JP6454783B2 - 無黄変軟質ポリウレタンフォーム、衣料材料、ブラジャーのパッド、および、ブラジャーのカップ - Google Patents
無黄変軟質ポリウレタンフォーム、衣料材料、ブラジャーのパッド、および、ブラジャーのカップ Download PDFInfo
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- JP6454783B2 JP6454783B2 JP2017517924A JP2017517924A JP6454783B2 JP 6454783 B2 JP6454783 B2 JP 6454783B2 JP 2017517924 A JP2017517924 A JP 2017517924A JP 2017517924 A JP2017517924 A JP 2017517924A JP 6454783 B2 JP6454783 B2 JP 6454783B2
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- Prior art keywords
- mass
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- uretdione
- pentamethylene diisocyanate
- Prior art date
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
Description
また、脂肪族ポリイソシアネートの三量体誘導体の塩素濃度は、脂肪族ポリイソシアネートの三量体誘導体の総量に対して、例えば、10質量ppm以上、好ましくは、50質量ppm以上であり、例えば、60質量ppm以上、例えば、100ppm以下である。
1.測定方法
<イソシアネート基濃度(単位:質量%)、イソシアネート基の転化率(単位:質量%)>
電位差滴定装置(京都電子工業社製、型番:AT−510)を用いて、JIS K−1603−1(2007年)に準拠したトルエン/ジブチルアミン・塩酸法によりイソシアネート基濃度(イソシアネート基含有率)を測定し、以下の式により、測定試料のイソシアネート基の転化率を算出した。
<イソシアネートモノマー濃度(単位:質量%)>
国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートまたは市販のヘキサメチレンジイソシアネートを標準物質として用い、ジベンジルアミンによりラベル化させ、以下のHPLC測定条件下で得られたクロマトグラムの面積値から作成した検量線により、未反応のペンタメチレンジイソシアネートモノマーまたはヘキサメチレンジイソシアネートモノマーの濃度を算出した。
ポンプ LC−20AT
デガッサ DGU−20A3
オートサンプラ SIL−20A
カラム恒温槽 COT−20A
検出器 SPD−20A
カラム;SHISEIDO SILICA SG−120
カラム温度;40℃
溶離液;n−ヘキサン/メタノール/1,2−ジクロロエタン=90/5/5(体積比)
流量;0.2mL/min
検出方法;UV 225nm
<粘度(単位:mPa・s)>
東機産業社製のE型粘度計TV−30(ローター角度:1°34’、ローター半径:24cm)を用いて、JIS K5600−2−3(2014年)のコーン・プレート粘度計法に準拠して、25℃で測定試料の粘度を測定した。測定時のコーンプレートの回転数は、粘度が高くなるのに合わせて、100rpmから2.5rpmまでの間で順次変更した。
以下のGPC測定条件において得られたクロマトグラムにより、全ピーク面積に対する、ポリエチレンオキシド換算分子量280〜380の間をピークトップとするピークの面積の割合を、ペンタメチレンジイソシアネートのウレトジオン誘導体に対する、ペンタメチレンジイソシアネートのウレトジオン2分子体の濃度とした。
カラム;G1000HXL、G2000HXLおよびG3000HXL(以上、東ソー製、商品名)を直列に連結
カラム温度;40℃
溶離液;テトラヒドロフラン
流量;0.8mL/min
検出器;示差屈折率検出器
標準物質;ポリエチレンオキシド(東ソー社製、商品名:TSK標準ポリエチレンオキシド)
<1H−NMRによるアロファネート基とイソシアヌレート基とのモル比率の算出>
下記の装置および条件にて1H−NMRを測定し、脂肪族ポリイソシアネートの三量体誘導体における、イソシアヌレート基1モルに対するアロファネート基の含有割合(アロファネート基/イソシアヌレート基のモル比率)を以下の式により算出した。なお、化学シフトppmの基準として、D6−DMSO溶媒中のテトラメチルシラン(0ppm)を用いた。
装置; JNM−AL400(JEOL製)
条件; 測定周波数:400MHz、溶媒:D6−DMSO、溶質濃度:5質量%
アロファネート基(アロファネート基内のNH基)のプロトンの帰属ピーク(1H):8.3〜8.7ppm
イソシアヌレート基(イソシアヌレート基に直接結合するメチレン基(CH2基))のプロトンの帰属ピーク(6H):3.8ppm
アロファネート基とイソシアヌレート基とのモル比率=アロファネート基のプロトンの帰属ピークの積分値/(イソシアヌレート基のプロトンの帰属ピークの積分値/6)
2.原料
(1)ポリイソシアネート成分(a)の各成分の調製例
調製例1(イソシアネート(a−1)(PDIウレトジオン))
