JP2019520464A - 高Tgを有するBACT/XTコポリアミドから製造されたバリア構造 - Google Patents
高Tgを有するBACT/XTコポリアミドから製造されたバリア構造 Download PDFInfo
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- JP2019520464A JP2019520464A JP2019500835A JP2019500835A JP2019520464A JP 2019520464 A JP2019520464 A JP 2019520464A JP 2019500835 A JP2019500835 A JP 2019500835A JP 2019500835 A JP2019500835 A JP 2019500835A JP 2019520464 A JP2019520464 A JP 2019520464A
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- copolyamide
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- 238000011955 best available control technology Methods 0.000 title claims abstract description 47
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- -1 1,3-bis (aminomethyl) cyclohexyl Chemical group 0.000 claims abstract description 34
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims abstract description 21
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- XGSHEASGZHYHBU-UHFFFAOYSA-N tetradecane-1,1-diamine Chemical compound CCCCCCCCCCCCCC(N)N XGSHEASGZHYHBU-UHFFFAOYSA-N 0.000 description 1
- MSVPBWBOFXVAJF-UHFFFAOYSA-N tetradecane-1,14-diamine Chemical compound NCCCCCCCCCCCCCCN MSVPBWBOFXVAJF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
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Abstract
Description
−40〜95モル%の10T
−5〜40%の6T。
Aは、アミノカルボン酸から得られるモチーフ、ラクタムから得られるモチーフ、及び式(ジアミンCa).(ジ(環式)脂肪族酸Cb)を有するモチーフから選択され、aはジアミン中の炭素原子数を表し、bは二酸中の炭素原子の数を表し、a及びbはそれぞれ包括的に4〜36の間の値であり;
ゲルパーミエーションクロマトグラフィにより測定して、3.5以下の多分子指数(polymolecularity index)Ipを有することを特徴とする。
−BACTは、20〜70%、好ましくは25〜60%、より好ましくは35〜55%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、BACは、1,3−ビス(アミノメチル)シクロヘキサン(1,3−BAC)、1,4−ビス(アミノメチル)シクロヘキシル(1,4−BAC)又はそれらの混合物から選択され、Tはテレフタル酸であり、
−XTは、30〜80%、好ましくは40〜75%、より好ましくは45〜65%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、Xは、C9−C18直鎖脂肪族ジアミン、好ましくはC9、C10、C11又はC12であり、Tは、テレフタル酸、好ましくはC10、C11又はC12であり、
−BACT及び/又はXT単位において、互いに独立して、ジカルボン酸の総量に対して、30モル%まで、好ましくは20モル%まで、特に10モル%までのテレフタル酸を、6〜36個の炭素原子、特に6〜14個の炭素原子を含む他のジ芳香族酸、ジ脂肪族酸又はジ(環式)脂肪族酸によって置き換えることができ、及び
−BACT及び/又はXT単位において、互いに独立して、ジアミン総量に対して、30モル%まで、好ましくは20モル%、特に10モル%までのBAC及び/又は該当する場合にはXを、4〜36個の炭素原子、特に6〜12個の炭素原子を含む他のジアミンで置き換えることができ、及び
−コポリアミドにおいて、モノマーの総量に対して、30モル%以下、好ましくは20モル%以下、好ましくは10モル%以下が、ラクタム又はアミノカルボン酸によって形成でき、及び
