CA2153583A1 - Process for the preparation of polyketone fibres - Google Patents
Process for the preparation of polyketone fibresInfo
- Publication number
- CA2153583A1 CA2153583A1 CA002153583A CA2153583A CA2153583A1 CA 2153583 A1 CA2153583 A1 CA 2153583A1 CA 002153583 A CA002153583 A CA 002153583A CA 2153583 A CA2153583 A CA 2153583A CA 2153583 A1 CA2153583 A1 CA 2153583A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- solvent
- process according
- temperature
- solution
- Prior art date
- 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.)
- Abandoned
Links
- 229920001470 polyketone Polymers 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 47
- 238000002360 preparation method Methods 0.000 title claims description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 117
- 239000002904 solvent Substances 0.000 claims abstract description 90
- 238000001816 cooling Methods 0.000 claims abstract description 21
- 238000009835 boiling Methods 0.000 claims abstract description 16
- 238000002844 melting Methods 0.000 claims abstract description 12
- 230000008018 melting Effects 0.000 claims abstract description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 27
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 10
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 9
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 5
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 claims description 4
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 claims description 4
- 229960001826 dimethylphthalate Drugs 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940117927 ethylene oxide Drugs 0.000 claims description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 4
- 235000012438 extruded product Nutrition 0.000 claims description 3
- WLVPRARCUSRDNI-UHFFFAOYSA-N 2-hydroxy-1-phenyl-1-propanone Chemical compound CC(O)C(=O)C1=CC=CC=C1 WLVPRARCUSRDNI-UHFFFAOYSA-N 0.000 claims description 2
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
- YVIVRJLWYJGJTJ-UHFFFAOYSA-N gamma-Valerolactam Chemical compound CC1CCC(=O)N1 YVIVRJLWYJGJTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960001867 guaiacol Drugs 0.000 claims description 2
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- 238000000465 moulding Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 67
- 239000000047 product Substances 0.000 description 20
- 239000000499 gel Substances 0.000 description 19
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000009987 spinning Methods 0.000 description 12
- 238000004898 kneading Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000005711 Benzoic acid Substances 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012667 polymer degradation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 241000518994 Conta Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000338118 Dulus Species 0.000 description 1
- 101000800807 Homo sapiens Tumor necrosis factor alpha-induced protein 8 Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 102100033649 Tumor necrosis factor alpha-induced protein 8 Human genes 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001891 gel spinning Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/30—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising olefins as the major constituent
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Multicomponent Fibers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL9300060 | 1993-01-13 | ||
| NL9300060 | 1993-01-13 | ||
| PCT/EP1994/000061 WO1994016127A1 (en) | 1993-01-13 | 1994-01-07 | Process for the preparation of polyketone fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2153583A1 true CA2153583A1 (en) | 1994-07-21 |
Family
ID=19861906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002153583A Abandoned CA2153583A1 (en) | 1993-01-13 | 1994-01-07 | Process for the preparation of polyketone fibres |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0679201B1 (de) |
| JP (1) | JP3411279B2 (de) |
| CN (1) | CN1116435A (de) |
| AT (1) | ATE167534T1 (de) |
| BR (1) | BR9405807A (de) |
| CA (1) | CA2153583A1 (de) |
| DE (1) | DE69411146T2 (de) |
| ES (1) | ES2120008T3 (de) |
| RU (1) | RU2121017C1 (de) |
| UA (1) | UA42708C2 (de) |
| WO (1) | WO1994016127A1 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2733844B1 (fr) * | 1995-05-03 | 1997-06-06 | Alcatel Cable | Fibre optique et ruban de fibres optiques, et procede de fabrication associe |
| US7015303B1 (en) | 1998-08-10 | 2006-03-21 | Asahi Kasei Kabushiki Kaisha | Polyketone solution |
| US6818728B2 (en) | 2001-02-27 | 2004-11-16 | Asahi Kasei Kabushiki Kaisha | Polyketone fiber and process for producing the same |
| KR100730681B1 (ko) | 2002-08-29 | 2007-06-21 | 아사히 가세이 셍이 가부시키가이샤 | 폴리케톤 섬유 및 그의 제조 방법 |
| JP2007283896A (ja) | 2006-04-17 | 2007-11-01 | Bridgestone Corp | 空気入りタイヤ |
| KR101373832B1 (ko) * | 2012-03-23 | 2014-03-14 | 아주대학교산학협력단 | 벤질알콜 용매를 사용한 폴리케톤의 제조방법 |
| CN111647960B (zh) * | 2020-05-09 | 2021-06-11 | 中国水产科学研究院东海水产研究所 | 一种海洋牧场用降耗减阻丝的制造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8822349D0 (en) * | 1988-09-22 | 1988-10-26 | Shell Int Research | Process for preparation of thermoplastic fibres |
| NL8901253A (nl) * | 1989-05-19 | 1990-12-17 | Stamicarbon | Polymere filamenten, bandjes en films met een hoge modulus, een hoge sterkte en een hoge smelttemperatuur en een werkwijze voor de vervaardiging hiervan. |
| ATE131548T1 (de) * | 1990-05-09 | 1995-12-15 | Akzo Nobel Nv | Verfahren zur herstellung von polyketonfasern |
| NL9002666A (nl) * | 1990-12-05 | 1992-07-01 | Stamicarbon | Samenstelling van een etheen-koolmonoxide-copolymeer. |
-
1994
- 1994-01-07 AT AT94904651T patent/ATE167534T1/de not_active IP Right Cessation
- 1994-01-07 ES ES94904651T patent/ES2120008T3/es not_active Expired - Lifetime
- 1994-01-07 JP JP50758194A patent/JP3411279B2/ja not_active Expired - Fee Related
- 1994-01-07 CN CN94190937A patent/CN1116435A/zh active Pending
- 1994-01-07 WO PCT/EP1994/000061 patent/WO1994016127A1/en active IP Right Grant
- 1994-01-07 CA CA002153583A patent/CA2153583A1/en not_active Abandoned
- 1994-01-07 RU RU95116596A patent/RU2121017C1/ru active
- 1994-01-07 UA UA95073315A patent/UA42708C2/uk unknown
- 1994-01-07 BR BR9405807A patent/BR9405807A/pt not_active IP Right Cessation
- 1994-01-07 EP EP94904651A patent/EP0679201B1/de not_active Expired - Lifetime
- 1994-01-07 DE DE69411146T patent/DE69411146T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| UA42708C2 (uk) | 2001-11-15 |
| ES2120008T3 (es) | 1998-10-16 |
| ATE167534T1 (de) | 1998-07-15 |
| DE69411146T2 (de) | 1999-01-07 |
| JPH08507328A (ja) | 1996-08-06 |
| RU2121017C1 (ru) | 1998-10-27 |
| WO1994016127A1 (en) | 1994-07-21 |
| CN1116435A (zh) | 1996-02-07 |
| BR9405807A (pt) | 1995-12-19 |
| EP0679201B1 (de) | 1998-06-17 |
| JP3411279B2 (ja) | 2003-05-26 |
| DE69411146D1 (de) | 1998-07-23 |
| EP0679201A1 (de) | 1995-11-02 |
| RU95116596A (ru) | 1997-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |