CA2949532A1 - Polymers with modified surface properties and method of making the same - Google Patents
Polymers with modified surface properties and method of making the same Download PDFInfo
- Publication number
- CA2949532A1 CA2949532A1 CA2949532A CA2949532A CA2949532A1 CA 2949532 A1 CA2949532 A1 CA 2949532A1 CA 2949532 A CA2949532 A CA 2949532A CA 2949532 A CA2949532 A CA 2949532A CA 2949532 A1 CA2949532 A1 CA 2949532A1
- Authority
- CA
- Canada
- Prior art keywords
- fiber
- additive
- thermoplastic
- thermoplastic fiber
- reactive
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 229920000642 polymer Polymers 0.000 title claims description 50
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- 239000000654 additive Substances 0.000 claims abstract description 105
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 105
- 230000000996 additive effect Effects 0.000 claims abstract description 94
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- 238000000034 method Methods 0.000 claims abstract description 34
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 69
- 239000000975 dye Substances 0.000 claims description 46
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 19
- -1 polyethylene Polymers 0.000 claims description 15
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- 229920002647 polyamide Polymers 0.000 claims description 13
- 239000004952 Polyamide Substances 0.000 claims description 12
- 230000002708 enhancing effect Effects 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 238000012360 testing method Methods 0.000 description 12
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YOCIQNIEQYCORH-UHFFFAOYSA-M chembl2028361 Chemical compound [Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=CC=C1 YOCIQNIEQYCORH-UHFFFAOYSA-M 0.000 description 6
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- XWZDJOJCYUSIEY-YOYNBWDYSA-L procion red MX-5B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=CC(NC=3N=C(Cl)N=C(Cl)N=3)=C2C(O)=C1\N=N\C1=CC=CC=C1 XWZDJOJCYUSIEY-YOYNBWDYSA-L 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
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- 125000000129 anionic group Chemical group 0.000 description 3
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- INOIOAWTVPHTCJ-UHFFFAOYSA-N 6-acetamido-4-hydroxy-3-[[4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2-sulfonic acid Chemical compound CC(=O)NC1=CC=C2C=C(C(N=NC3=CC=C(C=C3)S(=O)(=O)CCOS(O)(=O)=O)=C(O)C2=C1)S(O)(=O)=O INOIOAWTVPHTCJ-UHFFFAOYSA-N 0.000 description 2
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- FBPFZTCFMRRESA-KAZBKCHUSA-N D-altritol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000004957 Zytel Substances 0.000 description 2
- 229920006102 Zytel® Polymers 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 238000011021 bench scale process Methods 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
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- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 239000004615 ingredient Substances 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
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- 229920000307 polymer substrate Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- DHHGSXPASZBLGC-VPMNAVQSSA-L remazole orange-3R Chemical compound [Na+].[Na+].OC=1C2=CC(NC(=O)C)=CC=C2C=C(S([O-])(=O)=O)C=1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 DHHGSXPASZBLGC-VPMNAVQSSA-L 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
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- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 1
- WXSVCGWHWWPQKF-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)cyclohexan-1-ol Chemical compound OCCC1CCCC(O)C1CCO WXSVCGWHWWPQKF-UHFFFAOYSA-N 0.000 description 1
