JP6110152B2 - 繊維用難燃加工薬剤、難燃性繊維の製造方法及び難燃性繊維 - Google Patents
繊維用難燃加工薬剤、難燃性繊維の製造方法及び難燃性繊維 Download PDFInfo
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- JP6110152B2 JP6110152B2 JP2013023084A JP2013023084A JP6110152B2 JP 6110152 B2 JP6110152 B2 JP 6110152B2 JP 2013023084 A JP2013023084 A JP 2013023084A JP 2013023084 A JP2013023084 A JP 2013023084A JP 6110152 B2 JP6110152 B2 JP 6110152B2
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- phosphate
- fiber
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- retardant
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- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical class C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- ASLWPAWFJZFCKF-UHFFFAOYSA-N tris(1,3-dichloropropan-2-yl) phosphate Chemical compound ClCC(CCl)OP(=O)(OC(CCl)CCl)OC(CCl)CCl ASLWPAWFJZFCKF-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- GXZLXDRFEDHOAU-UHFFFAOYSA-N tris(4-phenylphenyl) phosphate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OP(OC=1C=CC(=CC=1)C=1C=CC=CC=1)(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 GXZLXDRFEDHOAU-UHFFFAOYSA-N 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
前記トリクレジルホスフェート(A)と前記有機臭素化合物(B)との重量比(A/B)は、95/5〜5/95であることが好ましい。
また、前記トリクレジルホスフェート(A)及び前記有機臭素化合物(B)は、水中に乳化又は分散された状態にあることが好ましい。
本発明の難燃性繊維において、前記トリクレジルホスフェート(A)の融点は65〜80℃であることが好ましい。また、前記トリクレジルホスフェート(A)と前記臭有機臭素化合物(B)との重量比(A/B)は、95/5〜5/95であることが好ましい。
本発明の繊維用難燃加工薬剤は、繊維材料に難燃性を付与するために用いられる組成物であって、トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A)(以下、単にトリクレジルホスフェート(A)ということがある。)、臭素含有量が50重量%以上であり、融点が80℃以上である有機臭素化合物(B)(以下、単に有機臭素化合物(B)ということがある。)、界面活性剤及び水を含有するものである。以下に、詳細に説明する。
これらの中でも、吸尽性が高く、難燃性に優れる点から、トリス(2,3−ジブロモプロピル)イソシアヌレート、トリス(トリブロモネオペンチル)ホスフェート、ビス(3,5−ジブロモ−4−ジブロモプロピルオキシフェニル)スルホン、テトラブロモシクロオクタン、エチレンビステトラブロモフタルイミド、ヘキサブロモベンゼン、ヘキサブロモシクロドデカン、臭素化シクロアルカンが好ましく、トリス(2,3−ジブロモプロピル)イソシアヌレートがさらに好ましい。
