cas 88-12-0, N-Vinyl-2-pyrrolidone | Articles data

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SYNTHESIS OF N-VINYL COMPOUNDS BY REACTING CYLIC NH-COMPOUNDS WITH ACETYLENE IN PRESENCE OF HOMOGENOUS CATALYST
Process to produce N-vinyl compounds by homogeneous catalysis, wherein acetylene is reacted with a cyclic compound comprising a cyclic compound having at least one nitrogen as ring member, bearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex comprising at least one phosphine as ligand (RuCat).
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Page/Page column 17; 20

(2021/06/26)

Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
Bienewald, Frank,Comba, Peter,Hashmi, A. Stephen K.,Menche, Maximilian,Rominger, Frank,Schafer, Ansgar,Schaub, Thomas,Sitte, Nikolai A.,Tuzina, Pavel
p. 13041 - 13055
(2021/09/18)

Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
The reaction of cyclic amides with acetylene under low pressure, using ruthenium-phosphine catalysts, afforded a broad variety ofN-vinylated amides including (azabicyclic) lactams, oxazolidinones, benzoisoxazolones, isoindolinones, quinoxalinones, oxazinanones, cyclic urea derivatives (imidazolidinones), nucleobases (thymine), amino acid anhydrides and thiazolidinone.
Semina, Elena,Tuzina, Pavel,Bienewald, Frank,Hashmi,Schaub, Thomas
supporting information
p. 5977 - 5980
(2020/06/04)

Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers
The production of monomers from bio-based platform chemicals shows great potential to reduce the chemical industry's demand for fossil resources. We herein present a two-step approach, which yields N-vinyl-2-pyrrolidone monomers from bio-based carboxylic acids, such as itaconic and levulinic acid. A highly active, heterogeneous palladium catalyst facilitating the reductive amidation of itaconic acid (TOF = 950 molPyr·molPd-surface-1 h-1) as well as the reductive amination of levulinic acid (TOF = 4000 molPyr·molPd-surface-1 h-1) was designed. Especially the reductive amidation of itaconic acid to 3- and 4-methyl-2-pyrrolidone was found to be structure sensitive. A clear trend between Pd particle size and catalyst activity could be shown by the synthesis of Pd/C catalysts with varying Pd particle sizes. The vinylation of the synthesized methyl-2-pyrrolidones with acetylene was tested using common industrial conditions (10-18 bar acetylene, 150 °C, KOH catalyst, no solvent). Similar to the industrial vinylation of 2-pyrrolidone, good yields of up to 80% N-vinyl-methyl-2-pyrrolidone were received. Therefore, and due to the excellent maximum yield of methyl-2-pyrrolidones in reductive amidation (95 mol%), the envisioned process can be a promising drop-in technology, directly replacing fossil resources in the production of an established monomer class. This journal is
Haus, Moritz O.,Hofmann, Jan P.,Konrad, Marc,Louven, Yannik,Palkovits, Regina
p. 4532 - 4540
(2020/11/02)

Extending the chemical product tree: A novel value chain for the production of: N -vinyl-2-pyrrolidones from biogenic acids
The sustainable production of polymers from biogenic platform chemicals shows great promise to reduce the chemical industry's dependence on fossil resources. In this context, we propose a new two-step process leading from dicarboxylic acids, such as succinic and itaconic acid, to N-vinyl-2-pyrrolidone monomers. Firstly, the biogenic acid is reacted with ethanolamine and hydrogen using small amounts of water as solvent together with solid catalysts. For effective conversion, the optimal catalyst (carbon supported ruthenium) has to hold the ability of activating H2 as well as (imide) CO bonds. The obtained products, N-(2-hydroxyethyl)-2-pyrrolidones, are subsequently converted in a continuous gas phase dehydration over simple sodium-doped silica, with excellent selectivity of above 96 mol% and water as the sole by-product. With a final product yield of ≥72 mol% over two process steps and very little waste due to the use of heterogeneous catalysis, the proposed route appears promising-commercially as well as in terms of Green Chemistry.
Haus, Moritz Otto,Louven, Yannik,Palkovits, Regina
supporting information
p. 6268 - 6276
(2019/12/03)

