Sugar-based, environmentally-friendly pigment and mineral dispersants

Abstract

Pigment dispersion compositions within a liquid medium, ethylene oxide and 1,4-dioxane free, with low viscosity and moderate to high pigment concentrations using derivatized alkyl polyglucosides and / o

Description

[0002] Pigments have been manufactured and used for hundreds of years. Before being used they are typically dispersed in a liquid medium for ease of application. Traditionally a type of oil or water has been used as the liquid medium, and the problem of dispersing certain pigments within liquids has always been a challenge. Natural pigments based on minerals can usually be dispersed with little difficulty, however, because of price synthetic alternatives have been created. These pigment alternatives can be impossible to properly disperse in a liquid medium without the addition of an agent, typically a surfactant, to facilitate the wetting and dispersing of the pigment. Likewise, a wetting or dispersing agent can be added when using natural pigments to maintain low viscosity of the blend. This allows the manufacturer to create more highly concentrated pigment dispersions.

[0003] Historically, many types of dispersing agents have been used to accomplish this task. Examples include carboxylic acids, phosphate esters, phosphate salts such as TKPP, and more recently polymeric surfactants based on acrylic or methacrylic acid; with the latter being the most common.

[0004] It is herein proposed that a new class of natural surfactants derived from alkylpoly glucosides can be used for the dispersion of pigments within a liquid medium to form dispersions of low viscosity and high concentrations. Summary of Various Embodiments of the Invention

[0005] The present invention provides a method for preparing a pigment dispersion according to any one of claims 1 to 16. Brief Description of the Figures

[0032] Figure 1 is a graph that shows dispersant demand viscosity curves for yellow iron oxide in various derivatized alkyl polyglucosides and APG crosspolymers of the present invention.

[0033] Figure 2 is a graph that shows dispersant demand viscosity curves for phthalo blue in various APG crosspolymers of the present invention.

[0034] Figure 3 is a graph that shows dispersant demand viscosity curves for titanium dioxide in various APG crosspolymers of the present invention.

[0035] When described herein, Poly Suga®Mulse D6 and Poly Suga® Mulse D9 refer to a sorbitan oleate decylglucoside crosspolymer; Suga®Nate 160NC is a sodium laurylglucosides hydroxypropylsulfonate; PolySuga®Nate 160P is a sodium hydroxypropyl sulfonate laurylglucoside crosspolymer; and , PolySuga® Phos 8600P is a sodium hydroxypropyl phosphate cocoglucoside crosspolymer. All are manufactured and sold by Colonial Chemical, Inc., South Pittsburg, TN. Detailed Description of the Invention

[0036] The details of one or more embodiments of the presently disclosed subject matter are set forth in this document. Modifications to embodiments described in this document, and other embodiments, will be evident to those of ordinary skill in the art after a study of the information provided in this document. The information provided in this document, and particularly the specific details of the described exemplary embodiments, is provided primarily for clearness of understanding and no unnecessary limitations are to be understood therefrom. In case of conflict, the specification of this document, including definitions, will control.

[0037] While the terms used herein are believed to be well understood by those of ordinary skill in the art, certain definitions are set forth to facilitate explanation of the presently disclosed subject matter.

[0038] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which the invention(s) belong.

[0039] Before the present compounds, compositions, articles, systems, devices, and / or methods are disclosed and described, it is to be understood that they are not limited to specific synthetic methods unless otherwise specified, or to particular reagents unless otherwise specified, as such may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, example methods and materials are now described.

[0040] All publications mentioned herein are incorporated herein by reference to disclose and describe the methods and / or materials in connection with which the publications are cited. The publications discussed herein are provided solely for their disclosure prior to the filing date of the present application. Nothing herein is to be construed as an admission that the present invention is not entitled to antedate such publication by virtue of prior invention. Further, the dates of publication provided herein can be different from the actual publication dates, which need to be independently confirmed.

[0041] The dispersions prepared by the method of the present invention are many times mixtures of alkyl polyglucosides, and optionally a linker arm, and optionally a functionalizing agent, and optionally a crosslinking agent, which are often characterized as constitutional isomers. Constitutional isomers are compounds that have the same general empirical formula but differ in their constitution, i.e. in their structure, such that they can have a different sequence of the atoms and / or different bonds. Constitutional isomers are therefore fundamentally different from stereoisomers, which include both enantiomers and diastereomers.

[0042] Constitutional isomers are in many cases grouped into functional isomers, skeletal isomers, positional isomers and bonding isomers. In the case of functional isomers and bonding isomers, the compounds can have different reactivity; for example, ethanol comprises a hydroxyl group, whereas the constitutionally isomeric dimethyl ether has an ether group. Skeletal isomers and positional isomers differ in the branching and / or the position of functional groups, such that these constitutional isomers can have essentially the same functionality. The expression “essentially the same functionality” accordingly means that the underlying functional group, i.e., for example, a hydroxyl group, a phenyl ring or an ester group, is present in all constitutional isomers, but does not take account of altered reactivity of these groups as a result of different substitution. For example, there is a measurable difference in the reactivity of 1-n-butanol and tert-butanol owing to the stereochemistry, but the functionality as such is identical. In this connection, however, these measurable differences that are covered by the term “essentially the same functionality” are to be neglected, since both compounds in the present case have a hydroxyl functionality. On the other hand, propyne has one alkyne functionality and propadiene has two alkene functionalities. Alkenes, by comparison with alkynes, have a different functionality in the context of this invention, since they exhibit different acidity, for example. Therefore, propyne, by comparison with propadiene, does not have “essentially the same functionality”.

[0043] The mixtures of the present derivatized alkyl polyglucosides have essentially the same functionality. Accordingly, components of the mixture, while constitutional isomers, are not functional isomers, and instead are skeletal isomers and / or positional isomers. That is, the functional group may be in a different position on the same carbon chain or on the same sugar molecule and have essentially the same functionality.

[0044] The term “alkyl” refers to a straight or branched chain monovalent hydrocarbon radical having a specified number of carbon atoms. Alkyl groups may be unsubstituted or substituted with substituents that do not interfere with the specified function of the composition and may be substituted once or twice with the same or different group. Substituents may include alkyl, aryl, alkoxy, hydroxy, mercapto, amino, alkyl substituted amino, nitro, carboxy, carbanyl, carbanyloxy, cyano, methylsulfonylamino, or halogen, for example. Examples of “alkyl” include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, 3-methylpentyl, and the like.

[0045] The term “surfactant”, “surface active agent”, “dispersant”, or “dispersing agent” refers to an organic chemical that when added to a liquid changes the properties of that liquid at a surface. In this instance they modify the wetting properties of pigments, and / or minerals as well as influences the pigment particles interaction with other particles, influencing their aggregation and stability in a liquid carrier.

[0046] Embodiments of the dispersion prepared by the method of the present invention are ethylene oxide and 1,4-di oxane free.

[0047] Alkyl polyglucosides are complex products made by the reaction of glucose and fatty alcohol. In dealing with the chemistry one talks about degree of polymerization (the so called “d.p.”). In the case of traditional alkyl poluglycosides the d.p. is around 1.4. This means that on average the is 1.4 units of glucose for each alkyl group. The fact of the matter is that the resulting material is a mixture having an average of 1.4.

[0048] The specific structure of the product is hard to ascertain completely since many positional isomers are possible, but two examples of structures are as follows: OH (alkyl poly glycosides (d.p. 1))

[0049] It should be clear that if there is a 50 / 50 mixture of the d.p. 1 and d.p. 2 product, the resulting analytical data will show that on average there is a d.p. of 1.5. Saying that a molecule has a d.p. of 1.5 does not mean that each molecule has 1.5 glucose units on it.

[0050] In one embodiment, the dispersant provided in the method of the invention is one that is disclosed in US Patent No. 6,627,612, incorporated herein by reference; and / or dispersants sold by Colonial Chemical, Inc. under the brand names Suga®Nate and Suga®Fax.

[0051] In another embodiment the dispersant provided in the method of the invention is disclosed in US Patent No. 6,958,315, incorporated herein by reference; and / or dispersants sold by Colonial Chemical, Inc. under the brand name Suga®Glycinate.

[0052] In another embodiment the dispersant provided in the method of the invention is disclosed in US Patent No. 8,268,766, incorporated herein by reference; and / or dispersants sold by Colonial Chemical, Inc. under the brand name Poly Suga®Mulse.

[0053] In another embodiment the dispersant provided in the method of the invention is disclosed in US Patent No. 7,507,399, incorporated herein by reference; and / or dispersants sold by Colonial Chemical, Inc. under the brand names Poly Suga®Quats, PolySuga®Nates, PolySuga®Phos.

[0054] In another embodiment the dispersant provided in the method of the invention is disclosed in US Patent No. 7,087,571; and / or dispersants sold by Colonial Chemical, Inc. under the brand name Suga®Mates.

[0055] In another embodiment the dispersant provided in the method of the invention is disclosed in US Patent No. 7,335,627, incorporated herein by reference; and / or dispersants sold by Colonial Chemical, Inc. under the brand name Poly Suga®Carb.

[0056] In another embodiment the dispersants provided in the method of the invention are sugar-based sulfonate-, phosphate-, glycinate-, sulfosuccinate-, and carboxylate-containing dispersants derived from alkyl polyglucosides, including those disclosed in US Patent Nos. 6,627,612; 6,958,315; 7,087,571; 7,507,399 and 7,335,627.

[0057] As stated above, the dispersants provided in the method of the invention are particularly effective dispersants for the dispersion, wetting, and stability of pigments and / or minerals in a liquid carrier. These embodiments are also particularly effective dispersants for the addition of pigments as a liquid slurry to products made with latex such as paints, or other coatings. They are also effective dispersants to be used in personal care, or cosmetics formulations. They also work alone or in combination with nonionic, alkyl polyglucoside-based sorbitan-ester crosspolymers (including those disclosed in US Patent No. 8,268,766). The latter crosspolymers of sorbitan esters and APG’s are also very effective dispersants, wetting and stability of pigments and / or minerals in a liquid carrier.

[0058] The dispersions prepared by the method of the present invention include a single embodiment, or mixture, used alone or in combination with an additional embodiment. The additional embodiment can be in the role of a co-dispersant

[0059] Other co-dispersants can be included in the mixtures of the present invention. Examples of the co-dispersants include ionic and nonionic dispersants.

[0060] These derivatized alkyl polyglucosides are naturally derived, do not possess polyoxyethylene groups (or contain residual ethylene oxide monomer or 1,4-dioxane), are biodegradable and in many cases have been found to have very low skin and eye irritation.

[0062] According to the present invention, the derivatized alkyl polyglucoside is chosen from a polysulfonate derivatized alkyl polyglucoside, polyphosphate derivatized alkyl polyglucoside, polyquaternary derivatized alkyl polyglucoside, polycarboxylated derivatized alkyl polyglucoside, and a polycitrate derivatized alkyl polyglucoside.

[0063] In another embodiment of the present invention, the dispersant is a sorbitan ester alkylglucoside crosspolymer, more specifically a sorbitan ester oleate decylglucoside crosspolymer.

[0064] In another embodiment of the present invention, the dispersant is an alkoxylated alkyl polyglucoside as described in US patent 6,800,741, incorporated herein by reference.

[0065] In one embodiment of the present invention, the derivatized polyglucoside dispersant provided in the method of the present invention comprises a monosaccharide unit, a disaccharide unit, a linker, and a functionalizing agent.

[0066] In this regard, a derivatized alkyl polyglucoside composition of the present invention includes the following, as a mixture: R9 (b) wherein: R is an alkyl chain having 8 to 22 carbon atoms R1, R2, R3, R4 R5, R6, R7, R8, R9, R10, and R11 are independently selected from the group consisting of: -CH2-C(O)-O M+, or -C(O)CH2-C(O)-O M+ OH and H, with the proviso that R'-R11 are not all H; R12 is selected from the group consisting of: -OH, -SO3M+, and - SO4'2M+, -O-P(O)-(OM)2, -N(CH3)2-R1A, -O-C(O)-CH2-OH(SO3 M+)-C(O)-O M+, R1A is CH3-(CH2)n-; M is a charge balancing group selected from H, Na, K, or NH4+; and n is an integer from 0-36; and positional isomers thereof.

[0067] In one embodiment of the present invention, the derivatized polyglucoside dispersant provided in the method of the present invention comprises a monosaccharide unit, a disaccharide unit, a crosslinking agent, and a functionalizing agent.

[0068] In this regard, a derivatized alkyl polyglucoside composition of the present invention includes the following, as a mixture: wherein: R is an alkyl chain having 8 to 22 carbon atoms; a crosslinking agent; and a functionalizing agent selected from: ci- Cl N^—R1 A (i) OH , C1-CH2-CH(OH)-SO3M, C1-CH2-CH(OH)-SO4M, C1-CH2-CH(OH)-CH2-OP(O)-(OM)2, and combinations thereof, wherein R1A is CH3(CH2)n-; (ii) -Cl-CH2-C(O)Na+, 2-halocarboxylic acid, a, P-unsaturated carboxylic acid, cyclic carboxylic acid anhydride, and combinations thereof; M is a charge balancing group selected from H, Na, K, or NtLT; and n is an integer from 0-36; and positional isomers thereof.

[0069] Crosslinking agents for the polyfunctionalized alkyl polyglucosides include those described immediately above include, but are not limited to, l,3-dichloro-2-propanol and epichlorohydrin.

