NO893770L - Prekatalysert materiale for omsetning med en epoksyforbindelse. - Google Patents

Prekatalysert materiale for omsetning med en epoksyforbindelse. Download PDF

Info

Publication number: NO893770L
Authority: NO; Norway
Prior art keywords: group; epoxy; value; hydrogen; carbon atoms
Prior art date: 1988-09-23

Application number

NO89893770A

Other languages

English (en)

Norwegian (no)

Other versions

NO893770D0 (no

Inventor

Ha Quoc Pham

Loan Anh Ho

Original Assignee

Dow Chemical Co

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.)

1988-09-23

Filing date

1989-09-22

Publication date

1990-03-26

1989-09-22 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1989-09-22 Publication of NO893770D0 publication Critical patent/NO893770D0/no

1990-03-26 Publication of NO893770L publication Critical patent/NO893770L/no

Links

239000004593 Epoxy Substances 0.000 title claims description 21
239000000463 material Substances 0.000 title claims description 14
239000003054 catalyst Substances 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
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 claims description 23
229920000647 polyepoxide Polymers 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 21
150000002118 epoxides Chemical class 0.000 claims description 21
239000003822 epoxy resin Substances 0.000 claims description 21
125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
150000001450 anions Chemical class 0.000 claims description 10
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
125000003700 epoxy group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
WTFXVDWCEPLDDY-UHFFFAOYSA-L triphenyl(4-triphenylphosphaniumylbutyl)phosphanium;dibromide Chemical group [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WTFXVDWCEPLDDY-UHFFFAOYSA-L 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000005496 phosphonium group Chemical group 0.000 claims description 5
229910019142 PO4 Inorganic materials 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
239000010452 phosphate Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
XIZMFZWZYVQIOX-UHFFFAOYSA-L triphenyl(5-triphenylphosphaniumylpentyl)phosphanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XIZMFZWZYVQIOX-UHFFFAOYSA-L 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000002978 peroxides Chemical class 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
239000000047 product Substances 0.000 description 14
150000008064 anhydrides Chemical class 0.000 description 11
-1 epoxide compound Chemical class 0.000 description 11
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 11
229920005989 resin Polymers 0.000 description 11
239000011347 resin Substances 0.000 description 11
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
235000013824 polyphenols Nutrition 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
XKNPLAXXMMOZLO-UHFFFAOYSA-N [O-]P([O-])([O-])=O.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [O-]P([O-])([O-])=O.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 XKNPLAXXMMOZLO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
150000001993 dienes Chemical class 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229920003986 novolac Polymers 0.000 description 4
239000000376 reactant Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 4
AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 4
POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 4
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229930185605 Bisphenol Natural products 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DUVKXNKIYKAUPK-UHFFFAOYSA-N acetic acid;triphenylphosphane Chemical compound CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 DUVKXNKIYKAUPK-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052736 halogen Chemical class 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 description 2
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 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
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
230000007306 turnover Effects 0.000 description 2
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
QLMARMBNEOBIIW-UHFFFAOYSA-N 3,4-dioctyloxolane-2,5-dione Chemical compound CCCCCCCCC1C(CCCCCCCC)C(=O)OC1=O QLMARMBNEOBIIW-UHFFFAOYSA-N 0.000 description 1
CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 description 1
RIHWJROUZAYQGA-UHFFFAOYSA-N 3-chlorooxolane-2,5-dione Chemical compound ClC1CC(=O)OC1=O RIHWJROUZAYQGA-UHFFFAOYSA-N 0.000 description 1
YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
ZJFCVUTYZHUNSW-UHFFFAOYSA-N 3-octadecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1CC(=O)OC1=O ZJFCVUTYZHUNSW-UHFFFAOYSA-N 0.000 description 1
LNYYKKTXWBNIOO-UHFFFAOYSA-N 3-oxabicyclo[3.3.1]nona-1(9),5,7-triene-2,4-dione Chemical compound C1=CC(C(=O)OC2=O)=CC2=C1 LNYYKKTXWBNIOO-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
UKVSOXGGGOPLAE-UHFFFAOYSA-N 4,7-dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound CC1C=CC(C)C2C(=O)OC(=O)C12 UKVSOXGGGOPLAE-UHFFFAOYSA-N 0.000 description 1
ZTPFKYBAGMGBRP-UHFFFAOYSA-N 4-butoxy-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound CCCCOC1C=CCC2C(=O)OC(=O)C12 ZTPFKYBAGMGBRP-UHFFFAOYSA-N 0.000 description 1
RMASCTUWOQKTPN-UHFFFAOYSA-N 4-butyl-3a,7a-dihydro-2-benzofuran-1,3-dione Chemical compound CCCCC1=CC=CC2C(=O)OC(=O)C12 RMASCTUWOQKTPN-UHFFFAOYSA-N 0.000 description 1
PBBJRMNYRDRNRI-UHFFFAOYSA-N 4-ethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound CCC1C=CCC2C(=O)OC(=O)C12 PBBJRMNYRDRNRI-UHFFFAOYSA-N 0.000 description 1
KOVAQMSVARJMPH-UHFFFAOYSA-N 4-methoxybutan-1-ol Chemical compound COCCCCO KOVAQMSVARJMPH-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
HWZRXCHJIQVTPX-UHFFFAOYSA-N acetic acid;triphenylphosphanium;acetate Chemical compound CC(O)=O.CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HWZRXCHJIQVTPX-UHFFFAOYSA-N 0.000 description 1
229940091181 aconitic acid Drugs 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001649 bromium compounds Chemical class 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
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005266 casting Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010835 comparative analysis Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000011888 foil Substances 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
NQSWKXQVCRSSDH-UHFFFAOYSA-L hydrogen carbonate;triphenyl(4-triphenylphosphaniumylbutyl)phosphanium Chemical compound OC([O-])=O.OC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NQSWKXQVCRSSDH-UHFFFAOYSA-L 0.000 description 1
JIYIFUSLSRWZJI-UHFFFAOYSA-L hydrogen carbonate;triphenyl(5-triphenylphosphaniumylpentyl)phosphanium Chemical compound OC([O-])=O.OC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JIYIFUSLSRWZJI-UHFFFAOYSA-L 0.000 description 1
LUAFHQHCMJWVBK-UHFFFAOYSA-L hydrogen carbonate;triphenyl(6-triphenylphosphaniumylhexyl)phosphanium Chemical compound OC([O-])=O.OC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LUAFHQHCMJWVBK-UHFFFAOYSA-L 0.000 description 1
YVQWVMLPQJQHBR-UHFFFAOYSA-L hydrogen carbonate;triphenyl(7-triphenylphosphaniumylheptyl)phosphanium Chemical compound OC([O-])=O.OC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YVQWVMLPQJQHBR-UHFFFAOYSA-L 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
ABGFTYJEALLDFX-UHFFFAOYSA-L oxalate;triphenyl(4-triphenylphosphaniumylbutyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ABGFTYJEALLDFX-UHFFFAOYSA-L 0.000 description 1
SISWFWZFVYNVAC-UHFFFAOYSA-L oxalate;triphenyl(5-triphenylphosphaniumylpentyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 SISWFWZFVYNVAC-UHFFFAOYSA-L 0.000 description 1
GZXLNDMOLWCQCK-UHFFFAOYSA-L oxalate;triphenyl(6-triphenylphosphaniumylhexyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GZXLNDMOLWCQCK-UHFFFAOYSA-L 0.000 description 1
WXWNXNPKFHNSAN-UHFFFAOYSA-L oxalate;triphenyl(7-triphenylphosphaniumylheptyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CCCCCCC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WXWNXNPKFHNSAN-UHFFFAOYSA-L 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000003878 thermal aging Methods 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
HVFBISAATINJPF-UHFFFAOYSA-L triphenyl(triphenylphosphaniumylmethyl)phosphanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HVFBISAATINJPF-UHFFFAOYSA-L 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Emergency Medicine (AREA)
General Chemical & Material Sciences (AREA)
Epoxy Resins (AREA)
Cable Accessories (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Insulating Bodies (AREA)