- PLPYCSBZHKTQPB-UHFFFAOYSA-N 2-(2-hydroxyethoxy)hexane-1,2-diol Chemical compound CCCCC(O)(CO)OCCO PLPYCSBZHKTQPB-UHFFFAOYSA-N 0.000 description 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- YHXNHYKKDRMEEH-UHFFFAOYSA-N 3-(2-hydroxyethoxy)propane-1,2-diol Chemical compound OCCOCC(O)CO YHXNHYKKDRMEEH-UHFFFAOYSA-N 0.000 description 1
- WQYPVEKEHDLOBS-UHFFFAOYSA-N 3-(2-hydroxypropoxy)propane-1,2-diol Chemical compound CC(O)COCC(O)CO WQYPVEKEHDLOBS-UHFFFAOYSA-N 0.000 description 1
- KQXMFSOXJUGYBW-UHFFFAOYSA-N 3-[4,4-bis(2,3-dihydroxyphenyl)butyl]benzene-1,2-diol Chemical compound OC1=CC=CC(CCCC(C=2C(=C(O)C=CC=2)O)C=2C(=C(O)C=CC=2)O)=C1O KQXMFSOXJUGYBW-UHFFFAOYSA-N 0.000 description 1
- NOEIYOLYKBVGGI-UHFFFAOYSA-N 4-[3,3-bis(2,4-dihydroxy-3-methylphenyl)propyl]-2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC(CCC(C=2C(=C(C)C(O)=CC=2)O)C=2C(=C(C)C(O)=CC=2)O)=C1O NOEIYOLYKBVGGI-UHFFFAOYSA-N 0.000 description 1
- RAEZDADOWHBDJK-UHFFFAOYSA-N 6-(2-hydroxypropoxy)hexane-1,2-diol Chemical compound CC(O)COCCCCC(O)CO RAEZDADOWHBDJK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
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- 238000004566 IR spectroscopy Methods 0.000 description 1
- HEBKCHPVOIAQTA-IMJSIDKUSA-N L-arabinitol Chemical compound OC[C@H](O)C(O)[C@@H](O)CO HEBKCHPVOIAQTA-IMJSIDKUSA-N 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000321453 Paranthias colonus Species 0.000 description 1
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- 229910000831 Steel Inorganic materials 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
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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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- 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
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462001853P | 2014-05-22 | 2014-05-22 | |
| US62/001,853 | 2014-05-22 | ||
| PCT/US2015/031935 WO2015179616A1 (en) | 2014-05-22 | 2015-05-21 | Polymers with modified surface properties and method of making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2949532A1 true CA2949532A1 (en) | 2015-11-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2949532A Abandoned CA2949532A1 (en) | 2014-05-22 | 2015-05-21 | Polymers with modified surface properties and method of making the same |
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| Country | Link |
|---|---|
| EP (1) | EP3145996A4 (ja) |
| JP (1) | JP6839983B2 (ja) |
| CN (1) | CN107001792A (ja) |
| AU (1) | AU2015264103B2 (ja) |
| CA (1) | CA2949532A1 (ja) |
| WO (1) | WO2015179616A1 (ja) |
Families Citing this family (1)
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| CN110387597B (zh) * | 2019-06-19 | 2021-10-26 | 东华大学 | 一种基于一步法牵伸工艺的高强尼龙6长丝及其制备方法 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3236685A (en) * | 1962-06-20 | 1966-02-22 | Eastman Kodak Co | Process for treating textile fibers and other shaped products with coatings |
| JPS5879052A (ja) * | 1981-11-05 | 1983-05-12 | Unitika Ltd | 耐久性の優れたポリアミド樹脂及び成形品 |
| DE3673008D1 (de) * | 1983-12-16 | 1990-08-30 | Monsanto Co | Fleckenabweisende nylonteppiche. |
| ATE67799T1 (de) | 1985-04-22 | 1991-10-15 | Basf Corp | Verfahren zum schnellspinnen von polyamidfasern. |
| DE3711318A1 (de) * | 1987-04-03 | 1988-10-20 | Basf Ag | Verwendung von pfropfpolymerisaten auf basis von polyalkylenoxiden als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
| US5155178A (en) | 1990-08-08 | 1992-10-13 | E. I. Du Pont De Nemours And Company | Antistain block copolymer compositions of modified nylon copolymers and high carbon nylons |
| US5272246A (en) | 1990-08-28 | 1993-12-21 | Hoechst Celanese Corporation | Polyester copolymer fiber having enhanced strength and dyeability properties |
| US5135697A (en) | 1990-08-28 | 1992-08-04 | Hoescht Celanese Corporation | Polyester copolymer fiber having enhanced strength and dyeability properties |
| GB9122318D0 (en) | 1991-10-21 | 1991-12-04 | Courtaulds Plc | Treatment of elongate members |
