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
2002-08-20
2004-09-07
Mullis, Jeffrey (Department: 1711)
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...
C525S063000
Reexamination Certificate
active
06787600
ABSTRACT:
The present invention relates to polyester dispersants comprising a polyamine or polyimine chain containing two or more different types of polyester chain attached to the polyamine or polyimine chains.
WO 94/21368 discloses a dispersant comprising a polyethyleneimine residue carrying a plurality of poly(carbonylalkyleneoxy) chains each chain containing a plurality of repeat units derivable from 6-hydroxyhexanoic acid and at least one other hydroxycarboxylic acid selected from ricinoleic acid, 12-hydroxystearic acid, 12-hydroxydodecanoic acid, 5-hydroxydodecanoic acid, 5-hydroxydecanoic acid and 4-hydroxydecanoic acid. These dispersants were shown to be particularly effective when dispersing pigments in non-polar solvents such as xylene.
WO 98/19784 discloses a dispersant which contains a polyester chain derived from optionally alkyl substituted &egr;-caprolactone and &dgr;-valerolactone attached via amide or salt groups to a polyamine or polyimine backbone chain such as polyallylamine or polyalkyleneimine, for example polyethyleneimine. These dispersants are particularly effective for dispersing pigments in polar organic liquids such as butanol and methoxy propylacetate.
EP 713 894 discloses dispersants which contain a polyester chain which is attached to a polyamine or polyimine backbone chain via a Michaels addition reaction. The polyester chain contains oxy-C
3-10
-alkylene carbonyl groups. These dispersants are effective for dispersing pigments in non-polar liquids such as xylenes and in polar organic liquids such as alcohols and ketones.
None of these prior art documents disclose or envisage dispersants wherein the polyamine or polyimine backbone chain contains different types of polyester side chains. It has now been found that such dispersants exhibit improved dispersion characteristics in both polar and non-polar organic liquids without significant deterioration of dispersion characteristics in the one type of organic liquid.
According to the invention there is provided a dispersant which comprises a polyamine or polyimine backbone chain containing side chains of two or more different types of polyesters chain wherein at least one type of polyester chain is derivable from one or more hydroxy carboxylic acids all of which contain a C
1-6
-alkylene group or lactone thereof and at least one other type of polyester chain derivable from one or more hydroxy carboxylic acids wherein at least one of the hydroxy carboxylic acids contains a C
8-30
-alkylene or C
8-30
-alkenylene group or lactone thereof, including salts of such dispersants. This is referred to hereinafter as The Dispersant.
Preferably the total amount of polyester chains attached to the polyamine or polyimine backbone is from 3:1 to 20:1 more preferably from 5:1 to 20:1, even more preferably from 10:1 to 15:1 and especially from 8:1 to 15:1 by weight of the polyamine or polyimine.
The polyester chain which is derivable from hydroxy carboxylic acids or lactones thereof all of which contain a C
1-6
-alkylene group is a poly(oxy C
1-6
-alkylene carbonyl) chain (hereinafter POAC 1). It may be linear or branched. The POAC 1 chain may be derivable from a single hydroxy carboxylic acid or lactone thereof or from different hydroxy carboxylic acids or lactones thereof.
Preferably, POAC 1 is derivable from hydroxy carboxylic acids or lactones thereof all of which contain a C
2-6
-alkylene group.
Examples of hydroxy carboxylic acids from which POAC 1 may be derived are glycolic acid, 6-hydroxy hexanoic acid and 5-hydroxy pentanoic acid. Examples of suitable lactones are optionally alkyl substituted ∈-caprolactone, optionally alkyl substituted &dgr;-valerolactone and &bgr;-propriolactone.
When the polyester chain of POAC 1 is branched it may be conveniently derived from alkyl substituted ∈-caprolactones. These may be made by oxidation of alkyl substituted cyclohexanone as described in WO 98/19784. Many of these alkyl substituted ∈-caprolactones are available as mixtures. The alkyl substituent is preferably C
1-6
-alkyl and especially C
1-4
-alkyl which may be linear or branched. Examples of alkyl substituted ∈-caprolactone are 7-methyl, 3-methyl, 5-methyl, 6-methyl, 4-methyl, 5-tert butyl, 4,6,6-trimethyl and 4,4,6-trimethyl substituted ∈-caprolactone. An example of an alkyl substituted &dgr;-valerolactone is &bgr;-methyl-&dgr;-valerolactone.
