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GB2118936A Expired / Lapsed GB ⏱️ 0.0 years remaining

Resinous sulphur or phosphorus containing salts their preparation and their use in coatings

Assignee: Novartis AG
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Filing: 1983-03-21
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Granted: —
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Expires: 2003-03-21
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Abstract

No abstract record available.

Inventors

  • 👤 Christopher George Demmer

Bibliographic Details

Application Number —
Jurisdiction GB
Data Source google_patents
Last Synchronized 2026-11-06 08:44
CPC Classifications
C; C08; C08G; C08G14/00; C08G14/02; C08G14/04; C08G14/06; C08G14/14; C09; C09D; C09D5/00; C09D5/44; C09D5/4419

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 510 words
Salts of the general formula f r7 q ' r9-ch- -ch-I -r6- -ch-I | -ch0- I oh I 0h p . cH-N-Rl-lYt-lslMXf r2 r m 13 GB 2 118 936 A 13 where R represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms, R1 represents an aliphatic, aromatic, or araliphatic di- or trivalent hydrocarbon group of 1 to 10 carbon atoms which may contain a further group 5 —Tt-(M+)„ 5 R2 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, one of R3 and R^ represents a hydroxyl group and the other represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, each R4, which may be the same or different, represents a hydrogen atom, a halogen atom, an 1 o alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, 1 o R5 represents an atom or a group bonded to a ring carbon atom which is ortho or para to the group R3 or R3 that represents a hydroxyl group, and is a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkenyl group of 2 to 4 carbon atoms, a group of formula —CH(Rz)OH, a group of formula —CH(R2)OR8, or a group of formula 15 —CH—N—R1—(—Yl-)s (M+)st 11 15 R2 R R6 represents the residue of a polyepoxide after removal of (m+p) 1,2-epoxide groups, each of the substituents R7, which may be the same or different, represents either a hydrogen atom or a covalent bond linked to the group R6 to form a cycloaliphatic ring which may be substituted by one or more aliphatic, cycloaliphatic and/or heterocyclic groups, 20 R8 represents either an alkyl group of from 1 to 6 carbon atoms or an alkoxyalkyl group wherein 20 the alkoxy group and the alkyl group each have from 1 to 6 carbon atoms, R9 represents the residue of a monohydric phenol, a secondary monoamine, or a monocarboxylic acid after removal of the hydrogen atom of the phenolic hydroxyl group, the carboxylic acid group, or the secondary amino group, 25 m represents 1,2,3, or 4, 25 n represents zero or 1, p represents zero or 1 such that (m+p) is at least 2 and at most 4, t represents 1 or 2, X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulphonyl group, 30 an oxygen or sulphur atom, or a valency bond, 30 M+ represents a hydrogen ion, a cation derived from an alkali metal, ammonia, an amine, including quaternary ammonium cations, or one valency of a polyvalent cation, with the proviso that at least 25% of the ions M+ represent a said cation, s represents 1 or 2, and. 35 Yt_ represents an anion of formula 35 0 II -S—0" II 0 0 0- II/ -P IV \ OH or 0 0" H/ v -P v \ 0"
Claim 2
Dependent Claim 510 words
Salts of the general formula f r7 q ' r9-ch- -ch-I -r6- -ch-I | -ch0- I oh I 0h p . cH-N-Rl-lYt-lslMXf r2 r m 13 GB 2 118 936 A 13 where R represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms, R1 represents an aliphatic, aromatic, or araliphatic di- or trivalent hydrocarbon group of 1 to 10 carbon atoms which may contain a further group 5 —Tt-(M+)„ 5 R2 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, one of R3 and R^ represents a hydroxyl group and the other represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, each R4, which may be the same or different, represents a hydrogen atom, a halogen atom, an 1 o alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, 1 o R5 represents an atom or a group bonded to a ring carbon atom which is ortho or para to the group R3 or R3 that represents a hydroxyl group, and is a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, an alkenyl group of 2 to 4 carbon atoms, a group of formula —CH(Rz)OH, a group of formula —CH(R2)OR8, or a group of formula 15 —CH—N—R1—(—Yl-)s (M+)st 11 15 R2 R R6 represents the residue of a polyepoxide after removal of (m+p) 1,2-epoxide groups, each of the substituents R7, which may be the same or different, represents either a hydrogen atom or a covalent bond linked to the group R6 to form a cycloaliphatic ring which may be substituted by one or more aliphatic, cycloaliphatic and/or heterocyclic groups, 20 R8 represents either an alkyl group of from 1 to 6 carbon atoms or an alkoxyalkyl group wherein 20 the