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Novel asymmetric substituted benzaldehyde alditol derivatives and compositions and articles containing same

a technology of benzaldehyde alditol and derivatives, which is applied in the field of new asymmetric substituted benzaldehyde alditol derivatives and compositions and articles containing same, and can solve the problem of difficult separation of individual compounds from reaction product mixtures

Inactive Publication Date: 2003-01-02
MILLIKEN & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the similar solubilities of such DBS compounds (in each instance, not just Example 3), it has been found to be extremely difficult to separate these individual compounds from the reaction product mixture.

Method used

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  • Novel asymmetric substituted benzaldehyde alditol derivatives and compositions and articles containing same
  • Novel asymmetric substituted benzaldehyde alditol derivatives and compositions and articles containing same
  • Novel asymmetric substituted benzaldehyde alditol derivatives and compositions and articles containing same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 4-t-butyl3,4-dimethyl DBS

[0031] D-Sorbitol (27 g, 0.15 mol), cyclohexane (500 mL), 4-t-butylbenzaldehyde (24 g, 0.15 mol), 3,4-dimethylbenzaldehyde (20 g, 0.15 mol), methanol (80 mL), water (2.5 g) and p-toluenesulfonic acid (3.0 g, 16 mmol) were added to a 2 L reaction kettle fitted with a mechanical stirrer, Dean-Stark trap with condenser and a thermometer. The system was flushed with argon and heated in an oil bath to reflux for 7 h. The methanol / water layer was continuously drained from the reaction system. Methanol was added as needed. The reaction mixture was cooled to room temperature and neutralized with KOH. The gray gel-like solid was filtered, washed three times with cyclohexane and dried in a vacuum oven to give mixture of 1,3;2,4-diacetal compounds determined through Infrared Spectroscopy, Gas Chromatography / Mass Spectrometry, .sup.1H NMR, and C.sup.13 NMR, all collectively hereinafter referred to as "standard analyses", to be an asymmetric mixture of 1,3...

example 2

Preparation of 3,4-dimethoxy / 3,4-dimethyl DBS

[0032] A two 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 g of sorbitol (0.23 mol), 2.5g of water, 80 mL of methanol, 38 g of 3,4-dimethoxybenzaldehyde (0.23 mol), 31g of 3,4-dimethylbenzaldehyde (0.23 mol), 3.3 g of p-toluenesulfonic acid and 700 mL of cyclohexane. The system was flushed with argon and heated in an oil bath to reflux for 5 h. The methanol / water layer was continuously drained from the reaction system. Methanol was added as needed. The reaction mixture was cooled to room temperature and neutralized with KOH. Water was then added and the cyclohexane layer was then stripped azeotropically, leaving a white solid collected by filtration. After washing with boiling water and boiling methanol, the result was a 3,4-dimethoxy / 3,4-dimethyl asymmetric DBS mixture determined through standard analyses by gas c...

example 3

Preparation of 4-isopropyl / 3, 4-dimethyl DBS

[0033] D-Sorbitol (27 g, 0.15 mol), cyclohexane (500 mL), 4-isopropylbenzaldehyde (22 g, 0.15 mol), 3,4-dimethylbenzaldehyde (20 g, 0.15 mol), methanol (80 mL) and water (2.5 g) were added to a 2 L reaction kettle fitted with a mechanical stirrer, Dean-Stark trap with condenser and a thermometer. The system was flushed with argon and heated in an oil bath to reflux for 7 h. The methanol / water layer was continuously drained from the reaction system. Methanol was added as needed. The reaction mixture was cooled to room temperature and neutralized with KOH. The gel-like solid was filtered, washed one time with cyclohexane and dried in a vacuum oven to give mixture four 1,3 ;2,4-diacetal compounds determined through standard analyses to be an asymmetric mixture of 1,3-O-(4-isopropylbenzylidene):2,4-O-(3,4-dimethylb-enzylidene) sorbitol and 1,3-O-(3, 4-dimethylbenzylidene)-2,4-O-(4-isoprop-ylbenzylidene) sorbitol (39%), 10% of bis(4-isopropylb...

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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 asymmetric DBS compounds comprising specific pendant groups, such as C1-C6 alkyl, C1-C6 alkoxy, phenyl, naphthyl, or substituted phenyl, or pendant groups combined to cyclic moities, such as cyclopentyl (and thus to form indan with the benzylidene), cyclohexyl (to form tetralin), and methylenedioxy (as the combination of two available sites on the pertinent ring system). Such compounds may be added to or incorporated within polymer compositions which may then be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive asymmetric benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspirant gel sticks. Preferably one of the benzylidene moieties is 3,4-disubstituted, with most preferably methyl groups in the 3 and 4 positions.

Description

[0001] 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 asymmetric DBS compounds comprising specific pendant groups, such as C.sub.3-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, phenyl, naphthyl, or substituted phenyl, or pendant groups that combine to form cyclic moities, such as trimethylene (and thus to form indan with the benzylidene), tetramethylene (to form tetralin), and methylenedioxy (as the combination of two available sites on the pertinent ring system). Such compounds may be added to or incorporated within polymer compositions which may then be utilized within, as merely examples, food or cosmetic containers and packaging. These inventive asymmetric benzylidene sorbitol acetals are also useful as gelling agents for water and organic solvents, particularly those used in the preparation of antiperspiran...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/49A61Q15/00C07D493/04C08L23/10
CPCA61K8/042A61K8/498A61Q15/00C07D493/04C08L23/10
Inventor JONES, JEFFREY R.MEHL, NATHAN A.
Owner MILLIKEN & CO
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