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1. 发明专利

GB679374A Process for the production of new copolymers of vinyl phenols 未知
公开(公告)号：GB679374A
公开(公告)日：1952-09-17
申请号：GB2217549
申请日：1949-08-26
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHANN JOSEPH PETER STAUDINGER , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02
摘要： Copolymers are made by copolymerizing a mono-vinyl phenol having at least one unsubstituted carbon in the o- or p-position with an acetal or semi-acetal of an unsaturated aldehyde, e.g. acrolein, a -alkyl-, a -aryl- and a -haloacroleins, with methyl, ethyl, iso- or n-propyl and n-butyl alcohols. Vinyl phenols specified are o-, m- and p-vinyl phenols, 3-vinyl-5-methyl-, 2-vinyl-3-methyl-, 3-vinyl-4-methyl-, 2-vinyl-4-methyl-, 2-methyl-4-vinyl- and 2-vinyl - 6 - methyl - phenols. A third monomer, e.g. styrene, a -methyl styrene, nuclear alkyl- or halo-styrenes, vinyl and vinylidene halides, acrylic, a -methacrylic and a -chloracrylic acids and their esters and nitriles and methyl vinyl ketone may be present. Polymerization is preferably effected in the presence of a peroxide, e.g. benzoyl or lauroyl peroxide, or perester catalyst, with or without heat or ultra-violet irradiation, in the presence or absence of a solvent for both the monomers and polymers, at low temperature using aluminium chloride as catalyst, or in emulsion, using persulphates with or without sodium sulphite as catalyst. The fusible soluble copolymers, e.g. in the form of filaments, foils, coatings or mouldings, may be hardened by hydrolysis with mineral acids, by heating above 100 DEG C. or by ultra-violet irradiation, whereby the aldehyde groups are liberated and cross-linking occurs. In an example, films of the copolymer, cast from a solution in benzene and methylated spirit, were converted to the infusible, insoluble state by heating at 130 DEG C. for 14 hours or by immersion in hydrochloric acid.

2. 发明专利

GB691042A Copolymers of vinyl phenols with drying oils 未知
公开(公告)号：GB691042A
公开(公告)日：1953-05-06
申请号：GB119049
申请日：1949-01-15
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , STANLEY ERWIN BRADSHAW , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02
摘要： Vinyl phenols, e.g. ortho-, meta- and paravinyl phenols and their methyl, ethyl, and propyl nuclear derivatives, are copolymerized with drying oils, e.g. chinawood, dehydrated castor, oiticica, tung, and linseed oils, which may be partially polymerized prior to copolymerization. Also present may be other polymerizable compounds containing the CH2=C

3. 发明专利

GB691041A Copolymerisation of vinyl phenols with polyhydric alcohol esters of alpha unsaturated alpha beta polycarboxylic acids 未知
公开(公告)号：GB691041A
公开(公告)日：1953-05-06
申请号：GB92449
申请日：1949-01-13
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02 , C08F283/01
摘要： Vinyl phenols, e.g. ortho, meta, and paravinyl phenols, and their methyl, ethyl, and propyl nuclear derivatives, are copolymerized with unsaturated alkyd resins derived from alpha, beta unsaturated polycarboxylic acids, the vinyl phenol constituting from 0.1 to 99.9 per cent of the monomer mixture. The unsaturated alkyd resins, which may be used in either the monomeric or partially polymerized state, are derived from polyhydric alcohols such as glycol, diethylene glycol, propylene glycol, butylene glycol, hexamethylene glycol, glycerol, pentaerythritol and their mixtures, and acids such as maleic, fumaric, itaconic, mesaconic, citraconic acids, or their anhydrides, or mixtures thereof. The alkyd resins may be prepared in the presence of zinc chloride and modifying agents such as butanol, decyl and octadecyl alcohols, phthalic, succinic, sebacic, butyric, stearic and abietic acids or anhydrides, castor oil, dehydrated castor oil and tung oil. Copolymerization may be carried out in bulk or aqueous dispersion, when the pH is preferably maintained below 7, with the aid of heat, actinic light, and catalysts such as lauryl, acetyl, crotonyl, benzoyl, tert.-butyl, and isopropyl benzene peroxides, tert.-butyl and isopropyl benzene hydroperoxides, hydrogen peroxide, alkali metal and ammonium persulphates and perborates, Friedel-Crafts catalysts, stannic chloride, hydrochloric and sulphuric acids, and acid-activated clays. The reaction may be terminated at a point short of gelation, and the copolymers stabilized by the addition of hydroquinone or metol. Hardening may be effected subsequently after the removal of the inhibitor, addition of more catalyst, or further heating. The copolymers may be used as a basis for moulding compositions, as rubbery sheets, and in the production of laminates and lacquers. Specification 691,037 is referred to.

4. 发明专利

GB691040A Copolymers of vinyl phenols with butadiene compounds 未知
公开(公告)号：GB691040A
公开(公告)日：1953-05-06
申请号：GB92249
申请日：1949-01-13
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02 , C08F36/04 , C08F212/14 , C08F236/04 , C08F240/00
摘要： Vinyl phenols, e.g. ortho-, meta-, and paravinyl phenols, and their methyl, ethyl and propyl nuclear derivatives, are copolymerized with butadiene type compounds, e.g. butadiene, isoprene, 2 : 3-dimethyl butadiene, and chloroprene. Polymerization may be carried out in bulk or aqueous dispersion with the aid of heat and light in the presence of catalysts such as benzoyl, acetyl, crotonyl, tert.-butyl, and isopropyl benzene peroxides, tert.-butyl, and isopropyl benzene hydroperoxides, tert.-butyl perbenzoate, hydrogen peroxide, alkali metal and ammonium perborates and persulphates, Friedel-Crafts catalysts, such as boron tri-fluoride, stannic chloride, hydrochloric and sulphuric acids, activated clays, and a combination of an oxidizing agent with a reducing agent such as sodium sulphite. When the reaction is performed in aqueous dispersion ethylene oxide polymer and sulphonated castor oil may be present, and the pH is preferably maintained below 7. The copolymers may be rendered infusible by vulcanization or by condensation with an aldehyde, and may be etherified. The products may be used as a basis for moulding compositions, adhesives and lacquers. Specifications 691,035, 691,036 and 691,037 are referred to.

5. 发明专利

GB691037A Production of pale coloured or colourless polyvinyl phenols 未知
公开(公告)号：GB691037A
公开(公告)日：1953-05-06
申请号：GB3048348
申请日：1948-11-24
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02
摘要： Vinyl phenols polymerized in bulk, in solution or in aqueous dispersion yield pale or colourless polymers if access of molecular oxygen is prevented during the reaction, e.g. by maintaining the mixture quiescent, reacting in absence of air or under an inert gas such as nitrogen, or in a completely filled vessel. The aqueous dispersion is at or below a pH of 7. Polymerization of the liquid monomers may be by heat or ultra-violet light in the presence of catalysts, e.g. acetyl, crotonyl, benzoyl, tertiary butyl and isopropyl - benzene peroxides, t.- butyl perbenzoate, and t.-butyl and isopropyl benzene hydroperoxides, hydrogen peroxide, and alkali-metal or ammonium persulphates. Low molecular weight material may be extracted from the polymer during a shredding process by solvents such as benzene, toluene, xylene, petrol ether, petrol, carbon tetrachloride, chloroform, trichlorethylene, di-ethyl ether or mixtures thereof. A small amount of ethanol may be first used to soften or dissolve the polymer. Specifications 409,132, 691,035 and 691,036 are referred to.

6. 发明专利

GB670502A Stabilisation of vinyl phenols and ethers thereof 未知
公开(公告)号：GB670502A
公开(公告)日：1952-04-23
申请号：GB3047848
申请日：1948-11-24
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C07C37/88
摘要： Vinylphenol, a vinylphenol ether, or a lower nuclear homologue thereof is stabilized by the addition of at least 0.01 per cent weight of ammonia, hydrazine or a substituted hydrazine, an aliphatic or aromatic amine, a saturated or unsaturated heterocyclic amine, or a hydroxyl derivative of any of the said amines. The expression substituted hydrazine means compounds based on hydrazine in which one or more hydrogen atoms have been replaced by an alkyl, aryl, or aralkyl group and the hydroxy derivatives of such compounds in which the hydroxyl group is not attached directly to a nitrogen atom of the hydrazine residue. Examples of suitable stabilizers include trimethylamine, aniline, p-aminophenol, b -phenylnaphthylamine, pyridine, quinoline, 8-hydroxyquinoline, piperidine, phenylhydrazine, o- and p-phenylenediamine, and metol; salts of the amines may be used when they are sufficiently soluble.