NO89893770A 1988-09-23 1989-09-22 Prekatalysert materiale for omsetning med en epoksyforbindelse. NO893770L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/248,509 US4933420A (en)	1988-09-23	1988-09-23	Epoxy resins containing phosphonium catalysts

Publications (2)

Publication Number	Publication Date
NO893770D0 NO893770D0 (no)	1989-09-22
NO893770L true NO893770L (no)	1990-03-26

Family

ID=22939462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO89893770A NO893770L (no)	1988-09-23	1989-09-22	Prekatalysert materiale for omsetning med en epoksyforbindelse.

Country Status (9)

Country	Link
US (1)	US4933420A (fr)
EP (1)	EP0360195A3 (fr)
JP (1)	JPH02163115A (fr)
KR (1)	KR900004796A (fr)
CN (1)	CN1041291A (fr)
AU (1)	AU632762B2 (fr)
BR (1)	BR8904820A (fr)
MY (1)	MY104220A (fr)
NO (1)	NO893770L (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0496828A4 (en) *	1989-10-20	1993-03-31	Isp Investments Inc.	Vinyl ethers synthesized from hydroxylated vinyl ethers and polyepoxides
CA2055833C (fr) *	1990-11-20	2001-04-24	Katsue Nishikawa	Preparation d'une resine ester epoxyde insaturee et d'une resine ester epoxyde insaturee carboxylee; composition photosensible a base de ces produits
US5401814A (en) *	1993-10-13	1995-03-28	The Dow Chemical Company	Process for the preparation of thermoplastic poly(hydroxy ethers)
US6011111A (en) *	1993-10-18	2000-01-04	The Dow Chemical Company	Hydroxy-phenoxyether polymer thermoplastic composites
CN1085702C (zh) *	1995-09-20	2002-05-29	第一工业制药株式会社	热固性树脂用阻燃剂
US6534621B2 (en)	2000-05-18	2003-03-18	Dow Global Technologies Inc.	Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom
KR100989195B1 (ko) *	2002-05-31	2010-10-20	그라세 게엠베하 운트 캄파니 카게	에스터 아마이드 축합 생성물을 포함하는 분말 코팅 소광제
US20040166241A1 (en) *	2003-02-20	2004-08-26	Henkel Loctite Corporation	Molding compositions containing quaternary organophosphonium salts
US20050288450A1 (en) *	2003-05-23	2005-12-29	Tim Fletcher	Coating matting agent comprising amide condensation product
CN103901719A (zh) *	2014-04-28	2014-07-02	无锡德贝尔光电材料有限公司	一种快干型含羧基的感光性树脂及其制备方法
US12180362B1 (en)	2023-06-23	2024-12-31	ACS Technical Products, Inc.	Liquid binder compositions and uses thereof
US11965087B1 (en)	2023-06-23	2024-04-23	ACS Technical Products, Inc.	Liquid binder compositions and uses thereof