−ただし、テレフタル酸、BAC及びXに置き換わるモノマーの合計は、コポリアミド中で使用されるモノマーの総量に対して30モル%、好ましくは20モル%、好ましくは10モル%の濃度を超えず、及び
−ただし、BACT及びXT単位は依然としてコポリアミド中に存在し、
この層は強化繊維を含まない。
−BACTは、20〜70%、好ましくは25〜60%、より好ましくは35〜55%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここでBACは1,3−ビス(アミノメチル)シクロヘキサン(1,3−BAC)、1,4−ビス(アミノメチル)シクロヘキシル(1,4−BAC)又はそれらの混合物から選択され、Tはテレフタル酸である、
−XTは、30〜80%、好ましくは40〜75%、より好ましくは45〜65%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、Xは、C9−C18直鎖脂肪族ジアミン、好ましくはC9、C10、C11又はC12であり、Tは、テレフタル酸、好ましくはC10、C11又はC12である。
−BACT及び/又はXT単位において、互いに独立して、ジアミン総量に対して、30モル%まで、好ましくは20モル%、特に10モル%までのBAC及び/又は該当する場合にはXを、4〜36個の炭素原子、特に6〜12個の炭素原子を含む他のジアミンで置き換えることができる、及び
−コポリアミドにおいて、モノマーの総量に対して、30モル%以下、好ましくは10モル%以下が、ラクタム又はアミノカルボン酸によって形成できる、及び
−ただし、テレフタル酸、BAC及びXに置き換わるモノマーの合計は、コポリアミド中で使用されるモノマーの総量に対して30モル%、好ましくは10モル%の濃度を超えない、及び
−ただし、BACT及びXT単位は依然としてこのコポリアミド中に存在する、
この層は強化繊維を含まない。
−無機繊維、特に炭素繊維(ナノチューブ又はカーボンナノチューブ(CNT)、カーボンナノファイバ又はグラフェンの繊維を含む。);シリカ繊維、例えばガラス繊維、特にタイプE、R又はS2;ホウ素繊維;セラミック繊維、特に炭化ケイ素繊維、炭化ホウ素繊維、炭窒化ホウ素繊維、窒化ケイ素繊維、窒化ホウ素繊維、玄武岩繊維;金属及び/又はそれらの合金を含む繊維又はフィラメント;金属酸化物繊維、特にアルミナ(Al2O3);金属化繊維、例えば金属化ガラス繊維及び金属化炭素繊維、又は前述の繊維の混合物。
・熱硬化性ポリマー繊維、より詳細には:不飽和ポリエステル、エポキシ樹脂、ビニルエステル、フェノール樹脂、ポリウレタン、シアノアクリレート及びポリイミド、例えばビスマレイミド樹脂、メラミンなどのアミンとグルオキサール又はホルムアルデヒドのようなアルデヒドとの反応から生じるアミノプラストから選択される繊維
・熱可塑性ポリマーの繊維、より詳細には:ポリエチレンテレフタレート(PET)、ポリブチレンテレフタレート(PBT)から選択される繊維、
・ポリアミド繊維
・アラミド繊維(例えばKevlar(R))及び芳香族ポリアミド、例えば式:PPDT、MPD.I、PAA及びPPAのうちの1つを有するもの(PPD及びMPDはそれぞれp−及びm−フェニレンジアミンであり、PAAはポリアリールアミドであり、PPAはポリフタルアミドである。)
・ポリアミドブロックコポリマーの繊維、例えばポリアミド/ポリエーテル、ポリアリールエーテルケトン(PAEK)の繊維、例えばポリエーテルエーテルケトン(PEEK)、ポリエーテルケトンケトン(PEKK)、ポリエーテルケトンエーテルケトンケトン(PEKEKK)。
−フェノール酸化防止剤、例えばCibaのIrganox(R)245、Irganox(R)1010、Irganox(R)1098、CibaのIrganox(R)MD1024、Great LakesのLowinox(R)44B25、Adeka PalmaroleのADK(R)Stab AO−80。
−UV吸収剤、例えばCibaのTinuvin(R)312、
−前述のような、HALS、
−アミン系安定剤、例えばCromptonのNaugard(R)445、又はさらにヒンダードアミンタイプ、例えばCibaのTinuvin(R)770、
−多官能性安定剤、例えばClariantのNylostab(R)S−EED。
ここで:
−R1、R2、R3及びR4は、独立して、水素原子又は1〜6個の炭素原子を有するアルキルから選択される基を表し、
−Xは、単結合、又は以下から構成される二価の基のいずれかを表す:
−1〜10個の炭素原子を含み、6〜8個の炭素原子を有する脂環式又は芳香族基により任意選択的に置換される直鎖又は分枝鎖脂肪族鎖。
−6〜12個の炭素原子を有する脂環式基。
(3)//(2)//(1)又は(2)//(3)//(1)を含むか、又はそれから構成される。
−XTは、30〜80%、好ましくは40〜75%、より好ましくは45〜65%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、Xは、C9−C18直鎖脂肪族ジアミン、好ましくはC9、C10、C11又はC12であり、Tは、テレフタル酸、好ましくはC10、C11又はC12である。
