Aromatic Polyester Polyols and Aromatic Polyester Polyol Blends Containing Biorenewable Components and Methods of Making

Abstract

There are provided aromatic polyester polyol compositions comprising: (i) at least one aromatic acid component; (ii) at least one hydroxylated component; (iii) at least one functionalized natural oil component; and (iv) optionally at least one catalyst component for use in preparing foams. The aromatic polyester polyol compositions can be formed by esterification and / or transesterification. The present technology also provides a polyol blend for use in preparing foams wherein the polyol blend comprises (a) an aromatic polyester polyol formed by an interesterification reaction between (i) a phthalic acid based material; (ii) a hydroxylated material; and (iii) a hydrophobic material, wherein the hydrophobic material is present in an amount of from about 1% to about 50% by weight of the aromatic polyester polyol; and (b) a natural oil based polyol, wherein the hydrophobic material in the aromatic polyester polyol compatibilizes the natural oil based polyol to form a phase stable polyol blend.

Description

RELATED APPLICATIONS[0001]This application is a continuation of International application Serial No. PCT / US2008 / 077993 (International Publication No. WO / 2009 / 045926), having an International filing date of Sep. 26, 2008. This PCT application claims priority to U.S. Provisional Application No. 60 / 976,182 filed on Sep. 28, 2007 and U.S. Provisional Application No. 61 / 085,342 filed on Jul. 31, 2008. The entire specifications of the PCT and provisional applications referred to above are hereby incorporated by reference.BACKGROUND OF THE INVENTION[0002]The use of biorenewable components as substitutes, either in whole or in part, for petrochemical derived raw materials is an emerging trend in the chemical industry. At least one benefit includes the use of a raw material that is non-depleting of fossil resources (i.e. renewable), and in some cases a reduction in lifecycle global warming potential due to the fixation of CO2 in plant biomass from which the biorenewable materials are derived...

AI Technical Summary

Benefits of technology

[0008]In one aspect of the present technology, several advantages and benefits are obtained when an aromatic acid based material (e.g., phthalic acid based material) that has been interesterified with a hydroxylated material and a hydrophobic material is blended with one or more natural oil based polyols to make an aromatic polyester polyol / natural oil based polyol blend. Normally aromatic polyester polyols and natural oil based polyols are incompatible and separate into two separate phases after mixing. However, phase stable and compatible blends of aromatic polyester polyols and natural oil based polyols can be obtained by (1) inter- or transesterifying the aromatic polyester polyol with a hydrophobic material before blending the aromatic polyester polyol and the natural oil based polyol; (2) by adding a nonionic surfactant in order to compatibilize the natural oil based polyol with the aromatic polyester polyol to form the phase stable blend; (3) by utilizing both the aromatic polyester polyol transesterified with the hydrophobic material and the nonionic surfactant, or (4) by transesterifying the aromatic polyester polyol with a functionalized natural oil.

[0009]Another aspect of the present technology relates to phase stable blends of aromatic polyester polyols and natural oil based polyols. In one aspect, the aromatic polyester polyol comprises the interesterification of (a) an aromatic acid based material, (b) a hydroxylated material, and (c) a hydrophobic material. In another embodiment, the aromatic polyester polyol is a phthalate polyester polyol comprising the reaction products of (a) phthalate acid based materials, (b) low molecular weight aliphatic diol compounds, and (c) certain hydrophobic materials. Suitable hydrophobic materials include, for example, carboxylic acids (especially fatty acids), lower alkanol esters of carboxylic acids (especially fatty acid methyl esters, fatty acid alkanolamides, natural oils, and triglycerides (especially fats and oils) derived from renewable resources. The reacting of the hydrophobic material, e.g., natural oil with the aromatic polyester polyol compatibilizes the aromatic polyester polyol so that it can be further blended with a natural oil polyol. The aromatic polyester polyol blended with the natural oil polyol provides phase stable aromatic polyol blends.

Problems solved by technology

There are challenges to the use of natural oils as raw materials for polyols to be used in isocyanate based foam products (e.g. polyurethanes and polyisocyanurates).

The properties (e.g. compressive strength, green strength, reactivity, thermal stability) of resultant foams formed from the reaction of functionalized natural oils with isocyanate are typically deteriorated relative to foams made solely from petrochemical polyols.

This deterioration of foam properties can be due, at least in part, to the plasticization of the foam by the relatively high aliphatic concentration of the natural oils.

The deterioration of foam properties can also be due, at least in part, to the poor reactivity of the functional group due to steric hindrance by the aliphatic chains of the oil, and the incompatibility of the natural oil polyol with the isocyanate.

Also, when natural oils are used in combination with petrochemical polyols, the natural oil is frequently not compatible with the petrochemical polyol, which again results in the deterioration of foam properties.

This is often the case with aromatic polyester polyols, and compatibility becomes an important issue, both for the polyol producer desiring to market an aromatic polyester polyol containing natural oil-derived renewable content, and for the end user.

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