RU2066331C1 - Способ повышения молекулярного веса полиамида - Google Patents
Способ повышения молекулярного веса полиамида Download PDFInfo
- Publication number
- RU2066331C1 RU2066331C1 SU894895302A SU4895302A RU2066331C1 RU 2066331 C1 RU2066331 C1 RU 2066331C1 SU 894895302 A SU894895302 A SU 894895302A SU 4895302 A SU4895302 A SU 4895302A RU 2066331 C1 RU2066331 C1 RU 2066331C1
- Authority
- RU
- Russia
- Prior art keywords
- acid
- polyamide
- methoxyphenylphosphonic
- polyamides
- molecular weight
- Prior art date
Links
- 239000004952 Polyamide Substances 0.000 title claims abstract description 34
- 229920002647 polyamide Polymers 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- HAIZAZONHOVLEK-UHFFFAOYSA-N (4-nitrophenyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC=C([N+]([O-])=O)C=C1 HAIZAZONHOVLEK-UHFFFAOYSA-N 0.000 claims abstract description 5
- QDBZWLAQPHAUGV-UHFFFAOYSA-N (2-methoxyphenyl)phosphonic acid Chemical compound COC1=CC=CC=C1P(O)(O)=O QDBZWLAQPHAUGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- YXTSJMYYIRPSDF-UHFFFAOYSA-N (2-methylphenyl)phosphonic acid Chemical compound CC1=CC=CC=C1P(O)(O)=O YXTSJMYYIRPSDF-UHFFFAOYSA-N 0.000 claims abstract description 4
- HCGRZKQJKAPKMJ-UHFFFAOYSA-N (2-phenylmethoxyphenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1OCC1=CC=CC=C1 HCGRZKQJKAPKMJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- VWEAZVFNLFJJSV-UHFFFAOYSA-N (4-methoxyphenyl)phosphinic acid Chemical compound COC1=CC=C(P(O)=O)C=C1 VWEAZVFNLFJJSV-UHFFFAOYSA-N 0.000 claims abstract description 4
- WGQNMORNKLCTTO-UHFFFAOYSA-N 1-diaminophosphoryl-4-methoxybenzene Chemical compound COC1=CC=C(P(N)(N)=O)C=C1 WGQNMORNKLCTTO-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZIRFSYZTOKLLIT-UHFFFAOYSA-N COc1ccc(c(OC)c1)P(O)=O Chemical compound COc1ccc(c(OC)c1)P(O)=O ZIRFSYZTOKLLIT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- BFKIIIIRGBJFCB-UHFFFAOYSA-N (2,6-dimethylphenyl)phosphonic acid Chemical compound CC1=CC=CC(C)=C1P(O)(O)=O BFKIIIIRGBJFCB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 229920002302 Nylon 6,6 Polymers 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- GJTJNLGUQDZCOA-UHFFFAOYSA-N (2,5-dimethylphenyl)phosphonic acid Chemical compound CC1=CC=C(C)C(P(O)(O)=O)=C1 GJTJNLGUQDZCOA-UHFFFAOYSA-N 0.000 abstract description 4
- RLECYDDAXLQZBO-UHFFFAOYSA-N (2,4-dimethoxyphenyl)phosphonic acid Chemical compound COC1=CC=C(P(O)(O)=O)C(OC)=C1 RLECYDDAXLQZBO-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 description 10
- 239000004677 Nylon Substances 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 6
- -1 alkylaryl radical Chemical class 0.000 description 4
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FFVGUXNXIMSWPI-UHFFFAOYSA-N CC1=CC=C(C)C(P(O)=O)=C1 Chemical compound CC1=CC=C(C)C(P(O)=O)=C1 FFVGUXNXIMSWPI-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material 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
- C08G69/04—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
- C08G69/18—Anionic polymerisation
- C08G69/20—Anionic polymerisation characterised by the catalysts used
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/262,936 US4966949A (en) | 1988-10-20 | 1988-10-20 | Process for increasing the molecular weight of a polyamide with p containing catalyst |
| US262936 | 1988-10-20 | ||
| PCT/US1989/003464 WO1990004614A1 (en) | 1988-10-20 | 1989-08-17 | Process for increasing the molecular weight of a polyamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2066331C1 true RU2066331C1 (ru) | 1996-09-10 |
Family
ID=22999705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU894895302A RU2066331C1 (ru) | 1988-10-20 | 1989-08-17 | Способ повышения молекулярного веса полиамида |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4966949A (enExample) |
