JP4104150B2 - 多価アルコールのポリエステルポリオールの製造 - Google Patents
多価アルコールのポリエステルポリオールの製造 Download PDFInfo
- Publication number
- JP4104150B2 JP4104150B2 JP2004508152A JP2004508152A JP4104150B2 JP 4104150 B2 JP4104150 B2 JP 4104150B2 JP 2004508152 A JP2004508152 A JP 2004508152A JP 2004508152 A JP2004508152 A JP 2004508152A JP 4104150 B2 JP4104150 B2 JP 4104150B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formaldehyde
- polyhydric alcohol
- pentaerythritol
- trimethylolpropane
- 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.)
- Expired - Fee Related
Links
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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4219—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from aromatic dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
多価アルコールと少なくとも1種のジカルボン酸及び/又はジカルボン酸の誘導体(例、酸無水物)とを、任意に溶剤中で、反応水を除去しながら反応させて、ポリエステルポリオールを製造する方法であって、
多価アルコールとして、500ppm未満のホルムアルデヒドアセタール含有量を有するものを使用することを特徴とする製造方法
により達成されることを見いだした。
最終生成物が、強く着色することはほとんどなく、製造方法が異なってもその間に色数の変化は無く、そして生成物中の成分による曇り又はもやの発生を回避することができる。
で表される多価アルコールを挙げることができる。
で表されるアルデヒドをホルムアルデヒドと反応させ、その後アルデヒド基をヒドロキシル基に転化することにより得られるものである。
R3は、直鎖又は分岐のC1〜C10−アルキル(好ましくはC1〜C8−アルキル、さらに好ましくはC1〜C5−アルキル)、直鎖又は分岐のC1〜C10−ヒドロキシアルキル(好ましくはC1〜C8−ヒドロキシアルキル、さらに好ましくはC1〜C6−ヒドロキシアルキル)、又は水素であり、
nは、1〜4の整数(好ましくは1〜3の整数、さらに好ましくは1又は2)である。
ホルムアルデヒドアセタール含有量[質量%]=
((IVa)の質量%) × (30g/モル)/(146g/モル) +
((IVb(n=1))の質量%) × (30g/モル)/(178g/モル) +
((IVb(n=2))の質量%) × (2×30g/モル)/(208g/モル) +
((IVc)の質量%) × (30g/モル)/(280g/モル)
[実施例I]
加熱部、窒素バブラー、無秩序充填カラム及び蒸留装置を備えた実験用撹拌装置に、204.1gのオレイン酸、105.6gのアジピン酸、214.1gの無水フタル酸及び541.2gのTMP(ホルムアルデヒドアセタール含有量280ppm、ジホルマリン及びメタノール含有量0.4%)を、まず充填し、撹拌しながら170℃に加熱した。反応系から60.4gの水を除去した後、温度を220℃に上昇させた。形成する蒸留物の除去を続けながら、反応を酸価が0.5mgKOH/g未満になるまで行った。
実施例Iに従い、ホルムアルデヒドアセタール含有量620ppm及び1400ppmのTMPを用いて合成を繰り返した。
Claims (6)
- 少なくとも2個の酸基を有する少なくとも1種のカルボン酸および/または少なくとも1種のジカルボン酸の誘導体とトリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールとを、任意に触媒を添加して、反応水を除去しながら、モノまたはポリエステル化することによりトリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールのポリエステルポリオールを製造する方法であって、
トリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールとして、500ppm未満、かつ0ppm超過のホルムアルデヒドアセタール含有量を有するものを使用することを特徴とする製造方法。 - トリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールが製造後に、蒸留により精製され、次いで熱処理され、その後再び精製されている請求項1に記載の製造方法。
- 熱処理が100−300℃で行われる請求項2に記載の方法。
- 少なくとも2個の酸基を有するカルボン酸が、炭素原子数2−12個の脂肪族または芳香族ジカルボン酸である請求項1に記載の製造方法。
- 単官能性カルボン酸が、少なくとも2個の酸基を有するカルボン酸との混合物で使用される請求項1に記載の製造方法。
- 少なくとも1種の多官能性カルボン酸とのエステル化のために、500ppm未満、かつ0ppm超過のホルムアルデヒドアセタール含有量を有するトリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールを使用するトリメチロールプロパン、ネオペンチルグリコールまたはペンタエリトリトールのポリエステルポリオールの製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10223055A DE10223055A1 (de) | 2002-05-24 | 2002-05-24 | Verfahren zur Herstellung von Polyesterpolyolen mehrwertiger Alkohole |
