Water-soluble partially biodegradable dihydroxyalkyl cellulose
By reacting cellulose with diol compounds or ethylene oxide alkanol under alkaline conditions, dihydroxyalkyl cellulose with water-soluble partially biodegradable dihydroxyalkyl moiety of about 0.7 to 2.0 units of dihydroxyalkyl moiety/glucosan moiety is prepared, which solves the problem of insufficient simplicity and economicality of cellulose ether preparation process in the prior art, and achieves high efficient biodegradation and good water solubility of the product.
Patent Information
- Application Number
- CN202380070835.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-08-30
- Filing Date
- 2023-08-29
- Publication Date
- 2025-05-13
AI Technical Summary
In the prior art, the preparation process of cellulose ethers is insufficient in simplicity and economicality, the obtained products lack uniformity and solubility, and it is difficult to achieve better biodegradable properties.
By reacting cellulose with a diol compound or ethylene oxide alkanol under basic conditions, a water-soluble partially biodegradable dihydroxyalkyl cellulose with about 0.7 to 2.0 units of dihydroxyalkyl moiety/glucosyl moiety is prepared.
The combination of water solubility and partial biodegradable properties was achieved, and the product showed a biodegradation rate of ≥3% in aquatic media and complyed with the water solubility standard of OECD Test No. 105.
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Abstract
Description
Technical Field
[0001] One or more processes, steps, methods, products, results and / or concepts disclosed herein (hereinafter collectively referred to as "this application, this disclosure or the present invention") generally relate to a water-soluble, partially biodegradable dihydroxyalkyl cellulose, a method for producing the dihydroxyalkyl cellulose and uses thereof. Background Art
[0002] The present invention relates to a water-soluble partially biodegradable dihydroxyalkyl cellulose, and in particular, to a water-soluble partially biodegradable dihydroxyalkyl cellulose having a dihydroxyalkyl portion / anhydroglucose portion ratio of about 0.7 to about 2.0 units.
[0003] The European Chemicals Agency (ECHA) has recommended extensive restrictions on microplastics in products on the EU / EEA market to avoid or reduce their release into the environment. As companies around the world aim to eliminate all "avoidable" microplastics, "alternative plastics" such as bio-based plastics, biodegradable plastics and compostable plastics have become a new trend. In addition, chemically modified natural polymers have a huge share in the market. In particular, modified cellulose, modified other polysaccharides and other modified natural polymers are the main market drivers for biodegradable polymers, with many applications in healthcare, oilfield, personal care, electronics and home care.
[0004] Since the work of Lilienfeld and Dreyfus with cellulose ethers began in the 1920s, new derivatives of cellulose and modifications of known derivatives have been explored. Based on this research, carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, hydroxypropyl cellulose, and ethyl cellulose have developed into very important commercial products.
[0005] In early studies of preparing cellulose ethers, it was suggested that cellulose could be reacted with 3-chloro-1,2-propanediol to form ethers. See, for example, Dreyfus, U.S. Pat. No. 1,502,379 and Lilienfeld, U.S. Pat. No. 1,722,927. Both of these patents prepare so-called "oxyalkyl derivatives of cellulose" by reacting alkaline cellulose with the above-mentioned 3-chloro-1,2-propanediol. However, in each case, little is said about the properties of the products except that they are soluble in alkali or organic liquids but insoluble in water. Neither of these references states the level of substitution of these products.
[0006] Later, U.S. Pat. No. 2,572,039 to Klug et al. relates to the manufacture of cellulose ethers, and in particular, to improvements in the manufacture of hydroxyalkyl ethers of cellulose. Various methods have been proposed and used to prepare hydroxyalkyl derivatives of cellulose and other carbohydrates. Generally speaking, the processes proposed so far are insufficient in terms of simplicity and economy, and the products obtained also lack the desired uniformity and the desired solubility.
[0007] Canadian Patent Publication No. 1,095,029A discloses the reaction product of a cellulose ether and about 0.05 to 10 parts by weight of a reactant selected from the group consisting of borates, antimony salts, and readily saponifiable esters of boric acid per part of the cellulose ether, the cellulose ether being characterized in that: (a) the sole substitution on the cellulose is about 1.4 to 6 units of dihydroxypropyl per anhydroglucose unit, (b) it is soluble in water, and (c) it is thermoplastic.
