JP2004225176A - Flame-retardant finishing agent for polyester-based synthetic fiber, flame-retardant processing method using the same and flame-retardant polyester-based synthetic fiber - Google Patents
Flame-retardant finishing agent for polyester-based synthetic fiber, flame-retardant processing method using the same and flame-retardant polyester-based synthetic fiber Download PDFInfo
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 74
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 229920000728 polyester Polymers 0.000 title claims abstract description 44
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- 239000007787 solid Substances 0.000 abstract description 4
- UHQIQVGJUUTUDH-UHFFFAOYSA-N (3-oxo-6,7,8,9-tetraphenyl-2,4-dioxa-3lambda5-phosphabicyclo[3.2.2]nona-1(7),5,8-trien-3-yl) dihydrogen phosphate Chemical compound C=1C=CC=CC=1C1=C(C(C=2C=CC=CC=2)=C2C=3C=CC=CC=3)OP(OP(O)(=O)O)(=O)OC2=C1C1=CC=CC=C1 UHQIQVGJUUTUDH-UHFFFAOYSA-N 0.000 abstract 1
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- 229910019142 PO4 Inorganic materials 0.000 description 2
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- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
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Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、ポリエステル系合成繊維に対し耐久性に優れる難燃性を付与することができる難燃加工剤、それを用いた難燃加工方法、及び、該方法により得られる難燃性ポリエステル系合成繊維に関するものである。
【０００２】
【従来の技術】
従来、ポリエステル系合成繊維に対し後加工により難燃性を付与するための難燃加工剤としては、ヘキサブロモシクロドデカンなどのハロゲン系化合物を水に分散または乳化させたものが一般に使用されてきた。しかし、このようなハロゲン系難燃加工剤で処理されたポリエステル系合成繊維は、燃えるとブロムダイオキシンなどの有害なハロゲン化ガスが発生する危惧があり、脱ハロゲン化の要請が高まっている。
【０００３】
そこで、有機リン酸エステルのようなリン化合物を使用した難燃加工剤が使用されているが、従来一般に難燃剤として用いられているリン化合物は、化合物中におけるリンの含有率が低く、また、その分子量が低いことからポリエステル系合成繊維の引火点以下で分解、揮散してしまい、そのため十分な難燃性を付与することが困難である。従って、従来はリン化合物を大量に処理する必要があり、その処理量の多さから、風合い低下を招いたり、経時的に繊維表面に染料共々ブリードを生じ、染色、摩擦堅牢度を低下させるという問題があった。
【０００４】
このような問題を解決するために、難燃剤として分子量の大きいジホスフェート化合物を使用することも提案されている。例えば、下記特許文献１には、レゾルシノールビス（ジフェニルホスフェート）を界面活性剤の存在下に水に乳化分散させて水乳化体を調製し、これを難燃加工剤としてポリエステル系合成繊維に付与する難燃加工方法が開示されている。
【０００５】
【特許文献１】特開２０００−３２８４４５号公報
【０００６】
【発明が解決しようとする課題】
上記特許文献１に開示された難燃加工剤は、難燃剤としてジホスフェート化合物を単独で使用するものであるが、本発明者において検討したところ、このようなジホスフェート化合物単独では、実際上要求されているような耐久難燃性を得るのが難しいことが判明した。すなわち、上記のジホスフェート化合物は難燃剤としては分子量が大きいため、それ単独ではポリエステル系合成繊維の繊維表面には付着（吸着）しても、繊維内部に吸収される現象を伴う収着は起こりにくい。単に繊維表面に付着した難燃剤は、還元洗浄等のアルカリソーピングや、ドライクリーニングなどの溶剤で脱落してしまうので、十分な耐久難燃性、特にドライクリーニングに対する耐久性を得ることはできない。
【０００７】
本発明は、以上の点に鑑みてなされたものであり、風合いや摩擦堅牢度を損なうことなく、リン系難燃剤の収着量を高めて耐久性に優れた難燃性を付与することのできる難燃加工剤、それを用いた難燃加工方法、及び、耐久難燃性に優れるポリエステル系合成繊維を提供することを目的とする。
【０００８】
【課題を解決するための手段】
本発明者らは、鋭意研究を重ねた結果、上記したジホスフェート化合物とともに常温固体のトリフェニルホスフェートを併用することにより、ポリエステル系合成繊維に収着するリン系難燃剤の量を増加させることができ、ジホスフェート化合物単独処方では得られなかった洗濯、ドライクリーニングに対する耐久難燃性が得られることを見い出し、本発明を完成するに至った。
【０００９】
すなわち、本発明によれば、テトラフェニル−ｍ−フェニレンジホスフェート及び／又はテトラフェニル−ｐ−フェニレンジホスフェートからなるジホスフェート化合物と、トリフェニルホスフェートとを含有する水分散体または水乳化体からなるポリエステル系合成繊維の難燃加工剤が提供される。
【００１０】
本発明によれば、また、上記難燃加工剤を用い、高温吸尽法又はパッドサーモ法によりポリエステル系合成繊維に収着させることを特徴とするポリエステル系合成繊維の難燃加工方法が提供される。
【００１１】
本発明によれば、更に、上記方法により難燃化された難燃性ポリエステル系合成繊維が提供される。
【００１２】
【発明の実施の形態】
本発明の難燃加工剤において、難燃剤として用いられるジホスフェート化合物は、下記式（１）で表されるテトラフェニル−ｍ−フェニレンジホスフェートと、下記式（２）で表されるテトラフェニル−ｐ−フェニレンジホスフェートであり、両者はいずれか一方だけ用いても併用してもよい。
【００１３】
【化１】
本発明の難燃加工剤において、前記ジホスフェート化合物とともに難燃剤として用いられるトリフェニルホスフェート（ＴＰＰ）は、下記式（３）で表される。
【００１５】
【化２】
上記ジホスフェート化合物は、化合物中に含まれるリンの含有率が高く、また分子量も大きいので、優れた難燃効果を発揮するが、分子量が大きいことに起因してポリエステル系合成繊維に対し収着しにくいという欠点がある。そこで、常温固体で収着向上効果のあるＴＰＰを併用することにより、ポリエステル系合成繊維に収着するリン化合物を増加させ、優れた耐久難燃性を付与することができる。また、ＴＰＰは低分子量であるが、常温で固体であるためマイグレーションしにくく、従って染料を連れ添って繊維表面にブリードアウトしにくいものであり、そのため染色堅牢度の低下を抑えることができる。なお、収着とは、難燃剤であるリン化合物が繊維表面に吸着するときに繊維内部への吸収を伴う現象をいうが、必ずしもリン化合物の構造全体が繊維内部に入り込んでいる必要はなく、構造の一部、例えば端部のフェニル基のみが繊維内部に入り込んでいるような場合も含まれる。
【００１７】
上記ジホスフェート化合物とＴＰＰとの比率は、ジホスフェート化合物が難燃剤成分中４０〜８０重量％、ＴＰＰが難燃剤成分中２０〜６０重量％であることが好ましい。
【００１８】
本発明の難燃加工剤は、上記ジホスフェート化合物とＴＰＰとを、界面活性剤の存在下、水中に分散もしくは乳化させて得られる水分散体もしくは水乳化体である。その際の界面活性剤としては、非イオン界面活性剤とアニオン界面活性剤のいずれか一方又は双方組み合わせて用いられる。
【００１９】
非イオン界面活性剤の具体例としては、ポリオキシアルキレンアルキルフェニルエーテル、ポリオキシアルキレンアルキルエーテル、ポリオキシアルキレンアルキルエステル、多価アルコール脂肪酸エステルアルキレンオキサイド付加物、高級アルキルアミンアルキレンオキサイド付加物、脂肪酸アミドアルキレンオキサイド付加物、アルキルグリコシド、ショ糖脂肪酸エステル等が挙げられる。好ましくは、ポリオキシエチレンジスチレン化フェニルエーテル、ポリオキシエチレントリスチレン化フェニルエーテルが挙げられる。
【００２０】
アニオン界面活性剤の具体例としては、高級アルコール硫酸エステル塩、高級アルキルエーテル硫酸エステル塩、硫酸化脂肪酸エステル等のアルキルサルフェート塩や、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等のアルキルスルホネート塩、更には、高級アルコールリン酸エステル塩、高級アルコールのアルキレンオキサイド付加物リン酸エステル塩等のアルキルホスフェート塩が挙げられる。また、アルキルアリールスルホネート塩、ポリオキシアルキレンアルキルエーテルサルフェート塩、ポリオキシアルキレンアルキルエステルホスフェート塩、ポリオキシアルキレンアルキルエーテルカルボキシレート塩、ポリカルボン酸塩、ロート油、石油スルホネート、アルキルジフェニルエーテルスルホネート塩等が挙げられる。好ましくは、ポリオキシエチレンジスチレン化もしくはトリスチレン化フェニルエーテル硫酸エステル塩である。
【００２１】
このような界面活性剤の使用量は特に限定されないが、通常、難燃剤成分であるリン化合物に対して１０〜３０重量％の範囲内で用いられる。
【００２２】
本発明の難燃加工剤において、難燃剤成分であるリン化合物の含有量は、通常、３０〜５０重量％の範囲内である。なお、本発明の難燃加工剤においては、分散もしくは乳化状態を安定化させるため、メチルアルコール、エチルアルコール、トルエン、エチレングリコール及びブチルセロソルブ等の有機溶剤を含有してもよい。また、紫外線吸収剤や酸化防止剤等の各種添加剤を配合することもできる。