A-hydroxy ethyl pyrrolidine alkone dehydration N N-vinyl pyrrolidone preparing method (by machine translation)
The invention relates to a-hydroxy ethyl pyrrolidine alkone dehydration N preparation N-vinyl pyrrolidone method. The method of the invention comprises will contain an acidic component or alkaline component comprising an alkaline component of a gas or liquid and N-hydroxyethyl pyrrolidone mixed, the temperature 300-500°C, pressure 0.01-0.1 MPa with a gas-phase vhsv 10-5000h ?1 through the dehydration catalyst under the condition of a fixed bed reactor, N-vinyl pyrrolidone products obtained. The preparation method of this invention in conversion, selectivity, in service life are very clearly superior to the prior art. (by machine translation)
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Paragraph 0171; 0172; 0173; 0174

(2016/11/02)

Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals
The highly regioselective hydroselenation of N-vinyl lactams has been revealed to successfully afford the corresponding N,Se-acetals as Markovnikov adducts. In the case of terminal N-vinyl lactams, Markovnikov-selective hydroselenation proceeds efficiently in the absence of any catalyst (or additive), owing to the acidity of the selenols. In contrast, the self-promoted hydroselenation is inefficient with internal N-vinyl lactams. In the presence of palladium diacetate (Pd(OAc)2), however, the desired hydroselenation of internal N-vinyl lactams proceeds efficiently to afford the corresponding N,Se-acetals.
Tamai, Taichi,Yoshikawa, Megumi,Higashimae, Shinya,Nomoto, Akihiro,Ogawa, Akiya
p. 324 - 329
(2016/01/15)

Facile Preparation of N-Vinylisobutyramide and N-Vinyl-2-pyrrolidinone
A facile synthesis of N-vinylakylamides from commercially available N-vinylformamide and corresponding acyl chlorides was developed and exemplified by the preparation of N-vinylisobutyramide (NVIBA) and N-vinyl-2-pyrrolidinone (NVP) in high yields (80-89%). Both NVIBA and NVP are valuable monomers for water-soluble polymers with an array of applications in personal care, pharmaceutical, agricultural, and industrial products.
Tu, Siyu,Zhang, Chunming
p. 2045 - 2049
(2016/01/08)

A process to produce N-ethenyl-N-alkyl-alkylamides
A process to produce N-ethenyl-N-alkyl-alkylamide including the steps of reacting at least a N-monoalkyl-alkylamide with a reactant including 1,3-dioxolan-2-one in the presence of at least a catalyst to form an intermediate, and of decarboxylating said intermediate to synthesize N-ethenyl-N-alkyl-alkylamide.
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Paragraph 0064; 0065; 0066

(2015/02/25)

N-vinyl amide and used in the production of hydroxylapatite
PROBLEM TO BE SOLVED: To provide a method for producing an N-vinylamide which attains extremely high conversion and selectivity in the production of an N-vinylamide by dealcoholation reaction of N-(α-alkoxyalkyl)amide, and a catalyst used in the method.SOLUTION: According to the method, an N-vinylamide is produced by subjecting N-(α-alkoxyalkyl)amide to dealcoholation reaction in the presence of a surface-modified apatite catalyst prepared by surface-modifying an apatite represented by general formula (1) with a phosphoric acid compound. (In the formula, M is at least one member selected from the group consisting of Mg, Ca, Sr, Ba, Pb, Mn and Cd; Z is at least one member selected from the group consisting of P, As and Sb; X is at least one member selected from the group consisting of OH, F, Cl, Br, I and At; and 0≤y1).
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Paragraph 0041

(2016/12/26)

Method for Producing Bio-Based Homoserine Lactone and Bio-Based Organic Acid from O-Acyl Homoserine Produced by Microorganisms
The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.
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Paragraph 0236; 0237; 0238

(2014/10/16)

TFA-catalyzed C-N bond activation of enamides with indoles: Efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes
An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields.
Xu, Hai-Yan,Zi, You,Xu, Xiao-Ping,Wang, Shun-Yi,Ji, Shun-Jun
p. 1600 - 1605
(2013/02/25)

