Cellulose esters and cellulose ester fibers with recovered components from multiple sources

Abstract

The cellulose esters and / or cellulose ester fibers are produced from at least two different feedstocks, each having one or more recovered components from waste materials. The resulting cellulose ester and / or cellulose ester fiber has a higher recovery fraction than when only one of the raw materials used to make it has a recovery fraction.

Description

Background Art 1. Technical Field

[0001] The present application generally relates to the production of cellulose esters and cellulose ester fibers having recycled content.

[0002] 2. Description of the Prior Art

[0003] Dissolving grade wood pulp raw materials are commonly used to make the cellulose fibers used in consumer textiles. While there are sustainably managed forests from which to obtain at least some of the required wood pulp supply, this is not ideal. Additionally, the global textile industry generates large amounts of waste textiles each year that end up in landfills or incineration. Technologies are needed to reduce the use of wood pulp while also reducing landfill impacts and polluting incineration processes. Summary of the invention

[0004] In one embodiment, the present disclosure provides a method comprising reacting an esterifying agent with cellulose to form a cellulose ester. At least a portion of the cellulose is derived from a first waste material and at least a portion of the esterifying agent is derived from a second waste material. The resulting cellulose ester has recycled components from both the cellulose and the esterifying agent used to prepare the cellulose ester.

[0005] In another embodiment, the present disclosure provides a method for preparing recycled content cellulose ester fiber. The method includes (a) providing a first raw material having recycled content derived from textile waste; (b) providing a second raw material having recycled content derived from waste plastic; (c) synthesizing a recycled content cellulose ester material from at least the first raw material and the second raw material, so that the recycled content cellulose ester material has recycled content derived from textile waste and waste plastic; and (d) spinning the recycled content cellulose ester material to produce recycled content cellulose ester fiber having recycled content derived from textile waste and waste plastic.

[0006] In yet another embodiment, the present disclosure provides a method for preparing recycled content cellulose ester fiber, wherein the method comprises (a) esterifying recycled content cellulose with a recycled content esterifying agent, thereby producing an initial cellulose ester material with recycled content from the recycled content cellulose and the recycled content esterifying agent; (b) optionally, hydrolyzing the initial cellulose ester material, thereby producing a hydrolyzed cellulose ester material; and (c) spinning at least one of the initial cellulose ester material and the hydrolyzed cellulose ester material, thereby producing recycled content cellulose ester fiber with recycled content from the recycled content cellulose and the recycled content esterifying agent.

[0007] In another embodiment, the present disclosure provides a recycled content cellulose ester fiber formed from a cellulose ester material having repeating units of the following structure:

[0008]

[0009] wherein the six-membered ring is a glucose ring and R1, R2 and R3 are independently selected from hydrogen or a linear alkanoyl group having 2 to 10 carbon atoms. DS of cellulose ester material 乙酰基 In the range of 1.5 to 2.95, 2.0 to 2.65 or 2.25 to 2.55. DS of cellulose ester material OH In the range of 0.5 to 1.5, 0.3 to 1.4 or 2.25 to 2.55. At least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the alkanoyl groups are recycled component alkanoyl groups derived from waste plastics, and at least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the glucose rings are recycled component glucose rings derived from textile waste.

[0010] In another embodiment, the present disclosure provides an article comprising cellulose ester fibers having recycled content. DETAILED DESCRIPTION

[0011] The present application is generally directed to a method for preparing cellulose esters, which produces a cellulose ester material having recycled content from two or more of the raw materials used to prepare the cellulose esters. In one embodiment, the method utilizes pre-consumer textile waste as at least one of the raw materials used to prepare the recycled content cellulose esters. In one embodiment, the disclosed method includes reacting an esterifying agent with a cellulose pulp derived from pre-consumer textile waste to form a cellulose ester, wherein both the esterifying agent and the cellulose pulp have recycled content derived from the waste.

[0012] Pre-consumer textile waste can be waste generated by the commercial textile industry during processing of cotton-based fibers, such as during clothing, fabric and / or yarn manufacturing. Pre-consumer textile waste can include any secondary material from any step in the manufacturing process: combing to the final manufacturing step of a specific process. Waste generated by the commercial textile industry during the start-up and / or shutdown of the manufacturing process and / or during the transition to new materials. Pre-consumer textile waste can be distinguished from post-consumer textile waste because the latter includes clothing that is manufactured and passed to consumers and / or used by consumers. Pre-consumer textile waste can include, consist essentially of, or consist of, one or more of cotton linters, bottom combed cotton, fabric clippings, cattle feed waste, comber rags, broken end suction device waste, defective waste, yarn waste, production waste, cutter clippings, twisting waste, or a mixture thereof.

[0013] After the raw cotton is removed by ginning or other separation processes, ginning leaves short cellulose fibers on the cotton seeds. These fibers are called cotton linters, and cotton linters are pre-consumer textile waste that can be used as dissolving pulp, as described in this disclosure.

[0014] In the cotton textile spinning process, short fibers, seed waste and stems are removed prior to the spinning process. The opening and combing equipment used in the process has a filter extraction system to remove and collect these particles. In the process of separating the quality fibers from the foreign particles, some fibers are usually still captured. Bottom combed cotton includes this fiber and is a pre-consumer textile waste that can be used to prepare cellulose esters as described herein.

[0015] Each textile cutting operation has a pattern cut from a standardized width of fabric, leaving fabric scraps that do not become part of the final garment and may be discarded as waste. Many of these fabrics are originally formed from cellulosic materials. Fabric clippings such as these are pre-consumer textile waste that can be used to prepare cellulose esters as described herein. T-shirt clippings are an example of fabric clippings suitable for use as pre-consumer textile waste.

[0016] Cattle feed waste includes heavy seed cotton and stem cotton which is less useful than bottom combed cotton. Comber rag includes fine cotton, but the short fibers are 1 / 2 inch (1.27 cm) or shorter. End-break wick waste includes fibers collected during processing while drawing or spinning.

[0017] Defective waste includes reprocessed fabric that is cut into smaller pieces and re-torn into fibers. Yarn waste includes waste generated by substandard (e.g., abnormal or unusual) or cut packages. Twist waste includes waste captured during multi-end twisting and / or final package winding.

[0018] Production waste includes material that is substandard (e.g., color difference, wrong fabric weight, broken needles, etc.) Cutter trimmings include material from the cutting pattern that is not used to make a garment.

[0019] In one embodiment, the pre-consumer textile waste can be in the form of dissolving pulp. The dissolving pulp can be provided in the form of rolls or sheets, and the rolls or sheets can contain cellulose from more than one source of pre-consumer textile waste and / or cellulose from sources other than pre-consumer textile waste, such as bamboo, switchgrass, hemp, juice industry waste (such as waste left over from a pulping process), sugarcane bagasse, or mixtures thereof.

[0020] In one embodiment or in combination with any of the other mentioned embodiments, at least 1 wt%, at least 20 wt%, at least 50 wt%, at least 70 wt%, at least 85 wt%, at least 90 wt% or at least 100 wt% of the cellulose in the dissolving pulp will come from pre-consumer textile waste sources.

[0021] Prior to acetylation, the rolls or sheets of dissolving pulp may be mechanically conditioned. Mechanical conditioning may include breaking the rolls or sheets into smaller pieces (e.g., shredding, chopping). Additionally, multiple rolls or sheets of the same or different types (e.g., having cellulose from different sources, as described above) may be mechanically conditioned to form smaller pieces and combined with the smaller pieces obtained from pre-consumer textile waste dissolving pulp.

[0022] In one embodiment or in combination with any of the other mentioned embodiments, the pre-consumer textile waste dissolving pulp will contain no more than 3 wt%, no more than 2 wt%, no more than 1 wt%, no more than 0.5 wt%, no more than 0.1 wt% or no more than 0 wt% surfactant molecules (charged or uncharged), based on the total weight of the pre-consumer textile waste dissolving pulp.

[0023] In one embodiment or in combination with any of the other mentioned embodiments, the pre-consumer textile waste dissolving pulp will contain no more than 3 wt%, no more than 2 wt%, no more than 1 wt%, no more than 0.5 wt%, no more than 0.1 wt% or no more than 0 wt% silicon atoms, based on the total weight of the pre-consumer textile waste dissolving pulp.

[0024] In one embodiment, the pre-consumer textile waste dissolving pulp will contain no more than 3 wt%, no more than 2 wt%, no more than 1 wt%, no more than 0.5 wt%, no more than 0.1 wt% or no more than 0 wt% of a combination of silicon atoms and surfactant molecules, based on the total weight of the pre-consumer textile waste dissolving pulp.

[0025] In one embodiment or in combination with any of the other mentioned embodiments, the pre-consumer textile waste dissolving pulp will have one, two, three, four, five, six, seven, eight, nine, ten, eleven or twelve properties of Table A in any combination. In one embodiment or in combination with any of the other mentioned embodiments, the pre-consumer textile waste dissolving pulp will have all thirteen properties of Table A.

[0026] Table A

[0027]

[0028]

[0029] Regardless of the source of pre-consumer textile waste, cellulose esters can be produced by any method known in the art. Dissolving pulp can be soaked, such as by dissolving the pulp in water, acetic acid and / or glacial acetic acid, to swell the fibers, which can increase chemical reactivity. If mechanical conditioning is performed, soaking can be performed after the mechanical conditioning. In one embodiment, soaking can be performed at a temperature of at least 15°C, at least 17°C, at least 20°C, at least 23°C, at least 25°C, at least 27°C, or at least 30°C and / or no more than 65°C, no more than 63°C, no more than 60°C, no more than 57°C, no more than 55°C, no more than 53°C, or no more than 50°C. In one embodiment or in combination with any other mentioned embodiments, soaking can be performed for 30 minutes to 90 minutes or 50 minutes to 70 minutes. In embodiments where the pulp is dissolved in water, dehydration can be performed before esterification.

[0030] Suitable esterification agents may include acetylating agents such as acetic anhydride.In one embodiment or in combination with any of the other mentioned embodiments, a catalyst (eg, sulfuric acid), an organic acid (eg, acetic acid), or both a catalyst and acetic acid will be present during acetylation.

[0031] As discussed above, at least a portion of the esterifying agent may be derived from waste material, so that the resulting cellulose ester has recycled components from the esterifying agent, as well as recycled components from a waste cellulose source (e.g., textile waste). In one embodiment, at least a portion of the esterifying agent is derived from recycled component synthesis gas. Recycled component synthesis can be performed by carbon reforming (e.g., gasification) of one or more raw materials containing waste materials and / or having recycled components. A method for providing recycled component synthesis gas is disclosed in U.S. Patent Application Publication No. US20220119987A1, and the entire disclosure of the patent application is incorporated herein by introduction to the extent consistent with the present disclosure. Other methods for providing recycled component synthesis gas are disclosed in U.S. Patent Application Publication No. 20200247910A1, and the entire disclosure of the patent application is incorporated herein by introduction to the extent consistent with the present disclosure. U.S. Patent Application Publication Nos. US20220119987A1 and 20200247910A1 are also included here as Appendix A and B, respectively.

[0032] In one embodiment or in combination with any of the other mentioned embodiments, the esterifying agent has recycled content derived from waste plastics. The recycled content from waste plastics can be provided, for example, by (i) carbon reforming the waste plastics to provide a synthesis gas having recycled content from waste plastics, or (ii) pyrolyzing the waste plastics to produce a pyrolysis effluent having recycled content from waste plastics, and then carbon reforming at least a portion of the pyrolysis effluent to provide a synthesis gas having recycled content from waste plastics.

[0033] In one embodiment or in combination with any of the other mentioned embodiments, at least a portion of the recovered component synthesis gas from carbon reforming can be reacted in the presence of a catalyst to form recovered component methanol. The recovered component methanol can then be carbonylated to form recovered component acetic acid and / or recovered component acetic anhydride. All or part of the acetic acid / anhydride can be used as an esterifying agent and / or in an esterification process.

[0034] In one embodiment or in combination with any of the other mentioned embodiments, the acetylation may be carried out at a temperature of at least 5° C., at least 7° C., at least 10° C., at least 13° C., at least 15° C., at least 20° C., or at least 25° C. and / or at a temperature of no more than 95° C., no more than 93° C., no more than 90° C., no more than 85° C., no more than 80° C., no more than 75° C., or no more than 70° C. In one embodiment or in combination with any of the other mentioned embodiments, the acetylation may be carried out for 10 minutes to 3 hours or 15 minutes to 2 hours.

