Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2002-02-26
2003-11-04
Green, Anthony J. (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S031430, C106S031750, C106S031780, C106S031810, C106S493000, C106S496000, C106S499000, C008S661000, C008S662000, C564S281000
Reexamination Certificate
active
06641655
ABSTRACT:
The present application relates to fluidising agents for reducing the viscosity of dispersions of a particulate solid such as a pigment dispersed in an organic liquid using a dispersant and to millbases, paints and printing inks containing such fluidising agents.
U.S. Pat. No. 4,057,436 discloses a composition comprising a finely divided solid, a polymeric or resinous dispersant, a fluidising agent which is a substituted ammonium salt of a coloured acid wherein there are from 16 to 60 carbon atoms contained in at least 3 chains attached to the N atom of the substituted ammonium cation and an organic liquid. These fluidising agents are stated to give dispersions which exhibit lower viscosity at higher pigment loadings compared with similar dispersions which do not contain the fluidising agent. Examples of suitable amines and substituted ammonium salts which can be used to form the fluidising agents are tertiary amines and quaternary substituted ammonium salts such as N,N-dimethyloctadecylamine, cetyl-trimethyl ammonium bromide, didodecyl dimethyl ammonium chloride, dioctadecyl dimethyl ammonium chloride, N-cetyl pyridinium salts, N-cetyl piperidine, benzyldimethyloctadecyl ammonium chloride, octadecyl bis-(2-hydroxyethyl)amine and 3-(N-octadecyl-N-hydroxyethylamino)propyl-N
1
,N
1
-bis(2-hydroxyethyl)amine. The latter diamine is the only compound containing two tertiary nitrogen atoms which is disclosed. However, there are no specific examples of diamine salts of coloured acids and no advantage is envisaged for such compounds compared with those containing only the one tertiary nitrogen atom. The coloured acid used to make the fluidising agents include mono-, di- and tri-sulphonated copper phthalocyanine and azo and anthraquinone dyestuffs containing sulphonic acid and/or carboxylic acid groups. These fluidising agents were found to be particularly effective in dispersing a copper phthalocyanine pigment in an organic liquid. The copper phthalocyanine may be in crude or pigmentary form.
U.S. Pat. No. 4,461,647 discloses a fluidising agent which is a composition of disazo compounds containing at least 30% by weight of a water-insoluble disazo compound comprising a central divalent group free from acid and other ionic substituents linked through azo groups to two monovalent end groups characterised in that one end group, the first, is free from acidic and other ionic substituents and the other end group, the second, carries a single substituted ammonium-acid salt group. The substituted ammonium-acid salt group can be derived from dioctadecyldimethyl ammonium chloride or hydroxide, hexadecyltrimethyl ammonium bromide, octadec-12-anyldimethylamine and dodecyltrimethyl ammonium chloride.
GB 1356253 discloses benzidine pigment compositions which are mixtures of benzidine pigments which are free from water-solubilising groups and benzidine dyestuffs which contain two or more acid groups. The acid groups may be in the form of amine salts of diamines. These benzidine pigment compositions are stated to give improved colour strength and transparency when incorporated into printing inks compared with benzidine pigments which contain no acid groups. Benzidine pigments are obtained by tetrazotising benzidine derivatives which are free from water-solubilising groups and coupling with 2 moles of acetoacetarylamide or pyrazolone derivatives which are also free from water-solubilising groups. Benzidine dyestuffs containing two or more acid groups have similar structures but contain either two sulphonic acid groups in the benzidine derivative and/or acid groups in each of the coupling components.
It has now been found that fluidising agents which are diamine or diquaternary ammonium salts of coloured acids provide dispersions of pigments in organic liquids which exhibit lower viscosity at high pigment loadings when the diamine or diquaternary ammonium compound contains two or more nitrogen atoms compared with those amines and quaternary ammonium compounds which contain only one nitrogen atom.