[0070] Thus, in one embodiment of the present invention the dispersant provided in the method of the present invention is a phosphate and / or sulfonate functionalized alkyl polyglucoside of the following compounds, as a mixture, are useful as pigments dispersants, wetting agents, and stabilizers: R----O. .D, . / x. ---R4 R3-------R1 O (a) R2 wherein: R is an alkyl chain having 8 to 22 carbon atoms; R1, R2, R3, and R4 are independently selected from the group consisting of: OH and H, with the proviso that R1, R2, R3, and R4 are not all H; R12 is selected from the group consisting of: -OH -SO3’M+, - SO4'2M+, and -O-P(O)-(OM)2; M is selected from the group consisting of Na, K, NH4; and wherein R5, R6, R7, R8, R9, R10, and R11 are independently selected from the group consisting of: OH and H; and R12 is selected from the group consisting of: -OH, -0-P(0)-(0M)2, -SO3M+ and - SO4-2M, and M is selected from the group consisting of Na, K, NH4; and positional isomers thereof.

[0071] These alkyl polyglucoside dispersants are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380. Two examples of which are sodium laurylglucosides hydroxypropylsulfonate (sold under the brand name Suga®Nate 160NC) and sodium decylglucosides hydroxypropylsulfonate (sold under the brand name Suga®Nate 100NC). The alkylpolyglucoside phosphates of the current invention are manufactured by Colonial Chemical, In., South Pittsburg, TN 37380. An example of which is Sodium Decylglucosides Hydroxypropyl Phosphate, sold under the brand name Suga®Fax D10NC.

[0072] These dispersants are synthesized by the methods outlined in US patent 6,627,612 or their corresponding patents and are generally supplied as clear solutions, 30-50% solids, that are used as pigment or mineral dispersants.,.

[0073] The phosphate functionalized alkyl polyglucoside dispersants of this embodiment are also described in US 8,216,994. Thus, phosphate functionalized alkyl polyglucosides of the present invention include those with the following formula: OH OH

[0074] wherein APG is alkyl polyglucoside; and positional isomers thereof. In some embodiments, the alkyl moiety contains about 12 carbon atoms. An example of a suitable phosphate functionalized alkyl polyglucoside includes, but is not limited to, sodium dilaurylglucoside hydroxypropyl phosphate.

[0075] The sulfonated functionalized alkyl polyglucoside dispersants of this embodiment are also described in US 8,216,988. Thus, sulfonated functionalized alkyl polyglucosides of the present invention include those with the following formula: wherein n is between 1 to about 3, and particularly 1.5; and positional isomers thereof. R is an alkyl chain. Examples of suitable sulfonated functionalized alkyl polyglucosides include sodium laurylglucosides hydroxypropyl sulfonate and sodium declyglucosides hydroxypropyl sulfonate and combinations thereof.

[0076] In an additional embodiment of the present invention glycinate-modified alkylpolyglucoside dispersants are provided represented by compounds of the following formulae, and positional isomers thereof, as a mixture: wherein R is alkyl having 1 to 22 carbon atoms; R1, R2, R3, and R4 are independently selected from and (b) , wherein R is alkyl having 8 to 22 carbon atoms; R5, R6, R7, R8, R9, R10, and R11 are independently selected from and positional isomers thereof.

[0077] The alkylpolyglucoside glycinates of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380, two examples of which are Sodium BisHydroxy ethylglycinate Coco-Glucosides Crosspolymer (sold under the brand name Poly Suga® Glycinate C) and Sodium Bis-Hydroxyethylglycinate Lauryl-Glucosides Crosspolymer (sold under the brand name Poly Suga® Glycinate L).

[0078] These dispersants are synthesized by the methods outlined in US patent 6,958,315 and are generally supplied as clear solutions, 30 - 50 % solids, that are used as pigment or mineral dispersants.

[0079] In an embodiment of the method of the present invention crosspolymers of alkylpolyglucosides and sorbitan esters are provided as sugar-based nonionic dispersants, represented as compounds of the following formulae, and positional isomers thereof, as a mixture: R-0..0^ HO^ (a) OH wherein; R is alkyl having 8 to 22 carbon atoms; and R-------° H 0 ^0^ / -0H ho / X^'^^ (b) OH R is alkyl having 8 to 22 carbon atoms; and (c) a sorbitan ester of the following structure: ^OH ^OH wherein: wherein: R1B is alkyl having 7 to 21 carbons; a crosslinking agent in water; and optionally a functionalizing agent selected from the ct group of: OH , Cl—CH2—CH(OH)—SO3M, Cl—CH- 2—CH(OH)—SO4M, Cl—CH2—CH(OH)CH2—OP(O)—(OM)2, and mixtures thereof; wherein R1A is CH3—(CH2)n—, n is an integer from 0 to 36; M is a charge balancing group selected from H, Na, K, or NH4; and positional isomers thereof.

[0080] Crosslinking agents include those described above herein, and are not limited to, l,3-dichloro-2-propanol and epichlorohydrin.

[0081] The crosspolymers of alkylpolyglucosides and sorbitan esters that are the sugar-based nonionic dispersants of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380, two examples of which are Poly Suga®Mulse D6 and Poly Suga® Mulse D9, both described as sorbitan oleate decylglucoside crosspolymer.

[0082] These dispersants are synthesized by the methods outlined in US patent 8,268,766. The ratio of alkyl polyglucoside monomer to sorbitan ester monomer in the cross polymers can vary from 20:1 to 1:1, respectively, and any range in-between.

[0083] In an embodiment of the method of the present invention sulfonate-modified, phosphate-modified and cationically modified poly-sugar alkyl polyglucoside dispersants are provided, represented by compounds of the following formulae, as a mixture: R--- HO^ (a) OH wherein; R is alkyl having 8 to 22 carbon atoms; and R-0^ / 0^ / -C HO'''’^^'''^ 0 (b) OH R is alkyl having 8 to 22 carbon atoms; a crosslinking agent; and a functionalizing agent selected from: Cl' cr n—r1 OH ^OH ’OH DH --OH H , wherein: Cl—CH2—CH(OH)—so3m, Cl—CH2—CH(OH)—SO4M, Cl—CH2—CH(OH)CH2—OP(O)—(OM)2, and mixtures thereof; wherein R1 is CH3—(CH2)n—; n is an integer from 0 to 36; M is a charge balancing group selected from H, Na, K, or NH4; and positional isomers thereof.

[0084] Crosslinking agents include those described above herein, and are not limited to, l,3-dichloro-2-propanol and epichlorohydrin.

[0085] These alkyl polyglucosides of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380, as shown in US Patent No. 7,507,399. Examples of these alkyl polyglucosides are: sodium hydroxypropyl phosphate decylglucoside crosspolymer (Poly Suga® Phos 1000P), sodium hydroxypropyl phosphate laurylglucoside crosspolymer (PolySuga®Phos 1200P), Sodium hydroxypropyl phosphate cocoglucoside crosspolymer (PolySuga® Phos 8600P), Sodium hydroxypropyl sulfonate butylglucoside crosspolymer (PolySuga®Nate 40P), Sodium hydroxypropyl sulfonate decylglucoside crosspolymer (PolySuga®Nate 100P), Sodium hydroxypropyl sulfonate laurylglucoside crosspolymer (PolySuga®Nate 160P NC), Polyquaternium-78 (Poly Suga®Quat L-1010P), Polyquaternium-80 (Poly Suga®Quat L-1210P) and Polyquatemium-81 (Poly Suga®Quat S-1201P).

[0086] Another description of the dispersants of this embodiment is described in US Patent No. 8,329,633. Thus, poly quaternary functionalized alkyl polyglucosides of the present invention have the following formula: wherein R is an alkyl group having from about 8 to about 22 carbon atoms and n is an integer ranging from 4 to 6; and positional isomers thereof.

[0087] Another description of the dispersants of this embodiment is described in US Patent No. 8,262,805. Thus, poly sulfonate functionalized alkyl polyglucosides of the present invention have the following formula: O'Na+ O'Na+ O'Na+ wherein R is an alkyl group having from about 8 to about 22 carbon atoms and n is an integer ranging from 4 to 6; and positional isomers thereof.

[0088] Another example of the dispersants of this embodiment is described in US Patent No. 8,287,659. That is, polyphosphate functionalized alkyl polyglucosides of the following formula: wherein R is an alkyl group having from about 8 to about 22 carbon atoms; and positional isomers thereof.

[0089] Another dispersant provided in the method of the present invention is also described in US Patent Nos. 8,557,760 and 8,389,457. Quaternary functionalized alkyl polyglucosides of the present invention may have the following representative formula: wherein R1 is an alkyl group having from about 8 to about 22 carbon atoms, and R2 is CH3(CH2)n, and n is independently an integer from 0-21; and positional isomers thereof. Examples of suitable quaternary functionalized alkyl polyglucosides dispersants include those in the R1 alkyl moiety contains primarily about 12 carbons, the R2 group is CH3.

[0090] In other embodiments of the method of the present invention sulfosuccinate-modified, alkylpolyglucoside dispersants are provided, represented by compounds of the following formulae, as a mixture: R--°\ \q--R4 R3—--R1 O (a) R2 wherein R is alkyl having 8 to 22 carbon atoms; R1, R2, R3, and R4 are independently selected from -CH2-CH(OH)-CH2-R12, and H, with the proviso that R1, R2, R3, and R4 are not all H; R12 is -O-C(O)-CH2-CH(SO3 M+)-C(0)-0' M+ M is a charge balancing group selected from H, Na, K, or NH4; and (b) R10 , wherein R is alkyl having 8 to 22 carbon atoms; R5, R6, R7, R8, R9, R10, and R11 are independently selected from -CH2-CH(OH)-CH2-R12, and H, with the proviso that R5, R6, R7, R8, R9, R10, and R11 are not all H; R12 is -O-C(O)-CH2-CH(SO3 M+)-C(O)-O- M+ M is a charge balancing group selected from H, Na, K, or NH4; and positional isomers thereof.

[0091] The sulfosuccinate-modified PolySuga® alkylpolyglucosides of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380. These dispersants are synthesized by the methods outlined in US patent 7,087,571 and are generally supplied as clear solutions, 30 - 50 % solids, that are used as pigment or mineral dispersants.

[0092] In another embodiment of the method of the present invention carboxymethyl- modified, Poly Suga®-alkylpolyglucoside dispersants are provided, represented by the following components, as a mixture: (a) OR4 wherein one of R3, R4, R5, and R6 is -CH2-C(O)-O’ M+ or -C(O)-CH2-C(O)-O' M+, with the remaining R groups being H; R is alkyl having 6 to 30 carbon atoms; M is H, Na, or K; and (b) a 1,3 dicloloro-2-propanol crosslinker; and positional isomers thereof.

[0093] The carboxymethyl-modified Poly Suga® alkyl polyglucosides of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380, examples of which are Sodium Maleate Decylglucoside Crosspolymer (Poly Suga®Carb DM), Sodium Maleate Laurylglucoside Crosspolymer (Poly Suga®Carb LM) and Sodium Succinate Laurylglucoside Crosspolymer (Poly Suga®Carb LS).

[0094] These dispersants are synthesized by the methods outlined in US patent 7,335,627 and are generally supplied as clear solutions, 40 - 60 % solids, that are used as pigment dispersants.

[0095] In another embodiment of the present invention a citrate-functionalized polymeric alkylglucoside dispersant is provided, represented by the following components, as a mixture: and positional isomers thereof. The citrate-modified alkyl polyglucosides of the current invention are manufactured by Colonial Chemical, Inc., South Pittsburg, TN 37380, an example of which is Disodium Laurylglucosides Hydroxypropyl Citrate (Suga®Citrate LI C)

[0096] The functionalized alkylpolyglucosides of the present invention have found wide application mostly in the personal care market in various cleansing products such as shampoos, body washes and facial washes. Additionally, their use in household, industrial and institutional cleaning has been the subject of a number of patents. The Suga®Quats and Poly Suga®Quats dispersants mentioned above have been patented for use in various hard-surface cleaning applications (outlined in US patents 8,557,760; 8,389,457; 8,329,633; 8,877,703; 10,035,975; and 9,474,703 issued to Ecolab USA Inc.). The Suga®Nate and Poly Suga®Nate dispersants mentioned above have also been patented for use in various hard-surface cleaning applications (8,071,520; 8,216,988; and 8,262,805 issued to Ecolab USA Inc.). The Poly Suga®Glycinates mentioned above have also been patented for use in various hard-surface cleaning applications (US patent 8,299,099 issued to Ecolab USA Inc.). The Suga®Fax and Poly Suga®Fax dispersants mentioned above have also been patented for use in various hard-surface cleaning applications (8,216,994; 8,287,659; and 8,969,285 issued to Ecolab USA Inc.). The Poly Suga®Mates dispersants mentioned above have been patented for use in various hard-surface cleaning applications of (8,658,584 issued to Ecolab USA Inc.).

[0097] As stated above, the present inventors have found the dispersants provided in the method of the present invention, and combinations thereof, to be useful and beneficial in a pigment or mineral dispersant process. In the present invention, the dispersant is used to facilitate the wetting, dispersion, and stabilization of a pigment, and optionally a mineral in a liquid carrier. This generally results in a concentrated pigment slurry or paste.

[0098] The pigments suitable for this process are understood to one of ordinary skill in the art. As stated above, examples of pigments or minerals include, but are not limited to, phthalocyanine pigments, calcium carbonate, titanium dioxide, inorganic clays, iron oxides, ultramarine pigments, han purple, cobalt violet, manganese violet, Persian blue, cobalt blue, cerulean blue, Egyptian blue, manganese blue, azurite, copper carbonate, chrome green, terra verte, primrose yellow, crocoite, aurelian, yellow ochre, zinc chromate, raw umber, raw sienna, carbon black, zinc oxide, alizarin, arylide yellow, azo pigments, diarylide yellow, naphthol red, Indian yellow, indigo dye, orange 15, violet 23, yellow 10, yellow 12, yellow 13, yellow 16, yellow 81, yellow 83, yellow 139, yellow 185, quinacridone, tyrian purple, paris green, or other organic or inorganic pigments.

