CA2832178C - Elastomer fibers and methods of making and using thereof - Google Patents
Elastomer fibers and methods of making and using thereof Download PDFInfo
- Publication number
- CA2832178C CA2832178C CA2832178A CA2832178A CA2832178C CA 2832178 C CA2832178 C CA 2832178C CA 2832178 A CA2832178 A CA 2832178A CA 2832178 A CA2832178 A CA 2832178A CA 2832178 C CA2832178 C CA 2832178C
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- CA
- Canada
- Prior art keywords
- fiber
- fabric
- fibers
- prepared
- diisocyanate
- 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.)
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- 239000000835 fiber Substances 0.000 title claims abstract description 235
- 238000000034 method Methods 0.000 title claims abstract description 23
- 229920001971 elastomer Polymers 0.000 title claims description 30
- 239000000806 elastomer Substances 0.000 title claims description 30
- 239000004744 fabric Substances 0.000 claims abstract description 117
- 238000001816 cooling Methods 0.000 claims description 63
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 58
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- -1 alkylene glycol Chemical compound 0.000 claims description 36
- 229920005989 resin Polymers 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 36
- 239000004970 Chain extender Substances 0.000 claims description 32
- 230000000694 effects Effects 0.000 claims description 32
- 229920000728 polyester Polymers 0.000 claims description 30
- 125000005442 diisocyanate group Chemical group 0.000 claims description 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000004417 polycarbonate Substances 0.000 claims description 22
- 229920000515 polycarbonate Polymers 0.000 claims description 22
- 229920000570 polyether Polymers 0.000 claims description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000011256 inorganic filler Substances 0.000 claims description 14
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 14
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 229920002614 Polyether block amide Polymers 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002074 melt spinning Methods 0.000 claims description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
- 229920000297 Rayon Polymers 0.000 claims description 5
- 229920001778 nylon Polymers 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 239000002964 rayon Substances 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 3
- 229920002972 Acrylic fiber Polymers 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 70
- 239000000543 intermediate Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 19
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 18
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 18
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 18
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 229920002725 thermoplastic elastomer Polymers 0.000 description 14
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 12
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 12
- 230000035900 sweating Effects 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 239000001361 adipic acid Substances 0.000 description 9
- 235000011037 adipic acid Nutrition 0.000 description 9
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 150000002334 glycols Chemical class 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 229920002647 polyamide Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 210000004243 sweat Anatomy 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
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- 239000004615 ingredient Substances 0.000 description 3
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- 239000008188 pellet Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
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- 239000011787 zinc oxide Substances 0.000 description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
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- 229920000299 Nylon 12 Polymers 0.000 description 2
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- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
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- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
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- A—HUMAN NECESSITIES
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- A41B—SHIRTS; UNDERWEAR; BABY LINEN; HANDKERCHIEFS
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- A—HUMAN NECESSITIES
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- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D31/00—Materials specially adapted for outerwear
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- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D31/00—Materials specially adapted for outerwear
- A41D31/04—Materials specially adapted for outerwear characterised by special function or use
- A41D31/18—Elastic
