US 200901 63449A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0163449 A1 Wempe (43) Pub. Date: Jun. 25, 2009 (54) SULFO-POLYMER POWDER AND (22) Filed: Oct. 31, 2008 SULFO-POLYMER POWDER BLENDS WITH O O CARRIERS AND/OR ADDITIVES Related U.S. Application Data (60) Provisional application No. 61/015,365, filed on Dec. (75) Inventor: Michael Fitzpatrick Wempe, 20, 2007. Kingsport, TN (US) Publication Classification Correspondence Address: (51) Int. Cl. BRETTL NELSON A613/60 (2006.01) EASTMLAN CHEMICAL COMPANY A6II 47/34 (2006.01) 1OO NORTHEASTMAN ROAD (52) U.S. Cl. ...................................... 514/159; 514/772.3 KINGSPORT, TN37660-5075 (US) (57) ABSTRACT (73) Assignee: Eastman Chemical Company, Sulfo-polyester powders and sulfo-polyester blend powders, Kingsport, TN (US) the incorporation of carriers and/or actives, and methods of making the powders as well as dispersions employing these (21) Appl. No.: 12/262,986 powders. AQ38S (Left) and AQ38P (Right) Comparison & & Patent Application Publication Jun. 25, 2009 Sheet 2 of 3 US 2009/O163449 A1 Figure 2 Kojic Acid Hydroquinone Vitamin12 E TPGS-1000 Salicyclic Acid Glycolic Acid Lidocaine CO2H CO2H HO N1N N OH r Patent Application Publication Jun. 25, 2009 Sheet 3 of 3 US 2009/O163449 A1 Figure 3A g 125 v AQ55+ traconazole 100 I AUC 612 it 170 ng himl 75 ; i CMC + traconazole 3 50 v, AUCo24. 115 it 59 ng himl 25 O Figure 3B 250 A AG.55 traConazole 200 AUC-24 1429 it 755 ng himl 32 150 SSO XSS 100 O Ces5 50 US 2009/01 63449 A1 Jun. 25, 2009 SULFO-POLYMER POWDER AND 0014. Yet another embodiment concerns a cosmetic com SULFO-POLYMER POWDER BLENDS WITH position, comprising the compositions described above and a CARRIERS AND/OR ADDITIVES cosmetically acceptable carrier. 0015. Another embodiment concerns a pharmaceutical or CROSS-REFERENCE TO RELATED agricultural composition, comprising the compositions APPLICATIONS described above and a pharmaceutically or agriculturally 0001. This application claims priority to U.S. Provisional acceptable carrier. Application Ser. No. 61/015.365, filed Dec. 20, 2007 the disclosure of which is incorporated herein by reference in its entirety. BRIEF DESCRIPTION OF THE DRAWINGS BACKGROUND OF THE INVENTION 0016 FIG. 1 shows a side-by-side comparison of a sul 0002 Sulfo-polyesters (such as Eastman AQ polymers) fopolyester polymer and the corresponding powder. are high molecular weight amorphous polyesters commonly 0017 FIG. 2 shows the chemical structures for various dispersed directly in water without the need to incorporate compound examples incorporated with Sulfopolyester poly organic co-solvents, Surfactants, or amines. Sulfo-polyesters mer powders. differ chiefly by their chemical makeup (i.e. they are com 0018 FIG. 3A shows the oral dose blood concentration posed of 5-sodiosulfoisophthalic acid (5-SSIPA) and various time data for itraconazole for two dosing groups; and combinations of other materials, for example: terephthalic 0019 FIG. 3B shows the oral dose blood concentration acid (TPA), isophthalic acid (IPA), ethylene glycol (EG), time data for hydroxy-itraconazole for two dosing groups. diethylene glycol (DEG), 1,4-cyclohexanedimethanol (CHDM), and/or 1,4-cyclohexanedicarboxylic acid (1,4- DETAILED DESCRIPTION CHDA). The temperature where a glassy polymer becomes rubbery on heating, and vice versa upon cooling, is known as 0020. The present invention concerns sulfo-polyester the glass transition temperature (T). Hence, the various powders and Sulfo-polyester blend powders, the incorpora sulfo-polyester polymers have different average T values. tion of carriers and/or actives, and methods of making the 0003 Sulfopolyesters are solid to semi-solid polymers powders as well as dispersions employing these powders. and require warm to hot water with Sufficient mixing time to 0021 Sulfo-polyester powder(s) and sulfo-polyester pow prepare concentrated dispersions. Moreover, different sulfo der blend(s) with and without carriers and/or actives are pre polyester polymer dispersions may possess trace volatile pared by dispersing said Sulfo-polyester powder(s) and Sulfo components and potentially cause odor. Therefore methods polyester powder blend(s) in a solvent or solvent mixture that improve dissolution and/or lower volatile content may be (e.g., water, water and alcohol mixtures, etc) at various tem advantageous. peratures. The exact solvent, or solvent mixture, and tempera BRIEF SUMMARY OF THE INVENTION tures used will be a function of the application end usage 0004. The present invention addresses solutions to issues and/or required dispersion percentage. End uses of said Sulfo previously described and enables the preparation of sul polyester powder(s) and sulfo-polyester powder blend(s) fopolyester polymer powders and/or blends containing carri include Sun care/skin care applications (i.e. creams, lotions ers (e.g. Surfactants) and/or actives, and dispersions of Sul and sprays), perfume applications (i.e. flavors, fragrances, fopolyester or sulfopolyester blends with and