Patent GB-1108261-A (GB)
Title: Novel dispersants for use in organic media
Inventor: FARKAS FERENC KAROLY
IPC: C09D7/45
Filed: 1963-08-01
Abstract: Novel dispersants for use in organic media correspond to the formula <FORM:1108261/C3/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links.  In a modification, the remaining R group or groups or the group R-C-C-R also provide(s) at least one additional component of the formula <FORM:1108261/C3/2> in which Ar and n are as defined above, the component being attached to one of two adjacent carbon atoms in said R group or R-C-C-R group, the other of the adjacent carbon atoms carrying a hydroxyl group, and the solvatable chain-like component containing at least 12 links per Ar group.  The solvatable component may be derived from polymers of hydroxy-fatty acids, epoxy resins, alkyd resins, polyalkylene oxides, polyamides, aminoplasts, polyurethanes, addition polymers and natural polymers. The group Ar may be a benzene, naphthalene, pyridine, quinoline or pyrrole residue and preferably contains one or more polar substituents.  The dispersants may be prepared by reacting a compound containing a carboxyl group with one containing an epoxy or a ,b -glycol group, one of said compounds also containing the Ar group and the other the solvatable R group; the esterification reaction can be catalysed by the use of a tertiary amine, e.g. dimethyl lauryl amine. Examples illustrate dispersants made by reacting (1) a methyl methacrylate-glycidyl methacrylate copolymer with p-nitrobenzoic acid (PNB); (2) the same copolymer as in (1) with each of the following acids: benzoic, o- and m-nitrobenzoic, 3,5-dinitrobenzoic, p-chlorobenzoic, p-aminobenzoic, p-toluic, a -naphthoic, p-methoxybenzoic, dimethyl sulphate-quaternized p-aminobenzoic, nicotinic, picolinic and p-nitrocinnamic acids; (3) epoxidized polybutadiene with PNB; (5) a pentaerythritol phthalate alkyd resin (modified with soya bean oil) with glycidyl p-nitrobenzoate; (8) a lauryl methacrylate-butyl methacrylate-glycidyl methacrylate copolymer with PNB; (9) polyhydroxystearic acid with glycidyl methacrylate, copolymerizing the ester product with vinyl toluene, styrene and glycidyl methacrylate, and reacting the copolymer obtained with PNB; (10) a lauryl methacrylate-butyl methacrylate-glycidyl methacrylate copolymer with dinitrobenzoic acid; (12) a liquid epoxy resin with PNB; (13) and (14) a lauryl methacrylate - butyl methacrylate - glycidyl methacrylate copolymer with PNB.  In Examples 1, 8, 9 and 10, the copolymers are obtained by solution polymerization of the corresponding monomers using benzoyl peroxide or azodiisobutyronitrile as initiator.  The Examples also illustrate the use of the products for dispersing various pigments in organic liquids and their application in paints; organic and inorganic (e.g. titanium dioxide, yellow iron oxide and carbon black) pigments are exemplified.ALSO:Pigments are dispersed in organic media with novel dispersants of the formula <FORM:1108261/C4-C5/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links. In a modification, the remaining R group or groups or the group R-C-C-R also provide at least one additional component of the formula <FORM:1108261/C4-C5/2> The solvatable chain-like component can be derived from a natural or synthetic polymer or from a fatty oil, fatty acid or hydroxy-fatty acid.  The pigment may be organic or inorganic; specified inorganic pigments are titanium dioxide, yellow iron oxide and carbon black.  Dispersion media specified are toluene/methyl isobutyl ketone, toluene, aliphatic/aromatic hydrocarbon solvent, aliphatic hydrocarbon solvent and white spirit. In Example 6 a dispersant is prepared by reacting (esterifying) polymerized linseed oil with glycidyl p-nitrobenzoate in the presence of dimethyl lauryl amine as catalyst, and used to disperse pigments in xylol, and the dispersion is contrasted with pigment dispersions in xylol containing the corresponding unmodified linseed stand oil.ALSO:The invention comprises novel dispersants for use in organic media of the formula <FORM:1108261/C2/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links.  In a modification, the remaining R group or groups or the group R-C-C-R also provide(s) at least one additional component of the formula <FORM:1108261/C2/2> in which Ar and n are as defined above, the component being attached to one of two adjacent carbon atoms in said R group or R-C-C-R group, the other of the adjacent carbon atoms carrying a hydroxyl group, and the solvatable chain-like component containing at least 12 links per Ar group.  The solvatable component may be derived from long chain fatty acids, e.g. lauric, myristic, palmitic, oleic, stearic or behenic acid, or a dimer, trimer &c. of a hydroxy fatty acid such as 12-hydroxystearic acid, or from a glyceride or an epoxidized natural oil. The group Ar may be a benzene, naphthalene, pyridine, quinoline or pyrrole residue and preferably contains one or more polar substituents. The dispersants may be prepared by reacting a carboxylic acid compound with an epoxy or a ,b -glycol compound, one of said compounds also containing the Ar group and the other the solvatable R group; the esterification reaction can be catalysed by the use of a tertiary amine, e.g. dimethyl lauryl amine. Examples illustrate dispersants made by reacting p-nitrobenzoic acid with epoxidized soya bean oil and with glycidyl oleate, and linseed oil monoglycerides with p-nitrobenzoyl chloride (in the presence of 2,6-lutidine).  These products are illustrated as dispersants for pigment compositions.ALSO:Particles of pigments, pesticides, blowing agents, and liquid particles of insoluble low molecular weight polymers are dispersed in organic media with the aid of novel dispersants of the formula:  <FORM:1108261/B1-B2/1> in which Ar is an aromatic group, n is 1 or 0, from 2 to 3 R groups are individually H, CH3 or C2H5, and the remaining R group or groups individually, or the remaining R-C-C-R group in combination, provide(s) a solvatable chain-like component of at least 12 links.  In a modification, the remaining R group or groups or the group R-C-C-R also provide at least one additional component of the formula: <FORM:1108261/B1-B2/2> The solvatable chain-like component can be derived from a natural or synthetic polymer or from a fatty oil, fatty acid or hydroxyfatty acid.  Dispersion may be effected by grinding, milling, emulsification or precipitation.