The thermal dehydrochlorination and stabilization of poly(vinyl chloride)

Ayrey, G.; Head, B. C.; Poller, R. C.

doi:10.1002/pol.1974.230080101

Cited by 127 publications

(24 citation statements)

References 111 publications

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“…Next, 600 mL of CDCl 3 with internal toluene standard was added to the residue. The sample was analyzed by 1 The reaction on a preparative scale was carried out as described above using SnCl 2 (0.95 g, 5 mmol), 3-chloropropene (1.9 g, 25 mmol), PdMe 2 (phen) (79 mg, 0.25 mmol, 0.5 mol%) and CH 2 Cl 2 (25 mL). After the reaction mixture was heated for 30 h at 458C, it was cooled to room temperature and filtered.…”

Section: Resultsmentioning

confidence: 99%

“…By comparing the maximum yields and the yield after 120 h and by inspection of Figure 1, this feature is immediately apparent. The data in Table 1 show that the reactions catalyzed by the palladium complexes give higher yields of allyltin trichloride than those catalyzed by the analogous platinum complexes (entries [1][2][3][4][5][6][7][8]. Of the palladium complexes tested, PdMe 2 (phen) gave the highest yield (83%).…”

Section: Resultsmentioning

confidence: 99%

“…Evaporation of the solvent from the residue in vacuo resulted in 1.18 g of a slightly yellow colored oil. The oil was analyzed by 1 H NMR and found to contain allyltin trichloride in 95% purity along with some decomposition product (see text), corresponding to an 84% yield. In CH 2 Cl 2 .…”

Section: Resultsmentioning

confidence: 99%

“…When an excess of SnCl 2 was added to a solution of PdMe 2 (bipy) in CH 2 Cl 2 , the color of the solution turned orange instantaneously while deposition of palladium black became clearly visible. Analysis of the solution by 1 H NMR spectroscopy showed the absence of the initial palladium complex. Instead, the presence of the methylated product Me 2 SnCl 2 (d 1.22; 1 J HSn ¼84 Hz) 21 in the reaction mixture was observed.…”

Section: Mechanistic Aspectsmentioning

confidence: 99%

“…Monoalkyltin trihalides, RSnX 3 , (X¼Cl, Br, I; R¼alkyl) find application as precursors for PVC stabilizers, 1 as catalysts for polyurethane production and as precursors for the deposition of SnO 2 -coatings on glass. 2 They are produced industrially by a redistribution reaction, which is controlled by the stoichiometry of the reactants and which usually involves X¼Cl (Eq.…”

Section: Introductionmentioning

confidence: 99%

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Selective synthesis of monoorganotin trihalides: the direct reaction of allylic halides with tin(II) halides catalyzed by platinum and palladium complexes

Thoonen

Deelman²,

Koten

2003

Tetrahedron

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Abstract-The reaction of 3-haloalkenes (3-chloropropene, 3-bromopropene, 3-chloro-2-methylpropene, 1-chloro-2-butene) with SnX 2 (X¼Cl, Br) to form mono-allyltin trihalides, was catalyzed by several platinum and palladium complexes of the type MZ 2 L (M¼Pt, Pd; Z¼Me, Cl; L¼2,2 0 -bipyridine, 1,10-phenanthroline or dppe). The highest yield of allyltin trichloride was obtained for the reaction of 3-chloropropene with SnCl 2 catalyzed by PdMe 2 (phen) (83%) while the yield obtained with the other catalysts decreased in the order PdCl 2 (phen), PdCl 2 (bipy).PdMe 2 (bipy).PtCl 2 (phen).PtMe 2 (bipy).PtMe 2 (phen).PtCl 2 (bipy). Interestingly, PdCl 2 (PhCN) 2 and Pd(PPh 3 ) 4 had no activity at all. The yield of allyltin trichloride was not only dependent on the activity of the catalyst but also on the decomposition rate of the product in the presence of the catalyst. 3-Bromopropene gave 19% of allyltin tribromide when reacted with SnBr 2 . The other 3-haloalkenes did react but the resulting monoallylictin trihalides were not stable enough to produce significant yields. Reaction of both, benzyl chloride and chlorobenzene, led to catalyst decomposition. In addition, SnCl 2 catalyzed formation of polybenzyl was observed in the case of benzyl chloride. q

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Mechanistic Aspectsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective synthesis of monoorganotin trihalides: the direct reaction of allylic halides with tin(II) halides catalyzed by platinum and palladium complexes

Thoonen

Deelman²,

Koten

2003

Tetrahedron

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Synthesis and characterization of novel organotin monomers and copolymers and their antibacterial activity

Al‐Muaikel

Al-Diab

Al‐Salamah

et al. 2000

J. Appl. Polym. Sci.

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Two novel organotin monomers, (N-tri-n-butyltin) maleimide and m-acryloylamino-(tri-n-butyltin benzoate), were synthesized. Copolymerization of these two monomers with styrene was carried out in the bulk at 65°C using asobisisobutyronitrile as the free radical initiator. The monomers and copolymers were characterized by elemental analysis; the molecular weights of the copolymers were determined by GPC, solubility, IR, and 1 H-NMR spectral studies. The antibacterial activities of the synthesized organotin monomers and copolymers toward various types of bacteria were also reported.

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Heat Stabilizers

Mesch¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Heat stabilizers protect polymers from the chemical degrading effects of heat or uv irradiation. These additives include a wide variety of chemical substances, ranging from purely organic chemicals to metallic soaps to complex organometallic compounds. By far the most common polymer requiring the use of heat stabilizers is poly(vinyl chloride) (PVC). However, copolymers of PVC, chlorinated poly(vinyl chloride) (CPVC), poly(vinylidene chloride) (PVDC), and chlorinated polyethylene (CPE), also benefit from this technology. PVC is the most important class of halogenated polymers requiring these chemical additives. In normal operations, PVC resin is intimately mixed with the desired ingredients under high intensity shear mixing conditions to result in a homogeneous dry powder compound. The heat stabilizers can be either liquids or powders and are added early in the blending cycle to afford stabilizing action during this operation. Preheating the resin to about the glass‐transition temperature facilitates the adsorption of the liquid additives giving the final compound better powder flow properties and decreasing the bulk density. Post‐compounding operations, eg, extrusion pelletizing, can increase the overall heat history of the polymer, thus necessitating slightly higher levels of heat stabilizers to compensate for this. Organotin‐based heat stabilizers are the most efficient and universally used PVC stabilizers. These are all derivatives of tetravalent tin. The second most widely used class of stabilizers are the mixed metal combinations. These products predominate in the flexible PVC applications in the United States. The commercially important alkali and alkaline‐earth metals used in these stabilizer systems are based on the salts and soaps of calcium, zinc, magnesium, barium, and cadmium. Other organic compounds, such as phosphites, epoxides, polyols, and β ‐diketones, can also be added to enhance the performance further. Antimony mercaptan stabilizers are also used.

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The thermal dehydrochlorination and stabilization of poly(vinyl chloride)

Cited by 127 publications

References 111 publications

Selective synthesis of monoorganotin trihalides: the direct reaction of allylic halides with tin(II) halides catalyzed by platinum and palladium complexes

Selective synthesis of monoorganotin trihalides: the direct reaction of allylic halides with tin(II) halides catalyzed by platinum and palladium complexes

Synthesis and characterization of novel organotin monomers and copolymers and their antibacterial activity

Heat Stabilizers

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