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Novel shrinkage synthesis of 2-methoxymethyl-p-phenylenediamine

A technology of methoxymethyl and phenylenediamine, which is applied in the field of new-type condensation synthesis, and can solve the problems of negative impact on the appearance of powder materials

Pending Publication Date: 2022-07-22
WELLA GERMANY GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A particular disadvantage of this method is that the obtained product contains amorphous material which may lead to undesired side effects such as surface oxidation
Surface oxidation, in turn, can negatively affect the appearance of powdered materials, which can be a success criterion for cosmetic applications / formulations

Method used

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  • Novel shrinkage synthesis of 2-methoxymethyl-p-phenylenediamine
  • Novel shrinkage synthesis of 2-methoxymethyl-p-phenylenediamine
  • Novel shrinkage synthesis of 2-methoxymethyl-p-phenylenediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Example 1: Synthesis of 2-methoxymethyl-p-phenylenediamine (I) using 1,4-benzoquinone (VIII) as starting material

[0150] (1) Synthesis of 2-methoxymethyl-1,4-benzoquinone (IV)

[0151] A three-necked flask was fitted with a reflux condenser and thermometer and charged with 1 equiv = 1,41 g (8,24 mmol) of silver nitrate and a 1:1 mixture of dichloromethane and water (98 mL) in the presence of 0,3 equiv = 1,41 g (8,24 mmol). 3 g (27,5 mmol) of 1,4-benzoquinone (VIII), 1,5 equiv = 3,71 g (41,2 mmol) of 2-methoxyacetic acid (IX). The 2-phase mixture was stirred until complete dissolution was observed. The mixture was then heated to 40°C under reflux to float any sublimed 1,4-benzoquinone (VIII) back to the top of the flask. Ammonium peroxodisulfate (1,05 equiv = 6,72 g (28,8 mmol)) was then slowly added as a free radical former at a rate of 10 mL / h using a syringe driver or pump (dosimat) solution in water. The reaction mixture was kept at 40°C throughout the addition...

Embodiment 2

[0163] Example 2 Synthesis of 2-methoxymethyl-p-phenylenediamine (I) using 1,4-benzoquinone (VIII) as starting material

[0164] (1) Synthesis of 2-methoxymethyl-1,4-benzoquinone (IV)

[0165] A three-necked flask was fitted with a reflux condenser and thermometer and charged with 462 g of 1,4-benzoquinone ( VIII), 1,5 equivalents = 578 g of 2-methoxyacetic acid (IX). The 2-phase mixture was stirred until complete dissolution was observed. The mixture was then heated to 39°C under reflux to float any sublimed 1,4-benzoquinone (VIII) back to the top of the flask. Then a solution of 1073 g of ammonium peroxodisulfate as a free radical former in 2080 mL of water was slowly added over 1 hour. The reaction mixture was kept at 40°C throughout the addition. After the addition was complete, the mixture was stirred at 39°C under reflux for an additional 2 hours. HPLC analysis showed 60% conversion from benzoquinone (VIII) to the desired intermediate 2-methoxymethyl-1,4-benzoquinon...

Embodiment 3

[0177] Example 3: Synthesis of 2-methoxymethyl-p-phenylenediamine (I) and p-phenylenediamine (XI) as a by-product

[0178] (1) Synthesis of 2-methoxymethyl-1,4-benzoquinone (IV)

[0179] A three-necked flask was fitted with a reflux condenser and thermometer and charged with 1 equiv = 3 g (27,5 mmol) of 1 in the presence of 0,3 equiv = 1,41 g (8,24 mmol) of silver nitrate and water (98 mL). 4-Benzoquinone (VIII), 1,5 equiv = 3,71 g (41,2 mmol) of 2-methoxyacetic acid (IX). The mixture was stirred and heated to 65°C until complete dissolution was observed. The aqueous phase was continuously floated with a pump to avoid sublimation of 1,4-benzoquinone (VIII) at the top of the flask. Ammonium peroxodisulfate (1,05 equiv = 6,72 g (28,8 mmol)) was then slowly added as a free radical former at a rate of 10 mL / h using a syringe driver or pump (dosimat) solution in water. The reaction mixture was maintained at 65°C throughout the addition. After the addition was complete, the mix...

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PUM

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Abstract

The present invention relates to a process for the preparation of 2-methoxymethyl-p-phenylenediamine (I), the cosmetically acceptable salts thereof or mixtures thereof.

Description

technical field [0001] The present invention relates to a novel telescoping synthesis of 2-methoxymethyl-p-phenylenediamines or salts thereof according to formula (I). This compound is known in the industry as a hypoallergenic primary dye precursor for use in oxidative hair dye compositions as a replacement for traditional p-phenylenediamine or p-toluenediamine dye precursors. [0002] Background technique [0003] P-phenylenediamine derivatives are important precursors for oxidative hair dyeing. They are usually used to create dark shades. P-phenylenediamine derivatives have been used for decades in hair dyeing. Among the p-phenylenediamine derivatives, a particularly favorable candidate, 2-methoxymethyl-p-phenylenediamine, has been identified. Such dye precursors are particularly advantageous because they are typically characterized by a lower sensitization potential than conventional p-phenylenediamine or p-toluenediamine dye precursors. [0004] In the past, diffe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C50/04C07C217/76
CPCC07C213/02C07C46/00C07C217/76C07C50/24C07C50/28
Inventor 马库斯·施佩克巴切尔阿明·奥桑海克·阿贝尔格尔德·施洛茨豪尔
Owner WELLA GERMANY GMBH
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