Amine dispersants

Details Amine dispersants Amine dispersants

2000-10-30

2003-06-24

Cain, Edward J. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

Reexamination Certificate

active

06583213

ABSTRACT:

The present invention relates to a dispersant having an amino group(s) which contains one or more poly(oxyalkylene carbonyl) chains derived from two or more different linear hydroxy-C
1-6
-alkylene carboxylic acids or lactones thereof wherein the amine is attached to an ethylenically unsaturated group by a Michaels addition reaction. These dispersants are particularly useful for dispersing particulate solids in an organic medium and in the preparation of dispersions and millbases for use in paints and printing inks.
EP 713,894 discloses dispersants containing amino groups and a polyoxyalkylene chain (hereinafter POAC chain) wherein the amino group is attached via a Michaels addition reaction to the POAC chain carrying an ethylenically unsaturated group. It is also disclosed that when lactones containing side chains are used, such as 4-methyl caprolactone and 2-methyl caprolactone, the resultant dispersants exhibit excellent compatability in resins and excellent solvent solubility. Examples are included where the dispersant is the Michaels addition product of polyethyleneimine and a hydroxyethylacrylate attached to a POAC chain which is a copolymer obtained by reacting 4-methyl caprolactone with &egr;-caprolactone.
It has now been found that more effective dispersants can be obtained without the need for expensive alkyl substituents in the caprolactone by using a POAC chain obtainable from two or more different and linear hydroxy-C
1-6
-alkylene carboxylic acids or lactones thereof.
According to the invention there is provided an amine dispersant containing one or more amino and/or imino groups, a poly(oxy-C
1-6
-alkylenecarbonyl) chain (hereinafter POAC chain) obtainable from two or more different linear hydroxy carboxylic acids or lactones thereof and a residue of an ethylenically unsaturated group wherein the amino and/or imino group is attached via the ethylenically unsaturated group, including salts thereof.
The POAC chain may be the residue of a block or preferably random polymer.
Preferably, the dispersant is obtainable from two different linear hydroxy-C
1-6
-alkylene carboxylic acids or lactones thereof.
Examples of suitable hydroxy carboxylic acids are glycolic, lactic, hydroxy valeric and hydroxy caproic acids.
Preferably, the POAC chain is obtainable from lactones such as &bgr;-propiolactone, &ggr;-butyrolactone, &dgr;-valerolactone and &egr;-caprolactone. POAC chains derivable from &dgr;-valerolactone and &egr;-caprolactone are much preferred.
According to a first aspect of the invention, the amine dispersant is a compound of formula 1
T—(CO—V—O)
m
—X—Z  (1)
wherein
T is hydrogen or a polymerisation terminating group;
(CO—V—O) represents a POAC chain obtained from two or more different linear hydroxy-C
1-6
-alkylene carboxylic acids or lactones thereof;
X is a bridging group which contains a residue of an ethylenically unsaturated group;
Z is an amino or imino group or a moiety containing an amino or imino group attached to X via the ethylenically unsaturated group; and
m is from 2 to 200.
In the dispersant of formula 1, the group T may be attached to the POAC chain (CO—V—O)
m
via an oxygen bridge or a carbonyl bridge. Thus, when T is attached to (CO—V—O)
m
via an oxygen bridge, the group —X—Z is attached via a carbonyl bridge and when T is attached to (CO—V—O)
m
via a carbonyl bridge then —X—Z is attached to (CO—V—O)
m
via an oxygen bridge.
Preferably, the POAC chain (CO—V—O)
m
is a chain of formula 2
wherein
A is —(CH
2
)
5
—;
B is —(CH
2
)
4
—; and
n+p is m.
The ratio of n to p is preferably from 10:1 to 1:10, more preferably from 10:1 to 1:1 and especially from 5:1 to 1:1.
It is also preferred that m is not less than 5 and not less than 10. Preferably, m is not greater than 100, more preferably not greater than 70 and especially not greater than 50.
When Z is or contains more than one amino or imino group there may be more than one POAC chain attached to Z via the group X.
