CA1165942A - Preparation of polytetramethylene adipamide - Google Patents

Preparation of polytetramethylene adipamide

Info

Publication number: CA1165942A
Authority: CA; Canada
Prior art keywords: prepolymer; temperature; process according; water; reaction
Prior art date: 1980-03-26
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

Application number

CA000373843A

Other languages

English (en)

French (fr)

Inventor

Reinoud J. Gaymans

Edmond H.J.P. Bour

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stamicarbon BV

Original Assignee

Stamicarbon BV

Priority date (The priority date 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 date listed.)

1980-03-26

Filing date

1981-03-25

Publication date

1984-04-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19835059&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1165942(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1981-03-25 Application filed by Stamicarbon BV filed Critical Stamicarbon BV

1984-04-17 Application granted granted Critical

1984-04-17 Publication of CA1165942A publication Critical patent/CA1165942A/en

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 7
-1 polytetramethylene Polymers 0.000 title description 6
GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 title description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 35
239000004952 Polyamide Substances 0.000 claims abstract description 25
229920002647 polyamide Polymers 0.000 claims abstract description 25
229920003189 Nylon 4,6 Polymers 0.000 claims abstract description 20
230000008569 process Effects 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims description 43
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 28
239000001361 adipic acid Substances 0.000 claims description 15
235000011037 adipic acid Nutrition 0.000 claims description 15
238000010438 heat treatment Methods 0.000 claims description 15
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 9
239000005700 Putrescine Substances 0.000 claims description 7
238000006116 polymerization reaction Methods 0.000 claims description 6
DRXQIWUATHHZSU-UHFFFAOYSA-N C(CCCCC(=O)O)(=O)O.NC(C(C)N)C Chemical compound C(CCCCC(=O)O)(=O)O.NC(C(C)N)C DRXQIWUATHHZSU-UHFFFAOYSA-N 0.000 claims description 5
230000035484 reaction time Effects 0.000 claims description 5
208000036366 Sensation of pressure Diseases 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
238000006482 condensation reaction Methods 0.000 claims description 3
229920006158 high molecular weight polymer Polymers 0.000 claims description 3
SHPVGWLRFPFLNE-UHFFFAOYSA-N butane-1,4-diamine;hexanedioic acid Chemical compound NCCCCN.OC(=O)CCCCC(O)=O SHPVGWLRFPFLNE-UHFFFAOYSA-N 0.000 abstract 1
238000009833 condensation Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 14
150000004985 diamines Chemical class 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000004677 Nylon Substances 0.000 description 7
229920001778 nylon Polymers 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229920001730 Moisture cure polyurethane Polymers 0.000 description 4
230000005494 condensation Effects 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000007664 blowing Methods 0.000 description 3
238000011010 flushing procedure Methods 0.000 description 3
238000013021 overheating Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
239000002002 slurry Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000002245 particle Substances 0.000 description 2
230000003578 releasing effect Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
QFNNDGVVMCZKEY-UHFFFAOYSA-N azacyclododecan-2-one Chemical compound O=C1CCCCCCCCCCN1 QFNNDGVVMCZKEY-UHFFFAOYSA-N 0.000 description 1
MUPZPRBKMCLFOX-UHFFFAOYSA-N butane-1,1-diamine;hexanedioic acid Chemical compound CCCC(N)N.OC(=O)CCCCC(O)=O MUPZPRBKMCLFOX-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000007599 discharging Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229920006017 homo-polyamide Polymers 0.000 description 1
239000000463 material Substances 0.000 description 1
239000006224 matting agent Substances 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N n-hendecanoic acid Natural products CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
238000013022 venting Methods 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
- 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)

CA000373843A 1980-03-26 1981-03-25 Preparation of polytetramethylene adipamide Expired CA1165942A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8001763A NL8001763A (nl)	1980-03-26	1980-03-26	Bereiding van polytetramethyleenadipamide.
NL8001763		1980-03-26

Publications (1)

Publication Number	Publication Date
CA1165942A true CA1165942A (en)	1984-04-17

Family

ID=19835059

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000373843A Expired CA1165942A (en)	1980-03-26	1981-03-25	Preparation of polytetramethylene adipamide

Country Status (10)

