Aromatic dispersant composition

• US 10,113,031 B2
• Filed: 10/21/2014
• Issued: 10/30/2018
• Est. Priority Date: 11/01/2013
• Status: Active Grant

• Current Assignee: Lubrizol Advanced Materials Incorporated (Berkshire Hathaway Incorporated)
• Original Assignee: Lubrizol Advanced Materials Incorporated (Berkshire Hathaway Incorporated)
• Inventors: Thetford, Dean, Shooter, Andrew J., Jennings, Robert A.
• Primary Examiner(s): Loewe, Robert S
• Assistant Examiner(s): Nguyen, Ha S
• Application Number:
  US15/032,083
• Publication Number:
  US 20160264731A1
• Time in Patent Office: 1,470 Days
• Field of Search: None
• CPC Class Codes: C08G 65/22 Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• CPC Class Codes: C08G 65/2618 the other compounds containing nitrogen
• CPC Class Codes: C08G 65/333 containing nitrogen
• CPC Class Codes: C08G 65/33331 containing imide group
• CPC Class Codes: C08G 65/33341 aromatic
• CPC Class Codes: C09D 11/03 characterised by features other than the chemical nature of the binder
• CPC Class Codes: C09D 7/45 Anti-settling agents

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.

Claims

1. A polymer represented by Formula (1):

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 R¹=NO₂), 3-nitro-1,8-naphthalic imide (when one R¹=NO₂), 4-chloro-1,8-naphthalic imide (when one R¹=Cl), 3-sulpho-1,8-naphthalic imide (when one R¹=SO₃H), 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 (—

NH₂) 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 (—

NH₂) 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, hydroxycarboxylic acids, modified polyester isocyanate or any combination thereof to form pendant polyester chains, and optionally further reacting the hydroxyl end group of the polyesters chains derived from lactones and/or hydroxycarboxylic acids with modified polyether isocyanate to form block polyether/polyester pendant chains;

or

(d) reacting any hydroxyl and amino groups from step (b) 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.

9. The polymer of claim 8, 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, 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) 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

h) or any combination thereof.

10. A composition comprising a particulate solid, a polymer chain having at least one aromatic imide group, wherein the polymer is represented by a polymer of claim 1, and a medium selected from a polar organic medium, an aqueous medium, and a non-polar organic medium.

11. The composition of claim 10, wherein said medium comprises a polar organic medium.

12. The composition of claim 10, wherein said medium comprises an aqueous medium.

13. The composition of claim 10, wherein the composition is a millbase, paint or ink.

14. The composition of claim 10, wherein the particulate solid is a pigment or a filler.

15. The composition of claim 10, further comprising a binder.

16. The composition of claim 10, wherein the polymer is present in an amount ranging from 0.5 wt % to 30 wt % of the composition.

17. The composition of claim 10, wherein said medium comprises a non-polar organic medium.

18. The polymer of claim 1, wherein n is 2, and one or two R¹ groups on each Q ring is the electron withdrawing group NO₂.