PROCESS FOR PREPARING N-VINYLPYRROLIDONE FROM LACTONE-FREE PYRROLIDONE
A process for preparing N-vinylpyrrolidone by reacting 2-pyrrolidone with acetylene, wherein the 2-pyrrolidone used as a starting material (referred to hereinafter as starting 2-pyrrolidone) comprises less than 1 part by weight of γ-butyrolactone per 100 parts by weight of 2-pyrrolidone.
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Page/Page column 2

(2011/02/26)

PROCESS FOR REMOVING BY-PRODUCTS FROM N-VINYLAMIDES
A process for removing by-products from N-vinylamide-rich product mixtures (crude N-vinylamide), which comprises performing an extraction of the crude N-vinylamide with an organic solvent as the extractant.
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Page/Page column 3

(2011/10/13)

PROCESS FOR ALKENYLATING CARBOXAMIDES
The present invention relates to a process for preparing N-(1-alkenyl)carboxamides of the formula I, which comprises reacting a carboxamide of the formula II with an alkyne of the formula III in the presence of a catalyst selected from among carbonyl complexes, halides and oxides of rhenium, manganese, tungsten, molybdenum, chromium and iron.
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Page/Page column 7

(2009/05/28)

Development of a new production process for N-vinyl-2-pyrrolidone
We describe the first continuous production process for N-vinyl-2-pyrrolidone (NVP). The starting materials are γ-butyrolactone (GBL) and monoethanolamine (MEA). The process consists of two stages: the synthesis of N-(2-hydroxy-ethyl)-2-pyrrolidone (HEP) from GBL and MEA, and the vapor-phase dehydration of HEP to NVP. The key features of this technology are the dehydration catalyst and the vapor-phase reaction system. The catalyst is of very simple composition, being alkali (or alkaline earth) metal oxides-SiO 2. Though its acid and base strengths are very weak, its catalytic performance is high. We presume that the excellent catalytic performance is due to the selective adsorption of HEP to the catalyst. Moreover, an IR spectroscopic study of the HEP-adsorbed catalyst indicated that the isolated silanol of the catalyst surface plays an important role. This account describes the progress made from the laboratory study to the industrial process, along with the experimental results and discussion.
Shimasaki, Yuuji,Yano, Hitoshi,Sugiura, Hideto,Kambe, Hideyuki
body text
p. 449 - 459
(2009/05/07)

Method for crystallizing N-vinyl-2-pyrrolidone
A method for purifying N-vinyl-2-pyrrolidone (NVP) is disclosed. The method comprises crystallizing NVP in the presence of added water to produce purified NVP crystals and a mother liquor, and then isolating the purified crystals. In a preferred method, 0.5 to 4 wt. % of water based on the amount of NVP to be purified is added, and the NVP crystals are washed with additional pure NVP, preferably NVP crystal melt, to give crystals having a purity greater than 99.99%. The method provides a fast, effective way to generate and isolate pure NVP in a single-stage crystallization.
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Page/Page column 3

(2008/06/13)

Process for making N-vinyl-2-pyrrolidone
A process for making N-vinyl-2-pyrrolidone (NVP) is disclosed. The process comprises dehydrating N-(2-hydroxyethyl)-2-pyrrolidone (HEP) in the presence of a catalyst and added water. Adding an effective amount of water into the dehydration process reduces the amount of N-ethyl-2-pyrrolidone (NEP) formed compared with the amount produced in the absence of the added water. Adding water can also sustain high conversions of HEP, minimize heavies formation, and improve selectivity to NVP. The process provides high-purity NVP and avoids a costly crystallization step.
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Page/Page column 4-6

(2008/06/13)

PRODUCTION METHOD OF N-VINYL-2-PYRROLIDONE
High-purity NVP can be produced by comprising at least two crystallization processes and supplying the mother liquor from the first crystallization process to the second crystallization process. Further, high-purity NVP can be obtained continuously and stably without plugging caused by depositing of crystals on the heat transfer surface of a crystallizer by controlling the water content in a feed NVP solution at the inlet of the crystallizer so as to be not lower than 0.7% by weight and not higher than 10% by weight.
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Page/Page column 14-25