alkoxy group and the alkyl group each have from 1 to 6 carbon atoms, R9 represents the residue of a monohydric phenol, a secondary monoamine, or a monocarboxylic acid after removal of the hydrogen atom of the phenolic hydroxyl group, the carboxylic acid group, or the secondary amino group, 25 m represents 1,2,3, or 4, 25 n represents zero or 1, p represents zero or 1 such that (m+p) is at least 2 and at most 4, t represents 1 or 2, X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulphonyl group, 30 an oxygen or sulphur atom, or a valency bond, 30 M+ represents a hydrogen ion, a cation derived from an alkali metal, ammonia, an amine, including quaternary ammonium cations, or one valency of a polyvalent cation, with the proviso that at least 25% of the ions M+ represent a said cation, s represents 1 or 2, and. 35 Yt_ represents an anion of formula 35 0 II -S—0" II 0 0 0- II/ -P IV \ OH or 0 0" H/ v -P v \ 0"
Claim 3
Dependent Claim 21 words
Salts as claimed in claim 1 wherein R6 represents a residue having an average molecular weight of from 1000 to 5000.
Claim 4
Dependent Claim 14 words
Salts as claimed in claim 1 or 2 in which (m+p) represents 2. 40
Claim 5
Dependent Claim 62 words
Salts as claimed in any previous claim wherein R represents a hydrogen atom and R1 represents 40 an alkylene or alkylidene group of 1 to 4 carbon atoms or an arylene, aralkylidene, or aralkylene group of 6 to 10 carbon atoms. 5. Salts as claimed in any previous claim which are of the formula 14 GB 2 118 936 A 14 wherein
Claim 6
Dependent Claim 54 words
5 R and R1 are as defined in either of claims 1 and 4, R2, R3, R^, R4, R5, R9, X, Y, M+, s, and t are as defined in claim 1, and R10 represents the residue of an aliphatic, cycloaliphatic, or aromatic diglycidyl ether or diglycidyl ester after removal of both glycidyl groups.
Claim 7
Dependent Claim 34 words
Salts as claimed in claim 5 wherein R10 is of formula VIII where R4 and X are as defined in claim 1 and q is zero or an integer of from 1 to 20.
Claim 8
Dependent Claim 17 words
Salts as claimed in claim 6 wherein q is an integer of from 2 to 10. 15
Claim 9
Dependent Claim 19 words
Salts as claimed in any previous claim in which R2 and R4 each represent a hydrogen atom. 1 5
Claim 10
Dependent Claim 176 words
Salts as claimed in claim 1, substantially as described in any of Examples 1 to 11. 10. A process for the preparation of water-soluble or water-dispersible salts which comprises reaction of a phenol-terminated resin of formula 20 where each R4 represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms or an alkenyl group of 2 to 4 carbon atoms, 20 15 GB 2 118 936 A 15 R6 represents the residue of a polyepoxide after removal of (m+p) 1,2-epoxide groups, each R7 represents either a hydrogen atom or a covalent bond which is linked to the group R6 to form a cycloaliphatic ring, R9 represents the residue of a monohydric phenol, a secondary monoamine, or a monocarboxylic 5 acid after removal of the hydrogen atom of the phenolic hydroxyl group, the secondary amino group, or 5 the carboxylic acid group, m represents 1, 2, 3 or 4, n represents zero or 1, p represents zero or 1, such that (m+p) is at least 2 and at most 4, and
Claim 11
Dependent Claim 214 words
10 X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulphonyl 10 group, an oxygen or sulphur atom, or a valency bond, with the proviso that at least one of the two carbon atoms ortho, or the one carbon atom para, to the carbon atom bearing the indicated phenolic hydroxyl group is unsubstituted, In the presence of a source of M+ ions, with an aldehyde of formula 15 R2CHO X 15 and an aminosulphonic or aminophosphonic acid of formula HN—R{—YH XI I R where R represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms, 20 R2 represents a hydrogen atom or an alkyl group of from 1 to 4 carbon atoms, 20 M+ represents a hydrogen ion, a cation derived from an alkali metal, ammonia, an amine, including quaternary ammonium cations, or one valency of a polyvalent cation, with the proviso that at least 25% of the ions M+ represent a said cation, R| represents an aliphatic, aromatic, or araliphatic di- ortrivalent hydrocarbon group of 1 to 10 25 carbon atoms which may contain a free phosphonic or sulphonic acid group of formula—S(:0)2OHor 25 —P(:0)(0H)2,and Y represents the residue of a sulphonic or phosphonic acid after removal of one hydrogen atom.
Claim 12
Dependent Claim 214 words