温度計、攪拌装置、窒素導入管および冷却管が装着された反応機において、窒素雰囲気下、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートを500質量部装入し、窒素を、そのペンタメチレンジイソシアネートの液相(反応液)に1時間導入した。窒素を1時間導入した後の、反応液の溶存酸素濃度は1質量ppmであった。その後、その反応液を150℃に昇温した。次いで、同温度で10時間反応を継続した後、反応を終了させた。そして、得られたペンタメチレンジイソシアネート誘導体の反応混合液を、薄膜蒸留装置(温度:120℃、真空度:93.3Pa)に通液して、未反応のペンタメチレンジイソシアネートモノマーを除去し、イソシアネート(a−1)を得た。
温度計、攪拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートを500質量部、イソブチルアルコールを0.5質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
温度計、攪拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートを500質量部、イソブチルアルコールを9.6質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
イソシアネート(a−1)のイソシアネート誘導体の調製例において、ペンタメチレンジイソシアネートをヘキサメチレンジイソシアネート(三井化学社製、商品名:タケネート700)に変更した以外は、同じ調製方法でイソシアネート(a−4)を得た。
温度計、攪拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、ヘキサメチレンジイソシアネート(三井化学社製 商品名:タケネート700)を500質量部、イソブチルアルコールを0.4質量部、2,6−ジ(tert−ブチル)−4−メチルフェノールを0.3質量部、トリス(トリデシル)ホスファイトを0.3質量部、それぞれ、装入し、80℃で2時間反応させた。
温度計、攪拌装置、窒素導入管および冷却管が装着された反応機において、窒素雰囲気下、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートを500質量部装入し、窒素を、そのペンタメチレンジイソシアネートの液相(反応液)に1時間導入した。窒素を1時間導入した後の、反応液の溶存酸素濃度は1質量ppmであった。その後、反応液を150℃に昇温した。次いで、同温度で1時間反応継続した後、反応を終了した。そして、得られたペンタメチレンジイソシアネート誘導体の反応混合液を、薄膜蒸留装置(温度:120℃、真空度:93.3Pa)に通液して、未反応のペンタメチレンジイソシアネートモノマーを除去し、イソシアネート(a−6)を得た。
温度計、攪拌装置、還流管、および、窒素導入管を備えた4つ口フラスコに、国際公開第2012/121291号パンフレットの明細書における実施例1と同様にして製造されたペンタメチレンジイソシアネートを500質量部、イソブチルアルコールを0.8質量部、それぞれ、装入し、80℃で2時間ウレタン化反応させた。ウレタン化反応後のイソシアネート基濃度は、54.3質量%であった。
(2)ポリオール成分(b)
(ポリオール(b−1))
ポリエーテルポリオール(三井化学社製、商品名:アクトコールLR−00、数平均分子量(Mn)1600、官能基数f=3、OH価=110mgKOH/g)
(ポリオール(b−2))
ポリエーテルポリオール(三井化学社製、商品名:アクトコールT−700、数平均分子量(Mn)700、官能基数f=3、OH価=240mgKOH/g)
(3)触媒(c)
(触媒(c−1))
トリエチエンジアミンの33質量%ジプロピレングリコール溶液(エアプロダクツ社製、商品名:Dabco−33LV)
(触媒(c−2))
ビス(ジメチルアミノエチル)エーテルの70質量%ジプロピレングリコール溶液(モメンティブ社製、商品名:Niax−A1)
(触媒(c−3))
有機錫化合物(モメンティブ社製、商品名:Formrez UL−28)
(触媒(c−4))
有機錫化合物(三菱化学社製、商品名:Stanoct)
(4)発泡剤(d)
(発泡剤(d−1))
純水(H2O)
(5)整泡剤(e)
(整泡剤(e−1))
シリコーン整泡剤(エボニック社製、商品名:B−8545)
(整泡剤(e−2))
シリコーン整泡剤(エボニック社製、商品名:B−8002)
(6)安定剤(f)
(安定剤(f−1))
ヒンダードアミン化合物(耐光安定剤、BASFジャパン社製、商品名:チヌビン765)
(安定剤(f−2))
有機リン化合物(酸化防止剤、城北化学社製、商品名:JP−308E)
3.実施例1〜9および比較例1〜7(無黄変軟質ポリウレタンフォームの製造)
(1)実施例1
下記の表1に示した成分(原料)のうち、ポリイソシアネート成分以外の各成分を秤量し、温度23℃、相対湿度55%の実験室内で、それらを、表1の配合処方に従って配合して、それらが均一になるように攪拌混合して、プレミックスを調製した。
(2)実施例2〜10および比較例1〜7
下記の表1〜4の配合処方に従って秤量した以外は、実施例1と同様にして、無黄変軟質ポリウレタンフォームを得た。
4.無黄変軟質ポリウレタンフォームの評価
<反応時間(クリームタイム(CT))の測定方法>
各実施例および各比較例の無黄変軟質ポリウレタンフォームの製造において、ハンドミキサーで撹拌を開始したときから、プレミックスとポリイソシアネート成分とが反応することによりそれらの混合物が動き始めるまでの時間をクリームタイムとして測定した。
各実施例および各比較例の無黄変軟質ポリウレタンフォームの中心部(コア)より10×10×5cmのサイズの直方体を切り出して、測定試料を作製し、その後、測定試料の見かけ密度をJIS K7222(2005年)に従って測定した。
各実施例および各比較例の無黄変軟質ポリウレタンフォームの中心部(コア)より10×10×5cmのサイズの直方体を切り出して、測定試料を作製し、その後、JIS K−6400(2012年)に準拠して測定試料の硬さ(25%CLD)を測定した。