(2008/06/13)

METHOD FOR STORING N-ALKENYL CARBOXYLIC ACID TERTIARY AMIDE
An N-alkenyl carboxylic acid tertiary amide having excellent storage stability is provided, by wetting the inner wall surface contacting with the vapor phase part of a storage container. An N-alkenyl carboxylic acid tertiary amide is stored under such condition that relation between temperature (T1) at the inner wall surface contacting with a vapor phase part of an storage container of an N-alkenyl carboxylic acid tertiary amide, and liquid temperature (T2) of an N-alkenyl carboxylic acid tertiary amide, satisfies that (T1) - (T2) is not lower than -10 (oC).
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Page/Page column 13

(2010/11/24)

Separating material
The present invention provides a separating material producable by a) providing a solid substrate, having amino-functional groups coupled to the substrate surface, b) covalently coupling of the amino-functional groups with a thermally labile radical initiator, c) contacting the substrate surface with a solution of polymerizable monomers under conditions, where thermally initiated graft copolymerization of the monomers takes place, to form a structure of adjacent functional polymer chains on the surface of the substrate. The present invention further provides a method for the production of a separating material by a) providing a solid substrate, having amino-functional groups coupled to the substrate surface, b) covalently coupling of the amino-functional groups with a thermally labile radical initiator, c) contacting the substrate surface with a solution of polymerizable monomers under conditions, where thermally initiated graft copolymerization of the monomers takes place, to form a structure of adjacent functional polymer chains on the surface of the substrate.
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(2008/06/13)

Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles
Matrix presented. Palladium(II) complexes catalyze the formation of enamides via the formal cross-coupling reaction between nitrogen nucleophiles and vinyl ethers. These vinyl transfer reactions proceed in good yields with amide, carbamate, and sulfonamide nucleophiles, and the optimal catalyst is (DPP)Pd(OCOCF3)2 (DPP = 4,7-diphenyl-1,10-phenanthroline).
Brice, Jodie L.,Meerdink, James E.,Stahl, Shannon S.
p. 1845 - 1848
(2007/10/03)

Production of N-vinyl pyrrolidone
N-vinyl pyrrolidone is produced by dehydration of N-hydroxyethyl pyrrolidone in the presence of an amorphous mixed oxide catalyst such as an amorphous Ca/Zn oxide catalyst.
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Page 1

(2008/06/13)

AnB block copolymers containing poly (vinyl pyrrolidone) units, medical devices, and methods
AnB block copolymers, wherein n is at least two, that include A blocks with poly(vinyl pyrrolidone) units and B blocks with urethane groups, urea groups, imide groups, amide groups, ether groups, ester groups, or combinations thereof, as well as medical devices and methods.
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(2008/06/13)

Method for production of aziridines and N-vinylamides
In the production of aziridines or N-vinyl amides respectively from an alkanolamine or an alkanolamide by the known method comprising a reaction step, a collecting step and/or a condensation step, a purifying step, and a recovering step, this invention is directed toward preventing formation of a solid substance in the vacuum pumps and the vacuum lines. The object of this invention is accomplished by performing the decompression at the purifying step and the decompression at the recovering step in mutually different decompression systems.
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Page/Page column 5

(2008/06/13)

Method for the production of n-alkenyl amides
A process for preparing N-alkenyl-amides by reacting the corresponding NH-amides with acetylenes in the liquid phase in the presence of basic alkali metal compounds and of a cocatalyst comprises using as the cocatalyst diols of the general formula (I) where X is branched or unbranched alkylene selected from the group consisting of where R1 to R6 are independently hydrogen or C1- to C4-alkyl; or branched or unbranched cyclic alkylene of 3 to 14 carbon atoms including 3 to 12 ring carbon atoms, their monoalkenyl ethers, their dialkenyl ethers or mixtures thereof.
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(2008/06/13)

