DE749747C - Verfahren zur Herstellung hochkondensierter Polyamide aus Diaminen und Dicarbonsaeuren - Google Patents
Verfahren zur Herstellung hochkondensierter Polyamide aus Diaminen und DicarbonsaeurenInfo
- Publication number
- DE749747C DE749747C DEP71282D DEP0071282D DE749747C DE 749747 C DE749747 C DE 749747C DE P71282 D DEP71282 D DE P71282D DE P0071282 D DEP0071282 D DE P0071282D DE 749747 C DE749747 C DE 749747C
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- acid
- diamines
- dicarboxylic acids
- amide
- 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.)
- Expired
Links
- 239000004952 Polyamide Substances 0.000 title claims description 21
- 229920002647 polyamide Polymers 0.000 title claims description 21
- 150000004985 diamines Chemical class 0.000 title claims description 18
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000005336 cracking Methods 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 32
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- -1 compound salt Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 3
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 3
- 150000003739 xylenols Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-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
- 229920000728 polyester Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-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
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- RJOCMAMQRDKZGL-UHFFFAOYSA-N bis(3-methylphenyl) octadecanedioate Chemical compound C(CCCCCCCCCCCCCCCCC(=O)OC1=CC(=CC=C1)C)(=O)OC1=CC(=CC=C1)C RJOCMAMQRDKZGL-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- LGGDSXPOQVDFDO-UHFFFAOYSA-N diethyl octadecanedioate Chemical compound CCOC(=O)CCCCCCCCCCCCCCCCC(=O)OCC LGGDSXPOQVDFDO-UHFFFAOYSA-N 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- ODVYFOLTLWONHF-UHFFFAOYSA-N diphenyl decanedioate Chemical compound C=1C=CC=CC=1OC(=O)CCCCCCCCC(=O)OC1=CC=CC=C1 ODVYFOLTLWONHF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- RLNAIWYXIAJDTN-UHFFFAOYSA-N hydron;pentane-1,5-diamine;chloride Chemical compound Cl.NCCCCCN RLNAIWYXIAJDTN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
-
- 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
-
- 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
- C08G69/04—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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201945XA | 1935-01-02 | 1935-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE749747C true DE749747C (de) | 1944-12-05 |
Family
ID=21797250
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP71282D Expired DE749747C (de) | 1935-01-02 | 1935-05-18 | Verfahren zur Herstellung hochkondensierter Polyamide aus Diaminen und Dicarbonsaeuren |
| DEP75794A Expired DE740348C (de) | 1935-01-02 | 1937-08-25 | Verfahren zur Herstellung geformter Gebilde durch Auspressen |
| DEP79822D Expired DE745029C (de) | 1935-01-02 | 1939-09-27 | Verfahren zur Herstellung von hoehermolekularen Superpolyamiden |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP75794A Expired DE740348C (de) | 1935-01-02 | 1937-08-25 | Verfahren zur Herstellung geformter Gebilde durch Auspressen |
| DEP79822D Expired DE745029C (de) | 1935-01-02 | 1939-09-27 | Verfahren zur Herstellung von hoehermolekularen Superpolyamiden |
Country Status (5)
| Country | Link |
|---|---|
| BE (2) | BE416730A (enrdf_load_stackoverflow) |
| DE (3) | DE749747C (enrdf_load_stackoverflow) |
| FR (5) | FR790521A (enrdf_load_stackoverflow) |
