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

a technology of aromatic polyester and polyester polyol, which is applied in the field of aromatic polyester polyol blends containing biorenewable components and making methods, can solve the problems of deterioration of foam properties, and use of natural oils

Inactive Publication Date: 2010-09-23
STEPAN COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present technology relates to a method of blending aromatic polyester polyols and natural oil based polyols to create a stable blend. This is achieved by using a hydrophobic material to modify the aromatic polyester polyol before blending it with the natural oil based polyol. The resulting blend has improved compatibility between the two polyols and can be used to make polyisocyanate-based foams. The use of a nonionic surfactant as a compatibilizer can further improve the blend. The technical effects of this technology include improved stability and compatibility between aromatic polyester polyols and natural oil based polyols, as well as improved foam properties.

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.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

example 1

Phase Stable Polyol Blends

[0141]Mixtures of phthalic acid based polyester polyols and renewable polyols (natural oil) were prepared by combining the two materials in a scintillation vial in the ratios noted in Table 1 below. The aromatic polyol was added first and the renewable polyol was added second. The scintillation vial was then heated to 60° C. and the materials were mixed well by hand stirring. The initial appearance of each of the mixtures was noted. The mixtures were then allowed to cool overnight and then the compatibility of each of the mixtures was noted. The results for each of the mixtures are reported in Table 1.

TABLE 1Aromatic% TransesterifiedRenewableWt. %RunPolyesterOil in AromaticPolyolRenewableAppearanceAppearanceNo.PolyolPolyester PolyolAddedPolyolAfter mixingAfter 1 dayCompatibility1PA polyol 18castor oil25cloudyseparatedseparates2PA polyol 410castor oil25cloudyseparatedseparates3PA polyol 730castor oil25cloudyseparatedseparates4PA polyol 650castor oil25cloudy...

example 2

Use of Nonionic Surfactants and Transesterified Natural Oil in Phase Stable Polyol Blends

[0143]In this example, mixtures of aromatic polyester polyols and renewable polyols were evaluated with and without added nonionic surfactants for compatibility. The types and amounts of polyols comprising each mixture and the compatibility results are reported in Table 2.

TABLE 2Max %AromaticRenewableRenewableRunPolyesterCompatibi-PolyolPolyolNo.Polyollizer(s)*AddedCompatible**1STEPANPOLnonecastor oilPS-240221929-95A18%castor oil4reacted SBO31929-95A15.3%castor oil6reacted SBO,15% Toximul82404STEPANPOLnoneVikol 1PS-240251929-95A18%Vikol 15reacted SBO61929-95A15.3%Vikol 18reacted SBO,15% Toximul8240*Percentages based on final composition, aromatic polyester polyol with compatibilizers, before renewable polyol addition.**“Compatible” means clear or slightly hazy, no separation of phases. Above this level, mixture becomes very hazy, and separates on standing. Percentages based on total blend, aro...

example 3

Nonionic Surfactant as Sole Compatiblizer for Phase Stable Polyol Blends

[0145]In this example, a nonionic surfactant is used as the only compatibilizer for the mixtures of aromatic polyester polyols and renewable polyols. In other words, the aromatic polyester polyol contained no transesterified triglyceride oil. The polyols and nonionic surfactants used for each mixture and the compatibility results obtained are reported in Table 3.

TABLE 3Max %RenewablePolyolAromaticRenewableCompatiblePolyesterCompatibi-Polyol(1 hour, roomNo.PolyollizerAddedtemperature)1STEPANPOLNoneESO Polyol 11PS-24022STEPANPOL14% ToximulESO Polyol 16PS-240282403STEPANPOL13%ESO Polyol 115PS-2402Surfactant 2Percentages based on total blend, aromatic polyester polyol + compatibilizer + renewable polyol.“Compatible” means clear or slightly hazy, no separation of phases.

[0146]The results in Table 3 demonstrate that a nonionic surfactant can effectively compatibilize a renewable polyol.

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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...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G18/42
CPCC08G18/36C08G18/4288C08G18/6662C08G63/20C08G63/668C08G18/06C08G2101/0025C08G2101/005C08G2105/02C08J9/141C08J2375/06C08G63/916C08G2110/005C08G2110/0025C08G2115/02
Inventor HICKEY, F. LEOLAMBERT, TIMOTHYYAO, CHUNHUA
Owner STEPAN COMPANY
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