【００２３】
本発明の難燃加工剤は、ポリエステル系合成繊維に対し後加工処理により難燃性を付与するために用いられるものであり、このような後加工処理としては高温吸尽法やパッドサーモ法等が挙げられる。
【００２４】
高温吸尽法では、難燃加工剤を添加した処理浴中にポリエステル系合成繊維を浸漬し、高温（通常８０℃以上、好ましくは１１０〜１５０℃）で所定時間（例えば２〜６０分間）処理することにより、難燃剤を繊維に収着させる。好ましくは、難燃剤を染料と同時に繊維に収着させる染色同浴法によることである。すなわち、難燃加工剤を染色浴に添加しておいて、この染色浴中にポリエステル系合成繊維を浸漬して、高温にて吸尽処理を行うことが効率的であり好ましい。
【００２５】
また、パッドサーモ法では、難燃加工剤を含む液にポリエステル系合成繊維を浸漬し、所定の付着量になるようにマングル等で絞り、乾熱処理や、過熱スチーム処理などの蒸熱処理によって熱処理を行うことにより、難燃剤を繊維に収着させる。熱処理温度は通常１１０〜２１０℃の範囲内である。好ましくは、浸漬後、マングルで絞り、乾燥、熱セットを行うパッド・ドライ・サーモキュア法により処理することである。
【００２６】
なお、加工対象となるポリエステル系合成繊維は、ポリエチレンテレフタレートやポリブチレンテレフタレートなどのポリエステル、あるいはこれらにイソフタル酸、イソフタル酸スルホネート、アジピン酸、ポリエチレングリコールなどの第３成分を共重合又はブレンドして得られるポリエステルからなる繊維であり、長繊維でも短繊維でもよい。また、繊維の形態としては、糸、織編物、不織布、ロープなどの繊維製品であれば特に限定されるものではない。また、かかるポリエステル系合成繊維には、本発明の効果を阻害しない範囲で、他の合成繊維、天然繊維、半合成繊維が混合されてもよい。
【００２７】
【実施例】
以下に、実施例を挙げて本発明をさらに詳細に説明するが、本発明はこれらの実施例に限定されるものではない。なお、実施例中の「部」は重量部、「％」は重量％を示す。
【００２８】
１．評価方法
（１）製品安定性
難燃加工剤を３０日間常温放置し、放置後の水分散体もしくは水乳化体の状態を評価した。評価は、離水や分離が発生せず作製直後の状態を保持している場合を「○」、離水や分離が発生し振盪しても元の分散もしくは乳化状態に復元不可能な場合を「×」、軽度な離水や分離で振盪すれば元の分散もしくは乳化状態に復元する場合を「△」とした。
【００２９】
（２）難燃性
難燃加工した織物について、加工上りのものと、これを下記条件で水洗濯又はドライクリーニングしたものについて、ＪＩＳ Ｌ １０９１ Ａ−１法（ミクロバーナー法）及びＪＩＳ Ｌ １０９１ Ｄ法（コイル法）にて難燃性を測定した。ミクロバーナー法では、１分加熱及び着炎３秒後ともに、残炎が３秒以下で、残塵が５秒以下であり、かつ炭化面積が３０ｃｍ２以下のものを「○」とし、それ以外を「×」とした。コイル法においては接炎回数が３回以上であるものを「○」とし、２回以下であるものを「×」とした。
【００３０】
（水洗濯）ＪＩＳ Ｋ ３３７１に従って、弱アルカリ性第１種洗剤を１ｇ／Ｌの割合で用い、浴比１：４０として、６０℃±２℃で１５分間水洗濯した後、４０℃±２℃で５分間のすすぎを３回行い、遠心脱水を２分間行い、その後、６０℃±５℃で熱風乾燥する処理を１回として、これを５回行った。
【００３１】
（ドライクリーニング）試料１ｇにつき、テトラクロロエチレン１２．６ｍＬ、チャージソープ（ノニオン界面活性剤／アニオン界面活性剤／水＝１０／１０／１（重量比））０．２６５ｇを用いて、３０℃±２℃で１５分間の処理を１回とし、これを５回行った。
【００３２】
（３）染色堅牢度
濃色染料で難燃加工した織物について、ＪＩＳ Ｌ ０８４９ ６．１（２）乾燥試験、もしくは６．２（２）湿潤試験に従って測定した。６．１（２）乾燥試験では、試験布及び摩擦用白綿布は、予め標準状態に４時間以上放置する。摩擦試験機ＩＩ形により、摩擦子の質量を約２００ｇとして、試験片を試験片台上に、摩擦用白綿布を摩擦子の先端にそれぞれ取り付け、２Ｎの荷重で試験片１００ｍｍの間を、毎分３０回往復の速度で１００回往復摩擦する。６．２（２）湿潤試験では、摩擦用白綿布を水で濡らし約１００％湿潤状態にしたものを用いて、６．１（２）乾燥試験と同様に標準状態の試験片を摩擦した後、６０℃を越えない温度で乾燥する。摩擦用白綿布の着色判定は、ＪＩＳ Ｌ ０８０１の９．（染色堅牢度の判定）により、汚染用グレースケールを用いて級判定を行う。
【００３３】
２．実施例１及び比較例１，２（難燃加工剤）
下記表１に示す配合に従って、実施例１及び比較例１，２の各難燃加工剤を調製した。表１において、「ＣＲ−７３３Ｓ」は大八化学（株）製のテトラフェニル−ｍ−フェニレンジホスフェート、「ＴＰＰ」は大八化学（株）製のトリフェニルホスフェート、「ＴＣＰ」は大八化学（株）製のトリクレシルホスフェートである。また、上記調製に際し、乳化分散させるために使用した界面活性剤は、非イオン界面活性剤が第一工業製薬（株）製の「ノイゲン ＥＡ−８７」、アニオン界面活性剤が第一工業製薬（株）製の「ハイテノール ＮＦ−１３」である。
【００３４】
【表１】
３．実施例２〜５及び比較例３〜１２（染色同浴法）
上記実施例１及び比較例１，２の難燃加工剤を用いて、ポリエステル系合成繊維織物（レギュラーポリエステル１００％織物 トロピカル）に対し染色同浴法により難燃加工を施した。
【００３６】
