形に適用可能であるとする。
[0017]“高温(elevated temperature)”とは、少なくとも120℃の温度を意味している。
[0019]ポリマーに関して使用される場合、“低分子量”とは、Mnが4,000amu未満であるポリマーを意味し、“中間分子量”とは、Mnが4,000〜7,000amuであるポリマーを意味し、“高分子量”とは、Mnが7,000amuより大きいポリマーを意味している。
[0022]“重縮合温度”とは、200℃以上の温度を意味している。
[0024]“ポリエステルシロップ”とは、室温にて容易に注ぎ込むことができて、中間分子量または高分子量のポリエステルを非反応性キャリヤー中に含有する液体を意味している。
高分子量ポリエステル樹脂の製造
[0050]攪拌機、蒸留塔、凝縮器、温度計、および不活性ガス入口を装備した混合容器に、3.2モルの2−メチル−1,3−プロパンジオール、3.06モルの1,3−ベンゼンジカルボン酸、および0.8gのファストキャット(FASTCAT)(商標)4201ジブチル錫オキシド触媒(アルケマ社から市販)を仕込んだ。反応物は、ヒドロキシル:酸モル比が1.046:1であり、EGまたはPGを含有しなかった。反応器を不活性ガスでフラッシュ処理をし、水を除去しつつ4時間で235℃に加熱した。18〜25の酸価が達成されるまで〔アロマティック150フルイド(エクソンモービル社から市販)を加えてサンプルを希釈・冷却し、次いで0.1Nのメタノール性KOH溶液を使用してpH12の終点まで滴定することによって測定〕浴温度を235℃に保持した。さらなるサンプルにアロマティック150フルイドを加えて希釈・冷却し、OH基と過剰の無水物とを反応させて、無水物基を酸基に転化し、次いで0.1Nのメタノール性KOH溶液を使用してpH12の終点まで滴定することによって、バッチのヒドロキシル価を30分以内で測定した。反応温度を180℃に下げ、追加の1,3−ベンゼンジカルボン酸を加えて、ヒドロキシル:酸モル比を1.03:1に調整した。蒸留混合物中に17%の芳香族炭化水素と83%の不揮発性物質という反応器内容物が得られるよう、共沸蒸留と十分な量のアロマティック150フルイド(非反応性キャリヤーとして)を使用して重縮合反応を開始した。反応温度を235℃に上げ、反応容器圧を100KPa(15psi)に上昇させた。3.0未満の酸価が達成されるまで、バッチの温度を215℃に保持した。最終的な酸価は2.9であり、最終的なヒドロキシル価は8.0だった。ガードナースケールに基づいて測定した色は1であり、樹脂に曇りは認められなかった。生成物の数平均分子量は、ゲル透過クロマトグラフィーによる測定にてMn=9,087であった。
中間分子量ポリエステル樹脂の製造
[0051]攪拌機、蒸留塔、凝縮器、温度計、および不活性ガス入口を装備した混合容器に、3.2モルの2−メチル−1,3−プロパンジオール、3.06モルの1,3−ベンゼンジカルボン酸、および0.8gのファストキャット4201ジブチル錫オキシド触媒を仕込んだ。反応物は、ヒドロキシル:酸モル比が1.046:1であり、EGまたはPGを含有しなかった。反応器を不活性ガスでフラッシュ処理をし、水を除去しつつ4時間で235℃に加熱した。18〜25の酸価が達成されるまでバッチ温度を235℃に保持した。反応温度を180℃に下げ、追加の1,3−ベンゼンジカルボン酸を加えて、ヒドロキシル:酸モル比を1.04:1に調整した。蒸留混合物中に17%の芳香族炭化水素と83%の不揮発性物質という反応器内容物が得られるよう、共沸蒸留と十分な量のアロマティック150フルイドを使用して重縮合反応を開始した。反応温度を235℃に上げ、反応容器圧を100KPa(15psi)に上昇させた。3.0未満の酸価が達成されるまで、バッチの温度を215℃に保持し、目標分子数平均分子量の5,500amuを達成した。
Claims (6)
- 6,000〜20,000amuの数平均分子量と5〜20のヒドロキシル価を有する、中間分子量または高分子量のポリエステルシロップの製造方法であって、
a)エステルオリゴマーを供給もしくは作製すること;
b)水との共沸混合物を形成することができ、140℃よりも高い沸点を有する非反応性キャリヤー中にオリゴマーを含有する反応混合物を34kPa〜100kPaの圧力および200〜260℃の温度にて攪拌することによって、オリゴマーをポリエステルポリマーに転化させること;および
c)共沸還流により混合物から水を除去し、非反応性キャリヤー中の高分子量のポリエステルポリマーを含むシロップを得ること;を含む、
上記中間分子量または高分子量のポリエステルシロップの製造方法。 - 非反応性キャリヤーが、アルカン、芳香族炭化水素、石油系溶剤、植物由来溶剤、ケトン、またはこれらの混合物を含む、請求項1に記載の製造方法。
- 非反応性キャリヤーが最高300℃の沸点を有する、請求項1または2に記載の製造方法。
- 非反応性キャリヤーが、最終的なシロップの重量を基準として5%以上である、請求項1〜3のいずれかに記載の製造方法。
- ヒドロキシル:酸モル比またはヒドロキシル:エステルモル比が0.9:1〜1.1:1にてポリマーを形成することを含む、請求項1〜4のいずれかに記載の製造方法。
- エステルオリゴマーを非反応性キャリヤー中にて形成することを含む、請求項1〜5のいずれかに記載の製造方法。
