WO2006100756A1 - Procede de production d'un polyol de polyester - Google Patents

Procede de production d'un polyol de polyester Download PDF

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Publication number
WO2006100756A1
WO2006100756A1 PCT/JP2005/005151 JP2005005151W WO2006100756A1 WO 2006100756 A1 WO2006100756 A1 WO 2006100756A1 JP 2005005151 W JP2005005151 W JP 2005005151W WO 2006100756 A1 WO2006100756 A1 WO 2006100756A1
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WO
WIPO (PCT)
Prior art keywords
polyester polyol
reaction
polyol
component
producing
Prior art date
Application number
PCT/JP2005/005151
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English (en)
Japanese (ja)
Inventor
Yuujirou Ikejiri
Yuuichi Tsuchimochi
Original Assignee
Kawasaki Kasei Chemicals Ltd.
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 Kawasaki Kasei Chemicals Ltd. filed Critical Kawasaki Kasei Chemicals Ltd.
Priority to PCT/JP2005/005151 priority Critical patent/WO2006100756A1/fr
Publication of WO2006100756A1 publication Critical patent/WO2006100756A1/fr

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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
    • 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
    • C08G18/4213—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 terephthalic acid and dialcohols
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid

Definitions

  • the present invention relates to a method for producing a polyester polyol. More specifically, the present invention relates to a method for producing a polyester polyol suitably used for producing a rigid polyurethane foam and a polyester polyol produced by the method.
  • Rigid polyurethane foam generally has excellent heat insulation properties, and is therefore widely used as a member for building heat insulation walls in refrigerator rooms, refrigerators, freezer rooms, freezers, various buildings, and the like.
  • Rigid polyurethane foam generally contains a liquid composed of a polyisocyanate component (hereinafter referred to as A liquid), a polyether polyol component, a polyester polyol component and a foaming agent, and, if necessary, a catalyst and a foam stabilizer.
  • a mixed liquid hereinafter referred to as “B liquid” is prepared, and A liquid and B liquid are mixed, and foamed and cured in a short time. For this reason, polyester polyols used in the production of rigid polyurethane foam must have low viscosity and excellent compatibility with foaming agents.
  • an aromatic polycarboxylic acid is used as a polycarboxylic acid component of a raw material for production.
  • a polyester polyol having high flame retardancy can be obtained.
  • the flame retardancy is further improved by replacing part or all with terephthalic acid.
  • polyester polyol when terephthalic acid is used as the polycarboxylic acid component, the polyester polyol becomes more cloudy as time passes than when phthalic anhydride or the like is used. It becomes a problem that the part produces crystal i). The higher the ratio of terephthalic acid, the more pronounced this tendency toward cloudiness. Specifically, of the raw material polycarboxylic acid, no turbidity is produced when terephthalic acid is not used, whereas when about 50% by weight of terephthalic acid is used, white turbidity and terephthalic acid are removed in about 3 months. In the case of 100%, it becomes cloudy in about one month or in a shorter period.
  • the ratio of terephthalic acid can be increased to further improve the flame retardancy of the rigid polyurethane foam.
  • a method for preventing this clouding a method using triethylene glycol or triethylene glycol by-product bottom as a part of the reaction raw material has been proposed. When the compatibility of the resulting polyester polyol with the blowing agent is low, problems remain.
  • HCFC-141b with a small coefficient is mainly used. However, the use of this HCFC-141b may also be limited in the future because the ozone depletion potential is not zero.
  • HFC_245fa, HFC_365mfc, pentane, cyclopentane, etc. are assumed.
  • low compatibility with the polyester polyol component is a big problem. If this compatibility is improved, liquid B with uniform stability can be obtained, and the degree of freedom of liquid B formulation can be improved, such as the types of polyether polyol components and polyester polyol components, and their mixing ratios.
  • the addition of surfactants, particularly nonionic surfactants, is widely performed, but the effect cannot be said to be sufficient.