ここで、結晶領域とは、たとえば、合成繊維等の製造工程中で延伸等の物理的処理をした場合に形成されるような、繊維を構成する分子鎖が相対的に規則正しく配向した領域を意味し、非結晶領域とは、上記の説明とは逆で、繊維を構成する分子鎖が相対的に規則正しくなく、ランダムに配向した領域を意味することとする。
本発明の難燃性繊維の製造方法は、上記難燃加工薬剤を繊維材料に処理する工程(処理工程)を含む。
付着は、パディング法、スプレー法、コーティング法等によって行うことができる。また、熱処理は、乾熱処理及び湿熱処理のいずれでもよい。例えば、スプレー−ドライ−キュア方式、パッド−ドライ−スチーム方式、パッド−スチーム方式、パッド−ドライ−キュア方式等が挙げられる。
染料の含有量は、繊維材料に対して、0.01〜50重量%が好ましく、0.1〜20重量%がより好ましく、0.2〜10重量%がさらに好ましい。
本発明の難燃性繊維は、繊維材料に対して、トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A)及び臭素含有量が50重量%以上であり、融点が80℃以上である有機臭素化合物(B)が付着してなるものである。本発明の難燃性繊維の製造方法で得ることができる。繊維材料、トリクレジルホスフェート(A)、有機臭素化合物(B)については、前述したものと同じである。
〔融点〕
トリクレジルホスフェート(A)、有機臭素化合物(B)について、示差走査熱量計DSC220U(セイコー電子工業株式会社製)を用い、窒素雰囲気下、不揮発分約5mgを昇温速度10℃/分で0℃から500℃まで昇温し、現れる吸熱ピークの温度を測定した。
1)コイル法
JIS−L−1091のD法に従い、接炎回数を測定した。タテ、ヨコ各5回測定し、その平均値を算出した。平均値は、3以上が好ましく、4以上がさらに好ましい。
2)45°ミクロバーナー法
JIS−L−1091のA−1法に従い、残炎時間を測定した。タテ、ヨコ各5回測定し、その平均値を算出した。平均値は、3秒以下が好ましく、1秒以下がさらに好ましい。
スペック防止性、缶体汚染性評価については、水が投入されたミニカラー専用染色ポット内に、調製した難燃加工薬剤を1g/Lの濃度になるよう投入し、続いてKayalon Polyester Black RV−SF300(4重量%owf、日本化薬株式会社製)を30〜35℃の水に溶きながら投入し、酢酸/酢酸ナトリウム緩衝液でpH4.5に調整して、染色浴を調製した。その後、編立て油剤であるブリアンC−1820(2g/L、松本油脂製薬株式会社製)を浴内に投入した。その際の想定浴比としては、1:20とした。
次に、染色浴のみをミニカラーにて処理した。処理条件としては、1分間に2℃の割合で135℃まで加温し、135℃を60分間保った。その後、冷却し60℃になったところで、精練染色液をろ紙を用いてろ過を行った。スペック防止性評価はろ紙を自然乾燥させた状態で、以下の基準で行った。また、缶体汚染性は、ミニカラー専用染色ポットの汚れ度合いを以下の基準で行った。
○:ろ紙に色がほとんど着かない。
×:ろ紙全面にスペックが存在し、ろ紙に激しい着色がみられる。
△:ろ紙全面にスペックが存在し、ろ紙に着色がみられる(○と×の中間レベル)。
・缶体汚染性評価基準
○:ミニカラー専用染色ポット内に汚れがほとんどみられない。
×:ミニカラー専用染色ポット内全体に汚れがみられる。
△:ミニカラー専用染色ポット内の一部に汚れがみられる。
JIS−L−0842により、得られた難燃性ポリエステル繊維をカーボンアーク燈光で100時間照射し、級数で評価した。級数が大きいほど耐光堅牢性が良い。
難燃性ポリエステル繊維を、JIS−L−0849にて摩擦試験機II型により摩擦堅牢度試験を行い、級数で評価した。級数が大きいほどブリード性がよい。
<トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A1)の製造>
2000mL4つ口フラスコに、p−クレゾール(和光純薬株式会社製、純度99.70重量%、フェノール0.10重量%、o−クレゾール0.20重量%含有)716gと塩化アルミニウム16gを入れ、80℃でオキシ三塩化リン335gを2時間かけてゆっくり滴下し、発生する塩化水素は除去した。滴下終了後、120℃で3時間熟成した。反応物を90℃に冷却し、苛性ソーダ5重量%液を500g投入し、90℃で1時間攪拌した。水相は除去し、反応物を冷水に投入し、1時間洗浄し、脱水し、さらに水で1時間洗浄した。脱水、乾燥させ、トリ−p−クレジルホスフェートの純度が99.1重量%で白色固体である、トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A1)が770g得られ、融点は77℃であった。
<トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A2)の製造>
2000mL4つ口フラスコに、p−クレゾール(和光純薬株式会社製、純度99.70重量%、フェノール0.10重量%、o−クレゾール0.20重量%含有)710g、m−クレゾール(和光純薬株式会社製、純度99.9重量%)6gと塩化アルミニウム16gを入れ、80℃でオキシ三塩化リン335gを2時間かけてゆっくり滴下し、発生する塩化水素は除去した。滴下終了後、120℃で3時間熟成した。反応物を90℃に冷却し、苛性ソーダ5重量%液を500g投入し、90℃で1時間攪拌した。水相は除去し、反応物を冷水に投入し、1時間洗浄し、脱水し、さらに水で1時間洗浄した。脱水、乾燥させ、トリ−p−クレジルホスフェートの純度が96.5重量%で白色固体である、トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A2)が773g得られ、融点は75℃であった。
表1にそれぞれ示す配合成分(重量部)をデスパ型攪拌機に加え、25℃で十分に攪拌及び分散させた。その後、スターミルZRS(アシザワファインテック株式会社製)を用いて、得られたスラリー液を25℃で6時間微粒子化し、難燃加工薬剤をそれぞれ調製した。調製した難燃加工薬剤を用いて、スペック防止性、缶体汚染性を評価した。
次に、調製した難燃加工薬剤を用いて、下記の難燃加工1、難燃加工2の条件でそれぞれ難燃加工を行い、難燃性ポリエステル繊維を得た。得られた難燃性ポリエステル繊維(表では「加工上り」と示す)について、ブリード性、難燃性を評価した。また、得られた難燃性ポリエステル繊維について、JIS−L−1091の方法により水洗い洗濯を5回行った後(表では「洗濯5回後」と示す)、及びJIS−L−1018の方法によりドライクリーニングを5回行った後(表では「ドライクリーニング5回後」と示す)、難燃性を評価した。これらの結果を表1に示す。
ミニカラー染色機(テクサム技研社製)のミニカラー専用染色ポット内に、水、染色同浴精練剤であるマーポンISD−1(松本油脂製薬株式会社製)2g/L、均染剤であるマーポマーベリンB−70(松本油脂製薬株式会社製)及び難燃加工薬剤組成物10重量%owfを投入し、続いてKayalon Polyester Black RV−SF300(2重量%owf、日本化薬株式会社製)を30〜35℃の水に溶きながら投入し、その後、酢酸/酢酸ナトリウム緩衝液でpH4.5に調整して、染色浴を調製した。
次に、ポリエステルトロピカル生機を調製した染色浴に投入し、ミニカラーにて処理した。その際の浴比としては、1:20であった。処理条件としては、1分間に2℃の割合で135℃まで加温し、135℃を30分間保った。その後、冷却し70℃になったところで、染色浴を廃棄し、5分間水洗いを行った。
次に、ソーピング剤であるマーポマーベリンS−1520(松本油脂製薬株式会社製)1g/L、ハイドロサルファイト2g/L、苛性ソーダ2g/Lを含む浴で、浴比1:20、温度80℃の条件で、15分間ソーピング処理を行い、水洗し、160℃で1分乾燥し、難燃性ポリエステル繊維を得た。
ミニカラー染色機(テクサム技研社製)のミニカラー専用染色ポット内に、水、染色同浴精練剤であるマーポンISD−1(松本油脂製薬株式会社製)2g/L、均染剤であるマーポマーベリンB−70(松本油脂製薬株式会社製)を投入し、続いてKayalon Polyester Black RV−SF300(2重量%owf、日本化薬株式会社社製)を30〜35℃の水に溶きながら投入し、その後、酢酸/酢酸ナトリウム緩衝液でpH4.5に調整して、染色浴を調製した。
次に、ポリエステルトロピカル生機を調製した染色浴に投入し、ミニカラーにて処理した。その際の浴比としては、1:20であった。処理条件としては、1分間に2℃の割合で135℃まで加温し、135℃を30分間保った。その後、冷却し70℃になったところで、染色浴を廃棄し、5分間水洗いを行った。
