DE1266977B - Verfahren zur Herstellung von linearen Polyamiden - Google Patents
Verfahren zur Herstellung von linearen PolyamidenInfo
- Publication number
- DE1266977B DE1266977B DEC22554A DEC0022554A DE1266977B DE 1266977 B DE1266977 B DE 1266977B DE C22554 A DEC22554 A DE C22554A DE C0022554 A DEC0022554 A DE C0022554A DE 1266977 B DE1266977 B DE 1266977B
- Authority
- DE
- Germany
- Prior art keywords
- polyamides
- forming
- acid
- amide
- polycondensation
- 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.)
- Ceased
Links
- 229920002647 polyamide Polymers 0.000 title claims description 26
- 239000004952 Polyamide Substances 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 239000000981 basic dye Substances 0.000 claims description 14
- 238000006068 polycondensation reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- QAMCXJOYXRSXDU-UHFFFAOYSA-N 2,4-dimethoxy-n-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline;chloride Chemical compound [Cl-].COC1=CC(OC)=CC=C1NC=CC1=[N+](C)C2=CC=CC=C2C1(C)C QAMCXJOYXRSXDU-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000835 fiber Substances 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000011591 potassium Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- -1 ethylene, propylene Chemical group 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- QNTADTGUHSAVOZ-UHFFFAOYSA-N 17-aminoheptadecanoic acid Chemical compound NCCCCCCCCCCCCCCCCC(O)=O QNTADTGUHSAVOZ-UHFFFAOYSA-N 0.000 description 1
- NUDXUJGIZOXHOV-UHFFFAOYSA-N 2,2-diphenylhexanedioic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(CCCC(=O)O)C1=CC=CC=C1 NUDXUJGIZOXHOV-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 1
- BTBJCTWMARHHQD-UHFFFAOYSA-N 2-heptadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O BTBJCTWMARHHQD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 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
- 230000003796 beauty Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- DVBBBJFTGOHNHC-UHFFFAOYSA-M potassium;3,5-dicarboxybenzenesulfonate Chemical compound [K+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 DVBBBJFTGOHNHC-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 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
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S264/00—Plastic and nonmetallic article shaping or treating: processes
- Y10S264/61—Processes of molding polyamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US847059A US3039990A (en) | 1959-10-19 | 1959-10-19 | Interpolyamides and process for preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1266977B true DE1266977B (de) | 1968-04-25 |
Family
ID=25299643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC22554A Ceased DE1266977B (de) | 1959-10-19 | 1960-10-18 | Verfahren zur Herstellung von linearen Polyamiden |
Country Status (6)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL256973A (US06653308-20031125-C00197.png) * | 1959-10-19 | |||
| US3288738A (en) * | 1960-06-07 | 1966-11-29 | Celanese Corp | Solution of polyhexamethylene terephthalamide in a solvent comprising formic acid and a compound selected from sulfuric acid, hydrogen chloride, and mixtures thereof |
| US3227792A (en) * | 1960-06-07 | 1966-01-04 | Celanese Corp | Solution spinning of polyhexamethylene terephthalamide |
| NL302928A (US06653308-20031125-C00197.png) * | 1963-01-03 | 1900-01-01 | ||
| US3402221A (en) * | 1963-10-29 | 1968-09-17 | Eastman Kodak Co | Poly (alpha-olefins) containing sulfated or sulfonated condensation polymers |
| DE1260684B (de) * | 1964-02-08 | 1968-02-08 | Bayer Ag | Verfahren zur Herstellung von Faeden und Fasern aus Polyamiden |
| DE1260683B (de) * | 1964-02-08 | 1968-02-08 | Bayer Ag | Verfahren zur Herstellung von Faeden und Fasern aus Polyamiden |
| DE1250964B (de) * | 1964-06-25 | 1967-09-28 | Farbenfabriken Bayer Aktiengesell schaft Leverkusen | Verfahren zum Herstellen von strukturgekrauselten Faden und Fasern aus Polyamiden |
