EP-4735506-A1 - POLYESTER POLYOL, POLYURETHANE FOAM USING THE SAME AND METHOD FOR PRODUCING POLYESTER POLYOL

Abstract

An object of the present invention is to provide a biomass-derived polyester polyol that has a high compatibility with a variety of foaming agents, and can be used to produce a polyurethane foam in which a reduction in compressive strength is reduced.　The present invention relates to a polyester polyol for a polyurethane foam, wherein the polyester polyol comprises a polyester polyol that is a reaction product of raw-material compounds containing:　 a rosin (a) containing a resin acid (a1) having a conjugated double bond;　 a biomass-derived fatty acid (b) containing an unsaturated fatty acid (b1);　 an α,β-unsaturated carboxylic acid (c); and　 a polyol (d) containing a diol (d1) having an ether bond.

Inventors

• HUFENDIEK, Andrea
• RAMOS, Eva

Assignees

• Lawter, Inc.

Dates

Publication Date

20260506

Application Date

20240614

Claims (10)

1. A polyester polyol for a polyurethane foam, the polyester polyol comprising a polyester polyol that is a reaction product of raw-material compounds containing: a rosin (a) containing a resin acid (a1) having a conjugated double bond; a biomass-derived fatty acid (b) containing an unsaturated fatty acid (b1); an α,β-unsaturated carboxylic acid (c); and a polyol (d) containing a diol (d1) having an ether bond.
2. The polyester polyol according to claim 1, wherein a weight ratio [(a)/(b)] of the rosin (a) to the biomass-derived fatty acid (b) in the raw-material compounds is 0.13 or more and 2.00 or less.
3. The polyester polyol according to claim 1, wherein a weight ratio [(c)/(a)] of the α,β-unsaturated carboxylic acid (c) to the rosin (a) in the raw-material compounds is 0.15 or more and 2.00 or less.
4. The polyester polyol according to claim 1, wherein a weight ratio [(c)/(a+b)] of the α,β-unsaturated carboxylic acid (c) to the total amount of the rosin (a) and the biomass-derived fatty acid (b) in the raw-material compounds is 0.05 or more and 0.45 or less.
5. The polyester polyol according to claim 1, wherein a weight ratio [(d1)/(a+b)] of the diol (d1) having an ether bond to the total amount of the rosin (a) and the biomass-derived fatty acid (b) in the raw-material compounds is 0.30 or more and 2.00 or less.
6. The polyester polyol according to claim 1, wherein the raw-material compounds further contain an aromatic polycarboxylic acid (e).
7. The polyester polyol according to claim 6, wherein a weight ratio [(e)/(a+b)] of the aromatic polycarboxylic acid (e) to the total amount of the rosin (a) and the biomass-derived fatty acid (b) in the raw-material compounds is 0.05 or more and 0.35 or less.
8. A polyurethane foam, being a foam of a foamable composition containing a polyol (P), a polyisocyanate (I), and a foaming agent, wherein the polyol (P) comprises the polyester polyol according to any one of claims 1 to 7.
9. A method for producing a polyester polyol for a polyurethane foam, comprising a step of obtaining the polyester polyol by reacting raw-material compounds containing: a rosin (a) containing a resin acid (a1) having a conjugated double bond; a biomass-derived fatty acid (b) containing an unsaturated fatty acid (b1); an α,β-unsaturated carboxylic acid (c); and a polyol (d) containing a diol (d1) having an ether bond.
10. The method for producing a polyester polyol for a polyurethane foam according to claim 9, comprising: a step of carrying out a Diels-Alder reaction or an ene reaction of the rosin (a) containing the resin acid (a1) having a conjugated double bond and the biomass-derived fatty acid (b) containing the unsaturated fatty acid (b1) with the α,β-unsaturated carboxylic acid (c) to obtain an adduct of the resin acid (a1) and the α,β-unsaturated carboxylic acid (c), and an adduct of the unsaturated fatty acid (b1) and the α,β-unsaturated carboxylic acid (c); and a step of carrying out an esterification reaction of the adduct of the resin acid (a1) and the α,β-unsaturated carboxylic acid (c) and the adduct of the unsaturated fatty acid (b1) and the α,β-unsaturated carboxylic acid (c) with the polyol (d) containing the diol (d1) having an ether bond to obtain the polyester polyol.