−BACT及び/又はXT単位において、互いに独立して、ジアミン総量に対して、30モル%まで、好ましくは20モル%、特に10モル%までのBAC及び/又は該当する場合にはXを、4〜36個の炭素原子、特に6〜12個の炭素原子を含む他のジアミンで置き換えることができる、及び
−コポリアミドにおいて、モノマーの総量に対して、30モル%以下、好ましくは10モル%以下が、ラクタム又はアミノカルボン酸によって形成できる、及び
−ただし、テレフタル酸、BAC及びXに置き換わるモノマーの合計が、コポリアミド中で使用されるモノマーの総量に対して30モル%、好ましくは10モル%の濃度を超えない、及び
−ただし、BACT及びXT単位が依然としてこのポリアミドポリマー中に存在する、
構造、特に多層構造を製造するために、このBACT/XTコポリアミドを含む少なくとも1つのバリア層(1)を含み、
この構造は強化繊維を含まない。
以下の手順は調製方法の一例であり、限定的なものではない。それは、本発明によるすべての組成物及び比較組成物を代表するものである:
−500gの水
−ジアミン
−アミノ酸(任意選択的)
−テレフタル酸及び任意選択的に二酸のうちのどれか一方、
−単官能性連鎖調節剤:標的Mnに適した量で(安息香酸)50〜100gの範囲の安息香酸。
−35gの次亜リン酸ナトリウム(溶液中)
−0.1gのWACKER AK1000消泡剤(Wacker Siliconesから)。
Claims (37)
- BACT/XTコポリアミドを含む少なくとも1つの層(1)を含む構造であって、
−BACTは、20〜70%、好ましくは25〜60%、より好ましくは35〜55%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、BACは、1,3−ビス(アミノメチル)シクロヘキサン(1,3−BAC)、1,4−ビス(アミノメチル)シクロヘキシル(1,4−BAC)又はそれらの混合物から選択され、Tはテレフタル酸であり、
−XTは、30〜80%、好ましくは40〜75%、より好ましくは45〜65%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、Xは、C9−C18直鎖脂肪族ジアミン、好ましくはC9、C10、C11又はC12であり、Tは、テレフタル酸、好ましくはC10、C11又はC12であり、
−BACT及び/又はXT単位において、互いに独立して、ジカルボン酸の総量に対して、30モル%まで、好ましくは20モル%まで、特に10モル%までのテレフタル酸を、6〜36個の炭素原子、特に6〜14個の炭素原子を含む他のジ芳香族酸、ジ脂肪族酸又はジ(環式)脂肪族酸によって置き換えられることができ、
−BACT及び/又はXT単位において、互いに独立して、ジアミン総量に対して、30モル%まで、好ましくは20モル%、特に10モル%までのBAC及び/又は該当する場合にはXは、4〜36個の炭素原子、特に6〜12個の炭素原子を含む他のジアミンで置き換えることができ、
−前記コポリアミドにおいて、モノマーの総量に対して、30モル%以下、好ましくは10モル%以下が、ラクタム又はアミノカルボン酸によって形成でき、
−ただし、テレフタル酸、BAC及びXに置き換わるモノマーの合計が、前記コポリアミド中で使用されるモノマーの総量に対して30モル%、好ましくは10モル%の濃度を超えず、また
−ただし、BACT及びXT単位が依然としてポリアミドポリマー中に存在し、
前記構造が強化繊維を含まない、
構造。 - 前記コポリアミドが、規格ISO11357−3(2013)に従って求められる、<290℃、好ましくは<285℃、より好ましくは<280℃の融解温度Tmを有する、請求項1に記載の構造。
- 前記コポリアミドが、規格ISO11357−2:2013に従って求められる、>120℃、好ましくは>130℃、より好ましくは>140℃のガラス転移温度Tgを有する、請求項1又は2に記載の構造。
- 前記コポリアミドが、規格ISO11357−3:2013に従って求められる、<40℃、好ましくは<30℃の融解温度と結晶化温度との差Tm−Tcを有する、請求項1〜3のいずれか一項に記載の構造。
- 規格ISO11357−3:2013に従って示差走査熱量測定(DSC)によって測定される前記コポリアミドの結晶化エンタルピーが、40J/gより大きい、好ましくは45J/gより大きい、より好ましくは50J/gより大きいことを特徴とする、請求項1〜4のいずれか一項に記載の構造。
- 前記BACが1,3−BACである、請求項1〜5のいずれか一項に記載の構造。
- 前記BACが1,3−BACであり、XTが9T、10T、11T及び12Tから選択される、請求項1〜6のいずれか一項に記載の構造。
- 前記XTが10Tであり、10が1,10−デカンジアミンに相当する、請求項1〜7のいずれか一項に記載の構造。