[0008] US Patent No. 9782609 discloses dihydroxyalkyl substituted galactomannan polymers.More particularly, but not limited thereto, the disclosed and / or claimed inventive concepts also relate to optionally modifying substituted galactomannan polymers with cationic and / or hydrophobic moieties.
[0009] US Patent No. 4,096,326 discloses a cellulose ether having at least about 1.4 units of dihydroxypropyl per anhydroglucose unit, the cellulose ether being characterized by being soluble in water and having thermoplastic properties.
[0010] In view of the above, there is still a need for a water-soluble partially biodegradable dihydroxyalkyl cellulose having better biodegradability and solubility properties.
[0011] Surprisingly, it has been found that dihydroxyalkyl celluloses having from about 0.7 to about 2.0 units of dihydroxyalkyl moieties per anhydroglucose moieties have water solubility and are partially biodegradable.
[0012] Accordingly, the present invention is directed to a water-soluble, partially biodegradable dihydroxyalkyl cellulose having from about 0.7 to about 2.0 units of dihydroxyalkyl moieties per anhydroglucose moieties. Summary of the invention
[0013] The main aspect of the present application is to provide a water-soluble partially biodegradable dihydroxyalkyl cellulose having a dihydroxyalkyl moiety / anhydroglucose moiety of about 0.7 to about 2.0 units.
[0014] Another aspect of the present application provides a dihydroxyalkyl cellulose having a dihydroxyalkyl portion / anhydroglucose portion of about 0.7 to about 2.0 units, having a biodegradability of ≥3% in an aquatic medium when measured by the Organization for Economic Cooperation and Development (OECD) Test No. 301 or 302, and meeting the criteria of the water solubility method OECD Test No. 105 with a threshold level of 2 g / L.
[0015] Another non-limiting aspect of the present application discloses a dihydroxyalkyl cellulose having at least one anionic functional moiety, a cationic functional moiety, or a hydrophobic functional moiety.
[0016] Another aspect of the present application discloses a method for preparing water-soluble partially biodegradable dihydroxyalkyl cellulose.
[0017] Another aspect of the present application provides a method for preparing a water-soluble partially biodegradable dihydroxyalkyl cellulose having at least one anionic functional moiety, cationic functional moiety or hydrophobic functional moiety.
[0018] Another aspect of the present application provides a composition comprising a water-soluble partially biodegradable dihydroxyalkyl cellulose having a dihydroxyalkyl moiety / anhydroglucose moiety of about 0.7 to about 2.0 units and one or more ingredients.
[0019] Another aspect of the present application discloses a personal care composition comprising: (a) from about 0.1% (w / w) to about 20% (w / w) of a water-soluble, partially biodegradable dihydroxyalkyl cellulose, and (b) from about 80% (w / w) to about 99.9% (w / w) of one or more personal care ingredients. DETAILED DESCRIPTION
[0020] Before explaining in detail at least one aspect of the disclosed and / or claimed inventive concept, it should be understood that the disclosed and / or claimed inventive concept is not limited in its application to the construction and arrangement of components, or the details of steps or methods set forth in the following specification or shown in the accompanying drawings. The disclosed and / or claimed inventive concept can be used in other aspects or practiced or implemented in a variety of ways. In addition, it should be understood that the words and terms used herein are for descriptive purposes only and should not be considered limiting.
[0021] As used in accordance with the present disclosure, the following terms shall be understood to have the following meanings, unless otherwise indicated.
[0022] Unless otherwise defined herein, the technical terms used in connection with the disclosed and / or claimed inventive concepts shall have the meanings commonly understood by those of ordinary skill in the art. In addition, unless otherwise required by the context, singular terms shall include plural terms and plural terms shall include the singular.
[0023] The singular indefinite articles ("a", "an") and definite articles ("the") include the plural forms unless the context clearly dictates otherwise or there is a clear contrary implication in the context of the reference. The terms "comprising / comprises of" include more restrictive terms such as "consisting essentially of" and "consisting of".
[0024] For purposes of the following detailed description, except in any operating examples or where otherwise indicated, the numerical values expressing, for example, quantities of ingredients used in the specification and claims are to be understood as being modified in all instances by the term "about". The numerical parameters set forth in the specification and appended claims are approximations that may vary depending upon the desired properties to be obtained in practicing the present invention.
[0025] All percentages, parts, ratios and proportions used herein are by weight of the total composition, unless otherwise specified. All such weights pertaining to listed ingredients are based on the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified.