[0035] The foregoing process will produce a cellulose triester (e.g., cellulose triacetate). In embodiments where a secondary ester (e.g., cellulose diacetate) is desired, the reaction solution may be subjected to a partial hydrolysis reaction, which converts the cellulose triacetate to cellulose diacetate. The process may include adding water to the triacetate solution and heating to at least 40°C, at least 45°C, at least 50°C, at least 55°C, at least 60°C, or at least 65°C and / or no more than 100°C, no more than 95°C, no more than 90°C, no more than 85°C, no more than 80°C, or no more than 75°C. In one embodiment or in combination with any of the other mentioned embodiments, the hydrolysis may be carried out for 4 to 25 hours or 5 to 20 hours. In one embodiment or in combination with any of the other mentioned embodiments, the hydrolysis may be carried out in the presence of an acid catalyst (e.g., sulfuric acid).

[0036] Cellulose esters formed as described herein generally comprise repeating units of the following structure:

[0037]

[0038] Where R 1 , R 2 and R 3 Independently selected from hydrogen or a straight chain alkanoyl group having 2 to 10 carbon atoms. Exemplary alkanoyl groups include acetyl, propionyl and / or butyryl.

[0039] For cellulose esters, the level of substitution is typically expressed as the degree of substitution ("DS"), which is the average number of non-OH substituents per anhydroglucose unit ("AGU"). In general, conventional cellulose contains three hydroxyl groups per AGU unit that can be substituted; therefore, the value of DS can range from zero to three. However, due to the contribution of the end groups, low molecular weight cellulose esters can have a total degree of substitution slightly higher than 3. Since DS is a statistical average, a value of 1 does not guarantee that there is one substituent for each AGU. In some cases, there may be unsubstituted AGUs, some with two substituents, and some with three substituents. "Total DS" is defined as the average number of all substituents per AGU and typically this value is a non-integer. The degree of substitution for each AGU can also refer to a specific substituent, such as, for example, hydroxyl, acetyl, butyryl, or propionyl.

[0040] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester has a DS of at least 1.5, at least 1.55, at least 1.6, at least 1.65, at least 1.7, at least 1.75, at least 1.8, at least 1.85, at least 1.9, at least 1.95, at least 2.0, at least 2.05, at least 2.1, at least 2.15, at least 2.2, at least 2.25, at least 2.3, at least 2.35, or at least 2.38 and / or no more than 2.95, no more than 2.9, no more than 2.8, no more than 2.7, no more than 2.6, no more than 2.55, no more than 2.5, or no more than 2.45. 乙酰基 In certain embodiments, the cellulose esters may have a DS in the range of 2.7 to 2.95, 1.5 to 2.6, 1.6 to 2.6, 1.7 to 2.6, 1.8 to 2.6, 1.9 to 2.6, 2.0 to 2.6, 2.05 to 2.6, 2.1 to 2.6, 2.15 to 2.6, 2.2 to 2.6, 2.25 to 2.55, 2.3 to 2.5, or 2.38 to 2.45. 乙酰基 .

[0041] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester has a DS of at least 0.05, at least 0.1, at least 0.2, at least 0.3, at least 0.4, or at least 0.5 and / or no more than 1.5, no more than 1.4, no more than 1.3, no more than 1.2, no more than 1.1, or no more than 1.0. OH In certain embodiments, the cellulose ester has a DS in the range of 0.05 to 1.5, 0.1 to 1.5, 0.2 to 1.4, 0.3 to 1.2, 0.4 to 1.1, or 0.5 to 1.0. OH .

[0042] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester has a DS of at least 0.1, at least 0.2, or at least 0.3 and / or no more than 1.5, no more than 1.4, no more than 1.3, no more than 1.2, no more than 1.1, no more than 1.0, no more than 0.9, no more than 0.8, no more than 0.7, no more than 0.6, no more than 0.5, or no more than 0.4. 丁酰基 In certain embodiments, the cellulose ester has a DS in the range of 0.1 to 1.5, 0.1 to 1.2, 0.1 to 0.8, 0.1 to 0.4, 0.2 to 1.5, 0.2 to 1.2, 0.2 to 0.8, 0.2 to 0.4, 0.3 to 1.5, 0.3 to 1.2, 0.3 to 0.8, or 0.3 to 0.6. 丁酰基 .

[0043] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester has a DS of at least 0.1, at least 0.2, or at least 0.3 and / or no more than 1.5, no more than 1.4, no more than 1.3, no more than 1.2, no more than 1.1, no more than 1.0, no more than 0.9, no more than 0.8, no more than 0.7, no more than 0.6, no more than 0.5, or no more than 0.4. 丙酰基 In certain embodiments, the cellulose ester has a DS in the range of 0.1 to 1.5, 0.1 to 1.2, 0.1 to 0.8, 0.1 to 0.4, 0.2 to 1.5, 0.2 to 1.2, 0.2 to 0.8, 0.2 to 0.4, 0.3 to 1.5, 0.3 to 1.2, 0.3 to 0.8, or 0.3 to 0.6. 丙酰基 .

[0044] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester has a total DS of at least 1.5, at least 1.55, at least 1.6, at least 1.65, at least 1.7, at least 1.75, at least 1.8, at least 1.85, at least 1.9, at least 1.95, at least 2.0, at least 2.05, at least 2.1, at least 2.15, at least 2.2, at least 2.25, at least 2.3, at least 2.35 or at least 2.38 and / or no more than 2.95, no more than 2.9, no more than 2.85, no more than 2.8, no more than 2.75, no more than 2.7, no more than 2.65, no more than 2.6, no more than 2.55, no more than 2.5 or no more than 2.45. In certain embodiments, the cellulose esters may have a total DS in the range of 1.5 to 2.95, 1.6 to 2.85, 1.7 to 2.8, 1.8 to 2.75, 1.9 to 2.7, 2.0 to 2.65, 2.05 to 2.6, 2.1 to 2.6, 2.15 to 2.6, 2.2 to 2.6, 2.25 to 2.55, 2.3 to 2.5, or 2.38 to 2.45.

[0045] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester may be cellulose diacetate and / or cellulose triacetate. Alternatively, in certain embodiments, the cellulose ester may include mixed cellulose esters, such as cellulose acetate butyrate or cellulose acetate propionate.

[0046] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester may have a degree of acetylation of at least 30 wt%, at least 35 wt%, or at least 40 wt%, and / or no more than 62.5 wt%, no more than 60 wt%, no more than 55 wt%, no more than 50 wt%, or no more than 45 wt%. In certain embodiments, the cellulose ester may have a degree of acetylation in the range of 30 wt% to 62.55 wt%, 35 wt% to 55 wt%, 35 wt% to 50 wt%, 35 wt% to 45 wt%, 40 wt% to 62.55 wt%, 40 wt% to 60 wt%, 40 wt% to 55 wt%, 40 wt% to 50 wt%, or 40 wt% to 45 wt%.

[0047] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester may have a hydroxyl content of at least 0.3 wt%, at least 0.5 wt%, at least 1 wt%, at least 2 wt%, at least 3 wt%, or at least 4 wt%, and / or no more than 20 wt%, no more than 15 wt%, no more than 10 wt%, or no more than 5 wt%. In certain embodiments, the cellulose ester may have a hydroxyl content in the range of 0.3 wt% to 20 wt%, 0.5 wt% to 20 wt%, 2 wt% to 15 wt%, 3 wt% to 10 wt%, or 4 wt% to 5 wt%.

[0048] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a number average degree of polymerization of at least 100, at least 110, at least 120, at least 130, at least 140, at least 150, at least 160, at least 170, at least 180, at least 190, at least 200, at least 210, at least 220, at least 230, at least 240, at least 250, at least 260, or at least 265. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a molecular weight of no more than 1,000, no more than 900, no more than 800, no more than 700, no more than 600, no more than 500, no more than 400, no more than 350, no more than 325, no more than 300, no more than 290, no more than 280, no more than 270, no more than 260, no more than 250, no more than 240, no more than 230, no more than 220, no more than 210, no more than 200, no more than 190, no more than 180, no more than 170, no more than 160, no more than 150, no more than 149, no more than 148, no more than 150, no more than 160, no more than 17 ... 147, not more than 146, not more than 145, not more than 144, not more than 143, not more than 142, not more than 141, not more than 140, not more than 139, not more than 138, not more than 137, not more than 136, not more than 135, not more than 134, not more than 133, not more than 132, not more than 131, not more than 130, not more than 129, not more than 128, not more than 127, not more than 126, not more than 125, not more than 124, not more than 123, not more than 122, not more than 121, not more than 120, not more than 119, not more than 118, not more than 117, not more than 116 or not more than 115. In certain embodiments, the cellulose esters may have a number average degree of polymerization in the range of 100 to 1,000, 100 to 500, 100 to 400, 100 to 300, 100 to 250, 100 to 200, 100 to 150, 100 to 135, 100 to 200, 100 to 150, 100 to 135, 100 to 180, 100 to 150, 100 to 145, 100 to 140, 100 to 135, or 100 to 130.

[0049] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a number average absolute molecular weight of at least 5,000 Daltons, at least 10,000 Daltons, at least 15,000 Daltons, at least 20,000 Daltons, or at least 25,000 Daltons and / or no more than 75,000 Daltons, no more than 70,000 Daltons, no more than 65,000 Daltons, no more than 60,000 Daltons, no more than 55,000 Daltons, no more than 50,000 Daltons, no more than 45,000 Daltons, no more than 40,000 Daltons, no more than 35,000 Daltons, or no more than 30,000 Daltons as measured by gel permeation chromatography ("GPC") in accordance with ASTM D6474. In certain embodiments, the cellulose esters may have a number average absolute molecular weight ranging from 5,000 Daltons to 75,000 Daltons, from 10,000 Daltons to 65,000 Daltons, or from 15,000 Daltons to 35,000 Daltons as measured by GPC according to ASTM D6474.

[0050] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a weight average absolute molecular weight of at least 50,000 Daltons, at least 55,000 Daltons, at least 60,000 Daltons, at least 65,000 Daltons, at least 70,000 Daltons, at least 75,000 Daltons, at least 80,000 Daltons, or at least 85,000 Daltons and / or no more than 150,000 Daltons, no more than 140,000 Daltons, no more than 130,000 Daltons, no more than 120,000 Daltons, no more than 110,000 Daltons, no more than 100,000 Daltons, or no more than 95,000 Daltons as measured by GPC according to ASTM D6474. In certain embodiments, the cellulose esters may have a weight average absolute molecular weight in the range of 50,000 Daltons to 150,000 Daltons, 70,000 Daltons to 120,000 Daltons, or 80,000 Daltons to 95,000 Daltons as measured by GPC according to ASTM D6474.

[0051] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester may have a crystallinity of at least 1%, at least 2%, at least 5%, at least 10%, at least 15%, or at least 20%, as measured according to ASTM F2625. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester may have a crystallinity of no more than 25%, no more than 20%, no more than 15%, no more than 10%, no more than 9%, no more than 8%, no more than 7%, no more than 6%, no more than 5%, no more than 4%, no more than 3%, no more than 2%, or no more than 1%, as measured according to ASTM F2625. In certain embodiments, the cellulose ester may have a crystallinity of 1% to 99%, 1% to 50%, 1% to 30%, 1% to 20%, or 1% to 15%, as measured according to ASTM F2625.

[0052] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a glass transition temperature of at least 120°C, at least 125°C, at least 130°C, at least 135°C, at least 140°C, at least 145°C, at least 150°C, at least 155°C, at least 160°C, at least 165°C, at least 170°C or at least 175°C and / or no more than 250°C, no more than 245°C, no more than 240°C, no more than 235°C, no more than 230°C, no more than 225°C, no more than 220°C, no more than 215°C, no more than 210°C, no more than 205°C, no more than 200°C, no more than 195°C, no more than 190°C or no more than 185°C.

[0053] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a hemicellulose content of at least 0.1 wt%, at least 0.25 wt%, at least 0.5 wt%, at least 1 wt%, at least 2 wt%, at least 3 wt%, at least 4 wt%, at least 5 wt%, at least 6 wt%, or at least 7 wt%. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester can have a hemicellulose content of no more than 10 wt%, no more than 9 wt%, no more than 8 wt%, no more than 7 wt%, no more than 6 wt%, no more than 5 wt%, no more than 4 wt%, no more than 3 wt%, no more than 2 wt%, or no more than 1 wt%.

[0054] Whether cellulose triacetate or cellulose diacetate is the desired end product, cellulose ester flakes may be precipitated from solution, washed and dried.

[0055] In one embodiment or in combination with any of the other mentioned embodiments, at least 20%, at least 40%, at least 60%, at least 80%, or at least 100% by weight of the cellulose in the flakes may come from pre-consumer textile waste sources.

