Patent GB-947981-A (GB)
Title: New thiophene derivatives
IPC: C08K5/18
Filed: 1962-01-17
Abstract: The invention comprises thiophene derivatives of general formula: <FORM:0947981/C2/1> where R represents a thiophene residue in positions 2 and 5 to the oxazole rings; X1 a non-aromatic hydrocarbon residue containing at the most 22 carbon atoms and X2 a hydrogen or chlorine atom or a non-aromatic hydrocarbon residue with at the most 22 carbon atoms and X1 and X2 together, contain at least 4 carbon atoms; of general formula: <FORM:0947981/C2/2> where Y1 represents a saturated non-aromatic hydrocarbon residue with at the most 12 carbon atoms and Y2 a hydrogen or chlorine atom or a saturated, non-aromatic hydrocarbon residue with at the most 12 carbon atoms and Y1 and Y2 together contain at least 4 carbon atoms, and Z1 and Z2 may be identical or different and each represents a hydrogen atom or a hydrocarbon residue with 1 to 10 carbon atoms; of general formula: <FORM:0947981/C2/3> where U1 and U2 each represents a hydrogen atom or a methyl or phenyl group and W1 an alkyl group with at most 12 carbon atoms or a cyclohexyl group and W2 represents hydrogen or chlorine atom, or an alkyl group with at most 12 carbon atoms or a cyclohexyl group and W1 and W2 together contain at least 4 carbon atoms. The derivatives are prepared by reacting in a molecular ratio of 2:1, at an elevated temperature and preferably with a catalyst such as boric, p-toluene sulphonic and polyphosphoric acids and zinc chloride, at least one o-hydroxyaminobenzene with a dicarboxylic acid of formula HOOC-R-COOH where R represents a thiophene residue bound in positions 2 and 5, or a functional derivative thereof. Starting materials are listed and examples describe the preparation of compounds of formulae: <FORM:0947981/C2/4> and similar compounds in which (CH3)3C-, (CH3)CH-, (CH3)3C-CH2-C(CH3) 2-C12H25-, C2H5-, C3H7-, cyclohexyl-, are the substituents; <FORM:0947981/C2/5> <FORM:0947981/C2/6> compounds in which C2H5-, C3H7-, and C12 H25-, are substituents; <FORM:0947981/C2/7> <FORM:0947981/C2/8> and others. The products are optional brightening agents and may be used in structures of cellulose, lacquers e.g. of acrylic resins, cellulose ester or nitrocellulose; fibres e.g. of cellulose, polyamides, or polyolefines and films, foils, tapes and shaped structures of these and other polymeric materials. Specification 835,892 is referred to. ALSO: Optical brightening agents comprise 2:5-di-[benzoxazolyl-(21)] thiophenes of formula: <FORM:0947981/C3/1> where R represents a thiophene residue in positions 2 and 5 to the oxazole rings; X1 represents a non-aromatic hydrocarbon residue containing at most 22 carbon atoms and X2 a hydrogen or chlorine atom or a non-aromatic hydrocarbon residue with at most 22 carbon atoms and X1 and X2 together contain at least 4 carbon atoms (Division C2) The compounds may be used to brighten polyethylene, polyproplyene, polystyrene polyvinyl alcohol or polyvinyl acetate in the form of fibres, films foils, tapes and other shaped structures, and may be added before, during or after the polymerization.  Examples describe the treatment of polypropylene and polyethylene. fibres with 2:5 - di - [51 - t - butyl - benzoxazolyl - (21)] - thiophene and 2:5 - di - [51 - isopropyl-benzoxazolyl - (21)] - thiophene and an adduct of ethylene oxide and octadecyl alcohol, and trisodium phosphate; a composition of polyethylene with selected compounds alone or with titanium dioxide from which foils are calendered. Specification 835,892 is referred to. ALSO: Optical brightening agents comprise 2 : 5-di-[benzoxazolyl-(21)-] thiophenes of formula, <FORM:0947981/D1-D2/1> where R represents a thiophene residue in positions 2 and 5 to the oxazole rings; X, a non-aromatic hydrocarbon residue containing at most 22 carbon atoms and X2 a hydrogen or chlorine atom or a non-aromatic hydrocarbon residue with at most 22 carbon atoms and X1 and X2 together contain at least 4 carbon atoms (Division C2).  The compounds, in dissolved or divided state fluoresce and may be applied from aqueous or organic solvent bath containing a dispersing agent.  Fibres, films, foils tapes or shaped structures of synthetic materials such as cellulose esters, polyamides, polyolefines, polystyrene, polyvinyl alcohol, or polyvinyl esters are mentioned and examples describe the treatment of polypropylene or polyethylene fibres in a bath containing the compound with an adduct of ethylene oxide and octadecyl alcohol, and trisodium phosphate; and of acetylcellulose fibres with 2:5-di-[51-t-butyl-bezoxazolyl-(21)]-thiophene. Specification 835,892 is referred to.