CA1265299A - Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques - Google Patents

Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques

Info

Publication number: CA1265299A
Authority: CA; Canada
Prior art keywords: bis; poly; phenolic; carbon atoms; bicyclic amide
Prior art date: 1986-09-11
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

CA000518005A

Other languages

English (en)

Inventor

Anil B. Goel

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.)

Ashland LLC

Original Assignee

Ashland Oil Inc

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.)

1986-09-11

Filing date

1986-09-11

Publication date

1990-01-30

1986-09-11 Application filed by Ashland Oil Inc filed Critical Ashland Oil Inc

1986-09-11 Priority to CA000518005A priority Critical patent/CA1265299A/fr

1990-01-30 Application granted granted Critical

1990-01-30 Publication of CA1265299A publication Critical patent/CA1265299A/fr

Status Expired legal-status Critical Current

Links

DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract description 21
239000000463 material Substances 0.000 title claims abstract description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 11
239000000203 mixture Substances 0.000 title claims description 11
-1 Poly (ether amide Chemical class 0.000 title abstract description 19
238000006243 chemical reaction Methods 0.000 title abstract description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 6
229920000642 polymer Polymers 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 18
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 13
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000008442 polyphenolic compounds Polymers 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229920001568 phenolic resin Polymers 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
229920001169 thermoplastic Polymers 0.000 abstract description 5
229920001187 thermosetting polymer Polymers 0.000 abstract description 5
239000002131 composite material Substances 0.000 abstract description 3
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
239000004416 thermosoftening plastic Substances 0.000 abstract description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000002411 thermogravimetry Methods 0.000 description 12
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
230000004580 weight loss Effects 0.000 description 9
229920005989 resin Polymers 0.000 description 7
239000011347 resin Substances 0.000 description 7
229930185605 Bisphenol Natural products 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
235000013824 polyphenols Nutrition 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
AOAOYRLNGJEVTB-UHFFFAOYSA-N [3-(4,5-dihydro-1,3-oxazole-2-carbonyl)phenyl]-(4,5-dihydro-1,3-oxazol-2-yl)methanone Chemical compound C=1C=CC(C(=O)C=2OCCN=2)=CC=1C(=O)C1=NCCO1 AOAOYRLNGJEVTB-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 2
QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical class OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940106691 bisphenol a Drugs 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229960004337 hydroquinone Drugs 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
238000002156 mixing Methods 0.000 description 2
PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 2
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
LGCMKPRGGJRYGM-UHFFFAOYSA-N Osalmid Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1O LGCMKPRGGJRYGM-UHFFFAOYSA-N 0.000 description 1
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000001743 benzylic group Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
YKOQAAJBYBTSBS-UHFFFAOYSA-N biphenyl-2,3-diol Chemical class OC1=CC=CC(C=2C=CC=CC=2)=C1O YKOQAAJBYBTSBS-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
WGHKKEJHRMUKDK-UHFFFAOYSA-N cyclohexa-2,5-dien-1-one Chemical compound O=C1C=CCC=C1 WGHKKEJHRMUKDK-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000005027 hydroxyaryl group Chemical group 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
QXSAKPUBHTZHKW-UHFFFAOYSA-N para-hydroxybenzamide Natural products NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
229960001553 phloroglucinol Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000765 poly(2-oxazolines) Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920003987 resole Polymers 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000004072 triols Chemical class 0.000 description 1

Landscapes

Polyamides (AREA)
Phenolic Resins Or Amino Resins (AREA)
Epoxy Resins (AREA)

CA000518005A 1986-09-11 1986-09-11 Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques Expired CA1265299A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000518005A CA1265299A (fr)	1986-09-11	1986-09-11	Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000518005A CA1265299A (fr)	1986-09-11	1986-09-11	Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques

Publications (1)

Publication Number	Publication Date
CA1265299A true CA1265299A (fr)	1990-01-30

Family

ID=4133912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000518005A Expired CA1265299A (fr)	1986-09-11	1986-09-11	Composition a base de poly(ether-amide) obtenue par reaction d'amide-acetal bis- ou poly-bicyclique avec des composes bis- ou poly-phenoliques

Country Status (1)

Country	Link
CA (1)	CA1265299A (fr)

1986
- 1986-09-11 CA CA000518005A patent/CA1265299A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1994-07-30	MKLA	Lapsed

Publication	Publication Date	Title
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US4430491A (en)	1984-02-07	Poly(ether-amide) polymeric compositions
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US4613662A (en)	1986-09-23	Process for catalytic preparation of poly(ether-amide) polymeric composition from oxazoline and polyphenol
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JP3874089B2 (ja)	2007-01-31	熱硬化性ｐｐｅのオリゴマー体
US2965611A (en)	1960-12-20	Polyphenol glycidyl ethers
EP0260338B1 (fr)	1990-07-11	Compositions de polyétheramides à partir d'acétals d'amide bicycliques et de composés bi- et polyphénoliques
US3558560A (en)	1971-01-26	Composition consisting of novolac resins and aromatic polycarboxylic compounds
US4675371A (en)	1987-06-23	Thermoset polymeric composition from poly-oxazoline and alkenyl phosphonic acid
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US4775737A (en)	1988-10-04	Thermoset polymeric composition from poly(oxazoline), alkenyl phosphonic acid and polyphenolic
US4746719A (en)	1988-05-24	Rapid preparation of polyetheramide from bis-oxazoline, polyphenol and carbonium ion salt catalyst
EP0451405A1 (fr)	1991-10-16	Composition thermodurcissable de rÀ©sine
US5102972A (en)	1992-04-07	Polyhydric phenol chain extenders for certain bismaleimide resin