[0099] Also described herein is a method of pigmenting latex or solution-based paints, comprising the dispersants of the present invention. The paints presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a paint formulation comprises, in part, the dispersants of the present invention to disperse the pigments and / or filler minerals within the paint composition. In this embodiment the dispersant can be added neat to the paint formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00100] Also described herein is a method of pigmenting latex or solution-based adhesives, comprising the dispersants of the present invention. The adhesives presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, an adhesive formulation comprises, in part, the dispersants of the present invention to disperse the pigments and / or filler minerals within the paint composition. In this embodiment the dispersant can be added neat to the adhesive formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00101] Also described herein is a method of pigmenting latex or solution-based primers, comprising the dispersants of the present invention. The primers presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a primer formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the primer composition. In this embodiment the dispersant can be added neat to the primer formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00102] Also described herein is a method of pigmenting latex or solution-based textile compounds, comprising the dispersants of the present invention. The textile compounds presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a textile compound formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the textile compound composition. In this embodiment the dispersant can be added neat to the textile compound formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00103] Also described herein is a method of pigmenting latex or solution-based clear coat compositions, comprising the dispersants of the present invention. The clear coat compositions presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a clear coat formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the clear coat composition. In this embodiment the dispersant can be added neat to the clear coat formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00104] Also described herein is a method of pigmenting latex or solution-based water-resistant sealers, comprising the dispersants of the present invention. The sealers presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a sealer formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the sealer composition. In this embodiment the dispersant can be added neat to the sealer formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00105] Also described herein is a method of pigmenting cementitious products, comprising the dispersants of the present invention. These products may include, but are not limited to, concrete, grouts, or mortars. The cementitious products presented in this embodiment may use water, or any other liquid as a carrier, such as a latex. In this embodiment, a cement formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the cement composition. In this embodiment the dispersant can be added neat to the cement formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00106] Also described herein is a method of pigmenting paper products, comprising the dispersants of the present invention. The paper products presented in this embodiment may use water, or any other organic liquid during the process before curing or drying into finished products. In this embodiment, a paper formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the paper composition. In this embodiment the dispersant can be added neat to the paper formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00107] Also described herein is a method of pigmenting or adding filler minerals to solid polymer products, comprising the dispersants of the present invention. The products presented in this embodiment may use water, any other organic liquid as a carrier, or no carrier before curing, drying, or molding to a final product. In this embodiment, a polymer formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals within the polymer composition. In this embodiment the dispersant can be added neat to the polymer formulation, added to the formulation as part of a pigment / mineral slurry, or added using any other method known to those skilled in the arts.

[00108] Also described herein is a method of pigmenting or adding filler minerals, or functional minerals to personal care products, comprising the dispersants of the present invention. The personal care formulations presented in this embodiment may use water, or any other organic liquid as a carrier. In this embodiment, a personal care formulation comprises the dispersants of the present invention to disperse the pigments and / or filler minerals and / or functional minerals within the cosmetic composition. In this embodiment the dispersant can be added neat to the personal care formulation or may be added to the formulation as part of a pigment / mineral slurry.

[00109] Also described herein is a coating composition that comprises (i) at least one derivatized alkyl polyglucoside dispersant and / or alkyl polyglucoside sorbitan ester crosspolymer; (ii) water and / or an organic solvent; a polymer and / or an alkyd; a filler and / or a functional mineral; and at least one colorant or pigment.

[00110] In the embodiment, the pigment, filler mineral or functional mineral may be chosen from the following, including, but not limited to, phthalocyanine pigments, calcium carbonate, titanium dioxide, barium sulfate, nepheline syenite, inorganic clays, iron oxides, ultramarine pigments, han purple, cobalt violet, manganese violet, Persian blue, cobalt blue, cerulean blue, Egyptian blue, manganese blue, azurite, copper carbonate, chrome green, terra verte, primrose yellow, crocoite, aurelian, yellow ochre, zinc chromate, raw umber, raw sienna, carbon black, zinc oxide, alizarin, arylide yellow, azo pigments, diarylide yellow, naphthol red, Indian yellow, indigo dye, orange 15, violet 23, yellow 10, yellow 12, yellow 13, yellow 16, yellow 81, yellow 83, yellow 139, yellow 185, quinacridone, tyrian purple, paris green, or other organic or inorganic pigments / filler minerals.

[00111] The polymer may be an acrylic polymer, styrene acrylic polymer, vinyl acetate / acrylic polymer, styrene-butadiene polymer, polyisoprene polymer, neoprene polymer, natural rubber polymer, ethylene-vinyl acetate polymer, polyolefin where the individual monomers consist of alpha olefins with carbon chain lengths between 2 and 22, maleic acidacrylic polymers, maleic acid-styrene polymers, epoxy polymers, polyamides, polyurethanes, polyesters, polyethers, or other polymers suitable for a coating composition.

[00112] In other aspects, the polymer is 100% actives. Also, the polymer may be hydrophobic and emulsified in water. In other aspects, the polymer is water soluble and is in an aqueous solution. In other aspects, the polymer is soluble in an organic solvent and is in a solution of said solvent.

[00113] The organic solvent may include, but is not limited to, an alcohol, a ketone, an aldehyde, a hydrocarbon, an aromatic hydrocarbon, a halogenated hydrocarbon, a halogenated aromatic hydrocarbon, an acetate, an organic carbonate, dimethyl sulfoxide, an ether, a carboxylic acid, an ester, an amine, or other organic solvent.

[00114] The coating may be a multi part system containing monomers that react together once combined, usually, during application.

[00115] In embodiments, the monomers may be chosen from glycidyl ethers and amines that react to form polyamines. Also, the monomers may be chosen from glycidyl ethers and alcohols that react to form poly ethers. Also, the monomers may be chosen from an amine and an isocyanate and a polyol that react to form polyamides.

