JP2009174109A - Flame retarding processing agent for polyester fiber and method of producing flame-retardant polyester fiber - Google Patents
Flame retarding processing agent for polyester fiber and method of producing flame-retardant polyester fiber Download PDFInfo
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Abstract
Description
本発明は、ポリエステル繊維用難燃加工剤及び難燃性ポリエステル繊維の製造方法に関する。 The present invention relates to a flame retardant processing agent for polyester fibers and a method for producing flame retardant polyester fibers.
ポリエステル繊維材料の後加工難燃化においては、その用途から、水洗い、ドライクリーニング等に対する耐久性も要求される。このような難燃化及び洗濯耐久性の条件を満たし得る難燃加工剤としてヘキサブロモシクロドデカン（HBCD）がある（例えば特許文献１、特許文献２）。 In post-processing flame-retarding of polyester fiber materials, durability against water washing, dry cleaning, and the like is also required due to its use. There is hexabromocyclododecane (HBCD) as a flame retardant processing agent that can satisfy such conditions of flame retardancy and washing durability (for example, Patent Document 1 and Patent Document 2).
我が国では、ヘキサブロモシクロドデカンが難分解性、高蓄積性であることから、平成１６年９月に化審法の第一種監視化学物質として登録されている。このような背景から、業界ではヘキサブロモシクロドデカンの使用を極力抑え、自然環境中への排出量の低減が要請されている。
しかしながら、ポリエステル繊維の後加工難燃化において、ヘキサブロモシクロドデカンと同等の優れた難燃性を付与できる化合物は未だ知られていないのが現状である。 However, at present, no compound has yet been known that can impart excellent flame retardancy equivalent to that of hexabromocyclododecane in post-processing flame retardant of polyester fibers.
従って、本発明は、ヘキサブロモシクロドデカンのように高い難燃性を付与することができると同時に、ヘキサブロモシクロドデカンの問題点（難分解性、高蓄積性等）を低減ないしは回避できるポリエステル繊維用難燃加工剤を提供することを主な目的とする。 Therefore, the present invention can provide high flame retardancy like hexabromocyclododecane and at the same time reduce or avoid problems of hexabromocyclododecane (hard decomposition, high accumulation, etc.). The main purpose is to provide a flame retardant finishing agent.
本発明者は、従来技術の問題点に鑑みて鋭意研究を重ねた結果、特定の化合物がポリエステル繊維用の後加工難燃化に有効であることを見出し、本発明を完成するに至った。 As a result of intensive studies in view of the problems of the prior art, the present inventors have found that a specific compound is effective for post-processing flame retarding for polyester fibers, and have completed the present invention.
すなわち、本発明は、下記のポリエステル繊維用難燃加工剤及び難燃性ポリエステル繊維の製造方法に係る。
１．下記式（Ｉ）
２． 前記トリス（２，３−ジブロモプロピル）イソシアヌレートが分散媒中に分散されている、前記項１に記載のポリエステル繊維用難燃加工剤。
３． さらに界面活性剤を含む、前記項１又は２に記載のポリエステル繊維用難燃加工剤。
４． 分散媒中に分散されている前記トリス（２，３−ジブロモプロピル）イソシアヌレートの分散粒子の平均粒子径が２μｍ以下である、前記項２又は３に記載のポリエステル繊維用難燃加工剤。
５． 難燃剤としてリン酸エステル系化合物及びヘキサブロモシクロドデカンの少なくとも１種をさらに含有する、前記項１〜４のいずれかに記載のポリエステル繊維用難燃加工剤。
６． ポリエステル繊維に前記ポリエステル繊維用難燃加工剤を接触させることにより難燃化処理を行う、前記項１〜５のいずれかに記載のポリエステル繊維用難燃加工剤。
７． 前記項１〜６のいずれかに記載のポリエステル繊維用難燃加工剤をポリエステル繊維に接触させることにより難燃化処理を行う工程を含むことを特徴とする難燃性ポリエステル繊維の製造方法。
８． 前記工程が、（１）ポリエステル繊維用難燃加工剤をポリエステル繊維と接触させた後、前記ポリエステル繊維を乾燥させ、次いで前記ポリエステル繊維を１５０℃〜２００℃で熱処理することにより前記ポリエステル繊維の難燃化処理を行う工程及び／又は（２）１００〜１５０℃に加温したポリエステル繊維用難燃加工剤とポリエステル繊維とを接触させることにより前記ポリエステル繊維の難燃化処理を行う工程である、前記項７に記載の製造方法。
９． 前記項７又は８に記載の製造方法によって得られる難燃性ポリエステル繊維。
１０．ポリエステル繊維の少なくとも繊維内部にトリス（２，３−ジブロモプロピル）イソシアヌレートを吸尽させるために用いる、前記項１〜６のいずれかに記載の繊維用難燃加工剤。
１１．トリス（２，３−ジブロモプロピル）イソシアヌレート及び前記難燃剤の合計１００重量部に対して０〜３０重量部の合成樹脂を含む、前記項１〜６のいずれかに記載の繊維用難燃加工剤。
１２．難燃化処理によってポリエステル繊維の少なくとも繊維内部にトリス（２，３−ジブロモプロピル）イソシアヌレートを吸尽させる、前記項７又は８に記載の製造方法。
That is, this invention relates to the manufacturing method of the following flame-retardant processing agent for polyester fibers, and a flame-retardant polyester fiber.
1. Formula (I)
2. Item 2. The flame retardant processing agent for polyester fibers according to Item 1, wherein the tris (2,3-dibromopropyl) isocyanurate is dispersed in a dispersion medium.
3. Item 3. The flame retardant agent for polyester fibers according to Item 1 or 2, further comprising a surfactant.
4). Item 4. The flame retardant processing agent for polyester fibers according to Item 2 or 3, wherein the dispersed particles of the tris (2,3-dibromopropyl) isocyanurate dispersed in a dispersion medium have an average particle diameter of 2 μm or less.
5. Item 5. The flame retardant processing agent for polyester fiber according to any one of Items 1 to 4, further comprising at least one of a phosphate ester compound and hexabromocyclododecane as a flame retardant.
6). Item 6. The flame retardant for polyester fiber according to any one of Items 1 to 5, wherein the flame retardant treatment is performed by bringing the flame retardant for polyester fiber into contact with polyester fiber.
7). A method for producing a flame-retardant polyester fiber, comprising a step of performing a flame-retarding treatment by bringing the flame-retardant processing agent for polyester fiber according to any one of Items 1 to 6 into contact with the polyester fiber.
8). The step comprises (1) contacting the polyester fiber flame retardant with the polyester fiber, drying the polyester fiber, and then heat-treating the polyester fiber at 150 ° C. to 200 ° C. A step of performing a flame retardant treatment and / or (2) a step of performing a flame retardant treatment of the polyester fiber by bringing the polyester fiber into contact with a flame retardant agent for polyester fiber heated to 100 to 150 ° C. Item 8. The manufacturing method according to Item 7.
9. The flame-retardant polyester fiber obtained by the manufacturing method of said claim | item 7 or 8.
10. Item 7. The flame retardant processing agent for fibers according to any one of Items 1 to 6, which is used for exhausting tris (2,3-dibromopropyl) isocyanurate into at least the inside of a polyester fiber.
11. The flame-retardant processing for fibers according to any one of Items 1 to 6, comprising 0 to 30 parts by weight of a synthetic resin with respect to 100 parts by weight of total of tris (2,3-dibromopropyl) isocyanurate and the flame retardant. Agent.
