CA1120192A - Polyamides aliphatiques - Google Patents

Polyamides aliphatiques

Info

Publication number: CA1120192A
Authority: CA; Canada
Prior art keywords: formula; atoms; polyamide according; polyamides; recurring structural
Prior art date: 1978-11-03
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

CA000315811A

Other languages

English (en)

Inventor

Josef Pfeifer

Heinz Peter

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1978-11-03

Filing date

1978-11-03

Publication date

1982-03-16

1978-11-03 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1978-11-03 Priority to CA000315811A priority Critical patent/CA1120192A/fr

1982-03-16 Application granted granted Critical

1982-03-16 Publication of CA1120192A publication Critical patent/CA1120192A/fr

Status Expired legal-status Critical Current

Links

239000004953 Aliphatic polyamide Substances 0.000 title claims abstract description 8
229920003231 aliphatic polyamide Polymers 0.000 title claims abstract description 7
239000004952 Polyamide Substances 0.000 claims abstract description 40
229920002647 polyamide Polymers 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 23
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims abstract description 16
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 20
-1 3-heptyl Chemical group 0.000 claims description 16
150000004985 diamines Chemical class 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229940013361 cresol Drugs 0.000 claims 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
238000010521 absorption reaction Methods 0.000 abstract description 4
239000001361 adipic acid Substances 0.000 abstract description 4
230000009477 glass transition Effects 0.000 abstract description 4
235000011037 adipic acid Nutrition 0.000 abstract description 3
238000001125 extrusion Methods 0.000 abstract description 2
230000007062 hydrolysis Effects 0.000 abstract description 2
238000006460 hydrolysis reaction Methods 0.000 abstract description 2
238000001746 injection moulding Methods 0.000 abstract description 2
125000001931 aliphatic group Chemical group 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000003054 catalyst Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 14
239000007788 liquid Substances 0.000 description 12
FLGIBBNBFWNAJN-UHFFFAOYSA-N 3,12-dipropyl-1,2-diazacyclododeca-1,5,9-triene Chemical compound CCCC1CC=CCCC=CCC(CCC)N=N1 FLGIBBNBFWNAJN-UHFFFAOYSA-N 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
150000001991 dicarboxylic acids Chemical class 0.000 description 6
238000011097 chromatography purification Methods 0.000 description 5
238000006068 polycondensation reaction Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
KVHGRNNYXUQOHE-UHFFFAOYSA-N octadecane-5,14-diamine Chemical compound CCCCC(N)CCCCCCCCC(N)CCCC KVHGRNNYXUQOHE-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
AZCPJRSLLFDOJD-UHFFFAOYSA-N 1,2-diazacyclododecane Chemical class C1CCCCCNNCCCC1 AZCPJRSLLFDOJD-UHFFFAOYSA-N 0.000 description 2
FZUWIRGHKCUMTH-UHFFFAOYSA-N 2,13-dimethyltetradecane-3,12-diamine Chemical compound CC(C)C(N)CCCCCCCCC(N)C(C)C FZUWIRGHKCUMTH-UHFFFAOYSA-N 0.000 description 2
MZNQLXRKWSZAJE-UHFFFAOYSA-N 3,14-diethylhexadecane-4,13-diamine Chemical compound CCC(CC)C(N)CCCCCCCCC(N)C(CC)CC MZNQLXRKWSZAJE-UHFFFAOYSA-N 0.000 description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
BDIFKMOUQSYRRD-UHFFFAOYSA-N diphenyl hexanedioate Chemical compound C=1C=CC=CC=1OC(=O)CCCCC(=O)OC1=CC=CC=C1 BDIFKMOUQSYRRD-UHFFFAOYSA-N 0.000 description 2
