JP7445776B2 - 耐汚染性分岐鎖状ポリアミド - Google Patents
耐汚染性分岐鎖状ポリアミド Download PDFInfo
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- 239000004952 Polyamide Substances 0.000 title claims description 105
- 229920002647 polyamide Polymers 0.000 title claims description 105
- 239000000203 mixture Substances 0.000 claims description 93
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 claims description 49
- 239000000835 fiber Substances 0.000 claims description 40
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 26
- 239000000539 dimer Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 150000004985 diamines Chemical class 0.000 claims description 16
- 150000001412 amines Chemical group 0.000 claims description 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 6
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 6
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 6
- DEJILVUPOQKKFM-UHFFFAOYSA-L dilithium;5-sulfobenzene-1,3-dicarboxylate Chemical compound [Li+].[Li+].OS(=O)(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 DEJILVUPOQKKFM-UHFFFAOYSA-L 0.000 claims description 6
- PBOFFNYRKURMFP-UHFFFAOYSA-L dipotassium;5-sulfobenzene-1,3-dicarboxylate Chemical compound [K+].[K+].OS(=O)(=O)C1=CC(C([O-])=O)=CC(C([O-])=O)=C1 PBOFFNYRKURMFP-UHFFFAOYSA-L 0.000 claims description 6
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 6
- 229910001416 lithium ion Inorganic materials 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 229910001414 potassium ion Inorganic materials 0.000 claims description 6
- 229910001415 sodium ion Inorganic materials 0.000 claims description 6
- YXTFRJVQOWZDPP-UHFFFAOYSA-M sodium;3,5-dicarboxybenzenesulfonate Chemical compound [Na+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 YXTFRJVQOWZDPP-UHFFFAOYSA-M 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 238000004804 winding Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- HPEUEJRPDGMIMY-IFQPEPLCSA-N molybdopterin Chemical compound O([C@H]1N2)[C@H](COP(O)(O)=O)C(S)=C(S)[C@@H]1NC1=C2N=C(N)NC1=O HPEUEJRPDGMIMY-IFQPEPLCSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000003951 lactams Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- AMOKUAKXKXBFIW-WJDWOHSUSA-N 9-[(z)-non-3-enyl]-10-octylnonadecanedioic acid Chemical compound OC(=O)CCCCCCCCC(CCCCCCCC)C(CCCCCCCC(O)=O)CC\C=C/CCCCC AMOKUAKXKXBFIW-WJDWOHSUSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004687 Nylon copolymer Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000012741 allura red AC Nutrition 0.000 description 1
- 239000004191 allura red AC Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000016776 visual perception Effects 0.000 description 1
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- 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
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
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- 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
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
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- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- C08G69/14—Lactams