[00116] The alkyd is the reaction product of a polyol with any or all of the following: (i) one or more organic molecules containing multiple carboxylic acid groups; (ii) one or more anhydride; and / or (iii) one or more fatty acid. Also, the alkyd may be dispersed or emulsified in water. Also, the alkyd may be dissolved in an organic solvent. Examples

[00117] The following examples are put forth to provide those of ordinary skill in the art with a complete disclosure and description of how the compounds, compositions, articles, devices and / or methods claimed herein are made and evaluated and are intended to be purely exemplary of the invention and are not intended to limit the scope of what the inventors regard as their invention. Efforts have been made to ensure accuracy with respect to numbers (e.g., amounts, temperature, etc.), but some errors and deviations should be accounted for. EXAMPLE 1: Phthalo Blue

[00118] Aqueous pigment dispersions were prepared using phthalo blue as pigment. Several functionalized alkyl polyglucosides or alkyl polyglucoside sorbitan ester crosspolymers were tested in their efficacy as pigment dispersants using the following formula. RAW MATERIAL MASS PERCENT Water 89.4 41.87 Phthalo Blue 91 42.62 Dispersant 29.85 13.98 Bentonite 1.25 0.59 Defoamer 2 0.94

[00119] In this preparation water, dispersant, and defoamer were first added to a 100mL paint can and stirred under light agitation until uniform. Once uniform, Phthalo Blue was added slowly under high agitation. Once pigment was all added, the mixture was kept under high agitation to reduce particle size. It is to be noted that deviations from this formula in respect to actual amount of dispersant were made to create a flowable product. Actual percentages and physical property data are detailed in the following table. DISPERSANT TSC % DISPERSANT VISCOSITY HEGMAN (pm) STATUS Poly Suga®Mulse D9 52.15 9.78 165 0 PASS* Suga®Fax D10 48.56 17.36 165 <5 PASS Suga®Nate 160 NC 48.73 15.03 185 <3 PASS* Poly Suga®Nate 100P 48.82 13.98 200 <8 PASS* *In all cases the phthalo blue pigment was successfully dispersed. In the experiments marked with (*) the dispersions did settle within a 14-day window. Those skilled in the art realize that adjusting other formulation parameters can result in stable dispersions. All other dispersions were stable without further adjustment. [Poly Suga®Mulse D9 (Sorbitan Oleate Decylglucoside Crosspolymer), Suga®Fax D10NC (Sodium Decylglucosides Hydroxypropyl Phosphate), Suga®Nate 160NC (Sodium Laurylglucosides Hydroxypropylsulfonate, and PolySuga®Nate 100P (Sodium Hydroxypropyl Sulfonate Decylglucoside Crosspolymer) are manufactured and sold by Colonial Chemical, Inc. located in South Pittsburg, TN], EXAMPLE 2: Toluidine Red

[00120] Aqueous pigment dispersions were prepared using toluidine red as pigment. Several functionalized alkyl polyglucosides or alkyl polyglucoside sorbitan ester crosspolymers were tested in their efficacy as pigment dispersants using the following formula. RAW MATERIAL MASS PERCENT Water 89.4 41.87 Toluidine Red 91 42.62 Dispersant 29.85 13.98 Bentonite 1.25 0.59 Defoamer 2 0.94

[00121] In this preparation water, dispersant, and defoamer were first added to a 100mL paint can and stirred under light agitation until uniform. Once uniform, Toluidine Red was added slowly under high agitation. Once pigment was all added, the mixture was kept at under high agitation until particle size was reduced to less than 10 micrometers. It is to be noted that deviations from this formula in respect to actual amount of dispersant were made to create a flowable product. Actual percentages and physical property data are detailed in the following table. DISPERSANT TSC % DISPERSANT VISCOSITY HEGMAN (pm) STATUS Poly Suga®Mulse D9 49.72 19.45 270 0 PASS Suga®Fax D10 45.69 22.7 245 0 PASS Suga®Nate 160 NC 45.46 22.63 310 0 PASS Poly Suga®Nate 100P 45.72 18.92 255 0 PASS* *In all cases the toluidine red pigment was successfully dispersed. In the experiment marked with (*) the dispersion did settle within a 14-day window. Those skilled in the art realize that adjusting other formulation parameters can result in stable dispersions. All other dispersions were stable without further adjustment. EXAMPLE 3: Yellow 170

[00122] Aqueous pigment dispersions were prepared using Yellow 170 as pigment. several functionalized alkyl polyglucosides or alkyl polyglucoside sorbitan ester crosspolymers were tested in their efficacy as pigment dispersants using the following formula. RAW MATERIAL MASS PERCENT Water 89.4 41.87 Yellow 170 91 42.62 Dispersant 29.85 13.98 Bentonite 1.25 0.59 Defoamer 2 0.94

[00123] In this preparation water, dispersant, and defoamer were first added to a 100mL paint can and stirred under light agitation until uniform. Once uniform, Yellow 170 was added slowly under high agitation. Once pigment was all added, the mixture was kept at under high agitation until particle size was reduced to less than 10 micrometers. It is to be noted that deviations from this formula in respect to actual amount of dispersant were made to create a flowable product. Actual percentages and physical property data are detailed in the following table. DISPERSANT TSC % DISPERSANT VISCOSITY HEGMAN (pm) STATUS Poly Suga®Mulse D9 50.91 18.98 165 0 PASS Suga®Fax D10 44.36 15.25 165 0 PASS* Suga®Nate 160 NC 46.54 14.65 185 0 PASS Poly Suga®Nate 100P 46.41 14.65 200 0 PASS *In all cases the Yellow 170 pigment was successfully dispersed. In the experiment marked with (*) the dispersions did settle within a 14-day window. Those skilled in the art realize that adjusting other formulation parameters can result in stable dispersions. All other dispersions were stable without further adjustment. EXAMPLE 4: Titanium Dioxide

[00124] Aqueous pigment dispersions were prepared using titanium dioxide as pigment, several functionalized alkyl polyglucosides or alkyl polyglucoside sorbitan ester crosspolymers were tested in their efficacy as pigment dispersants using the following formula. RAW MATERIAL MASS PERCENT Water 89.1 35.31 Titanium Dioxide 150 59.44 Dispersant 10 3.96 Bentonite 1.25 0.50 Defoamer 2 0.79

[00125] In this preparation water, dispersant, and defoamer were first added to a 100mL paint can and stirred under light agitation until uniform. Once uniform, Titanium Dioxide was added slowly under high agitation. Once pigment was all added, the mixture was kept at under high agitation until particle size was reduced to less than 10 micrometers. It is to be noted that deviations from this formula in respect to actual amount of dispersant were made to create a flowable product. Actual percentages and physical property data are detailed in the following table. DISPERSANT TSC % DISPERSANT VISCOSITY HEGMAN (pm) STATUS Poly Suga®Phos 1000P 59.37 2.05 495 <5 PASS Suga®Nate 160 NC 61.82 1.92 195 <5 PASS Poly Suga®Nate 160P 65.81 1.93 575 <5 PASS Polyacrylic Acid Control 62.07 7.71 265 <5 FAIL* *In all cases the Titanium Dioxide was successfully dispersed. In the control experiment marked with (*) the dispersion did settle within a 14-day window. All other dispersions were stable without further adjustment. Poly Suga®Phos 1000P (Sodium Hydroxypropylphosphate Decylglucoside Crosspolymer) and PolySuga®Nate 160P (Sodium Hydroxypropyl Sulfonate Laurylglucoside Crosspolymer) are manufactured and sold by Colonial Chemical, Inc., South Pittsburg, TN. EXAMPLE 5: Yellow Iron Oxide

