CA1248687A - Process for preparing pulverulent coating means based on polyamides with at least 10 aliphatically bound carbon atoms per carbonamide group - Google Patents
Process for preparing pulverulent coating means based on polyamides with at least 10 aliphatically bound carbon atoms per carbonamide groupInfo
- Publication number
- CA1248687A CA1248687A CA000504769A CA504769A CA1248687A CA 1248687 A CA1248687 A CA 1248687A CA 000504769 A CA000504769 A CA 000504769A CA 504769 A CA504769 A CA 504769A CA 1248687 A CA1248687 A CA 1248687A
- Authority
- CA
- Canada
- Prior art keywords
- solution
- temperature
- polyamide
- ethanol
- precipitation
- 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 abstract description 47
- 229920002647 polyamide Polymers 0.000 title claims abstract description 44
- 125000005521 carbonamide group Chemical group 0.000 title claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 238000000576 coating method Methods 0.000 title abstract description 18
- 239000011248 coating agent Substances 0.000 title abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 63
- 238000001556 precipitation Methods 0.000 claims abstract description 46
- 239000000243 solution Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000000843 powder Substances 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 19
- 235000019441 ethanol Nutrition 0.000 claims description 25
- 229960004756 ethanol Drugs 0.000 claims description 24
- 239000002245 particle Substances 0.000 claims description 17
- 150000003951 lactams Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000004781 supercooling Methods 0.000 claims description 4
- 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 claims description 3
- 229930003836 cresol Natural products 0.000 claims description 3
- 239000007888 film coating Substances 0.000 claims description 3
- 238000009501 film coating Methods 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000004821 distillation Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- 238000009826 distribution Methods 0.000 description 7
- 238000000227 grinding Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000009503 electrostatic coating Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000001376 precipitating effect Effects 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
- 238000005245 sintering Methods 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HASUJDLTAYUWCO-UHFFFAOYSA-N 2-aminoundecanoic acid Chemical compound CCCCCCCCCC(N)C(O)=O HASUJDLTAYUWCO-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960005419 nitrogen Drugs 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 229910052950 sphalerite Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- 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
- C08G69/46—Post-polymerisation treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyamides (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853510691 DE3510691A1 (de) | 1985-03-23 | 1985-03-23 | Verfahren zur herstellung von pulverfoermigen beschichtungsmitteln auf der basis von polyamiden mit mindestens 10 aliphatisch gebundenen kohlenstoffatomen pro carbonamidgruppe |
| DEP3510691.3 | 1985-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1248687A true CA1248687A (en) | 1989-01-10 |
Family
ID=6266209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000504769A Expired CA1248687A (en) | 1985-03-23 | 1986-03-21 | Process for preparing pulverulent coating means based on polyamides with at least 10 aliphatically bound carbon atoms per carbonamide group |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4687838A (enExample) |
| EP (1) | EP0202389B1 (enExample) |
| JP (1) | JPS61221273A (enExample) |
| AT (1) | ATE57950T1 (enExample) |
| AU (1) | AU568449B2 (enExample) |
| CA (1) | CA1248687A (enExample) |
| DE (2) | DE3510691A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5091508A (en) * | 1989-12-20 | 1992-02-25 | Khanna Yash P | Process for improving the properties of polymers |
| DE10233344A1 (de) * | 2002-07-23 | 2004-02-12 | Degussa Ag | Polyamid-Wirbelsinterpulver für das Dünnschichtwirbelsintern |
