Compositions: coating or plastic – Materials or ingredients – Pigment – filler – or aggregate compositions – e.g. – stone,...
Reexamination Certificate
2000-07-19
2001-09-04
Green, Anthony (Department: 1755)
Compositions: coating or plastic
Materials or ingredients
Pigment, filler, or aggregate compositions, e.g., stone,...
C106S410000
Reexamination Certificate
active
06284031
ABSTRACT:
TECHNICAL FIELD.
The present invention relates to novel compositions suitable for use as coatings comprising a) pigment and b) substituted amido phthalocyanines.The novel compositions are valuable for the delivery of excellent flow (non-flocculating) properties in ink and paint coatings as well as excellent heat stabilizing properties in thermoplastic resins.
BACKGROUND
The use of phthalocyanine (Pc) derivatives in pigment compositions is known. Typically phthalocyanine derivatives can be utilised in surface coating compositions such as inks, paints and plastics to impart improved flow behaviour (reduced flocculation); dispersibility; heat stability and the like.
GB949739 describes the use of non flocculating phthalocyanine preparations which contain as the relevant stabilising agent, substituted amino methyl phthalocyanine compounds having the formula:
Pc—(CH
2
NR
1
R
2
)
m
in which Pc is an m-valent phthalocyanine residue; R
1
and R
2
, independently, are hydrogen or an optionally substituted aliphatic residue, or the group —NR
1
R
2
is a heterocyclic residue, and m is 1, 2, 3 or 4.
In GB2009205, phthalocyanine compositions are disclosed comprising a) a phthalocyanine pigment b) a substituted amino methyl amido methyl phthalocyanine compound having the formula:
Pc—[CH
2
NHCO(CH
2
)
I
NR
1
R
2
]
n
in which Pc is the n-valent residue of a metal free or metal phthalocyanine; R
1
is hydrogen, alkyl, cycloalkyl, hydroxyalkyl, amino alkyl or aralkyl; R
2
is alkyl, cycloalkyl, hydroxyalkyl, amino alkyl or aralkyl; or R1 and R2 may be combined, with N-atom to form a 5- 6- or 7 membered heterocyclic ring; I is 1, 2, 3, or 4 and n is 1 , 2, 3, 4, 5, 6, 7 or 8; and c) a polyvalent metal salt of an anionic surface active agent
In EP 0087713 there are described phthalocyanine preparations, having improved colouristic properties and improved technical properties in application, comprising a) a finely diveded phtnalocyanine pigment; and b) a quaternised amino alkyl amido methyl phthalocyanine compound having the formula:
Pc—[CH
2
NHCO(CH
2
)
z
NR
1
R
2
R
3
]
n
(X)
n
in which Pc is an n-valent phthalocyanine residue, optionally containing up to two chlorine atoms; R
1
and R
2
independently, are C
2
-C
6
alkyl or C
2
-C
4
hydroxyalkyl; R
3
is C
1
-C
14
alkyl, C
2
-C
4
hydroxyalkyl, 2-hydroxy-3-chlorpropyl or benzyl; X is one equivalent of an anion; z is 1 or 2; and n is 1, 2, 3 or 4.
In GB695523, imido methyl and amido methyl phthalocyanine pigments are produced by reacting phthalocyanines with a hydroxymethylimide of formula:
in which R is a divalent radical, eg. methylene or a o-phenylene, resulting in the introduction, into the phthalocyanine molecule, of groups of formula:
in which R has its previous significance.
In EP 508 704 there are described substituted amido methyl derivatives having the formula B:
MPc(CH
2
NHCO—A)
n
B
in which M is hydrogen or a metal; Pc represents a phthalocyanine residue which is optionally further substituted by up to an average of one chlorine or bromine atom or of a sulphonic acid; n is a number ranging from 0.1 to 4.0, and A is C
3
-C
21
alkenyl, C
5
-C
8
cycloalkyl, C
7
-C
11
aralkyl, C
6
-C
10
aryl, a 5- or 6-membered heterocyclic residue or a fused heterocyclic system. These are formed by the reaction of an acid chloride with the aminomethyl phthalocyanine.
The present invention relates to pigment compositions comprising a) a pigment and b) an amido phthalocyanine compound having the general formula I:
MPc—(CONR
1
R
2
)
n
I.
in which Pc is a phthamocyanine ring which is optionally further substituted by up to an average of one chlorine or bromine atom or of a sulphonic acid, but which is preferably not further substituted; M is hydrogen or a metal such as Mg, Al, Ni, Fe, Zn, Pb, Sn or preferably, Cu capable of forming a metal phthalocyanine: n is a number ranging from 0.1 to 4.0, preferably from 1.0 to 3.0; R
1
and R
2
are independently selected from hydrogen, C
1
-C
20
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
12
aralkyl, C
6
-C
10
aryl, C
4
-C
6
alkyl amino alky, C
2
-C
20
aliphatic amine, C
2
-C
20
aliphatic amine acid salt, C
2
-C
20
alcohol, polyoxyalkylene, polyoxyalkylene amine.
The phthalocyanine compound b) can be readily synthesised by heating the carboxamide of phthalocyanine in the precense of amine acid/acid salts thus yielding substituted amido phthalocyanines of high purity. The novel process for the preparation of the phthalocyanine compound is the subject of a co-pending patent application. The amine/acid salts are denoted by formula II:
Wherein R and R
1
can be independently selected from the groups previously stated by formula 1, Z is the hydrochloride or the hydrogen sulphate salt of the amine.
It is an object of this present invention is to describe and propose several pigment compositions which are based on the synthesised derivatives defined by formula I. It is a further object of the present invention to provide coatings compositions such as ink, paint and plastics comprising the substituted amido phthalocyanine pigment compositons. The particular substituted amido phthalocyanine pigment compositions according to the present invention are valuable for the delivery of excellent flow (non-flocculating) properties of ink and paint coatings as well as excellent heat stabalizing properties in thermoplastic resins.
SUMMARY OF THE INVENTION
Accordingly, the present invention provides pigment compositions comprising of a) pigment and b) amido phthalocyanine derivative represented by general Formula I.
in which Pc is a phthalocyanine ring which is optionally further substituted by up to an average of one chlorine or bromine atom or of a sulphonic add, but which is preferably not further substituted; M is hydrogen or a metal eg. Mg, Al, Ni, Fe, Zn, Pb, Sn or preferably, Cu capable of forming a metal phthalocyanine: n is a number ranging from 0.1 to 4.0, preferably from 1.0 to 3.0; R
1
and R
2
are independently selected from hydrogen, C
1
-C
20
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
12
aralkyl, C
6
-C
10
aryl, C
4
-C
6
alkyl amino alkyl, C
2
-C
20
aliphatic amine, C
2
-C
20
aliphatic amine acid salt, C
2
-C
20
alcohol, polyoxyalkylene, polyoxyalkylene amine.
DESCRIPTION
The compositions according to the present invention include, as an essential feature an amido phthalocyanine of general formula I:
wherein as stated R
1
and R
2
are independently selected from hydrogen, C
1
-C
20
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
12
aralkyl, C
6
-C
10
aryl, C
4
-C
6
alkyl amino alkyl, C
2
-C
20
amine, C
2
-C
20
aliphatic amine acid salt, C
2
-C
20
alcohol, polyoxyalkylene, polyoxyalkylene amine.
Examples of C
1
-C
20
alkyl groups suitable for use herein include: methyl, propyl, butyl, hexyl, heptyl, dodecyl, hexcadecyl, octadecyl, tert-butyl, oleyl. Preferred alkyl groups R
1
R
2
are when R
1
=Hydrogen and R
2
is dodecyl, octadecyl, hexadecyl and oleyl.
Examples of C
5
-C
12
cyclo alkyl groups suitable for use herein include: cyclopentyl, cyclohexyl and cyclo-octyl, cyclohexyl being preferred when R
1
=Hydrogen.
Examples of C
7
-C
12
Aralkyl groups suitable for use herein include: benzyl or naphthylmethyl, benzyl being preferred when R
1
=Hydrogen.
Examples of C
6
-C
10
Aryl groups suitable for use herein include: phenyl or napthyl, with a preference for phenyl when R
1
=Hydrogen.
Examples of C
4
-C
6
alkyl amino alkyl groups suitable for use herein include: dimethylaminoethyl, dimethylaminopropyl, diethylaminopropylamine, dimethylaminopropyl being preffered when R
1
=Hydrogen.
Examples of C
2
-C
20
aliphatic amine groups suitable for use herein include: amino ethyl, amino propyl, amino butyl, amino pentyl, amino hexyl, amino heptyl, amino dodecyl amino-octyl. Preferred aliphatic amines are amino hexyl, amino heptyl, amino dodecyl and amino-octyl when R
1
=hydrogen.
Examples of the aliphatic amine acid salt groups suitable for use herein are as specified above however as the hydrochloride or the hydrogen sulphate. The pre
Ciba Specialty Chemicals Corp.
Crichton David R.
Green Anthony
LandOfFree
Pigment compositions containing substituted amido... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Pigment compositions containing substituted amido..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pigment compositions containing substituted amido... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2492787