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Enol-ether capped polyethers and surfactants produced therefrom

a technology of enol-ether capped polyethers and surfactants, which is applied in the direction of group 4/14 element organic compounds, chemistry apparatus and processes, etc., can solve the problems of serious deficiency, acetate cap is not hydrolytically stable to acidic or alkaline water, and the williamson ether process has a number of problems, and achieves good potency.

Inactive Publication Date: 2002-05-21
GENERAL ELECTRIC CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides the use of Copolymers that offer good potency which have the generalized average formula M"D.sub.x D".sub.y T.sub.z M" wherein

Problems solved by technology

Essentially 100% capping can readily be achieved but the acetate cap is not hydrolytically stable to acidic or alkaline water.
This is a serious deficiency with customers who operate by blending the surfactant into the water / amine premix prior to making foam.
Unfortunately, the Williamson Ether process has a number of problems.
This low capping efficiency generally results is not being able to produce as good airflow performance characteristics as observed with acetoxy-capped polyethers.
In addition, the process involves handling toxic methylchloride gas as well as separating and disposing of large quantities of NaCl waste.
With allyl-terminated polyethers, the harsh conditions used to generate the alkoxide can also rearrange the allyl group to a propenyl group, thus rendering a substantial portion of the polyether unreactive to the subsequent copolymer synthesis step.

Method used

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  • Enol-ether capped polyethers and surfactants produced therefrom
  • Enol-ether capped polyethers and surfactants produced therefrom
  • Enol-ether capped polyethers and surfactants produced therefrom

Examples

Experimental program
Comparison scheme
Effect test

example 1-- stability study

Example 1--Stability Study

To test the stability of a pyran cap, methyltriglycol (MTG) was capped with 2,3-Dihydro-4H-pyran using conditions described in U.S. Pat. No. 3,794,673 (Example 1). GC analysis indicates 97% capping was achieved. A sample of the resulting material (0.35g) was mixed with a conventional flexible foam formulation water / amine premix (1.15g of a 5.5:0.2 wt / wt water / A-200 amine mixture). Blends of acetoxy- and alkyl-capped MTG samples with conventional water / amine premix were similarly prepared (alkyl=C.sub.3 H.sub.5 and MTG-Acetate (MTG-Ac) which were prepared via conventional means). The hydrolysis at a room temperature of the different capping groups was followed by GC. The results in Table 1 clearly show the acetoxy group cleaving rapidly to about 15-20% uncapped which is approximately the level at which the liberated acetic acid would neutralize all of the amine in the mixture. The pyran-capped material exhibits excellent stability, comparable to the alkyl-ca...

example 2--

Capping Efficiency

Using a variety of acid catalysts, a broad spectrum of conventional polyethers of the type used for Copolymer synthesis were enol-ether capped. Excellent results were obtained even with random mixed feed polyethers such as 40 weight percent EO fluids that generally are approximately 95% 2.degree. alcohols (due to the sluggish nature of PO reaction during the last stages of polyether manufacture). Thus Table 3 shows that the technology readily caps even high molecular weight, high 2.degree. hydroxy polyethers very efficiently.

TABLE 3 Representative Capping Results. Acid % Polyether* Enol-Ether (% Excess) Catalyst Capping 100HA550 2,3-Dihydro-4H-pyran (50%) PTSA >98 Ethylvinyl Ether (14%) A-18 Resin >98 40HA1500 2,3-Dihydro-4H-pyran (50%) PTSA >98 Ethylvinyl Ether (14%) A-18 Resin -98 Ethylvinyl Ether (25%) H.sub.2 SO.sub.4 >98 40HA4000 2,3-Dihydro-4H-pyran (50%) PTSA >98 Ethylvinyl Ether (25%) H.sub.2 SO.sub.4 >98 75HA750 2,3-Dihydro-4H-pyran (50%) PTSA -98 *These a...

example 3--

Manufacture of Flexible Polyurethane Foam

In the examples that follow, all reactions involving the manipulation of organometallic compounds were performed in an inert atmosphere. Commercial reagents were used without additional purification.

The term potency refers to the ability of a surfactant to stabilize foam during its manufacture. High potency surfactants allow high heights of rise and only relatively small amounts of top collapse during foam manufacture. In general, higher rise and / or good rise at lower and lower use levels are desirable. The phrase "processing latitude" refers to the ability of a foam composition to tolerate changes in its ingredients or amounts thereof, while still producing product having the desired properties. In flexible foam applications, this is often reflected by relatively small changes in foam properties (such as breathability) at higher and higher surfactant or catalyst use levels. The terms breathability or airflow refer to the ability of a cured f...

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Abstract

The use of enol ether capped polyether-polysiloxane copolymers as surfactants in polyurethane foam applications is taught herein. These enol ether capped surfactants exhibit a high capping efficiency and yield good performance. Moreover, they are stable in water / amine premixes.

Description

BACKGROUND OF THE INVENTIONIn polyurethane foam manufacturing, surfactants are needed to stabilize the foam until the product-forming chemical reactions are sufficiently complete so that the foam supports itself and does not suffer objectionable collapse. High potency silicone surfactants, generally understood to be those which give a high height of rise and little top collapse at minimal use levels, are desirable because foams which collapse to a substantial degree before setting have high densities and objectionable density gradients. In general, it is preferred that the surfactant also gives high airflow performance. The latter feature refers to the ability of air to pass through the foam.Silicone surfactants for polyurethane foam manufacture typically are materials having siloxane backbones and polyether pendant groups (hereinafter "Copolymers"), see for example, U.S. Pat. No. 4,147,847. The importance of the capping group on the ungrafted end of the polyether pendant is well kn...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08J9/00C08G77/00C08G77/46C08G18/00C08J9/04C08G101/00
CPCC08G77/46C08J9/0061C08J2375/04C08J2483/00C08J9/08
Inventor MILLER, GLENN A.
Owner GENERAL ELECTRIC CO
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