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Dithiophosphate composition and utility in rubber

A technology of dithiophosphoric acid and composition, applied in phosphorus organic compounds, compounds of group 5/15 elements of the periodic table, organic chemistry, etc., can solve problems such as toxins

Inactive Publication Date: 2010-03-31
VANDERBILT CHEM LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although dithiophosphate technology does not form harmful nitrosamines, one concern with this technology is its ability to become a toxin

Method used

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  • Dithiophosphate composition and utility in rubber
  • Dithiophosphate composition and utility in rubber
  • Dithiophosphate composition and utility in rubber

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Dithiophosphoric acid, Lot RJT-543-233

[0030] Add 86.2 grams of phosphorus pentasulfide and 100 mL of heptane into the three-necked flask. The flask was connected to a scrubber to remove hydrogen sulfide gas that would form during the reaction. A mixture of 85.1 grams of 2-ethylhexanol, 24.3 grams of n-butanol and 39.0 grams of 1,6-hexanediol was added to the addition funnel. The addition funnel was heated to 44°C to dissolve the 1,6-hexanediol solid in the other two alcohols. The mixture was then added to the phosphorus pentasulfide mixture over 15 minutes. The addition funnel was washed with 20 mL of heptane, which was then added to the reaction mixture. The reaction was gradually heated to 105°C and maintained at this temperature for two and a half hours. The temperature was then raised to 120°C as the heptane was distilled off. The reaction was maintained at 125°C for about four hours. The reaction was then attached to an aspirator to ensure all ...

Embodiment 2

[0031] Example 2: Polymeric dithiophosphate OCD-337, Lot RJT-543-241

[0032] 191.3 grams of dithiophosphoric acid (RJT-543-233) in Example 1 was added to the three-necked flask. This was attached to an addition funnel containing a mixture of water (42.2 g) and 30% hydrogen peroxide (42.1 g, 0.371 moles). The reaction flask was placed in an ice water bath and the hydrogen peroxide solution was added slowly over three hours. The addition funnel was then washed with 40 mL of water and added to the reaction. The reaction temperature was kept below 40°C while hydrogen peroxide was added. The reaction was then heated to 56°C and then allowed to cool back to room temperature. Another 2.5 g of 30% hydrogen peroxide was added. Then stir for about 30 minutes. The product was mixed with 79.6g of Hi- ABS (a solid carrier) was mixed and dried in a 46°C oven to obtain a homogeneous powder.

Embodiment 3

[0033] Example 3: Dithiophosphoric acid for the preparation of OCD-338, Lot RJT-543-244

[0034] 74.1 g of phosphorus pentasulfide and 60.2 g of heptane were added to the three-necked flask. The flask was connected to a scrubber to remove any hydrogen sulfide gas that would form during the reaction. The flask was then placed in an ice water bath. To the addition funnel was added 37.2 grams of dipropylene glycol and 104.4 grams of 2-ethylhexanol. The alcohol mixture was then added to the phosphorus pentasulfide over 15 minutes. The addition funnel was rinsed with 20 mL of heptane and added to the reaction flask. The reaction was slowly heated to 115°C and the heptane was distilled off. The reaction was heated at 115 °C for 4.5 hours and then attached to an aspirator to remove any residual solvent. After another 30 minutes, the aspirator was removed and the product was filtered through celite.

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Abstract

The present invention relates to oligomeric or polymer dithiophosphate di- or poly- sulfides and their utility in rubbers. Another aspect of the invention is a method for making oligomeric or polymeric dithiophosphates by reacting phosphorous pentasulfide with a di- or polyol and a mono alcohol to produce a dithiophosphoric acid, and then oxidizing the dithiophosphoric acid with an oxidizing agent to produce an oligomeric or polymeric dithiophosphate.

Description

field of invention [0001] The present invention relates to polymer compositions and methods of making the compositions. More specifically, the polymer compositions comprise novel polymeric dithiophosphates. Background of the invention [0002] Dithiophosphate accelerators are used as sulfur donors during the vulcanization of dienes. Compared to conventional accelerators, they offer advantages such as improved reversion properties of natural rubber, thermal stability of vulcanized or prepared rubbers and high solubility in polarized rubbers. The high solubility in polarizing rubbers allows for vulcanization and preparation of additive-bleed-free ("non-bloom") products. [0003] Commercially available dithiophosphate additives are: (1) "Accelerator ZIPPAC" from Akrochem. ZIPPAC is an aminodithiophosphate zinc complex dispersed in a polymer matrix. When ZIPPAC is used in combination with thiazoles and thiurams, fast cure rate ENB type EPDM's are obtained. Compared with Acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/04
CPCC07F9/17C08G79/04C08G75/14C08K5/5398C08L21/00C08G79/02C07F9/04
Inventor 托马斯·J·卡罗尔罗纳德·J·泰珀
Owner VANDERBILT CHEM LLC
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