EP0292176A2
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EP
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Organo-metal compositions, preparation and use
Assignee: Imperial Chemical Industries Ltd
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Filing: 1988-05-09
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Granted: —
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Expires: 2008-05-09
Abstract
Abstract Complexes of a transition metal and a tetrasubstituted aromatic compound which contain at least two transition metal atoms. At least two of the substituents are -SH groups, the other two substituents being -SH, -OH and -NHR. The complexes are prepared by reacting the tetrasubstituted aromatic compound with a transition metal compound in the presence of a disubstituted aromatic compound. Depending on the relative proportions of the di- and tetra-substituted compounds, the resulting complex may contain more than one residue from the tetra-substituted compound and more than two transition metal atoms. The complexes possess infra-red absorbing properties which vary in dependence on the particular complex, the complexes with more than one residue from the tetrasubstituted compound absorbing radiation of longer wavelength. The compounds can be used to provide infra-red absorbing compositions, for example as a coating or inter-layer for glass. The complexes may be used together with one or more different infra-red absorbing materials. The tetra-substituted aromatic compound may be a tetra-thiol and this can be prepared from an aromatic compound containing at least four halogen substituents by reaction with an alkaline thiol compound in the presence of iron and sulphur in a polar solvent such as dimethyl formamide.
Inventors
- 👤 William Marshall Stark
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-31 01:44
CPC Classifications
C; C07; C07F; C07F15/00; C07C; C07C319/00; C07C319/02; C07F15/04; C07F15/045
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
112 words
A process for preparing an organo-metallic compound which comprises reacting a salt of a metal M with a compound of the formula: (HY)₂Ar(XH)₂ and a compound of the formula: HYRZH wherein: Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; and X, Y and Z may be the same or different.
Claim 2
Dependent Claim
112 words
A process for preparing an organo-metallic compound which comprises reacting a salt of a metal M with a compound of the formula: (HY)₂Ar(XH)₂ and a compound of the formula: HYRZH wherein: Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; and X, Y and Z may be the same or different.
Claim 3
Dependent Claim
27 words
A process as claimed in claim 1 wherein the compound of the formula: (HY)₂Ar(XH)₂ is benzene-1,2,4,5-tetrathiol; 3,6-dichlorobenzene-1,2,4,5-tetrathiol; naphthalene-1,2,5,6-tetrathiol; pyridine-2,3,5,6-tetrathiol; 3,6-difluorobenzene-1,2,4,5-tetrathiol; 1,4-dihydroxybenzene-2,5-dithiol; 1,3-dihydroxybenzene-4,6-dithiol; 1,2,4,5-tetraaminobenzene; 1,3-diaminobenzene-4,6-dithiol; 1,4-diaminobenzene-2,5-dithiol; or 2,6-dihydroxynaphthalene-1,5-dithiol.
Claim 4
Dependent Claim
29 words
A process as claimed in either claim 1 or claim 2 wherein the compound of the formula HYRZH is 3,4,5,6-tetrachlorobenzene-1,2-dithiol; naphthalene-1,2-dithiol; 2-hydroxynaphthalene-1-thiol; aniline-2-thiol; 4-butyl-1,2-diaminobenzene; quinoxaline-2,3-dithiol; 1,2-diphenylethylene-1,2-dithiol(cis); 1,3-dithiole-2-thione-4,5-dithiol; or 6-tert.butylphenol-2-thiol.
Claim 5
Dependent Claim
22 words
A process as claimed in any one of claims 1 to 3 wherein the salt of a metal M is nickel chloride.
Claim 6
Dependent Claim
17 words
A process as claimed in any one of claims 1 to 4 which include an oxidation step.
Claim 7
Dependent Claim
35 words
A process as claimed in any one of claims 1 to 5 wherein the molar proportions of the salt of the metal M, the compound (HY₂Ar(XH)₂ and the compound HYRZH are about 2:1:2 to 3:2:2.
Claim 8
Dependent Claim
19 words
A process as claimed in any one of claims 1 to 6 wherein a mixture of compounds is obtained.