[0026] All publications, articles, treatises, patents, patent publications, and other references cited herein are incorporated in their entirety for all purposes to the extent consistent with the disclosure herein.
[0027] The use of the term "at least one" will be understood to include one and any number more than one, including but not limited to 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, 50, 100, etc. The term "at least one" can extend up to 100 or 1000 or more, depending on the terms to which it is attached.
[0028] Furthermore, the amount of 100 / 1000 should not be considered limiting as lower or higher limits may also produce satisfactory results.
[0029] As used herein, the words "comprising" (and any form thereof, such as the infinitive (comprise) and the third person singular (comprises)), "having" (and any form thereof, such as the infinitive (have) and the third person singular (has)), "including" (and any form thereof, such as the third person singular (includes) and the infinitive (include)), or "containing" (and any form thereof, such as the third person singular (contains) and the infinitive (contain)) are inclusive or open-ended, and do not exclude additional, unrecited elements or method steps.
[0030] The term "each independently selected from the group consisting of..." means that when a group occurs more than once in a structure, the group can be independently selected at each occurrence.
[0031] As used herein, the term "OECD test" refers to test standards and methods developed and validated by the Organization for Economic Cooperation and Development (OECD).
[0032] As used herein, the term "water-soluble" refers to water solubility as measured by OECD Test Method No. 105, wherein said method provides a threshold level of solubility of 2 g / L.
[0033] As used herein, the term "partially biodegradable" refers to the rate of biodegradation in aquatic media when measured by OECD Test No. 301 or 302 methods.
[0034] As used herein, the term "cellulose" refers to a homopolymer of β(1→4) linked D-glucose units that form linear chains and have the following structure:
[0035]
[0036] Cellulose can contain from a few hundred to a few thousand or more glucose units, making cellulose a polysaccharide. Cellulose is found in many natural products, such as the cell walls of plants and thus in wood, pulp, and cotton, among others.
[0037] As used herein, the term "β(1→4)" or "β-1,4-glucosidic bond" refers to a covalent bond connecting glucose molecules to each other through carbon 1 and carbon 4 on adjacent glucose monomers in glucan.
[0038] The term "glucan" herein refers to a polysaccharide of D-glucose monomers linked by glucosidic bonds, which is a type of glycosidic bond.
[0039] The terms "glycosidic linkage", "glycosidic bond", etc. are used interchangeably herein and refer to a covalent bond that connects one carbohydrate molecule to another carbohydrate molecule. The terms "glucosidic linkage", "glucosidic bond", etc. are used interchangeably herein and refer to a glycosidic bond between two glucose molecules in a dextran.
[0040] As used herein, the term "sugar" refers to sugars such as monosaccharides, disaccharides, oligosaccharides or polysaccharides. Monosaccharides include, but are not limited to, glucose, ribose and fructose. Disaccharides include, but are not limited to, sucrose and lactose. Polysaccharides include, but are not limited to, cellulose, hemicellulose and lignocellulose or starch. Other sugars are also useful within the scope of the present invention.
[0041] In one non-limiting embodiment, the present application is directed to a water-soluble partially biodegradable dihydroxyalkyl cellulose having a dihydroxyalkyl moiety / anhydroglucose moiety of about 0.7 to about 2.0 units.
[0042] According to another embodiment, the present application is directed to a dihydroxyalkyl cellulose, wherein the dihydroxyalkyl cellulose has from about 1.0 to about 1.7 units of dihydroxyalkyl moieties per anhydroglucose moieties.
[0043] According to another embodiment, the dihydroxyalkyl cellulose has about 0.7 to about 0.8 units, about 0.9 to about 1.0 units, about 1.1 to about 1.2 units, about 1.3 to about 1.4 units, about 1.5 to about 1.6 units, about 1.7 to about 1.8 units, about 1.9 to about 2.0 units of dihydroxyalkyl moieties per anhydroglucose moiety.
[0044] According to another embodiment, the dihydroxyalkyl cellulose has a molecular weight ranging from about 10,000 Daltons to about 1,500,000 Daltons.
[0045] In one non-limiting embodiment, the dihydroxyalkyl cellulose has a molecular weight ranging from about 40,000 Daltons to about 1,200,000 Daltons.