12 Item 9. The production method according to Item 7 or 8, wherein tris (2,3-dibromopropyl) isocyanurate is exhausted at least inside the polyester fiber by a flame retardant treatment.
本発明の難燃加工剤によれば、有効成分（難燃化剤）として、ヘキサブロモシクロドデカンよりも環境面で有利なトリス（２，３−ジブロモプロピル）イソシアヌレートを採用していることから、ポリエステル繊維材料の後加工難燃化に好適に適用でき、繊維の洗濯耐久性を確保しつつ優れた難燃性をポリエステル繊維に付与できる。これにより、ヘキサブロモシクロドデカンの使用量を抑え、又はその使用量をゼロとすることができ、ヘキサブロモシクロドデカンの物性（難分解性、高蓄積性等）による環境問題を低減ないしは回避することが可能となる。 According to the flame retardant processing agent of the present invention, tris (2,3-dibromopropyl) isocyanurate, which is more environmentally friendly than hexabromocyclododecane, is used as an active ingredient (flame retardant). The polyester fiber material can be suitably applied to post-processing flame retarding, and excellent flame retardancy can be imparted to the polyester fiber while ensuring the washing durability of the fiber. As a result, the amount of hexabromocyclododecane used can be reduced, or the amount used can be reduced to zero, and environmental problems due to the physical properties of hexabromocyclododecane (such as difficulty decomposition and high accumulation) can be reduced or avoided. Is possible.
１．ポリエステル繊維用難燃加工剤
本発明のポリエステル繊維用難燃加工剤は、下記式（Ｉ）
1. Flame Retardant for Polyester Fiber The flame retardant for polyester fiber of the present invention is represented by the following formula (I)
で示されるトリス（２，３−ジブロモプロピル）イソシアヌレートを含むことを特徴とする。 It is characterized by including tris (2,3-dibromopropyl) isocyanurate represented by
トリス（２，３−ジブロモプロピル）イソシアヌレートは、難燃化剤としての役割を果たす化合物（本発明難燃剤）である。この化合物自体は公知であり、市販のものを使用することもできる。また、公知の製法によって合成することもできる。 Tris (2,3-dibromopropyl) isocyanurate is a compound that serves as a flame retardant (the flame retardant of the present invention). This compound is known per se, and a commercially available product can also be used. Moreover, it is also compoundable by a well-known manufacturing method.
本発明の難燃加工剤は、トリス（２，３−ジブロモプロピル）イソシアヌレートが分散媒中に分散されていることが好ましい。すなわち、分散液又は乳濁液（エマルション）の状態であることが好ましい。トリス（２，３−ジブロモプロピル）イソシアヌレートは融点が約１０５℃の化合物であるため、融点未満では固体で分散媒に分散した分散液、融点以上では液体で分散媒とともにエマルションの形態とすることができる。この場合の分散媒としては特に限定されず、水又は各種の有機溶媒が使用できるが、特に環境面を考慮すれば水を分散媒とすることが望ましい。 In the flame retardant processing agent of the present invention, tris (2,3-dibromopropyl) isocyanurate is preferably dispersed in a dispersion medium. That is, it is preferably in the state of a dispersion or an emulsion (emulsion). Since tris (2,3-dibromopropyl) isocyanurate is a compound having a melting point of about 105 ° C., it is a solid dispersion in a dispersion medium below the melting point, and a liquid above the melting point and in the form of an emulsion together with the dispersion medium. Can do. The dispersion medium in this case is not particularly limited, and water or various organic solvents can be used, but it is desirable to use water as the dispersion medium particularly considering environmental aspects.
トリス（２，３−ジブロモプロピル）イソシアヌレート微粒子が分散媒中に分散している場合の分散粒子の平均粒子径は特に限定的ではないが、繊維を難燃加工する場合の繊維への定着率（吸尽率）を考慮すると、通常１０μｍ以下とすれば良いが、好ましくは２μｍ以下、より好ましくは０．２〜２μｍ、最も好ましくは０．２〜１μｍとする。かかる平均粒子径に設定することによって、難燃加工時にトリス（２，３−ジブロモプロピル）イソシアヌレートをより確実にポリエステル繊維の少なくとも繊維内部（繊維表面及び繊維内部）に均一に吸尽（定着）させることが可能となる。上記の平均粒子径は、後記に示すホモジナイザー等の操作によって調節することができる。 The average particle diameter of the dispersed particles when tris (2,3-dibromopropyl) isocyanurate fine particles are dispersed in the dispersion medium is not particularly limited, but the fixing rate to the fiber when the fiber is flame-retardant processed In consideration of (exhaust rate), it is usually 10 μm or less, preferably 2 μm or less, more preferably 0.2 to 2 μm, and most preferably 0.2 to 1 μm. By setting the average particle size, tris (2,3-dibromopropyl) isocyanurate is more surely exhausted (fixed) at least inside the fiber (the fiber surface and inside the fiber) during flame-retardant processing. It becomes possible to make it. Said average particle diameter can be adjusted by operation, such as a homogenizer shown below.
本発明の難燃加工剤中におけるトリス（２，３−ジブロモプロピル）イソシアヌレートの含有量は限定されず、所望の難燃性、対象となる繊維の種類等に応じて適宜設定することができ、一般に２〜６０重量％、特に１０〜６０重量%、好ましくは２０〜５０重量%の範囲内で適宜設定することができる。 The content of tris (2,3-dibromopropyl) isocyanurate in the flame retardant processing agent of the present invention is not limited, and can be appropriately set according to the desired flame retardancy, the type of target fiber, and the like. Generally, it can be appropriately set within the range of 2 to 60% by weight, particularly 10 to 60% by weight, preferably 20 to 50% by weight.
