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Polyester Polyol, Polyurethane Resin, and Production Processes Therefor

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Polyester Polyol, Polyurethane Resin, and Production Processes Therefor (19) TZZ¥¥Z _T (11) EP 3 305 828 A1 (12) EUROPEAN PATENT APPLICATION published in accordance with Art. 153(4) EPC (43) Date of publication: (51) Int Cl.: 11.04.2018 Bulletin 2018/15 C08G 63/78 (2006.01) C08G 18/42 (2006.01) C08G 63/16 (2006.01) (21) Application number: 16878920.4 (86) International application number: (22) Date of filing: 22.12.2016 PCT/JP2016/088403 (87) International publication number: WO 2017/111033 (29.06.2017 Gazette 2017/26) (84) Designated Contracting States: • NITTA, Shigeki AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Tokyo 100-8251 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • YANO, Kaori PL PT RO RS SE SI SK SM TR Tokyo 1008251 (JP) Designated Extension States: • AOSHIMA, Takayuki BA ME Tokyo 1008251 (JP) Designated Validation States: • HIOKI, Yuta MA MD Tokyo 1008251 (JP) (30) Priority: 24.12.2015 JP 2015252151 (74) Representative: Vossius & Partner Patentanwälte Rechtsanwälte mbB (71) Applicant: Mitsubishi Chemical Corporation Siebertstrasse 3 Tokyo 100-8251 (JP) 81675 München (DE) (72) Inventors: • KANAMORI, Yoshikazu Tokyo 1008251 (JP) (54) POLYESTER POLYOL, POLYURETHANE RESIN, AND PRODUCTION PROCESSES THEREFOR (57) The present invention aims to provide a polyes- with a polyester polyol in which an aliphatic diol contains ter polyol having favorable reactivity and a favorable color as a structural unit 1,10-decanediol derived from a bio- tone, which can be used for obtaining a polyurethane mass resource, and in which the aldehyde body content having an excellent balance of flexibility, mechanical in the polyester polyol is 0.01 to 0.5% by weight, and a strength, and chemical resistance, and a method for pro- method for producing the polyester polyol. ducing the polyester polyol. The object can be achieved EP 3 305 828 A1 Printed by Jouve, 75001 PARIS (FR) EP 3 305 828 A1 Description TECHNICAL FIELD 5 [0001] The present invention relates to a method for producing a polyester polyol, which is used as a material for polyurethane resins and the like; a polyurethane resin using the polyester polyol; and methods for producing them. BACKGROUND ART 10 [0002] Polyols represented by polyester polyol and polyether polyol produce polyurethane resins by reaction with isocyanate. Polyols constitute the soft segment portions in polyurethane resins, and largely contribute to physical prop- erties of the polyurethane resins such as mechanical properties and durability. Since polyester polyol gives better physical properties to polyurethane resins in terms of mechanical strength and weatherability than other polyols, polyester polyol is widely used for polyurethane resins to be used as materials for synthetic/artificial leathers, plastic foams for shoe 15 soles, thermoplastic resins, paints, adhesives, and the like. [0003] Moreover, in recent years, global environmental issues have been attracting attention, and providing of materials that are conscious of the global environment is demanded. Also for polyurethane resins, use of materials derived from biomass resources such as plants instead of petroleum-derived materials is becoming popular. [0004] In terms of biomass resources from which polyester polyols are derived, there are, for example, cases where 20 biomass-derived succinic acid or castor-oil-derived sebacic acid is used as a material dicarboxylic acid, and cases where 1,3-propanediol obtained by a fermentation method or 1,10-decanediol derived from castor oil is used as a material diol. (Patent Documents 1, 2, 3, and 4) [0005] On the other hand, unlike materials prepared from petroleum, most of the materials derived from biomass resources require a high-level purification process for increasing their purity since they contain a large amount of impu- 25 rities. This often prevents their wide application as materials. The same applies to materials of polyester polyol. Materials which can be easily obtained without high-level purification and which give favorable physical properties to polyurethane resins are demanded. PRIOR ART DOCUMENTS 30 PATENT DOCUMENTS [0006] 35 Patent Document 1: WO 2011/125720 Patent Document 2: JP 2014-37552 A Patent Document 3: JP 2014-141548 A Patent Document 4: JP 2012-97189 A 40 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION [0007] None of these conventional techniques, that is, none of the techniques exemplified by Patent Documents 1 to 45 4, in production of a polyester polyol on, paid attention to the influence of compounds that are made to coexist with the material aliphatic diol on the efficiency of production of the polyester polyol, or the effect of the compounds on the reactivity and physical properties in production of a polyurethane resin using the polyester polyol as a material,. Moreover, production of a polyester polyol using a diol derived from a biomass resource as a material, and industrial production and use of its polyurethane, have not been useful from the viewpoint of the cost and the quality. 