The amino or imino group represented by Z or moiety containing the amino or imino group is preferably an amine or diamine, which may be aliphatic or aromatic and especially a polyamine or polyimine.
Examples of suitable amines are ethylenediamine, N,N
1
-dimethylethylenediamine, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 2,3-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine, N-aminoethylpiperazine, isophorondiamine, polyoxypropylenediamine, polyoxyethylenediamine, bis(4-amino-3-methyl dicyclohexyl)methane, diaminodicyclohexylmethane, bis(aminomethyl)cyclohexane, m-xylylenediamine, &agr;-(m-aminophenyl)ethylamine, &agr;-(p-aminophenyl)ethylamine, m-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulphone and norbornanediamine.
Examples of suitable polyamines are polyallylamine and polyvinylamine.
Examples of suitable polyimines are poly(C
2-4
)-alkyleneimine (hereinafter PAI) and especially polyethyleneimine (hereinafter PEI).
Preferably Z is derivable from a diamine, a polyamine and especially a polyimine.
When Z is a polyamine or polyimine, the amine dispersant may be conveniently represented by formula 3
wherein
X—*—*—X represents a polyamine or polyimine;
Y represents a POAC chain; and
q is from 2 to 2000.
Preferably, q is not less than 4 and especially not less than 10. It is also preferred that q is not greater than 1000 and especially not greater than 500.
It is also preferred that the weight ratio of the POAC chains represented by Y to the polyamine or polyimine represented by X—*—*—X is between 30:1 and 1:1, more preferably between 20:1 and 4:1 and especially between 18:1 and 8:1.
The number average molecular weight of the polyamine or polyimine is preferably from 500 to 600,000, more preferably from 1,000 to 200,000, even more preferably from 1,000 to 100,000 and especially from 5,000 to 100,000.
When T is a polymerisation terminating group it is preferably optionally substituted C
1-35
-hydrocarbyl which may be aromatic, alicyclic, heterocyclic or aliphatic which may be linear or branched, saturated or unsaturated. Preferably, T contains not greater than 20 carbon atoms and more preferably not greater than 10 carbon atoms.
Optional substituents in T include halogen, C
1-4
-alkoxy, ester (i.e. OCO), amide, thioether, urethane and ether groups. When T contains one or more ether groups it is preferably derivable from propylene and/or ethyleneoxide.
When T contains ester, amide or urethane groups, such groups may be made by linking together fragments of T which contain amino or hydroxy groups using, for example, dibasic acids or anhydrides or di-isocyanates. Examples of such linking agents are terephthalic acid, adipic acid, phthalic anhydride and toluene di-isocyanate.
As noted hereinbefore, T may be attached to the POAC chain via an oxygen atom or a carbonyl group in the POAC chain. Thus, the POAC chain is obtainable by reacting a monohydroxy compound T—OH with the hydroxycarboxylic acids or lactones thereof to give an alcohol containing the POAC chain and polymerisation terminating group (hereinafter TPOAC alcohol) of formula 4
TO—(CO—V—O)
m
—H  (4)
wherein T, (CO—V—O) and m are as defined hereinbefore.
Examples of monohydroxy compounds of formula T—OH are phenols and alcohols such as methanol, ethanol, butanol, octanol, decanol, lauryl alcohol and stearyl alcohol.
Alternatively, T may be the residue of a carboxylic acid T—COOH wherein the POAC chain is attached to T by a carbonyl group (hereinafter TPOAC acid) of formula 5
T—CO(O—V—CO)
m
—OH  (5)
wherein T, (CO—V—O) and m are as defined hereinbefore.
Examples of carboxylic acids are acetic, methoxyacetic, propionic, pentanoic, hexanoic, lauric, ricinoleic, stearic, 12-hydroxystearic, 12-hydroxydodecanoic, 5-hydroxydodecanoic, 5-hydroxydecanoic and 4-hydroxydecanoic acids.
The polymerisation terminating group may also contain the ethylenically unsaturated group. In one particularly preferred aspect of the invention the polymerisation terminating group contains both an ethylenically unsaturated group and a hydroxy group which reacts with the linear hydroxy C
1-6
-alky

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