次に、ソーピング剤であるマーポマーベリンS−1520(松本油脂製薬株式会社製)1g/L、ハイドロサルファイト2g/L、苛性ソーダ2g/Lを含む浴で、浴比1:20、温度80℃の条件で、15分間ソーピング処理を行い、水洗し、120℃で4分間乾燥し、ポリエステル染色布を得た。このポリエステルトロピカル染色布を、難燃加工薬剤組成物5重量%含む処理液に浸漬し、マングルで絞り(絞り率90%)、乾燥を110℃で3分間行い、キュアリングを160℃で1分間行い、難燃性ポリエステル繊維を得た。
表1、2にそれぞれ示す配合成分を変更する以外は、実施例1と同様にして評価を行った。その結果を表1、2に示す。なお、表1、2に示したPOE(13)スチレン化フェノールサルフェートNa塩とは、ポリオキシエチレンスチレン化フェノールサルフェートNa塩であって、そのオキシエチレン基の繰返し数の平均が13であるという意味である。また、スチレン化フェノールのスチレン化度は重量比でモノ:ジ:トリ=15:50:35である。POE(7)スチレン化クレゾールサルフェートNa塩のスチレン化クレゾールのスチレン化度は重量比でモノ:ジ:トリ=10:80:10であり、クレゾールは、m−クレゾール:p−クレゾール=50〜60:40〜50(重量比)のクレゾールを使用した。PEG(600)とは、ポリエチレングリコールの平均分子量が約600であるという意味である。有機臭素化合物(B)について、表1のトリス(2,3−ジブロモプロピル)イソシアヌレートはFCP−660CN(臭素含有量66重量%、融点115℃)(鈴祐化学株式会社製)を使用し、ヘキサブロモシクロドデカンはSAYTEX HP−900(臭素含有量74重量%、融点180℃)(アルベマール日本株式会社製)を使用し、ヘキサブロモベンゼンはFR−B(臭素含有量87重量%、融点327℃)(日宝化学株式会社製)を使用し、エチレンビステトラブロモフタルイミドはSAYTEX BT−93(臭素含有量67重量%、融点456℃)(アルベマール日本株式会社製)を使用し、ビス(3,5−ジブロモ−4−ジブロモプロピルオキシフェニル)スルホンはFCP−65(臭素含有量65重量%、融点115℃)(鈴祐化学株式会社製)を使用した。トリフェニルホスフィンオキサイドは、TPPO(ケイアイ化成株式会社製)を使用した。また、表2の異性体混合物のトリクレジルホスフェート(TCP)は、m−クレゾール:p−クレゾール=50〜60:40〜50(重量比)のクレゾールの異性体混合物から得られる、凝固点が−35℃のトリクレジルホスフェートの異性体混合物を示す。表2の難燃成分C〜Mの詳細は、表3に示す通りである。
Claims (9)
- トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A)、臭素含有量が50重量%以上であり、融点が100℃以上である有機臭素化合物(B)、界面活性剤及び水を含有し、
前記トリクレジルホスフェート(A)全体に占めるトリ−p−クレジルホスフェートの重量割合が90重量%以上である、繊維用難燃加工薬剤。 - 前記トリクレジルホスフェート(A)の融点が、65〜80℃である、請求項1に記載の難燃加工薬剤。
- 前記トリクレジルホスフェート(A)と前記有機臭素化合物(B)との重量比(A/B)が、95/5〜5/95である、請求項1又は2に記載の難燃加工薬剤。
- 前記界面活性剤が、ポリオキシアルキレン多環アリールエーテルサルフェート塩及びポリオキシアルキレン多環アリールエーテルから選ばれる少なくとも1種を含む、請求項1〜3のいずれかに記載の難燃加工薬剤。
- 前記トリクレジルホスフェート(A)及び前記有機臭素化合物(B)が水中に乳化又は分散された状態にある、請求項1〜4のいずれかに記載の難燃加工薬剤。
- 請求項1〜5のいずれかに記載の難燃加工薬剤を繊維材料に処理する工程を含む、難燃性繊維の製造方法。
- 繊維材料に対して、トリ−p−クレジルホスフェートを主成分とするトリクレジルホスフェート(A)及び臭素含有量が50重量%以上であり、融点が100℃以上である有機臭素化合物(B)が付着してなり、
前記トリクレジルホスフェート(A)全体に占めるトリ−p−クレジルホスフェートの重量割合が90重量%以上である、難燃性繊維。 - 前記トリクレジルホスフェート(A)の融点が、65〜80℃である、請求項7に記載の難燃性繊維。
- 前記トリクレジルホスフェート(A)と前記有機臭素化合物(B)との重量比(A/B)が、95/5〜5/95である、請求項7又は8に記載の難燃性繊維。
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