WO2022092195A1 - Procédé de collecte de fibre de polyamide, procédé de fabrication de produit de polyamide recyclé, et solution de dissolution de silicone - Google Patents

Procédé de collecte de fibre de polyamide, procédé de fabrication de produit de polyamide recyclé, et solution de dissolution de silicone Download PDF

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Publication number
WO2022092195A1
WO2022092195A1 PCT/JP2021/039806 JP2021039806W WO2022092195A1 WO 2022092195 A1 WO2022092195 A1 WO 2022092195A1 JP 2021039806 W JP2021039806 W JP 2021039806W WO 2022092195 A1 WO2022092195 A1 WO 2022092195A1
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WIPO (PCT)
Prior art keywords
silicone
polyamide fiber
polyamide
solution
product
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PCT/JP2021/039806
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English (en)
Japanese (ja)
Inventor
章黄 鈴岡
剛博 櫻田
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豊田通商株式会社
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Publication of WO2022092195A1 publication Critical patent/WO2022092195A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
    • C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to a method for recovering polyamide fibers, a method for producing recycled polyamide products, and a silicone solution.
  • Polyamide products such as nylon 6 and 6 are used for various purposes.
  • Polyamide is a synthetic resin. From the viewpoint of environmental load, it is desired to recycle polyamide.
  • polyamide fiber product composed of a cloth coated with silicone.
  • polyamide fiber products include airbag base fabrics. Silicone may be applied to the base fabric of the airbag to prevent air leakage.
  • Patent Document 1 Japanese Unexamined Patent Publication No. 2017-124553 describes a method for recycling a silicone-coated nylon airbag scrap cloth, wherein the silicone-coated layer of the scrap cloth is classified as a third grade.
  • a method for recycling a nylon airbag scrap cloth is disclosed, which comprises a step of immersing in an alkaline aqueous solution containing an amine and a surfactant.
  • Patent Document 2 Patent No. 6006030
  • a release agent containing an acid having a resolution with respect to silicone and / or a solvent selected from a predetermined group capable of dissolving silicone is used. It is described that the silicone-based surface treatment agent is removed by a predetermined method.
  • Patent Document 3 Japanese Unexamined Patent Publication No. 2009-269475
  • an airbag base cloth made of a polyamide fiber coated with silicone is immersed in an alkali-isopropyl alcohol solution to coat the airbag base cloth with silicone.
  • a method for removing silicone from an airbag base cloth is described, which comprises removing the fiber from the airbag base cloth.
  • an object of the present invention is to provide a technique capable of removing silicone from a polyamide fiber product in a short time.
  • the present invention includes the following matters.
  • a method for recovering polyamide fibers from a cloth-like polyamide fiber product coated with silicone which is an optional step of pretreating the polyamide fiber product for a dissolution treatment.
  • a method for recovering a polyamide fiber which comprises a step of treating the polyamide fiber product with a solution, wherein the solution contains an anionic surfactant and a chain saturated hydrocarbon.
  • a technique capable of removing silicone from a polyamide fiber product in a short time is provided.
  • the present embodiment relates to a method of removing silicone from a cloth-like polyamide fiber product coated with silicone, recovering the polyamide fiber, and manufacturing the polyamide product again from the recovered polyamide fiber. That is, the present embodiment relates to a method for recycling polyamide.
  • step S1 in removing the silicone, first, as an arbitrary step, a pretreatment for the cloth-like polyamide fiber product is performed (step S1). Subsequently, the polyamide fiber product is treated with the solution (step S2). At this time, as the dissolution liquid, a liquid containing an anionic surfactant and a chain saturated hydrocarbon is used. By using such a solution, silicone can be removed in a short time. After that, the polyamide fiber is recovered and a recycled polyamide product is manufactured (step S3).
  • Step S1 Pretreatment First, a cloth-like polyamide fiber product coated with silicone to be recycled is prepared, and if necessary, a pretreatment for dissolution treatment is performed.
  • a fiber opening treatment is performed as a pretreatment.
  • the silicone can be removed in a shorter time during the treatment with the solution in the next step S2.