Description

POLYESTER POLYOL, POLYURETHANE FOAM USING THE SAME AND METHOD FOR PRODUCING POLYESTER POLYOL The present invention relates to a polyester polyol derived from biomass, a polyurethane foam produced using the same and a method for producing the polyester polyol. Conventionally, polyurethane foams have been used as a heat insulating material in various applications.　Examples of the applications include architecture members (a roof, a ceiling, and a wall of architecture, etc.), appliances (a refrigerator, a hot-water supply, etc.), vehicles (an automobile, an aircraft, a ship, etc.), pipes, and tanks. A polyurethane foam is produced by a reaction of a polyol with a polyisocyanate in the presence of a foaming agent.　As such a polyol, a polyester polyol is used.　For example, a polyester polyol is produced by dehydration condensation of a polybasic acid and a polyhydric alcohol.　A conventional polyester polyol is generally produced from raw materials derived from fossil resources, such as petroleum. Examples A1 to A6, Comparative Examples A1, A2 and A4 Comparative Example A3 Examples B1 to B7 and Comparative Examples B1 to B4 (Polyester polyol) 　　　 The present invention relates to a polyester polyol for a polyurethane foam.　The polyester polyol includes a polyester polyol that is a reaction product of raw material compounds containing: 　　　　　　　a rosin (a) containing a resin acid (a1) having a conjugated double bond; 　　　　　　　a biomass-derived fatty acid (b) containing an unsaturated fatty acid (b1); 　　　　　　　an α,β-unsaturated carboxylic acid (c); and 　　　　　　　a polyol (d) containing a diol (d1) having an ether bond. The polyester polyol for a polyurethane foam is preferably the polyester polyol that is a reaction product of raw material compounds containing: 　　　　　　　a rosin (a) containing a resin acid (a1) having a conjugated double bond; 　　　　　　　a biomass-derived fatty acid (b) containing an unsaturated fatty acid (b1); 　　　　　　　an α,β-unsaturated carboxylic acid (c); and 　　　　　　　a polyol (d) containing a diol (d1) having an ether bond. For the polyester polyol of the present invention, as raw materials derived from biomass, the rosin (a) containing the resin acid (a1) having a conjugated double bond, and the biomass-derived fatty acid (b) containing the unsaturated fatty acid (b1) are used.　To each of the rosin (a) and the biomass-derived fatty acid (b), the α,β-unsaturated carboxylic acid (c) is added by a Diels-Alder reaction or an ene reaction, to obtain a polybasic acid having a plurality of carboxy groups.　Further, the carboxy groups are esterified with a hydroxyl group of the polyol (d), to obtain a polyester polyol. As described above, the use of the rosin (a) modified by the α,β-unsaturated carboxylic acid (c) can reduce a reduction in compressive strength of a polyurethane foam.　However, the single use of the rosin (a) modified by the α,β-unsaturated carboxylic acid (c) may reduce the compatibility of the polyester polyol with a foaming agent.　As a countermeasure for this, the biomass-derived fatty acid (b) modified by the α,β-unsaturated carboxylic acid (c) is used to enhance the compatibility of the polyester polyol with a foaming agent. Therefore, the rosin (a) modified by the α,β-unsaturated carboxylic acid (c) is used in combination with the biomass-derived fatty acid (b) modified by the α,β-unsaturated carboxylic acid (c).　Thus, a polyester polyol that has a high compatibility with a variety of foaming agents and can be used to produce a polyurethane foam in which a reduction in compressive strength is reduced, despite the use of a biomass raw material, can be provided. In the present invention, "biomass" means an organic resource derived from an organism or a plant except for resources derived from fossil resources.　Examples of biomass include wood, seaweed, animal carcass and excreta, and plankton. "Derived from biomass" means that a substance is produced using an organic resource derived from an organism or a plant as at least a portion of a raw material and a substance produced using only a resource derived from fossil resources alone is excluded. In contrast, the substance produced using only a resource derived from fossil resources without using an organic resource derived from an organism or a plant is referred to as a substance "derived from fossil resources".　Examples of the resource derived from fossil include coal, petroleum, and natural gas. The polyester polyol of the present invention is a reaction product of raw material compounds containing the rosin (a), the biomass-derived fatty acid (b), the α,β-unsaturated carboxylic acid (c), and the polyol (d) as each described above.　Hereinafter, the raw material compounds constituting the polyester polyol of the present invention will be described in order. (Rosin (a)) 　　　 The rosin (a) is derived from biomass and is used as one of the raw material compounds constituting the polyester polyol.　The rosin (a) is generally obtained by distilling plant oleo