また、本発明の難燃加工剤では、必要に応じて、本発明難燃剤以外の難燃剤（併用難燃剤）（本発明難燃剤及び併用難燃剤を総称して「難燃剤」という。）も用いることもできる。例えば、リン酸エステル系化合物（リン酸エステル系難燃剤）及びヘキサブロモシクロドデカンの少なくとも１種を用いることができる。前記のリン酸エステル系化合物としては、例えばトリオクチルホスフェート、トリフェニルホスフェート、トリクレジルホスフェート、トリキシレニルホスフェート、クレジルジフェニルホスフェート、クレジルジ２，６−キシレニルホスフェート、イソプロピルフェニルホスフェート、tert−ブチルフェニルホスフェート、ビフェニルジフェニルホスフェート、ナフチルジフェニルホスフェート、レゾルシノールビス（ジフェニルホスフェート）、レゾルシノールビス（ジキシレニルホスフェート）、ビスフェノールＡビス（ジフェニルホスフェート）、トリス（クロロプロピル）ホスフェート、トリス（ジクロロプロピル）ホスフェート、トリス（トリブロモネオペンチル）ホスフェート等の１種又は２種以上を用いることができる。これらの中でも、特に液状の併用難燃剤を用いることが好ましい。液状の併用難燃剤（常温・常圧で液状の併用難燃剤）を用いた場合、本発明による難燃化処理によって得られる難燃性ポリエステル繊維の風合いはよりいっそう柔軟なものとなり、カーテン等の風合いが重視されるような用途において特に有効となる。液状の併用難燃剤としては、例えばトリオクチルホスフェート、トリクレジルホスフェート、トリキシレニルホスフェート、クレジルジフェニルホスフェート、クレジルジ２，６−キシレニルホスフェート、イソプロピルフェニルホスフェート、tert−ブチルフェニルホスフェート、ビフェニルジフェニルホスフェート、レゾルシノールビス（ジフェニルホスフェート）、ビスフェノールＡビス（ジフェニルホスフェート）、トリス（クロロプロピル）ホスフェート、トリス（ジクロロプロピル）ホスフェート等の少なくとも１種を用いることができる。また、本発明の難燃剤では、前記の通り、ヘキサブロモシクロドデカンを用いることができるが、特にヘキサブロモシクロドデカンを含まないことが望ましい。 Moreover, in the flame retardant processing agent of the present invention, a flame retardant other than the flame retardant of the present invention (combination flame retardant) (the flame retardant of the present invention and the combined flame retardant are collectively referred to as “flame retardant”) as necessary. It can also be used. For example, at least one of a phosphate ester compound (phosphate ester flame retardant) and hexabromocyclododecane can be used. Examples of the phosphoric ester compounds include trioctyl phosphate, triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, cresyl di 2,6-xylenyl phosphate, isopropyl phenyl phosphate, tert- Butyl phenyl phosphate, biphenyl diphenyl phosphate, naphthyl diphenyl phosphate, resorcinol bis (diphenyl phosphate), resorcinol bis (dixylenyl phosphate), bisphenol A bis (diphenyl phosphate), tris (chloropropyl) phosphate, tris (dichloropropyl) phosphate, 1 type (s) or 2 or more types, such as a tris (tribromo neopentyl) phosphate, can be used. Among these, it is particularly preferable to use a liquid combined flame retardant. When using a liquid combined flame retardant (liquid combined flame retardant at room temperature and normal pressure), the texture of the flame retardant polyester fiber obtained by the flame retardant treatment according to the present invention becomes even more flexible, such as curtains. This is particularly effective in applications where the texture is important. Examples of liquid combined flame retardants include trioctyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, cresyl di-2,6-xylenyl phosphate, isopropyl phenyl phosphate, tert-butylphenyl phosphate, biphenyl diphenyl At least one of phosphate, resorcinol bis (diphenyl phosphate), bisphenol A bis (diphenyl phosphate), tris (chloropropyl) phosphate, tris (dichloropropyl) phosphate, and the like can be used. In the flame retardant of the present invention, hexabromocyclododecane can be used as described above, but it is particularly preferable that hexabromocyclododecane is not included.
リン酸エステル及び／又はヘキサブロモシクロドデカンの含有形態に関して特に限定するものではないが、液状の併用難燃剤の場合は、種々の乳化剤によってエマルションにしたものをトリス（２，３−ジブロモプロピル）イソシアヌレートの分散液に添加する方法が好ましい。また、固体の併用難燃剤の場合は、トリス（２，３−ジブロモプロピル）イソシアヌレートとともに分散液とする方法が好ましい。 Although it does not specifically limit regarding the inclusion form of phosphate ester and / or hexabromocyclododecane, in the case of a liquid combined flame retardant, what was made into an emulsion with various emulsifiers is tris (2,3-dibromopropyl) isocyanate. A method of adding to a dispersion of nurate is preferred. In the case of a solid combined flame retardant, a method of preparing a dispersion together with tris (2,3-dibromopropyl) isocyanurate is preferable.
併用難燃剤の含有量も特に限定されず、難燃効果の程度等を考慮して適宜設定できるが、通常１〜５０重量％程度、好ましくは３〜４０重量％とすれば良い。また、本発明難燃剤との割合は限定的ではないが、本発明難燃剤１００重量部に対して併用難燃剤１０〜２００重量部とすることが好ましい。 The content of the combined flame retardant is not particularly limited, and can be appropriately set in consideration of the degree of the flame retardant effect, but is usually about 1 to 50% by weight, preferably 3 to 40% by weight. Moreover, although a ratio with this invention flame retardant is not limited, it is preferable to set it as 10-200 weight part of combined use flame retardants with respect to 100 weight part of this invention flame retardants.
本発明の難燃加工剤では、トリス（２，３−ジブロモプロピル）イソシアヌレートの分散性、乳化性を高めるために、必要に応じて、公知の添加剤（分散剤、乳化剤、乳化安定化剤等）を含んでいても良い。また、本発明の難燃加工剤は合成樹脂を含んでいても良いが、難燃剤を繊維（フィラメント）に効果的に吸尽させ、より高い難燃性を付与するという見地より、難燃剤の合計１００重量部に対して合成樹脂を３０重量部以下、好ましくは１０重量部以下、より好ましくは５重量部以下、最も好ましくは０重量部とする。 In order to improve the dispersibility and emulsification of tris (2,3-dibromopropyl) isocyanurate in the flame retardant processing agent of the present invention, known additives (dispersant, emulsifier, emulsion stabilizer) Etc.) may be included. Further, the flame retardant processing agent of the present invention may contain a synthetic resin, but from the viewpoint of effectively exhausting the flame retardant to the fiber (filament) and imparting higher flame retardancy, The synthetic resin is 30 parts by weight or less, preferably 10 parts by weight or less, more preferably 5 parts by weight or less, and most preferably 0 parts by weight with respect to 100 parts by weight in total.
分散剤又は乳化剤（両者を総称して「分散剤」という。）としては、分散性又は乳化性を高めることができるものであれば特に限定されず、公知の分散剤又は乳化剤が使用できる。具体的には、アニオン界面活性剤及びノニオン界面活性剤の少なくとも１種が好適である。 A dispersant or an emulsifier (both are collectively referred to as “dispersant”) is not particularly limited as long as it can improve dispersibility or emulsifiability, and a known dispersant or emulsifier can be used. Specifically, at least one of an anionic surfactant and a nonionic surfactant is suitable.
アニオン界面活性剤としては、例えば高級アルコール硫酸エステル塩、ポリオキシエチレンアルキルフェニル硫酸エステル塩、硫酸化脂肪エステル塩、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸塩、高級アルコールリン酸エステル塩等が挙げられる。 Examples of the anionic surfactant include higher alcohol sulfates, polyoxyethylene alkylphenyl sulfates, sulfated fatty ester salts, alkylbenzene sulfonates, alkyl naphthalene sulfonates, higher alcohol phosphates, and the like. .
ノニオン界面活性剤としては、例えばポリオキシアルキレン天然油脂アルキルエーテル、ポリオキシアルキレン高級アルコールアルキルエーテル、ポリオキシアルキレンアルキルフェニルエーテル、多価アルコール脂肪酸エステル等が挙げられる。 Examples of nonionic surfactants include polyoxyalkylene natural oil alkyl ether, polyoxyalkylene higher alcohol alkyl ether, polyoxyalkylene alkylphenyl ether, polyhydric alcohol fatty acid ester and the like.
分散剤（界面活性剤）の添加量は特に限定されず、用いる分散剤の種類、分散又は乳化の程度等を考慮して適宜設定できる。例えば、分散媒が水である場合には、通常１〜３０重量％程度、好ましくは３〜２０重量％とすれば良い。他の分散媒を用いる場合もこれに準じて設定すれば良い。 The addition amount of the dispersant (surfactant) is not particularly limited, and can be appropriately set in consideration of the type of dispersant used, the degree of dispersion or emulsification, and the like. For example, when the dispersion medium is water, it is usually about 1 to 30% by weight, preferably 3 to 20% by weight. In the case of using another dispersion medium, it may be set according to this.