  • a commercially available fiber opening machine for example, an anti-hair opening machine may be used.
  • the cloth made of polyamide fiber is simply cut.
  • the polyamide fiber product is cut so as to have an irregular shape such that the size of one side is in the range of 0.1 to 50 cm.
  • it is cut so that the area is 0.01 to 2500 cm 2 , preferably 1 to 100 cm 2 .
  • the shape after cutting is preferably a shape close to a square. In this case, as will be described in detail later, it is preferable to perform the fiber opening treatment in the next step S2.
  • the polyamide fiber product to be recycled may be any one coated with silicone, and is not particularly limited, and examples thereof include cloth made of aliphatic polyamide fiber, preferably nylon 6,6. Examples include made cloth. Specific examples thereof include a base cloth for airbags. When manufacturing the airbag base fabric, scraps are generated. It would be preferable if such scraps could be recycled.
  • silicone may be applied to the base fabric of the airbag for the purpose of preventing air leakage. Since the method according to the present embodiment can remove silicone in a short time, it is suitably applied to the recycling of the base cloth of the airbag coated with silicone.
  • the silicone removed in the present embodiment is not particularly limited, but is preferably a polymer compound having a siloxane bond (-Si-O-Si-) as a main skeleton, that is, silicone rubber. More preferably, it is a silicone rubber having a number of siloxane bonds (number of Si—O bonds) of 5,000 to 10,000. Specific examples of the silicone rubber include methyl silicone rubber, vinyl / methyl silicone rubber, and phenyl / methyl silicone rubber.
  • Step S2 Treatment with lysate Subsequently, the polyamide fiber product is treated with lysate. Specifically, the polyamide fiber product is put into the dissolution liquid, and the dissolution liquid is stirred. As a result, silicone is removed from the polyamide fiber product, and a washed polyamide fiber is obtained.
  • the fiber opening process is not performed as the pretreatment in step S1, for example, if only cutting is performed as the pretreatment, the fiber opening process can be performed in this step.
  • the fiber opening treatment is performed in the solution by stirring at a high speed to the extent that the polyamide fiber product is opened. be able to.
  • the silicone can be removed in a shorter time.
  • the solution contains an anionic surfactant and a chain saturated hydrocarbon.
  • the anionic surfactant is not particularly limited, and examples thereof include a sulfonic acid type surfactant, preferably an alkylbenzene sulfonic acid, and more preferably a dodecylbenzene sulfonic acid.
  • the content of the anionic surfactant in the solution can be set so as to dissolve the silicone and not to dissolve the polyamide to be recovered.
  • the content of the anionic surfactant in the solution is, for example, 0.1 to 75% by mass, preferably 1 to 50% by mass, and more preferably 1 to 15% by mass.
  • the silicone to be removed is methyl silicone rubber or vinyl / methyl silicone rubber
  • the content of the anionic surfactant may be 1% by mass or more.
  • the silicone contains phenyl / methyl silicone rubber
  • the content of the anionic surfactant is preferably 6% by mass or more.
  • Chain saturated hydrocarbons are used as a solvent for the solution.
  • the chain saturated hydrocarbon has a function of dissolving silicone.
  • the polyamide fiber to be recovered is difficult to dissolve in chain saturated hydrocarbons. Therefore, by using a chain saturated hydrocarbon as a solvent, it becomes possible to selectively dissolve silicone.
  • the structure of the chain saturated hydrocarbon is not particularly limited, and may be a linear structure or a branched chain structure.
  • As the chain saturated hydrocarbon those having 6 to 16 carbon atoms, more preferably 8 to 14 carbon atoms are preferably used.
  • one having a high flash point specifically, a flash point at 1 atm of 70 ° C. or higher
  • Chain saturated hydrocarbons with a high flash point are preferable because they are easy to handle from the viewpoint of fire fighting.
  • preferable chain saturated hydrocarbons include octane, nonane, decane, undecane, dodecane, tridecane, and isoparaffin solvents, and dodecane is most preferable in consideration of safety and the like.
  • the solution may contain additives other than anionic surfactants and chain saturated hydrocarbons for various purposes.
  • anionic surfactants and chain saturated hydrocarbons occupy most of the solution.
  • the total content of the anionic surfactant and the chain saturated hydrocarbon in the solution is preferably more than 80% by mass, and more preferably the total content is 85% by mass or more. It is more preferable that the total content is 90% by mass or more.
