Patent GB-1069350-A (GB)
Title: Propynyl ethers and a process for the manufacture thereof
IPC: C07D317/44
Filed: 1966-02-11
Abstract: Paints, e.g. linseed oil based paints, contain an antibacterial and antifungal agent having the formula (I) Ar-Y-CH2-C­CR wherein Y represents an oxygen or sulphur atom, R represents a hydrogen or halogen atom and Ar represents a group of the formula <FORM:1069350/C4-C5/1> or, except where R represents a hydrogen atom, a group of the formula <FORM:1069350/C4-C5/2> in which groups X represent a halogen atom p represents an integer from 1 to 5 (the nitro group of the Formula Ia being in the ortho- or meta-position when p represents 1, Y represents an oxygen atom and R represents a hydrogen or iodine atom) and m and n represent integers of 1 to 4 according to the availability of position or positions.ALSO:The invention comprises compounds of the formula Ar-Y-CH2-C ­ CR wherein Y represents an oxygen or sulphur atom, R represents a hydrogen or halogen atom and Ar represents a group of the formula <FORM:1069350/C2/1> or, except where R represents a hydrogen atom, a group of the formula <FORM:1069350/C2/2> in which groups X represent a halogen atom, p represents an integer of from 1 to 5 (the nitro group in the group of Formula Ia being in the ortho- or meta-position when p represents 1, Y represents an oxygen atom and R represents a hydrogen or iodine atom) and m and n represent integers of from 1 to 4 according to the availability of position or positions; and their preparation by (a) reacting a compound of the formula Ar-YH with a 3-halo-propyne and, where required, halogenating the reaction product of the formula Ar-Y-CH2-C ­ CH or (b) condensing a compound of the formula Ar-YH with a 1,3-dihalo-propyne.  1-Iodo-3-bromo-propyne is prepared by reacting 3-bromo-propyne with iodine in the presence of sodium hydroxide.ALSO:Synthetic resinous materials, in particular vinyl chloride-acetate resins, contain an antibacterial and antifungal agent having the formula (I) Ar-Y-CH2-C­CR wherein Y represents an oxygen or sulphur atom, R represents a hydrogen or halogen atom and Ar represents a group of the formula <FORM:1069350/C3/1> or <FORM:1069350/C3/2> or, except where R represents a hydrogen atom, a group of the formula <FORM:1069350/C3/3> in which groups X represents a halogen atom, p represents an integer from 1 to 5 (the nitro group in the group of Formula Ia being in the ortho- or meta-position when p represents 1, Y represents an oxygen atom and R represents a hydrogen or iodine atom) and m and n represent integers of from 1 to 4 according to the availability of position or positions.ALSO:Pharmaceutical and disinfectant compositions, having antibacterial and antifungal activity, comprise a compound of the formula:  <FORM:1069350/A5-A6/1> wherein Y represents an oxygen or sulphur atom, R represents a hydrogen or halogen atom and Ar represents a group of the formula: <FORM:1069350/A5-A6/2> or <FORM:1069350/A5-A6/3> or, except where R represents a hydrogen atom, a group of the formula: <FORM:1069350/A5-A6/4> in which groups X represents a halogen atom, p represents an integer from 1 to 5 (the nitro group in the group of the formula Ia being in the ortho or meta-position when p represents I, Y represents an oxygen atom and R represents a hydrogen or iodine atom) and m and n represent integers of 1 to 4 according to the availablity of position or positions.  The above compounds may also be used as additives to cosmetics and in treating fibrous materials, leather, textiles, wood and paper.