PCT/EP2003/005307 WO2003099902A1 (de) | 2002-05-24 | 2003-05-21 | Verfahren zur herstellung von polyesterpolyolen mehrwertiger alkohole |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005530875A JP2005530875A (ja) | 2005-10-13 |
JP4104150B2 true JP4104150B2 (ja) | 2008-06-18 |
Family
ID=29432267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004508152A Expired - Fee Related JP4104150B2 (ja) | 2002-05-24 | 2003-05-21 | 多価アルコールのポリエステルポリオールの製造 |
Country Status (12)
Country | Link |
---|---|
US (1) | US7241914B2 (ja) |
EP (1) | EP1511787B1 (ja) |
JP (1) | JP4104150B2 (ja) |
KR (1) | KR100966870B1 (ja) |
CN (1) | CN1300211C (ja) |
AT (1) | ATE309286T1 (ja) |
AU (1) | AU2003232807A1 (ja) |
BR (1) | BR0311166B8 (ja) |
DE (2) | DE10223055A1 (ja) |
ES (1) | ES2250909T3 (ja) |
MX (1) | MXPA04011409A (ja) |
WO (1) | WO2003099902A1 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7531620B2 (en) | 2004-05-19 | 2009-05-12 | Her Majesty The Queen In Right Et Al. | Cross-linkable highly fluorinated poly(arylene ethers) for optical waveguide applications |
GB0423072D0 (en) | 2004-10-18 | 2004-11-17 | Ici Plc | Surfactant compounds |
EP2144576B1 (en) * | 2007-04-24 | 2014-06-18 | Covidien LP | Biodegradable macromers |
DE102011118953B4 (de) * | 2011-11-19 | 2014-06-05 | Oxea Gmbh | Destillatives Verfahren zur Gewinnung von Di-Trimethylolpropan |
KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
DK2820112T3 (en) * | 2012-02-28 | 2017-09-11 | Petroliam Nasional Berhad | PROCEDURE FOR PREPARING POLYOLS AND APPLICATIONS THEREOF |
KR102061376B1 (ko) | 2012-02-28 | 2019-12-31 | 페트롤리암 내셔널 버하드 (페트로나스) | 윤활제 조성물 및 이의 제조방법 |
MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
KR101514990B1 (ko) * | 2013-11-14 | 2015-04-29 | (주)이피아이 | 천연유래 단량체를 함유한 폴리에스테르 수지를 포함하는 분체 도료용 조성물의 제조방법 |
CN107987257B (zh) * | 2016-10-27 | 2020-01-31 | 万华化学集团股份有限公司 | 一种聚酯多元醇的制备方法 |
KR101900490B1 (ko) | 2017-09-27 | 2018-09-19 | (주)엔나노텍 | 탄화수소계 발포제와의 혼합성 및 난연성이 우수한 폴리에스터 폴리올의 제조방법 |
CN111187401B (zh) * | 2018-11-15 | 2021-05-25 | 中国科学院大连化学物理研究所 | 一种聚酯多元醇的制备方法 |
Family Cites Families (15)
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US3097245A (en) * | 1959-01-13 | 1963-07-09 | Trojan Powder Co | Process for the preparation of trimethylolalkane |
GB1218509A (en) | 1969-02-03 | 1971-01-06 | Wacker Chemie Gmbh | Process for the production of acetoacetic acid esters |
JPS509B1 (ja) | 1969-11-28 | 1975-01-06 | ||
CA1062848A (en) * | 1975-08-14 | 1979-09-18 | Union Camp Corporation | Coating compositions |
DE68917352D1 (de) | 1988-04-20 | 1994-09-15 | Kuraray Co | Trimethylolheptane und ihre Anwendung. |
US5525683A (en) * | 1994-11-22 | 1996-06-11 | Bayer Corporation | Ether-linked amine-terminated polyesters and a process for their production |
WO1997016401A1 (en) * | 1995-11-03 | 1997-05-09 | Union Carbide Chemicals & Plastics Technology Corporation | Reaction mixtures containing substituted hydrocarbon diols and processes for the preparation thereof |
DE19542036A1 (de) * | 1995-11-10 | 1997-05-15 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
ATE236109T1 (de) | 1995-11-30 | 2003-04-15 | Kyowa Yuka Kk | Verfahren zur herstellung von 1,5-pentandiol- derivaten |
DE19653093A1 (de) * | 1996-12-20 | 1998-06-25 | Basf Ag | Verfahren zur Herstellung von Polyalkoholen |
WO1998041578A1 (fr) | 1997-03-17 | 1998-09-24 | Kyowa Yuka Co., Ltd. | Composition de resine polyester, resine durcie et materiau de revetement |
CN1113073C (zh) | 1997-03-27 | 2003-07-02 | 协和油化株式会社 | 聚氨酯及聚酯多元醇 |
US6096905A (en) * | 1999-06-01 | 2000-08-01 | Celanese International Corporation | Treatment of a composition comprising a trimethylolalkane bis-monolinear formal |
DE19963435A1 (de) | 1999-12-28 | 2001-07-05 | Basf Ag | Verfahren zur Reinigung von durch Hydrierung hergestelltem Trimethylolpropan durch kontinuierliche Destillation |
DE10029055B4 (de) | 2000-06-13 | 2006-06-29 | Basf Ag | Verfahren zur Farbzahlverbesserung von mehrwertigen Alkoholen durch Tempern |
-
2002
- 2002-05-24 DE DE10223055A patent/DE10223055A1/de not_active Withdrawn
-
2003
- 2003-05-21 CN CNB03811853XA patent/CN1300211C/zh not_active Expired - Fee Related
- 2003-05-21 ES ES03755043T patent/ES2250909T3/es not_active Expired - Lifetime
- 2003-05-21 BR BRPI0311166-0A patent/BR0311166B8/pt not_active IP Right Cessation
- 2003-05-21 MX MXPA04011409A patent/MXPA04011409A/es active IP Right Grant
- 2003-05-21 JP JP2004508152A patent/JP4104150B2/ja not_active Expired - Fee Related
- 2003-05-21 DE DE50301629T patent/DE50301629D1/de not_active Expired - Lifetime
- 2003-05-21 AT AT03755043T patent/ATE309286T1/de not_active IP Right Cessation
- 2003-05-21 AU AU2003232807A patent/AU2003232807A1/en not_active Abandoned
- 2003-05-21 US US10/512,851 patent/US7241914B2/en not_active Expired - Fee Related
- 2003-05-21 WO PCT/EP2003/005307 patent/WO2003099902A1/de active IP Right Grant
- 2003-05-21 EP EP03755043A patent/EP1511787B1/de not_active Revoked
- 2003-05-21 KR KR1020047018906A patent/KR100966870B1/ko not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE10223055A1 (de) | 2003-12-11 |
CN1656140A (zh) | 2005-08-17 |
WO2003099902A1 (de) | 2003-12-04 |
JP2005530875A (ja) | 2005-10-13 |
BR0311166B8 (pt) | 2013-02-19 |
US20050203268A1 (en) | 2005-09-15 |
KR100966870B1 (ko) | 2010-06-29 |
BR0311166A (pt) | 2005-03-15 |
DE50301629D1 (de) | 2005-12-15 |
EP1511787A1 (de) | 2005-03-09 |
BR0311166B1 (pt) | 2013-01-08 |
KR20050004202A (ko) | 2005-01-12 |
CN1300211C (zh) | 2007-02-14 |
ATE309286T1 (de) | 2005-11-15 |
MXPA04011409A (es) | 2005-02-14 |
AU2003232807A1 (en) | 2003-12-12 |
EP1511787B1 (de) | 2005-11-09 |
US7241914B2 (en) | 2007-07-10 |
ES2250909T3 (es) | 2006-04-16 |
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