UXWHXEQADOLPLB-UHFFFAOYSA-N docosane-7,16-diamine Chemical compound CCCCCCC(N)CCCCCCCCC(N)CCCCCC UXWHXEQADOLPLB-UHFFFAOYSA-N 0.000 description 2
MIHXSBPXSQUTAE-UHFFFAOYSA-N hexadecane-4,13-diamine Chemical compound CCCC(N)CCCCCCCCC(N)CCC MIHXSBPXSQUTAE-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 description 1
JWAGOKOJCIHYQM-UHFFFAOYSA-N 1,2-diazacyclododeca-1,5,9-triene Chemical class C1CC=CCCN=NCCC=C1 JWAGOKOJCIHYQM-UHFFFAOYSA-N 0.000 description 1
IYXWYOHBKDNWPK-UHFFFAOYSA-N 1,4-di(pentan-3-yl)-1,3-diazacyclododecane Chemical compound CCC(CC)C1CCCCCCCCN(C(CC)CC)CN1 IYXWYOHBKDNWPK-UHFFFAOYSA-N 0.000 description 1
DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
YJQFWWYXQJWYGY-UHFFFAOYSA-N 3,12-bis(2-methylpropyl)-1,2-diazacyclododeca-1,5,9-triene Chemical compound CC(C)CC1CC=CCCC=CCC(CC(C)C)N=N1 YJQFWWYXQJWYGY-UHFFFAOYSA-N 0.000 description 1
AGOLXLZVBFCWDU-UHFFFAOYSA-N 3,12-di(cycloheptyl)-1,2-diazacyclododeca-1,5,9-triene Chemical compound C1CCCCCC1C1N=NC(C2CCCCCC2)CC=CCCC=CC1 AGOLXLZVBFCWDU-UHFFFAOYSA-N 0.000 description 1
UHANCPQXXFFQPI-UHFFFAOYSA-N 3,12-di(cyclooctyl)-1,2-diazacyclododecane Chemical compound C1CCCCCCC1C1NNC(C2CCCCCCC2)CCCCCCCC1 UHANCPQXXFFQPI-UHFFFAOYSA-N 0.000 description 1
QDBHQLRQUFTSGH-UHFFFAOYSA-N 3,12-di(heptan-3-yl)-1,2-diazacyclododecane Chemical compound CCCCC(CC)C1CCCCCCCCC(C(CC)CCCC)NN1 QDBHQLRQUFTSGH-UHFFFAOYSA-N 0.000 description 1
BBTRCYYUMSSYHU-UHFFFAOYSA-N 3,12-di(nonyl)-1,2-diazacyclododeca-1,5,9-triene Chemical compound CCCCCCCCCC1CC=CCCC=CCC(CCCCCCCCC)N=N1 BBTRCYYUMSSYHU-UHFFFAOYSA-N 0.000 description 1
DCJGSRDEMTWORD-UHFFFAOYSA-N 3,12-di(propan-2-yl)-1,2-diazacyclododeca-1,5,9-triene Chemical compound CC(C)C1CC=CCCC=CCC(C(C)C)N=N1 DCJGSRDEMTWORD-UHFFFAOYSA-N 0.000 description 1
ZCBKEPFTNJHENF-UHFFFAOYSA-N 3,12-di(undecyl)-1,2-diazacyclododeca-1,5,9-triene Chemical compound CCCCCCCCCCCC1CC=CCCC=CCC(CCCCCCCCCCC)N=N1 ZCBKEPFTNJHENF-UHFFFAOYSA-N 0.000 description 1
UGFCHBBTJUBHNJ-UHFFFAOYSA-N 3,12-dibutyl-1,2-diazacyclododeca-1,5,9-triene Chemical compound CCCCC1CC=CCCC=CCC(CCCC)N=N1 UGFCHBBTJUBHNJ-UHFFFAOYSA-N 0.000 description 1
XXXHNPGDACULKH-UHFFFAOYSA-N 3,12-dicyclohexyl-1,2-diazacyclododeca-1,5,9-triene Chemical compound C1CCCCC1C1N=NC(C2CCCCC2)CC=CCCC=CC1 XXXHNPGDACULKH-UHFFFAOYSA-N 0.000 description 1
DCKRBYKJPRUSCG-UHFFFAOYSA-N 3,12-dicyclopentyl-1,2-diazacyclododeca-1,5,9-triene Chemical compound C1CCCC1C1N=NC(C2CCCC2)CC=CCCC=CC1 DCKRBYKJPRUSCG-UHFFFAOYSA-N 0.000 description 1
IESIKJRMPLJOEN-UHFFFAOYSA-N 3,12-dihexyl-1,2-diazacyclododecane Chemical compound CCCCCCC1CCCCCCCCC(CCCCCC)NN1 IESIKJRMPLJOEN-UHFFFAOYSA-N 0.000 description 1
WFOLTJIMYJZVGJ-UHFFFAOYSA-N 3,12-dipentyl-1,2-diazacyclododecane Chemical compound CCCCCC1CCCCCCCCC(CCCCC)NN1 WFOLTJIMYJZVGJ-UHFFFAOYSA-N 0.000 description 1
HNFIPQMTDQIVIN-UHFFFAOYSA-N 5,16-diethylicosane Chemical compound C(C)C(CCCC)CCCCCCCCCCC(CCCC)CC HNFIPQMTDQIVIN-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000007707 calorimetry Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
WHGYJUPJEFDRHW-UHFFFAOYSA-N dotriacontane-12,21-diamine Chemical compound CCCCCCCCCCCC(N)CCCCCCCCC(N)CCCCCCCCCCC WHGYJUPJEFDRHW-UHFFFAOYSA-N 0.000 description 1
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical group CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000010985 leather Substances 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
MMCQGZHYFCKPJP-UHFFFAOYSA-N octacosane-10,19-diamine Chemical compound CCCCCCCCCC(N)CCCCCCCCC(N)CCCCCCCCC MMCQGZHYFCKPJP-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004753 textile Substances 0.000 description 1