| EP (1) | EP0439470B1 (enExample) |
| JP (1) | JP2888573B2 (enExample) |
| AR (1) | AR243912A1 (enExample) |
| CA (1) | CA2001090A1 (enExample) |
| DE (1) | DE68919228T2 (enExample) |
| IN (1) | IN171375B (enExample) |
| LV (1) | LV10469B (enExample) |
| RU (1) | RU2066331C1 (enExample) |
| TR (1) | TR24062A (enExample) |
| WO (1) | WO1990004614A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116919A (en) * | 1990-12-05 | 1992-05-26 | E. I. Du Pont De Nemours And Company | Process for increasing the relative viscosity of polyamides with reduced thermal degradation |
| US5142000A (en) * | 1991-08-28 | 1992-08-25 | E. I. Du Pont De Nemours And Company | Process for increasing polyamide molecular weight with organophosphonic acid or ester catalysts in the presence of alumina-containing titanium dioxide |
| US5543495A (en) * | 1994-03-08 | 1996-08-06 | E. I. Du Pont De Nemours And Company | Process for increasing the molecular weight of polyamides and other condensation polymers |
| US5698658A (en) * | 1996-05-31 | 1997-12-16 | E. I. Du Pont De Nemours And Company | Linear very high molecular weight polyamides and process for producing them |
| US6169162B1 (en) | 1999-05-24 | 2001-01-02 | Solutia Inc. | Continuous polyamidation process |
| DE60021211T2 (de) | 2000-01-20 | 2006-04-20 | Invista Technologies S.A.R.L., Wilmington | Polyamid kettenverlängerungs-verfahren und dadurch hergestellte funktionalisierte polyamide |
| DE60038573T2 (de) | 2000-01-20 | 2009-05-14 | Invista Technologies S.A.R.L. | Polyamid-kettenverlängerungsverfahren |
| US20190322805A1 (en) * | 2018-04-18 | 2019-10-24 | Invista North America S.A R.L. | Flame-retardant polyamide composition |
| WO2025022210A1 (en) | 2023-07-27 | 2025-01-30 | Inv Performance Materials, Llc | Polyamide yarn with improved fatigue resistance and the use thereof for the manufacture of tire cord |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3365428A (en) * | 1965-03-25 | 1968-01-23 | Celanese Corp | Polymerization of polyamide-precursor salt in the presence of a phosphinic acid |
| GB1084324A (enExample) * | 1965-06-23 | |||
| US4912175A (en) * | 1988-08-01 | 1990-03-27 | E. I. Du Pont De Nemours And Company | Process for in creasing polyamide molecular weight with P containing catalyst |
-
1988
- 1988-10-20 US US07/262,936 patent/US4966949A/en not_active Expired - Lifetime
-
1989
- 1989-08-17 JP JP1509052A patent/JP2888573B2/ja not_active Expired - Lifetime
- 1989-08-17 RU SU894895302A patent/RU2066331C1/ru active
- 1989-08-17 WO PCT/US1989/003464 patent/WO1990004614A1/en not_active Ceased
- 1989-08-17 DE DE68919228T patent/DE68919228T2/de not_active Expired - Lifetime
- 1989-08-17 EP EP89909640A patent/EP0439470B1/en not_active Expired - Lifetime
- 1989-10-18 IN IN862/CAL/89A patent/IN171375B/en unknown
- 1989-10-20 AR AR89315237A patent/AR243912A1/es active
- 1989-10-20 CA CA002001090A patent/CA2001090A1/en not_active Abandoned
- 1989-10-20 TR TR89/0808A patent/TR24062A/xx unknown
-
1993
- 1993-05-14 LV LVP-93-349A patent/LV10469B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент США N 3365428, кл. 528-336, опублик. 1970. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0439470A1 (en) | 1991-08-07 |
| DE68919228T2 (de) | 1995-03-23 |
| JPH04501126A (ja) | 1992-02-27 |
| US4966949A (en) | 1990-10-30 |
| EP0439470B1 (en) | 1994-11-02 |
| LV10469A (lv) | 1995-02-20 |
| LV10469B (en) | 1996-02-20 |
| JP2888573B2 (ja) | 1999-05-10 |
| WO1990004614A1 (en) | 1990-05-03 |
| CA2001090A1 (en) | 1990-04-20 |
| DE68919228D1 (de) | 1994-12-08 |
| IN171375B (enExample) | 1992-09-26 |
| AR243912A1 (es) | 1993-09-30 |
| TR24062A (tr) | 1991-02-22 |
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