When POAC 1 is derivable from a single hydroxy carboxylic acid or lactone thereof it is preferably an alkyl substituted ∈-caprolactone and especially ∈-caprolactone itself.
However, it is preferred that POAC 1 is derivable from 2 or more different hydroxy carboxylic acids or lactones thereof and especially from two different hydroxy carboxylic acids or lactones thereof. When PAOC 1 is derivable from two different lactones, the lactones are preferably optionally alkyl substituted ∈-caprolactone and &dgr;-valerolactone and especially ∈-caprolactone and &dgr;-valerolactone. When POAC 1 is derivable from glycolic acid and one or more lactones, the lactone is preferably ∈-caprolactone.
The polyester chain which is derivable from one or more hydroxy carboxylic acids at least one of which contains a C
8-30
-alkylene or C
8-30
-alkenylene group, or lactone thereof, is hereinafter referred to as POAC 2. It may be linear or branched and preferably the alkylene or alkenylene group contains not greater than 24 and especially not greater than 20 carbon atoms. It is also preferred that the alkylene or alkenylene group contains not less than 10, more preferably not less than 12 and especially not less than 16 carbon atoms. Examples of suitable hydroxy carboxylic acids from which POAC 2 is derivable are ricinoleic acid, 12-hydroxy stearic acid, 12-hydroxy dodecanoic acid, 5-hydroxy dodecanoic acid, 5-hydroxy decanoic acid and 4-hydroxy decanoic acid.
In one preferred aspect of the invention, POAC 2 is derivable from a single hydroxy carboxylic acid which contains a C
8-30
-alkylene or C
8-30
-alkenylene group such as 12-hydroxy stearic acid or ricinoleic add.
In another preferred aspect of the invention, POAC 2 is derivable from two or more hydroxy carboxylic adds one of which contains a C
8-30
-alkylene or C
8-30
-alkenylene group and at least one hydroxy carboxylic acid which contains a C
1-6
-alkylene group, preferably a C
2-6
-alkylene group, or lactone thereof. Examples of POAC 2 derivable from two different kinds of hydroxy carboxylic acids or lactones thereof are those derivable from ricinoleic acid and optionally alkyl substituted ∈-caprolactone and those derivable from ricinoleic acid, optionally alkyl substituted ∈-caprolactone and &dgr;-valerolactone. When POAC 2 is derivable from optionally alkyl substituted ∈-caprolactone, the lactone is preferably unsubstituted.
In a particularly preferred class of dispersant, the dispersant contains only two different types of polyester chain, i.e. POAC 1 and POAC 2.
The polyester chains POAC 1 and POAC 2 may be attached to the polyamine or polyimine backbone chains via amide and/or salt linkages or they may be attached via a linkage which contains an ethylenically unsaturated group. In all these methods of attachment, the polyamine is preferably polyallylamine or polyvinylamine and the polyimine is preferably poly (C
2-6
-alkyleneimine) and especially polyethyleneimine. The polyimines may be linear but are preferably branched. Linear polyethyleneimines can be prepared by hydrolysis of poly (N-acyl) alkyleneimines as described, for example, by Takeo Saegusa et al in Macromolecules, 1972, Vol. 5, page 4470. The branched polyethyleneimines of differing molecular weights are commercially available from BASF and Nihon Shokubai. Polyallylamine and poly (N-alkyl) allylamines of differing molecular weights are commercially available from Nitto Boseki. Polyvinylamine of differing molecular weights are available from Mitsubishi Kasel. Poly (propyleneimine) dendrimers are commercially available from DSM Fine Chemicals and poly (amidoamine) dendrimers are available as “Starburst” dendrimers from Ald
Maxwell Ian Donald
Slater Lindsay Anne
Thetford Dean
Mullis Jeffrey
Pillsbury & Winthrop LLP
The Lubrizol Corporation
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