DE2229056A1 - Polyamidharze und verfahren zu deren herstellung - Google Patents
Polyamidharze und verfahren zu deren herstellungInfo
- Publication number
- DE2229056A1 DE2229056A1 DE2229056A DE2229056A DE2229056A1 DE 2229056 A1 DE2229056 A1 DE 2229056A1 DE 2229056 A DE2229056 A DE 2229056A DE 2229056 A DE2229056 A DE 2229056A DE 2229056 A1 DE2229056 A1 DE 2229056A1
- Authority
- DE
- Germany
- Prior art keywords
- equivalents
- acid
- fatty acid
- carbon atoms
- piperazine
- 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 26
- 229920006122 polyamide resin Polymers 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 91
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 82
- 239000002253 acid Substances 0.000 claims description 54
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 50
- 239000000194 fatty acid Substances 0.000 claims description 50
- 229930195729 fatty acid Natural products 0.000 claims description 50
- 150000004665 fatty acids Chemical class 0.000 claims description 50
- 235000011037 adipic acid Nutrition 0.000 claims description 46
- 239000001361 adipic acid Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 26
- 229920002554 vinyl polymer Polymers 0.000 claims description 26
- 239000000539 dimer Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 piperazine compound Chemical class 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 14
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 12
- 239000011342 resin composition Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004984 aromatic diamines Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000004831 Hot glue Substances 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005304 joining Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000011347 resin Substances 0.000 description 56
- 229920005989 resin Polymers 0.000 description 56
- 229960000250 adipic acid Drugs 0.000 description 41
- 230000000704 physical effect Effects 0.000 description 15
- 239000004952 Polyamide Substances 0.000 description 13
- 229920002647 polyamide Polymers 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 11
- 239000012943 hotmelt Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000004135 Bone phosphate Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000004885 piperazines Chemical class 0.000 description 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-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
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 2
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- KTRJPKYFFZFQJB-UHFFFAOYSA-N 2-[4-(3-piperidin-4-ylpropyl)piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1CCCC1CCNCC1 KTRJPKYFFZFQJB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 description 1
- ZILQRIKYRNQQDE-UHFFFAOYSA-N 4-(2-piperidin-4-ylethyl)piperidine Chemical compound C1CNCCC1CCC1CCNCC1 ZILQRIKYRNQQDE-UHFFFAOYSA-N 0.000 description 1
- OXEZLYIDQPBCBB-UHFFFAOYSA-N 4-(3-piperidin-4-ylpropyl)piperidine Chemical compound C1CNCCC1CCCC1CCNCC1 OXEZLYIDQPBCBB-UHFFFAOYSA-N 0.000 description 1
- YGIWTLULBLUFRJ-UHFFFAOYSA-N 4-(4-piperidin-4-ylbutyl)piperidine Chemical compound C1CNCCC1CCCCC1CCNCC1 YGIWTLULBLUFRJ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood 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
- C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty 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)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15309771A | 1971-06-14 | 1971-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2229056A1 true DE2229056A1 (de) | 1973-01-11 |
Family
ID=22545760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2229056A Pending DE2229056A1 (de) | 1971-06-14 | 1972-06-14 | Polyamidharze und verfahren zu deren herstellung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3738950A (enExample) |
| JP (1) | JPS5525219B1 (enExample) |
| AU (1) | AU460457B2 (enExample) |
| BE (1) | BE784877A (enExample) |
| CA (1) | CA973995A (enExample) |
| DE (1) | DE2229056A1 (enExample) |
| FR (1) | FR2141878B1 (enExample) |
| GB (1) | GB1400611A (enExample) |
| IT (1) | IT956544B (enExample) |
| NL (1) | NL7208144A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0182957A1 (en) * | 1984-11-29 | 1986-06-04 | Union Camp Corporation | Polyamides |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082708A (en) * | 1976-09-20 | 1978-04-04 | H. B. Fuller Company | Adhesive systems comprising a bisamino piperazine-containing polyamide |
| US4282346A (en) * | 1979-02-02 | 1981-08-04 | Emery Industries, Inc. | Preparation of copolyamide from dicarboxylic acid mixture, piperazine and polyoxyalkylene diamine |
| US4229567A (en) * | 1979-02-02 | 1980-10-21 | Emery Industries, Inc. | Copolyamide resins from piperazine and polyoxyalkylene diamine having improved creep resistance |
| JPS57111488A (en) * | 1980-12-29 | 1982-07-10 | Mitsubishi Marorii Yakin Kogyo Kk | Timer device |
| JPS59679A (ja) * | 1982-06-28 | 1984-01-05 | Nakagawa Denka Sangyo Kk | タイマ |
| IT1180214B (it) | 1984-08-02 | 1987-09-23 | Chem Plast Spa | Promotori d'adesione per plastisols in grado di mantenere stabile il colore dei plastisols all'effetto del trattamento termico d'applicazione |
| US4652327A (en) * | 1985-03-22 | 1987-03-24 | Union Camp Corporation | Bonding poly(vinylidene chloride) |
| DE3531941A1 (de) * | 1985-09-07 | 1987-03-12 | Henkel Kgaa | Polyamidharze |
| US4780146A (en) * | 1986-07-30 | 1988-10-25 | Owens-Corning Fiberglas Corporation | Modified asphalt |
| US5296557A (en) * | 1992-07-02 | 1994-03-22 | Union Camp Corporation | Two-component curable hot melt compositions |
| FR3023294B1 (fr) | 2014-07-01 | 2018-07-13 | Arkema France | Polyamides a base d'aminoalkyl- ou aminoaryl- piperazine pour adhesifs thermofusibles |
| US11781015B2 (en) * | 2017-09-20 | 2023-10-10 | Basf Se | Heat resistant polyamide composition |
-
1971
- 1971-06-14 US US00153097A patent/US3738950A/en not_active Expired - Lifetime
-
1972
- 1972-04-25 JP JP4098972A patent/JPS5525219B1/ja active Pending
- 1972-05-26 CA CA143,154A patent/CA973995A/en not_active Expired
- 1972-06-13 GB GB2747872A patent/GB1400611A/en not_active Expired
- 1972-06-13 FR FR7221260A patent/FR2141878B1/fr not_active Expired
- 1972-06-14 AU AU43411/72A patent/AU460457B2/en not_active Expired
- 1972-06-14 DE DE2229056A patent/DE2229056A1/de active Pending
- 1972-06-14 NL NL7208144A patent/NL7208144A/xx unknown
- 1972-06-14 IT IT25644/72A patent/IT956544B/it active
- 1972-06-14 BE BE784877A patent/BE784877A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0182957A1 (en) * | 1984-11-29 | 1986-06-04 | Union Camp Corporation | Polyamides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7208144A (enExample) | 1972-12-18 |
| IT956544B (it) | 1973-10-10 |
| BE784877A (fr) | 1972-12-14 |
| GB1400611A (en) | 1975-07-09 |
| FR2141878B1 (enExample) | 1977-12-23 |
| AU4341172A (en) | 1973-12-20 |
| AU460457B2 (en) | 1975-04-02 |
| CA973995A (en) | 1975-09-02 |
| US3738950A (en) | 1973-06-12 |
| FR2141878A1 (enExample) | 1973-01-26 |
| JPS5525219B1 (enExample) | 1980-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |