Polymer-filler coupling additives

A polymer and compound technology, applied in chemical/physical processes, transportation and packaging, organic chemistry, etc., can solve problems such as dispersion and mutual aggregation contact reduction

Inactive Publication Date: 2007-12-05
BRIDGESTONE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of these approaches have focused on increased interactions between elastomers and carbon black compounding materials, resulting in stable dispersion of individual carbon black aggregates and a reduction in interaggregate contact

Method used

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  • Polymer-filler coupling additives
  • Polymer-filler coupling additives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Preparation of 4-(2-oxazolyl)-phenyl-N-phenylnitrone (4OPPN)

[0112] To a stirred mixture of 15.0 gm of 4-formyl-benzoyl chloride (1 equivalent, eq.) in 300 ml of chloroform, 2-aminoethanol (2 eq.) in chloroform (200 ml) was added dropwise at -10°C. 10.9gm solution in . After the addition, the resulting mixture was stirred at 25°C for 2 hours, and the resulting white precipitate was removed by filtration. Then, the filtrate was dried on a rotary evaporator to obtain 17.4 gm of a yellow liquid, 4-formyl-N-(2-hydroxyethyl)-benzamide.

[0113]Concentrated sulfuric acid (50 ml) was added dropwise to 4-formyl-N-(2-hydroxyethyl)-benzamide (17.4 gm) with stirring, and the mixture was heated at 100° C. for 1 hour. This solution was added dropwise to a mixture of sodium hydroxide (20%, 500ml) and chloroform (500ml) with stirring, keeping the temperature below 15°C by cooling. The organic phase is then separated off and dried. 6.3 gm of 4-(2-oxazolyl)benzaldehyde was colle...

Embodiment 2

[0116] Preparation of 4-(2-oxazolyl)-phenyl-N-methylnitrone (4OPMN)

[0117] To a stirred mixture of 4-formyl-benzoyl chloride (15.0gm, 89mmol) in chloroform (300ml) was added dropwise 2-aminoethanol (10.9gm, 178mmol) in chloroform (200ml) at -10°C. ) solution. After the addition, the resulting mixture was stirred at 25°C for 2 hours, then the white precipitate was filtered. The filtrate was dried by rotary evaporation to obtain 17 gm (88 mmol) of yellow liquid, 4-formyl-N-(2-hydroxyethyl)-benzamide (99% yield).

[0118] Concentrated sulfuric acid (50ml) was added dropwise to 4-formyl-N-(2-hydroxyethyl)-benzamide (17gm, 88mmol) with stirring, and the mixture was heated at 100°C for 1 hour. This solution was added dropwise to a mixture of sodium hydroxide (20%, 500ml) and chloroform (500ml) with stirring, keeping the temperature below 15°C by cooling. The organic phase is then separated off and dried. 6.3 gm (36 mMol) of 4-(2-oxazolyl)benzaldehyde was collected (41% yield...

Embodiment 3

[0121] Preparation of Phenyl-N-[4-(2-oxazolyl)phenyl]nitrone (P4OPN)

[0122] A solution of p-nitro-benzoyl chloride (185.6 mg, 100 mol) in 450 mL of hot benzene was added to a mixture of ethanolamine (63.5 g, 1.04 mol) in 1350 mL of water. Then 830 ml of 5% sodium hydroxide solution were gradually added. A white precipitate comprising p-nitro-N-(2-hydroxyethyl)benzamide formed which was filtered and dried. The dried p-nitro-N-(2-hydroxyethyl)benzamide powder weighed 196 g (0.93 mol) (93% yield).

[0123] Thionyl chloride (132 mL, 1.8 mol) was added dropwise to 196 g of p-nitro-N-(2-hydroxyethyl)benzamide powder with stirring. After a vigorous reaction, the resulting mixture was poured into 1 L of diethyl ether. An insoluble material comprising p-nitro-N-(2-chloroethyl)benzamide formed in ether which was filtered and dried to leave a white powder. 192 g (0.84 mol) of p-nitro-N-(2-chloroethyl)benzamide are obtained (90% yield).

[0124] 192 g of p-nitro-N-(2-chloroethyl)...

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Abstract

Dispersion of filler(s) in polymeric compositions are improved by the use of a polymer-filler coupling compound, Q-A-B, wherein Q comprises a dipolar nitrogen-containing moiety that can form a 1,3 dipolar addition to an unsaturated carbon-carbon bond; B is an oxazoline, thiazoline, alkoxysilane or allyltin moiety, and A is a linking atom or group that forms a bridge between Q and B.

Description

technical field [0001] This invention relates broadly to the dispersion of fillers in polymer compounds, and more particularly to the preparation of low hysteresis rubbers. Background technique [0002] In many industries it is often desirable to produce polymer compounds in which fillers are well dispersed. In the rubber industry, it is desirable to produce elastomeric compounds that exhibit reduced hysteresis when compounded with other ingredients such as reinforcing fillers and then vulcanized. The hysteresis of rubber refers to the difference between the energy applied to deform the rubber and the energy recovered when the rubber returns to its original undeformed state. Knowing that interactions between elastomeric molecules and reinforcing fillers affect hysteresis, it is believed that hysteresis and other physical properties of compounded elastomeric systems can be improved by ensuring good dispersion of reinforcing fillers throughout the elastomeric part. Elastomer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/14C07D277/10C08K5/32C08K5/3415C08L21/00C09K23/52
CPCC07D277/10C07D263/14C08K5/353C08K5/32C08L21/00C08L9/06
Inventor 福岛靖王威廉·赫根洛泽罗素·科赫荒木俊二
Owner BRIDGESTONE CORP
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