- テレフタル酸、BAC及びXを置き換える前記モノマーの合計が0に等しい、請求項1〜8のいずれか一項に記載の構造。
- 前記層(1)が、耐衝撃性改質剤及び/又はコア−シェル型改質剤を含む、請求項1〜9のいずれか一項に記載の構造。
- 前記構造が単一層(1)から形成される、請求項1〜10のいずれか一項に記載の構造。
- 前記層(1)が、有機安定剤、無機安定剤、特に銅を含有する安定剤、又はそれらの混合物から選択される安定剤を含む、請求項1〜11のいずれか一項に記載の構造。
- 前記層(1)が、カーボンブラック及びグラファイトから選択される帯電防止充填剤、特にカーボンブラックを含む、請求項1〜12のいずれか一項に記載の構造。
- 前記層(1)が、酸化防止剤、熱安定剤、UV吸収剤、光安定剤、滑剤、無機充填剤、難燃剤、核形成剤、可塑剤及び着色剤から選択される少なくとも1つの添加剤を含む、請求項1〜13のいずれか一項に記載の構造。
- 第2の層(2)が存在し、層(1)と(2)とが互いに接着できる、請求項1〜10及び12〜14のいずれか一項に記載の構造。
- 前記層(2)が、脂肪族ポリアミド及び芳香族ポリアミドから選択される少なくとも1つのポリアミド、特に脂肪族ポリアミドを含む、請求項15に記載の構造。
- 前記脂肪族ポリアミドが、少なくとも1つのラクタム、アミノカルボン酸の重縮合由来、又はジアミン及びジカルボン酸の重縮合由来であり、前記ジアミンが、脂肪族ジアミン、芳香族ジアミン及び脂環式ジアミンから選択され、前記ジカルボン酸が、ジ脂肪族酸、ジ芳香族酸及びジ(環式)脂肪族酸、又はそれらの混合物から選択される、請求項16に記載の構造。
- 前記層(2)の脂肪族ポリアミドが、PA11、PA12、PA1010、PA1012、PA610及びPA612から選択される、請求項16〜17のいずれか一項に記載の構造。
- 層(2)とは異なる別のポリアミドが層(2)中に存在できる、請求項16〜18のいずれか一項に記載の構造。
- 可塑剤が層(2)中に存在する、請求項15〜19のいずれか一項に記載の構造。
- 耐衝撃性改質剤が層(2)中に存在する、請求項15〜20のいずれか一項に記載の構造。
- 前記層(2)が、有機安定剤、無機安定剤、特に銅を含有する安定剤、又はそれらの混合物から選択される安定剤を含む、請求項15〜21のいずれか一項に記載の構造。
- 前記層(1)が有機安定剤を含み、前記層(2)が、無機安定剤、特に銅を含有する安定剤を含む、請求項15〜22のいずれか一項に記載の構造。
- 前記層(1)が、無機安定剤、特に銅を含有する安定剤を含み、前記層(2)が有機安定剤を含む、請求項15〜22のいずれか一項に記載の構造。
- 前記層(2)が、カーボンブラック及びグラファイトから選択される帯電防止充填剤、特にカーボンブラックを含む、請求項15〜24のいずれか一項に記載の構造。
- 前記層(2)が、酸化防止剤、熱安定剤、UV吸収剤、光安定剤、滑剤、無機充填剤、難燃剤、核形成剤、可塑剤及び着色剤から選択される少なくとも1つの添加剤を含む、請求項15〜25のずれか一項に記載の構造。
- 前記層(1)が、特に流体に対するバリア層であり、前記流体が燃料から選択され、前記燃料が、ガソリン、特にバイオガソリン(ガソリン及びアルコール、特にメタノール又はエタノールの混合物)、又はディーゼル、特にバイオディーゼル、オイル、ブレーキ液、尿素溶液、グリコールを含有する冷却液、ガス、特に圧縮空気であり、前記バリア層(1)が前記流体と接触する、請求項1〜26のいずれか一項に記載の構造。
- 層(3)も含み、前記層(3)が、層(1)と同一又は異なる、請求項15〜27のいずれか一項に記載の構造。
- 層(3)が層(1)とは異なり、結合層であり、前記構造が、外側から内側にかけて以下の層:(2)//(3)//(1)を含み、層(1)が流体と接触する、請求項28に記載の構造。
- 少なくとも1つの他の層(4)が存在し、前記層(1)が前記流体と接触する、請求項28〜29のいずれか一項に記載の構造。
- 前記層(4)がEVOHの層である、請求項30に記載の構造。
- 前記構造が、外側から内側にかけて以下の層:(2)//(4)//(3)//(1)を含み、層(1)が流体と接触する、請求項30〜31のいずれか一項に記載の構造。
- 結合層(3)と同一又は異なる結合層(3’)が存在する、請求項28〜31のいずれか一項に記載の構造。
- 前記構造が、外側から内側にかけて以下の層:(2)//(3’)//(4)//(3)//(1)を含み、層(1)が流体と接触する、請求項33に記載の構造。
- 請求項1〜34のいずれか一項に記載の構造で製造されたボトル、タンク、コンテナ、チューブ及び容器。
- 請求項1〜34のいずれか一項に記載の構造で作られた包装。
- BACT/XTコポリアミドの使用であって、
−BACTは、20〜70%、好ましくは25〜60%、より好ましくは35〜55%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、BACは、1,3−ビス(アミノメチル)、シクロヘキサン(1,3−BAC)、1,4−ビス(アミノメチル)シクロヘキシル(1,4−BAC)又はそれらの混合物から選択され、及びTはテレフタル酸であり、