詳細には、染色機としてＭｉｎｉ−Ｃｏｌｏｒ（テクサム技研製）を用い、下記表２に示す淡色染料と濃色染料の浴処方のそれぞれについて、浴比１：１０で、６０℃から昇温して、１３５℃×３０分間処理した。処理後、８０℃まで降温してから織物を取り出し、湯水洗×５分間の後、薬剤としてハイドロサルファイトナトリウム２ｇ／Ｌ、ソーダ灰１ｇ／Ｌ及びトライポールＴＫ（第一工業製薬（株）製）１ｇ／Ｌを用い、浴比１：３０で８０℃×１０分間還元洗浄を行い、更に、湯水洗×５分間の後、１８０℃×３０秒間ヒートセットを行った。なお、難燃加工剤の処理量は、表２に示すように、１０％ｏ．ｗ．ｆと２０％ｏ．ｗ．ｆ（ｏｎ ｔｈｅ ｗｅｉｇｈｔ ｏｆ
ｆｉｂｅｒ（繊維重量に対する比率））の２種類で行った。
【００３７】
【表２】
以上により難燃加工されたポリエステル系合成繊維織物について、淡色染料で染色した織物では、難燃剤の収着量と難燃性を測定し、濃色染料で染色した織物では、風合いを調べるとともに、難燃剤の収着量と難燃性と摩擦堅牢度を測定した。また、ブランク（比較例７，１２）として、難燃加工せずに染色した織物についても、同様に測定した。結果を下記表３に示す。なお、難燃剤の収着量は、加工前後の織物の重量変化（染料の増加分等は補正）から求めた。
【００３９】
【表３】
表３に示すように、ジホスフェート化合物単独である比較例１の難燃加工剤を用いた場合、ポリエステル繊維への収着量が少なく、耐久難燃性も不十分であった。また、ジホスフェート化合物とＴＣＰを併用した比較例２の難燃加工剤を用いた場合、収着量はある程度多くなるものの、低分子量で常温液体のＴＣＰを併用していることから摩擦堅牢度が悪化していた。
【００４１】
これに対し、ジホスフェート化合物とＴＰＰを併用した実施例１の難燃加工剤を用いた場合、ポリエステル繊維への収着量が多く、耐久難燃性に優れており、また風合いや摩擦堅牢度の悪化もなかった。
【００４２】
４．実施例６及び比較例１３〜１５（パッド・ドライ・サーモキュア法）
上記実施例１及び比較例１，２の難燃加工剤を用いて、ポリエステル系合成繊維織物（レギュラーポリエステル１００％織物 トロピカル）に対しパッド・ドライ・サーモキュア法により難燃加工を施した。
【００４３】
詳細には、難燃加工剤を水で１５％に希釈した液に、上記織物を浸漬した後、マングルで絞り率７０％に絞り、１１０℃×２分間乾燥し、１８０℃×２分間キュアした。その後、薬剤としてソーダ灰１ｇ／Ｌ及びトライポールＴＫ（第一工業製薬（株）製）１ｇ／Ｌを用い、浴比１：３０で８０℃×１０分間ソーピングを行い、更に、湯水洗×５分間の後、乾燥した。
【００４４】
これにより難燃加工されたポリエステル系合成繊維織物について、難燃剤の収着量と難燃性を測定した。また、ブランク（比較例１５）として、未処理の織物についても難燃性を測定した。結果を下記表４に示す。
【００４５】
【表４】
表４に示すように、ジホスフェート化合物とＴＰＰを併用した実施例１の難燃加工剤を用いた場合、ポリエステル繊維への収着量が多く、優れた耐久難燃性が得られた。
【００４７】
【発明の効果】
以上のように、本発明によれば、難燃剤として高分子量のジホスフェート化合物と低分子量で常温固体のトリフェニルホスフェートを併用したことにより、ポリエステル系合成繊維に対する難燃剤の収着量を向上することができ、優れた耐久難燃性を得ることができる。また、従来、低分子量のリン化合物を難燃剤として使用した場合、摩擦堅牢度を悪化させるという問題があったが、本発明であればその心配もない。更に、風合いの悪化も抑えることができる。
【００４８】
更に、本発明によれば、難燃剤としてノンハロゲンであるリン化合物を使用しているため、ポリエステル系合成繊維の燃焼時にハロゲン化ガスが発生することもなく、環境保護上にも有効である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a flame retardant capable of imparting excellent flame retardancy to a polyester synthetic fiber, a flame retardant processing method using the same, and a flame retardant polyester synthetic obtained by the method. It is about fibers.
[0002]
[Prior art]
Conventionally, as a flame retardant for imparting flame retardancy to polyester synthetic fibers by post-processing, those in which a halogen compound such as hexabromocyclododecane is dispersed or emulsified in water have been generally used. . However, polyester synthetic fibers treated with such a halogen-based flame retardant may generate harmful halogenated gases such as bromodioxin when burned, and there is an increasing demand for dehalogenation.