[0046] According to another embodiment, the dihydroxyalkyl cellulose has a molecular weight range of about 10,000 Daltons to about 20,000 Daltons, about 20,000 Daltons to about 30,000 Daltons, about 30,000 Daltons to about 40,000 Daltons, about 40,000 Daltons to about 50,000 Daltons, about 50,000 Daltons to about 60,000 Daltons, about 60,000 Daltons to about 70,000 Daltons, about 70,000 Daltons to about 80,000 Daltons, about 80,000 Daltons to about 90,000 Daltons, and about 90,000 Daltons to about 100,000 Daltons.
[0047] According to another embodiment, the dihydroxyalkyl cellulose has a molecular weight range of about 100,000 Daltons to about 200,000 Daltons, about 200,000 Daltons to about 300,000 Daltons, about 300,000 Daltons to about 400,000 Daltons, about 400,000 Daltons to about 500,000 Daltons, about 500,000 Daltons to about 600,000 Daltons, about 600,000 Daltons to about 700,000 Daltons, about 700,000 Daltons to about 800,000 Daltons, about 800,000 Daltons to about 900,000 Daltons, and about 900,000 Daltons to about 1000,000 Daltons.
[0048] According to another embodiment, the dihydroxyalkylcellulose has a molecular weight range of about 10,00,000 Daltons to about 11,00,000 Daltons, about 11,00,000 Daltons to about 12,00,000 Daltons, about 12,00,000 Daltons to about 13,00,000 Daltons, about 13,00,000 Daltons to about 14,00,000 Daltons, about 14,00,000 Daltons to about 15,00,000 Daltons.
[0049] According to another embodiment, the dihydroxyalkylcellulose is selected from the group consisting of dihydroxyethylcellulose, dihydroxypropylcellulose, dihydroxybutylcellulose and dihydroxypentylcellulose.
[0050] According to another embodiment, the dihydroxyalkylcellulose is dihydroxypropylcellulose.
[0051] According to another embodiment, the dihydroxyalkylcellulose exhibits a partial biodegradation rate of ≥ 3% in aquatic media when measured by OECD Test No. 301 or 302.
[0052] According to another embodiment, it is contemplated that the dihydroxyalkylcellulose exhibits a biodegradation rate of ≥3%, ≥5%, ≥10%, ≥15%, 20%, ≥25%, ≥30%, ≥35%, ≥40%, ≥45%, ≥50%, ≥55%, ≥60%, ≥65%, ≥70%, ≥75% or ≥80% in an aquatic medium when measured by OECD Test Method No. 301 or 302.
[0053] According to another embodiment, the water solubility of the dihydroxyalkylcellulose meets the threshold value of 2 g / liter according to OECD Test Method No. 105.
[0054] According to another embodiment, the dihydroxyalkylcellulose is functionalized with at least one anionic, cationic, or hydrophobic functional moiety.
[0055] According to another non-limiting embodiment, the anionic functional moiety is an alkenyl succinic anhydride. According to a non-limiting embodiment, the alkenyl succinic anhydride is selected from the group consisting of octenyl succinic anhydride, dodecenyl succinic anhydride and hexacenyl succinic anhydride.
[0056] According to another embodiment, the cationic functional moiety is selected from the group consisting of glycidyl trimethylammonium chloride, glycidyl trimethylammonium bromide, glycidyl trimethylammonium iodide, glycidyl trimethylammonium sulfate, glycidyl trimethylammonium acetate, glycidyl triethylammonium chloride, glycidyl triethylammonium bromide, glycidyl tripropylammonium chloride, glycidyl tributylammonium chloride, glycidyl triisopropylammonium chloride, N-3,4-dimethylammonium chloride, -Epoxybutyltrimethylammonium chloride, N-3,4-epoxybutyltriethylammonium bromide, N-4,5-epoxypentyltrimethylammonium chloride, dimethylamino-2,3-epoxypropane, diethylamino-2,3-epoxypropane, dibutylamino-2,3-epoxypropane, methylethylamino-2,3-epoxypropane, diethylamino-3,4-epoxybutane, dimethylamino-4,5-epoxypentane), and 3-chloro-2-hydroxypropyltrimethylammonium chloride.
[0057] According to another embodiment, the hydrophobic functional moiety is one or more C4-C 22 Alkyl radicals.