[0056] Then, the cellulose ester can be dissolved in a suitable solvent to form a spinning solution for wet spinning or dry spinning through a spinneret to form one or more spun fibers. In one embodiment, a cellulose ester (e.g., cellulose triacetate) can be melt-spun through a spinneret to form one or more spun fibers.

[0057] In one embodiment, the cellulose ester (I) prepared from pre-consumer waste textiles as described above can be the only cellulose ester added to the spinning solution or melt-spinning. In another embodiment, the cellulose ester (I) can be mixed or blended with a different cellulose ester flake (II) to form a blend of at least two different cellulose esters.

[0058] As an alternative to precipitation and dissolution in wet or dry spinning embodiments, the cellulose ester can be retained in an acid-based solution (i.e., an acidic spinning solution) and used directly in a downstream fiber wet or dry spinning process. In one embodiment, the acidic spinning solution can be derived solely from pre-consumer textile waste. In another embodiment, an acidic spinning solution from one or more other cellulose sources can be blended with an acidic spinning solution derived from pre-consumer textile waste.

[0059] In one embodiment or in combination with any other mentioned embodiment, the different cellulose esters (II) are not formed from cellulose derived from pre-consumer textile waste. The cellulose ester sheet (II) may be formed from a cellulosic material selected from wood pulp and / or other plant-based cellulose sources. Examples of other plant-based cellulose sources may include bamboo, switchgrass, hemp, juice industry waste (such as waste left over from a pulping process), bagasse, agricultural residues, or mixtures thereof.

[0060] In one embodiment or in combination with any of the other mentioned embodiments, at least 20 wt. %, at least 40 wt. %, at least 60 wt. %, at least 80 wt. % or at least 100 wt. % of the cellulose in the combination of cellulose ester (I) and cellulose ester (II) may come from pre-consumer textile waste sources.

[0061] In one embodiment or in combination with any of the other mentioned embodiments, if the pre-consumer textile waste comprises cotton linters, the blend of cellulose ester (I) and cellulose ester (II) comprises no more than 95 wt.-%, no more than 90 wt.-%, no more than 85 wt.-%, no more than 80 wt.-%, no more than 75 wt.-%, no more than 70 wt.-%, no more than 65 wt.-%, or no more than 60 wt.-% of cellulose ester formed from cellulose derived from cotton linters, based on the total weight of the flake blend.

[0062] In one embodiment or in combination with any of the other mentioned embodiments, cellulose ester can be added to the spinning solution so that the spinning solution comprises at least 5 wt%, at least 8 wt%, at least 10 wt%, at least 12 wt%, at least 15 wt%, at least 18 wt%, at least 20 wt%, or at least 22 wt% of cellulose ester, and / or no more than 35 wt%, no more than 33 wt%, no more than 30 wt%, no more than 29 wt%, no more than 25 wt%, no more than 22 wt%, or no more than 20 wt% of cellulose ester, based on the total weight of the spinning solution. In certain embodiments, the cellulose ester spinning solution comprises from 5 wt% to 35 wt%, from 10 wt% to 35 wt%, from 12 wt% to 35 wt%, from 15 wt% to 35 wt%, or from 25 wt% to 35 wt% of cellulose ester, based on the total weight of the spinning solution.

[0063] The dissolving solvent should be added in sufficient amount to effectively dissolve the cellulose ester, thereby forming a cellulose ester spinning solution. In one embodiment or in combination with any other mentioned embodiments, the cellulose ester spinning solution may contain at least 65 wt %, at least 70 wt %, at least 75 wt %, at least 80 wt %, at least 85 wt %, at least 90 wt %, or at least 95 wt %, or 99 wt % and / or no more than 99 wt %, no more than 95 wt %, no more than 90 wt %, or no more than 85 wt % of one or more dissolving solvents, based on the total weight of the spinning solution. In certain embodiments, the cellulose ester spinning solution contains 65 wt % to 99 wt %, 70 wt % to 95 wt %, 75 wt % to 95 wt %, 80 wt % to 95 wt %, or 90 wt % to 99 wt % of one or more dissolving solvents, based on the total weight of the spinning solution.

[0064] The dissolving solvent can be any solvent in which the particular cellulose ester is soluble. Examples of suitable dissolving solvents for cellulose diacetate include those selected from acetone, methylene chloride, alcohol (e.g., methanol, ethanol), tetrahydrofuran, dimethylformamide, dimethylacetamide, formamide, N-formylmorpholine, N-methyl-2-pyrrolidone, N-methylformamide, N-vinylacetamide, or N-vinylpyrrolidone, methyl ethyl ketone, cyclohexanone, diacetone alcohol, ethylene glycol diacetate, or mixtures thereof. Examples of suitable dissolving solvents for cellulose triacetate include those selected from chloroform, methylene chloride, alcohol (e.g., methanol, ethanol), dimethylacetamide, dimethylformamide, formamide, N-formylmorpholine, N-methyl-2-pyrrolidone, N-methylformamide, N-vinylacetamide, or N-vinylpyrrolidone, or mixtures thereof.

[0065] The water or moisture content of the spinning solution can be kept relatively low. In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester spinning solution has a moisture content of no more than 4 wt%, no more than 3.5 wt%, no more than 3 wt%, no more than 2.5 wt%, no more than 2 wt%, no more than 1.5 wt%, no more than 1.4 wt%, no more than 1.3 wt%, no more than 1.2 wt%, no more than 1.1 wt%, no more than 1 wt%, no more than 0.9 wt%, no more than 0.8 wt%, no more than 0.7 wt% or no more than 0.6 wt%, based on the total weight of the cellulose ester spinning solution.

[0066] Due to the type of cellulose ester and dissolving solvent used, the cellulose spinning solution can have a desired operating viscosity. In one embodiment or in combination with any other mentioned embodiments, when measured at the spinning temperature for making the fiber, the cellulose ester spinning solution can have a viscosity of at least 10 poise, at least 20 poise, at least 30 poise, at least 40 poise, at least 50 poise, at least 60 poise, at least 70 poise, at least 80 poise, at least 90 poise or at least 100 poise and / or no more than 3,000 poise, no more than 2,000 poise, no more than 1,500 poise, no more than 1,000 poise, no more than 950 poise, no more than 900 poise, no more than 850 poise, no more than 800 poise, no more than 750 poise, no more than 700 poise, no more than 650 poise, no more than 600 poise, no more than 550 poise or no more than 500 poise. This spinning temperature is nominally the temperature of the spinning solution passing through and entering the spinneret. The viscosity defined here is the "zero" shear viscosity obtained by extrapolation to very low shear rates when the viscosity is plotted against shear rate, or by using a Brookfield viscometer with a low spindle RPM. Therefore, the "when measured" threshold does not in any way reflect actual cellulose ester spinning dope usage or practice.

[0067] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester spinning solution may have a viscosity of at least 10 poise, at least 20 poise, at least 30 poise, at least 40 poise, at least 50 poise, at least 60 poise, at least 70 poise, at least 80 poise, at least 90 poise or at least 100 poise and / or no more than 5,000 poise, no more than 4,000 poise, no more than 3,000 poise, no more than 2,000 poise, no more than 1,500 poise, no more than 1,000 poise, no more than 950 poise, no more than 900 poise, no more than 850 poise, no more than 800 poise, no more than 750 poise, no more than 700 poise, no more than 650 poise, no more than 600 poise, no more than 550 poise or no more than 500 poise when measured at 25°C, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C or 110°C. It should be noted that the "when measured" standard does not require that the cellulose ester spinning solution be used only at the specified temperature; rather, the temperature standard simply provides a temperature threshold for measuring the viscosity of the cellulose ester spinning solution. Therefore, the "when measured" threshold does not reflect the use or practice of actual cellulose ester spinning solutions in any way. The viscosity can be measured using a Brookfield viscometer with a low spindle RPM.

[0068] In one embodiment or in combination with any other mentioned embodiment, the cellulose ester spinning solution may contain some additives or no additives in addition to the cellulose ester. Such additives may include, but are not limited to, plasticizers, antioxidants, heat stabilizers, pro-oxidants, inorganic substances, pigments, colorants, or combinations thereof.

[0069] In one embodiment or in combination with any of the other mentioned embodiments, the spinning solution comprises no more than 10 wt. %, no more than 5 wt. %, no more than 3 wt. %, no more than 2 wt. %, no more than 1 wt. % or 0 wt. % of polymers other than cellulose esters, based on the total solids in the spinning solution.

[0070] In one embodiment or in combination with any other mentioned embodiments, the spinning solution comprises no more than 10 wt %, no more than 5 wt %, no more than 3 wt %, no more than 2 wt %, no more than 1 wt % or 0 wt % additives based on the total solids in the spinning solution. Examples of such additives include metal oxides, matting agents, plasticizers, water, biodegradation enhancers and / or fiber lubricants. Depending on the embodiment, when the total weight of one, two, three, four, five or all of the metal oxides, matting agents, plasticizers, water, biodegradation enhancers and / or fiber lubricants is combined in the spinning solution, the spinning solution has any one or more of the above-mentioned wt % ranges.

[0071] In one embodiment or in combination with any of the other mentioned embodiments, the spinning solution comprises no more than 10 wt. %, no more than 5 wt. %, no more than 3 wt. %, no more than 2 wt. %, no more than 1 wt. % or 0 wt. % of a combination of additives and polymers that are not cellulose esters, based on the total solids in the spinning solution.

[0072] In one embodiment or in combination with any other mentioned embodiments, the spinning solution is prepared by mixing the cellulose ester, the solvent and any other components at a relatively low temperature. In certain embodiments, the mixing is carried out by mixing at a temperature of at least 45°C, at least 46°C, at least 47°C, at least 48°C, at least 49°C, at least 50°C, at least 51°C, at least 52°C, at least 53°C, at least 54°C, at least 55°C, at least 56°C, at least 57°C, at least 58°C, at least 59°C or at least 60°C and / or no more than 140°C, no more than 130°C, no more than 120°C, no more than 110°C, no more than 105°C, no more than 104°C, no more than 103°C, no more than 102°C, no more than 101°C, no more than 100°C, no more than 99°C, no more than 98°C, no more than 97°C, no more than 96°C or no more than 95°C. In certain embodiments, the temperature is between 45°C and 140°C, between 45°C and 105°C, between 47°C and 103°C, or between 50°C and 100°C.

[0073] In one embodiment or in combination with any other mentioned embodiment, the mixing is carried out for at least 5 minutes, at least 6 minutes, at least 8 minutes, at least 10 minutes, at least 12 minutes, at least 14 minutes or at least 15 minutes and / or no more than 48 hours, no more than 36 hours, no more than 24 hours, no more than 20 hours, no more than 16 hours, no more than 12 hours or no more than 8 hours. In certain embodiments, the time is 5 minutes to 48 hours, 5 minutes to 36 hours, 5 minutes to 24 hours or 5 minutes to 8 hours.

[0074] After forming the cellulose ester spinning solution, it can be transported to an optional spinning solution storage tank for temporary storage and / or degassing. The spinning solution storage tank can include any conventional storage tank known in the art that can store cellulose ester spinning solution. When stored in the storage tank, the cellulose ester spinning solution can be subjected to conditions that are conducive to maintaining the physical properties of the spinning solution and / or removing the bubbles introduced during the mixing step. The temperature and pressure of the storage and / or degassing tank can be optimized as required to improve and maintain the quality of the cellulose ester spinning solution.

[0075] Next, the cellulose ester spinning solution can be pumped out from the spinning solution storage tank into a filter, which can remove any large and undesirable particles and gels from the cellulose ester spinning solution before spinning. The filter can include any conventional filter equipment and filter types known in the art. After filtering, the filtered cellulose ester spinning solution can be pumped to a spinneret, which is located near or in an evaporation chamber or evaporation cabinet for dry spinning, or near a coagulation bath for wet spinning.

[0076] The cellulose ester spinning solution can be metered through a spinneret to form one or more fibers. The shape and size of the one or more holes in the spinneret help determine the cross-section of the fiber. The number of holes in the spinneret surface determines the number of fibers that are formed simultaneously when the spinning solution is metered into the spinneret. When the spinning solution passes through the holes in the spinneret surface, a single fiber is formed.