また、分散安定化剤又は乳化安定化剤（両者を総称して「安定化剤」という。）も使用できる。分散安定化剤としては、例えばポリビニルアルコール、ポリビニルピロリドン、メチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルセルロース、キサンタンガム、デンプン糊等の少なくとも１種が挙げられる。乳化安定化剤としては、例えばひまし油、菜種油等のトリグリセライド；リン酸エステル、フタル酸エステル等のエステル類；高級アルコール等が挙げられる。 Further, a dispersion stabilizer or an emulsion stabilizer (both are collectively referred to as “stabilizer”) can also be used. Examples of the dispersion stabilizer include at least one of polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, xanthan gum, starch paste, and the like. Examples of the emulsion stabilizer include triglycerides such as castor oil and rapeseed oil; esters such as phosphate esters and phthalate esters; higher alcohols and the like.
これらの安定化剤の含有量も特に限定されず、用いる安定化剤の種類、分散又は乳化の程度等を考慮して適宜設定できる。例えば、分散媒が水である場合には、通常０．１〜１０重量％程度、好ましくは１〜３重量％とすれば良い。他の分散媒を用いる場合もこれに準じて設定すれば良い。 The content of these stabilizers is not particularly limited, and can be appropriately set in consideration of the type of stabilizer used, the degree of dispersion or emulsification, and the like. For example, when the dispersion medium is water, it is usually about 0.1 to 10% by weight, preferably 1 to 3% by weight. In the case of using another dispersion medium, it may be set according to this.
本発明の難燃加工剤は、上記した界面活性剤（アニオン界面活性剤及びノニオン界面活性剤の少なくとも１種）と前記安定化剤との両方を含むことが好ましい。例えば、ポリビニルアルコール、ポリビニルピロリドン、メチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルセルロース、キサンタンガム及びデンプン糊の少なくとも１種の安定化剤（特にカルボキシメチルセルロース）と、アニオン界面活性剤の少なくとも１種（特にポリオキシエチレンアルキルフェニル硫酸エステル塩）の分散剤とを含むことが望ましい。これにより、分散粒子（粒径）等を安定化させ、繊維への吸尽をより効果的に行うことが可能となる。 The flame retardant processing agent of the present invention preferably contains both the above-described surfactant (at least one of an anionic surfactant and a nonionic surfactant) and the stabilizer. For example, polyvinyl alcohol, polyvinyl pyrrolidone, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, xanthan gum and starch paste (especially carboxymethyl cellulose) and at least one anionic surfactant (especially polyoxyethylene alkylphenyl) (Sulfate ester salt) dispersant. Thereby, it becomes possible to stabilize dispersed particles (particle diameter) and the like, and to exhaust the fibers more effectively.
本発明難燃加工剤の好適な組成としては、分散媒が水の場合では、トリス（２，３−ジブロモプロピル）イソシアヌレート１０〜６０重量％（好ましくは２０〜５０重量％程度）；分散剤（界面活性剤）１〜３０重量％（好ましくは３〜２０重量％程度）；安定化剤０．１〜１０重量％（好ましくは１〜３重量％程度）とする組成が例示される。場合によっては、併用難燃剤１〜５０重量％、好ましくは３〜４０重量％程度を含有した組成としても良い。 As a suitable composition of the flame retardant processing agent of the present invention, when the dispersion medium is water, 10 to 60% by weight (preferably about 20 to 50% by weight) of tris (2,3-dibromopropyl) isocyanurate; (Surfactant) 1 to 30% by weight (preferably about 3 to 20% by weight); Stabilizer 0.1 to 10% by weight (preferably about 1 to 3% by weight) is exemplified. Depending on the case, it is good also as a composition containing 1-50 weight% of combined flame retardants, Preferably about 3-40 weight%.
本発明の難燃加工剤の製造方法は、これらの成分を均一に混合・攪拌できる限り特に制限されない。例えば、所定の成分原料を混合後、ホモジナイザー、ボールミル、ビーズミル等の分散機により撹拌することにより本発明の難燃加工剤を調製することができる。撹拌条件は特に限定的ではないが、撹拌により得られる分散液は分散微粒子（難燃剤微粒子）の平均粒子径が１０μｍ以下、特に２μｍ以下、さらには０．２〜２μｍとなるように設定することが好ましい。 The method for producing the flame retardant finishing agent of the present invention is not particularly limited as long as these components can be uniformly mixed and stirred. For example, the flame retardant processing agent of the present invention can be prepared by mixing predetermined component materials and then stirring with a disperser such as a homogenizer, ball mill, or bead mill. The stirring conditions are not particularly limited, but the dispersion obtained by stirring should be set so that the average particle size of dispersed fine particles (flame retardant fine particles) is 10 μm or less, particularly 2 μm or less, and further 0.2 to 2 μm. Is preferred.
本発明の難燃加工剤では、本発明難燃剤であるトリス（２，３−ジブロモプロピル）イソシアヌレートをポリエステル繊維に吸尽させるための難燃加工剤として好適である。すなわち、本発明の難燃加工剤は、ポリエステル繊維の後加工難燃化（ポリエステル繊維を製造した後に難燃化処理すること）に好適に用いることができる。本発明の難燃加工剤を用いて難燃性ポリエステル繊維を製造する方法は次項２．で詳細に説明する。 The flame retardant processing agent of the present invention is suitable as a flame retardant processing agent for exhausting the tris (2,3-dibromopropyl) isocyanurate which is the flame retardant of the present invention to the polyester fiber. That is, the flame retardant processing agent of the present invention can be suitably used for post-processing flame-retarding of polyester fibers (combusting treatment after producing polyester fibers). The method for producing a flame retardant polyester fiber using the flame retardant processing agent of the present invention is described in 2. Will be described in detail.
２．難燃性ポリエステル繊維材料の製造方法
本発明は、ポリエステル繊維用難燃加工剤をポリエステル繊維に接触させることにより難燃化処理を行う工程を含むことを特徴とする難燃性ポリエステル繊維の製造方法を包含する。
2. BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention includes a method for producing a flame retardant polyester fiber, comprising a step of performing a flame retardant treatment by bringing a flame retardant processing agent for polyester fiber into contact with the polyester fiber. Is included.
対象となるポリエステル繊維は限定的でなく、例えばポリエチレンテレフタレートのほか、ポリメチレンテレフタレート等が挙げられる。本発明では、公知又は市販のポリエステル繊維のいずれにも適用できる。 The target polyester fiber is not limited, and examples include polyethylene terephthalate, polymethylene terephthalate, and the like. In the present invention, it can be applied to any known or commercially available polyester fiber.
前記工程としては、本発明の難燃加工剤中の難燃剤（微粒子）をポリエステル繊維に吸尽させることにより難燃性を付与する方法であれば特に限定されない。例えば、次の（１）（２）の方法によりポリエステル繊維を難燃加工（難燃化処理）することができる。 The step is not particularly limited as long as it is a method of imparting flame retardancy by exhausting the flame retardant (fine particles) in the flame retardant processing agent of the present invention to the polyester fiber. For example, the polyester fiber can be flame-retardant processed (flame retardant treatment) by the following methods (1) and (2).