各実施例および各比較例の無黄変軟質ポリウレタンフォームの中心部より厚み10mmのサイズに切り出して、1号形試験片様にサンプルを打抜いて測定試料を作製し、引張圧縮試験機(インテスコ社製、Model205N)を用いて、JIS K−6400(2012年)に従って引張試験し、破断時における伸びを算出した。
各実施例および各比較例の無黄変軟質ポリウレタンフォームの中心部より厚み10mmのサイズに切り出して、測定試料を作製し、その後、測定試料に、紫外線蛍光灯が取り付けられたQUVウェザリングテスター(Qパネル社製)を使用して24時間にわたり短波長の紫外線を含む光(波長270〜720nm)を照射した。
以下に表1〜4中で用いた略号の詳細を示す。
アクトコールLR−00:ポリエーテルポリオール(三井化学社製、数平均分子量(Mn)1600、官能基数f=3、OH価=110mgKOH/g)
アクトコールT−700:ポリエーテルポリオール(三井化学社製、数平均分子量(Mn)700、官能基数f=3、OH価=240mgKOH/g)
Dabco 33LV:トリエチレンジアミンの33質量%ジプロピレングリコール溶液(エアプロダクツ社製)
Niax A−1:ビス(ジメチルアミノエチル)エーテルの70質量%ジプロピレングリコール溶液(モメンティブ社製)
Formrez UL−28:有機錫化合物(モメンティブ社製)
stanoct:有機錫化合物(三菱化学社製)
B−8545:シリコーン整泡剤(エボニック社製)
B−8002:シリコーン整泡剤(エボニック社製)
Tin.765:ヒンダードアミン化合物(耐光安定剤、BASFジャパン社製)
JP−308E:有機リン化合物(酸化防止剤、城北化学社製)
なお、上記説明は、本発明の例示の実施形態として提供したが、これは単なる例示にすぎず、限定的に解釈してはならない。当該技術分野の当業者によって明らかな本発明の変形例は、後記の請求の範囲に含まれるものである。
Claims (8)
- ポリイソシアネート成分と、ポリオール成分とを、少なくとも触媒および発泡剤の存在下において、反応させることにより得られ、
前記ポリイソシアネート成分が、ペンタメチレンジイソシアネートのウレトジオン2分子体を10〜95質量%含有することを特徴とする、無黄変軟質ポリウレタンフォーム。 - 前記ポリイソシアネート成分が、
ペンタメチレンジイソシアネートの、前記ウレトジオン2分子体を含むウレトジオン誘導体と、
脂肪族ポリイソシアネートの三量体誘導体と
を含有することを特徴とする、請求項1に記載の無黄変軟質ポリウレタンフォーム。 - 前記三量体誘導体が、イソシアヌレート基とアロファネート基とを含み、
前記アロファネート基の含有割合が、前記イソシアヌレート基1モルに対して、0.10モル以上0.70モル以下であることを特徴とする、請求項2に記載の無黄変軟質ポリウレタンフォーム。 - 前記脂肪族ポリイソシアネートが、ペンタメチレンジイソシアネートおよび/またはヘキサメチレンジイソシアネートであることを特徴とする、請求項2に記載の無黄変軟質ポリウレタンフォーム。
- 請求項1に記載の無黄変軟質ポリウレタンフォームから形成されることを特徴とする、衣料材料。
- 請求項5に記載の衣料材料から形成されることを特徴とする、ブラジャーのパッド。
- 請求項6に記載のブラジャーのパッドを備えることを特徴とする、ブラジャーのカップ。
- ペンタメチレンジイソシアネートのウレトジオン2分子体を10〜95質量%含有するポリイソシアネート成分と、ポリオール成分とを、少なくとも触媒および発泡剤の存在下において反応させることを特徴とする、無黄変軟質ポリウレタンフォームの製造方法。
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JP7096704B2 (ja) * | 2018-05-23 | 2022-07-06 | 三井化学株式会社 | ポリウレタンフォーム、衣料材料、ブラジャーのパッド、ブラジャーのカップ、および、ポリウレタンフォームの製造方法 |
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- 2016-05-09 JP JP2017517924A patent/JP6454783B2/ja active Active
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CN107406566A (zh) | 2017-11-28 |
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EP3296336A1 (en) | 2018-03-21 |
EP3296337A4 (en) | 2018-12-26 |
KR101991605B1 (ko) | 2019-06-20 |
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US10392528B2 (en) | 2019-08-27 |
EP3296336A4 (en) | 2018-12-26 |
JP6482657B2 (ja) | 2019-03-13 |
CN107531860A (zh) | 2018-01-02 |
TW201702280A (zh) | 2017-01-16 |
WO2016181920A1 (ja) | 2016-11-17 |
US20180142123A1 (en) | 2018-05-24 |
JPWO2016181920A1 (ja) | 2018-03-01 |
EP3296337A1 (en) | 2018-03-21 |
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