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3477990A (en) *	1967-12-07	1969-11-11	Shell Oil Co	Process for reacting a phenol with an epoxy compound and resulting products
US3948855A (en) *	1971-09-16	1976-04-06	The Dow Chemical Company	Process for reacting a phenol with a vicinal epoxy compound in the presence of phosphorus or carbon containing acid, ester or acid ester
US4177216A (en) *	1974-06-21	1979-12-04	The Dow Chemical Company	Novel tributyl (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts
US4171420A (en) *	1974-06-21	1979-10-16	The Dow Chemical Company	Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids
CA1041696A (fr) *	1974-06-21	1978-10-31	George A. Doorakian	Catalyseurs latents favorisant la reaction des epoxydes en presence de phenols ou d'acides carboxyliques
US4093650A (en) *	1976-04-23	1978-06-06	The Dow Chemical Company	Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosphonium salts
US4192939A (en) *	1976-09-20	1980-03-11	Chevron Research Company	Phosphonium catalyst system for the polymerization of 2-pyrrolidone
US4171422A (en) *	1978-09-11	1979-10-16	Allied Chemical Corporation	Production of thermally stabilized polyester
US4302574A (en) *	1979-05-23	1981-11-24	The Dow Chemical Company	Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
US4266079A (en) *	1979-11-05	1981-05-05	The Dow Chemical Company	Process for preparing tetrahydrocarbylphosphonium bicarbonate salts
US4395574A (en) *	1980-05-12	1983-07-26	The Dow Chemical Co.	Phosphonium phenoxide catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids
US4340761A (en) *	1980-11-24	1982-07-20	The Dow Chemical Company	Preparation of phosphonium phenoxide salts
US4370465A (en) *	1980-12-04	1983-01-25	The Dow Chemical Co.	Epoxy resins having improved physical properties when cured
US4352918A (en) *	1980-12-04	1982-10-05	The Dow Chemical Company	Process for preparing epoxy resins having improved physical properties when cured using quaternary phosphonium catalysts
US4354015A (en) *	1981-02-05	1982-10-12	The Dow Chemical Company	Phosphonium bicarbonate catalysts for promoting reaction of epoxides with phenols
US4366295A (en) *	1981-06-01	1982-12-28	The Dow Chemical Company	Stable precatalyzed epoxy resin compositions
US4410496A (en) *	1982-05-07	1983-10-18	The United States Of America As Represented By The Secretary Of The Interior	Recovery of metal values from complex sulfides
US4496709A (en) *	1982-06-23	1985-01-29	The Dow Chemical Company	Process for preparing epoxy resins employing a phosphonium trifluoroacetate catalyst
EP0111562A4 (fr) *	1982-06-23	1984-10-16	Dow Chemical Co	Procede de preparation de resines epoxydes avancees utilisant un catalyseur au trifluoroacetate de phosphonium.
US4405766A (en) *	1982-07-30	1983-09-20	The Dow Chemical Company	Phosphonium bicarbonate catalysts for promoting reaction of epoxides with carboxylic acids or anhydrides
US4438254A (en) *	1983-02-28	1984-03-20	The Dow Chemical Company	Process for producing epoxy resins
US4477645A (en) *	1983-07-21	1984-10-16	The Dow Chemical Company	Immobilized epoxy advancement initiators
US4540823A (en) *	1983-07-21	1985-09-10	The Dow Chemical Company	Tetrahydrocarbyl phosphonium salts
US4594291A (en) *	1984-07-17	1986-06-10	The Dow Chemical Company	Curable, partially advanced epoxy resins
US4634757A (en) *	1985-07-15	1987-01-06	Shell Oil Company	Fusion product
US4692504A (en) *	1986-04-30	1987-09-08	Shell Oil Company	Deactivation of phosphonium salt catalyst
US4732958A (en) *	1986-12-30	1988-03-22	Shell Oil Company	Epoxy fusion process
US4808692A (en) *	1988-02-18	1989-02-28	The Dow Chemical Company	Preparation of advanced epoxy resins from epoxy resins and dihydric phenols in the presence of phosphonium compounds

1988
- 1988-09-23 US US07/248,509 patent/US4933420A/en not_active Expired - Fee Related
1989
- 1989-09-14 JP JP1237426A patent/JPH02163115A/ja active Pending
- 1989-09-18 EP EP19890117230 patent/EP0360195A3/fr not_active Withdrawn
- 1989-09-20 BR BR898904820A patent/BR8904820A/pt not_active Application Discontinuation
- 1989-09-22 AU AU41696/89A patent/AU632762B2/en not_active Ceased
- 1989-09-22 KR KR1019890013620A patent/KR900004796A/ko not_active Withdrawn
- 1989-09-22 CN CN89107426A patent/CN1041291A/zh active Pending
- 1989-09-22 MY MYPI89001309A patent/MY104220A/en unknown
- 1989-09-22 NO NO89893770A patent/NO893770L/no unknown

Also Published As

Publication number	Publication date
EP0360195A2 (fr)	1990-03-28
KR900004796A (ko)	1990-04-13
BR8904820A (pt)	1990-05-01
CN1041291A (zh)	1990-04-18
EP0360195A3 (fr)	1991-10-23
US4933420A (en)	1990-06-12
MY104220A (en)	1994-02-28
JPH02163115A (ja)	1990-06-22
AU632762B2 (en)	1993-01-14
AU4169689A (en)	1990-03-29
NO893770D0 (no)	1989-09-22

Publication	Publication Date	Title
US4302574A (en)	1981-11-24	Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
CA1147741A (fr)	1983-06-07	Phenoxydes de phosphonium utilises comme catalyseurs dans les reactions entre les epoxy et les phenols et (ou) les acides carboxyliques
US3824212A (en)	1974-07-16	Process for preparing higher molecular weight polyepoxide products by reacting a polyepoxide with a phenol in presence of tetraalkylammonium halides
NO893770L (no)	1990-03-26	Prekatalysert materiale for omsetning med en epoksyforbindelse.
US4395574A (en)	1983-07-26	Phosphonium phenoxide catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids
US4632971A (en)	1986-12-30	Thermally stable capped thermoplastic phenolic resin
US4981926A (en)	1991-01-01	Composition of epoxy resin, amino group-containing phosphonium catalyst and curing agent
US3978027A (en)	1976-08-31	Process for reacting a phenol with an epoxy compound
EP0157854B1 (fr)	1989-09-06	Ethers de polyglycidyle de novolacs ramifies
WO2008045882A1 (fr)	2008-04-17	Polymères soluble à forte conversion of d'acide de résines époxy aromatiques et de diacides et revêtements réticulés en étant faits
US5202407A (en)	1993-04-13	Precatalyzed catalyst compositions, process for preparing epoxy resins curable compositions, articles resulting from curing the resultant compositions
EP0189480B1 (fr)	1988-07-20	Procede d'amelioration de l'utilite de resines epoxy
US5208317A (en)	1993-05-04	Composition comprising epoxy resin and cationic amine phosphonium catalyst
US3842037A (en)	1974-10-15	Process for preparing higher molecular weight polyepoxide products by condensing lower molecular weight polyepoxide with polyhydric phenols
US5019639A (en)	1991-05-28	Novel epoxy resins
JP5662343B2 (ja)	2015-01-28	ヒドロキシル官能性ポリエーテル及びその製造方法
US4340713A (en)	1982-07-20	Method for preparing high molecular weight epoxy resins containing hydrolyzed epoxy groups
KR970002661B1 (ko)	1997-03-07	변형 에폭시 수지의 제조방법 및 에폭시 수지 표면 코우팅 조성물
US4713404A (en)	1987-12-15	Paint formulation comprising a thermally stable capped thermoplastic phenolic resin
WO2009064707A1 (fr)	2009-05-22	Procédé de préparation de résines époxy modernes
EP0065564A4 (fr)	1983-03-29	Procede de preparation de resines epoxy de poids moleculaire eleve contenant des groupes glycidyle hydrolyses.
US5145919A (en)	1992-09-08	Epoxy resin compositions based on alkoxylated phenols
JPH08100047A (ja)	1996-04-16	新規のエポキシ樹脂、その製法および用途
EP0443351A2 (fr)	1991-08-28	Compositions de combinaisons chimiques des groupements hydroxy phénoliques,latentes,durcissables,catalysées,contenant des combinaisons chimiques ou des complexes prÀ©parées,par contact des phosphines ou arsines organiques avec des acides nucléophiles faible
NO166041B (no)	1991-02-11	Varmestabil, termoplastisk fenolharpiks og anvendelse derav.