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
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- D—TEXTILES; PAPER
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- 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
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- D—TEXTILES; PAPER
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- 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
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- D—TEXTILES; PAPER
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- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
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- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
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Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Artificial Filaments (AREA)
- Polyurethanes Or Polyureas (AREA)
- Undergarments, Swaddling Clothes, Handkerchiefs Or Underwear Materials (AREA)
- Knitting Of Fabric (AREA)
- Woven Fabrics (AREA)
- Professional, Industrial, Or Sporting Protective Garments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161475727P | 2011-04-15 | 2011-04-15 | |
| US61/475,727 | 2011-04-15 | ||
| PCT/US2012/032861 WO2012154364A1 (en) | 2011-04-15 | 2012-04-10 | Elastomer fibers and methods of making and using thereof |
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| KR101341055B1 (ko) * | 2012-12-26 | 2013-12-13 | 박희대 | 열가소성 폴리우레탄 원사의 조성물 및 그 제조방법 |
| US9936751B1 (en) | 2013-03-14 | 2018-04-10 | Francesco Mignone | Towel/absorptive arm sleeve and means of hands free toweling |
| AU2017229328B2 (en) * | 2016-03-08 | 2019-05-16 | KOB GmbH | Sock |
| US10337128B2 (en) * | 2017-08-31 | 2019-07-02 | Brrr! Inc. | Methods and compositions for cooling yarns and fabrics, and articles comprising same |
| US10557219B1 (en) * | 2018-12-28 | 2020-02-11 | Brrr! Inc. | Methods and compositions for cooling yarns and fabrics comprising a cellulosic fiber, and articles comprising same |
| KR102459780B1 (ko) * | 2020-06-30 | 2022-10-28 | (주)메디코어 | 비강용 스펀지형 창상피복재 및 그 제조방법 |
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| US4131731A (en) | 1976-11-08 | 1978-12-26 | Beatrice Foods Company | Process for preparing polycarbonates |
| JPH02169713A (ja) * | 1988-10-26 | 1990-06-29 | Mitsubishi Heavy Ind Ltd | 形状記憶性ポリマー糸 |
| US5167899A (en) * | 1990-07-07 | 1992-12-01 | The Dow Chemical Company | Process for melt blowing microfibers of rigid polyurethane having hard segments |
| JP2000144532A (ja) * | 1998-11-05 | 2000-05-26 | Okada Engineering:Kk | 吸水性ポリウレタン繊維の製造方法 |
| JP2003155669A (ja) | 2001-11-19 | 2003-05-30 | Sakai Ovex Co Ltd | 清涼感を有する布 |
| US20040087739A1 (en) * | 2002-10-30 | 2004-05-06 | Kemal Onder | Monolithic thermoplastic ether polyurethane having high water vapor transmission |
| US7202322B2 (en) * | 2002-11-08 | 2007-04-10 | Noveon, Inc. | Heat resistant high moisture vapor transmission thermoplastic polyurethane |
| US7294593B2 (en) * | 2002-11-21 | 2007-11-13 | Kimberly-Clark Worldwide, Inc. | Absorbent article material with elastomeric borders |
| WO2004053218A1 (ja) * | 2002-12-12 | 2004-06-24 | Nisshinbo Industries, Inc. | ポリウレタン弾性繊維混用織編物及びその製造方法 |
| US7799255B2 (en) * | 2003-06-30 | 2010-09-21 | Lubrizol Advanced Materials, Inc. | Melt spun elastic tape and process |
| JP4860261B2 (ja) * | 2005-12-27 | 2012-01-25 | 旭化成せんい株式会社 | ポリウレタン弾性繊維 |
| TWM328457U (en) * | 2007-01-29 | 2008-03-11 | guo-bin Zheng | Fiber products having multi-function thermal diffusive and cooling performances |
| US20090093606A1 (en) * | 2007-10-09 | 2009-04-09 | The Hong Kong Polytechnic University | Shape memory fibers prepared via wet, reaction, dry, melt, and electro spinning |
| JP5751832B2 (ja) * | 2007-10-22 | 2015-07-22 | ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド | 軟質で弾性の可塑剤非含有熱可塑性ポリウレタンおよびそれを合成するプロセス |
| CN102046870A (zh) * | 2008-05-29 | 2011-05-04 | 三井化学株式会社 | 混纤纺粘非织造布及其用途 |
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| TW201739974A (zh) | 2017-11-16 |
| CA2832178A1 (en) | 2012-11-15 |
| MY164541A (en) | 2018-01-15 |
| EP2697415B1 (en) | 2016-06-08 |
| US20170127741A1 (en) | 2017-05-11 |
| MX353977B (es) | 2018-02-07 |
| AU2012254081A1 (en) | 2013-10-24 |
| SG194055A1 (en) | 2013-11-29 |
| MX2013011848A (es) | 2013-11-01 |
| WO2012154364A1 (en) | 2012-11-15 |
| AU2017201642A1 (en) | 2017-03-30 |
| KR101928053B1 (ko) | 2018-12-11 |
| EP2697415A1 (en) | 2014-02-19 |
| TWI628327B (zh) | 2018-07-01 |
| JP6173299B2 (ja) | 2017-08-02 |
| TW201247952A (en) | 2012-12-01 |
| KR20140023363A (ko) | 2014-02-26 |
| BR112013026090A2 (pt) | 2019-12-31 |
| CN103547716B (zh) | 2016-11-16 |
| JP2014511949A (ja) | 2014-05-19 |
| CN103547716A (zh) | 2014-01-29 |
| ES2577980T3 (es) | 2016-07-19 |
| US20140101825A1 (en) | 2014-04-17 |
| BR112013026090B1 (pt) | 2020-08-18 |
| TWI643987B (zh) | 2018-12-11 |
| JP2017101373A (ja) | 2017-06-08 |
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