Thermal desorption of covalently bound fullerene C60 from poly-N-vinylpyrrolidone films
Kinetics of formation of thermolysis products in heating of thin films of poly-N-vinylpyrrolidone and of poly-N-vinylpyrrolidone with covalently bound fullerene C60 was studied by thermal desorption mass spectrometry.
Pozdnyakov,Melenevskaya,Ratnikova,Ginzburg
p. 1965 - 1970
(2007/10/03)

Process for production of cyclic N-vinyl carboxylic acid amide
There is provided a process for producing a cyclic N-vinyl carboxylic acid amide stably in safety and low cost, using, as starting raw materials, a cyclic carboxylic acid ester and monoethanolamine both available inexpensively and easily. The process comprises subjecting a cyclic carboxylic acid ester and monoethanolamine to an intermolecular dehydration reaction (a first-step reaction) in a liquid phase to produce a cyclic N-(2-hydroxyethyl) carboxylic acid amide and then subjecting the cyclic N-(2-hydroxyethyl) carboxylic acid amide to an intramolecular dehydration reaction (a second-step reaction) in a gas phase in the presence of an oxide catalyst containing an alkali metal element and/or an alkaline earth metal element and silicon, to produce a cyclic N-vinyl carboxylic acid amide.
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(2008/06/13)

Catalyst for production of tertiary N-alkenyl carboxylic acid amide, and process for production of tertiary N-alkenyl carboxylic acid amide using said catalyst
The present invention provides a catalyst which is an oxide comprising silicon and at least one element selected from the group consisting of alkali metals and alkaline earth metals and which is used for gas-phase intramolecular dehydration of a tertiary N-(2-hydroxyalkyl) carboxylic acid amide to synthesize a tertiary N-alkenyl carboxylic acid amide. This catalyst enables continuous and efficient production of a tertiary N-alkenyl carboxylic acid amide from a tertiary N-(2-hydroxyalkyl) carboxylic acid amide without using any auxiliary raw material, and consequently allows for simple and safe production of a tertiary N-alkenyl carboxylic acid amide without generating any by-product (waste product) derived from the auxiliary raw material.
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(2008/06/13)

Process for production of N-vinyl compound
The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.
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(2008/06/13)

ELECTROCHEMICAL STUDIES ON HALOAMIDES. PART VIII. ELECTROSYNTHESIS OF N-(HALO)VINYLAMIDES
The electrochemical reduction of N-haloethylamides 1a,b-4a,b (X = OCOCH3, Cl) at a mercury pool cathode in HCON(CH3)2 (or CH3CN) - 0.1 mol dm-3 Et4NClO4 solution has been investigated. 2,2,2-trichloroethyl derivatives 1a-4a (X = OCOCH3, Cl) give rise to the corresponding N-(2,2-dichlorovinyl)amides 5a-8a in good to excellent yields, whereas in the case of N-(2,2-dichloroethyl)amides 1b-4b the course of the reduction depends on the nature of the substituent at N-Cα and/or of the amide moiety.Acetamides 1b (X = OCOCH3, Cl) yield a mixture isomeric 5b, but pyrrolidone derivatives 2b behave differently depending on X.If X = Cl the expected isomeric dehydrohalogenation products 6b are formed, whereas vinylpyrrolidone 6c, in addition to 6b, is formed from 2b, X = OCOCH3.High yields of 6c are attained by treatment of N-(2-chloroethyl)-2-pyrrolidone, 9, with the electrogenerated pyrrolidone anion.
Casadei, Maria Antonietta,Cesa, Stefania,Moracci, Franco Micheletti,Inesi, Achille
p. 457 - 462
(2007/10/02)

Hydrolytically degradable hydrophilic gels and the method for preparation thereof using N,O-dimethacryloylhydroxylamine as a cross-linking agent
The solution pertains to hydrolytically degradable hydrophilic gels consisting of the individual chains of hydrophilic polymer interconnected with crosslinks containing the structure unit STR1 The method for preparation of the hydrolytically degradable gels consists in subjecting hydrophilic monomers or their mixture to the radical polymerization or copolymerization, or to copolymerization with hydrophobic monomers, in the presence of a new compound--N,O-dimethacryloylhydroxylamine--as a crosslinking agent, and, if desired, in the presence of a solvent, whereas the amount of hydrophilic monomers is 50 to 99.8 molar percent related to all monomers present.
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(2008/06/13)

Hydrolytically degradable hydrophilic gels and the method for preparation thereof
The solution pertains to hydrolytically degradable hydrophilic gels consisting of the individual chains of hydrophilic polymer interconnected with crosslinks containing the structure unit The method for preparation of the hydrolytically degradable gels consists in subjecting hydrophilic monomers or their mixture to the radical polymerization or copolymerization, or to copolymerization with hydrophobic monomers, in the presence of a new compound - N,O-dimethacryloylhydroxylamine - as a crosslinking agent, and, if desired, in the presence of a solvent, whereas the amount of hydrophilic monomers is 50 to 99.8 molar percent related to all monomers present.
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(2008/06/13)

Method for conversion of ethylidene N,N'-bis-pyrrolidone into 2-pyrrolidone
A method for conversion of ethylidene N,N'-bis-pyrrolidone, a by-product of the vinylation of 2-pyrrolidone, into 2-pyrrolidone starting material. This method is carried out by heating the by-product at an elevated temperature for a predetermined period of time, and recovering the 2-pyrrolidone conversion product therefrom for recycle into the vinylation process.
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(2008/06/13)

Process for the preparation of N-vinyl lactams
The invention relates to the preparation of N-vinyl lactams having the formula STR1 wherein n is an integer having an value of from 1 to 3 in a one-stage, non-aqueous process which comprises reacting a lactam having the formula STR2 with acetylene under an acetylene partial pressure of from about 25 to about 125 psig. in the presence of an inert gas diluent and a catalyst having the formula STR3 wherein R1, R2 and R3 are all lower alkyl or alyl or one of R1, R2 and R3 can also be hydrogen and M is a metal selected from the group of cesium, potassium, sodium and lithium.
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(2008/06/13)

Colloidal metal dispersion, and a colloidal metal complex
There is disclosed a novel colloidal metal dispersion in which colloidal particles of a metal are protected by specific polymers including hydrazide polymers, acrylic ester polymers and acrylamide polymers. The colloidal metal dispersion is highly stable, and the colloidal metal particles protected by such specific polymers can be easily and strongly bound to various amino group-containing compounds to give stable colloidal metal complexes, which have a wide variety of uses, such as the use as a solid catalyst, the use for the treatment and diagnosis of various diseases, the use for studying tissues of living bodies, the use for including mutation of microorganisms, etc.
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(2008/06/13)

REACTIONS OF N-(TRIMETHYLSILYL) LACTAMS WITH CHLOROFORMIC ESTERS AND WITH α-HALO ETHERS
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Anisimova, N. A.,Kramarova, E. P.,Belavin, I. Yu.,Baukov, Yu. I.
p. 1631 - 1638
(2007/10/02)

Oxygen-permeable contact lens compositions, methods, and articles of manufacture
Copolymers of acrylic or methacrylic materials of known type and reacted with novel, silicone-substituted acrylic and methacrylic compounds so as to produce an oxygen-permeable plastic material which is uniquely suitable for manufacturing novel corneal contact lenses. The silicone materials include high molecular weight polysiloxanylalkylesters of acrylic and methacrylic acids, made from acrylic or methacrylic ester silanes containing one or more highly substituted siloxanyl groups. One such siloxane substituent, pentamethyldisiloxane, is prepared by a novel method. Certain of the substituted silanes are prepared using a novel compound, tris(trimethylsiloxy) acetoxysilane. The polymers made from the combination of novel and known monomers are highly permeable to oxygen and can be used to make lenses, including bifocal lenses, which are thick enough to be rugged, hard enough to provide dimensional stability, and optimum optical correction, and sufficiently permeable to oxygen to provide extended duration wearing capabilities. A number of novel monomers are disclosed. The polymers may be made from known monomers and individual novel monomers, or from the known monomers or mixtures thereof and mixtures of the novel monomers. The finished polymers may also include conventional additives such as wetting agents and cross-linking agents.
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(2008/06/13)