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Hydrolysis resistant organomodified disiloxane surfactants

A technology of organosilicon and solvents, which is applied in the direction of silicon organic compounds, biocides, animal repellents, etc.

Inactive Publication Date: 2012-07-18
MOMENTIVE PERFORMANCE MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, trisiloxane compounds are only available in a narrow pH range, from a slightly acidic pH 6 to a very mild alkaline pH 7.5

Method used

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  • Hydrolysis resistant organomodified disiloxane surfactants
  • Hydrolysis resistant organomodified disiloxane surfactants
  • Hydrolysis resistant organomodified disiloxane surfactants

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0100] 1-(2-Trimethylsilylethyl)-1,1,3,3-tetramethyldisiloxane (Structure 1). A 250 mL round bottom flask was charged with tetramethyldisiloxane (51.6 g) and Wilkinson's catalyst ((PPh 3 ) 3 RhCl, 100 ppm), stirred under nitrogen, and warmed to 60 °C. Trimethylvinylsilane (25.6 g) was charged to the addition funnel and added dropwise at a rate such that the reaction temperature was maintained R : M R m R . Fractional distillation of the resulting material under vacuum (about 30 mm Hg) afforded 51.6 g of M'M R Product, 99.1% GC purity. The Si-H content of the product was found to be 96cc H by gasiometric titration. 2 / g.

[0101] Structural Formula 1

[0102]

preparation Embodiment 2

[0104] 1-(3,3-Dimethylbutyl)-1,1,3,3-tetramethyldisiloxane (Structure 2). A 250 mL round bottom flask was charged with tetramethyldisiloxane (46.1 g) and stirred under nitrogen. A solution of Karstedt's catalyst (Pt(0) in divinyltetramethyldisiloxane, 10 ppm) in 3,3-dimethyl-1-butene (19.3 g) was charged to the addition funnel , added dropwise at a rate such that the reaction temperature was kept R Product and M R m R By-products (32:53:9). The resulting material was fractionated under vacuum (about 30 mm Hg) using a 25-cm Vigreux column to give 25.0 g M'M R Product, >98.1% GC purity. The Si-H content of the product was found to be 100cc H by gas titration 2 / g.

[0105] Structural formula 2

[0106]

preparation Embodiment 3

[0108] 1-(2-methylpropyl)-1,1,3,3-tetramethyldisiloxane (Structure 3). Tetramethyldisiloxane (10.0 g), toluene (10.0 g) and Wilkinson's catalyst ((PPh 3 ) 3 RhCl, 40ppm), stirred, and heated to 60°C. The bottle was manifolded and pressurized (25 psig) with isobutylene and maintained at 60-70°C for 8 hours. The pressure was vented and the reaction was sampled for GC analysis; residual tetramethyldisiloxane, M'M R Product and M R m R By-products (2:95:3). The resulting material was stripped at 40°C under vacuum (about 150 mm Hg) to remove olefins and M'M', then filtered through celite to give 21.3 g of M'M R Product / toluene solution, 94% GC purity. The Si-H content of the product was found to be 11cc H by gas titration 2 / g.

[0109] Structural formula 3

[0110]

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PUM

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Abstract

Compositions comprising an asymmetric disiloxane surfactant composition comprise an organosilicon composition comprising an organosilicon having the formula MM', where M or M' comprises an alkylpolyalkyleneoxide bearing substituent selected from the group consisting of: R<13>(C2H4O)a(C3H6O)b(C4H8O)cR<14> and R<12>SiR<5>R<6>(R<13>(C2H4O)a(C3H6O)b(C4H8O)cR<14>) exhibit resistance to hydrolysis over a wide pH range.

Description

[0001] Cross-references to related applications [0002] This application is a continuation-in-part of U.S. Application Serial No. 11 / 300,100 filed on December 13, 2005, which claims the benefit of U.S. Provisional Application Serial No. 60 / 726,409 filed on October 13, 2005. Technical field [0003] The present invention relates to disilicone surfactant compositions which exhibit resistance to hydrolysis over a broad pH range. More specifically, the present invention relates to such hydrolysis-resistant disiloxane surfactants that are hydrolysis-resistant between about pH 3 and about pH 12. Background technique [0004] Liquid compositions are topically applied to surfaces of animate and inanimate objects to produce desired changes, including controlled wetting, spreading, foaming, cleaning, and other processes. When used in aqueous solutions to improve the delivery of active ingredients to the surface being treated, it has been found that trisiloxane-type compounds can be ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08A61K8/58A61K8/898A01N65/00
CPCA01N25/30
Inventor 马克·D·莱瑟曼乔治·A·波利塞罗休尔什·K·拉贾拉曼
Owner MOMENTIVE PERFORMANCE MATERIALS INC