[0077] More specifically, in one embodiment or in combination with any other mentioned embodiment, the cellulose ester spinning solution can be spun at a rate of 10 m / min to 1000 m / min through a spinneret hole having a design known in the art (e.g., having a hole area equivalent to a circular diameter of 20 microns to 200 microns). In one embodiment or in combination with any other mentioned embodiment, the spinneret can be maintained at a temperature of at least 50°C, at least 55°C, at least 60°C, at least 65°C, at least 70°C, or at least 75°C and / or no more than 175°C, no more than 170°C, no more than 165°C, no more than 160°C, no more than 155°C, or no more than 150°C. In certain embodiments, the head of the spinneret can be maintained at a temperature in the range of 50°C to 175°C, 75°C to 175°C, 85°C to 165°C, 95°C to 160°C, or 100°C to 150°C.

[0078] At the spinneret, the cellulose ester spinning solution can be extruded through a plurality of holes to form a continuous cellulose ester fiber. At the spinneret, the fiber can be stretched to form a plurality of single fibers, or hundreds of single fibers, or even a bundle of one thousand single fibers. Each bundle in these bundles can include at least 10, at least 20, at least 30, at least 40, at least 50, at least 60, at least 70, at least 80, at least 90, at least 100, at least 150, at least 200, at least 250, at least 300, at least 350 or at least 400 and / or be no more than 1,000, no more than 900, no more than 800, no more than 700 or no more than 600 fibers. The spinneret can be operated at any speed suitable for producing a single filament fiber, and then the single filament fiber is assembled into a bundle with a desired size and shape. As used herein, the term "single filament fiber" refers to the continuous filament initially produced by each hole in the spinneret surface.

[0079] For dry spinning, the fiber is extruded through a spinneret into a vertical spinning chamber, which may have walls nominally between 150°C and 240°C and may contain a gas nominally between 200°C and 500°C within the chamber, wherein the solvent is flashed or evaporated. In certain embodiments, evaporation comprises exposing the spun fiber to a temperature of at least 100°C, at least 110°C, at least 120°C, at least 130°C, at least 140°C, at least 145°C, at least 150°C, at least 153°C, at least 155°C, at least 160°C, at least 165°C, at least 170°C, at least 175°C, at least 180°C, at least 185°C, or at least 189°C and / or no more than 500°C, no more than 400°C, no more than 375°C, no more than 350°C, no more than 325°C, no more than 300°C, no more than 275°C, no more than 250°C, no more than 240°C, no more than 230°C, or no more than 220°C. In certain embodiments, the temperature is from 100°C to 500°C, 110°C to 400°C, 120°C to 375°C, 130°C to 350°C, 140°C to 300°C, or 150°C to 250°C.

[0080] For wet spinning, the fibers may be drawn through a coagulation bath comprising a coagulation solvent formed from water or a blend of water and an additional solvent.

[0081] It should be noted that the cellulose ester fibers formed can be in the form of monocomponent fibers formed from only one material (e.g., cellulose ester) or a uniformly blended composition and are therefore not considered "bicomponent" or "multicomponent fibers" which are characterized by internal phases or boundaries of different compositions delineated within the outer surface of the fiber. In one embodiment or in combination with any of the other mentioned embodiments, the resulting cellulose ester fibers can contain at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 99%, or at least 99.9% by weight of cellulose ester, based on the total weight of the fiber. In certain embodiments, the cellulose ester fibers can be formed entirely of cellulose ester.

[0082] The single cellulose ester fiber discharged from the spinneret can have any suitable cross-sectional shape.Exemplary cross-sectional shapes include, but are not limited to, circular or different from circular (non-circular).In one embodiment or in combination with any other mentioned embodiments, the single fiber discharged from the spinneret can have a substantially circular cross-sectional shape.As used herein, the term "cross section" generally refers to the cross section of the fiber measured perpendicular to the fiber elongation direction.Quantitative image analysis ("QIA") can be used to determine and measure the cross section of the fiber.

[0083] The cross-sectional shape of an individual fiber may also be characterized by its deviation from a circular cross-sectional shape. In some cases, the deviation may be characterized by the shape factor of the fiber, which is determined by the following formula: Shape Factor = Perimeter / (4π x Cross-sectional Area) 1 / 2 In some embodiments, the shape factor of a single cellulose ester fiber can be from 1 to 2, 1 to 1.8, 1 to 1.7, 1 to 1.5, 1 to 1.4, 1 to 1.25, 1 to 1.15, or 1 to 1.1. A fiber having a perfectly circular cross-sectional shape has a shape factor of 1. The shape factor can be calculated from the cross-sectional area of ​​the fiber, which can be measured using a QIA.

[0084] Furthermore, in certain embodiments, the cellulose ester fibers may be in the form of solid fibers (fibers having a solid cross-sectional shape without the presence of pores therein) rather than hollow fibers.

[0085] In one embodiment or in combination with any of the other mentioned embodiments, at least 20%, at least 40%, at least 60%, at least 80%, or at least 100% by weight of the cellulose in the fibers may come from pre-consumer textile waste sources.

[0086] In one embodiment or in combination with any of the other mentioned embodiments, according to ASTM The cellulose ester fibers and / or yarns produced therefrom can have a tenacity of at least 0.2 g / denier, at least 0.3 g / denier, at least 0.4 g / denier, at least 0.5 g / denier, at least 0.6 g / denier, at least 0.7 g / denier, at least 0.8 g / denier, at least 0.9 g / denier, at least 1 g / denier, at least 1.1 g / denier, at least 1.2 g / denier, at least 1.3 g / denier, at least 1.4 g / denier, at least 1.5 g / denier, at least 1.6 g / denier, at least 1.7 g / denier, at least 1.8 g / denier, at least 1.9 g / denier, or at least 2 g / denier and / or no more than 3.0 g / denier, or no more than 2.5 g / denier, no more than 2.3 g / denier, no more than 2.1 g / denier, no more than 2 g / denier, or no more than 1.9 g / denier, as measured by UL 22556.

[0087] Elongation, also known as elongation at break, is expressed as a percentage and it indicates the extent to which a yarn or filament will stretch before breaking. In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers and / or yarns produced therefrom may have an elongation at break of at least 10%, at least 15%, at least 16%, at least 17%, at least 18%, at least 19%, at least 20%, at least 21%, at least 22%, at least 23%, at least 24%, at least 25%, at least 26%, at least 27%, at least 28%, at least 29%, or at least 30%, as measured according to ASTM D22556.

[0088] The Silk Factor (SF) is an empirically determined relationship between tenacity and elongation that is used to predict the failure envelope of a given fiber. The Silk Factor can be used to characterize the suitability of a yarn or fiber for a given process and is calculated based on the following formula:

[0089]

[0090] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers and / or yarns produced therefrom may have a silk factor of at least 5.0, at least 6.0, at least 7.0, or at least 7.6, wherein elongation is defined as a percentage and tenacity is in grams per denier.

[0091] In one embodiment or in combination with any other mentioned embodiments, cellulose ester fibers and / or yarns formed therefrom can be biodegradable. As used herein, the term "biodegradable" generally refers to the tendency of a material to chemically decompose under certain environmental conditions. The degree of degradation can be characterized by the weight loss of a sample in a given time period exposed to certain environmental conditions. In some cases, cellulose ester fibers and / or yarns formed therefrom can have a weight loss of at least 5%, at least 10%, at least 15%, or at least 20% after being buried in soil for 60 days, and / or can have a weight loss of at least 15%, at least 20%, at least 25%, at least 30%, or at least 35% after being exposed in compost for 15 days. However, the degradation rate can vary according to the specific end use of the fiber. Exemplary test conditions are provided in U.S. Patent Nos. 5,870,988 and 6,571,802, which are incorporated herein by reference.

[0092] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers and / or yarns formed therefrom can be compostable. To be considered "compostable," a material must meet the following four criteria: (1) the material must be biodegradable; (2) the material must be disintegrable; (3) the material must not contain heavy metals in excess of a maximum amount; and (4) the material must not be ecotoxic. The term "disintegrable" refers to the tendency of a material to physically break down into smaller fragments when exposed to certain conditions. Disintegration depends on the material itself, as well as the physical size and construction of the item being tested. Ecotoxicity measures the effect of a material on plant life, and the heavy metal content of a material is determined according to procedures specified in standard test methods.

[0093] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers and / or yarns formed therefrom can be industrially compostable, home compostable, or both. In such embodiments, the cellulose ester fibers can meet four criteria: (1) biodegradable, in that at least 90% of the carbon component is converted within 180 days; (2) disintegratable, in that at least 90% of the material disintegrates within 12 weeks; (3) free of heavy metals exceeding the threshold value specified according to the EN 12423 standard; and (4) the disintegrated components support future plant growth as humus; wherein each of these four conditions is tested according to ASTM D6400, ISO 17088, or EN 13432 methods.

[0094] In one embodiment or in combination with any other mentioned embodiment, the cellulose ester fibers and / or yarns formed therefrom may exhibit at least 70% biodegradation within a period of no more than 50 days when tested under aerobic composting conditions according to ISO 14855-1 (2012) at ambient temperature (28°C ± 2°C). In some cases, the cellulose ester fibers and / or yarns formed therefrom may exhibit at least 70% biodegradation within a period of no more than 49 days, no more than 48 days, no more than 47 days, no more than 46 days, no more than 45 days, no more than 44 days, no more than 43 days, no more than 42 days, no more than 41 days, no more than 40 days, no more than 39 days, no more than 38 days, or no more than 37 days when tested under these conditions (also referred to as "home composting conditions"). These conditions may not be aqueous or anaerobic.

[0095] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers and / or yarns formed therefrom may exhibit at least 60% biodegradation within a period of no more than 45 days when tested under aerobic composting conditions at a temperature of 58° C. (± 2° C.) according to ISO 14855-1 (2012). In some cases, they may exhibit at least 60% biodegradation within a period of no more than 44 days when tested under these conditions (also referred to as “industrial composting conditions”). These may not be aqueous or anaerobic conditions.

[0096] The newly formed fiber can be accumulated onto a core or tube at a winder after evaporation or solvent flashing and can be sent to an optional downstream process. The fiber can be wound on a winding roll, which provides tension and pulls the fiber into the downstream steps of the process, which can include, for example, one or more annealing sections, winders, crimpers, cutters, or combinations thereof.

[0097] The formed cellulose ester fibers may be gathered into bundles, bands or yarns. The bundles, bands or yarns may contain a plurality of cellulose ester fibers. Each of these bundles, bands or yarns may contain at least 15, at least 20, at least 30, at least 40, at least 50, at least 60, at least 70, at least 80, at least 90, at least 100, at least 150, at least 200, at least 250, at least 300, at least 350 or at least 400 and / or no more than 70,000, no more than 60,000, no more than 50,000, no more than 40,000, no more than 30,000, no more than 20,000, no more than 15,000, no more than 10,000, no more than 5,000, no more than 1,000, no more than 900, no more than 800, no more than 700 or no more than 600 individual fibers.

[0098] In one embodiment or in combination with any of the other mentioned embodiments, cellulose ester fibers and / or cellulose ester bundles, ribbons or yarns may be passed through a curling zone in which a patterned wavy shape may be imparted to at least a portion or substantially all of the individual fibers. When used, the curling zone includes at least one curling device for mechanically curling the fibers. Typically, the cellulose ester fibers are ideally not curled by thermal or chemical means (e.g., a hot water bath, steam, air jets or chemical coatings), but rather mechanically curled using a suitable crimping machine. An example of a suitable type of mechanical crimping machine is a "stuffing box" or "stuffing box" crimping machine that utilizes multiple rollers to create friction, which causes the fibers to bend and form curls. Other types of crimping machines may also be suitable. Examples of suitable apparatus for imparting crimp to fibers are described, for example, in U.S. Patent Nos. 9,179,709; 2,346,258; 3,353,239; 3,571,870; 3,813,740; 4,004,330; 4,095,318; 5,025,538; 7,152,288; and 7,585,442, each of which is incorporated herein by reference to the extent not inconsistent with the present disclosure.

[0099] In one embodiment or in combination with any of the other mentioned embodiments, the curling can be performed so that the cellulose ester fibers have a curl frequency of at least 5, at least 7, at least 10, at least 12, at least 13, at least 15, or at least 17 and / or at most 30, at most 27, at most 25, at most 23, at most 20, or at most 19 curls per inch ("CPI") as measured according to ASTM D3937-12. In certain embodiments, the average CPI of fibers used to make cellulose ester tow, tape or yarn and / or various downstream products may be in the range of 7 to 30 CPI, 10 to 30 CPI, 10 to 27 CPI, 10 to 25 CPI, 10 to 23 CPI, 10 to 20 CPI, 12 to 30 CPI, 12 to 27 CPI, 12 to 25 CPI, 12 to 23 CPI, 12 to CPI, 15 to 30 CPI, 15 to 27 CPI, 15 to 23 CPI, 15 to 20 CPI, or 15 to 19 CPI.

