CA1048682A - Block copolymer of poly(dioxa-arylamide) and polyamide - Google Patents
Block copolymer of poly(dioxa-arylamide) and polyamideInfo
- Publication number
- CA1048682A CA1048682A CA74213634A CA213634A CA1048682A CA 1048682 A CA1048682 A CA 1048682A CA 74213634 A CA74213634 A CA 74213634A CA 213634 A CA213634 A CA 213634A CA 1048682 A CA1048682 A CA 1048682A
- Authority
- CA
- Canada
- Prior art keywords
- copolymer
- nylon
- poly
- fiber
- polymer
- 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.)
- Expired
Links
- 239000004952 Polyamide Substances 0.000 title claims abstract description 25
- 229920002647 polyamide Polymers 0.000 title claims abstract description 25
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims abstract description 41
- 239000000835 fiber Substances 0.000 claims abstract description 39
- 229920002292 Nylon 6 Polymers 0.000 claims abstract description 16
- 238000009987 spinning Methods 0.000 claims description 7
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 238000001125 extrusion Methods 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000002074 melt spinning Methods 0.000 claims 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 2
- 238000002156 mixing Methods 0.000 abstract description 10
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 239000000155 melt Substances 0.000 abstract description 3
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000470 constituent Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 48
- 239000000203 mixture Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- -1 and Polymers 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000305 Nylon 6,10 Polymers 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007278 cyanoethylation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000013627 low molecular weight specie Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- CHDRADPXNRULGA-UHFFFAOYSA-N naphthalene-1,3-dicarboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(C(O)=O)=C21 CHDRADPXNRULGA-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 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
- FJXWKBZRTWEWBJ-UHFFFAOYSA-N nonanediamide Chemical compound NC(=O)CCCCCCCC(N)=O FJXWKBZRTWEWBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010104 thermoplastic forming Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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
- C08G69/40—Polyamides containing oxygen in the form of ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41561073A | 1973-11-14 | 1973-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048682A true CA1048682A (en) | 1979-02-13 |
Family
ID=23646410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74213634A Expired CA1048682A (en) | 1973-11-14 | 1974-11-13 | Block copolymer of poly(dioxa-arylamide) and polyamide |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5520490B2 (en, 2012) |
| BE (1) | BE822168A (en, 2012) |
| CA (1) | CA1048682A (en, 2012) |
| DE (1) | DE2454142C2 (en, 2012) |
| DK (1) | DK590474A (en, 2012) |
| ES (1) | ES431925A1 (en, 2012) |
| FR (1) | FR2250790A1 (en, 2012) |
| IN (1) | IN142632B (en, 2012) |
| IT (1) | IT1025597B (en, 2012) |
| MX (1) | MX151822A (en, 2012) |
| NL (1) | NL7414789A (en, 2012) |
| SE (1) | SE419971B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4165346A (en) * | 1976-11-26 | 1979-08-21 | Sun Oil Company Of Pennsylvania | Copolymer of poly(4,7-dioxadecamethylene adipamide)-polycaprolactam containing terephthalic acid |
| CA1099431A (en) * | 1976-11-26 | 1981-04-14 | Robert M. Thompson | Copolymer of poly (4,7-dioxadecamethylene adipamide) - polycaprolactam containing terephthalic acid |
| US4235714A (en) * | 1978-12-18 | 1980-11-25 | Suntech, Inc. | Hydrophilic polyamide film for semipermeable membranes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2339237A (en) * | 1941-04-11 | 1944-01-18 | Du Pont | Blended polyamides |
| US3397107A (en) * | 1965-07-22 | 1968-08-13 | Kanegafuchi Spinning Co Ltd | Composite polyamide filaments with improved potential crimpability and method of making the same |
| GB1169276A (en) * | 1966-03-15 | 1969-11-05 | Toyo Boseki | A process for the production of Polyamides having improved Hydrophylic Properties |
| DE1595758A1 (de) * | 1966-08-02 | 1970-02-12 | Glanzstoff Ag | Verfahren zur Herstellung von Polyamiden mit AEtherbindungen |
| US3729449A (en) * | 1969-08-27 | 1973-04-24 | Kanegafuchi Spinning Co Ltd | Polyamide fibers composed of the polyamide and methods for producing thereof |
-
1974
- 1974-11-01 IN IN2395/CAL/1974A patent/IN142632B/en unknown
- 1974-11-11 IT IT29306/74A patent/IT1025597B/it active
- 1974-11-12 JP JP12963574A patent/JPS5520490B2/ja not_active Expired
- 1974-11-13 DK DK590474A patent/DK590474A/da not_active Application Discontinuation
- 1974-11-13 NL NL7414789A patent/NL7414789A/xx not_active Application Discontinuation
- 1974-11-13 CA CA74213634A patent/CA1048682A/en not_active Expired
- 1974-11-14 DE DE2454142A patent/DE2454142C2/de not_active Expired
- 1974-11-14 SE SE7414344A patent/SE419971B/xx not_active IP Right Cessation
- 1974-11-14 FR FR7437527A patent/FR2250790A1/fr active Granted
- 1974-11-14 ES ES431925A patent/ES431925A1/es not_active Expired
- 1974-11-14 BE BE150478A patent/BE822168A/xx not_active IP Right Cessation
- 1974-11-14 MX MX154974A patent/MX151822A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5080395A (en, 2012) | 1975-06-30 |
| ES431925A1 (es) | 1977-01-16 |
| SE419971B (sv) | 1981-09-07 |
| JPS5520490B2 (en, 2012) | 1980-06-03 |
| DK590474A (en, 2012) | 1975-07-14 |
| IT1025597B (it) | 1978-08-30 |
| IN142632B (en, 2012) | 1977-08-06 |
| SE7414344L (en, 2012) | 1975-05-15 |
| DE2454142A1 (de) | 1975-05-15 |
| NL7414789A (nl) | 1975-05-16 |
| MX151822A (es) | 1985-03-29 |
| FR2250790A1 (en) | 1975-06-06 |
| BE822168A (fr) | 1975-05-14 |
| FR2250790B1 (en, 2012) | 1978-04-28 |
| DE2454142C2 (de) | 1985-02-07 |
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