50 [0008] The present invention was made in view of the above problems that could not been solved by these conventional techniques. Thus, an object of the present invention is to provide a method for producing a polyester polyol containing an aliphatic diol derived from a biomass resource, wherein the produced polyester polyol shows favorable reactivity in polymerization and has a favorable color tone, and to provide a polyester polyol containing as a structural unit an aliphatic diol derived from a biomass resource, wherein the polyester polyol shows favorable reactivity upon urethane polymer- 55 ization, and wherein the obtained polyurethane has an excellent color tone and an excellent balance of physical properties including flexibility, mechanical strength, chemical resistance, and hot-water resistance. 2 EP 3 305 828 A1 MEANS FOR SOLVING THE PROBLEMS [0009] The present inventors intensively studied to solve the problems described above, and, as a result, discovered that, by use of a polyester polyol which contains a particular aliphatic diol unit and in which the aldehyde body content 5 in the polyester polyol is 0.01 to 0.5% by weight, a polyurethane having a favorable color tone and an excellent balance of flexibility, mechanical strength, chemical resistance, and hot-water resistance can be obtained, thereby reaching the present invention. The present inventors also discovered that, by producing a polyester polyol by polycondensing a dicarboxylic acid with a biomass-resource-derived aliphatic diol containing 0.01 to 1% by weight aldehyde body, poly- condensation of the polyester polyol can be carried out with favorable reactivity, and a polyurethane having an excellent 10 balance of flexibility, mechanical strength, chemical resistance, and hot-water resistance can be obtained from the polyester polyol, thereby reaching the present invention. [0010] The present invention was achieved based on such discoveries, and can be summarized as follows. [1] A polyester polyol comprising a structural unit derived from a dicarboxylic acid and a structural unit derived from 15 an aliphatic diol, wherein a structural unit derived from 1,10-decanediol is contained as the aliphatic diol unit; the polyester polyol has a number average molecular weight of 250 to 5000; and the polyester polyol contains 0.01 to 0.5% by weight aldehyde body. 20 [2] The polyester polyol according to [1], wherein the dicarboxylic acid contains a dicarboxylic acid derived from a biomass resource. [3] The polyester polyol according to [2], wherein the dicarboxylic acid contains succinic acid derived from a biomass resource. 25 [4] A polyurethane resin obtained by reacting the polyester polyol according to any one of [1] to [3] with one or more kinds of polyisocyanate and a chain extender. [5] A method for producing a polyurethane resin, comprising a step of reacting the polyester polyol according to any one of [1] to [3] with one or more kinds of polyisocyanate. [6] The method for producing a polyester polyol according to any one of [1] to [3], comprising a step of polycondensing 30 at least a dicarboxylic acid and an aliphatic diol, wherein the aliphatic diol contains 1,10-decanediol; and the aldehyde body content in the polyester polyol is 0.01 to 0.5% by weight. 35 EFFECT OF THE INVENTION [0011] By the present invention, a polyester polyol having favorable reactivity and a favorable color tone can be obtained. A polyurethane produced using the polyester polyol is characterized in that a favorable reactivity can be obtained in the urethane polymerization, and that the balance among the flexibility, mechanical strength, chemical 40 resistance, and hot-water resistance is excellent, so that the polyurethane is suitable for uses in elastic fibers, synthetic or artificial leathers, paints, and high-performance elastomers, and is therefore industrially very useful. MODE FOR CARRYING OUT THE INVENTION 45 [0012] Modes of the present invention are described below in detail. However, the present invention is not limited to the following embodiments, and may be carried out with a variety of modifications within the scope of the invention. [0013] Here, in the present description, the term "% by mass" has the same meaning as the term "% by weight"; the term "ppm by mass" has the same meaning as the term "ppm by weight"; and the term "part by mass" has the same meaning as the term "part by weight". When the simple term "ppm" is used, it means "ppm by weight". 50 [1. Polyester Polyol] [0014] The polyester polyol as an embodiment of the present invention is a polyester polyol which contains a structural unit derived from a dicarboxylic acid and a structural unit derived from an aliphatic diol, and which is typically produced 55 by polycondensation of a dicarboxylic acid with an aliphatic diol including 1,10-decanediol. 3 EP 3 305 828 A1 <Dicarboxylic Acid> [0015] Examples of the dicarboxylic acid used in the present invention (which includes dicarboxylic acids as well as their derivatives such as their esters) include aliphatic dicarboxylic acids, aliphatic dicarboxylic acid derivatives, aromatic 5 dicarboxylic acids, and aromatic dicarboxylic acid derivatives.
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