[0100] In one embodiment or in combination with any of the other mentioned embodiments, when curled, the curl amplitude of the fiber can vary and can be, for example, at least 0.85 mm, 0.90 mm, 0.93 mm, 0.96 mm, 0.98 mm, 1.00 mm, or 1.04 mm. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the curl amplitude of the fiber can be at most 1.75 mm, at most 1.70 mm, at most 1.65 mm, at most 1.55 mm, at most 1.35 mm, at most 1.28 mm, at most 1.24 mm, at most 1.15 mm, at most 1.10 mm, at most 1.03 mm, or at most 0.98 mm.

[0101] Additionally, in one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester fibers, cellulose ester tows, tapes or yarns, and / or staple fibers produced therefrom may have a crimp ratio of at least 1:1. As used herein, "crimp ratio" refers to the ratio of the length of the uncrimped tow to the length of the crimped tow. In certain embodiments, the cellulose ester fibers, cellulose ester yarns, and / or staple fibers produced therefrom may have a crimp ratio of at least 1:1, at least 1.1:1, at least 1.125:1, at least 1.15:1, or at least 1.2:1.

[0102] The curl amplitude and curl ratio were measured according to the procedures outlined in U.S. Patent Application Publication No. 2020 / 0299822, which is incorporated herein by reference to the extent not inconsistent with the present disclosure.

[0103] Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, one or more types of surface finishes may be applied to the cellulose ester fibers and / or bundles, tapes, or yarns formed therefrom. The application method is not limited and may include the use of spraying, wick application, dipping, or the use of a squeeze roller, lick roller, or kiss roller. The location where the finish is applied to the fibers may vary depending on the function of the finish. For example, a lubricant finish may be applied after spinning and before crimping, or before the fibers are gathered into bundles. A cutting lubricant and / or an antistatic lubricant may be applied before or after crimping and before drying. A suitable amount of all finishes on the cellulose ester fibers, whether lubricants, cutting lubricants, antistatic finishes or other finishes, may be at least 0.01%, at least 0.02%, at least 0.05%, at least 0.10%, at least 0.15%, at least 0.20%, at least 0.25%, at least c.30%, at least 0.35%, at least 0.40%, at least 0.45%, at least 0.50%, at least 0.55%, or at least 0.60% yarn finish ("FOY") relative to the weight of the dry cellulose ester fibers. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the cumulative amount of finish may be present in an amount of no more than 2.5%, no more than 2.0%, no more than 1.5%, no more than 1.2%, no more than 1.0%, no more than 0.9%, no more than 0.8%, or no more than 0.7% FOY based on the total weight of the dry fibers. The amount of finish on the fibers (expressed as a weight percent) may be determined by solvent extraction. As used herein, "FOY" or "yarn finish" refers to the amount of finish on the fiber or yarn minus any added water.

[0104] In one embodiment or in combination with any other mentioned embodiment, the cellulose ester fiber may contain at least one plasticizer, or in an alternative, may not contain a plasticizer. Based on the total weight of the cellulose ester fiber, the cellulose ester fiber may contain less than 30% by weight, less than 12% by weight, less than 10% by weight, less than 9% by weight, less than 8% by weight, less than 7% by weight, less than 6% by weight, less than 5% by weight, less than 4% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight of at least one plasticizer. When present, the plasticizer may be incorporated into the fiber itself by spinning a spinning solution containing the plasticizer, the plasticizer being included in a sheet for preparing the spinning solution, and / or the plasticizer may be applied to the surface of the fiber or filament by any method for applying a finish. If desired, the plasticizer may be included in the finish formulation.

[0105] The resulting cellulose ester fibers can be used to produce a variety of intermediate fiber products, such as tow bands, staple fibers, filaments, bundles, slivers, tubes, rovings, yarns and / or bales, as well as final products, such as fabrics, textiles, woven articles (e.g., woven fabrics or textiles), nonwoven articles (e.g., nonwoven webs, fabrics or textiles), knitted textiles, tobacco filters and / or heat-not-burn tobacco products.

[0106] In one embodiment or in combination with any other mentioned embodiments, the above-mentioned cellulose ester fibers and / or cellulose ester yarns can be cut into staple fibers. Any suitable type of cutting device can be used, and the cutting device can cut the fibers into the desired length without excessively damaging the fibers. The example of the cutting device may include, but is not limited to, a rotary cutter, a paper cutter, an extension breaking device, a reciprocating blade or a combination thereof. Once cut, the cellulose ester staple fibers can be baled or otherwise bagged or packaged for subsequent transportation, storage and / or use. In one embodiment or in combination with any other mentioned embodiments, the d50 length of the staple fibers can be at least 10mm, at least 20mm, at least 30mm, at least 40mm or at least 50mm and / or no more than 450mm, no more than 400mm, no more than 350mm, no more than 300mm, no more than 250mm, no more than 200mm, no more than 150mm, no more than 115mm, no more than 110mm, no more than 105mm, no more than 100mm or no more than 95mm.

[0107] Additionally or alternatively, in one embodiment or in combination with any other mentioned embodiment, the denier per filament (weight in grams for 9000 m of fiber length) or "DPF" of cellulose ester fibers (whether cellulose ester staple fibers or cellulose ester continuous fibers) can be in the range of 0.5 to less than 30 or 0.5 to less than 20. The specific method for measuring is not limited and includes the ASTM 1577-07 method using the FAVIMAT vibrator procedure (if filaments of cut staple fibers can be obtained therefrom), microbalance weight measurement of samples of known length, or width analysis using any convenient optical microscope or analyzer. DPF can also be related to the maximum width of the fiber.

[0108] In one embodiment or in combination with any of the other mentioned embodiments, the staple fibers may form cellulose ester spun yarns. Spun yarns are continuous strands composed of staple fibers that are mechanically entangled by a staple yarn spinning process. The staple yarn spinning process may be, but is not limited to, ring spinning, open end spinning, air jet spinning, compact spinning, sirospinning, vortex spinning, worsted spinning, semi-worsted spinning, woolen spinning, and flax wet spinning.

[0109] In one embodiment or in combination with any other mentioned embodiments, the cellulose ester fibers can form nonwoven articles, such as nonwoven textiles. Exemplary nonwoven articles can include wet-laid nonwoven articles, air-laid nonwoven articles, carded articles, and / or dry-laid nonwoven articles.

[0110] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester yarn can be formed into a woven article, such as a woven textile. The woven textile can be formed on a loom by interlacing at least two yarns (warp and weft), wherein the warp yarn strands are oriented in parallel, and the weft yarns are oriented at an angle to the warp yarns, interlacing in an alternating pattern over and under the warp yarns.

[0111] In one embodiment or in combination with any of the other mentioned embodiments, the cellulose ester yarn can form a knitted article, such as a knitted textile. Such a knitted textile can be formed from interlocking yarn loops.

[0112] In one embodiment or in combination with any of the other mentioned embodiments, the final products described herein, including staple fibers, yarns, nonwoven articles, knitted articles, and woven articles, can comprise, consist essentially of, or consist of cellulose ester fibers. The final products described herein, including staple fibers, yarns, nonwovens, knitted articles, and woven articles, can contain at least 0.25%, at least 0.5%, at least 0.75%, at least 1%, at least 2%, at least 3%, at least 4%, at least 5%, at least 6%, at least 7%, at least 8%, at least 9%, at least 10%, at least 12%, at least 15%, at least 18%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 99%, or at least 99.9% by weight of one or more cellulose ester fibers, based on the total weight of the article. Additionally or alternatively, in one embodiment or in combination with any of the other mentioned embodiments, the final products described herein, including staple fibers, yarns, nonwovens, knitted articles, and woven articles, may contain no more than 99 wt%, no more than 95 wt%, no more than 90 wt%, no more than 85 wt%, no more than 80 wt%, no more than 75 wt%, no more than 70 wt%, no more than 65 wt%, no more than 60 wt%, no more than 55 wt%, no more than 50 wt%, no more than 45 wt%, no more than 40 wt%, no more than 35 wt%, no more than 30 wt%, no more than 25 wt%, no more than 20 wt%, no more than 15 wt%, no more than 10 wt%, no more than 9 wt%, no more than 8 wt%, no more than 7 wt%, no more than 6 wt%, or no more than 5 wt% of one or more cellulose ester fibers, based on the total weight of the article. In certain embodiments, the final product may be formed entirely from cellulose ester fibers, or contain one or more cellulose ester fibers in a range of 0.25% to 50%, 1% to 99%, 1% to 50%, 50% to 99%, 1% to 20%, or 0.25% to 5% by weight, based on the total weight of the article.

[0113] In one embodiment or in combination with any other mentioned embodiment, the final product described herein may have one, two, three or four of the properties of Table B in any combination. In one embodiment or in combination with any other mentioned embodiment, the final product will have all five properties of Table B.

[0114] Table B*

[0115]

[0116] * Determined as described in Example 3.

[0117] Each document in Table C is incorporated by reference in its entirety to the extent that it does not contradict the statements herein. In addition, any one or more embodiments disclosed in any one or more documents in Table C may be used in combination with each other and / or with one or more embodiments disclosed herein, as long as such combination does not contradict the statements made herein.

[0118] Table C

[0119]

[0120]

[0121]

[0122] The additional advantages of the various embodiments will be apparent to those skilled in the art upon reading the disclosure herein and the working examples below. It should be understood that the various embodiments described herein are not necessarily mutually exclusive unless otherwise specified herein. For example, a feature described or depicted in one embodiment may also be included in other embodiments, but is not necessarily included. Therefore, the present disclosure encompasses various combinations and / or integrations of the specific embodiments described herein.

[0123] Claims supporting the disclosure - first embodiment

[0124] In a first embodiment of the present technology, a method is provided, which includes reacting an esterifying agent with cellulose to form a cellulose ester, wherein at least a portion of the cellulose is derived from a first waste material and at least a portion of the esterifying agent is derived from a second waste material, wherein the cellulose ester has recycled components from the cellulose and the esterifying agent.

[0125] The first embodiment described in the preceding paragraphs may also include one or more of the additional aspects listed below. Each of the following additional aspects of the first embodiment may be an independent feature, or may be combined with one or more of the other additional aspects to the same degree. In addition, the following bulleted paragraphs may be considered as dependent claim features, with a level of subordination indicated by the degree of indentation in the bulleted list (i.e., features that are indented more than the features listed above are considered to be subordinate to the features listed above).

[0126] • Wherein at least one of the first waste material and the second waste material is textile waste.

[0127] • wherein said first waste material and said second waste material are different types of materials.

[0128] • wherein the first waste material is textile waste.

[0129] o wherein the textile waste is pre-consumer textile waste.

[0130] ■Wherein the second waste material is waste plastic.

[0131] - wherein at least a portion of said cellulose is derived from a renewable material, wherein said cellulose ester comprises a renewable component from said renewable material.

[0132] o Wherein the renewable material is wood pulp.

[0133] o wherein the first waste material is textile waste and the second waste material is plastic waste.

[0134] - wherein the total recycled content of the cellulose ester is at least 20%, at least 40%, at least 50% or at least about 60%.

[0135] o wherein the cellulose ester comprises at least 10%, at least 20%, at least 30%, or at least about 40% recycled content derived from the first waste material and at least 5%, at least 10%, at least 15%, or at least about 20% recycled content derived from the second waste material.

[0136] • wherein the first waste material is textile waste.

[0137] o wherein the textile waste is pre-consumer textile waste.

[0138] ○Wherein the second waste material is waste plastic.

[0139] - wherein at least a portion of said cellulose is derived from renewable materials, wherein said cellulose ester comprises at least 10%, at least 20%, at least 30% or about 40% renewable content.

[0140] o Wherein the renewable material is wood pulp.

[0141] ■Wherein the first waste material is textile waste.

[0142] ●Wherein the textile waste is pre-consumer textile waste.

[0143] ●Wherein the second waste material is waste plastic.

[0144] ●Wherein the first waste material is pre-consumer textile waste selected from cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, reject waste, yarn waste, production waste, cutter clippings, twisting waste or a mixture of two or more thereof.

[0145] o wherein the pre-consumer textile waste consists essentially of or consists of cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, reject waste, yarn waste, production waste, cutter clippings, twisting waste, or mixtures thereof.

[0146] - further comprising mechanically conditioning a dissolving pulp prior to said reacting, wherein said dissolving pulp comprises said cellulose.

[0147] o wherein the dissolving pulp is in the form of a sheet or roll and the mechanical conditioning comprises forming the sheet or roll into smaller pieces.

[0148] - Also comprising soaking the dissolving pulp in acetic acid and / or water prior to said reacting.

[0149] o wherein said soaking is performed after said mechanical conditioning.

[0150] • wherein the esterifying agent comprises an acetylating agent.

[0151] o wherein the acetylating agent comprises acetic anhydride.

[0152] • wherein the reaction is carried out in the presence of acetic acid, a catalyst or both acetic acid and a catalyst.

[0153] wherein the cellulose ester comprises cellulose triacetate, and further comprising hydrolyzing the cellulose triacetate to form cellulose diacetate

[0154] ● It also includes forming the cellulose ester into a cellulose ester sheet (I).

[0155] o Also comprising mixing the cellulose ester flakes (I) with cellulose ester flakes (II) to form a flake blend, wherein the cellulose ester flakes (II) are not formed from cellulose derived from pre-consumer textile waste.

[0156] ■ wherein the cellulose ester sheet (II) is formed from a cellulosic material selected from wood pulp, bamboo, switchgrass, hemp, juice industry waste, sugarcane bagasse or a mixture thereof.

[0157] ●Wherein, if the pre-consumer textile waste comprises cotton linters, the flake blend comprises no more than 95 weight percent, no more than 90 weight percent, no more than 85 weight percent, no more than 80 weight percent, no more than 75 weight percent, no more than 70 weight percent, no more than 65 weight percent or no more than 60 weight percent of cellulose esters formed from cellulose derived from cotton linters, based on the total weight of the flake blend.

[0158] The method further comprises spinning a cellulose ester spinning solution comprising the cellulose ester through a spinneret to prepare one or more spun fibers.

[0159] o Also comprising at least one of: evaporating solvent from the one or more spun fibers; or pulling the one or more fibers through a coagulation bath.

[0160] The method further comprises spinning a cellulose ester spinning solution comprising the cellulose ester through a spinneret to prepare one or more spun fibers.

[0161] o Also comprising at least one of: evaporating solvent from the one or more spun fibers; or pulling the one or more fibers through a coagulation bath.

[0162] ● wherein the cellulose ester has a number average degree of polymerization of at least 100, at least 110, at least 120, at least 130, at least 140, at least 150, at least 160, at least 170, at least 180, at least 190, at least 200, at least 210, at least 220, at least 230, at least 240, at least 250, at least 260 or at least 265.

[0163] ● wherein the cellulose ester has a molecular weight of not more than 1,000, not more than 900, not more than 800, not more than 700, not more than 600, not more than 500, not more than 400, not more than 350, not more than 325, not more than 300, not more than 290, not more than 280, not more than 270, not more than 260, not more than 250, not more than 240, not more than 230, not more than 220, not more than 210, not more than 200, not more than 190, not more than 180, not more than 170, not more than 160, not more than 150, not more than 149, not more than 148, not more than 147, not more than 146, not more than 145, not more than 144, not more than 143, not more than 142, not more than 141, not more than 140, not more than 139, not more than 138, not more than 137, not more than 136, not more than 135, not more than 134, not more than 133, not more than 132, not more than 131, not more than 130, not more than 129, not more than 128, not more than 127, not more than 126, not more than 125, not more than 124, not more than 123, not more than 122, not more than 121, not more than 120, not more than 119, not more than 118, not more than 117, not more than 116 or not more than 115.

[0164] ● wherein the cellulose ester has a DS acetyl of at least 1.5, at least 1.55, at least 1.6, at least 1.65, at least 1.7, at least 1.75, at least 1.8, at least 1.85, at least 1.9, at least 1.95, at least 2.0, at least 2.05, at least 2.1, at least 2.15, at least 2.2, at least 2.25, at least 2.3, at least 2.35 or at least 2.38 and / or no more than 2.95, no more than 2.9, no more than 2.8, no more than 2.7, no more than 2.6, no more than 2.55, no more than 2.5 or no more than 2.45.

[0165] • wherein the cellulose ester has a DSOH of at least 0.05, at least 0.1, at least 0.2, at least 0.3, at least 0.4 or at least 0.5 and / or no more than 1.5, no more than 1.4, no more than 1.3, no more than 1.2, no more than 1.1 or no more than 1.0.

[0166] • wherein the cellulose ester has an acetyl content of at least 30 wt%, at least 35 wt%, or at least 40 wt%, and / or no more than 65 wt%, no more than 60 wt%, no more than 55 wt%, no more than 50 wt%, or no more than 45 wt%.

[0167] ●Wherein the cellulose ester has a hydroxyl content of at least 0.3 wt%, at least 0.5 wt%, at least 1 wt%, at least 2 wt%, at least 3 wt% or at least 4 wt% and / or no more than 20 wt%, no more than 15 wt%, no more than 10 wt% or no more than 5 wt%.

[0168] ●Wherein, the cellulose ester has a hemicellulose content of no more than 10 wt%, no more than 9 wt%, no more than 8 wt%, no more than 7 wt%, no more than 6 wt%, no more than 5 wt%, no more than 4 wt%, no more than 3 wt%, no more than 2 wt% or no more than 1 wt%.

[0169] • wherein the cellulose ester has a number average absolute molecular weight of at least 5,000, at least 10,000, at least 15,000, at least 20,000 or at least 25,000 and / or no more than 75,000, no more than 70,000, no more than 65,000, no more than 60,000, no more than 55,000, no more than 50,000, no more than 45,000, no more than 40,000, no more than 35,000 or no more than 30,000.

[0170] • wherein the cellulose ester has a weight average absolute molecular weight of at least 50,000, at least 55,000, at least 60,000, at least 65,000, at least 70,000, at least 75,000, at least 80,000 or at least 85,000 and / or no more than 150,000, no more than 140,000, no more than 130,000, no more than 120,000, no more than 110,000, no more than 100,000 or no more than 95,000.

[0171] ● wherein the cellulose ester has a glass transition temperature of at least 120°C, at least 125°C, at least 130°C, at least 135°C, at least 140°C, at least 145°C, at least 150°C, at least 155°C, at least 160°C, at least 165°C, at least 170°C or at least 175°C and / or no more than 250°C, no more than 245°C, no more than 240°C, no more than 235°C, no more than 230°C, no more than 225°C, no more than 220°C, no more than 215°C, no more than 210°C, no more than 205°C, no more than 200°C, no more than 195°C, no more than 190°C or no more than 185°C.

[0172] • Wherein the cellulose ester comprises cellulose diacetate and / or cellulose triacetate.

[0173] - wherein the cellulose ester comprises a mixed cellulose ester.

[0174] • Wherein the cellulose ester comprises cellulose acetate propionate and / or cellulose acetate butyrate.

[0175] • wherein the cellulose ester has a DS of propionyl and / or butyral of at least 0.1, at least 0.2 or at least 0.3 and / or no more than 1.5, no more than 1.4, no more than 1.3, no more than 1.2, no more than 1.1, no more than 1.0, no more than 0.9, no more than 0.8, no more than 0.7, no more than 0.6, no more than 0.5 or no more than 0.4.

[0176] - wherein at least a portion of said recycled content of said cellulose ester is directly derived from one or more waste materials.

[0177] - wherein at least a portion of said recycled content of said cellulose ester is indirectly derived from one or more waste materials.

[0178] - wherein a portion of said recycled content of said cellulose ester is directly derived from one or more waste materials and a portion of said recycled content of said cellulose ester is indirectly derived from one or more waste materials.

[0179] An article comprising cellulose ester fibers formed according to any of the above features, the article being selected from the group consisting of tow bands, staple fibers, filaments, bundles, slivers, tubes, rovings, yarns, bales, fabrics, textiles, woven articles, nonwoven articles, knitted textiles, tobacco filters, and / or heat-not-burn tobacco products.

[0180] ● The product has one, two, three or four of the following properties in any combination

[0181] Claims supporting the disclosure - Second embodiment

[0182] In a second embodiment of the present technology, a method for preparing recycled content cellulose ester fiber is provided, the method comprising: (a) providing a first raw material having recycled content derived from textile waste; (b) providing a second raw material having recycled content derived from waste plastics; (c) synthesizing a recycled content cellulose ester material from at least the first raw material and the second raw material, wherein the recycled content cellulose ester material has recycled content derived from textile waste and waste plastics; and (d) spinning the recycled content cellulose ester material to produce recycled content cellulose ester fiber having recycled content derived from textile waste and waste plastics.

[0183] The second embodiment described in the preceding paragraphs may also include one or more of the additional aspects listed below. Each of the following additional aspects of the second embodiment may be an independent feature, or may be combined with one or more of the other additional aspects to the same degree.

[0184] - wherein the recycled content cellulose ester fibers have a total recycled content of at least 20%, at least 40%, at least 50%, or at least about 60%.

[0185] o wherein the recycled content cellulose ester fiber comprises at least 10%, at least 20%, at least 30% or at least about 40% recycled content derived from textile waste and at least 5%, at least 10%, at least 15% or at least about 20% recycled content derived from waste plastic.

[0186] ■ wherein the recycled content cellulose ester fibers comprise at least 10%, at least 20%, at least 30%, or about 40% renewable content.

[0187] - wherein said renewable content is derived from wood pulp used in said synthesis of step (c).

[0188] - Wherein the total recycled content of the recycled content cellulose ester fibers ranges from 10% to 100%, 20% to 90%, 30% to 90%, 50% to 70%, or is about 60%.

[0189] ○Wherein the recycled content cellulose ester fiber comprises 10% to 80%, 20% to 60%, 30% to 50% or about 40% recycled content derived from textile waste, and 5% to 40%, 10% to 30%, 15% to 25% or about 20% recycled content derived from waste plastics.

[0190] ■ wherein the recycled content cellulose ester fiber comprises in the range of 10% to 80%, 20% to 60%, 30% to 50%, or about 40% renewable content.

[0191] - wherein said renewable content is derived from wood pulp used in said synthesis of step (c).

[0192] ●Wherein the textile waste is pre-consumer textile waste.

[0193] o wherein the pre-consumer textile waste comprises at least 90%, 94%, 96% or 99% by weight alpha cellulose.

[0194] o wherein the pre-consumer textile waste is selected from the group consisting of cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, reject waste, yarn waste, production waste, cutter clippings, twisting waste or a mixture of two or more thereof.

[0195] ○The waste plastics are post-consumer waste plastics.

[0196] ● Also includes providing a third raw material having a renewable content, wherein the synthesizing of step (c) includes synthesizing the recycled content cellulosic material from at least the first raw material, the second raw material and the third raw material.

[0197] ○Wherein the third raw material is wood pulp.

[0198] ■Wherein the first raw material is pre-consumer textile waste.

[0199] • wherein the second raw material is at least one of acetic acid and acetic anhydride.

[0200] • wherein the first feedstock comprises at least 90%, 94%, 96% or 99% by weight alpha cellulose, wherein the second feedstock comprises at least one of acetic acid and acetic anhydride.

[0201] o Wherein the first raw material comprises cotton linters, undercombed cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, defective waste, yarn waste, production waste, cutter clippings, twisting waste or a mixture of two or more thereof.

[0202] ■ wherein the second raw material comprises acetic anhydride.

[0203] • Wherein the textile waste comprises cotton and the waste plastic comprises at least one of plastic packaging and carpet fibres.

[0204] ● wherein said providing of step (a) comprises obtaining cotton-containing waste from an industrial textile manufacturing process.

[0205] o wherein the cotton-containing waste comprises at least 90 wt%, at least 94 wt%, at least 96 wt% or at least 99 wt% alpha cellulose.

[0206] ●Wherein the providing of step (b) comprises converting the waste plastic into a recycled component synthesis gas comprising recycled component hydrogen and recycled component carbon monoxide.

[0207] ○ Wherein the providing of step (b) further comprises converting at least a portion of the recovered component synthesis gas into one or both of recovered component acetic anhydride and recovered component acetic anhydride.

[0208] ■Wherein the providing of step (b) comprises gasifying waste plastic to produce the recycled component synthesis gas.

[0209] ■Wherein the providing of step (b) comprises pyrolyzing waste plastic to produce a recycled content pyrolysis effluent, and then gasifying at least a portion of the recycled content pyrolysis effluent to produce the recycled content synthesis gas.

[0210] ■ wherein the converting comprises producing recovered component methanol from the recovered component synthesis gas and producing at least one of recovered component acetic acid and recovered component acetic anhydride from the recovered component methanol.

[0211] - wherein said synthesis of step (c) comprises acetylation of cellulose in acetic acid with acetic anhydride in the presence of sulphuric acid catalyst.