| DE10311437A1 (de) * | 2003-03-15 | 2004-09-23 | Degussa Ag | Laser-Sinter-Pulver mit PMMI, PMMA und/oder PMMI-PMMA-Copolymeren, Verfahren zu dessen Herstellung und Formkörper, hergestellt aus diesem Laser-Sinterpulver |
| US8232261B2 (en) | 2003-07-18 | 2012-07-31 | Bayer Cropscience Lp | Method of minimizing herbicidal injury |
| FR2905700B1 (fr) * | 2006-09-08 | 2008-11-14 | Arkema France | Poudre autoadherente haute performance sans promoteur d'adhesion a base de polyamide |
| JP2008303304A (ja) * | 2007-06-07 | 2008-12-18 | Metal Color:Kk | 結晶性ポリアミド微粒子の製造方法 |
| US9468891B2 (en) * | 2011-03-23 | 2016-10-18 | M. Technique Co., Ltd. | Method for producing microparticles |
| DE102011078719A1 (de) | 2011-07-06 | 2013-01-10 | Evonik Degussa Gmbh | Pulver enthaltend mit Polymer beschichtete Partikel |
| DE102011078720A1 (de) | 2011-07-06 | 2013-01-10 | Evonik Degussa Gmbh | Pulver enthaltend mit Polymer beschichtete Kernpartikel enthaltend Metalle, Metalloxide, Metall- oder Halbmetallnitride |
| DE102011078722A1 (de) | 2011-07-06 | 2013-01-10 | Evonik Degussa Gmbh | Pulver enthaltend mit Polymer beschichtete anorganische Partikel |
| DE102011078721A1 (de) | 2011-07-06 | 2013-01-10 | Evonik Degussa Gmbh | Pulver enthaltend mit Polymer beschichtete polymere Kernpartikel |
| EP4245506A1 (de) | 2022-03-15 | 2023-09-20 | Evonik Operations GmbH | Pulver zur verarbeitung in einem schichtweisen verfahren mit lasern im sichtbaren und nahinfrarotbereich |
| DE202022000644U1 (de) | 2022-03-15 | 2022-04-21 | Evonik Operations Gmbh | Pulver zur Verarbeitung in einem schichtweisen Verfahren mit Lasern im sichtbaren und Nahinfrarotbereich |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143025A (en) * | 1975-10-09 | 1979-03-06 | Chemische Werke Huls Ag | Method for producing polylaurolactam powder compositions for the coating of metals at high temperatures |
| DE2906647C2 (de) * | 1979-02-21 | 1980-12-11 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von pulver· förmigen Beschichtungsmittel!! auf der Basis von Polyamiden mit mindestens 10 aliphatisch gebundenen Kohlenstoffatomen pro Carbonamidgruppe |
| DE3510690A1 (de) * | 1985-03-23 | 1986-09-25 | Hüls AG, 4370 Marl | Verfahren zur herstellung von nachkondensierbaren, hochmolekularen beschichtungsmitteln auf der basis von polyamiden nach dem faellungsverfahren |
| DE3510689A1 (de) * | 1985-03-23 | 1986-09-25 | Hüls AG, 4370 Marl | Verfahren zur herstellung von pulverfoermigen beschichtungsmitteln praktisch einheitlicher korngroessen auf der basis von polyamiden mit mindestens 10 aliphatisch gebundenen kohlenstoffatomen pro carbonamidgruppe |
| DE3510688A1 (de) * | 1985-03-23 | 1986-09-25 | Hüls AG, 4370 Marl | Beschichtungspulver fuer das schmelzueberzugsverfahren auf der basis von polyamiden und haftverbessernden zusaetzen |
-
1985
- 1985-03-23 DE DE19853510691 patent/DE3510691A1/de not_active Withdrawn
-
1986
- 1986-01-23 AT AT86100872T patent/ATE57950T1/de not_active IP Right Cessation
- 1986-01-23 EP EP86100872A patent/EP0202389B1/de not_active Expired - Lifetime
- 1986-01-23 DE DE8686100872T patent/DE3675256D1/de not_active Expired - Lifetime
- 1986-03-18 US US06/840,819 patent/US4687838A/en not_active Expired - Lifetime
- 1986-03-21 CA CA000504769A patent/CA1248687A/en not_active Expired
- 1986-03-21 AU AU54999/86A patent/AU568449B2/en not_active Ceased
- 1986-03-24 JP JP61064294A patent/JPS61221273A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61221273A (ja) | 1986-10-01 |
| US4687838A (en) | 1987-08-18 |
| EP0202389B1 (de) | 1990-10-31 |
| EP0202389A2 (de) | 1986-11-26 |
| DE3675256D1 (de) | 1990-12-06 |
| AU568449B2 (en) | 1987-12-24 |
| ATE57950T1 (de) | 1990-11-15 |
| AU5499986A (en) | 1986-09-25 |
| JPH027984B2 (enExample) | 1990-02-21 |
| DE3510691A1 (de) | 1986-09-25 |
| EP0202389A3 (en) | 1987-11-19 |
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| CA1248687A (en) | Process for preparing pulverulent coating means based on polyamides with at least 10 aliphatically bound carbon atoms per carbonamide group | |
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| JPS60197734A (ja) | ポリアミド樹脂微粒子の製造方法 | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |