CA2787938A1 - Bio-based terpolymers and process of making the same - Google Patents
Bio-based terpolymers and process of making the same Download PDFInfo
- Publication number
- CA2787938A1 CA2787938A1 CA 2787938 CA2787938A CA2787938A1 CA 2787938 A1 CA2787938 A1 CA 2787938A1 CA 2787938 CA2787938 CA 2787938 CA 2787938 A CA2787938 A CA 2787938A CA 2787938 A1 CA2787938 A1 CA 2787938A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- terpolymer
- weight percentage
- constituent unit
- fiber
- 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
- 229920001897 terpolymer Polymers 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title claims abstract description 25
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 44
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 44
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 22
- 239000001361 adipic acid Substances 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000000835 fiber Substances 0.000 claims description 65
- 239000000470 constituent Substances 0.000 claims description 50
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 26
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 229920001169 thermoplastic Polymers 0.000 claims description 19
- 239000004416 thermosoftening plastic Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 16
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 16
- -1 polyethylene terephthalate Polymers 0.000 claims description 13
- 239000004408 titanium dioxide Substances 0.000 claims description 11
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000004599 antimicrobial Substances 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 235000006708 antioxidants Nutrition 0.000 claims description 9
- 239000003086 colorant Substances 0.000 claims description 9
- 239000003063 flame retardant Substances 0.000 claims description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 9
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 9
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 239000000543 intermediate Substances 0.000 claims description 7
- 230000003750 conditioning effect Effects 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 abstract description 8
- 229920002647 polyamide Polymers 0.000 abstract description 8
- 229920006021 bio-based polyamide Polymers 0.000 abstract description 3
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 15
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 12
- 229920001778 nylon Polymers 0.000 description 10
- 239000000975 dye Substances 0.000 description 8
- 239000004677 Nylon Substances 0.000 description 7
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229920000305 Nylon 6,10 Polymers 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229920013724 bio-based polymer Polymers 0.000 description 6
- 239000001272 nitrous oxide Substances 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 239000000980 acid dye Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 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 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000009408 flooring Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004784 Superba Substances 0.000 description 1
- 241000324401 Superba Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
- C08G69/30—Solid state polycondensation
-
- 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
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/80—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N7/00—Flexible sheet materials not otherwise provided for, e.g. textile threads, filaments, yarns or tow, glued on macromolecular material
- D06N7/0063—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf
- D06N7/0065—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf characterised by the pile
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N7/00—Flexible sheet materials not otherwise provided for, e.g. textile threads, filaments, yarns or tow, glued on macromolecular material
- D06N7/0063—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf
- D06N7/0068—Floor covering on textile basis comprising a fibrous top layer being coated at the back with at least one polymer layer, e.g. carpets, rugs, synthetic turf characterised by the primary backing or the fibrous top layer
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N2201/00—Chemical constitution of the fibres, threads or yarns
- D06N2201/02—Synthetic macromolecular fibres
- D06N2201/0263—Polyamide fibres
-
- 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
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/23993—Composition of pile or adhesive
-
- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Woven Fabrics (AREA)
- Carpets (AREA)
- Knitting Of Fabric (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30030810P | 2010-02-01 | 2010-02-01 | |
| US61/300,308 | 2010-02-01 | ||
| PCT/US2011/023147 WO2011094673A2 (en) | 2010-02-01 | 2011-01-31 | Bio-based terpolymers and process of making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2787938A1 true CA2787938A1 (en) | 2011-08-04 |
Family
ID=44320192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2787938 Abandoned CA2787938A1 (en) | 2010-02-01 | 2011-01-31 | Bio-based terpolymers and process of making the same |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20120301659A1 (enExample) |
| EP (1) | EP2531545A4 (enExample) |
| JP (1) | JP2013518940A (enExample) |
| CN (1) | CN103097434B (enExample) |
| AU (1) | AU2011210623B2 (enExample) |
| CA (1) | CA2787938A1 (enExample) |
| WO (1) | WO2011094673A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202012103846U1 (de) | 2012-10-08 | 2012-10-25 | Heimbach Gmbh & Co. Kg | Papiermaschinenband |
| CN103030803B (zh) * | 2012-12-23 | 2014-11-26 | 北京化工大学 | 一种生物基聚酰胺四元共聚物及其合成方法 |
| JP2018529834A (ja) * | 2015-09-29 | 2018-10-11 | アセンド・パフォーマンス・マテリアルズ・オペレーションズ・リミテッド・ライアビリティ・カンパニーＡｓｃｅｎｄ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｏｐｅｒａｔｉｏｎｓ Ｌｌｃ | 結晶化速度を低下させたコポリアミド組成物 |
| US10793673B2 (en) | 2015-11-10 | 2020-10-06 | Iowa State University Research Foundation, Inc. | Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine |
| CN108102090A (zh) * | 2016-11-24 | 2018-06-01 | 上海杰事杰新材料(集团)股份有限公司 | 超韧热稳定聚酰胺树脂及其制备方法 |
| CN110240698A (zh) * | 2019-06-28 | 2019-09-17 | 山东东辰瑞森新材料科技有限公司 | 一种高温尼龙pa6t共聚物的制备方法 |
| EP4118133A1 (en) * | 2020-03-13 | 2023-01-18 | INVISTA Textiles (U.K.) Limited | Thermoplastic resins for network applications |
| CN111549423A (zh) * | 2020-03-23 | 2020-08-18 | 合肥利夫生物科技有限公司 | 一种生物基阻燃材料 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA577282A (en) * | 1959-06-09 | Costain Winston | Interpolyamides from hexamethylene diamine and adipic-sebacic acids | |
| US2865894A (en) * | 1955-06-15 | 1958-12-23 | Nat Distillers Chem Corp | Polyamides from dicyclohexyladipic acid |
| US3399108A (en) * | 1965-06-18 | 1968-08-27 | Du Pont | Crimpable, composite nylon filament and fabric knitted therefrom |
| NL169204C (nl) * | 1968-11-25 | 1982-06-16 | Rhone Poulenc Textile | Werkwijze voor het vervaardigen van een bicomponentdraad. |
| JPS5119043B2 (enExample) * | 1972-07-27 | 1976-06-15 | ||
| US4076664A (en) * | 1975-11-13 | 1978-02-28 | E. I. Du Pont De Nemours And Company | 612 OR 610/6I or 6T/636 Polyamide terpolymer |
| US4719060A (en) | 1986-07-17 | 1988-01-12 | E. I. Du Pont De Nemours And Company | Method of predicting yarn properties |
| US4992515A (en) * | 1990-01-09 | 1991-02-12 | Shakespeare Company | Nylon terpolymer crosslinked with melamine formaldehyde for coating sewing threads |
| DE69124624T2 (de) * | 1990-11-20 | 1997-09-04 | E.I. Du Pont De Nemours & Co., Wilmington, Del. | Amideinheiten aus 2-methylpentamethylendiamine enthaltende terpolyamide und multipolyamide und daraus hergestellte produkte |
| US5763095A (en) * | 1995-11-29 | 1998-06-09 | W. R. Grace & Co.-Conn. | Breathable film for cheese packaging |
| JPH115839A (ja) * | 1997-06-17 | 1999-01-12 | Toray Ind Inc | 繊維用ポリアミドおよびそれを用いてなる繊維ならびに着色繊維の製造方法 |
| JP2000053763A (ja) * | 1998-08-11 | 2000-02-22 | Toray Ind Inc | 共重合ポリアミド、その製造方法およびその用途 |
| JP2002054025A (ja) * | 2000-05-24 | 2002-02-19 | Toray Ind Inc | 繊維用ポリアミド樹脂組成物ならびにポリアミド繊維 |
| US6930150B2 (en) * | 2002-08-29 | 2005-08-16 | Taylor Made Golf Company, Inc. | Method for making polymer mixtures and compositions thereof |
| KR20080080132A (ko) * | 2005-11-23 | 2008-09-02 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 탄소 섬유로 강화된 폴리아미드 수지 조성물 |
| CN101970108B (zh) * | 2008-02-11 | 2013-07-10 | 巴斯夫欧洲公司 | 聚酰胺的制备 |
-
2011
- 2011-01-31 EP EP11737809.1A patent/EP2531545A4/en not_active Withdrawn
- 2011-01-31 AU AU2011210623A patent/AU2011210623B2/en not_active Ceased
- 2011-01-31 WO PCT/US2011/023147 patent/WO2011094673A2/en not_active Ceased
- 2011-01-31 JP JP2012551364A patent/JP2013518940A/ja active Pending
- 2011-01-31 CN CN201180016672.6A patent/CN103097434B/zh not_active Expired - Fee Related
- 2011-01-31 CA CA 2787938 patent/CA2787938A1/en not_active Abandoned
- 2011-01-31 US US13/576,256 patent/US20120301659A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011094673A3 (en) | 2012-01-12 |
| AU2011210623A1 (en) | 2012-08-09 |
| EP2531545A2 (en) | 2012-12-12 |
| AU2011210623B2 (en) | 2015-06-25 |
| CN103097434A (zh) | 2013-05-08 |
| US20120301659A1 (en) | 2012-11-29 |
| WO2011094673A2 (en) | 2011-08-04 |
| JP2013518940A (ja) | 2013-05-23 |
| EP2531545A4 (en) | 2013-10-02 |
| CN103097434B (zh) | 2015-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160122 |
|
| FZDE | Discontinued |
Effective date: 20180608 |