without carriers essential oils, etc), hairstyling applications (i.e. hair gel and and/or actives, having reduced odor, using water and/or sol hairspray), color makeup and hairstyling applications, drug vent mixtures with Sufficient mixing. delivery applications, and adhesive removal Such as re-pulp 0005. An embodiment of the present invention concerns a ing of paper and plastic and glass recycling. composition comprising at least one Sulfonated copolyester 0022. As used throughout this application, the term “pow and at least one active agent, wherein said composition is a der' shall mean particles in the range of 0.5-5000 uM. The powder. Science and technology of small particles is known as “micro 0006 Yet another embodiment concerns a method of metrics' (for a general review, see Physical Pharmacy and increasing the bioavailability of an active agent comprising Pharmaceutical Sciences Fifth Edition by Patrick J. Sinko, administering the composition described in the previous Lippincott Williams & Wilkins, 2006, ISBN: 0-7817-5027 paragraph to a subject (i.e. an organism). X). The unit commonly used to describe particle size is the 0007 Another embodiment concerns a method for pro micrometer (Lm). In general, optical microscopy may be used ducing a sulfonated copolyester powder containing an active to measure particle-sizes of about 0.2 to about 100 um; how agent comprising: ever, other techniques may also be used to determine approxi 0008 a) dispersing at least one sulfonated coployester and mate size ranges, such as sedimentation, coulter counter, at least one active agent in a solvent, or solvent mixture, to airpermeability, sieving, etc. form a dispersion; and 0023 Techniques such as sieving, according to methods of 0009 b) drying said dispersion to form a powder. the U.S. Pharmacopeia, may be used to determine powder 0010. Another embodiment concerns a method for pro fineness, or other properties of the corresponding powders ducing a sulfonated copolyester powder containing an active and/or powder blends; for example, particle size and size agent comprising: distribution (i.e. average particle size, particle-size distribu 0011 a) dispersing at least one sulfonated copolyester in a tion (frequency distribution curve), number and weight dis Solvent to form a dispersion; and tributions, particle number), particle Volume, particle shape 0012 b) drying said dispersion to form a powder; and and Surface area, pore size, porosity, particle density, bulki 0013 c) mixing (grinding, milling, and the like) said Sul ness, flow properties, etc. Because many powders have a fonated copolyester powder with at least one active agent. tendency to contain a non-symmetric particle size distribu US 2009/01 63449 A1 Jun. 25, 2009 tion, it is common to plot the log-normal distribution; com ture. Various methods to evaluate dissolution are well known; monly, this method results in a linear relationship. Subse for a general review, see Physical Pharmacy and Pharmaceu quently, the "geometric mean diameter” (d; the particle size tical Sciences Fifth Edition by Patrick J. Sinko, Lippincott equivalent to 50% on the probability scale) may be obtained Willams & Wilkins, 2006, ISBN: 0-7817-5027-X. Therefore, from plotting the logarithm of the particle size against the one should readily appreciate that the application end usage cumulative percent frequency on a probability Scale. There and/or required dispersion percentage would dictate the exact fore, as used throughout this application, powders shall be Solvent, or solvent mixture, and temperatures used to prepare classified into different particle size ranges, such as: dispersions from the powders. For example, a temperature of extremely fine powders (i.e. dusty powders: 0.5-50 um), about 70° C. to about 10°C., about 50° C. to about 15° C., or fine powders (50-100 um), 'coarse powders (100-1000 about 35° C. to about 18° C. maybe used. Typically, the um), and granular powders (1000-5000 um). mixtures are stirred at room temperature, or elevated tempera 0024. In an embodiment of the present invention, the com ture, until the sulfo-polyester powder or sulfo-polyesterpow positions are generally prepared by techniques such as lyo der blend becomes dispersed which can be a time period of philization, spray-drying, jet milling, spray freeze-drying, about 12 h to about 1 min, of about 6 h to about 5 min, or of fluidized-bed spray coating, Supercritical fluid methods, etc. about 2 h to about 15 min. The different techniques are based on different mechanisms 0030. As used throughout this application, the term “lipo of droplet/particle formation and/or 15 drying (for a general philic compounds' shall mean compounds having Solubility review, see Lyophilization of Biopharmaceuticals' edited by in water that is in the “sparingly soluble' range, or lower. Henry R. Costantino and Michael J. Pikal, AAPS Press, 2004, Persons of ordinary skill in the art will understand that, for ISBN: 0-9711767-6-0). compounds that are “sparingly soluble in water, the quantity 0025.