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Novel fluorinated and alkylated alditol derivatives and compositions and polyolefin articles containing same

a technology of fluorinated alditol and compositions, applied in the field of new fluorinated alditol derivatives and compositions, polyolefin articles containing same, can solve the problem that the composition may not be sufficiently improved in respect of transparency characteristics

Inactive Publication Date: 2002-05-23
MILLIKEN & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0034] A one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser, thermometer, nitrogen inlet, and a mechanical stirrer was charged with 40.55 g of sorbitol (0.2226 mole), 600 mL of cyclohexane, 61.50 g of 4-fluoro-3-methylbenzaldehyde (0.4452 moles), 2.90 g of p-toluenesulfonic acid, 2.4 mL of water, and 210 mL of methanol. The reaction was stirred and heated under reflux with removal of water through the Dean Stark trap. The reaction becomes very thick and additional solvent is added as needed. After about six hours, the reaction is cooled, neutralized with potassium hydroxide, and filtered. The wet cake was washed thoroughly with water and cyclohexane, dried in a vacuum oven at 110.degree. C. to give 74.20 g of Bis(4-fluoro-3-methylben-zylidene)sorbitol (as determined through Infrared Spectroscopy, Gas Chromatography / Mass Spectrometry, .sup.1H NMR, and C.sup.13 NMR, all collectively hereinafter referred to as "standard analyses"). The purity was about 95% as determined by gas chromatography (GC). The melting point was determined to be [by Differential Scanning Calorimetry (DSC)@20.degree. C / min] about 237.8.degree. C.

Problems solved by technology

When the content of the di-acetal is less than about 0.01 percent by weight, the resulting composition may not be sufficiently improved in respect to transparency characteristics.

Method used

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  • Novel fluorinated and alkylated alditol derivatives and compositions and polyolefin articles containing same
  • Novel fluorinated and alkylated alditol derivatives and compositions and polyolefin articles containing same
  • Novel fluorinated and alkylated alditol derivatives and compositions and polyolefin articles containing same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Bis(4-fluoro-3-methylbenzylidene)sorbitol

[0034] A one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser, thermometer, nitrogen inlet, and a mechanical stirrer was charged with 40.55 g of sorbitol (0.2226 mole), 600 mL of cyclohexane, 61.50 g of 4-fluoro-3-methylbenzaldehyde (0.4452 moles), 2.90 g of p-toluenesulfonic acid, 2.4 mL of water, and 210 mL of methanol. The reaction was stirred and heated under reflux with removal of water through the Dean Stark trap. The reaction becomes very thick and additional solvent is added as needed. After about six hours, the reaction is cooled, neutralized with potassium hydroxide, and filtered. The wet cake was washed thoroughly with water and cyclohexane, dried in a vacuum oven at 110.degree. C. to give 74.20 g of Bis(4-fluoro-3-methylben-zylidene)sorbitol (as determined through Infrared Spectroscopy, Gas Chromatography / Mass Spectrometry, .sup.1H NMR, and C.sup.13 NMR, all collectively...

example 2

Preparation of Bis(3-fluoro-4-methylbenzylidene)sorbitol

[0035] A one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser, thermometer, nitrogen inlet, and a mechanical stirrer was charged with 42.00 g of sorbitol (0.2306 mole), 600 mL of cyclohexane, 63.70 g of 3-fluoro-4-methylbenzaldehyde (0.4611 moles), 3.00 g of p-toluenesulfonic acid, 2.5 mL of water, and 210 mL of methanol. The reaction was stirred and heated under reflux with removal of water through the Dean Stark trap. The reaction becomes very thick and additional solvent is added as needed. After about six hours, the reaction is cooled, neutralized with potassium hydroxide, and filtered. The wet cake was washed thoroughly with water and cyclohexane, dried in a vacuum oven at 110.degree. C. to give 85.18 g of Bis(3-fluoro-4-methylben-zylidene)sorbitol (as determined through standard analyses). The purity was about 95% as determined by GC. The melting point was determined to be (DS...

example 3

Preparation of Bis(4-fluoro-3-methylbenzylidene)xylitol

[0036] A one liter four-necked cylindrical shaped reaction flask equipped with a Dean-Stark trap, condenser, thermometer, nitrogen inlet, and a mechanical stirrer was charged with 35.08 g of xylitol (0.2306 mole), 600 mL of cyclohexane, 63.70 g of 4-fluoro-3-methylbenzaldehyde (0.4611 moles), 3.00 g of p-toluenesulfonic acid, 2.5 mL of water, and 210 mL of methanol. The reaction was stirred and heated under reflux with removal of water through the Dean Stark trap. The reaction becomes very thick and additional solvent is added as needed. After about six hours, the reaction is cooled, neutralized with potassium hydroxide, and filtered. The wet cake was washed thoroughly with water and cyclohexane, dried in a vacuum oven at 110.degree. C. to give 69.46 g of Bis(4-fluoro-3-methylben-zylidene)xylitol (as determined through standard analyses). The purity was about 95% as determined by GC. The melting point was determined to be (DSC@2...

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Abstract

Plastic additives which are useful as nucleating agents and which are especially useful for improving the optical properties of polymeric materials are provided. More particularly, this invention relates to certain alkyl (or alkoxy) substituted fluorobenzylidene sorbitol acetals and polymer compositions thereof which may be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive fluorinated and alkylated benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspirant gel sticks.

Description

[0001] This application is a continuation-in-part of co-pending application Ser. No. 09 / 653,935, filed on Sep. 1, 2000. This parent application is herein entirely incorporated by reference.[0002] This invention relates to plastic additives which are useful as nucleating agents and which are especially useful for improving the optical properties of polymeric materials. More particularly, this invention relates to certain alkyl (or alkoxy) substituted fluoro-benzylidene sorbitol acetals and polymer compositions thereof which may be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive fluorinated and alkylated benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspirant gel sticks.BACKGROUND OF THE PRIOR ART[0003] All U.S. Patents cited below are herein entirely incorporated by reference.[0004] Numerous attempts have been made to improve the clarity ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/49A61Q15/00C07B61/00C07C45/49C07C47/55C07D493/04
CPCC07C45/49C07C47/55C07D493/04
Inventor ANDERSON, JOHN D.MEHL, NATHAN A.
Owner MILLIKEN & CO