| US5897952A (en) * | 1992-04-03 | 1999-04-27 | The United States Of America As Represented By The Secretary Of Agriculture | Temperature adaptable glyoxal-modified fibers and method of preparing same |
| DE4309436A1 (de) * | 1993-03-24 | 1994-09-29 | Sandoz Ag | Sauer modifizierte synthetishe Polyamide |
| EP0639664A1 (en) * | 1993-08-16 | 1995-02-22 | Basf Corporation | Nylon fibers with improved dye washfastness and heat stability |
| CA2122210C (en) | 1993-08-16 | 2000-02-15 | Anil W. Saraf | Process for the manufacture of a post-heat set dyed fabric consisting essentially of polyamide fibers with improved dye washfastness and heat stability |
| US6433107B1 (en) * | 1995-08-31 | 2002-08-13 | Prisma Fibers, Inc. | Fiber-forming polyamide with concentrate of polyamide and sulfonated aromatic acid |
| US6537475B1 (en) * | 1995-08-31 | 2003-03-25 | Prisma Fibers, Inc. | Melt extrusion spinning polyamide fibers with sulfonated reagent |
| JP2000506230A (ja) | 1996-03-07 | 2000-05-23 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 高防汚性を備えたカーペットヤーン |
| US6117550A (en) | 1997-10-22 | 2000-09-12 | Prisma Fibers, Inc. | Acid dye stain-resistant fiber-forming polyamide composition containing masterbatch concentrate containing reagent and carrier |
| US6623853B2 (en) | 1998-08-28 | 2003-09-23 | Wellman, Inc. | Polyethylene glycol modified polyester fibers and method for making the same |
| TW467982B (en) * | 1999-06-28 | 2001-12-11 | Ind Tech Res Inst | Method to modify fiber surface |
| US6284864B1 (en) | 2000-05-31 | 2001-09-04 | Arteva North America S.A.R.L. | Permanent deep-dye polyester |
| WO2007036929A2 (en) | 2005-09-29 | 2007-04-05 | Nilit Ltd. | Modified polyamides, uses thereof and process for their preparation |
| AU2010289583A1 (en) | 2009-09-02 | 2012-03-15 | E. I. Du Pont De Nemours And Company | Polyesters comprising fluorovinylether functionalized aromatic moieties |
| US8697831B2 (en) | 2011-06-22 | 2014-04-15 | E I Du Pont De Nemours And Company | Process for preparing polyamides comprising fluoroether functionalized aromatic moieties |
| US8247519B1 (en) | 2011-06-22 | 2012-08-21 | E I Du Pont De Nemours And Company | Shaped articles fabricated from polyamides comprising fluoroether functionalized aromatic moieties |
| WO2013033287A2 (en) * | 2011-08-31 | 2013-03-07 | Invista Technologies S.A R.L. | Compositions of polyhydric alcohols and polyamides |
| BR112015021794B1 (pt) * | 2013-03-09 | 2022-05-03 | Donaldson Company, Inc | Método de fabricação de fibras finas, meio de filtragem e elemento de filtragem |
| US20140288220A1 (en) * | 2013-03-25 | 2014-09-25 | E I Du Pont De Nemours And Company | Heat resistant polyamide compositions |
| CN103757731B (zh) * | 2013-12-11 | 2016-03-02 | 巢湖亚塑网具制造有限公司 | 一种耐酸碱渔网 |
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2015
- 2015-05-21 EP EP15795331.6A patent/EP3145996A4/en not_active Withdrawn
- 2015-05-21 CN CN201580039911.8A patent/CN107001792A/zh active Pending
- 2015-05-21 JP JP2016568927A patent/JP6839983B2/ja active Active
- 2015-05-21 CA CA2949532A patent/CA2949532A1/en not_active Abandoned
- 2015-05-21 WO PCT/US2015/031935 patent/WO2015179616A1/en active Application Filing
- 2015-05-21 AU AU2015264103A patent/AU2015264103B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015179616A1 (en) | 2015-11-26 |
| CN107001792A (zh) | 2017-08-01 |
| EP3145996A1 (en) | 2017-03-29 |
| JP2017518445A (ja) | 2017-07-06 |
| AU2015264103A1 (en) | 2016-12-08 |
| JP6839983B2 (ja) | 2021-03-10 |
| AU2015264103B2 (en) | 2019-02-07 |
| EP3145996A4 (en) | 2018-01-10 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20200520 |
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| FZDE | Discontinued |
Effective date: 20221018 |
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| FZDE | Discontinued |
Effective date: 20221018 |