  • the temperature of the solution is, for example, 0 to 50 ° C, preferably 5 to 40 ° C. Within such a range, silicone can be removed in a short time. On the other hand, the polyamide fiber to be recovered is difficult to dissolve. Therefore, it becomes easy to selectively remove the silicone.
  • the treatment time of the polyamide fiber product with the solution is, for example, 0.1 to 100 minutes, preferably 0.5 to 60 minutes. With such a treatment time, the silicone is sufficiently removed and the polyamide fiber to be recovered is difficult to dissolve. Therefore, it becomes easy to selectively remove the silicone.
  • the distillation is carried out by vacuum distillation. If vacuum distillation is performed, distillation can be performed at a low temperature. Therefore, it becomes easy to perform distillation at a temperature or lower at which the components constituting the solution are decomposed. Distillation may be simple distillation or multi-stage distillation.
  • dodecylbenzenesulfonic acid As the anionic surfactant and dodecane as the chain saturated hydrocarbon. Since dodecane and dodecylbenzene sulfonic acid have similar boiling points, it is easy to recover both components by distillation. Further, in this case, if vacuum distillation is performed, the boiling point of dodecylbenzene sulfonic acid is lowered, and it becomes easier to perform distillation at a temperature lower than the decomposition temperature of dodecylbenzene sulfonic acid.
  • Step S3 Production of a recycled polyamide product from the washed polyamide fiber Subsequently, a recycled polyamide product is manufactured from the washed polyamide fiber obtained in step S2.
  • This step is not particularly limited, but is, for example, a step of separating the washed polyamide fiber from the solution (step S3-1), a step of decolorizing the washed polyamide fiber (step S3-2), and decolorization.
  • This can be realized by a method including a step of pelletizing the processed object (step S3-3) and a step of obtaining a polyamide product using the pellets (step S3-4). Each process will be described below.
  • Step S3-1 Separation
  • the washed polyamide fiber obtained in step S2 is in a state where the cotton-like polyamide fiber is impregnated with the solution. Therefore, the polyamide fiber and the solution are separated by using a centrifuge.
  • the rotation speed of the centrifuge is, for example, 3000 to 8000 rpm. As a result, the polyamide fiber can be separated from the solution and recovered.
  • Step S3-2 Decolorization Subsequently, if necessary, decolorization processing is performed.
  • the polyamide fiber can be decolorized by treating with dimethylformamide at 120 to 160 ° C. for 10 to 60 minutes.
  • the solvent used for decolorization is separated from the polyamide fiber by performing a treatment at 300 to 8000 rpm using a centrifuge.
  • the decolorizing solvent such as dimethylformamide used for decolorization can be reused, for example, by distilling at a vacuum degree of 1 to 100 Torr when the decolorizing performance is deteriorated.
  • Step S3-3 Pelleting Subsequently, the polyamide fiber is pelletized.
  • the pelletization may be carried out by using a known means.
  • Step S3-4 Production of Recycled Polyamide Product Subsequently, a recycled polyamide product is produced from the pellets obtained in step S2-3.
  • pellets can be used as a raw material for spinning to produce polyamide filaments, which can be used to manufacture clothing.
  • the solution having a specific composition by using the solution having a specific composition, it is possible to remove the silicone from the cloth made of polyamide fiber in a short time and recycle the polyamide.
  • the prepared airbag base cloth was cut into a rectangular shape with a side of 1 to 1.5 cm, and a cut cloth was prepared and used as a test sample.
  • the airbag base cloth was opened using a dry fiber opening facility (anti-hair machine), and a cotton-like test sample was also obtained.
  • the prepared cut cloth test sample and cotton-like test sample were put into a sample bottle containing a solution, and stirred with a stirrer.
  • a solution consisting of about 0.7 g of NaOH, 7 g of water, and 12.5 g of isoapropyl alcohol was used.
  • the test was performed at different temperatures and times, and it was observed whether or not the silicone was removed after the test. Since the silicone is colored, it was visually confirmed whether or not the silicone was removed.
  • Example 2 Examination of other solvents The composition of the solution was changed in various ways, and whether or not silicone could be removed was examined in the same manner as in Experimental Example 1.