[0003]
Therefore, a flame retardant using a phosphorus compound such as an organic phosphoric acid ester is used, but a phosphorus compound which is conventionally generally used as a flame retardant has a low phosphorus content in the compound, Because of its low molecular weight, it decomposes and volatilizes below the flash point of the polyester-based synthetic fiber, making it difficult to impart sufficient flame retardancy. Therefore, conventionally, it is necessary to treat a large amount of a phosphorus compound, and due to the large amount of treatment, it causes a decrease in texture or causes bleeding of the dye with the dye over time on the fiber surface, resulting in a decrease in dyeing and friction fastness. There was a problem.
[0004]
In order to solve such a problem, it has been proposed to use a diphosphate compound having a large molecular weight as a flame retardant. For example, in Patent Document 1 below, resorcinol bis (diphenyl phosphate) is emulsified and dispersed in water in the presence of a surfactant to prepare a water emulsion, which is applied to a polyester synthetic fiber as a flame retardant. A flame-retardant processing method is disclosed.
[0005]
[Patent Document 1] Japanese Patent Application Laid-Open No. 2000-328445
[Problems to be solved by the invention]
The flame-retardant processing agent disclosed in Patent Document 1 uses a diphosphate compound alone as a flame retardant. However, the present inventor has studied and found that such a diphosphate compound alone is not practically required. It has proven difficult to obtain the durable flame retardancy as described. That is, since the above-mentioned diphosphate compound has a large molecular weight as a flame retardant, even if it alone adheres (adsorbs) to the fiber surface of the polyester-based synthetic fiber, sorption accompanied by a phenomenon of being absorbed inside the fiber occurs. Hateful. Since the flame retardant simply adhering to the fiber surface is dropped off by a solvent such as alkaline cleaning such as reduction cleaning or dry cleaning, it is not possible to obtain sufficient durable flame retardancy, especially durability against dry cleaning.
[0007]
The present invention has been made in view of the above points, and does not impair the feeling or friction fastness, and increases the sorption amount of a phosphorus-based flame retardant to impart flame resistance excellent in durability. An object of the present invention is to provide a flame-retardant agent which can be used, a flame-retardant processing method using the same, and a polyester-based synthetic fiber having excellent durability and flame retardancy.
[0008]
[Means for Solving the Problems]
The present inventors have conducted intensive studies, and as a result, it has been found that by using triphenyl phosphate at room temperature together with the above-mentioned diphosphate compound, the amount of the phosphorus-based flame retardant sorbed to the polyester-based synthetic fiber can be increased. The present inventors have found that a flame-retardant property against washing and dry cleaning, which cannot be obtained by the diphosphate compound alone formulation, can be obtained, and have completed the present invention.
[0009]
That is, according to the present invention, an aqueous dispersion or an aqueous emulsion containing triphenyl phosphate and a diphosphate compound composed of tetraphenyl-m-phenylenediphosphate and / or tetraphenyl-p-phenylenediphosphate. A flame retardant for polyester synthetic fibers is provided.
[0010]
According to the present invention, there is also provided a method for flame-retarding polyester-based synthetic fibers, characterized in that the above-mentioned flame-retardant agent is used for sorption to polyester-based synthetic fibers by a high-temperature exhaustion method or a pad thermo method. You.
[0011]
According to the present invention, there is further provided a flame-retardant polyester-based synthetic fiber flame-retarded by the above method.
[0012]
BEST MODE FOR CARRYING OUT THE INVENTION
In the flame retardant of the present invention, the diphosphate compound used as a flame retardant includes tetraphenyl-m-phenylenediphosphate represented by the following formula (1) and tetraphenyl-m-phenylenediphosphate represented by the following formula (2). p-phenylenediphosphate, both of which may be used alone or in combination.
[0013]
Embedded image
In the flame retardant of the present invention, triphenyl phosphate (TPP) used as a flame retardant together with the diphosphate compound is represented by the following formula (3).
[0015]
Embedded image
The diphosphate compound has a high phosphorus content in the compound and a high molecular weight, and thus exhibits an excellent flame-retardant effect, but sorbs to the polyester-based synthetic fiber due to the large molecular weight. There is a disadvantage that it is difficult to do. Therefore, by using TPP which is a solid at normal temperature and has an effect of improving sorption, the amount of phosphorus compounds sorbed to the polyester-based synthetic fiber can be increased, and excellent durable flame retardancy can be imparted. Further, although TPP has a low molecular weight, it is hard to migrate since it is a solid at normal temperature, and thus it is difficult for the dye to bleed out to the fiber surface with an accompanying dye, and therefore, it is possible to suppress a decrease in color fastness. Note that sorption refers to a phenomenon involving absorption into the fiber when the phosphorus compound as a flame retardant is adsorbed on the fiber surface, but the entire structure of the phosphorus compound does not necessarily have to enter the fiber. This includes the case where only a part of the structure, for example, only the phenyl group at the end is penetrated into the fiber.
[0017]
The ratio of the diphosphate compound to TPP is preferably such that the diphosphate compound is 40 to 80% by weight in the flame retardant component and the TPP is 20 to 60% by weight in the flame retardant component.
[0018]
The flame retardant of the present invention is a water dispersion or a water emulsion obtained by dispersing or emulsifying the above diphosphate compound and TPP in water in the presence of a surfactant. As the surfactant at that time, one or both of a nonionic surfactant and an anionic surfactant are used.