[0212] o wherein at least a portion of the cellulose is derived from the first feedstock and at least a portion of the acetic acid and / or acetic anhydride is derived from the second feedstock.

[0213] o wherein at least 5%, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90%, or 100% by weight of the cellulose is derived from the first feedstock, and wherein at least 5%, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90%, or 100% by weight of the acetic anhydride is derived from the second feedstock.

[0214] ■ wherein at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 40 wt%, at least 60 wt%, at least 80 wt%, at least 90 wt% or 100 wt% of the acetic acid is derived from the second feedstock.

[0215] o wherein the synthesis of step (c) further comprises hydrolyzing the acetylated intermediate cellulose ester product to produce the recycled component cellulose ester.

[0216] Claims supporting the disclosure - third embodiment

[0217] In a third embodiment of the present technology, a method for preparing recycled cellulose ester fiber is provided, the method comprising: (a) esterifying recycled cellulose with a recycled esterifying agent, thereby producing an initial cellulose ester material with recycled content from the recycled cellulose and the recycled esterifying agent; (b) optionally, hydrolyzing the initial cellulose ester material, thereby producing a hydrolyzed cellulose ester material; and (c) spinning at least one of the initial cellulose ester material and the hydrolyzed cellulose ester material, thereby producing recycled cellulose ester fiber with recycled content from the recycled cellulose and the recycled esterifying agent.

[0218] The third embodiment described in the preceding paragraphs may also include one or more of the additional aspects listed below. Each of the following additional aspects of the third embodiment may be an independent feature, or may be combined with one or more of the other additional aspects to the same degree.

[0219] • wherein the recycled content esterifying agent has recycled content derived from waste plastics.

[0220] • Wherein the recycled content cellulose comprises textile waste.

[0221] o wherein the textile waste is pre-consumer textile waste.

[0222] ■Wherein the pre-consumer textile waste is selected from cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, reject waste, yarn waste, production waste, cutter clippings, twisting waste or a mixture of two or more thereof.

[0223] ■ wherein the recycled content esterifying agent has recycled content derived from post-consumer waste plastics.

[0224] • wherein the recovered component esterification agent comprises one or both of acetic acid and acetic anhydride.

[0225] ●Wherein the recycled component esterifying agent comprises a recycled component acetylating agent.

[0226] o Wherein the recovered component acetylating agent comprises recovered component acetic anhydride.

[0227] - wherein said esterification of step (a) comprises esterifying non-recycled content cellulose with said recycled content esterifying agent, thereby producing said initial cellulose ester material.

[0228] o wherein the non-recycled component cellulose is renewable cellulose.

[0229] ■Wherein the renewable cellulose comprises wood pulp.

[0230] • wherein the esterification is carried out in the presence of acetic acid and acetic anhydride.

[0231] o wherein the acetic acid and the acetic anhydride each comprise recycled components derived from common waste materials.

[0232] ●The public waste materials are waste plastics.

[0233] • wherein the esterification is carried out in the presence of a sulfuric acid catalyst.

[0234] ●It also includes chemical recycling of waste plastics to produce esterification agents with recycled content.

[0235] Claims supporting the disclosure - fourth embodiment

[0236] In a fourth embodiment of the present technology, there is provided a recycled content cellulose ester fiber formed from a cellulose ester material having a repeating unit having the following structure:

[0237]

[0238] wherein the six-membered ring is a glucose ring, wherein R1, R2 and R3 are independently selected from hydrogen or a straight chain alkanoyl group having 2 to 10 carbon atoms, wherein the DS of the cellulose ester material is 乙酰基 In the range of 1.5 to 2.95, 2.0 to 2.65 or 2.25 to 2.55, wherein the DS of the cellulose ester material OH In the range of 0.5 to 1.5, 0.3 to 1.4 or 2.25 to 2.55, wherein at least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the alkanoyl groups are recycled alkanoyl groups derived from waste plastics, wherein at least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the glucose rings are recycled glucose rings derived from textile waste.

[0239] The fourth embodiment described in the preceding paragraph may also include one or more of the additional aspects listed below. Each of the following additional aspects of the second embodiment may be an independent feature, or may be combined with one or more of the other additional aspects to the same degree.

[0240] ●At least a portion of the glucose rings are non-recoverable component glucose rings.

[0241] o Wherein the ratio of non-recoverable component glucose rings to recovered component glucose rings is in the range of 0.1:1 to 10:1, 0.5:1 to 5:1, 1:1 to 4:1, 1.5:1 to 3:1, or about 2:1.

[0242] o Wherein the non-recycled component glucose rings are derived from renewable materials.

[0243] ■Wherein the renewable material is wood pulp.

[0244] - wherein the recycled content cellulose ester fibers have a total recycled content of at least 20%, at least 40%, at least 50%, or at least about 60%.

[0245] o wherein the recycled content cellulose ester fiber comprises at least 10%, at least 20%, at least 30% or at least about 40% recycled content derived from textile waste and at least 5%, at least 10%, at least 15% or at least about 20% recycled content derived from waste plastic.

[0246] ■ wherein the recycled content cellulose ester fibers comprise at least 10%, at least 20%, at least 30%, or about 40% renewable content.

[0247] - wherein said renewable content is derived from wood pulp used in said synthesis of step (c).

[0248] - Wherein the total recycled content of the recycled content cellulose ester fibers ranges from 10% to 100%, 20% to 90%, 30% to 90%, 50% to 70%, or is about 60%.

[0249] ○Wherein the recycled content cellulose ester fiber comprises 10% to 80%, 20% to 60%, 30% to 50% or about 40% recycled content derived from textile waste, and 5% to 40%, 10% to 30%, 15% to 25% or about 20% recycled content derived from waste plastics.

[0250] ■ Wherein the recycled content cellulose ester fiber contains 10% to 80%, 20% to 60%, 30% to 50%, or about 40% renewable content.

[0251] • Wherein the renewable component is derived from wood pulp.

[0252] ●Wherein the textile waste is pre-consumer textile waste.

[0253] o wherein the pre-consumer textile waste comprises at least 90 wt%, at least 94 wt%, at least 96 wt%, or at least 99 wt% alpha cellulose.

[0254] o wherein the pre-consumer textile waste is selected from the group consisting of cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-break suction device waste, reject waste, yarn waste, production waste, cutter clippings, twisting waste or a mixture of two or more thereof.

[0255] ○The waste plastics are post-consumer waste plastics.

[0256] • wherein the total degree of substitution (DS) of the recycled content cellulose ester fiber is in the range of 1.5 to 2.95, 2.0 to 2.65, or 2.25 to 2.55.

[0257] • wherein the recycled content cellulose ester fibers have a denier per filament (dpf) in the range of 0.5 to 30.

[0258] definition

[0259] It should be understood that the following is not intended to be an exhaustive list of defined terms. Other definitions may be provided in the foregoing description, such as, for example, where context accompanies the use of a defined term.

[0260] As used herein, the terms "a," "an," and "the" mean one or more.

[0261] As used herein, the term "and / or," when used in a list of two or more items, means that any one of the listed items may be used alone, or any combination of two or more of the listed items may be used. For example, if a composition is described as containing components A, B, and / or C, the composition may contain only A; only B; only C; a combination of A and B; a combination of A and C, a combination of B and C; or a combination of A, B, and C.

[0262] As used herein, the terms "comprising, comprises, comprise, contain, containing, and contains" are open transition words that are used to transition from the object recited before the term to one or more elements recited after the term, wherein the one or more elements listed after the transition word are not necessarily the only elements that make up the subject matter.

[0263] As used herein, the terms "having, has, and have" have the same open-ended meaning as "comprising, comprises, and comprise" provided above.

[0264] As used herein, the terms "including, include, and included" have the same open-ended meaning as "comprising, comprise, and comprise" provided above.

[0265] As used herein, the phrase "at least a portion" includes at least a portion and up to and including the entire amount or time period.

[0266] As used herein, the term "chemical route" refers to one or more chemical processing steps (eg, chemical reactions, physical separations, etc.) between an input material and a product material, wherein the input material is used to prepare the product material.

[0267] As used herein, the term "chemical recycling" refers to a waste plastic recycling process that includes the steps of chemically converting waste plastic polymers into lower molecular weight polymers, oligomers, monomers and / or non-polymeric molecules (e.g., hydrogen, carbon monoxide, methane, ethane, propane, ethylene and CO), which are themselves useful and / or can be used as a feedstock for another chemical production process.

[0268] As used herein, the term "co-located" refers to the property of at least two objects being located in a common physical location and / or within 5 miles, 1 mile, 0.5 miles, or 0.25 miles of each other.

[0269] As used herein, the terms "credit-based recycled content," "non-physical recycled content," and "indirect recycled content" all refer to materials that are not physically traceable back to scrap, but to which a recycled content credit has been attributed.

[0270] As used herein, the term "directly derived" means having at least one physical component derived from waste material.

[0271] As used herein, the term "indirectly derived" refers to a recycled content that is (i) attributable to waste material, but (ii) not based on the application of a physical component that is derived from waste material.

[0272] As used herein, the term "remotely located" means that the distance between two facilities, sites, or reactors is at least 0.1 miles, 0.5 miles, 1 mile, 5 miles, 10 miles, 50 miles, 100 miles, 500 miles, or 1000 miles.

[0273] As used herein, the term "mass balance" refers to a method of tracking recycled content based on the mass of recycled content in various materials.

[0274] As used herein, the terms "physical recycled content" and "direct recycled content" both refer to materials that are physically traceable back to waste.

[0275] As used herein, the term "pre-consumer textile waste" refers to waste generated by the commercial textile industry during the processing of cotton-based fibers, such as during garment, fabric and / or yarn manufacturing.

[0276] As used herein, the term "primarily" means greater than 50% by weight. For example, a stream, composition, feedstock, or product that is primarily propane is a stream, composition, feedstock, or product that contains greater than 50% by weight propane.

[0277] As used herein, the term "recycled content" refers to a composition that is or contains a composition that is directly and / or indirectly derived from recycled materials. Recycled content is generally used to refer to physical recycled content and credit-based recycled content. Recycled content is also used as an adjective to describe materials that have physical recycled content and / or credit-based recycled content.

[0278] As used herein, the term "recycled content credit" refers to a non-physical measure of physical recycled content that can be attributed directly or indirectly (i.e., via a digital inventory) from a first material having physical recycled content to a second material having less than 100% physical recycled content.

[0279] As used herein, the term "textile waste" refers to used, discarded and / or discarded cotton-based materials from any source associated with the manufacture, sale, use or disposal of textiles.

[0280] As used herein, the term "total recycled content" refers to the cumulative amount of physical recycled content and credit-based recycled content from all sources.

[0281] As used herein, the term "waste" refers to used, discarded and / or discarded materials.

[0282] As used herein, the terms "waste plastic" and "plastic waste" refer to used, discarded and / or discarded plastic materials.

[0283] Numerical range

[0284] This specification uses numerical ranges to quantify certain parameters related to the present invention. It should be understood that when numerical ranges are provided, these ranges should be interpreted as providing literal support for claim limitations that only recite the lower limit of the range and claim limitations that only recite the upper limit of the range. For example, the disclosed numerical range of 10 to 100 provides literal support for claims that recite "greater than 10" (no upper limit) and claims that recite "less than 100" (no lower limit).

[0285] In addition, it should be understood that the listing of numerical values ​​following descriptors such as "at least" and "not more than" provides literal support for ranges based on all numerical values ​​following the descriptor. For example, a statement specifying "at least 2, 5, or 10 and / or not more than 100, 50, or 25" would provide literal support for ranges of "at least 25," "not more than 50," and "at least 10 and not more than 25."

[0286] Example

[0287] The following examples illustrate the methods according to the present disclosure. However, it should be understood that these examples are provided by way of illustration, and nothing therein should be construed as limiting the overall scope.

[0288] Example 1

[0289] Thin film preparation and characterization

[0290] 1. Thin Slice Preparation

[0291] A wet pulp roll containing cotton linters as pre-consumer textile waste was shredded and the chips were soaked in glacial acetic acid. After soaking, the cellulose present in the chips was acetylated with acetic anhydride, followed by partial hydrolysis in the presence of sulfuric acid. Cellulose diacetate flakes were recovered from the solution, washed and dried. This process was repeated three times to produce four cellulose diacetate samples whose cellulose was completely derived from cotton linters.

[0292] 2. Acetyl content and intrinsic viscosity of flakes

[0293] The samples were analyzed for acetyl content and intrinsic viscosity ("IV") and compared to a control, which was cellulose diacetate prepared by the same process except that 100% wood pulp was used.

[0294] To determine the acetyl content, each flake sample was dissolved in acetone by stirring. After dissolution, the sample solution was injected into a liquid chromatography system where the polymers were separated based on the degree of substitution by reversed phase liquid chromatography. An evaporative light scattering detector was used for quantification. The calculation used was as follows:

[0295] Acetyl percentage

[0296] Wt%Acetyl=mxCT+b

[0297] in:

[0298] Wt%Acetyl = weight % of acetyl

[0299] m = calibration slope, in wt% acetylmin-1

[0300] CT = Peak centroid time of the polymer sample, in minutes

[0301] b = y-intercept of the calibration line, in wt% acetyl

[0302] Relative acetyl dispersion

[0303]

[0304] in:

[0305] RAS = relative acetyl dispersion

[0306] WDs = time width of the sample peak at one-tenth the height

[0307] WDc = time width of the reference sample peak at one-tenth the height

[0308] The intrinsic viscosity was determined by first drying the flakes by heating them in an MF-50 moisture analyzer at 130°C for about 5 minutes, followed by heating them in an oven at 105°C for 30 minutes. The dried flakes were dissolved in acetone at a concentration of 0.75 g / dL. The samples were injected separately into a relative viscometer, with one capillary measuring the pressure of HPLC grade acetone and the other capillary measuring the pressure of the cellulose acetate and acetone sample solutions. The ratio of these values ​​was used to determine the relative viscosity. The calculation is as follows:

[0309]

[0310] (relative to the viscosity of the solvent)

[0311] η sp =η 2rel -1

[0312] (Specific viscosity)

[0313]

[0314] (Solomon-Gatesman Equation for Intrinsic Viscosity)

[0315] In the above formula, "c" is the viscometer constant defined by the ratio of the two capillaries under baseline conditions, where the system has solvent flowing in the two capillaries at a steady pressure.

[0316] Table 1 illustrates these results.

[0317] Table 1.

[0318]

[0319] A Dry in a rotary cone vacuum dryer at 82 °C until moisture is less than 2%.

[0320] A blend of 67 wt% Sample #1 flakes (100% wood pulp) and 33 wt% Sample #8 flakes (100% cotton linters) was prepared and analyzed for acetyl content and intrinsic viscosity. These results are in Table 2.

[0321] Table 2.

[0322]

[0323] The foregoing demonstrates that the use of flakes made from recycled cellulosic material in combination with those made from conventional wood pulp results in substantially similar flake properties when compared to flakes made entirely from wood pulp and / or flakes made entirely from cotton linter pulp.

[0324] 3. Polymer evaluation

[0325] The corresponding molecular weight and polydispersity index ("PDI") of the cellulose diacetate of samples 2-5 and 8 were determined. The molecular weight was determined by GPC according to ASTM D 6474. The molecular weight measurements were used to calculate the PDI, which is defined as Mw / Mn.

[0326] Table 3 presents these results.

[0327] Table 3.

[0328] Sample #2 Sample #3 Sample #4 Sample #5 Sample #8 Mn 50989 45535 48923 44644 43637 M 134078 114945 118888 116502 107451 Mz 259703 216704 225080 223292 202944 PDI 2.63 2.52 2.43 2.61 2.46

[0329] Example 2

[0330] Yarn preparation and characterization

[0331] 1. Yarn Preparation

[0332] Sheet samples 1 (100% wood pulp), 8 (100% cotton linters), and 9 (blend) from Example 1 were each dry spun into yarn according to the procedure described above.

[0333] 2. Polymer Evaluation

[0334] The corresponding molecular weight and PDI of the cellulose diacetate for the yarns formed from Samples 1, 8 and 9 were determined as described in Example 1. Table 4 gives these results.

[0335] Table 4.

[0336]

[0337] 3.Wood chip whiteness

[0338] The yarns of samples 1, 8 and 9 were analyzed for chip whiteness. Pressed chips were prepared from washed, dried, ground and pressed acetate. The sample chips were provided and measured using a spectrophotometer in the wavelength range of 380nm-700nm. Whiteness results were generated using a whiteness index based on the CIE Ganz 82 formula.

[0339] These results are shown in Table 5.

[0340] Table 5.

[0341] sample Wood chip whiteness Sample #1 Yarn 79.3 Sample #8 Yarn 82.9 Sample #9 Yarn 83.3

[0342] The wood chip brightness should be 73 or higher, indicating that using recycled content as a cellulose source will not negatively impact the yarn.

[0343] 4. Tensile strength

[0344] The yarns of Samples 1, 8, and 9 were analyzed for tensile strength and elongation as described in ASTM D22556. These results are shown in Table 6.

[0345] Table 6.

[0346]

[0347]

[0348] Example 3

[0349] Fabric preparation and dye uptake analysis

[0350] 1. Fabric Preparation

[0351] Yarns from Samples 1 (100% wood pulp), 8 (100% cotton linters), and 9 (blend) as described in Example 2 were separately knitted into 100-GSM (±10) single jersey fabrics using a 9" diameter 28gg Vanguard knitting machine. The knitted fabrics were heat set in preparation for wet processing. Each pair of samples being compared moved together through the wet processing sequence in the same dyeing container. Therefore, the two samples being compared experienced the same knitting, heat setting, and wet processing conditions. In order to determine if there were any wet processing differences when the depth of shade was varied, four colors were dyed: ivory, harvest gold, gray, and black. The dyed fabrics were dried and conditioned for dye uptake analysis.

[0352] 2. Fabric color comparison

[0353] Pairs of samples from each dyeing container were measured against each other, with the control sample as the standard and the experimental sample as the batch. Both the control sample and the experimental sample were folded into eight layers so that no light was transmitted through the fabric. The color coordinates ΔL, Δa, Δb, and ΔE CMC were recorded for each measurement. ΔL is a measure of the brightness difference, Δa is a measure of the red / green difference, and Δb is a measure of the yellow / blue difference. ΔE CMC is the total color difference between the two samples measured. The fabric was folded in a different way and the process was repeated, still producing eight layers to account for any differences due to different fabric orientations.

[0354] This procedure was used to compare the hue effects of using different pulp sources. The three different comparisons were: 100% wood based (0% cotton linter) pulp versus 100% cotton linter pulp; 100% wood based pulp versus 33% cotton linter blended pulp; and 33% cotton linter blended pulp versus 100% cotton linter pulp. The procedure was modified for this study in that the control and experimental samples were dyed using two wet treatment methods. The two different conditions were the control sample and two experimental samples contained in the same dyeing container, or the control sample and only one experimental sample contained in the same dyeing container. The hue data are recorded in Tables 7-9, with the different methods indicated as "two-way comparison" or "three-way comparison." In most cases, the two-way comparison produced better results than the three-way comparison.

[0355] These results are shown in Tables 7-9. In each of these tables, if a standard and batch are designated as "statistically equivalent", this means:

[0356] The ivory data point is below a ΔE CMC of 0.65;

[0357] The harvest gold data point is below a ΔE CMC of 1.25;

[0358] Black data points are below a ΔE CMC of 0.45;

[0359] Gray data points are all below a ΔE CMC of 0.90; and

[0360] The average ΔE CMC of all grey data points is close to 0.31.

[0361] Based on the data from Tables 7-9, pulp source has a statistically significant effect on dye uptake, especially as the cotton linter pulp content increases.

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] The claims are not limited to the disclosed embodiments

[0368] The preferred forms of the present invention described above are intended to be used as illustrations only and should not be used in a limiting sense to interpret the scope of the present invention. Those skilled in the art may easily make modifications to the above exemplary embodiments without departing from the spirit of the present invention.

[0369] The inventors hereby declare that they intend to determine and assess the reasonably fair scope of the present invention under the doctrine of equivalents as it relates to any device that does not materially depart from the literal scope of the present invention as set forth in the following claims.

Claims

1. A method comprising reacting an esterifying agent with cellulose to form a cellulose ester, wherein at least a portion of the cellulose is derived from a first waste material and at least a portion of the esterifying agent is derived from a second waste material, wherein the cellulose ester has recycled content from the cellulose and the esterifying agent.

2. The method according to claim 1, wherein the first waste material is textile waste and the second waste material is plastic waste.

3. The method of claim 1, wherein the total recycled content of the cellulose ester is at least 20%, at least 40%, at least 50%, or at least about 60%.

4. A method for preparing recycled content cellulose ester fiber, the method comprising: (a) providing a first raw material having recycled content derived from textile waste; (b) providing a second feedstock having a recycled content derived from waste plastic; (c) synthesizing a recycled content cellulose ester material from at least the first raw material and the second raw material, wherein the recycled content cellulose ester material has recycled content derived from textile waste and waste plastic; as well as (d) spinning the recycle content cellulose ester material to produce recycle content cellulose ester fibers having recycle content derived from textile waste and waste plastic.

5. The method of claim 4, wherein the recycled content cellulose ester fibers have a total recycled content of at least 20%, at least 40%, at least 50%, or at least about 60%.

6. The method of claim 4, wherein the recycled content cellulose ester fiber comprises at least 10%, at least 20%, at least 30%, or at least about 40% recycled content derived from textile waste and at least 5%, at least 10%, at least 15%, or at least about 20% recycled content derived from waste plastic.

7. A method for preparing recycled content cellulose ester fiber, the method comprising: (a) esterifying recycled content cellulose with a recycled content esterifying agent, thereby producing a recycled content initial cellulose ester material from the recycled content cellulose and the recycled content esterifying agent; (b) optionally, hydrolyzing the initial cellulose ester material to produce a hydrolyzed cellulose ester material; as well as (c) spinning at least one of the initial cellulose ester material and the hydrolyzed cellulose ester material to produce recycled content cellulose ester fibers having recycled content from the recycled content cellulose and the recycled content esterifying agent.

8. A recycled content cellulose ester fiber formed from a cellulose ester material having repeating units of the following structure: The six-membered ring is a glucose ring. Where R 1 , R 2 and R 3 independently selected from hydrogen or a straight chain alkanoyl group having 2 to 10 carbon atoms, wherein the DS of the cellulose ester material 乙酰基 In the range of 1.5 to 2.95, 2.0 to 2.65 or 2.25 to 2.55, wherein the DS of the cellulose ester material OH In the range of 0.5 to 1.5, 0.3 to 1.4 or 2.25 to 2.55, wherein at least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the alkanoyl groups are recycled content alkanoyl groups derived from waste plastics, At least a portion, at least 10%, at least 20%, at least 40%, at least 60%, at least 80%, at least 90% or 100% of the glucose rings are recycled content glucose rings derived from textile waste.

9. The recycled cellulose ester fiber according to claim 8, wherein at least a portion of the glucose rings are non-recycled glucose rings.

10. The recycled cellulose ester fiber of claim 8, wherein the ratio of non-recycled glucose rings to recycled glucose rings is in the range of 0.1:1 to 10:1, 0.5:1 to 5:1, 1:1 to 4:1, 1.5:1 to 3:1, or about 2:

1.

11. The recycled content cellulose ester fiber of claim 8, wherein the non-recycled content glucose rings are derived from renewable materials.

12. The recycled content cellulose ester fiber of claim 11, wherein the renewable material is wood pulp.

13. The recycled content cellulose ester fiber of claim 8, wherein the recycled content cellulose ester fiber has a total recycled content of at least 20%, at least 40%, at least 50%, or at least about 60%.

14. The recycled content cellulose ester fiber of claim 13, wherein the recycled content cellulose ester fiber comprises at least 10%, at least 20%, at least 30%, or at least about 40% recycled content derived from textile waste and at least 5%, at least 10%, at least 15%, or at least about 20% recycled content derived from waste plastic.

15. The recycled content cellulose ester fiber of claim 8, wherein the textile waste is pre-consumer textile waste.

16. The recycled content cellulose ester fiber of claim 15, wherein the pre-consumer textile waste is selected from the group consisting of cotton linters, undercarded cotton, fabric clippings, cattle feed waste, comber rags, end-down suction device waste, reject waste, yarn waste, production waste, cutter clippings, twist waste, or a mixture of two or more thereof.

17. The recycled content cellulose ester fiber of claim 8, wherein the waste plastic is post-consumer waste plastic.

18. The recycled content cellulose ester fiber of claim 8, wherein the recycled content cellulose ester fiber has a total degree of substitution (DS) in the range of 1.5 to 2.95, 2.0 to 2.65, or 2.25 to 2.

55.

19. The recycled content cellulose ester fiber of claim 8, wherein the recycled content cellulose ester fiber has a denier per filament (dpf) in the range of 0.5 to 30.

20. An article comprising cellulose ester fibers formed according to any one of claims 8 to 19.

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