According to the invention there is provided a fluidising agent which is a diamine and/or diquaternary ammonium salt of a coloured acid wherein the diamine or diquaternary ammonium cation contains two or more nitrogen atoms, except for fluidising agents which are diamine salts of an N-long chain alkyl alkylene diamine and a benzidine dyestuff containing two or more acid groups.
Preferably, the diamine or diquaternary ammonium cation is of formula 1
wherein
R is optionally substituted C
6-30
-alkyl or optionally substituted C
6-30
-alkenyl;
R
1
is hydrogen, optionally substituted C
1-30
-alkyl or C
2-30
-alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
R
2
, R
3
and R
5
are each, individually, optionally substituted C
1-6
-alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
R
4
is hydrogen, optionally substituted C
1-6
-alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted aralkyl;
X is C
1-12
-alkylene or C
2-14
-alkenylene; or
R
1
and R
3
together with the two nitrogen atoms to which they are attached and X form a ring; and/or
R
4
and R
5
together with the nitrogen atom to which they are attached form a ring.
In the cation of formula 1, the hydrogen atoms represented by R
1
and/or R
4
are derived from the coloured acid.
When R and R
1
is alkyl or alkenyl it may be linear or branched, but is preferably linear.
When R to R
5
are substituted, the substituent may be hydroxy, C
1-6
-alkoxy, cyano or halogen. However, it is preferred that R to R
5
are unsubstituted.
When R
1
is alkenyl it is preferably C
6-30
-alkenyl.
When R
1
to R
5
is aryl it is preferably phenyl and when R
1
to R
5
is aralkyl, it is preferably benzyl or 2-phenylethyl.
When R
1
to R
5
is substituted aryl or substituted aralkyl, the substituent is preferably hydroxy, C
1-4
-alkoxy, cyano or halogen.
When R to R
5
is substituted by halogen it is preferably bromine and especially chlorine.
When R
1
to R
5
is cycloalkyl it is preferably cyclopentyl or cyclohexyl.
When R
1
and R
3
together with the two nitrogen atoms to which they are attached and X form a ring, the ring is preferably piperazinyl.
When R
4
and R
5
together with the nitrogen atom to which they are attached form a ring, the ring is preferably piperidinyl, morpholinyl, piperazinyl or N—C
1-6
-alkylpiperazinyl.
When R
1
is optionally substituted C
1-30
-alkyl it is preferably optionally substituted C
1-6
-alkyl.
When R
1
to R
5
is C
1-6
-alkyl it may be linear or branched. Examples are ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-hexyl and especially methyl.
It is preferred that the compound of formula 1 contains two nitrogen atoms.
When R
1
and R
4
are both hydrogen, the compound of formula 1 is a diamine and it forms an amine salt with the coloured acid.
When R
1
and R
4
are other than hydrogen the compound of formula 1 is a diquaternary ammonium cation and forms a quaternary ammonium salt with the coloured acid.
Preferably X contains not less than 2 and especially not less than 3 carbon atoms. It is also preferred that X contains not greater than 12, more preferably not greater than 8 and especially not greater than 4 carbon atoms. Useful effects have been obtained when X is propylene.
In one preferred group of compounds of formula 1, R
1
and R
4
are both hydrogen and R
2
, R
3
and R
5
are each, independently C
1-6
-alkyl and especially methyl.
In a more preferred group of compounds of formula 1, R
1
to R
5
are each, independently, C
1-6
-alkyl and especially methyl.
Preferably, R contains not less than 8 carbon atoms. It is also preferred that R contains not greater than 20 and especially not greater than 18 carbon atoms.
The diamines and diquaternary ammonium compounds of formula 1 may be derived from natural products and as such may be available commercially as mixtures of diamines and diquaternary ammonium compounds. Particularly useful mixtures are those derived from tallow. I
Low Kristen Susan
McElhinney John Joseph
Murphy Laura Janette
Avecia Limited
Green Anthony J.
LandOfFree
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