DE1520301A1 - Verfahren zur Herstellung faser- oder fadenbildender synthetischer linearer Polycarbonamide - Google Patents
Verfahren zur Herstellung faser- oder fadenbildender synthetischer linearer PolycarbonamideInfo
- Publication number
- DE1520301A1 DE1520301A1 DE19631520301 DE1520301A DE1520301A1 DE 1520301 A1 DE1520301 A1 DE 1520301A1 DE 19631520301 DE19631520301 DE 19631520301 DE 1520301 A DE1520301 A DE 1520301A DE 1520301 A1 DE1520301 A1 DE 1520301A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- fiber
- polyamide
- saturated
- diamine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000000835 fiber Substances 0.000 title description 34
- 239000002253 acid Substances 0.000 claims description 24
- 150000004985 diamines Chemical class 0.000 claims description 14
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 13
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 5
- YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 description 26
- 229920002647 polyamide Polymers 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- -1 diamine salts Chemical class 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 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 5
- 238000009835 boiling Methods 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 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
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-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
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- YIXPUAYMZURQJH-GQCTYLIASA-N (e)-non-2-enedioic acid Chemical compound OC(=O)CCCCC\C=C\C(O)=O YIXPUAYMZURQJH-GQCTYLIASA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- BNTPVRGYUHJFHN-HWKANZROSA-N 2-Octenedioic acid Chemical compound OC(=O)CCCC\C=C\C(O)=O BNTPVRGYUHJFHN-HWKANZROSA-N 0.000 description 1
- GHYDCUFASUKRJZ-UHFFFAOYSA-N 3-ethylhex-2-enedioic acid Chemical compound C(C)C(=CC(=O)O)CCC(=O)O GHYDCUFASUKRJZ-UHFFFAOYSA-N 0.000 description 1
- GACSIVHAIFQKTC-UPHRSURJSA-N 4-Maleyl-acetoacetic acid Natural products OC(=O)CC(=O)CC(=O)\C=C/C(O)=O GACSIVHAIFQKTC-UPHRSURJSA-N 0.000 description 1
- XWLZJYOPKWHRDC-UHFFFAOYSA-N C(C)C(=CCCC(=O)O)C(=O)O Chemical compound C(C)C(=CCCC(=O)O)C(=O)O XWLZJYOPKWHRDC-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 235000019293 ammonium adipate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LQVYKEXVMZXOAH-UPHRSURJSA-N cis-4-Octenedioic acid Chemical compound OC(=O)CC\C=C/CCC(O)=O LQVYKEXVMZXOAH-UPHRSURJSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229920006240 drawn fiber Polymers 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- OXQWBLJQOBXJPM-UHFFFAOYSA-N hept-2-enedioic acid Chemical compound OC(=O)CCCC=CC(O)=O OXQWBLJQOBXJPM-UHFFFAOYSA-N 0.000 description 1
- KYVSJXHBUOEENN-UHFFFAOYSA-N hept-3-enedioic acid Chemical compound OC(=O)CCC=CCC(O)=O KYVSJXHBUOEENN-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 230000036964 tight binding Effects 0.000 description 1
- QWWZNXBOJLOHGI-HNQUOIGGSA-N trans-3-Octenedioic acid Chemical compound OC(=O)CCC\C=C\CC(O)=O QWWZNXBOJLOHGI-HNQUOIGGSA-N 0.000 description 1
- 239000006200 vaporizer Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US194731A US3240759A (en) | 1962-05-14 | 1962-05-14 | High shrinkage synthetic linear polycarbonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1520301A1 true DE1520301A1 (de) | 1969-02-20 |
Family
ID=22718710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631520301 Pending DE1520301A1 (de) | 1962-05-14 | 1963-05-10 | Verfahren zur Herstellung faser- oder fadenbildender synthetischer linearer Polycarbonamide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3240759A (en, 2012) |
| BE (1) | BE632305A (en, 2012) |
| CH (1) | CH424262A (en, 2012) |
| DE (1) | DE1520301A1 (en, 2012) |
| DK (1) | DK104434C (en, 2012) |
| FR (1) | FR1357279A (en, 2012) |
| GB (1) | GB979195A (en, 2012) |
| NL (2) | NL292720A (en, 2012) |
| SE (1) | SE304111B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4563507A (en) * | 1982-03-31 | 1986-01-07 | Intera Corporation | Treatment of Lewis base polymer with ethylenically unsaturated compound to improve antistatic hygroscopic and dye receptive properties |
| US10793673B2 (en) | 2015-11-10 | 2020-10-06 | Iowa State University Research Foundation, Inc. | Bioadvantaged nylon: polycondensation of 3-hexenedioic acid with hexamethylenediamine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174619A (en) * | 1936-09-22 | 1939-10-03 | Du Pont | Polyamides |
| US2149286A (en) * | 1937-01-13 | 1939-03-07 | Du Pont | Polyamides |
| US2243662A (en) * | 1938-07-25 | 1941-05-27 | Du Pont | Polymeric materials |
| US3081281A (en) * | 1959-10-16 | 1963-03-12 | Organico S A | Coloring of super polyamide resins |
-
0
- NL NL130567D patent/NL130567C/xx active
- BE BE632305D patent/BE632305A/xx unknown
- NL NL292720D patent/NL292720A/xx unknown
-
1962
- 1962-05-14 US US194731A patent/US3240759A/en not_active Expired - Lifetime
-
1963
- 1963-04-11 GB GB14626/63A patent/GB979195A/en not_active Expired
- 1963-05-06 CH CH568963A patent/CH424262A/fr unknown
- 1963-05-10 DE DE19631520301 patent/DE1520301A1/de active Pending
- 1963-05-10 FR FR934445A patent/FR1357279A/fr not_active Expired
- 1963-05-13 SE SE5267/63A patent/SE304111B/xx unknown
- 1963-05-13 DK DK225363AA patent/DK104434C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| FR1357279A (fr) | 1964-04-03 |
| CH424262A (fr) | 1966-11-15 |
| BE632305A (en, 2012) | |
| NL292720A (en, 2012) | |
| GB979195A (en) | 1965-01-01 |
| NL130567C (en, 2012) | |
| DK104434C (da) | 1966-05-16 |
| US3240759A (en) | 1966-03-15 |
| SE304111B (en, 2012) | 1968-09-16 |
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