CA1120191A - Polyamides transparents - Google Patents

Polyamides transparents

Info

Publication number: CA1120191A
Authority: CA; Canada
Prior art keywords: formula; atoms; mixture; diamine; acid
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

CA000315764A

Other languages

English (en)

Inventor

Josef Pfeifer

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 CA000315764A priority Critical patent/CA1120191A/fr

1982-03-16 Application granted granted Critical

1982-03-16 Publication of CA1120191A publication Critical patent/CA1120191A/fr

Status Expired legal-status Critical Current

Links

239000004952 Polyamide Substances 0.000 title claims abstract description 37
229920002647 polyamide Polymers 0.000 title claims abstract description 37
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 46
239000000203 mixture Substances 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 25
150000004985 diamines Chemical class 0.000 claims abstract description 24
JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 16
238000006068 polycondensation reaction Methods 0.000 claims abstract description 14
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 10
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
235000011037 adipic acid Nutrition 0.000 claims abstract description 4
239000001361 adipic acid Substances 0.000 claims abstract description 4
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims description 12
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
150000003951 lactams Chemical class 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
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 4
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 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
TTZVHRJRFBJCRU-UHFFFAOYSA-N 1,10-dicyclohexyldecane-1,10-diamine Chemical compound C1CCCCC1C(N)CCCCCCCCC(N)C1CCCCC1 TTZVHRJRFBJCRU-UHFFFAOYSA-N 0.000 claims 3
GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
238000009835 boiling Methods 0.000 abstract description 8
238000010521 absorption reaction Methods 0.000 abstract description 5
230000007062 hydrolysis Effects 0.000 abstract description 5
238000006460 hydrolysis reaction Methods 0.000 abstract description 5
238000009833 condensation Methods 0.000 abstract description 3
230000005494 condensation Effects 0.000 abstract description 2
238000001125 extrusion Methods 0.000 abstract description 2
238000001746 injection moulding Methods 0.000 abstract description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
-1 aromatic dicarboxylic acids Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002253 acid Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000001991 dicarboxylic acids Chemical class 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
125000005263 alkylenediamine group Chemical class 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
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
AZCPJRSLLFDOJD-UHFFFAOYSA-N 1,2-diazacyclododecane Chemical class C1CCCCCNNCCCC1 AZCPJRSLLFDOJD-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-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
HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000011261 inert gas Substances 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
239000007788 liquid Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 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
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-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
SINXHTUZCKRVOK-UHFFFAOYSA-N 2-ethyl-4-methylhexane-1,6-diamine Chemical compound CCC(CN)CC(C)CCN SINXHTUZCKRVOK-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
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
KHCHDTPQBNDGAK-UHFFFAOYSA-N 4-ethyl-2-methylhexane-1,6-diamine Chemical compound NCCC(CC)CC(C)CN KHCHDTPQBNDGAK-UHFFFAOYSA-N 0.000 description 1
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 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
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229960002684 aminocaproic acid Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
238000007872 degassing Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000009477 glass transition Effects 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
230000001771 impaired effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000000746 purification Methods 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
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1

Landscapes

Polyamides (AREA)

CA000315764A 1978-11-03 1978-11-03 Polyamides transparents Expired CA1120191A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000315764A CA1120191A (fr)	1978-11-03	1978-11-03	Polyamides transparents

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000315764A CA1120191A (fr)	1978-11-03	1978-11-03	Polyamides transparents

Publications (1)

Publication Number	Publication Date
CA1120191A true CA1120191A (fr)	1982-03-16

Family

ID=4112876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000315764A Expired CA1120191A (fr)	1978-11-03	1978-11-03	Polyamides transparents

Country Status (1)

Country	Link
CA (1)	CA1120191A (fr)

1978
- 1978-11-03 CA CA000315764A patent/CA1120191A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-16	MKEX	Expiry

Publication	Publication Date	Title
KR970002525B1 (ko)	1997-03-05	투명 폴리아미드, 그의 제조방법
US20140316062A1 (en)	2014-10-23	Polyamide containing monomer units of 1,4-butylene diamine
US5177178A (en)	1993-01-05	Amorphous copolyamide from dimer acid, aromatic dicarboxylic acid and cycloaliphatic diamine
JP5698234B2 (ja)	2015-04-08	ジアミン・ジカルボン酸塩水溶液とポリアミドの製造方法
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US4250297A (en)	1981-02-10	Transparent copolyamide from isophthalic acid reactant
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US4210742A (en)	1980-07-01	Transparent polyamides from branched chain diamine
US4210743A (en)	1980-07-01	Transparent polyamides from branched chain diamines
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CA2028304A1 (fr)	1991-04-26	Procede pour la preparation d'un polyamide aromatique traitable thermoplastiquement
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US4258177A (en)	1981-03-24	Transparent copolyamide from 1,10-disubstituted C10 diamine
CA1186844A (fr)	1985-05-07	Polyamides transparents, leur production et leur emploi en fabrication d'articles faconnes
US2865894A (en)	1958-12-23	Polyamides from dicyclohexyladipic acid
CA1120192A (fr)	1982-03-16	Polyamides aliphatiques
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