[0058] According to one non-limiting embodiment, C4-C 22 The alkyl radical is selected from the group consisting of: C4-C 22 Alkyl dihydroxyalkyl cellulose, C4-C 22 3-Hydroxyalkyl dihydroxyalkyl cellulose, C4-C 22 Alkyl succinate-modified dihydroxyalkyl cellulose, C4-C22 Alkenyl dihydroxyalkyl cellulose, and C4-C 22 Alkonic esterified dihydroxyalkyl cellulose, C4-C 22 Alkyl cationic dihydroxyalkyl cellulose and combinations thereof.
[0059] According to another embodiment, the water-soluble partially biodegradable dihydroxyalkyl cellulose is prepared by a method comprising the following steps: (a) alkalizing cellulose with a caustic aqueous solution at a temperature of about 10°C to about 50°C; (b) adding a diol compound or an oxiranylalkanol compound to the result of step (a), and heating the result at a temperature of about 50°C to about 150°C for about 1 to about 8 hours to obtain low-substituted dihydroxyalkyl cellulose; (c) cooling the result of step (b) to about 20°C to about 60°C. (d) heating the result of step (c) to a temperature of about 50°C to about 150°C for about 1 hour to about 8 hours to obtain the desired substituted dihydroxyalkyl cellulose, wherein optionally, the diol and caustic aqueous solution are added; (e) cooling the result of step (d) to a temperature of about 20°C to about 40°C for about 1 hour to about 3 hours, and adjusting the pH to about 5.5 to about 8.5; and (f) filtering, washing, drying and grinding the result of step (e) to obtain the desired dihydroxyalkyl cellulose.
[0060] According to another embodiment, the method for preparing a cationic, anionic or hydrophobic functionalized dihydroxyalkyl cellulose comprises the following steps: a) mixing about 5% (w / w) to 45% (w / w) of dihydroxyalkyl cellulose, about 20% (w / w) to 70% (w / w) of IPA, about 5% (w / w) to 50% (w / w) of water and about 1% (w / w) to 15% (w / w) of caustic in a flask and stirring for about 0.1 hour to 1 hour; b) adding about 1% (w / w) to 30% (w / w) of caustic to the result of (a); The method comprises the steps of: adding a cationic agent, anionic agent or hydrophobic agent (wt / wt) to a mixture of (a) and (b) and heating the mixture to a temperature of about 30° C. to 120° C. for about 1 to about 16 hours; c) lowering the temperature of the result of (b) to room temperature, neutralizing the result with 50% (wt / wt) to 100% (wt / wt) of an acid, and washing with 50% (wt / wt) to 100% (wt / wt) of IPA, acetone or methanol of different strengths; and d) drying the result in an oven at a temperature of about 30° C. to about 80° C. to recover the cationic, anionic or hydrophobic functionalized dihydroxyalkyl cellulose. According to another embodiment, the cellulose is selected from the group consisting of wood pulp and cotton linters.
[0061] According to another embodiment, the caustic solution is prepared from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate.
[0062] According to another embodiment, the diol compound is selected from the group consisting of oxirane alkanols, glycerol monohalohydrins, and combinations thereof.
[0063] According to another embodiment, the glycerol monohalohydrin is selected from the group consisting of 3-chloro-1,2-propanediol, 3-bromo-1,2-dihydroxypropanediol, 3-iodo-1,2-dihydroxypropanediol, 3-tosyl-1,2-dihydroxypropanediol, and combinations thereof.
[0064] According to a non-limiting embodiment, the oxiranyl alkanol compound is selected from the group consisting of oxiranyl methanol (glycidol), oxiranyl ethanol, oxiranyl propylene alcohol, oxiranyl butyl alcohol, oxiranyl pentanol, 2-(1-ethoxyethoxy)-2-(2-oxiranyl)ethanol and combinations thereof.
[0065] According to another embodiment of the present application, the present invention is directed to a personal care composition comprising: (a) from about 0.1% (w / w) to about 20% (w / w) of the water-soluble, partially biodegradable dihydroxyalkyl cellulose of the claimed invention, and (b) from about 80% (w / w) to about 99.9% (w / w) of one or more personal care ingredients.
[0066] According to another embodiment, the personal composition is a hair care composition, a skin care composition, a shampoo composition, an oral care composition, or a body wash composition.