[00126] Aqueous pigment dispersions were prepared using Yellow Iron Oxide as pigment, several functionalized alkyl polyglucosides or alkyl polyglucoside sorbitan ester crosspolymers were tested in their efficacy as pigment dispersants using the following formula. RAW MATERIAL MASS PERCENT Water 89.1 35.31 Yellow Iron Oxide 150 59.44 Dispersant 10 3.96 Bentonite 1.25 0.50 Defoamer 2 0.79

[00127] In this preparation water, dispersant, and defoamer were first added to a 100mL paint can and stirred under light agitation until uniform. Once uniform, Yellow Iron Oxide was added slowly under high agitation. Once pigment was all added, the mixture was kept at under high agitation until particle size was reduced to less than 10 micrometers. It is to be noted that deviations from this formula in respect to actual amount of dispersant were made to create a flowable product. Actual percentages and physical property data are detailed in the following table. DISPERSANT TSC % DISPERSANT VISCOSITY HEGMAN (pm) STATUS Poly Suga®Phos 1000P 54.05 4.3 150 <5 PASS Suga®Nate 160 NC 53.89 4.3 135 <5 PASS Poly Suga®Nate 160P 54.12 4.3 142 <5 PASS Polyacrylic Acid Control 54.58 4.3 175 <5 FAIL* *In all cases the Yellow Iron Oxide was successfully dispersed. In the control experiment marked with (*) the dispersion did settle within a 14-day window. All other dispersions were stable without further adjustment. EXAMPLE 6: Dispersant Demand Viscosity Curves

[00128] Dispersant demand viscosity curves were created to find the optimum usage levels of several dispersants outlined within this patent. In this preparation water, dispersant, and defoamer were first added to a 1000mL beaker and stirred under light agitation until uniform. Once uniform, pigment was added slowly under high agitation using a rotor stator mixer, Ross Model HSM-100LSI-I Laboratory High Shear Mixer. Once pigment was all added, the mixture was kept at under high agitation until particle size was reduced to less than 10 micrometers. Three different pigments were chosen for this study to evaluate the efficacy of the dispersants over a broad spectrum of pigment chemistries: yellow iron oxide, phthalo blue and titanium dioxide. The viscosity curves for these three pigments in various derivatized alkyl polyglucosides and alkyl polyglucosides (APG) crosspolymers are shown in Figures 1 through 3 below. The data for those curves in listed in Tables 1 through 3. Table 1. Dispersant Demand Viscosity Curve data for Yellow Iron Oxide in various derivatized alkyl polyglucosides and APG crosspolymers PERCENT DISPERSANT Poly Suga® Mulse D6 Poly Suga® Mulse D9 Suga® Nate 160NC Poly Suga® Nate160P Poly Suga® Phos 8600P 1 - - 1000000+ - - 2 1000000+ 1000000+ 1000000+ 1000000+ 1000000+ 3 300000 255000 1000000+ - - 4 160 40000 3750 27500 1000000+ 4.5 - - 1580 4100 - 5 280 3000 585 - 375000 5.5 - - 340 820 57000 6 240 1050 290 605 2950 6.5 - - 270 580 - 7 - 6600 280 275 1740 8 - - 290 516 1000 10 530 - 435 - 660 11 - - - 500 - 13 - - - 615 950 15 1370 - - - 1100 Table 2. Dispersant Demand Viscosity Curve data for Phthalo Blue in Alkyl Poly Glucoside crosspolymers PERCENT DISPERSANT Poly Suga® Mulse D6 Poly Suga® Mulse D9 2.5 762000 1000000+ 5 729000 1000000+ 6 330000 89000 7.5 325 1000 10 45 1035 15 700 1700 17.5 2200 - Table 3. Dispersant Demand Viscosity Curve data for Titanium Dioxide in Alkyl Poly Glucoside crosspolymers PERCENT DISPERSANT Poly Suga® Mulse D6 Poly Suga® Mulse D9 1 1000000+ 1000000+ 2 1000000+ - 3 330000 600 4 250 375 5 350 520 6 810 535 7 1370 - 10 2700 560 15 1100 EXAMPLE 7: Stability Studies

[00129] The following is exemplary of how stability studies were conducted on the pigment / mineral dispersions in the various surfactants of this invention. In general, it was found the derivatized alkylpolyglucoside improved stability against settling and sedimentation of pigment dispersion. EXAMPLE 8: Stability of Napthol Red AS dispersions

[00130] Several dispersions of Napthol Red AS were prepared using the percentages in Table 4 in order to test their long-term stability. In these preparation water, dispersant, and defoamer were first added to a 1000mL beaker and stirred under light agitation until uniform. Once uniform, pigment was added slowly under high agitation. Once pigment was all added, the mixture was kept at under high agitation using a rotor stator mixer until particle size was reduced to less than 10 micrometers. Each sample was tested for settling after 30 days of storage at room temp and at 50 °C. Table 4. Stability of Napthol Red AS Sample ID Water Defoamer Poly Suga®Mulse D6 Poly Suga®Mulse D9 Napthol Red AS Viscosity 30 Stability RT 30 Day Stability 50°C Sample 1 52.7 1.4 8 0 37.9 185 PASS PASS Sample 2 52.7 1.4 0 8 37.9 210 PASS PASS

[00131] The examples above are exemplary and clearly illustrate the dispersing properties of derivatized alkyl poly glucosides and crosspolymers of alkyl polyglucosides and sorbitan esters for pigments, filler minerals, or functional minerals. It is herein proposed that the class of natural surfactants derived from alkylpoly glucosides can be used for the dispersion of pigments within a liquid medium to form dispersions of low viscosity and high concentrations.

[00132] As used herein, the singular forms “a,” “an” and “the” include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to “a surfactant” includes mixtures of two or more such dispersants.

[00133] Ranges can be expressed herein as from “about” one particular value, and / or to “about” another particular value. When such a range is expressed, a further aspect includes from the one particular value and / or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms a further aspect. It will be further understood that the endpoints of each of the ranges are significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are a number of values disclosed herein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. For example, if the value “10” is disclosed, then “about 10” is also disclosed. It is also understood that each unit between two particular units are also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.

[00134] Unless stated to the contrary, a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible isomer, e.g., each enantiomer and diastereomer, and a mixture of isomers, such as a racemic or scalemic mixture. Compounds described herein can contain one or more asymmetric centers and, thus, potentially give rise to diastereomers and optical isomers. Unless stated to the contrary, the present invention includes all such possible diastereomers as well as their racemic mixtures, their substantially pure resolved enantiomers, all possible geometric isomers, and pharmaceutically acceptable salts thereof. Mixtures of stereoisomers, as well as isolated specific stereoisomers, are also included. During the course of the synthetic procedures used to prepare such compounds, or in using racemization or epimerization procedures known to those skilled in the art, the products of such procedures can be a mixture of stereoisomers. Additionally, unless expressly described as “unsubstituted”, all substituents can be substituted or unsubstituted.

[00135] The invention thus being described, it will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the scope or spirit of the invention. Other aspects of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only.

Claims

1. A method for preparing a pigment dispersion, the method comprising:providing a liquid carrier in a range 20-80% by weight comprising at least one derivatized alkyl polyglucoside, and / or an alkyl polyglucoside sorbitan ester crosspolymer dispersant in a range of 0.01-50%; andadding at least one pigment, and optionally adding at least one filler mineral or functional mineral, the at least one pigment, filler mineral and functional mineral making up 20-80% of the dispersion,wherein the derivatized alkyl polyglucoside is chosen from a polysulfonate derivatized alkyl polyglucoside, polyphosphate derivatized alkyl polyglucoside, polyquaternary derivatized alkyl polyglucoside, polycarboxylated derivatized alkyl polyglucoside, and a polycitrate derivatized alkyl polyglucoside.

2. The method of claim 1, wherein the liquid carrier is water.

3. The method of one of claim 1 or claim 2, wherein the liquid carrier further comprises adefoamer.

4. The method of one of claims 1 to 3, wherein the pigment, filler mineral or functional mineral is chosen from the following, phthalocyanine pigments, calcium carbonate, titanium dioxide, barium sulfate, nepheline syenite, inorganic clays, iron oxides, ultramarine pigments, han purple, cobalt violet, manganese violet, Persian blue, cobalt blue, cerulean blue, Egyptian blue, manganese blue, azurite, copper carbonate, chrome green, terra verte, primrose yellow, crocoite, aurelian, yellow ochre, zinc chromate, raw umber, raw sienna, carbon black, zinc oxide, alizarin, arylide yellow, azo pigments, diarylide yellow, naphthol red, Indian yellow, indigo dye, orange 15, violet 23, yellow 10, yellow 12, yellow 13, yellow 16, yellow 81, yellow 83, yellow 139, yellow 185, quinacridone, tyrian purple, paris green, or other organic or inorganic pigments / filler minerals.

5. The method of one of claims 1 to 4, wherein the alkyl polyglucoside crosspolymer is a sorbitan ester alkylglucoside crosspolymer including sorbitan oleate decylglucoside crosspolymer.

6. The method of one of claims 1 to 5, wherein the dispersion is ethylene oxide and 1,4-dioxane free.

7. The method of one of claims 1 to 6, wherein the derivatized polyglucoside dispersant comprises a monosaccharide unit, a disaccharide unit, a linker, and a functionalizing agent.

8. The method of one of claims 1 to 7, wherein the derivatized polyglucoside dispersant comprises a monosaccharide unit, a disaccharide unit, a crosslinking agent, and a functionalizing agent.

9. The method of one of claims 1 to 8, wherein the derivatized alkyl polyglucoside dispersant is a composition that includes the following, as a mixture:(a) R2 , andwherein:R is an alkyl chain having 8 to 22 carbon atoms;R1, R2, R3, R4 R5, R6, R7, R8, R9, R10, and R11 are independently selected from the group consisting of: -CH2-C(O)-O M+, or -C(O)CH2-C(O)-O M+OH and H, with the proviso that R^R11 are not all H;R12 is selected from the group consisting of:-OH, -SO3M+, and - SO4'2M+, -O-P(O)-(OM)2,-N(CH3)2-R1A, -O-C(O)-CH2-OH(SO3 M+)-C(O)-O M+,R1A is CH3-(CH2)n-;M is a charge balancing group selected from H, Na, K, or NH4+; andn is an integer from 0-36;and positional isomers thereof.

10. The method of one of claims 1 to 8, wherein the derivatized alkyl polyglucoside dispersant is a composition that includes the following, as a mixture:(a) OH , andwherein:R is an alkyl chain having 8 to 22 carbon atoms;a crosslinking agent; anda functionalizing agent selected from:(i) OH , C1-CH2-CH(OH)-SO3M, C1-CH2-CH(OH)-SO4M,C1-CH2-CH(OH)-CH2-OP(O)-(OM)2, and combinations thereof, whereinR1A is CH3(CH2)n-;(ii) -Cl-CH2-C(0)-0-Na+, 2-halocarboxylic acid, a, P-unsaturated carboxylic acid, cyclic carboxylic acid anhydride, and combinations thereof;M is a charge balancing group selected from H, Na, K, or NH4 ; andn is an integer from 0-36; and positional isomers thereof.

11. The method of claim 10, wherein the crosslinking agent is l,3-dichloro-2-propanol or epichlorohydrin.

12. The method of one of claims 1 to 8, wherein the alkyl polyglucoside sorbitan ester crosspolymer dispersant is a composition that includes the following, as a mixture:wherein;R is alkyl having 8 to 22 carbon atoms; andR is alkyl having 8 to 22 carbon atoms; and(c) a sorbitan ester of the following structure:OHOHwherein:R1B is alkyl having 7 to 21 carbons;a crosslinking agent in water; and optionally a functionalizing agent selected from theCl’group of: OH , Cl—CH2—CH(OH)—SO3M, Cl—CH-2—CH(OH)—SO4M, Cl—CH2—CH(OH)CH2—OP(O)—(OM)2, and mixtures thereof;wherein R1A is CH3—(CH2)n—,n is an integer from 0 to 36;M is a charge balancing group selected from H, Na, K, or NH4;and positional isomers thereof.

13. The method of claim 12, wherein the crosslinking agent is l,3-dichloro-2-propanol or epichlorohydrin.

14. The method of one of claims 1 to 13, wherein the liquid carrier further comprises a codispersant.

15. The method of claim 14, wherein the co-dispersant is a derivatized alkyl polyglucoside or alkyl polyglucoside sorbitan ester crosspolymer dispersant that is ethylene oxide and 1,4-dioxane free.

16. The method of claim 14, wherein the co-dispersant is selected from alkyl polyglucosides, alkyl polyglucoside sorbitan ester crosspolymers, fatty alcohol ethoxylates, alkylphenol ethoxylates, phosphate esters of fatty alcohols, phosphate esters of fatty alcohol ethoxylates, phosphate esters of alkylphenol ethoxylates, sulfates of fatty alcohols, sulfates of fatty alcohol ethoxylates, sulfates of alkylphenol ethoxylates, sulfonates of fatty alcohols, sulfonates of fatty alcohol ethoxylates, sulfonates of alkylphenol ethoxylates, ethoxylated terpenes, phosphate esters of ethoxylated terpenes, sulfates of ethoxylated terpenes, sulfonates of ethoxylated terpenes, sulfosuccinates, quaternary amines, betaines, carboxymethylated fatty alcohols, carboxymethylated fatty alcohol ethoxylates, carboxymethylated alkylphenol ethoxylates, polyacrylic acid polymers, polymethacrylic acid polymers, gemini surfactants, or tertiary amine surfactants.

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