[0019]
Specific examples of the nonionic surfactant include polyoxyalkylene alkylphenyl ether, polyoxyalkylene alkyl ether, polyoxyalkylene alkyl ester, polyhydric alcohol fatty acid ester alkylene oxide adduct, higher alkylamine alkylene oxide adduct, and fatty acid amide. Examples include alkylene oxide adducts, alkyl glycosides, and sucrose fatty acid esters. Preferably, polyoxyethylene distyrenated phenyl ether and polyoxyethylene tristyrenated phenyl ether are used.
[0020]
Specific examples of the anionic surfactants include higher alcohol sulfates, higher alkyl ether sulfates, alkyl sulfate salts such as sulfated fatty acid esters, alkyl benzene sulfonates, and alkyl sulfonate salts such as alkyl naphthalene sulfonates; Further, alkyl phosphate salts such as a higher alcohol phosphate ester salt and a higher alcohol alkylene oxide adduct phosphate ester salt are exemplified. Further, alkylaryl sulfonate salts, polyoxyalkylene alkyl ether sulfate salts, polyoxyalkylene alkyl ester phosphate salts, polyoxyalkylene alkyl ether carboxylate salts, polycarboxylate salts, funnel oil, petroleum sulfonates, alkyl diphenyl ether sulfonate salts and the like. Can be Preferred are polyoxyethylene distyrenated or tristyrenated phenyl ether sulfates.
[0021]
The use amount of such a surfactant is not particularly limited, but is usually used in the range of 10 to 30% by weight based on the phosphorus compound as a flame retardant component.
[0022]
In the flame retardant of the present invention, the content of the phosphorus compound as a flame retardant component is usually in the range of 30 to 50% by weight. The flame retardant of the present invention may contain an organic solvent such as methyl alcohol, ethyl alcohol, toluene, ethylene glycol and butyl cellosolve in order to stabilize the dispersed or emulsified state. Also, various additives such as an ultraviolet absorber and an antioxidant can be blended.
[0023]
The flame retardant of the present invention is used for imparting flame retardancy to polyester synthetic fibers by post-processing. Examples of such post-processing include a high-temperature exhaustion method and a pad thermo method. Is mentioned.
[0024]
In the high-temperature exhaustion method, a polyester synthetic fiber is immersed in a treatment bath to which a flame retardant is added, and treated at a high temperature (usually 80 ° C. or higher, preferably 110 to 150 ° C.) for a predetermined time (for example, 2 to 60 minutes). By doing so, the flame retardant is sorbed on the fiber. Preferably, it is a dyeing and bathing method in which the flame retardant is simultaneously sorbed to the fiber at the same time as the dye. That is, it is efficient and preferable to add a flame retardant to the dyeing bath, immerse the polyester synthetic fiber in the dyeing bath, and perform the exhaustion treatment at a high temperature.
[0025]
In the pad thermo method, polyester synthetic fibers are immersed in a liquid containing a flame retardant, squeezed with a mangle or the like to a predetermined amount, and heat-treated by steaming such as dry heat treatment or superheated steam treatment. By doing so, the flame retardant is sorbed on the fibers. The heat treatment temperature is usually in the range of 110 to 210 ° C. Preferably, after immersion, it is processed by a pad dry thermocure method of squeezing with a mangle, drying and heat setting.
[0026]
The polyester synthetic fiber to be processed is obtained by copolymerizing or blending a polyester such as polyethylene terephthalate or polybutylene terephthalate, or a third component such as isophthalic acid, isophthalic acid sulfonate, adipic acid or polyethylene glycol. It is a fiber made of a polyester obtained, and may be a long fiber or a short fiber. Further, the form of the fiber is not particularly limited as long as it is a fiber product such as a yarn, a woven or knitted fabric, a nonwoven fabric, or a rope. Further, other synthetic fibers, natural fibers, and semi-synthetic fibers may be mixed with the polyester-based synthetic fibers as long as the effects of the present invention are not impaired.
[0027]
【Example】
Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. In the examples, "parts" indicates parts by weight, and "%" indicates% by weight.
[0028]
1. Evaluation method (1) Product stability The flame retardant was allowed to stand at room temperature for 30 days, and the state of the aqueous dispersion or emulsion after the standing was evaluated. The evaluation was `` ○ '' when water separation or separation did not occur and the state immediately after preparation was maintained, and `` × '' when water separation or separation occurred and the original dispersion or emulsified state could not be restored even after shaking. "△" indicates that the original dispersion or emulsified state was restored by shaking with slight water separation or separation.
[0029]
(2) Flame retardancy The JIS L 1091 A-1 method (micro burner method) and JIS L 1091 D method are used for the woven fabric that has undergone flame-retardant processing, and the woven fabric that has been processed and the one that has been washed with water or dry-cleaned under the following conditions. Flame retardancy was measured by the method (coil method). In the micro burner method, after 1 minute of heating and 3 seconds after the flame application, the residual flame is 3 seconds or less, the residual dust is 5 seconds or less, and the carbonization area is 30 cm 2 or less. Indicates “×”. In the coil method, a sample having three or more times of flame contact was indicated by “○”, and a sample having two or less times of contact was indicated by “×”.
[0030]
(Washing) According to JIS K 3371, a weak alkaline type 1 detergent was used at a ratio of 1 g / L, a bath ratio of 1:40, and water washing at 60 ° C. ± 2 ° C. for 15 minutes, and then at 40 ° C. ± 2 ° C. Rinsing for 5 minutes was performed three times, centrifugal dehydration was performed for 2 minutes, and thereafter, the process of drying with hot air at 60 ° C. ± 5 ° C. was performed once, and this was performed five times.