[0067] According to another embodiment, the personal care ingredient is selected from the group consisting of surfactants, fatty acid soaps, hair and skin conditioning agents, suspending aids, emollients, emulsifiers, rheology modifiers, thickeners, vitamins, hair growth promoters, self-tanning agents, sunscreens, skin whitening agents, anti-aging compounds, anti-wrinkle compounds, anti-cellulite compounds, anti-acne compounds, anti-dandruff agents, antiperspirants, deodorants, hair fixatives, particulates, abrasives, moisturizers, antioxidants, keratolytic agents, antistatic agents, foam boosters, hydrotropes, solubilizers, pH adjusters, chelating agents, buffers, botanicals, hair colorants, hair dyes, oxidizing agents, reducing agents, hair and skin bleaching agents, pigments, anti-caries agents, anti-tartar agents, anti-plaque agents, solvents, and combinations thereof. According to another embodiment of the present application, the present invention is directed to a hair care composition comprising: (a) about 0.1% (w / w) to about 20% (w / w) of a water-soluble, partially biodegradable dihydroxyalkyl cellulose, and (b) about 80% (w / w) to about 99.9% (w / w) of one or more hair care ingredients.
[0068] According to another embodiment of the present application, the body wash composition comprises: (a) about 0.1% (weight / weight) to about 10% (weight / weight) of a water-soluble, partially biodegradable dihydroxyalkyl cellulose, and (b) about 90% (weight / weight) to about 99.9% (weight / weight) of one or more ingredients.
[0069] In addition, some aspects of the present application are described in detail by the following examples. The examples given herein are for illustrating the present application and are not intended to limit it.
[0070] Example
[0071] Example 1: Cellulose (45 g) is alkalized with an aqueous / IPA caustic solution (2.5%; 600 g) at a temperature of 20°C. Then, a diol compound or an ethylene oxide alkanol compound (35 g) is added to the resultant of the above step, and the resultant is heated at a temperature of 60°C for 1 hour to obtain a low-substituted dihydroxyalkyl cellulose. The low-substituted dihydroxyalkyl cellulose is cooled to a temperature of 40°C, and then an additional amount of caustic solution (10.2 g caustic) and a diol compound (60 g) are added. The above resultant is heated to a temperature of 60°C for 1 hour to obtain the desired substituted dihydroxyalkyl cellulose. The obtained dihydroxyalkyl cellulose is cooled to a temperature of 30°C for 1 hour, and the pH of the above reactants is adjusted to about 5.5 to about 8.5. The obtained dihydroxyalkyl cellulose is filtered, washed, dried and ground to obtain the desired dihydroxyalkyl cellulose.
[0072] Table 1: Dihydroxyalkyl celluloses with different units of dihydroxyalkyl moiety / anhydroglucose moiety
[0073]
[0074]
[0075] Example 2: Example 1 was repeated by changing the amounts of the chemicals described in Table 1 to obtain the dihydroxyalkyl cellulose of Example 2.
[0076] Biodegradability Test (OECD Test No. 301): This test guide describes six methods that can be used to screen chemicals for rapid biodegradability in aerobic aqueous media.
[0077] OECD Test No. 302: This test guide describes six methods that can be used to screen chemicals for rapid biodegradability in aerobic aqueous media.
[0078] Solubility Test (OECD Test No. 105): This test guide describes the method for determining the water solubility of a test substance.
[0079] Molecular Weight Determination: The average molecular weight of each sample was determined using gel permeation chromatography.
[0080] Although the compositions and methods of the disclosed and / or claimed inventive concepts have been described in specific aspects, it is obvious to those skilled in the art that the compositions and / or methods described herein and the steps or step sequences of the methods may be varied without departing from the concept, spirit and scope of the disclosed and / or claimed inventive concepts. All such similar substitutions and modifications apparent to those skilled in the art are deemed to be within the spirit, scope and concept of the disclosed and / or claimed inventive concepts.
Claims
1. A water-soluble, partially biodegradable dihydroxyalkyl cellulose having from about 0.7 to about 2.0 units of dihydroxyalkyl moieties per anhydroglucose moiety.
2. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose has from about 1.0 to about 1.7 units of dihydroxyalkyl moieties per anhydroglucose moieties.
3. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose has a molecular weight range of about 10,000 Daltons to about 1,500,000 Daltons.
4. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose has a molecular weight range of about 40,000 Daltons to about 1,200,000 Daltons.
5. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose is selected from the group consisting of dihydroxyethyl cellulose, dihydroxypropyl cellulose, dihydroxybutyl cellulose and dihydroxypentyl cellulose.
6. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose is dihydroxypropyl cellulose.
7. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkylcellulose exhibits a partial biodegradation rate of ≥ 3% in aquatic media when measured by OECD Test No. 301 or 302.
8. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose showed signs of biodegradation within 60 days or within 28 days.
9. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose meets the standard of water solubility method OECD test No. 105 with a threshold level of 2 g / L.
10. The dihydroxyalkyl cellulose according to claim 1, wherein The dihydroxyalkyl cellulose is further functionalized with at least one anionic functional moiety, cationic functional moiety, or hydrophobic functional moiety.
11. The dihydroxyalkyl cellulose according to claim 10, wherein The anionic functional moiety is alkenyl succinic anhydride.
12. The dihydroxyalkyl cellulose according to claim 11, wherein The alkenyl succinic anhydride is selected from the group consisting of octenyl succinic anhydride, dodecenyl succinic anhydride and hexadecenyl succinic anhydride.
13. The dihydroxyalkyl cellulose according to claim 10, wherein The cationic functional part is selected from the group consisting of glycidyl trimethylammonium chloride, glycidyl trimethylammonium bromide, glycidyl trimethylammonium iodide, glycidyl trimethylammonium sulfate, glycidyl trimethylammonium acetate, glycidyl triethylammonium chloride, glycidyl triethylammonium bromide, glycidyl tripropylammonium chloride, glycidyl tributylammonium chloride, glycidyl triisopropylammonium chloride, N-3,4-epoxybutyl trimethylammonium chloride, N-3,4-epoxybutyltriethylammonium bromide, N-4,5-epoxypentyltrimethylammonium chloride, dimethylamino-2,3-epoxypropylene, diethylamino-2,3-epoxypropylene, dibutylamino-2,3-epoxypropylene, methylethylamino-2,3-epoxypropylene, diethylamino-3,4-epoxybutylene, dimethylamino-4,5-epoxypentane, and 3-chloro-2-hydroxypropyltrimethylammonium chloride.
14. The dihydroxyalkyl cellulose according to claim 10, wherein The hydrophobic functional part is one or more C4-C 22 Alkyl radicals.
15. The dihydroxyalkyl cellulose according to claim 14, wherein The hydrophobic functional part is selected from the group consisting of: C4-C 22 Alkyl dihydroxyalkyl cellulose, C4-C 22 3-Hydroxyalkyl dihydroxyalkyl cellulose, C4-C 22 Alkyl succinate-modified dihydroxyalkyl cellulose, C4-C 22 Alkenyl dihydroxyalkyl cellulose, and C4-C 22 Alkyl esterified dihydroxyalkyl cellulose, C4-C 22 Alkyl cationic dihydroxyalkyl cellulose and combinations thereof.
16. A method for preparing the water-soluble partially biodegradable dihydroxyalkyl cellulose according to claim 1, comprising the following steps: a) alkalizing cellulose with an aqueous caustic solution at a temperature; b) adding a diol compound or an oxirane alkanol compound to the resultant of step (a), and heating the resultant at a temperature of about 50° C. to about 150° C. for about 1 to about 8 hours to obtain a low-substituted dihydroxyalkyl cellulose; c) cooling the result of step (b) to a temperature of about 20° C. to about 60° C.; d) heating the result of step (c) to a temperature of about 50° C. to about 150° C. for about 1 hour to about 8 hours to obtain the desired substituted dihydroxyalkyl cellulose, wherein optionally, the diol and caustic aqueous solution are added; e) cooling the result of step (d) to a temperature of about 20° C. to about 40° C. for about 1 hour to about 3 hours, and adjusting the pH to about 5.5 to about 8.5; and f) filtering, washing, drying and grinding the resultant of step (e) to obtain the desired dihydroxyalkyl cellulose of claim 1.
17. A method for preparing functionalized dihydroxyalkyl cellulose, comprising the following steps: a) mixing dihydroxyalkyl cellulose, isopropyl alcohol (IPA), water and caustic in a flask and stirring for about 0.1 hour to 1 hour to form a swollen resultant; b) adding an aqueous solution of a cationic agent, anionic agent or hydrophobic agent to the result of (a), and heating the mixture to a temperature of about 30° C. to 80° C. for about 1 to about 10 hours; and c) lowering the temperature of the resultant of (b) to room temperature, neutralizing the resultant with an acid, and washing with IPA, acetone or methanol of varying strengths; as well as d) drying the result of step (c) at a temperature of about 30° C. to about 80° C. to recover the functionalized dihydroxyalkyl cellulose containing a cationic portion, an anionic portion or a hydrophobic portion.