  • Patent Document 1 JP-A-11-60918
  • Patent Document 2 JP 2000-17058 A
  • the present inventor has solved the problem of white turbidity that occurs when terephthalic acid is used as a raw material polycarboxylic acid component, is excellent in compatibility with a foaming agent having high flame retardancy, and has a low viscosity.
  • the object of the present invention is as follows.
  • a polyester polyol when a polyester polyol is produced by reacting a polycarboxylic acid component containing terephthalic acid with a polyol component, triethylene glycol and a part of the polyol component are used.
  • a method for producing a polyester polyol characterized by using polypropylene glycol and a polyester polyol produced by the production method are provided.
  • a polyester polyol when a polyester polyol is produced by reacting a polycarboxylic acid component containing terephthalic acid with a polyol component, triethylene is used as a part of the polyol component.
  • glycol and polypropylene glycol the problem of white turbidity of products generated when terephthalic acid is used as a raw material polycarboxylic acid component is solved, and it is suitable for environments such as HFC_245fa, HFC_365mfc, pentane, and cyclopentane.
  • the problem of poor compatibility between the foaming agent and the main component of the B liquid, particularly the polyester polyol component is solved, and a polyester polyol that is suitably used for the production of rigid polyurethane foam is provided. .
  • a polyester polyol having good compatibility with a foaming agent is provided. Therefore, it has good uniform stability and is preferably used for producing a rigid polyurethane foam. This also leads to an improvement in the degree of freedom of the B liquid formulation, such as the types of polyether polyol components and polyester polyol components, and the mixing ratio thereof.
  • the ratio of terephthalic acid having a large effect of imparting flame retardancy can be increased to further increase the flame retardancy of the product.
  • a polyester polyol that is suitably used for producing a rigid polyurethane foam can be advantageously produced industrially.
  • the polyester polyol obtained by the method of the present invention is a polyester polyol obtained by a reaction between a polycarboxylic acid component and a polyol component, and is preferably a polyester polyol used for producing a rigid polyurethane foam.
  • terephthalic acid is used as the polycarboxylic acid component which is a raw material for producing the polyester polyol.
  • aromatic dicarboxylic acids other than terephthalic acid or aromatic tricarboxylic acids can be used.
  • Suitable aromatic polycarboxylic acid components include phthalic acid, trimellitic acid, or acid anhydrides thereof. Further, these aromatic polycarboxylic acids may be mixed with a slight amount of an aliphatic polycarboxylic acid such as succinic acid, maleic acid or adipic acid.
  • phthalic acid or phthalic anhydride is particularly preferred.
  • the total amount of polycarboxylic acid which is preferably 40% by weight or more, may be used as the terephthalic acid in the polycarboxylic acid component.
  • triethylene glycol and polypropylene glycol are used as a part of the polyol component that is a raw material for producing the polyester polyol.
  • the amount of triethylene glycol used is 10-60% by weight of the total polyol component.
  • the amount of triethylene glycol is less than 10% by weight of the total polyol component, the effect of preventing white turbidity is hardly observed. On the other hand, if it exceeds 60% by weight, adverse effects such as a significant increase in reaction time may occur.
  • the preferred amount of triethylene glycol is 20-50% by weight.
  • the polypropylene glycol preferably has a number average molecular weight of 200 to 3,000.
  • polypropylene glycol having a number average molecular weight of 300 2,000 is most preferable, and polypropylene glycol having a number average molecular weight of 400 to 1,000 is most preferable.
  • These polypropylene glycols may be used alone or as a mixture, and the mixing ratio is not particularly limited.
  • Polypropylene glycol is industrially produced by the ring-opening polymerization of propylene oxide. The power obtained as a bifunctional alcohol having various molecular weight distributions. Depending on the molecular weight distribution and production method, propylene glycol monomers and oligomers are included. May be.
