Derivatives of Synthetic Rubber

Endres, Herbert A.

doi:10.5254/1.3546709

Cited by 3 publications

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“…The essential points of these patents are based on the discovery of monobasic aluminum sulfite, Al2O3.2SO2.zH2O, as well-defined crystalline phase. The existence of this compound has been confirmed by Huber (8), Rosenkrantz and Hüttig (17), and Bartz (8). The technical progress claimed in the Goldschmidt patents consists of the practically complete precipitation, under certain conditions, of silica-free monobasic aluminum sulfite from silicacontaining leach liquors.…”

Section: Sulfite Processmentioning

confidence: 84%

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Chemical derivatives of synthetic isoprene rubbers

D'Ianni¹,

Naples²,

Marsh³

et al. 1946

Ind. Eng. Chem.

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A process for cyclizing synthetic polyisoprene in the same way as natural rubber was developed to give a product which, for many applications, is equivalent to cyclized natural rubber.GR-S does not react under the same conditions.A process for chlorinating synthetic polyisoprene was developed which gives a product similar to chlorinated natural rubber with respect to chlorine content, viscosity, thermal stability, solubility, and general utility in protective coatings and rubber-to-metal adhesives.GR-S cannot be satisfactorily chlorinated under the same conditions.Synthetic polyisoprene readily adds hydrogen chloride in a manner similar to natural rubber, whereas GR-S is practically unaffected. The product, however, does not have the excellent film-forming properties of Pliofilm.The striking similarity in chemical behavior of synthetic polyisoprene and natural rubber is attributed to the common chemical structure.The relative chemical inertness of GR-S is attributed to lack of a methyl group attached to the double bond.ATURAL rubber was the subject of intensive investigation with respect to its chemical reactions and the preparation of commercially useful derivatives. General reviews in this field have been written by Fisher (11), Schidrowitz (87), Jones (17), Sibley (89), Memmler (84), Daw-son and Schidrowitz (7), and Farmer (9). Before World War II several of these reaction products, such as rubber hydrochloride (Pliofilm), isomerized rubber (Pliolite), and chlorinated rubber (Parlón), had been marketed successfully.During the past five years drastic restriction of the commercial use of natural rubber for chemical derivatives prompted the study of synthetic rubbers for this purpose. Endres (8) recentlyreported on chlorinated and cyclized synthetic rubbers, with special emphasis on GR-S as the starting material.This paper deals particularly with derivatives of polyisoprene and other isoprene-containing synthetic rubbers which behave chemically very much like natural rubber because of the similarity in structure. It is shown that GR-S and other butadienecontaining synthetic rubbers, under the same conditions, are either nonreactive or behave differently.Because of its similarity to the natural rubber product, isomerized synthetic polyisoprene' has been designated Pliolite S-l. Chlorinated synthetic poly-isoprene 4s referred to as Pliochlor. CYCLIZED ISOPRENE POLYMERSThe formation of rubber isomers by-reaction with halides of amphoteric metals, such as stannous and stannic chlorides, aluminum chloride, boron fluoride, and chlorostannic acid, was reported by Bruson, Sebrell, and Calvert (4). The properties of such derivatives which render them useful as molding materials were described by Thies and Clifford (33) and by Jones and Winkelmann (18). Properties of Pliolite-rubber mixtures were described by Thies (38). Thermoprenes, which are reaction INDUSTRIALAND ENGINEERING CHEMISTRY

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Section: Sulfite Processmentioning

confidence: 84%

“…products of rubber and sulfuric acid or sulfonic acids, were investigated by 12), who considered them to be cyclic isomers of the rubber hydrocarbon. Endres (8) described the cyclization of GR-S at 160-180 °C. with stannic chloride in phenol, cresol, naphthalene, etc.…”

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Chemical derivatives of synthetic isoprene rubbers

D'Ianni¹,

Naples²,

Marsh³

et al. 1946

Ind. Eng. Chem.

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Etude de l'action des acides de lewis sur les polymères. Application au greffage de macromolécules sur les surfaces solides

Papirer

Morawski

Vidal

1975

Angew. Makromol. Chem.

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RESUME:La mise en presence d'une surface solide (oxyde metallique, noir de carbone ...) et de macromolecules comportant des carbocations, Crees par rhction avec un acide de Lewis, est suivie d'une insolubilisation importante du polymtre sur la surface solide. Les transformations physiques et chimiques subies par les polymtres hydrocarbonks sous I'action des acides de Lewis ont tout d'abord ete mesurkes.Des polymeres satures (polyethykne, polypropylene, polyisobutylene), le polystyrene, et des polymkres non satures (polybutadiene, polyisoprene, copolymere styrkne-butadiene, copolymtre isoprene-isobutylene) ont ete etudies.Les acides de Lewis agissent sur les polymeres soit en extrayant un ion hydrure, soit en additionant un proton sur une double liaison. Dans les deux cas, il se forme un cation polymerique dont I'evolution depend principalement de sa stabilite, de la proximite sterique et de la nature des groupements lateraux fixes sur le squelette.Avec les polymtres insatures, la quantite de plymere fix6 est superieure A la quantite necessaire A la formation d'une monocouche de macromoltcules sur la surface solide.Elle depend de la concentration en cations polymeriques de la solution et de I'accessibilite de I'acide de Lewis aux fonctions chimiques superficielles du solide. SUMMARY:The interaction between a solid surface (metal oxides, carbon blacks ...) and macromolecules carrying a carbenium ion formed by a Lewis acid attack, results in a significant insolubilization of the polymer on the surface. Physical modifications of hydrocarbon polymers under the action of Lewis acids have been followed. Saturated (polyethylene, polypropylene, polyisobutylene), unsaturated (polybutadiene, polyisoprene, styrene-butadiene and isoprene-isobutylene copolymers) and styrene polymers have been investigated.Lewis acids generally extract a hydrid ion or add a proton to the double bond of a polymer. In both cases, a polymeric cation is formed: its evolution depends essentially on its stability and on the vicinity of chemical groups on the backbone of the polymer. 91 E. Papirer, J.-C. Morawski et A. VidalThe carbenium ion reacts with the surface hydroxyl groups. The amount of polymer irreversibly fixed on the solid surface exceeds the one required for the formation of the monolayer. It depends both on the concentration of polymeric cations and on the accessibility of the surface groups to the Lewis acid.

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Polyenes

Cooper¹

1963

The Chemistry of Cationic Polymerization

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Derivatives of Synthetic Rubber

Cited by 3 publications

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Chemical derivatives of synthetic isoprene rubbers

Chemical derivatives of synthetic isoprene rubbers

Etude de l'action des acides de lewis sur les polymères. Application au greffage de macromolécules sur les surfaces solides

Polyenes

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