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ITMI20121070A1 (it) * | 2012-06-19 | 2013-12-20 | Novamont Spa | Processo di preparazione di strutture oligomeriche complesse |
CN108528954B (zh) | 2012-08-09 | 2020-05-12 | Swimc有限公司 | 用于容器和其它物品的组合物以及使用相同组合物的方法 |
US10526506B2 (en) * | 2014-03-28 | 2020-01-07 | Swimc Llc | Polyester coating compositions containing polymers derived from cyclic carbonates |
BR112016021583B1 (pt) | 2014-04-14 | 2021-10-26 | Swimc Llc | Método para produzir um polímero de poliéter de alto peso molecular, e, recipiente de embalagem de alimento e bebida |
CA3109483A1 (en) | 2018-08-29 | 2020-03-05 | Swimc Llc | Medium or high molecular weight polyester powders, powder coating compositions, and processes of making powders |
CN116057037A (zh) * | 2020-06-08 | 2023-05-02 | 美凯艾贝有限责任公司 | 以多元醇和多元羧酸烷基酯的酯交换制备聚合物的方法、制备的聚合物和共聚物及其制品 |
CN111793151A (zh) * | 2020-07-15 | 2020-10-20 | 优卡化学(上海)有限公司 | 一种在线监测自由基聚合反应进程的方法 |
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2008
- 2008-02-06 US US12/027,233 patent/US9624342B2/en active Active
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- 2009-02-05 BR BRPI0908356A patent/BRPI0908356B8/pt active IP Right Grant
- 2009-02-05 JP JP2010545999A patent/JP2011511150A/ja active Pending
- 2009-02-05 WO PCT/US2009/033241 patent/WO2009100235A1/en active Application Filing
- 2009-02-05 EP EP09708559.1A patent/EP2249882B1/en active Active
- 2009-02-05 CA CA2715262A patent/CA2715262C/en active Active
- 2009-02-05 CN CN200980104434.3A patent/CN101939031B/zh active Active
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EP2249882A1 (en) | 2010-11-17 |
BRPI0908356B8 (pt) | 2021-06-22 |
JP2011511150A (ja) | 2011-04-07 |
MX2010008607A (es) | 2010-09-07 |
AU2009212386B2 (en) | 2014-08-28 |
EP2249882B1 (en) | 2017-01-18 |
CN101939031B (zh) | 2017-07-28 |
CN101939031A (zh) | 2011-01-05 |
JP2013231193A (ja) | 2013-11-14 |
US20090198005A1 (en) | 2009-08-06 |
CA2715262A1 (en) | 2009-08-13 |
WO2009100235A1 (en) | 2009-08-13 |
US9624342B2 (en) | 2017-04-18 |
US20170306086A1 (en) | 2017-10-26 |
AU2009212386A1 (en) | 2009-08-13 |
CA2715262C (en) | 2017-11-28 |
BRPI0908356B1 (pt) | 2019-02-26 |
MX336928B (es) | 2016-02-05 |
EP2249882A4 (en) | 2014-08-20 |
BRPI0908356A2 (pt) | 2015-07-28 |
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