Patent GB-992721-A (GB)
Title: Heterocyclic compounds and derivatives thereof
IPC: C07D265/06
Filed: 1961-06-28
Abstract: The invention comprises esters of acrylic and methacrylic acids and an N-hydroxyalkyl substituted heterocyclic nitrogen compound being (a) an N-hydroxyalkyl oxazolidine, (b) an N - hydroxyalkyl tetrahydro - 1,3 - oxazine or (c) a ring substituted derivative of said oxazolidine or tetrahydro-1,3-oxazine, preferably of formula <FORM:0992721/C2/1> where R represents hydrogen or a methyl group, m is 2 or 3, R1 when not joined to R2 represents hydrogen or a phenyl, benzyl, or a (C1-C12) alkyl group, R2 when not joined to R1 represents hydrogen or a (C1-C4) alkyl group and R1 and R2 when joined represent a tetra- or pentamethylene group, specifically oxazolidinyl ethyl methacrylate and acrylate, 3 - (y - methacryloxypropyl) - tetrahydro - 1,3-oxazine, 3 - (b  - methacryloxyethyl) - 2,2-pentamethylene-, and -2-methyl-2-propyl-oxazolidine, 2 - phenyl - 3 - (b  - methacryloxy-ethyl) oxazolidine, 2-methyl-3-(b -acryloxyethyl) oxazolidine, and 2-benzyl-3-(y-acryloxypropyl)-tetrahydro-1,3-oxazine. The esters are prepared by transesterifying an ester of acrylic or methacrylic acid with an N-hydroxyalkyl substituted heterocyclic compound, preferably under alkaline conditions with a tetra-alkyl titanate or an alkali metal alkoxide catalyst. They may be hydrolysed under acid conditions to open the heterocyclic nitrogen group to yield sec. amino group with a hydroxy-alkyl substituent. Specifications 518,057 and 579,698 are referred to.ALSO:Polymers of esters of acrylic and methacrylic acids and an N-hydroxyalkyl substituted heterocyclic nitrogen compound being (a) an N-hydroxyalkyloxazolidine, (b) an N-hydroxyalkyl tetrahydro-1,3-oxazine, or (c) a ring-substituted derivative of said oxazolidine or tetrahydro-1,3-oxazine preferably of formula <FORM:0992721/C3/1> where R represents hydrogen or a methyl group, m is 2 or 3, R1 when not joined to R2 represents hydrogen or a phenyl, benzyl or a (C1-C12) alkyl group, R2 when not joined to R1 represents hydrogen or a (C1-C4) alkyl group and R1 and R2 when joined represent a tetra- or a pentamethylene group (see Division C2) either alone or with comonomers e.g. vinyl acetate, acrylonitrile, acrylamide, methacrylamide, styrene, vinylidene chloride, vinyl chloride, vinyl laurate, N-methylolacrylamide, vinyl toluene and esters of acrylic and methacrylic acid with a C1-C18 alcohol are prepared by addition polymerization in solution or aqueous emulsion, with a free radical catalyst, such as an azo or peroxidic compound. Polymerization of the monomer in the presence of glue is also mentioned and the product may be used to flocculate suspended organic or inorganic material from aqueous media, as a filtration aid.  The polymers may also be hydrolysed, e.g. with acetic or phosphoric acid, to open the cyclic group to yield a secondary amine carrying a hydroxyalkyl group. Specifications 518,057 and 579,698 are referred to.ALSO:Lubricating compositions comprise a lubricating oil, e.g mineral or an ester oil such as dioctyl sebacate and an oil soluble copolymer derived from esters of acrylic and methacrylic acids and an N-hydroxyalkyl substituted heterocyclic nitrogen compound being (a) an N-hydroxyalkyloxazolidine (b) an N-hydroxyalkyltetrahydro - 1,3 - oxazine, or (c) a ring substituted derivative of said oxazolidine or tetrahydro-1,3-oxazine, preferably of formula <FORM:0992721/C4-C5/1> where R represents hydrogen or a methyl group, m is 2 or 3, R1 when not joined to R2 represents hydrogen or a phenyl, benzyl or (C1-C12) alkyl group, R2 when not joined to R1 represents hydrogen or a (C1-C4) alkyl group and R1 and R2 when joined represent a tetraor a pentamethylene group (see Division C2) copolymerized with oleophilic monomers such as one or more (C8-C18) alkyl acrylates or methacrylate e.g. derived from mixtures of lauryl or myristyl alcohols.  Examples describe the mixture of a mid-continent lubricating oil with a copolymer formed from oxazolidinylethyl acrylate or methacrylate, a mixture of lauryl and myristyl methacrylates, toluene, mercaptoethanol and dimethyl azo-diisobutyrate.  Specifications 518,057 and 579,698 are referred to.ALSO:Coating compositions for paper, textiles, leather, wood and metals comprise homo- or copolymers of esters of acrylic and methacrylic acids and an N-hydroxyalkyl substituted heterocyclic nitrogen compound being (a) an N-hydroxyalkyloxazolidine, (b) an N-hydroxyalkyltetrahydro-1,3-oxazine, or (c) a ring substituted derivative of said oxazolidine or tetrahydro-1,3-oxazine, preferably of formula <FORM:0992721/B1-B2/1> where R represents hydrogen or a methyl group, m is 2 or 3, R1 when not joined to R2, represents hydrogen or a phenyl, benzyl or (C1-C12) alkyl group, R2 when not joined to R1 represents hydrogen or an (C1-C4) alkyl group and R1 and R2 when joined collectively represent a pentamethylene or tetramethylene group (see Division C2).  The comonomers may be vinyl acetate, chloride or laurate, acrylonitrile, methacrylamide, acrylamide, N-methylol-acrylamide, vinyl toluene, esters (C1-C18) of acrylic or methacrylic acids, styrene, and vinylidene chloride. Examples describe the application of a copolymer of oxazolidinylethyl methacrylate with acrylonitrile and ethyl arcylate as a latex to paper and leather to give clear glossy coatings; the casting of a copolymer of oxazolidinylethyl acrylate, acrylonitrile and n-butyl acrylate to form a film; the application of a copolymer of 2-phenyl-3-(b -methacryloxyethyl) oxazolidine, vinyl toluene, vinyl acetate, and ethyl acrylate in latex form with copper phthalocyanine pigment and titanium dioxide to masonry, wood, plaster and metal panels to give flexible tough coatings.  The coating compositions may also contain epoxy resins.  Specifications 518,057 and 579,698 are referred to.ALSO:Non-woven fabrics e.g. carded rayons, are bonded with, and paper pulps may include monomers or copolymers of esters of acrylic and methacrylic acids and an N-hydroxyalkyl substituted heterocyclic nitrogen compound being (a) an N-hydroxyalkyl oxazolidine (b) an N-hydroxyalkyl tetrahydro-1, 3-oxazine or (c) a ring substituted derivative of said oxazolidine a tetrahydro-1, 3-oxazine, preferably of formula <FORM:0992721/D1-D2/1> where R represents hydrogen or a methyl group, m is 2 or 3, R1 when not joined to R2, represents hydrogen or a phenyl, benzyl or (C1-C12) alkyl group, R2 when not joined to R1, represents hydrogen or a (C1-C4) alkyl group and R1 and R2 when joined represent a pentamethylene or tetramethylene group (see Division C2).  Comonomers may be vinyl acetate, chloride and laurate, acrylonitrile, acrylamide, N-methylolacrylamide, vinyl toluene, esters (C1-C18) of acrylic or methacrylic acid, methacrylamide, styrene and vinylidene chloride and the polymers may be used in conjunction with poly-epoxides.  An example describes the application of a copolymer latex of 3-(y-methacryloxypropyl)-tetrahydro-1, 3-oxazine, N-methylol-acrylamide, acrylamide, vinyl toluene and ethyl acrylate to a non-woven fabric of carded rayon fibres to give 50% copolymer on the fibres.  A bonded fabric resistant to washing and perchloroethylene dry-cleaning was formed after drying and heating at 240 DEG F. for 30 minutes. 2-benzyl-3-(y-acryloxy-propyl)-tetrahydro-1, 3-oxazine and 2-methyl-3-(b -acryloxyethyl)-oxazolidine may also be used as above. Paper sheets may be prepared from bleached sulphite pulp which includes 2% of a polymer of oxazolidinyl ethyl methacrylate and show improved wet strength.  Specifications 518,057 and 579,698 are referred to.