| US3440226A (en) * | 1965-10-21 | 1969-04-22 | Ernestine H Huffman | Polycarbonamides resistant to acid dyes |
| US3438949A (en) * | 1965-10-21 | 1969-04-15 | Monsanto Co | Polycarbonamides resistant to acid dyes and containing terminal naphthyl disulfonated radicals |
| FR1510293A (US06653308-20031125-C00197.png) * | 1966-01-17 | 1968-04-03 | ||
| US3860560A (en) * | 1972-01-07 | 1975-01-14 | Fiber Industries Inc | Basic dyeable polyamides |
| US3846507A (en) * | 1972-04-06 | 1974-11-05 | Union Carbide Canada Ltd | Polyamide blends with one polyamide containing phthalate sulfonate moieties and terphthalate on isophthalate residues |
| US4303577A (en) * | 1978-12-01 | 1981-12-01 | Monsanto Company | Polyamide antiozonants |
| IT1109902B (it) * | 1979-01-05 | 1985-12-23 | Snia Viscosa | Procedimento per la produzione di poliammidi sintetiche,resistente alla fiamma,adatte alla filatura,e per la produzione di filamenti e fibre resistenti alla fiamma e prodottiottenuti con tale procedimento |
| IT1141254B (it) * | 1980-02-28 | 1986-10-01 | Montedison Spa | Procedimento per produrre poliammidi a modificata tingibilita' |
| US5164261A (en) * | 1990-08-08 | 1992-11-17 | E. I. Du Pont De Nemours And Company | Dyed antistain nylon with cationic dye modifier |
| US5242733A (en) * | 1990-08-08 | 1993-09-07 | E. I. Du Pont De Nemours And Company | Carpets and fabrics of antistain block copolymer compositions of modified nylon copolymers and high carbon nylons |
| 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 |
| US5223196A (en) * | 1990-11-20 | 1993-06-29 | E. I. Du Pont De Nemours And Company | Processing of pigmented nylon fibers using modified polymers |
| US6537475B1 (en) * | 1995-08-31 | 2003-03-25 | Prisma Fibers, Inc. | Melt extrusion spinning polyamide fibers with sulfonated reagent |
| US6433107B1 (en) | 1995-08-31 | 2002-08-13 | Prisma Fibers, Inc. | Fiber-forming polyamide with concentrate of polyamide and sulfonated aromatic acid |
| US5852087A (en) * | 1996-02-13 | 1998-12-22 | Teijin Limited | Easily dyeable meta-linkage-containing aromatic polyamide fibers |
| 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 |
| IL154571A0 (en) * | 2003-02-20 | 2003-09-17 | Nilit Ltd | Process for making polyamide textile articles bearing designs in different colors |
| JP2008522018A (ja) * | 2004-12-03 | 2008-06-26 | ウィリアム・マーシュ・ライス・ユニバーシティ | 界面重合によるよく分散されたポリマーナノコンポジット |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2880196A (en) * | 1955-06-10 | 1959-03-31 | Nat Distillers Chem Corp | Polyamides from diphenyladipic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1935264A (en) * | 1930-03-29 | 1933-11-14 | Firm Of Scoiety Of Chemical In | Esters of sulphonated aromatic carboxylic acids and peocess of making same |
| US2252554A (en) * | 1938-09-19 | 1941-08-12 | Wilmington Trust Company | Polymeric material |
| US2252555A (en) * | 1939-04-04 | 1941-08-12 | Wilmington Trust Co | Polymeric material |
| US2689864A (en) * | 1950-04-20 | 1954-09-21 | Monsasnto Chemical Company | Dicarboxylic sulfones |
-
0
- NL NL120504D patent/NL120504C/xx active
- NL NL256972D patent/NL256972A/xx unknown
-
1959
- 1959-10-19 US US847059A patent/US3039990A/en not_active Expired - Lifetime
-
1960
- 1960-10-11 GB GB34830/60A patent/GB901939A/en not_active Expired
- 1960-10-18 BE BE596144A patent/BE596144A/fr unknown
- 1960-10-18 CH CH1166260A patent/CH431070A/fr unknown
- 1960-10-18 DE DEC22554A patent/DE1266977B/de not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2880196A (en) * | 1955-06-10 | 1959-03-31 | Nat Distillers Chem Corp | Polyamides from diphenyladipic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| NL120504C (US06653308-20031125-C00197.png) | |
| CH431070A (fr) | 1967-02-28 |
| BE596144A (fr) | 1961-04-18 |
| US3039990A (en) | 1962-06-19 |
| GB901939A (en) | 1962-07-25 |
| NL256972A (US06653308-20031125-C00197.png) |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHV | Refusal |