  • the amount of the polypropylene glycol is of the entire polyol component 10 40 weight 0/0 preferably les. Amount of polypropylene glycol used Less than 10% by weight of the polyol component is less effective in improving compatibility with the foaming agent and lowering the viscosity. On the other hand, if it exceeds 40% by weight, it is difficult to produce flame retardant when producing rigid polyurethane foam. There is a tendency for the deterioration of properties and foam strength to be adversely affected. With regard to the amount used above, the amount of triethylene glycol used is not 60% by weight and the amount of polypropylene glycol used is 40% by weight.
  • the effects of the present invention such as white turbidity prevention can be obtained.
  • a polyol component other than triethylene glycol and polypropylene glycol Ye A remarkable effect can be obtained when using lenglycol.
  • other polyols may be used as long as the effects of the present invention are not impaired. Examples thereof include diols and triols such as ethylene glycolate, glycerin and trimethylolpropane.
  • the target polyester polyol can be produced by reacting the polycarboxylic acid component and the polyol component in the presence of a catalyst, usually at 150 to 230 ° C.
  • the pressure at the time of reacting the above components may be normal pressure, but it is preferable to gradually reduce the pressure as the reaction proceeds in order to remove by-product water out of the system and complete the reaction quickly. .
  • the space of the reaction vessel with nitrogen gas and further remove the dissolved oxygen in the reaction solution in order to prevent coloring of the produced polyester polyol.
  • an acid catalyst is generally used.
  • the power of which tetraisopropyl titanate, a norelic acid, is suitable may be a Bronsted acid, such as paratoluenesulfonic acid.
  • the polyester polyol obtained by the production method according to the present invention is suitable for the production of rigid polyurethane foam.
  • Rigid polyurethane foam is produced by a method of foaming and curing in a short time by mixing a polyisocyanate component, a polyether polyol component, a polyester polyol component and foaming IJ, and if necessary, a catalyst and a foam stabilizer. Can be manufactured.
  • the polyisocyanate component is not particularly limited as long as it is an organic compound having two or more isocyanate groups in one molecule.
  • an aliphatic polyisocyanate, an alicyclic polyisocyanate, and an aromatic polyisocyanate, or a modification thereof may be mentioned.
  • aromatic polyisocyanates or modified products thereof are exemplified, and examples thereof include diphenylmethane diisocyanate, polymeric dimethanemethane diisocyanate, and carbodiimide modification thereof. Such as things.
  • polyether polyol component examples include alkylene oxide polymers, sugar polymers, modified amines thereof, reaction products of polyamines and alkylene oxides, and the like.
  • the polyether polyol component is easily available because it is commercially available in many varieties, and these commercially available products can be used alone or as a mixture.
  • polyester polyol component a polyester polyol produced by the above method is used.
  • the foaming agent for example, a fluorocarbon foaming agent such as HCFC_141b, HFC-245fa, and HFC-365mfc can be used. These blowing agents can be used alone or in combination.
  • a catalyst that can be used in the production of the rigid polyurethane foam a known catalyst that is used in the production of a normal urethane foam can be used without any limitation. Examples thereof include amine catalysts such as triethylamine and N, N-dimethylhexylamine.
  • amine catalysts such as triethylamine and N, N-dimethylhexylamine.
  • foam stabilizer that can be used in the production of the rigid polyurethane foam a nonionic surfactant, an anionic surfactant, or a cationic surfactant can be used. Of these, nonionic surfactants are preferred, and silicone surfactants are particularly preferred.
  • the pressure in the reactor was maintained at 13.3 kPa at a reduced pressure with respect to normal pressure from the time when the internal temperature reached 180 ° C until the internal temperature reached 200 ° C. Thereafter, the pressure was gradually reduced over 4 hours, and the pressure was reduced to 18.3 kPa with respect to normal pressure. This pressure was maintained until the reaction was completed. It was visually observed that the reaction mixture became a homogeneous solution as the reaction proceeded. While the reaction was in progress, a part of the reaction mixture was withdrawn from the reactor, and the acid value was measured for the sample withdrawn as an indicator for confirming the progress of the reaction. The acid value was measured according to JIS K1557 1970. At the end of the reaction, the acid value is 3 or less and the reaction mixture is The reaction time was defined as the time when the homogeneous solution was formed and the time required from the time when the catalyst was added to the reaction vessel to the end of the reaction.