Landscapes

Polyamides (AREA)

CA000315811A 1978-11-03 1978-11-03 Polyamides aliphatiques Expired CA1120192A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000315811A CA1120192A (fr)	1978-11-03	1978-11-03	Polyamides aliphatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000315811A CA1120192A (fr)	1978-11-03	1978-11-03	Polyamides aliphatiques

Publications (1)

Publication Number	Publication Date
CA1120192A true CA1120192A (fr)	1982-03-16

Family

ID=4112885

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000315811A Expired CA1120192A (fr)	1978-11-03	1978-11-03	Polyamides aliphatiques

Country Status (1)

Country	Link
CA (1)	CA1120192A (fr)

1978
- 1978-11-03 CA CA000315811A patent/CA1120192A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-16	MKEX	Expiry

Publication	Publication Date	Title
KR100580411B1 (ko)	2006-05-16	모노메틸아디페이트 및 헥사메틸렌디아민으로부터폴리(헥사메틸렌 아디프아미드)의 제조 방법
US4195165A (en)	1980-03-25	Aliphatic polyamide from disubstituted decane diamine
CA1186845A (fr)	1985-05-07	Polyamides transparents, leur production et leur emploi en fabrication d'articles faconnes
CA1120192A (fr)	1982-03-16	Polyamides aliphatiques
US4210742A (en)	1980-07-01	Transparent polyamides from branched chain diamine
US4210743A (en)	1980-07-01	Transparent polyamides from branched chain diamines
CA1120190A (fr)	1982-03-16	Polyamides cristallins
US4377683A (en)	1983-03-22	Transparent copolyamide from isophorone diamine and substituted undecane diamine
US3396151A (en)	1968-08-06	Polyamides from methylene dibenzoic acid characterized by relatively high softening and melting points
JPS6139975B2 (fr)	1986-09-06
US2917490A (en)	1959-12-15	Polyamides from norcamphaneaminocarboxylic acids
US4258176A (en)	1981-03-24	Transparent copolyamide from 1,10-disubstituted C11 diamine
US2836579A (en)	1958-05-27	Polycarbonamide from hexamethylene diamine and 2, 2-bis-(carboxyphenyl) propane
US5686556A (en)	1997-11-11	Process for the preparation of an α-amino ω-ester monoamide and process for the manufacture of a polyamide
US4429110A (en)	1984-01-31	Transparent polyamide from branched chain arylalkyl diamine
US4024185A (en)	1977-05-17	Cycloaliphatic unsymmetrical diamines
US4297480A (en)	1981-10-27	Transparent polyamide from branched chain C11 diamine
US4258177A (en)	1981-03-24	Transparent copolyamide from 1,10-disubstituted C10 diamine
US2894025A (en)	1959-07-07	Gamma-(3-aminocyclohexyl)butyric acid and esters
US4255559A (en)	1981-03-10	Transparent copolyamide from 1,10-disubstituted-1,10 diamine
US4202961A (en)	1980-05-13	Transparent polyamide from aromatic dicarboxylic acid and disubstituted decane diamine
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US4187371A (en)	1980-02-05	Formation of terephthalamide polymer of 5-methyl-1,9-nonanediamine
CA1120191A (fr)	1982-03-16	Polyamides transparents
US4025493A (en)	1977-05-24	Polyamides and polyesters from phenyl-substituted alkane dioic acids