（１）ポリエステル繊維用難燃加工剤をポリエステル繊維と接触させた後、前記ポリエステル繊維を乾燥させ、次いで前記ポリエステル繊維を１５０℃〜２００℃で熱処理することにより前記ポリエステル繊維の難燃化処理（難燃加工）を行う工程 (1) After making the flame-retardant processing agent for polyester fibers contact with the polyester fiber, the polyester fiber is dried, and then the polyester fiber is heat-treated at 150 ° C. to 200 ° C. (Flame retardant processing)
（２）１００〜１５０℃に加温したポリエステル繊維用難燃加工剤とポリエステル繊維とを接触させることにより前記ポリエステル繊維の難燃化処理（難燃加工）を行う工程 (2) A step of performing a flame retardant treatment (flame retardant treatment) of the polyester fiber by bringing the polyester fiber into contact with the flame retardant agent for polyester fiber heated to 100 to 150 ° C.
前記（１）又は（２）のいずれかの方法により、ポリエステル繊維用難燃加工剤中の難燃剤（微粒子）をポリエステル繊維に吸尽させることができる。この場合、いずれの加工方法においても、難燃加工剤は、必要に応じて水又は温湯により希釈して使用できる。 By the method of either (1) or (2), the flame retardant (fine particles) in the flame retardant processing agent for polyester fibers can be exhausted to the polyester fibers. In this case, in any processing method, the flame retardant processing agent can be diluted with water or hot water as needed.
前記（１）の加工方法では、難燃加工剤とポリエステル繊維とを接触後、該ポリエステル繊維を乾燥させて、次いで該ポリエステル繊維を１５０〜２００℃で熱処理して難燃加工剤中の難燃剤微粒子を吸尽させる。この場合、難燃加工剤は、分散媒（好ましくは水）で希釈して用いることができる。希釈する場合の難燃加工剤の濃度は特に限定されないが、通常は１〜５０重量％の範囲とすることが望ましい。 In the processing method of (1), after the flame retardant processing agent and the polyester fiber are contacted, the polyester fiber is dried, and then the polyester fiber is heat-treated at 150 to 200 ° C. Exhaust fine particles. In this case, the flame retardant finish can be diluted with a dispersion medium (preferably water). The concentration of the flame retardant finishing agent in the case of dilution is not particularly limited, but it is usually desirable to set it in the range of 1 to 50% by weight.
難燃加工剤とポリエステル繊維を接触させる方法は特に限定されず、ポリエステル繊維を難燃加工剤に浸漬する方法のほか、ポリエステル繊維に難燃加工剤を噴霧、塗布等する方法等が挙げられる。 The method for bringing the flame retardant processing agent into contact with the polyester fiber is not particularly limited, and examples thereof include a method in which the polyester fiber is immersed in the flame retardant processing agent and a method in which the flame retardant processing agent is sprayed and applied to the polyester fiber.
乾燥方法は特に限定されず、自然乾燥及び加熱乾燥の少なくとも１種が適用できる。加熱乾燥の場合の乾燥温度は通常６０〜１００℃程度であり、乾燥時間は通常５〜３０分程度である。 The drying method is not particularly limited, and at least one of natural drying and heat drying can be applied. In the case of heat drying, the drying temperature is usually about 60 to 100 ° C., and the drying time is usually about 5 to 30 minutes.
乾燥後、前記ポリエステル繊維を１５０〜２００℃、好ましくは１７０〜１８０℃で熱処理して難燃加工剤中の難燃剤微粒子を吸尽させる。熱処理時間は、熱処理温度、難燃加工剤の吸尽程度等に応じて適宜設定できるが、通常３０秒〜５分程度、好ましくは１〜２分である。なお、熱処理後、洗浄等を適宜行っても良い。 After drying, the polyester fiber is heat-treated at 150 to 200 ° C., preferably 170 to 180 ° C., to exhaust the flame retardant fine particles in the flame retardant processing agent. The heat treatment time can be appropriately set according to the heat treatment temperature, the exhaustion degree of the flame retardant processing agent, etc., but is usually about 30 seconds to 5 minutes, preferably 1 to 2 minutes. Note that washing and the like may be appropriately performed after the heat treatment.
前記（２）の加工方法では１００〜１５０℃に加温した難燃加工剤とポリエステル繊維とを接触させて、難燃加工剤中の難燃剤微粒子をポリエステル繊維に吸尽させる。この場合、難燃加工剤は、分散媒（例えば水）で希釈して用いることができる。希釈する場合の難燃加工剤の濃度は特に限定されないが、通常は０．１〜５０重量％の範囲とすることが望ましい。 In the processing method (2), the flame retardant processing agent heated to 100 to 150 ° C. and the polyester fiber are brought into contact with each other, and the flame retardant fine particles in the flame retardant processing agent are exhausted to the polyester fiber. In this case, the flame retardant processing agent can be used after diluted with a dispersion medium (for example, water). The concentration of the flame retardant processing agent in the case of dilution is not particularly limited, but it is usually desirable to be in the range of 0.1 to 50% by weight.
難燃加工剤の温度は１００〜１５０℃、好ましくは１２０〜１３０℃程度である。接触方法は特に限定されず、前記した浸漬、噴霧、塗布等が利用できる。例えば、浸漬の場合には、２〜６０分程度浸漬することにより難燃加工剤中の微粒子をポリエステル繊維に吸尽させることができる。処理後は、還元洗浄等を適宜行っても良い。前記（２）の加工方法は、例えば染色機等のような密閉容器中において実施することが好ましい。これにより高温・高圧下で難燃加工剤とポリエステル繊維を接触させることが可能となり、より効率的に難燃加工剤中の微粒子をポリエステル繊維に吸尽させることができる。 The temperature of the flame retardant is 100 to 150 ° C, preferably about 120 to 130 ° C. A contact method is not specifically limited, The above-mentioned immersion, spraying, application | coating, etc. can be utilized. For example, in the case of immersion, the polyester fiber can be exhausted with the fine particles in the flame retardant by immersion for about 2 to 60 minutes. After the treatment, reduction cleaning or the like may be appropriately performed. The processing method (2) is preferably carried out in a closed container such as a dyeing machine. Thereby, it becomes possible to contact the flame retardant and the polyester fiber under high temperature and high pressure, and the polyester fiber can be more efficiently exhausted by the fine particles in the flame retardant.
前記（１）（２）のいずれの加工方法でも、本発明の難燃加工剤は微粒子の平均粒子径が好ましくは０．２〜２μｍ程度と小さく、また分散安定性が高いため、難燃剤の微粒子がポリエステル繊維に吸尽されて繊維内部に拡散され易く、容易かつ確実に難燃性ポリエステル繊維を製造することができる。 In any of the above processing methods (1) and (2), the flame retardant processing agent of the present invention preferably has an average particle size of fine particles as small as about 0.2 to 2 μm and high dispersion stability. The fine particles are easily exhausted by the polyester fiber and easily diffused into the inside of the fiber, so that the flame-retardant polyester fiber can be produced easily and reliably.
以下に実施例及び比較例を示し、本発明をより具体的に説明する。但し、本発明は、実施例に限定されない。 Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the present invention is not limited to the examples.
