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Esters of aromatic alkoxylated alcohols and fatty carboxylic acids

A hydrocarbon-based, compound-based technology, used in cosmetics and personal care products, can solve problems such as poor solubility/dispersibility, poor solubility/dispersibility, uneven dispersion of active ingredients, etc.

Inactive Publication Date: 2012-09-26
克洛达股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some commonly used sunscreen actives have poor solubility / dispersibility in product formulations
Inhomogeneous dispersion of active ingredients can lead to reduced sunscreen quality and performance
Likewise, fragrances found in many cosmetic and personal care products can also have poor solubility / dispersibility, making it difficult to incorporate fragrances into product formulations

Method used

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  • Esters of aromatic alkoxylated alcohols and fatty carboxylic acids
  • Esters of aromatic alkoxylated alcohols and fatty carboxylic acids
  • Esters of aromatic alkoxylated alcohols and fatty carboxylic acids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0324] Embodiment 1. prepares PPG-3 benzyl ether

[0325] 2297.75 grams (21.24 moles) of benzyl alcohol were placed in a dry, stirred pressure vessel fitted with a nitrogen inlet. A catalytic amount (6 g) of 40% aqueous KOH was added. Nitrogen was bubbled through the vessel and heated to 110°C. A vacuum was applied for 1 hour to remove water vapor from the headspace of the vessel and the mixture was further heated to 130°C. After addition of 3702.25 grams (63.74 moles) of propylene oxide, the reaction mixture was stirred for 3 hours to complete the reaction. The progress of the reaction is monitored by uptake of the reagents and by measuring the pressure in the vessel. The reaction mixture was cooled to 110°C and vacuum was applied for about 1 hour. 29 grams of 25% sulfuric acid were added to neutralize the KOH in the reaction mixture. The mixture was stirred for 10 minutes and the pH was adjusted to 5.7. After cooling, the main product, PPG-3 benzyl ether, was isolated ...

Embodiment 2

[0326] Example 2. Preparation of PPG-3 benzyl myristate

[0327] In a four-necked flask with mechanical stirrer, thermometer and nitrogen inlet, 342.44 g (1.19 mol) of PPG-3 benzyl ether, 221 g (1.13 mol) of myristic acid and 0.45 g of SnO were charged. The mixture was heated to 220°C. The progress of the reaction was monitored by measuring the acidity value of the reaction mixture over time. After the acidity value stabilized, the mixture was cooled to 25°C. Add 0.9 g of 30% HO 2 o 2 solution and 70 g of water, and the mixture was again heated to 75°C. The water was evaporated under vacuum to give PPG-3 benzyl myristate as the main product.

Embodiment 3

[0328] Embodiment 3. preparation two-(PPG-4) bisphenol A ether

[0329] 1233.86 grams (5.40 moles) of bisphenol A and 1445 milliliters of toluene were placed in a clean, dry, stirred pressure vessel tank with nitrogen inlet. Bubble nitrogen into the vessel and add a catalytic amount (4.86 g) of BF 3 / etherate solution. The temperature was raised to 110°C, and 2511.29 grams (43.24 moles) of propylene oxide was added at a constant rate, keeping the pressure in the vessel below 50 psi. After all the propylene oxide had been added, the reaction mixture was warmed up to 150° C. and reacted for another 3 hours, then the toluene was distilled off under a nitrogen sparge. The temperature was then lowered to 110°C and a vacuum was applied for 1 hour.

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PUM

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Abstract

Esters of alkoxylated aromatic alcohol and fatty carboxylic acid are provided. The esters are especially suitable as additives for personal care and cosmetic products. Certain of the esters of alkoxylated aromatic alcohol and fatty carboxylic acid having certain skin spread factor or viscosity are also provided. A personal care or cosmetic product composition that includes from about 0.1% to about 99% of at least one ester of alkoxylated aromatic alcohol and fatty carboxylic acid, and from about 0.1% to 60% of at least one functional ingredient is provided. The functional ingredients in the composition 15 may include active ingredients and additional ingredients. Especially suitable active ingredients are sunscreen active ingredients and antiperspirant active ingredients. Preferred compositions are sunscreen product formulations and antiperspirant products. In one preferred embodiment, the composition further includes at least one cyclomethicone compound present in the amount of from about 1% to 99% by weight of the composition. A method of improving the protection of human or animal skin or hair from radiation and a method of improving the protection of human or animal skin or hair from perspiration are also provided.

Description

field of invention [0001] The present invention relates to the field of chemical manufacturing, and in particular to cosmetics and personal care products. Background of the invention [0002] Personal care and cosmetic formulations such as shampoos, conditioners, sunscreen lotions, lipsticks, mascaras and similar products leave much to be desired. The feel and appearance of these products should appeal to consumers. For example, it is desirable for certain products to have a non-greasy skin feel, good skin spreadability, pleasant odor, and other advantages. At the same time, cosmetic and personal care products often include many essential components. For formulators, the need to achieve consumer-appealing physical properties coexists with the need to incorporate functional ingredients into products. [0003] Personal care and cosmetic products often include compounds that act as emollients. Emollients help provide the desired skin feel and perform other functions in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C53/00C07C57/00A61K6/00A61K31/215A61K31/235A61K31/22A61K31/225A61K8/19A61K8/00A61K8/26A61K8/29A61K8/30A61K8/31A61K8/37A61K8/39A61K8/40A61K8/41A61K8/46A61K8/49A61K8/55A61K8/58A61K8/64A61K8/89A61K8/891A61K8/92A61Q5/02A61Q5/12A61Q15/00A61Q17/04A61Q19/00A61Q19/10C07C69/24C07C69/28
CPCA61K8/39A61Q19/00A61Q15/00A61Q5/02A61Q17/04A61Q5/12
Inventor A·佩雷拉C·韦斯特戈姆P·欧布科和
Owner 克洛达股份有限公司