[0031]
(Dry Cleaning) 30 ° C. ± 2 ° C. using 12.6 mL of tetrachloroethylene and 0.265 g of charge soap (nonionic surfactant / anionic surfactant / water = 10/10/1 (weight ratio)) per 1 g of sample. Was performed once for 15 minutes, and this was performed five times.
[0032]
(3) Dye fastness The woven fabric flame-retarded with a dark dye was measured according to JIS L 0849 6.1 (2) dry test or 6.2 (2) wet test. 6.1 (2) In the drying test, the test cloth and the white cotton cloth for friction are left in a standard state for 4 hours or more in advance. With a friction tester type II, the mass of the friction element was set to about 200 g, the test piece was mounted on the test piece stand, and a white cotton cloth for friction was attached to the tip of the friction element, respectively. Rub 100 reciprocations at a speed of 30 reciprocations per minute. 6.2 (2) In the wet test, after rubbing the test piece in the standard condition in the same manner as in the 6.1 (2) dry test, using a white cotton cloth for friction rubbed with water to make it about 100% wet. At a temperature not exceeding 60 ° C. The coloring of the white cotton cloth for friction is determined according to JIS L 0801, 9. (Determination of the color fastness), the grade is determined using the gray scale for staining.
[0033]
2. Example 1 and Comparative Examples 1 and 2 (flame retardant)
According to the composition shown in Table 1 below, the respective flame retardants of Example 1 and Comparative Examples 1 and 2 were prepared. In Table 1, "CR-733S" is tetraphenyl-m-phenylenediphosphate manufactured by Daihachi Chemical Co., Ltd., "TPP" is triphenyl phosphate manufactured by Daihachi Chemical Co., Ltd., and "TCP" is Daihachi Chemical. It is tricresyl phosphate manufactured by Co., Ltd. In the above preparation, the surfactant used for emulsification / dispersion was “Neugen EA-87” manufactured by Daiichi Kogyo Seiyaku Co., Ltd., and the anionic surfactant was Daiichi Kogyo Seiyaku ( "HYTENOL NF-13".
[0034]
[Table 1]
3. Examples 2 to 5 and Comparative Examples 3 to 12 (Dyeing same bath method)
Using the flame retardant of Example 1 and Comparative Examples 1 and 2, a polyester synthetic fiber fabric (100% regular polyester fabric, tropical) was subjected to flame retardancy by the same dyeing and bathing method.
[0036]
Specifically, using Mini-Color (manufactured by Texam Giken) as a dyeing machine, the bath formulation of the light-colored dye and the dark-colored dye shown in Table 2 below was heated from 60 ° C. at a bath ratio of 1:10. And treated at 135 ° C. for 30 minutes. After the treatment, the temperature was lowered to 80 ° C., the fabric was taken out, washed with hot and cold water × 5 minutes, and then sodium hydrosulfite 2 g / L, soda ash 1 g / L and Tripol TK (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) ) Using 1 g / L, reduction washing was carried out at a bath ratio of 1:30 at 80 ° C. × 10 minutes, and after hot water washing × 5 minutes, heat set was performed at 180 ° C. × 30 seconds. In addition, the processing amount of the flame retardant was 10% o. w. f and 20% o. w. f (on the weight of
fiber (ratio to fiber weight)).
[0037]
[Table 2]
For the polyester synthetic fiber woven fabric that has been flame-retarded as described above, in the fabric dyed with the light-colored dye, the sorption amount and flame retardancy of the flame retardant are measured, and in the fabric dyed with the dark-colored dye, the texture is examined. The sorbed amount of the flame retardant, flame retardancy and friction fastness were measured. In addition, as a blank (Comparative Examples 7 and 12), the same measurement was performed on a woven fabric dyed without flame-retardant processing. The results are shown in Table 3 below. The sorption amount of the flame retardant was determined from the weight change of the woven fabric before and after processing (the increase in the dye was corrected).
[0039]
[Table 3]
As shown in Table 3, when the flame retardant of Comparative Example 1, which was a diphosphate compound alone, was used, the amount of sorption on the polyester fiber was small, and the durability and flame retardancy were insufficient. Further, when the flame retardant of Comparative Example 2 in which the diphosphate compound and TCP were used in combination was used, although the sorption amount was increased to some extent, the low-molecular weight and room temperature liquid TCP was used in combination, so that the friction fastness was low. Was getting worse.
[0041]
On the other hand, when the flame-retardant processing agent of Example 1 in which the diphosphate compound and TPP were used in combination was used, the amount of sorption to the polyester fiber was large, the durability was excellent in flame retardancy, and the texture and friction fastness were high. There was no deterioration.
[0042]
4. Example 6 and Comparative Examples 13 to 15 (Pad dry thermocure method)
Using the flame retardant agents of Example 1 and Comparative Examples 1 and 2, a polyester synthetic fiber woven fabric (100% regular polyester woven fabric, tropical) was subjected to a flame retardant treatment by a pad dry thermocure method.