実施例１
ポリオキシエチレンジスチレン化フェノールエーテル硫酸塩５重量部、カルボキシメチルセルロース（１０重量％水溶液）２重量部、水５３重量部の均一な混合液に、一般式（Ｉ）で表される粉末状トリス（２，３−ジブロモプロピル）イソシアヌレート４０重量部を添加し、この混合物をビーズミル（直径１．０〜１．４ｍｍガラスビーズ使用、アイメックス（株）製）にて、回転数２０００ｒｐｍ、粉砕時間３時間、循環方式で粉砕分散させて均一な白色分散液状の難燃加工剤を得た。得られた難燃加工剤の平均粒子径を粒度分布測定装置（レーザー回折／散乱式粒度分布測定装置ＬＡ−９１０、（株）堀場製作所製）により測定した結果、平均粒子径は０．９２７μｍであった。
Example 1
To a uniform mixed solution of 5 parts by weight of polyoxyethylene distyrenated phenol ether sulfate, 2 parts by weight of carboxymethyl cellulose (10% by weight aqueous solution), and 53 parts by weight of water, powdered tris represented by the general formula (I) ( 2,3-dibromopropyl) isocyanurate was added in an amount of 40 parts by weight, and this mixture was subjected to a rotation of 2000 rpm and a pulverization time of 3 hours in a bead mill (using glass beads having a diameter of 1.0 to 1.4 mm, manufactured by IMEX Co., Ltd.). Then, the mixture was pulverized and dispersed by a circulation method to obtain a uniform white dispersion liquid flame retardant. As a result of measuring the average particle diameter of the obtained flame retardant processing agent with a particle size distribution measuring device (Laser diffraction / scattering type particle size distribution measuring device LA-910, manufactured by Horiba, Ltd.), the average particle size was 0.927 μm. there were.
実施例２
ポリオキシエチレンジスチレン化フェノールエーテル硫酸塩５重量部、カルボキシメチルセルロース（１０重量％水溶液）２重量部、水４３重量部の均一な混合液に、一般式（Ｉ）で表される粉末状トリス（２，３−ジブロモプロピル）イソシアヌレート３０重量部を添加し、この混合物をビーズミル（直径１．０〜１．４ｍｍガラスビーズ使用、アイメックス（株）製）にて、回転数２０００ｒｐｍ、粉砕時間３時間、循環方式で粉砕分散させて均一な白色分散液を得た。
Example 2
To a uniform mixed liquid of 5 parts by weight of polyoxyethylene distyrenated phenol ether sulfate, 2 parts by weight of carboxymethyl cellulose (10% by weight aqueous solution) and 43 parts by weight of water, powdered tris represented by the general formula (I) ( 2,3-dibromopropyl) isocyanurate was added in an amount of 30 parts by weight, and this mixture was subjected to a rotation of 2000 rpm and a grinding time of 3 hours in a bead mill (diameter 1.0 to 1.4 mm using glass beads, manufactured by IMEX Co., Ltd.). Then, a uniform white dispersion was obtained by pulverization and dispersion in a circulating manner.
また、トリス（ジクロロプロピル）ホスフェート１０重量部、ポリオキシエチレンジスチレン化フェノールエーテル硫酸塩２重量部、硬化ひまし油ポリオキシエチレン付加物０．５重量部の均一な混合液に水７．５重量部を撹拌しながら少しずつ加えて乳化分散させ、均一な白色エマルションを得た。得られた分散液及びエマルションを混合し、均一な白色分散液状の難燃加工剤を得た。実施例１と同様にして平均粒子径を測定した結果、平均粒子径は０．８６２μｍであった。 In addition, 7.5 parts by weight of water in a uniform mixture of 10 parts by weight of tris (dichloropropyl) phosphate, 2 parts by weight of polyoxyethylene distyrenated phenol ether sulfate and 0.5 parts by weight of hardened castor oil polyoxyethylene adduct Was added little by little while stirring to obtain a uniform white emulsion. The obtained dispersion and emulsion were mixed to obtain a uniform white dispersion liquid flame retardant. As a result of measuring the average particle size in the same manner as in Example 1, the average particle size was 0.862 μm.
実施例３
ポリオキシエチレンジスチレン化フェノールエーテル硫酸塩５重量部、カルボキシメチルセルロース（１０重量％水溶液）２重量部、水５３重量部の均一な混合液に、一般式（Ｉ）で表される粉末状トリス（２，３−ジブロモプロピル）イソシアヌレート３０重量部、ヘキサブロモシクロドデカン（マナック（株）製）１０重量部を添加し、この混合物をビーズミル（直径１．０〜１．４ｍｍガラスビーズ使用、アイメックス（株）製）にて、回転数２０００ｒｐｍ、粉砕時間３時間、循環方式で粉砕分散させて均一な白色分散液状の難燃加工剤を得た。実施例１と同様にして平均粒子径を測定した結果、平均粒子径は０．７９１μｍであった。
Example 3
To a uniform mixed solution of 5 parts by weight of polyoxyethylene distyrenated phenol ether sulfate, 2 parts by weight of carboxymethyl cellulose (10% by weight aqueous solution), and 53 parts by weight of water, powdered tris represented by the general formula (I) ( 2,3-dibromopropyl) isocyanurate 30 parts by weight and hexabromocyclododecane (manac Co., Ltd.) 10 parts by weight were added, and this mixture was added to a bead mill (diameter 1.0 to 1.4 mm glass beads, Imex ( Manufactured by the same company), and pulverized and dispersed by a circulation method at a rotational speed of 2000 rpm and a pulverization time of 3 hours to obtain a uniform white dispersed liquid flame retardant. As a result of measuring the average particle size in the same manner as in Example 1, the average particle size was 0.791 μm.
参考例１
前記式（Ｉ）で表される粉末状トリス（２，３−ジブロモプロピル）イソシアヌレートの代わりにヘキサブロモシクロドデカンを用い、実施例１と同様に粉砕分散させ均一な白色分散液状の難燃加工剤を得た。実施例１と同様にして平均粒子径を測定した結果、平均粒子径は０．６７３μｍであった。
Reference example 1
In place of powdered tris (2,3-dibromopropyl) isocyanurate represented by the above formula (I), hexabromocyclododecane is used and pulverized and dispersed in the same manner as in Example 1 to obtain a uniform white dispersion liquid flame retardant processing An agent was obtained. As a result of measuring the average particle size in the same manner as in Example 1, the average particle size was 0.673 μm.
試験例１
実施例１〜３及び参考例１で調製した難燃加工剤を用い、ポリエステル繊維を難燃加工し、得られた難燃性ポリエステル繊維の難燃性確認試験を実施した。ポリエステル繊維としては次の２種類を用いた。
Test example 1
Using the flame retardant processing agent prepared in Examples 1 to 3 and Reference Example 1, the polyester fiber was flame retardant processed, and the flame retardant confirmation test of the obtained flame retardant polyester fiber was performed. The following two types of polyester fibers were used.
試験布１：難燃化処理が非常に困難であるレギュラーポリエステルとカチオン可染性ポリエステルとから構成された、目付量１３５ｇ／ｍ２であるカーテン用レギュラーポリエステル／カチオン可染性ポリエステル織物（６０／４０） Test Cloth 1: Regular polyester / cationic dyeable polyester fabric for curtains having a basis weight of 135 g / m 2 and composed of a regular polyester and a cationic dyeable polyester that are very difficult to flame-retardant (60 / 40)
試験布２：目付量３５０ｇ／ｍ２であるカーシート用ポリエステル編地 Test cloth 2: Polyester knitted fabric for car seats having a basis weight of 350 g / m 2
＜難燃加工＞
難燃加工方法としては、次の加工例１、加工例２及び加工例３の３種類を採用した。
<Flame retardant processing>
As the flame retardant processing method, the following three types of processing example 1, processing example 2 and processing example 3 were adopted.