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- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- 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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Description
本出願は、その全内容が参照により本明細書に援用される、2020年2月19日に出願された米国仮特許出願第62/978,465号の優先権を主張するものである。
例1 - 5-スルホイソフタル酸塩の残基を含む分岐鎖状ポリアミド組成物の製造(分岐鎖状SIPAポリアミド)
この例では、5-スルホイソフタル酸塩(SIPA)の残基を含む分岐鎖状ポリアミド組成物の製造について示す。反応器は、12Lのステンレス鋼容器にらせん型撹拌器を取り付けることで準備した。反応器に供給した反応物は、4760グラムのカプロラクタム(AdvanSix Resins and Chemicals LLC,Parsippany,NJ)、672グラムのPripol(商標)1013ダイマー酸(Croda Incorporated,Wilmington DE)、39.8グラムの5-スルホイソフタル酸ナトリウム(Sigma-Aldrich Corp.,St.Louis,MO)、及び70重量%のヘキサメチレンジアミン及び30重量%の水から本質的に成る195グラムの溶液(Sigma-Aldrich Corp.,St.Louis,MO)を含んでいた。縮合触媒も、次亜リン酸塩の形態で約100ppmの濃度で反応器に供給し、さらには100グラムの脱イオン水も供給した。
この例では、例1の分岐鎖状SIPAポリアミド組成物の性能を、二重末端封止ポリアミドポリマーDTPP(Aegis(登録商標)MBM、AdvanSix Incorporated,Parsippany,NJから入手可能)、非末端封止ナイロン-6(Aegis(登録商標)H55ZIE、AdvanSix Incorporatedから入手可能)、及び市販の耐汚染性ポリアミドポリマーと比較する。例1の分岐鎖状SIPAポリアミド組成物のマルチフィラメント繊維を、6~12ポンド/時間の速度で一軸押出機から分岐鎖状SIPAポリアミド組成物を押出すことによって製造した。押出機は、2インチの軸径及び27対1の長さ対軸径比を有する混合を伴うものであった。押出機のゾーン温度は、約750psigの押出機圧力(3500-1~7000秒-1のキャピラリーせん断粘度(capillary shear viscosity))のために、255℃~265℃に設定した。クロスフローエアクエンチング(cross flow air quenching)(40%フロー、24℃、50%相対湿度)を伴う0.4mm径キャピラリーを有する紡糸口金を用いて、紡糸口金の出口部から最初の駆動巻き取りロールまで約10フィートのスタック高さ(stack height)で繊維を紡糸した。
式2:
ΔE=((ΔL2)+(Δa2)+(Δb2))0.5
標準ΔEは、染料取り込みによる汚染に起因する色変化の尺度となる。ポリマーチップ、及びポリマーチップから形成した繊維の両方について測定した。結果を表2に示す。
Claims (20)
- 以下の式を有し、
a=6乃至10、
b=6乃至10、
c=4乃至10、
d=4乃至10、
n=1乃至20、
p=1乃至1000、
m=1乃至400、及び
x=4乃至200、であるポリアミド組成物。 - 5-スルホイソフタル酸の塩の残基を含む、請求項1に記載のポリアミド組成物。
- 前記スルホイソフタル酸の塩が、5-スルホイソフタル酸ナトリウム、5-スルホイソフタル酸リチウム、及び5-スルホイソフタル酸カリウムから成る群より選択される、請求項2に記載のポリアミド組成物。
- 前記スルホイソフタル酸の塩の前記残基の濃度が、前記ポリアミド組成物の総重量に基づいて、0.1重量%乃至15重量%である、請求項2に記載のポリアミド組成物。
- 各々が6個以上の炭素を有する2つの炭素鎖を含むダイマー酸の残基を含む、請求項1に記載のポリアミド組成物。
- 前記ダイマー酸の残基の濃度が、前記ポリアミド組成物の総重量に基づいて、6重量%乃至18重量%である、請求項5に記載のポリアミド組成物。
- 前記ポリアミド組成物の総アミン末端基濃度が、約5ミリモル/キログラム乃至約50ミリモル/キログラムである、請求項1に記載のポリアミド組成物。
- 前記ポリアミド組成物の相対粘度(RV)が、GB/T 12006.1-2009/ISO 307:2007によって特定した場合、約2.0乃至約7.0RVである、請求項1に記載のポリアミド組成物。
- 前記ポリアミド組成物のギ酸粘度が、ASTM D-789-07によって測定した場合、約200FAV乃至約950FAVである、請求項1に記載のポリアミド組成物。
- CIE DE2000に従う色差ΔEが、10未満である、請求項1に記載のポリアミド組成物。
- 3.0乃至7.0グラム/デニールのテナシティを有する、請求項1に記載のポリアミド組成物から形成された繊維。
- 6.0乃至7.0グラム/デニールのテナシティを有する、請求項11に記載の繊維。
- 以下の式を有するポリアミド組成物の製造方法であって、
カプロラクタム、ダイマー酸、ジアミン、及び、5-スルホイソフタル酸塩又は5-スルホイソフタル酸のうちの少なくとも1つを反応器に供給することと、
前記カプロラクタム、前記ダイマー酸、前記ジアミン、並びに5-スルホイソフタル酸塩及び5-スルホイソフタル酸のうちの前記少なくとも1つを前記反応器中で一緒に混合することと、
前記カプロラクタム、前記ダイマー酸、前記ジアミン、並びに5-スルホイソフタル酸塩及び5-スルホイソフタル酸のうちの前記少なくとも1つを前記反応器中、反応温度で反応させることと、
を含む、方法。 - 前記供給工程において、5-スルホイソフタル酸塩及び5-スルホイソフタル酸のうちの前記少なくとも1つが、前記ポリアミド組成物の総重量に基づいて、0.1重量%乃至15重量%である、請求項13に記載の方法。
- 前記供給工程において、5-スルホイソフタル酸塩及び5-スルホイソフタル酸のうちの前記少なくとも1つが、5-スルホイソフタル酸ナトリウム、5-スルホイソフタル酸リチウム、及び5-スルホイソフタル酸カリウムから成る群より選択される5-スルホイソフタル酸塩である、請求項13に記載の方法。
- 前記供給工程において、前記ジアミンが、ヘキサメチレンジアミンを含む、請求項13に記載の方法。
- 前記供給工程において、前記ダイマー酸が、前記ポリアミド組成物の総重量に基づいて、6重量%乃至18重量%である、請求項13に記載の方法。
- 前記反応工程において、前記反応器が、前記反応工程の一部分で加圧される、請求項13に記載の方法。
- 前記反応工程において、前記反応器が、前記反応工程の一部分で真空下とされる、請求項13に記載の方法。
- 前記反応工程において、前記反応温度が、約225℃乃至約290℃である、請求項13に記載の方法。
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