Aromatic dispersant composition

Patent metadata

Field	Value
Publication number	US-10113031-B2
Application number	US-201415032083-A
Country	US
Kind code	B2
Filing date	Oct 21, 2014
Priority date	Nov 1, 2013
Publication date	Oct 30, 2018
Grant date	Oct 30, 2018

Abstract

The present invention relates to a composition containing a particulate solid, an organic or aqueous medium and a dispersant that may be a reaction product of an organic di or polyepoxide with a primary amine, aminoalcohol, amino acid, hydroxyacid or alcohol containing a fused or non-fused aromatic imide group. The invention further provides compositions for coatings, inks, toners, plastic materials (such as thermoplastics), plasticizers, plastisols, crude grinding and flush.

First claim

What is claimed is:

1. A polymer represented by Formula (1):

wherein dispersant of Formula (1) has a terminal and/or pendant imide group, wherein the side chain imide group is derived from an imide compound represented by Formula (1a):

wherein
R 1 is a substituent on Q ring in any position available for bonding to a substituent group and R 1 is independently represented by one or more of —H, or an electron withdrawing group selected from the group of: —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, halo, —NH 2 , and —OR′ or an electron releasing alkyl group, a is the total number of sites on the Q ring available for bonding a H, electron withdrawing groups, and electron releasing groups, when R 1 is said electron withdrawing group or said alkyl group, then the total number of electron withdrawing and alkyl groups is 1 or 2; M is H, a metal cation, NR′ 4 + , or mixtures thereof; R′ is —H, an optionally-substituted alkyl containing 1 to 20 carbon atoms, and the substituent is hydroxyl or halo or mixtures thereof;
Q is a fused or non-fused aromatic ring containing 4n+2 π-electrons, wherein n=1 or more, and Q is bonded to the imide group in such a way to form a 5 or 6 membered imide ring;
R 2 is a C 1 to C 20 hydrocarbylene group or mixtures thereof; R 2 optionally includes oxygen and/or nitrogen atoms wherein there is at least 2 carbon atoms per every oxygen or nitrogen of R 2 these would include ether, ester, and amide type linkages in R 2 ;
Pol is a residue of a diepoxide or polyepoxide further comprising at least one pendant side chain of one or more of:
a polyether,
a polyester,
a mixed polyether/polyester pendant side chains thereof,
a mixed polyester/polyether pendant side chains thereof,
or mixtures thereof,

the bond(s) between Pol and each W′ allows for one or more terminal and/or pendant side chain imide groups (as defined by w) to be attached to Pol at one or more locations on Pol and for each imide group to be attached to Pol by one or more bond (as defined by b);
W is any group capable of reaction with an epoxide group;
W′ represents amino, carboxylic acid and hydroxyl with the H missing and is a residue of the reaction of an amino, hydroxyl or carboxyl group, with a diepoxide or polyepoxide in a reaction forming a chemical bond between an amino, hydroxy, or carboxyl group with an epoxide; when b is 2 then one of the W′ is derived from a secondary amine reacted with said epoxide and optionally is in the R 2 linking group between the imide and the other W′ group, when b is 2 each W′ group is the same or different;
b is 1 or 2 and when b is 1, the imide group can either be terminal and attached to the Pol by one chemical bond when W is hydroxyl or carboxylic acid, or a pendant side chain when W is NH 2 and when b is 2 the imide group is a side chain attached to Pol by two chemical bonds;
d is 1, 2, or 3; this means that there is the possibility of 1 to 3 imide groups attached to R 2 at different carbon atoms of R 2 ; and
w is 1 or more.

2. The polymer of claim 1 , wherein n is 2, and Q is based upon 1,8-naphthalene anhydride, or 1, 2-naphthalene anhydride.

3. The polymer of claim 1 , wherein the fused aromatic ring is based on 1, 8-naphthalene imide, or 1, 2-naphthalene imide or mixtures thereof.

4. The polymer of claim 1 , wherein Q is based on a naphthalene imide selected from the group of: 4-nitro-1,8-naphthalic imide (when one R 1 =NO 2 ), 3-nitro-1,8-naphthalic imide (when one R 1 =NO 2 ), 4-chloro-1,8-naphthalic imide (when one R 1 =Cl), 3-sulpho-1,8-naphthalic imide (when one R 1 =SO 3 H), and mixtures thereof.

5. The polymer of claim 1 , wherein the polymer is obtained/obtainable by a process comprising addition polymerisation by reacting:
(a) at least one compound of Formula (1a) wherein when b=1, W is a primary amine (—NH 2 ) giving pendant imide groups and/or W is a hydroxyl or carboxylic acid, giving a terminal end imide group, and/or when b=2, W is a secondary amino group (—NH—), hydroxyl or carboxylic acid or mixtures thereof giving a pendant imide group,
(b) with one or more diepoxide and/or polyepoxide and at least one member of the group consisting of a monofunctional polyetheramine of number average MW 250-3500, based on a polyether comprising units of C 2-8 alkylene oxides or any combination thereof to give pendant polyether chains; and optionally
(c) in the presence of at least one member of a C 3-28 hydrocarbyl amine which is substituted; or at least one of an aminoalcohol; or a mixture thereof.

6. The polymer of claim 5 , wherein the polymer is prepared by further specifying one or more steps to further react any residual amino, hydroxyl, or epoxy groups including:
a) reacting any terminal amino groups present with isocyanates, lactones, hydroxycarboxylic acids, anhydrides, cyclic carbonates, or (meth)acrylates;
b) salification and/or reaction of any amino groups with mono or polycarboxylic acids, mineral acids, phosphorus and polyoxometallate containing acids or strong acids;
c) oxidation of any amino groups present to nitrogen oxides;
d) quaternization of any amino groups present with alkylating agents;
e) reacting any hydroxyl groups present with isocyanates, phosphoric acid, polyphosphoric acid, anhydrides or carboxylic acids;
f) reacting any terminal epoxide groups present with secondary amines or carboxylic acids;
g) reacting any residual primary hydroxyl and amino groups present with lactones, hydroxycarboxylic acids, modified polyester isocyanate or any combination thereof to form pendant polyester chains, and optionally further reacting the hydroxyl end group of the polyester chains derived from lactones and/or hydroxycarboxylic acids with modified polyether isocyanate to form block polyether/polyester pendant chains; or
reacting any hydroxyl and amino groups present with ethylene oxide, propylene oxide, butylene oxide, styrene oxide, modified polyether isocyanate or any combination thereof to form pendant polyether chains, and optionally further reacting the hydroxyl end group of the polyether chains derived from ethylene oxide, propylene oxide, butylene oxide, styrene oxide or mixtures thereof with modified polyester isocyanate to form block polyester/polyether pendant chains;
h) blending said addition polymer with a C 3-28 hydrocarbyl alkoxylate derived or obtainable from ethylene oxide, propylene oxide, butylene oxide, styrene oxide or mixtures thereof;
i) or any combination of a)-h) thereof.

7. The polymer of claim 6 , wherein the polymer is prepared by further specifying one or more steps to further react any residual amino, hydroxyl, or epoxy groups including at least one other step chosen from a), c), d), e), f) or g).

8. The polymer of claim 1 , wherein the polymer is obtained/obtainable by a process comprising addition polymerisation by reacting:
(a) at least one compound of Formula (1a) wherein when b=1, W is a primary amine (—NH 2 ) giving pendant imide groups and/or W is a hydroxyl or carboxylic acid, giving a terminal end imide group, and/or when b=2, W is a secondary amino group (—NH—), hydroxyl or carboxylic acid or mixtures thereof giving a pendant imide group,
(b) with one or more diepoxide and/or polyepoxide and at least one member of a C 3-28 hydrocarbyl amine which is substituted; or at least one of an aminoalcohol; or a mixture thereof; and
either or both of:
(c) reacting any residual primary hydroxyl and amino groups present from step (b) with lactones, h

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Thetford Dean
• Shooter Andrew J
• Jennings Robert A

Classifications

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G65/22 Primary

  Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring · CPC title

• C08G63/685

  containing nitrogen · CPC title

• C08G18/285

  Nitrogen containing compounds · CPC title

• C08G65/2618

  the other compounds containing nitrogen · CPC title