加工例１：各難燃加工剤を２０重量％含むように調製された４種類の処理液で、試験布１をパディング処理（絞り率６０％）後、８０℃で５分間乾燥した。次いで１８０℃で１分間熱処理を行った。その後、下記組成の洗浄液にて６０℃で５分間洗浄を行い、８０℃で５分間乾燥を行って難燃加工を施した。
「洗浄液」ソーダ灰 １．０ｇ／Ｌ
Processing Example 1: Test cloth 1 was padded (squeezing rate 60%) with four types of treatment liquids prepared so as to contain 20% by weight of each flame retardant, and then dried at 80 ° C. for 5 minutes. Next, heat treatment was performed at 180 ° C. for 1 minute. Then, it wash | cleaned for 5 minutes at 60 degreeC with the washing | cleaning liquid of the following composition, and it dried for 5 minutes at 80 degreeC, and gave the flame-retardant process.
"Cleaning liquid" soda ash 1.0g / L
加工例２：試験布１を、ミニカラー染色機（テクサム技研社製）を用いて下記の組成の吸尽処理液（染色と同時に難燃性を付与できる処理液）にて、浴比１：１０、温度４０℃で５分処理後、１３０℃まで３℃／分で昇温して、１３０℃で４０分間染色する条件で浴中処理を行った。次いで、８０℃まで冷却後、下記組成の還元洗浄処理液により還元洗浄を行ってすすぎを行い、次いで乾燥後、１８０℃で１分間ヒートセットして難燃加工を施した。 Processing example 2: Using test cloth 1 with a mini color dyeing machine (manufactured by Teksam Giken Co., Ltd.) with an exhaust treatment solution (treatment solution capable of imparting flame retardancy simultaneously with dyeing), bath ratio 1: 10. After treatment at a temperature of 40 ° C. for 5 minutes, the temperature was increased to 130 ° C. at a rate of 3 ° C./minute, and the treatment was carried out in a bath under conditions of dyeing at 130 ° C. for 40 minutes. Subsequently, after cooling to 80 ° C., reduction cleaning was performed with a reduction cleaning treatment liquid having the following composition, followed by rinsing, followed by drying and heat setting at 180 ° C. for 1 minute for flame retardant processing.
「吸尽処理液」：on the weight of fiberを示す。
・カヤロンマイクロエステル レッドＡＱ−ＬＥ（分散染料、日本化薬(株)製）０．１％o.w.f
・カヤロンマイクロエステル ブルーＡＱ−ＬＥ（分散染料、日本化薬(株)製）０．１o.w.f
・カヤロンマイクロエステル イエローＡＱ−ＬＥ（分散染料、日本化薬(株)製）０．１o.w.f
・カヤクリルレッド ＧＬ−ＥＤ（分散型カチオン染料、日本化薬(株)製）０．１％o.w.f
・カヤクリルブルー ＧＳＬ−ＥＤ（分散型カチオン染料、日本化薬(株)製）０．１％o.w.f
・カヤクリルイエロー ３ＲＬ−ＥＤ（分散型カチオン染料、日本化薬(株)製）０．１％o.w.f
・レベノールＴＤ−６６０（分散均染剤、北広ケミカル(株)製）０．５ｇ／Ｌ
・酢酸（ｐＨ調整剤）０．１５ｍＬ／Ｌ
・難燃加工剤（実施例１〜３及び参考例１で得た難燃加工剤）２０%o.w.f
“Exhaust treatment liquid”: on the weight of fiber.
・ Kayaron Microester Red AQ-LE (disperse dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1% owf
・ Kayaron Microester Blue AQ-LE (disperse dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1o.wf
・ Kayaron Microester Yellow AQ-LE (disperse dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1o.wf
-Kayacrill Red GL-ED (dispersed cationic dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1% owf
・ Kayacriru Blue GSL-ED (dispersed cationic dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1% owf
-Kayacrill Yellow 3RL-ED (dispersed cationic dye, manufactured by Nippon Kayaku Co., Ltd.) 0.1% owf
・ Lebenol TD-660 (dispersion leveling agent, manufactured by Kitahiro Chemical Co., Ltd.) 0.5g / L
Acetic acid (pH adjuster) 0.15 mL / L
・ Flame retardant (flame retardant obtained in Examples 1 to 3 and Reference Example 1) 20% owf
「還元洗浄処理液」
・ハイドロサルファイトナトリウム １．０ｇ／Ｌ
・ソーダ灰 １．０ｇ／Ｌ
"Reduction cleaning solution"
・ Hydrosulfite sodium 1.0g / L
・ Soda ash 1.0g / L
加工例３：試験布２を、ミニカラー染色機（テクサム技研社製）を用いて下記の組成の吸尽処理液（染色と同時に難燃性を付与できる処理液）にて、浴比１：１５、温度４０℃で５分処理後、１３０℃まで３℃／分で昇温して、１３０℃で４０分間染色する条件で浴中処理を行った。次いで、８０℃まで冷却後、下記組成の還元洗浄処理液により還元洗浄を行ってすすぎを行い、次いで乾燥後、１８０℃で１分間ヒートセットして難燃加工を施した。 Processing Example 3: Using test cloth 2 with a mini color dyeing machine (manufactured by Teksam Giken Co., Ltd.) with an exhaust treatment solution having the following composition (treatment solution that can impart flame retardancy simultaneously with dyeing), bath ratio 1: 15. After treatment at a temperature of 40 ° C. for 5 minutes, the temperature was increased to 130 ° C. at 3 ° C./minute, and the treatment was performed in a bath under conditions of dyeing at 130 ° C. for 40 minutes. Subsequently, after cooling to 80 ° C., reduction cleaning was performed with a reduction cleaning treatment liquid having the following composition, followed by rinsing, followed by drying and heat setting at 180 ° C. for 1 minute for flame retardant processing.
「吸尽処理液」：on the weight of fiberを示す。
・カヤロンポリエステル ブラックＡＵＬ−Ｅ（分散染料、日本化薬(株)製）７％o.w.f
・酢酸（ｐＨ調整剤）０．１５ｍＬ／Ｌ
・難燃加工剤（実施例１〜３及び参考例１で得た難燃加工剤）５%o.w.f
“Exhaust treatment liquid”: on the weight of fiber.
-Kayalon polyester black AUL-E (disperse dye, manufactured by Nippon Kayaku Co., Ltd.) 7% owf
Acetic acid (pH adjuster) 0.15 mL / L
・ Flame retardant (flame retardant obtained in Examples 1 to 3 and Reference Example 1) 5% owf
「還元洗浄処理液」
・ハイドロサルファイトナトリウム ２．０ｇ／Ｌ
・ソーダ灰 ２．０ｇ／Ｌ
"Reduction cleaning solution"
・ Hydrosulfite sodium 2.0g / L
・ Soda ash 2.0g / L
＜難燃性確認試験：燃焼試験＞
上記により得られた難燃性ポリエステル繊維について、以下の難燃性評価を行った。
<Flame retardance confirmation test: Combustion test>
The following flame retardant evaluation was performed about the flame retardant polyester fiber obtained by the above.
加工例１及び加工例２で得られた難燃性ポリエステル繊維については、ＪＩＳ Ｌ−１０９１ Ａ−１（ミクロバーナー法）とＪＩＳ Ｌ−１０９１ Ｄ（４５°コイル法）による難燃性評価試験を行った。また、難燃性評価試験は、昭和６１年２月２１日消防庁告示第１号に準じて水洗濯及びドライクリーニングを５回行ったものに対しても行った。評価に当たっては、ＪＩＳ Ｌ−１０９１に規定される残炎時間及び接炎回数をそれぞれ３回測定した。各々の難燃加工液で処理された難燃加工繊維試料の難燃性評価結果を表１に示す。なお、難燃加工処理に供したポリエステル系繊維の難燃未加工繊維についても、同様の試験を行った。その結果を表１に示す。 About the flame-retardant polyester fiber obtained in processing example 1 and processing example 2, the flame-retardant evaluation test by JIS L-1091 A-1 (micro burner method) and JIS L-1091 D (45 degree coil method) went. In addition, the flame retardancy evaluation test was also performed on water washing and dry cleaning performed five times in accordance with the Fire and Disaster Management Agency Notification No. 1 on February 21, 1986. In the evaluation, the afterflame time and the number of times of flame contact specified in JIS L-1091 were measured three times. Table 1 shows the results of flame retardancy evaluation of flame retardant processed fiber samples treated with each flame retardant processing liquid. In addition, the same test was done also about the flame-retardant unprocessed fiber of the polyester-type fiber used for the flame-retardant processing. The results are shown in Table 1.
加工例３で得られた難燃性ポリエステル繊維については、ＦＭＶＳＳ−３０２による難燃性評価を行った。評価に当たっては、ＦＭＶＳＳ−３０２に規定される、標線を越えてからの燃焼距離、標線を越えてからの燃焼時間、標線を越えてからの燃焼速度をそれぞれ３回測定した。各々の難燃加工液で処理された難燃加工繊維試料の難燃性評価結果を表２に示す。なお、難燃加工処理に供したポリエステル系繊維の難燃未加工繊維についても、同様の試験を行った。その結果を表２に示す。 About the flame-retardant polyester fiber obtained in the processing example 3, the flame-retardant evaluation by FMVSS-302 was performed. In the evaluation, the combustion distance after exceeding the marked line, the burning time after exceeding the marked line, and the burning rate after exceeding the marked line, which are defined in FMVSS-302, were measured three times. Table 2 shows the results of flame retardancy evaluation of the flame retardant processed fiber samples treated with each flame retardant processing liquid. In addition, the same test was done also about the flame-retardant unprocessed fiber of the polyester-type fiber used for the flame-retardant processing. The results are shown in Table 2.
表１及び表２の結果からも明らかなように、本発明難燃剤を含む実施例１〜３は、難燃剤としてヘキサブロモシクロドデカンを用いた参考例１と同等の優れた難燃性を付与できることがわかる。 As is apparent from the results of Tables 1 and 2, Examples 1 to 3 containing the flame retardant of the present invention impart excellent flame retardancy equivalent to Reference Example 1 using hexabromocyclododecane as the flame retardant. I understand that I can do it.
＜剛軟性試験＞
加工例１及び２で得られた難燃性ポリエステル繊維について、ＪＩＳ Ｌ−１０９６ 剛軟性 Ａ法（４５°カンチレバー法）による剛軟性試験を行った。試験は、ＪＩＳ Ｌ−１０９６に規定される試験片が移動した長さを、たて方向及びよこ方向のそれぞれ６回測定した。各々の難燃加工液で処理された難燃加工繊維試料の剛軟性評価結果を表３に示す。なお、難燃未加工のポリエステル系繊維についても同様の試験を行った。その結果も併せて表３に示す。
<Flexibility test>
The flame-retardant polyester fiber obtained in Processing Examples 1 and 2 was subjected to a bending resistance test according to JIS L-1096 bending resistance A method (45 ° cantilever method). In the test, the length of movement of the test piece defined in JIS L-1096 was measured 6 times in the vertical direction and the horizontal direction. Table 3 shows the evaluation results of the bending resistance of the flame-retardant processed fiber samples treated with the respective flame-retardant processing liquids. A similar test was also conducted on the flame-retardant unprocessed polyester fiber. The results are also shown in Table 3.
表３の結果からも明らかなように、本発明の難燃剤のうち液状の併用難燃剤を用いた実施例２は、未併用の実施例１よりも柔軟性に優れ、難燃剤としてヘキサブロモシクロドデカンを用いた参考例１により近い風合いを維持して難燃処理できたことがわかる。 As is clear from the results in Table 3, Example 2 using the liquid combined flame retardant of the present invention is superior in flexibility to the non-combined Example 1, and hexabromocyclo is used as the flame retardant. It can be seen that the flame retardant treatment can be performed while maintaining a texture closer to that of Reference Example 1 using dodecane.
本発明における難燃加工剤及びそれを用いて製造された難燃性ポリエステル繊維用途の代表例として、カーテン、布製ブラインド等の各種インテリア用途、カーシート等の自動車内装材用途等が挙げられるが、特に限定されるものではなく、ポリエステル系繊維製品全般に幅広く用いることができる。 As typical examples of flame retardant processing agents and flame retardant polyester fiber applications produced using the same in the present invention, various interior applications such as curtains and cloth blinds, automotive interior materials applications such as car seats, etc. It is not particularly limited, and can be widely used for polyester fiber products in general.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011032588A (en) * | 2009-07-29 | 2011-02-17 | Komatsu Seiren Co Ltd | Flame retardant agent and flame retardant method for polyester fiber product |
| JP2011195984A (en) * | 2010-03-18 | 2011-10-06 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame retardant and flame retarding method for polyester fiber |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62181390A (en) * | 1986-02-05 | 1987-08-08 | Marubishi Yuka Kogyo Kk | Flame-retardant composition |
| WO2006035868A1 (en) * | 2004-09-29 | 2006-04-06 | Kaneka Corporation | Flame-retardant polyester artificial hair |
| JP2007284830A (en) * | 2006-04-18 | 2007-11-01 | Dainippon Ink & Chem Inc | Agent for imparting flame retardancy to polyester fabric, and flame-retardant polyester fabric finished by using the same |
| JP2009203595A (en) * | 2007-09-26 | 2009-09-10 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame retarding processing agent for polyester fiber and processing method thereof |
-
2008
- 2008-12-25 JP JP2008329308A patent/JP2009174109A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62181390A (en) * | 1986-02-05 | 1987-08-08 | Marubishi Yuka Kogyo Kk | Flame-retardant composition |
| WO2006035868A1 (en) * | 2004-09-29 | 2006-04-06 | Kaneka Corporation | Flame-retardant polyester artificial hair |
| JP2007284830A (en) * | 2006-04-18 | 2007-11-01 | Dainippon Ink & Chem Inc | Agent for imparting flame retardancy to polyester fabric, and flame-retardant polyester fabric finished by using the same |
| JP2009203595A (en) * | 2007-09-26 | 2009-09-10 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame retarding processing agent for polyester fiber and processing method thereof |
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| WO2012081499A1 (en) * | 2010-12-17 | 2012-06-21 | 第一工業製薬株式会社 | Processing aid for flameproofing fiber, and flameproofing method |
| JP2012127037A (en) * | 2010-12-17 | 2012-07-05 | Dai Ichi Kogyo Seiyaku Co Ltd | Processing aid for fiber flame retardant and method for flame retardant |
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