JPS6053537A - 親水性ポリエ−テルエステルアミドの製造方法 - Google Patents

Info

Publication number

JPS6053537A

JPS6053537A JP16042483A JP16042483A JPS6053537A JP S6053537 A JPS6053537 A JP S6053537A JP 16042483 A JP16042483 A JP 16042483A JP 16042483 A JP16042483 A JP 16042483A JP S6053537 A JPS6053537 A JP S6053537A

Authority

JP

Japan

Prior art keywords

nylon

salt

polyether ester

nylon salt

methylene groups

Prior art date

1983-09-02

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

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• 229920006146 polyetheresteramide block copolymer Polymers 0.000 title claims description 21
• 238000004519 manufacturing process Methods 0.000 title claims description 8
• 150000003839 salts Chemical class 0.000 claims abstract description 80
• 239000004677 Nylon Substances 0.000 claims abstract description 56
• 229920001778 nylon Polymers 0.000 claims abstract description 56
• 239000007858 starting material Substances 0.000 claims abstract description 27
• 239000004952 Polyamide Substances 0.000 claims abstract description 25
• 229920002647 polyamide Polymers 0.000 claims abstract description 25
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 23
• -1 aliphatic diamine Chemical class 0.000 claims abstract description 16
• 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 14
• 150000002148 esters Chemical class 0.000 claims abstract description 14
• 229920000570 polyether Polymers 0.000 claims abstract description 14
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 13
• 238000006243 chemical reaction Methods 0.000 claims abstract description 9
• 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
• 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 4
• 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 4
• 239000002253 acid Substances 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 11
• 150000001875 compounds Chemical class 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 238000006068 polycondensation reaction Methods 0.000 claims description 2
• 229920001577 copolymer Polymers 0.000 abstract description 4
• 150000004985 diamines Chemical class 0.000 abstract description 4
• 125000003368 amide group Chemical group 0.000 abstract description 2
• 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
• 125000004432 carbon atom Chemical group C* 0.000 abstract 1
• 238000006116 polymerization reaction Methods 0.000 description 19
• 229920001007 Nylon 4 Polymers 0.000 description 11
• 229920000642 polymer Polymers 0.000 description 11
• 229920000232 polyglycine polymer Polymers 0.000 description 7
• 229920002292 Nylon 6 Polymers 0.000 description 6
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 5
• 238000000265 homogenisation Methods 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 3
• 239000001361 adipic acid Substances 0.000 description 3
• 235000011037 adipic acid Nutrition 0.000 description 3
• 229960002684 aminocaproic acid Drugs 0.000 description 3
• 150000001991 dicarboxylic acids Chemical class 0.000 description 3
• 239000000806 elastomer Substances 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• 229920003188 Nylon 3 Polymers 0.000 description 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000000835 fiber Substances 0.000 description 2
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
• 230000000704 physical effect Effects 0.000 description 2
• 239000002685 polymerization catalyst Substances 0.000 description 2
• KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 230000009257 reactivity Effects 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
• QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
• DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
• NMVNAVLEAQBLGM-UHFFFAOYSA-N 2-tert-butyl-2-[(4-hydroxyphenyl)methyl]-3,3-dimethylbutanamide Chemical compound CC(C)(C)C(C(C)(C)C)(C(N)=O)CC1=CC=C(O)C=C1 NMVNAVLEAQBLGM-UHFFFAOYSA-N 0.000 description 1
• UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 1
• WXIOPKYMMKAUEP-UHFFFAOYSA-N C(CCCCCCCCC)(C(=O)O)C(=O)O.C(CCCCCCCCCCC(=O)O)(=O)O Chemical compound C(CCCCCCCCC)(C(=O)O)C(=O)O.C(CCCCCCCCCCC(=O)O)(=O)O WXIOPKYMMKAUEP-UHFFFAOYSA-N 0.000 description 1
• JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
• 229920000571 Nylon 11 Polymers 0.000 description 1
• 229920000299 Nylon 12 Polymers 0.000 description 1
• 229920003189 Nylon 4,6 Chemical class 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
• QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
• BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
• 125000002723 alicyclic group Chemical group 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 description 1
• YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
• 238000000071 blow moulding Methods 0.000 description 1
• YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 238000003490 calendering Methods 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 230000000052 comparative effect Effects 0.000 description 1
• 239000002131 composite material Substances 0.000 description 1
• 238000000748 compression moulding Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• 238000001125 extrusion Methods 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229910052735 hafnium Inorganic materials 0.000 description 1
• VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
• 239000012456 homogeneous solution Substances 0.000 description 1
• 238000007731 hot pressing Methods 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 238000001746 injection moulding Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 238000000465 moulding Methods 0.000 description 1
• RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
• 230000000379 polymerizing effect Effects 0.000 description 1
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 239000005060 rubber Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 229920001169 thermoplastic Polymers 0.000 description 1
• 239000004416 thermosoftening plastic Substances 0.000 description 1
• 229910052719 titanium Inorganic materials 0.000 description 1
• 239000010936 titanium Substances 0.000 description 1
• 229940116269 uric acid Drugs 0.000 description 1
• 229910052726 zirconium Inorganic materials 0.000 description 1