Country	Link
US (1)	US4408036A (2)
EP (1)	EP0039524B2 (2)
JP (1)	JPS6028843B2 (2)
BR (1)	BR8101824A (2)
CA (1)	CA1165942A (2)
DE (1)	DE3164389D1 (2)
ES (1)	ES500684A0 (2)
IN (1)	IN154656B (2)
NL (1)	NL8001763A (2)
SU (1)	SU1205774A3 (2)

Families Citing this family (141)

* Cited by examiner, † Cited by third party
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DE3276758D1 (en) *	1982-11-12	1987-08-20	Stamicarbon	Use of (co)polytetramethylene-adipamide articles
JPS60220731A (ja) *	1984-04-17	1985-11-05	Unitika Ltd	ポリアミドフィルムおよびその製造方法
NL8401271A (nl) *	1984-04-19	1985-11-18	Stamicarbon	Werkwijze voor het bereiden van polytetramethyleenadipamide.
JPS61232902A (ja) *	1985-04-08	1986-10-17	Bridgestone Corp	空気入りタイヤ
US4722997A (en) *	1985-05-31	1988-02-02	Stamicarbon, B.V.	Process for the preparation of nylon 4,6
DE3667064D1 (en) *	1985-05-31	1989-12-28	Stamicarbon	Process for the preparation of nylon 4,6
DE3526931A1 (de) *	1985-07-27	1987-02-05	Bayer Ag	Verfahren zur herstellung von poly(tetramethylenadipamid)
GB8615268D0 (en) *	1986-06-23	1986-07-30	Domnick Hunter Filters Ltd	Polyamide membranes
NL8601893A (nl) *	1986-07-22	1988-02-16	Stamicarbon	Bereiding van hoog-moleculair polytetramethyleenadipamide.
NL8603138A (nl) *	1986-12-10	1988-07-01	Stamicarbon	Meerlagen polyamide vormlichaam.
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KR20110028519A (ko)	2008-06-27	2011-03-18	바스프 에스이	규조토를 갖는 열 전도성 폴리아미드
DE102008058246A1 (de)	2008-11-19	2010-05-20	Basf Se	Hochmolekulare Polyamide
EP2379644B1 (de)	2008-12-16	2018-08-22	Basf Se	Wärmealterungsbeständige polyamide
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1980
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1981
- 1981-03-25 DE DE8181200326T patent/DE3164389D1/de not_active Expired
- 1981-03-25 US US06/247,548 patent/US4408036A/en not_active Expired - Fee Related
- 1981-03-25 SU SU813372848A patent/SU1205774A3/ru active
- 1981-03-25 EP EP81200326A patent/EP0039524B2/en not_active Expired
- 1981-03-25 CA CA000373843A patent/CA1165942A/en not_active Expired
- 1981-03-25 ES ES500684A patent/ES500684A0/es active Granted
- 1981-03-26 BR BR8101824A patent/BR8101824A/pt not_active IP Right Cessation
- 1981-03-26 JP JP56044668A patent/JPS6028843B2/ja not_active Expired
- 1981-03-26 IN IN333/CAL/81A patent/IN154656B/en unknown

Also Published As

Publication number	Publication date
EP0039524A1 (en)	1981-11-11
ES8202040A1 (es)	1982-01-01
ES500684A0 (es)	1982-01-01
BR8101824A (pt)	1981-09-29
NL8001763A (nl)	1981-10-16
IN154656B (2)	1984-12-01
EP0039524B2 (en)	1989-04-26
SU1205774A3 (ru)	1986-01-15
EP0039524B1 (en)	1984-06-27
DE3164389D1 (en)	1984-08-02
US4408036A (en)	1983-10-04
JPS56149430A (en)	1981-11-19
JPS6028843B2 (ja)	1985-07-06

Legal Events

Date	Code	Title	Description
2001-04-17	MKEX	Expiry

Publication	Publication Date	Title
CA1165942A (en)	1984-04-17	Preparation of polytetramethylene adipamide
US4460762A (en)	1984-07-17	Preparation of high molecular polytetramethylene adipamide
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KR870000472B1 (ko)	1987-03-11	고분자 폴리테트라메틸렌 아디프 아미드의 제조방법
GB1590526A (en)	1981-06-03	Thermoplastic copolyamides