  • the reaction product was extracted, and the viscosity of the extracted sample was measured. Further, the obtained solubility was measured as an index of the compatibility between the polyester polyol and the foaming agent.
  • the viscosity was measured at 25 ° C using a rotational viscometer (B-type viscometer).
  • the solubility of the foaming agent in the polyester polyol is determined by gradually adding a foaming agent (HF C_245fa, HFC_365mfc, cyclopentane, etc.) to a predetermined amount of polyester polyol in a release system at room temperature and atmospheric pressure, and forming a visually transparent uniform phase. The maximum amount that could be formed was measured and taken as solubility.
  • a foaming agent HF C_245fa, HFC_365mfc, cyclopentane, etc.
  • the charged components were 67 g of phthalic anhydride, 299 g of terephthalic acid, 296 g of diethylene glycol, utylene, 28 g of linole, 105 g of linolec, 105 g of linole and polypropylene glycol. (Number average molecular weight 400)
  • the reaction was carried out in the same procedure as in the same example except that it was changed to 279 g. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 62 g of phthalic anhydride, 279 g of terephthalic acid, 179 g of diethylene glycol, 186 g of ethylene, 26 g of linole, 253 g of triethylene, and polypropylene glycol (several
  • the reaction was carried out in the same procedure as in the same example except that the average molecular weight was changed to 269 g. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 57 g of phthalic anhydride, 25 6 g of terephthalic acid, 53 g of diethylene glycol, 24 g of ethylene glycol, 41 lg of triethylene glycol and 262 g of polypropylene glycol (number average molecular weight 400). Except for the change, the reaction was carried out in the same procedure as in this example. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed. The reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • Example 1 In the example described in Example 1, except that the charged components were changed to 70 g of phthalic anhydride, 31.5 g of terephthalic acid, 377 g of diethylene glycol, 29 g of ethylene glycol, and 285 g of polypropylene glycol (number average molecular weight 400).
  • the reaction was performed in the same manner as in. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the reaction product was confirmed to be complete by measuring the acid value, and the reaction was completed.
  • the reaction product was evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 76 g of phthalic anhydride, 34 l g of terephthalic acid, 220 g of diethylene glycol, ethylene g, 32 g of linole, 312 g of triethylene c, 312 g of linole and polypropylene glycol ( Number average molecular weight 400)
  • the reaction was carried out in the same procedure as in the same example except that it was changed to 103 g. Visual observation that the reaction mixture was homogenized At the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 72 g of phthalic anhydride, 324 g of terephthalic acid, 210 g of diethylene glycol, 30 g of ethylene, 30 g of linole, 297 g of linolec, polypropylene glycol (several
  • the reaction was carried out in the same procedure as in the same example except that the average molecular weight was changed to 400) 146 g. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 69 g of phthalic anhydride, 30 9 g of terephthalic acid, 200 g of diethylene glycol, 29 g of ethylene, 29 g of linole, 283 g of triethylene, 283 g of linole and polypropylene glycol (several The reaction was carried out in the same procedure as in the same example except that the average molecular weight was 400) 186 g. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed. The reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charged components were 66 g of phthalic anhydride, 297 g of terephthalic acid, 190 g of diethylene glycol, ethylene g, 28 g of linole, 268 g of triethylene c, 268 g of linole and polypropylene glycol (several
  • the reaction was carried out in the same procedure as in the same example except that the average molecular weight was 400). It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • the charging components were 63 g of phthalic anhydride, 284 g of terephthalic acid, 182 g of diethylene glycol, 182 g of ethylene, 27 g of linoleic acid, 257 g of triethylene glycol, polypropylene glycol (several
  • the reaction was carried out in the same procedure as in the same example except that the average molecular weight was 400) 257 g. It was confirmed by visual observation that the reaction mixture was homogenized, and at the same time, the completion of the reaction was confirmed by measuring the acid value of the reaction product, and the reaction was completed.