[0043]
Specifically, after immersing the woven fabric in a solution obtained by diluting a flame retardant to 15% with water, the fabric was squeezed with a mangle to a squeezing ratio of 70%, dried at 110 ° C for 2 minutes, and cured at 180 ° C for 2 minutes. . Thereafter, using 1 g / L of soda ash and 1 g / L of Tripol TK (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) as agents, soaping was performed at 80 ° C. for 10 minutes at a bath ratio of 1:30, and further, washing with hot and cold water × 5 After a minute, it was dried.
[0044]
With respect to the polyester-based synthetic fiber woven fabric which was thus subjected to the flame-retardant processing, the sorbed amount of the flame retardant and the flame retardancy were measured. Further, as a blank (Comparative Example 15), the flame retardancy was measured for an untreated woven fabric. The results are shown in Table 4 below.
[0045]
[Table 4]
As shown in Table 4, when the flame retardant of Example 1 in which the diphosphate compound and TPP were used in combination was used, the amount of sorption to the polyester fiber was large, and excellent durability flame retardancy was obtained.
[0047]
【The invention's effect】
As described above, according to the present invention, the combined use of a high-molecular-weight diphosphate compound and low-molecular-weight, normal-temperature solid triphenyl phosphate as the flame retardant improves the sorption amount of the flame retardant to the polyester synthetic fiber. And excellent durable flame retardancy can be obtained. Further, conventionally, when a low molecular weight phosphorus compound was used as a flame retardant, there was a problem that friction fastness was deteriorated. However, according to the present invention, there is no problem. Further, deterioration of the texture can be suppressed.
[0048]
Furthermore, according to the present invention, since a non-halogen phosphorus compound is used as the flame retardant, no halogenated gas is generated when the polyester-based synthetic fiber is burned, which is effective for environmental protection.
Claims (5)
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| JP2003011640A JP2004225176A (en) | 2003-01-20 | 2003-01-20 | Flame-retardant finishing agent for polyester-based synthetic fiber, flame-retardant processing method using the same and flame-retardant polyester-based synthetic fiber |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007086594A1 (en) * | 2006-01-26 | 2007-08-02 | Komatsu Seiren Co., Ltd. | Flameproofing agent for polyester textile and flameproofing method |
| WO2008013176A1 (en) * | 2006-07-25 | 2008-01-31 | Nippon Kayaku Kabushiki Kaisha | Non-halogen dispersion for fireproofing, fireproofing method using the same, and fiber fireproofed with the same |
| WO2009122980A1 (en) * | 2008-03-31 | 2009-10-08 | 日華化学株式会社 | Flameproofing agent for polyester fiber, flame-retardant polyester fiber using the same, and method for producing the flame-retardant polyester fiber |
| EP2133461A1 (en) | 2008-06-12 | 2009-12-16 | Huntsman Textile Effects (Germany) GmbH | Compound for treating fibrous material, in particular by the method of extraction |
| CN101981157A (en) * | 2008-03-28 | 2011-02-23 | 日本化药株式会社 | Aqueous dispersion of organic phosphorus compound and flameproofing method using the same |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007086594A1 (en) * | 2006-01-26 | 2007-08-02 | Komatsu Seiren Co., Ltd. | Flameproofing agent for polyester textile and flameproofing method |
| JP2007197867A (en) * | 2006-01-26 | 2007-08-09 | Komatsu Seiren Co Ltd | Flame-retardant finishing agent and flame-retardant finishing method for polyester fiber product |
| WO2008013176A1 (en) * | 2006-07-25 | 2008-01-31 | Nippon Kayaku Kabushiki Kaisha | Non-halogen dispersion for fireproofing, fireproofing method using the same, and fiber fireproofed with the same |
| TWI424108B (en) * | 2006-07-25 | 2014-01-21 | Nippon Kayaku Kk | Non-halogenated dispersions for flame retarding, flame retarding modification method using the dispersions and flame retarding modified fibers by the method |
| CN101981157A (en) * | 2008-03-28 | 2011-02-23 | 日本化药株式会社 | Aqueous dispersion of organic phosphorus compound and flameproofing method using the same |
| CN101981157B (en) * | 2008-03-28 | 2013-08-21 | 日本化药株式会社 | Aqueous dispersion of organic phosphorus compound and flameproofing method using the same |
| WO2009122980A1 (en) * | 2008-03-31 | 2009-10-08 | 日華化学株式会社 | Flameproofing agent for polyester fiber, flame-retardant polyester fiber using the same, and method for producing the flame-retardant polyester fiber |
| JP2009242969A (en) * | 2008-03-31 | 2009-10-22 | Nicca Chemical Co Ltd | Flame-retardant finishing agent for polyester-based fiber, flame-retardant polyester-based fiber using the same, and method for producing the same |
| US8039534B2 (en) | 2008-03-31 | 2011-10-18 | Nicca Chemical Co., Ltd. | Flame-retarder agent for polyester-based fiber, flame retardant polyester-based fiber using the same and method for producing the same |
| EP2133461A1 (en) | 2008-06-12 | 2009-12-16 | Huntsman Textile Effects (Germany) GmbH | Compound for treating fibrous material, in particular by the method of extraction |
| US8303835B2 (en) | 2008-06-12 | 2012-11-06 | Huntsman Textile Effects (Germany) Gmbh | Composition for treatment of fiber materials by exhaust method in particular |
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