−XTは、30〜80%、好ましくは40〜75%、より好ましくは45〜65%の範囲のモル含有量で存在するアミドモチーフを有する単位であり、ここで、Xは、C9〜C18直鎖脂肪族ジアミン、好ましくはC9、C10、C11又はC12であり、Tは、テレフタル酸、好ましくはC10、C11又はC12であり、
−BACT及び/又はXT単位において、互いに独立して、ジカルボン酸の総量に対して、30モル%まで、好ましくは20モル%まで、特に10モル%までのテレフタル酸を、6〜36個の炭素原子、特に6〜14個の炭素原子を含む他のジ芳香族酸、ジ脂肪族酸又はジ(環式)脂肪族酸で置き換えることができ、及び
−BACT及び/又はXT単位において、互いに独立して、ジアミン総量に対して、30モル%まで、好ましくは20モル%、特に10モル%までのBAC及び/又は該当する場合にはXを、4〜36個の炭素原子、特に6〜12個の炭素原子を含む他のジアミンで置き換えることができ、
−前記コポリアミドにおいて、モノマーの総量に対して、30モル%以下、好ましくは10モル%以下が、ラクタム又はアミノカルボン酸によって形成できる、
−ただし、テレフタル酸、BAC及びXに置き換わるモノマーの合計が、前記コポリアミドに使用されるモノマーの総量に対して30モル%、好ましくは10モル%の濃度を超えず、また
−ただし、BACT及びXT単位が依然としてポリアミドポリマー中に存在し、
前記BAC、T/XTコポリアミドを含む少なくとも1つのバリア層(1)を含む構造、特に多層構造を製造するための使用であり、
前記構造が強化繊維を含まない、
使用。
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- 2017-07-10 JP JP2019500835A patent/JP7076427B2/ja active Active
- 2017-07-10 US US16/316,361 patent/US11813828B2/en active Active
- 2017-07-10 CN CN201780043211.5A patent/CN109476839B/zh active Active
- 2017-07-10 WO PCT/FR2017/051871 patent/WO2018011493A1/fr unknown
- 2017-07-10 EP EP17745844.5A patent/EP3481890B1/fr active Active
- 2017-07-10 KR KR1020197003568A patent/KR102330137B1/ko active IP Right Grant
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JP2020512450A (ja) * | 2017-03-24 | 2020-04-23 | アルケマ フランス | 熱可塑性材料のための高いガラス転移温度及び高い融点を有する半結晶性ポリアミド組成物、その製造方法及びその使用 |
JP7201608B2 (ja) | 2017-03-24 | 2023-01-10 | アルケマ フランス | 熱可塑性材料のための高いガラス転移温度及び高い融点を有する半結晶性ポリアミド組成物、その製造方法及びその使用 |
WO2022196711A1 (ja) * | 2021-03-16 | 2022-09-22 | 三井化学株式会社 | ポリアミド樹脂組成物およびポリアミド成形体 |
JP7523669B2 (ja) | 2021-03-16 | 2024-07-26 | 三井化学株式会社 | ポリアミド樹脂組成物およびポリアミド成形体 |
Also Published As
Publication number | Publication date |
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FR3053694B1 (fr) | 2018-07-06 |
CN109476839A (zh) | 2019-03-15 |
FR3053694A1 (fr) | 2018-01-12 |
KR20190031257A (ko) | 2019-03-25 |
KR102330137B1 (ko) | 2021-11-23 |
WO2018011493A1 (fr) | 2018-01-18 |
JP7076427B2 (ja) | 2022-05-27 |
EP3481890A1 (fr) | 2019-05-15 |
US20190232628A1 (en) | 2019-08-01 |
EP3481890B1 (fr) | 2020-01-29 |
US11813828B2 (en) | 2023-11-14 |
CN109476839B (zh) | 2021-11-02 |
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