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Functionalized rubbers

A functionalized, rubbery polymer technology, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problems of unstable rubber over time, difficult removal of copper catalysts, low reaction temperature, etc.

Pending Publication Date: 2021-08-06
DYNASOL ELASTOMEROS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In summary, these methods involving new monomers for each functional group suffer from the obvious disadvantage of having two additional steps compared to conventional polymerization processes: the necessity of introducing a protecting group in the monomer and implementing a deprotection step, and the low reactivity Temperature / Polar Solvent Requirements
However, copper catalysts are very difficult to remove due to oxidation and side reactions on storage, and the rubber obtained is not stable over time

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1. Functionalization of SEBS with [N-(p-toluenesulfonyl)imino]phenyl iodane

[0143] This functionalization reaction was repeated 3 times with different amounts of reactants, see table below for more details.

[0144]The SEBS rubber polymer was dissolved in 1,2-dichloroethane, to which N-(p-toluenesulfonyl)imino]phenyliodinanes (PhINTs) and hydrogen tris(3,5-dimethyl- 4-bromopyrazolyl) borate silver catalyst (Tp* ,Br Ag).

[0145] The mixture was heated at 80° C. for 12 hours under nitrogen atmosphere. After cooling, methanol (100 mL to 200 mL) was added and the precipitated functionalized rubber was isolated by filtration and dried under vacuum. The isolated yield of the polymer was higher than 95%, the incorporation of NHTs units ranged from 1% w / w to 5% w / w (see table below), and was derived from the insertion of NHTs mainly into the tertiary sites of the rubber chain. The side -NHTs groups in the unit correspond.

[0146]

Embodiment 2

[0147] Example 2. Functionalization of unsaturated rubber with [N-(p-toluenesulfonyl)imino]phenyl iodane

[0148] In a variant of Example 1, and carried out at room temperature in cyclohexane as solvent, modified rubbers are obtained with a degree of incorporation of NHTs units in the range of 1% to 5% in >95% yield. In this case, the unsaturated rubber is modified upon formation of aziridine rings derived from the addition of NHTs units to the double bond of the unsaturated rubber.

Embodiment 3

[0149] Example 3. Functionalization of SEBS with ethyl diazoacetate

[0150] Cyclohexane solutions of rubber and catalyst at concentrations similar to those described in Example 1 were prepared. Ethyl diazoacetate (EDA) was dissolved in cyclohexane, and the solution was slowly added to the above mixture by means of an automatic addition system at room temperature for 12 hours. The mixture was then stirred for an additional hour before the solvent was removed under reduced pressure, redissolved in a minimum of THF and precipitated with methanol. After filtration and drying under vacuum, >95% of the mass was recovered. 1 H NMR studies show that CHCO 2 1% w / w to 5% w / w of the Et group is incorporated into the polymer chain, which now has a pendant -CH 2 CO 2 Et unit.

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Abstract

The present invention relates to a process for the functionalization of a rubber polymer comprising reacting the rubber polymer with at least one source of nitrene or carbene, in the presence of a catalyst of formula TpxAg, wherein Tpx represents a hydrotris(pyrazolyl)borate ligand. This process leads to selective rubber functionalization without secondary reactions such as chain scission or cross linking and produces functionalized rubbers with improved compatibilization properties. The invention also refers to the polymer produced therefrom and to uses of said polymer.

Description

technical field [0001] The invention relates to the field of functionalized rubber and a preparation method. More specifically, the invention relates to the field of chemical modification of hydrogenated and non-hydrogenated rubbers by metal-catalyzed addition of nitrogen and / or carbene groups and their use, especially in adhesives, in impact modification of plastics properties, compatibilization of plastic blends, asphalt modification, use in nanomaterials, and in particular, use in compounds for tires. Background technique [0002] Styrene-butadiene synthetic rubber comprises polymeric materials derived from styrene and butadiene. These rubbers may comprise randomly distributed polymer chains of styrene and butadiene monomers (SBR), but may also be materials comprising homopolymers and block copolymers. SBS triblock copolymers consist of a polymer chain of styrene monomer, followed by a polymer chain of butadiene monomer, followed in turn by another polymer chain of styr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F212/08C08L21/00C08C19/00
CPCC08C19/22C08C19/20C08F8/32C08F8/36B01J31/146C08L15/00
Inventor 塞尔焦·科罗纳加尔万佩德罗·何塞·普雷兹罗梅罗马里亚·德·马尔·迪亚兹雷克霍阿尔瓦罗·贝尔特兰马丁
Owner DYNASOL ELASTOMEROS
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