7. 发明专利

GB691043A New synthetic resins 未知
公开(公告)号：GB691043A
公开(公告)日：1953-05-06
申请号：GB411049
申请日：1949-02-15
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02 , C08F36/04 , C08F212/14 , C08F236/04 , C08F240/00
摘要： Vinyl phenols, e.g. ortho-, meta- and paravinyl phenols and their methyl, ethyl, and propyl nuclear derivatives, are copolymerized with cyclopentadiene and indene type compounds, e.g. cyclopentadiene, indene, coumarone and their methyl and ethyl derivatives, and naphtha fractions containing these substances. Copolymerization may be carried out in bulk or solution with the aid of heat, ultra-violet light, and catalysts such as hydrochloric and sulphuric acids, activated clays such as activated Fuller's earth, stannic chloride, boron trifluoride, phosphorus oxychloride, aluminium chloride, and organic peroxy compounds. The copolymers may be rendered infusible by heating with hexamethylene tetramine, cross-linked by condensing with aldehydes, or etherified. The copolymers may be used as a basis for lacquers or moulding powders. Specifications 691,035 and 691,036 are referred to.

8. 发明专利

GB691038A Copolymerisation of vinyl phenol type compounds with styrene type compounds 未知
公开(公告)号：GB691038A
公开(公告)日：1953-05-06
申请号：GB3069348
申请日：1948-11-26
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F16/02
摘要： Vinyl phenols or their lower nuclear homologues, e.g. methyl, ethyl or propyl substituted derivatives, are copolymerized with styrene compounds, e.g. styrene, monomethyl, ethyl and a -methyl p-methyl styrene and mono- and dichlorstyrenes; maleic acid esters and half esters of saturated aliphatic alcohols; acrylic compounds, e.g. methacrylic, a -ethyl, a -chlor, a -fluor acrylic acids, methyl and ethyl acrylates, ethyl and butyl methacrylates, methyl a -chlor-acrylate, acrylonitrile, methacrylonitrile, acrylyl chloride, and acryl- and methacrylamide; vinyl organic esters, e.g. formate, acetate, propionate, butyrate and stearate; vinyl ethers, e.g. methyl, ethyl, isopropyl, butyl, phenyl, tolyl, naphthyl, vinyl and propenyl ethers; vinyl ketones, e.g. methyl, ethyl, isopropyl, and butyl ketones; N-vinyl compounds, e.g. N-vinyl carbazole, pyrrole and piperidine; polymerizable allyl compounds, e.g. esters of allyl, methallyl, ethallyl, chlorallyl, crotonyl, cinnamyl, butene-1-ol-3, pentene-1-ol-3 and butadiene-2 : 3-ol-1, and polyhydric allyl alcohols with formic, phenoxy formic, acetic, lactic, butyric, glycollic, salicylic and oleic acids; or allyl ethers and allyl substituted aldehydes and ketones and their acetals and ketals. The reactive group in the latter may be chemically after-treated, and the vinyl ester copolymers may be hydrolysed partially or completely to produce vinyl alcohol units which in turn may be acetalized, e.g. with formaldehyde or hexamethylene tetramine. Copolymerization may be effected by heat or ultra-violet light with catalysts such as acetyl, crotonyl, benzoyl, tertiary-butyl, and isopropyl benzene peroxides, tertiary butyl perbenzoate, tertiary butyl and isopropyl benzene hydroperoxides, hydrogen peroxide, alkali metal or ammonium persulphates, Friedel-Craft catalysts, such as boron tri-fluoride, strong hydrochloric or sulphuric acid and acid-activated clay, or a Redox system with, e.g. sodium sulphite, in a homogeneous phase or in an aqueous dispersion of pH 7 or less. High molecular weight polymers may be separated by dissolving the initial resin in benzene, for example, and fractionally precipitating by an ethanol/petroleum ether mixture. The resins may be after-treated by cross-linking and/or etherification. Examples describe the homogeneous copolymerization of meta-vinyl phenol with styrene, ethyl acrylate, allyl caproate, diamyl maleate, ethyl vinyl ether containing divinyl ether, diallyl phthalate, and N-vinyl carbazole; of orthovinyl phenol with styrene; the copolymerization of meta-vinyl phenol with acrylonitrile, vinyl acetate or styrene in emulsions, in which sulphonated castor oil, polyethylene oxide, sodium sulphite and hydrogen peroxide are used; and the copolymerization of a solution of b -methyl styrene and m-vinyl phenol in toluene. Specifications 691,035, 691,036 and 691,037 are referred to.