  • the composition, test conditions, and results of the investigated solution are shown in Tables 2-1 to 2-3.
  • Tables 2-1 to 2-3 "IP-1016” is a trade name of a chain saturated hydrocarbon solvent manufactured by Idemitsu Kosan Co., Ltd., and is an isoparaffin-based solvent.
  • DBSA refers to n-dodecylbenzene sulfonic acid.
  • DBSA-Na refers to sodium dodecylbenzene sulfonate.
  • Example 3 Examination of Anionic Surfactant Subsequently, a combination of dodecylbenzene sulfonic acid (anionic surfactant) and an organic solvent was used as a solution, and the same examination as in Experimental Example 1 was carried out. Table 3 shows the organic solvent used, test conditions and results. As shown in Table 3 (Example 3-9), silicone can be removed in a short time only when a combination of dodecylbenzene sulfonic acid and IP-1016, which is a chain saturated hydrocarbon, is used. did it.
  • Example 4 Examination of Dissolution Treatment Conditions Concentration of dodecylbenzenesulfonic acid for the combination of dodecylbenzenesulfonic acid confirmed to be effective in Experimental Example 3 and chain saturated hydrocarbon (IP-1016) Was changed, and the removability of silicone was examined in the same manner as in Example 1.
  • Table 4 shows the composition of the dissolution liquid, the dissolution treatment conditions, and the results. As shown in Table 4, when the amount of dodecylbenzenesulfonic acid was 1% by mass, the silicone could not be removed at room temperature for a short time.
  • silicone could be removed by treatment at room temperature for 60 minutes.
  • Example 6 Examination of Silicone As a base cloth for an airbag coated with silicone, a product A different from that used in Experimental Examples 1 to 6 was prepared. Analysis of the silicone applied to product A revealed that it was vinyl methyl silicone rubber. Using the prepared product A, various conditions were changed, and the removability of silicone was examined in the same manner as in Experimental Example 1. The results are shown in Table 6. As shown in Table 6, in the case of the fiber opening treatment, that is, in the case of "cotton", if the dodecylbenzene sulfonic acid concentration was 1% or more, the silicone could be removed in a short time.
  • Example 7 Test on actual machine Based on the above examination results, the combination of chain saturated hydrocarbon and dodecylbenzene sulfonic acid was examined using an actual machine. Specifically, a melting tank equipped with a stirring device capable of opening the airbag base cloth in a wet manner was prepared. More specifically, it has a stirring blade connected to a rotating shaft, and when the solution to which the cut cloth is put is stirred, the cut cloth collides with the stirring blade and a shearing force is applied to the cut cloth. A stirrer configured as described above was used.
  • a dissolution liquid a liquid consisting of dodecane and dodecylbenzenesulfonic acid (10% by weight) (there are no other components) was prepared.
  • the cut cloth was put into the solution, the stirrer was rotated at high speed (about 9000 to 16000 rpm), and the time until the silicone was removed was observed.
  • Example 8 Examination of the type of silicone using an actual machine As a test sample, the same airbag base cloth as in Experimental Example 1 (confirmed that vinyl / methylsilicone rubber or methylsilicone rubber is applied) , Product B (confirmed that phenyl / methyl silicone rubber was applied) was prepared. The prepared airbag base cloth was cut into a square of 1 cm ⁇ 1 cm and used as a test sample. Next, as in Experimental Example 7, it was confirmed whether or not the silicone was removed by using an actual machine. As the solution, a mixture of dodecane and dodecylbenzene sulfonic acid was used.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Artificial Filaments (AREA)
  • Chemical Treatment Of Fibers During Manufacturing Processes (AREA)

Abstract

Ce procédé de collecte d'une fibre de polyamide comprend une étape de traitement d'un produit de fibre de polyamide de type tissu, qui est revêtu de silicone, avec une solution de dissolution, la solution de dissolution contenant un tensioactif anionique et un hydrocarbure saturé de type chaîne.
PCT/JP2021/039806 2020-10-30 2021-10-28 Procédé de collecte de fibre de polyamide, procédé de fabrication de produit de polyamide recyclé, et solution de dissolution de silicone WO2022092195A1 (fr)

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JP2020-182999 2020-10-30
JP2020182999A JP7024037B1 (ja) 2020-10-30 2020-10-30 ポリアミド繊維の回収方法、リサイクルポリアミド製品の製造方法、及びシリコーンの溶解液

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KR102611580B1 (ko) * 2022-10-13 2023-12-07 한국화학연구원 폐 에어백 재활용 방법

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