18. A method for preparing a hydrophobic functionalized dihydroxyalkyl cellulose, comprising the following steps: a) mixing about 5% (w / w) to 45% (w / w) of dihydroxyalkyl cellulose, about 20% (w / w) to 70% (w / w) of IPA, about 5% (w / w) to 50% (w / w) of water, and about 1% (w / w) to 15% (w / w) of caustic in a flask and stirring for about 0.1 hour to 1 hour; b) adding about 1% (w / w) to 30% (w / w) of a cationic agent, anionic agent or hydrophobic agent to the result of (a) and heating the mixture to a temperature of about 30° C. to 120° C. for about 1 to about 16 hours; and c) cooling the temperature of the product obtained in (b) to room temperature, adding 50% (weight / weight) to The product of step (b) is neutralized with 100% (w / w) acid and washed with IPA, acetone or methanol of different strengths ranging from 50% (w / w) to 100% (w / w); as well as d) drying the result of step (c) in an oven at a temperature of about 30° C. to about 80° C. to recover the cationic, anionic or hydrophobic functionalized dihydroxyalkyl cellulose.
19. The method of claim 16(a), wherein: The cellulose is selected from the group consisting of wood pulp and cotton linters.
20. The method according to claim 16, wherein: The caustic solution is prepared from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and combinations thereof.
21. The method according to claim 16, wherein: The diol compound is selected from the group consisting of oxirane alkanols, glycerol monohalohydrins, and combinations thereof.
22. The method according to claim 21, wherein: The glycerol monohalohydrin is selected from 3- Chloro-1,2-propylene glycol, 3-bromo-1,2-dihydroxypropylene glycol, 3-iodo-1,2-dihydroxypropylene glycol, The group consisting of 3-tosyl-1,2-dihydroxypropylene glycol and combinations thereof.
23. The method according to claim 21, wherein: The oxiranyl alkanol compound is selected from the group consisting of oxiranyl methanol (glycidol), oxiranyl ethanol, oxiranyl propylene alcohol, oxiranyl butyl alcohol, oxiranyl pentyl alcohol, 2-(1-ethoxyethoxy)-2-(2-oxiranyl)ethanol and combinations thereof.
24. A personal care composition comprising: a) from about 0.1% (w / w) to about 20% (w / w) of the water-soluble, partially biodegradable dihydroxyalkyl cellulose of claim 1, and b) from about 80% (w / w) to about 99.9% (w / w) of one or more personal care ingredients.
25. The personal composition of claim 24, wherein: The composition is a hair care composition, a skin care composition, a shampoo composition, an oral care composition or a body wash composition.
26. The personal composition of claim 24, wherein: The personal care ingredients are selected from the group consisting of surfactants, fatty acid soaps, hair and skin conditioning agents, suspending aids, emollients, emulsifiers, rheology modifiers, thickeners, hair growth promoters, self-tanning agents, sunscreens, skin whitening agents, anti-aging compounds, anti-wrinkle compounds, anti-cellulite compounds, anti-acne compounds, anti-dandruff agents, antiperspirants, deodorants, hair fixatives, particulates, abrasives, humectants, antioxidants, keratolytic agents, antistatic agents, foam boosters, hydrotropes, solubilizers, chelating agents, pH adjusters, chelating agents, buffers, botanicals, hair dyes, hair dyes, oxidizing agents, reducing agents, hair and skin bleaching agents, pigments, anti-caries agents, anti-tartar agents, anti-plaque agents, solvents, rheology modifiers, and combinations thereof.
27. A hair care composition comprising: a) from about 0.1% (w / w) to about 20% (w / w) of the water-soluble, partially biodegradable dihydroxyalkyl cellulose of claim 1, and b) from about 80% (w / w) to about 99.9% (w / w) of one or more hair conditioning ingredients.
28. A shower gel composition comprising: a) from about 0.1% (w / w) to about 10% (w / w) of the water-soluble, partially biodegradable dihydroxyalkyl cellulose of claim 1, and b) from about 90% (w / w) to about 99.9% (w / w) of one or more ingredients.
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