9. 发明专利

GB691036A Etherification of vinyl phenol polymers or copolymers 未知
公开(公告)号：GB691036A
公开(公告)日：1953-05-06
申请号：GB3048248
申请日：1948-11-24
申请人： BRITISH RESIN PROD LTD , EDWARD MICHAEL EVANS , JOHN EDWARD SEAGER WHITNEY
IPC分类号： C08F8/00
摘要： Polymers and copolymers of ortho and meta vinyl phenols and their lower nuclear homologues are etherified by reaction with an unsaturated or saturated alkyl inorganic ester, e.g. dimethyl or diethyl sulphate, allyl or b -methallyl chloride, bromide or iodide but not fluoride. Copolymers with compounds such as butadiene hydrocarbons, chloroprene, styrene compounds, vinyl naphthalenes, acenaphthylene, N-vinyl pyridine, cyclopentadiene, vinyl and vinylidene halides, vinyl esters, acrylic esters, acrolein, or allyl compounds may be used. The polymer may be treated in a solution or dispersion in an alkaline polar medium, e.g. water or lower aliphatic alcohol or a non-polar medium, e.g. benzene or benzene-alcohol mixture, and in the latter case a quaternary ammonium hydroxide condensing agent is preferable. Films formed from a solution of the product in benzene containing tert-butyl hydroperoxide may be rendered insoluble on heating. In a modification the polymeric resin is treated with both an aldehyde and an etherifying agent, together or separately in one or two stages to yield a thermosetting resin which may be used as a moulding powder when compounded with fillers, plasticizers and lubricants, or used as a lacquer or adhesive when in a solution or dispersion. In examples poly-m-vinyl phenol, copolymers of m-vinyl phenol with styrene or methyl acrylate, and of o-vinyl phenol with styrene are etherified, the alkaline agents used being sodium hydroxide, methyl pyridinium hydroxide and tetramethyl ammonium hydroxide; and poly-m-vinyl phenol is reacted simultaneously with dimethyl sulphate and formaldehyde. Specifications 691,037, 691,038 and 691,040 are referred to.

10. 发明专利

GB669074A Process for the production of unsaturated phenolic compounds 未知
公开(公告)号：GB669074A
公开(公告)日：1952-03-26
申请号：GB1780049
申请日：1949-07-06
申请人： BRITISH RESIN PROD LTD , JOHN EDWARD SEAGER WHITNEY , EDWARD MICHAEL EVANS
IPC分类号： C07C37/00 , C07C37/50
摘要： Phenols and their ethers having at least one nuclear aliphatic hydrocarbon substituent of 3-28 carbon atoms, the two carbon atoms nearest the aromatic nucleus each bearing at least one hydrogen atom, are cracked in the vapour phase at an elevated temperature to convert the substituent into one with an a : b -double bond. A dehydrogenation catalyst of the kind used for dehydrogenating ethylbenzene (e.g. as in Specification 340,587, [Group III]) is preferably used, the reaction taking place at 400-800 DEG C.; a gaseous diluent such as steam, hydrogen, benzene, nitrogen or carbon dioxide may be present. The pressure may be atmospheric or higher or lower. When no catalyst is used, a solid heat-transfer material is preferably present. The preferred temperature range is 500-700 DEG C. with a contact time of 1-0.01 seconds. Depolymerization and replacement of nuclear carboxyl by hydrogen may occur simultaneously with the cracking, depending on the starting material used. The products may be separated by distillation or fractionation, followed by alkali extraction and selective precipitation with carbon dioxide or a stronger acid. A further fractionation may be carried out as the final step. In the examples: (1) cardanol from cashew nut shell liquid gives m-vinylphenol and non-phenolic bodies; (2) cardanol gives phenol, m-cresol, m-ethylphenol, m-vinylphenol and a higher-boiling residue; (3) cardanyl methyl ether gives m-methoxystyrene, m-vinylphenol and hydrocarbons; (4) p-n-hexylphenol gives p-vinylphenol and hydrocarbons. The process is applicable to alkyl-phenols and their alkyl and aryl ethers, such as those in coal tar and the components or distillates of cashew nut shell liquid including their hydrogenated derivatives. When a phenolic acid such as anacardic acid is used, decarboxylation takes place and the carbon dioxide evolved may function as the whole or part of the inert diluent.ALSO:Dehydrogenation catalysts comprise: (1) granular absorbent alumina on which is deposited 10 per cent by weight of calcium oxide; and (2) granular magnesite carrying 5.3 per cent of sodium vanadate. They are used for the cracking of alkyl-substituted phenols and their ethers to give alkenyl-substituted compounds with fewer carbon atoms.

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