| GB (4) | GB461237A (enrdf_load_stackoverflow) |
| NL (1) | NL52489C (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1024234B (de) * | 1953-09-29 | 1958-02-13 | California Research Corp | Verfahren zur Herstellung von linearen Polyamiden aus Diaminen und aliphatischen Dicarbonsaeuren |
| DE1040785B (de) * | 1953-06-04 | 1958-10-09 | California Research Corp | Verfahren zur Herstellung von Polyamiden |
| DE1211390B (de) * | 1957-08-28 | 1966-02-24 | Perfogit Societa Per Azioni | Verfahren zur Polykondensation von aus Diaminen und Dicarbonsaeuren gebildeten Salzen |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2963465A (en) * | 1960-12-06 | Certification of correction | ||
| US2212772A (en) * | 1937-02-15 | 1940-08-27 | Du Pont | Synthetic polymers and shaped articles therefrom |
| DE748253C (de) * | 1938-06-10 | 1944-10-30 | Verfahren zur Herstellung verformbarer hochmolekularer Polyamide | |
| US2253176A (en) * | 1938-08-09 | 1941-08-19 | Du Pont | Method and apparatus for production of structures |
| DE976142C (de) * | 1938-09-01 | 1963-03-28 | Aeg | Verwendung von Phenolharz-Polyamidgemischen zur elektrischen Isolation |
| NL52648C (enrdf_load_stackoverflow) * | 1938-09-29 | 1900-01-01 | ||
| US2241323A (en) * | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides |
| US2273200A (en) * | 1938-11-01 | 1942-02-17 | Du Pont | Artificial structure |
| DE902090C (de) * | 1939-01-11 | 1954-01-18 | Basf Ag | Verfahren zur Herstellung von Kondensationsprodukten |
| DE755428C (de) * | 1939-02-07 | 1953-05-04 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von schmelzbaren, hochpolymeren, linearen Polyamiden |
| DE748023C (de) * | 1939-03-17 | 1944-10-25 | Verfahren zur Herstellung von hochpolymeren Polyamiden oder Mischpolyamiden (Superpolyamiden) | |
| NL56652C (enrdf_load_stackoverflow) * | 1940-03-09 | |||
| DE976561C (de) * | 1940-05-02 | 1963-11-14 | Aeg | UEberzugsmasse |
| DE766183C (de) * | 1940-09-03 | 1953-12-07 | Ig Farbenindustrie Ag | Weichmacher fuer Superpolyamide |
| DE932581C (de) * | 1942-10-31 | 1955-09-05 | Zellwolle Und Kunstseide Ring | Verfahren zur Herstellung von hochmolekularen Polykondensationsprodukten |
| DE975586C (de) * | 1943-01-29 | 1962-02-01 | Hackethal Draht Und Kabel Werk | Verfahren zur Herstellung von elektrischen Leitern mit einer biegsamen Isolierung aus thermoplastischen Kunststoffen |
| US2647146A (en) * | 1949-07-01 | 1953-07-28 | Du Pont | Process for the preparation of diprimary diamines |
| US2816879A (en) * | 1951-11-15 | 1957-12-17 | Du Pont | Process for preparing polyureas utilizing immiscible phases |
| DE974334C (de) * | 1952-04-21 | 1960-11-24 | Glanzstoff Ag | Verfahren zur Herstellung von Faeden, Fasern, Borsten und Filmen aus linearen aromatischen Polyestern nach dem Schmelzspinnverfahren |
| US2835654A (en) * | 1954-10-11 | 1958-05-20 | Du Pont | Process for making elastomers from polymeric bis-chloroformates, phosgene and diamines |
| FR1157919A (fr) * | 1955-09-27 | 1958-06-05 | Du Pont | Procédé de fabrication d'articles moulés, améliorés, en polyamide |
| NL106791C (enrdf_load_stackoverflow) * | 1956-09-21 | |||
| US3074914A (en) * | 1957-04-04 | 1963-01-22 | Dow Chemical Co | Cyclobutane derivative polymers |
| DE1202487B (de) * | 1958-03-26 | 1965-10-07 | Minnesota Mining & Mfg | Aus der Schmelze verpressbare Polyamidform-massen aus Polypyrrolidon |
| US3094511A (en) * | 1958-11-17 | 1963-06-18 | Du Pont | Wholly aromatic polyamides |
| US3133138A (en) * | 1958-12-19 | 1964-05-12 | Du Pont | Stretching and heat crystallization of poly(meta-phenylene isophthalamide) fibers |
| US3197443A (en) * | 1960-07-13 | 1965-07-27 | Du Pont | Thermally stable polyamides from symmetrically substituted aromatic diamines |
| US3079219A (en) * | 1960-12-06 | 1963-02-26 | Du Pont | Process for wet spinning aromatic polyamides |
| NL126686C (enrdf_load_stackoverflow) * | 1961-01-02 | |||
| NL122899C (enrdf_load_stackoverflow) * | 1961-11-24 | |||
| US3274151A (en) * | 1962-11-21 | 1966-09-20 | Schweizerische Viscose | Polyamides containing a combination of (1) a phenol, (2) a phosphorus acid salt or ester, (3) a manganese salt, and (4) a dicarboxylic acid as stabilizers |
| US3322728A (en) * | 1963-06-17 | 1967-05-30 | Du Pont | Sulfonyl aromatic polyamides |
| US3349062A (en) * | 1966-07-21 | 1967-10-24 | Du Pont | Halogenated aromatic polyamides |
| US4568736A (en) * | 1984-09-17 | 1986-02-04 | The Standard Oil Company | Preparation of polyamide from omega-aminonitrile with oxygen containing phosphorus catalyst |
| FR2700768B1 (fr) * | 1993-01-25 | 1995-02-24 | Rhone Poulenc Chimie | Procédé de préparation d'un monoamide alpha-amino omega-ester et procédé de fabrication d'un polyamide. |
| FR3008984B1 (fr) * | 2013-07-24 | 2017-04-28 | Rhodia Operations | Articles obtenus a partir d'une composition polymerique, procede de preparation et utilisations |
-
1935
- 1935-05-09 GB GB13666/35A patent/GB461237A/en not_active Expired
- 1935-05-18 DE DEP71282D patent/DE749747C/de not_active Expired
- 1935-05-24 FR FR790521D patent/FR790521A/fr not_active Expired
-
1936
- 1936-07-24 FR FR47615D patent/FR47615E/fr not_active Expired
- 1936-07-28 BE BE416730D patent/BE416730A/xx unknown
- 1936-07-30 GB GB21149/36A patent/GB474999A/en not_active Expired
-
1937
- 1937-05-20 GB GB14039/37A patent/GB495790A/en not_active Expired
- 1937-06-01 FR FR48571D patent/FR48571E/fr not_active Expired
- 1937-06-02 BE BE421889D patent/BE421889A/xx unknown
- 1937-08-25 FR FR48742D patent/FR48742E/fr not_active Expired
- 1937-08-25 DE DEP75794A patent/DE740348C/de not_active Expired
- 1937-08-30 GB GB23661/37A patent/GB501527A/en not_active Expired
-
1938
- 1938-09-29 NL NL52489D patent/NL52489C/xx active
-
1939
- 1939-09-25 FR FR50942D patent/FR50942E/fr not_active Expired
- 1939-09-27 DE DEP79822D patent/DE745029C/de not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1040785B (de) * | 1953-06-04 | 1958-10-09 | California Research Corp | Verfahren zur Herstellung von Polyamiden |
| DE1024234B (de) * | 1953-09-29 | 1958-02-13 | California Research Corp | Verfahren zur Herstellung von linearen Polyamiden aus Diaminen und aliphatischen Dicarbonsaeuren |
| DE1211390B (de) * | 1957-08-28 | 1966-02-24 | Perfogit Societa Per Azioni | Verfahren zur Polykondensation von aus Diaminen und Dicarbonsaeuren gebildeten Salzen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR50942E (fr) | 1941-05-10 |
| DE740348C (de) | 1943-10-19 |
| FR48742E (fr) | 1938-06-21 |
| FR47615E (fr) | 1937-06-15 |
| BE416730A (enrdf_load_stackoverflow) | 1936-08-31 |
| DE745029C (de) | 1944-02-23 |
| FR48571E (fr) | 1938-04-05 |
| GB495790A (en) | 1938-11-21 |
| FR790521A (fr) | 1935-11-22 |
| GB474999A (en) | 1937-11-11 |
| NL52489C (enrdf_load_stackoverflow) | 1941-12-15 |
| GB501527A (en) | 1939-02-28 |
| GB461237A (en) | 1937-02-09 |
| BE421889A (enrdf_load_stackoverflow) | 1937-07-31 |
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