Claim 9
Dependent Claim
81 words
A process for preparing a tetrathiol compound which comprises reacting an aromatic compound containing at least four halogen substituents attached to the aromatic ring with a metal hydrosulphide and sulphur in the presence of iron powder or an iron salt in a polar organic solvent wherein for each mole of the aromatic compound there are used at least 4 moles of the metal hydrosulphide, at least 0.5 moles of sulphur and at least 0.5 moles of iron powder or iron salt.
Claim 10
Dependent Claim
81 words
A process for preparing a tetrathiol compound which comprises reacting an aromatic compound containing at least four halogen substituents attached to the aromatic ring with a metal hydrosulphide and sulphur in the presence of iron powder or an iron salt in a polar organic solvent wherein for each mole of the aromatic compound there are used at least 4 moles of the metal hydrosulphide, at least 0.5 moles of sulphur and at least 0.5 moles of iron powder or iron salt.
Claim 11
Dependent Claim
31 words
A process as claimed in claim 8 wherein an iron complex is formed initially and this is then reacted with a nickel compound in the presence of a salt or base.
Claim 12
Dependent Claim
153 words
A composition which comprises at least two different compounds each of which is of the formula: [RYZ(MXYArXY) x MYZR] A wherein: A is a cation having a valency, and being in an amount, to give a neutral compound; Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; and x is an integer having a value of from 1 up to 10; and X, Y and Z may be the same or different; wherein at least one of A, Ar, R, M, X, Y, Z, R¹ and x is different in each compound.
Claim 13
Dependent Claim
153 words
A composition which comprises at least two different compounds each of which is of the formula: [RYZ(MXYArXY) x MYZR] A wherein: A is a cation having a valency, and being in an amount, to give a neutral compound; Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; and x is an integer having a value of from 1 up to 10; and X, Y and Z may be the same or different; wherein at least one of A, Ar, R, M, X, Y, Z, R¹ and x is different in each compound.
Claim 14
Dependent Claim
16 words
A composition as claimed in claim 10 wherein M is nickel in each of the compounds.
Claim 15
Dependent Claim
25 words
A composition as claimed in either claim 10 or claim 11 wherein X, Y and Z are all sulphur atoms in each of the compounds.
Claim 16
Dependent Claim
25 words
A composition as claimed in any one of claims 10 to 12 in which the value of x is different in each of the compounds.
Claim 17
Dependent Claim
164 words
A composition which comprises at least one compound of the formula: [RYZ(MXYArXY) x MYZR] A wherein: A is a cation having a valency, and being in an amount, to give a neutral compound; Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; x is an integer having a value of from 1 up to 10; and X, Y and Z may be the same or different; and at least one further material which is a compound having infra-red absorbing characteristics and is selected from compounds of the formula: [RYZMYZR]A , phthalocyanine derivatives, metal-aromatic amine complexes, metal dithiolethionedithiol complexes, and aminium or diimonium salts.
Claim 18
Dependent Claim
164 words
A composition which comprises at least one compound of the formula: [RYZ(MXYArXY) x MYZR] A wherein: A is a cation having a valency, and being in an amount, to give a neutral compound; Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; x is an integer having a value of from 1 up to 10; and X, Y and Z may be the same or different; and at least one further material which is a compound having infra-red absorbing characteristics and is selected from compounds of the formula: [RYZMYZR]A , phthalocyanine derivatives, metal-aromatic amine complexes, metal dithiolethionedithiol complexes, and aminium or diimonium salts.
Claim 19
Dependent Claim
152 words
A composition which is a plastics material, a printing or security ink, an adhesive or a paint and which contains at least one organo-metallic compound of the formula: [RYZ(MXYArXY) x MYZR] A wherein: A is a cation having a valency, and being in an amount, to give a neutral compound; Ar is an aromatic hydrocarbon or heterocyclic residue having at least four substituents; R is a hydrocarbon residue having at least two substituents; M is a transition metal; X is a sulphur atom or a group NR¹; Y is a sulphur atom, an oxygen atom or a group NR¹; Z is a sulphur atom, an oxygen atom or a group NR¹; R¹ is a hydrogen atom or a hydrocarbyl group; x is an integer having a value of from 1 up to 10; and X, Y and Z may be the same or different; or a composition as claimed in claim 14.
References Cited (Backward Citations)
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