  • the reaction products were evaluated in the same manner as in Example 1, and the results are shown in Table 1.
  • Example 1 in which triethylene glycol was used in the range of 1060% by weight of the total polyol component in producing a polyester polyol by reacting a polycarboxylic acid component containing terephthalic acid with a polyol component.
  • Example 5 there is no cloudiness for 3 months in both the registration and the deviation.
  • each of the raw material compositions corresponding to each of the example 1 and example 5 is within 3 months. Cloudiness is observed.
  • the present invention has particularly advantageous effects as described in detail above, and the polyester polyol obtained according to the present invention can be suitably used for the production of rigid polyurethane, and its industrial utility value is extremely large. is there.

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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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Le problème à résoudre dans le cadre de l’invention est celui du trouble causé dans un produit lorsque l’acide téréphtalique est utilisé comme composé acide carboxylique de départ dans un procédé de production d’un polyol de polyester. La solution proposée consiste en un procédé présentant des avantages sur le plan industriel qui permet de produire un polyol de polyester ayant une compatibilité excellente avec un agent moussant et une faible viscosité, et faisant preuve d'un excellent caractère ignifuge lorsqu'il est formé en une mousse polyuréthane rigide. Lorsque le polyol de polyester est produit en faisant réagir des composants acide polycarboxylique contenant de l’acide téréphtalique et des composés polyols, le triéthylène glycol et le polypropylène glycol sont utilisés en tant que composés polyols. Il est particulièrement préférable d’utiliser, en tant que composés polyols, du triéthylène glycol et du polypropylène glycol, à hauteur respectivement de 10 à 60 % en poids et 10 à 40 % en poids de la totalité des composés polyol de départ.
PCT/JP2005/005151 2005-03-22 2005-03-22 Procede de production d'un polyol de polyester WO2006100756A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160119838A (ko) * 2014-02-11 2016-10-14 바스프 에스이 폴리우레탄 강성 폼 및 폴리이소시아누레이트 강성 폼의 제조 방법
JP2016536374A (ja) * 2013-09-30 2016-11-24 ダウ グローバル テクノロジーズ エルエルシー ポリエステルポリオール及びポリオール混和物、ならびに硬質ポリウレタンフォームの製造

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000017058A (ja) * 1998-07-04 2000-01-18 Hokoku Seiyu Kk ポリウレタン用ポリオール
JP2005075911A (ja) * 2003-08-29 2005-03-24 Kawasaki Kasei Chem Ltd ポリエステルポリオールの製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000017058A (ja) * 1998-07-04 2000-01-18 Hokoku Seiyu Kk ポリウレタン用ポリオール
JP2005075911A (ja) * 2003-08-29 2005-03-24 Kawasaki Kasei Chem Ltd ポリエステルポリオールの製造方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016536374A (ja) * 2013-09-30 2016-11-24 ダウ グローバル テクノロジーズ エルエルシー ポリエステルポリオール及びポリオール混和物、ならびに硬質ポリウレタンフォームの製造
KR20160119838A (ko) * 2014-02-11 2016-10-14 바스프 에스이 폴리우레탄 강성 폼 및 폴리이소시아누레이트 강성 폼의 제조 방법
JP2017509738A (ja) * 2014-02-11 2017-04-06 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ ポリウレタン硬質フォーム及びポリイソシアヌレート硬質フォームの製造方法
KR102338624B1 (ko) 2014-02-11 2021-12-14 바스프 에스이 폴리우레탄 강성 폼 및 폴리이소시아누레이트 강성 폼의 제조 방법

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