10 X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulphonyl 10 group, an oxygen or sulphur atom, or a valency bond, with the proviso that at least one of the two carbon atoms ortho, or the one carbon atom para, to the carbon atom bearing the indicated phenolic hydroxyl group is unsubstituted, In the presence of a source of M+ ions, with an aldehyde of formula 15 R2CHO X 15 and an aminosulphonic or aminophosphonic acid of formula HN—R{—YH XI I R where R represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms, 20 R2 represents a hydrogen atom or an alkyl group of from 1 to 4 carbon atoms, 20 M+ represents a hydrogen ion, a cation derived from an alkali metal, ammonia, an amine, including quaternary ammonium cations, or one valency of a polyvalent cation, with the proviso that at least 25% of the ions M+ represent a said cation, R| represents an aliphatic, aromatic, or araliphatic di- ortrivalent hydrocarbon group of 1 to 10 25 carbon atoms which may contain a free phosphonic or sulphonic acid group of formula—S(:0)2OHor 25 —P(:0)(0H)2,and Y represents the residue of a sulphonic or phosphonic acid after removal of one hydrogen atom.
Claim 13
Dependent Claim 24 words
A process as claimed in claim 10 in which R6 represents a residue having an average molecular weight of from 1000 to 6000. 30
Claim 14
Dependent Claim 15 words
A process as claimed in claim 10 or 11 in which (m+p) represents 2. 30
Claim 15
Dependent Claim 40 words
A process as claimed in any of claims 10 to 12 which is effected by heating the reactants in the presence of sufficient base at least partially to neutralise any free acid and optionally in the presence of a surfactant.
Claim 16
Dependent Claim 30 words
A process as claimed in claim 13 in which the base is sodium hydroxide, sodium carbonate, 35 potassium hydroxide, potassium carbonate, ammonia, triethylamine, triethanolamine, 2- 35 (dimethylamino)-2-methylpropan-1 -ol, or 2-(dimethylamino)ethanol.
Claim 17
Dependent Claim 145 words
Process according to any of claims 10 to 14 in which the aminosulphonic acid is sulphanilic acid, taurine, orthanilic acid or 2-aminobenzene-1,4-disulphonic acid, and the aminophosphonic acid is further of the formula Rl2yc-R11-NH2 40 r13 ^OH XII 40 o=p: ^OH where either R11 represents a covalent bond or an alkylene group of 1 to 4 carbon atoms, R12 represents an alkyl group of 1 to 4 carbon atoms, an aryl group of 6 to 10 carbon atoms, or a group of formula OH 45 0=P// XNI 45 \ OH and R13 represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or an aryl group of 6 to 10 carbon atoms, or 16 GB 2 118 936 A 16 R11 and R12, together with the carbon atom to which they are attached, form an aromatic ring in which case R13 is absent.
Claim 18
Dependent Claim 38 words
A process according to any of claims 10 to 15 in which 0.3 to 2.0 moles of the amino acid of formula XI are employed per mole of phenolic hydroxyl groups in the resin of formula IX. 5
Claim 19
Dependent Claim 33 words
A process according to any of claims 10 to 16 in which 1.1 to 4.0 moles of the aldehyde of 5 formula X are used per mole of the acid of formula XI.
Claim 20
Dependent Claim 16 words
A process according to claim 10, substantially as described in any of Examples 1 to 11.
Claim 21
Dependent Claim 14 words
Salts made by a process as claimed in any of claims 10 to 18.
Claim 22
Dependent Claim 105 words
Curable compositions comprising 100 parts by weight of a salt as claimed in any of claims 1 10 to 9 and 19, calculated on its solids content (as herein defined) and 2 to 200 parts by weight, 10 calculated on its solids content, of an aminoplast, a phenol-formaldehyde resin, or a blocked polyisocyanate, the aminoplast or phenol-formaldehyde resin having at least 2 groups of formula —CH20R14 XVI attached directly to an amidic nitrogen atom or atoms or directly attached to carbon atoms of a 15 phenolic ring, where R14 represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms. 15
Claim 23
Dependent Claim 15 words
Compositions according to claim 20, substantially as described in any of Examples 12 to 16.
Claim 24
Dependent Claim 37 words
A surface coated with a composition as claimed in claim 20 or 21, or with a salt of formula I as defined in any of claims 1 to 9 where R5 denotes a group of formula —CH(R2)0H.
Claim 25
Dependent Claim 19 words
A surface coating according to claim 22, substantially as described in any of Examples 12 to 20 17. 20
Claim 26
Dependent Claim 68 words
A method of coating a surface which comprises applying a composition as claimed in claim 20 or 21, or, in the absence of an aminoplast, a phenol-aldehyde resin, or a blocked polyisocyanate, a salt of formula I as defined in any of claims 1 to 9 where R5 denotes a group of formula —CH(R2)0H, and heating at from 100° to 275°C to cure the composition or the salt.
Claim 27
Dependent Claim 19 words
25 25. A method according to claim 24, substantially as described in any of Examples 12 to 17. 25
Claim 28
Dependent Claim 42 words
A surface coated by the method of claim 24 or 25. Printed for Her Majesty's Stationery Office by the Courier Press, Leamington Spa, 1983. Published by the Patent Office, 25 Southampton Buildings, London, WC2A 1 AY, from which copies may be obtained.

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