GB1031369A - New diels-alder derivatives of phosphorus-containing fulvene derivatives - Google Patents
New diels-alder derivatives of phosphorus-containing fulvene derivativesInfo
- Publication number
- GB1031369A GB1031369A GB1081464A GB1081464A GB1031369A GB 1031369 A GB1031369 A GB 1031369A GB 1081464 A GB1081464 A GB 1081464A GB 1081464 A GB1081464 A GB 1081464A GB 1031369 A GB1031369 A GB 1031369A
- Authority
- GB
- United Kingdom
- Prior art keywords
- adduct
- maleic anhydride
- prepared
- diels
- dimethylfulvene
- Prior art date
- 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
Links
- 238000005698 Diels-Alder reaction Methods 0.000 title abstract 5
- 125000003250 fulvenyl group Chemical class C1(=CC=CC1=C)* 0.000 title 1
- 150000003017 phosphorus Chemical class 0.000 title 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 abstract 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002234 fulvenes Chemical class 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 239000004848 polyfunctional curative Substances 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 229920006305 unsaturated polyester Polymers 0.000 abstract 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 abstract 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 abstract 1
- CMPLVXYOKPNUAI-UHFFFAOYSA-N 2-hydroperoxycyclohexan-1-one Chemical compound OOC1CCCCC1=O CMPLVXYOKPNUAI-UHFFFAOYSA-N 0.000 abstract 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 abstract 1
- WXACXMWYHXOSIX-UHFFFAOYSA-N 5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC=C1 WXACXMWYHXOSIX-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- AQOCRJAYPYPEAJ-CFYXSCKTSA-N but-2-ynedioic acid (Z)-2,3-dipropylbut-2-enedioic acid Chemical compound C(#CC(=O)O)C(=O)O.C(CC)/C(=C(/C(=O)O)CCC)/C(=O)O AQOCRJAYPYPEAJ-CFYXSCKTSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- -1 cyclic anhydrides Chemical class 0.000 abstract 1
- CGCFGAFKSUPQOB-UHFFFAOYSA-N dibutyl hydrogen phosphite 1,2-dimethyl-5-methylidenecyclopenta-1,3-diene Chemical compound P(OCCCC)(OCCCC)O.CC1=C(C(C=C1)=C)C CGCFGAFKSUPQOB-UHFFFAOYSA-N 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- OKKMILXYCUEVFC-UHFFFAOYSA-N diethyl hydrogen phosphite 1,2-dimethyl-5-methylidenecyclopenta-1,3-diene Chemical compound P(OCC)(OCC)O.CC1=C(C(C=C1)=C)C OKKMILXYCUEVFC-UHFFFAOYSA-N 0.000 abstract 1
- IFRXKWZJZXUFRW-UHFFFAOYSA-N dimethyl hydrogen phosphite 1,2-dimethyl-5-methylidenecyclopenta-1,3-diene Chemical compound P(OC)(OC)O.CC1=C(C(C=C1)=C)C IFRXKWZJZXUFRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical class CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002357 guanidines Chemical class 0.000 abstract 1
- 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 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 abstract 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
- C08G59/18—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
- C08G59/423—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof containing an atom other than oxygen belonging to a functional groups to C08G59/42, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/383—Cycloaliphatic 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6928—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Epoxy Resins (AREA)
Abstract
The invention comprises Diels-Alder adducts of unsaturated polycarboxylic acids, or esters or anhydrides thereof, with the phosphorus-containing fulvene derivative of Specification 1,031,370. Maleic anhydride, itaconic anhydride, citraconic anhydride, di-n-propylmaleate acetylene-dicarboxylic acid are used as dienophiles in examples.ALSO:Polyesters are prepared by conventional reaction of polyhydric alcohols with Diels-Alder adducts of ethylenically or acetylenically unsaturated polycarboxylic acids, or esters or anhydrides thereof, with adducts of compounds containing a fulvene nucleus and compounds containing a >P(O)H group or a tautomer thereof (i.e. compounds of type (RO)2P(O)H, (RO)2POH, R(RO)P(O)H, R(RO)POH, R2P(O)H and R2POH). The latter adducts are believed to contain one or more structures of type. <FORM:1031369/C3/1> (see Specification 1,031,370 in Division C2). The Diels-Alder adduct may be preformed or prepared in situ during the polyester formation. In Example (9) an unsaturated polyester is prepared from propylene glycol, maleic anhydride, phthalic anhydride and a dimethylfulvene - diethyl phosphite adduct and then copolymerized with styrene using cyclohexanone hydroperoxide as catalyst. In Example (14) an unsaturated polyester is prepared from ethylene glycol, diethylene glycol, maleic anhydride, tetrahydrofurfuryl alcohol and a preformed maleic anhydride adduct of a dimethylfurvenediethyl phosphite adduct and then copolymerized with styrene. The above Diels-Alder adducts of unsaturated polycarboxylic acid cyclic anhydrides may be used as hardeners for epoxy resins. The adduct may be preformed or prepared in situ. Conventional hardeners may also be present, many being specified including amines, guanidines, dicyandiamide, amine - formaldehyde resins, polyamides containing amino groups, isocyanates, isothiocyanates, polyhydric phenols, phenol - aldehyde resins, reaction products of Al alkoxides or phenoxides with acetoacetic ester type compounds, phosphoric acid and polycarboxylic acids and their anhydrides. In Examples, a bisphenol A-epichlorohydrin resin is cured with mixtures of: (3) benzyldimethylamine and a maleic anhydride adduct of a dimethylfulvenediethyl phosphite adduct; (11) 2,4,6 - tris - (dimethylaminomethyl) phenol and a maleic anhydride adduct of a dimethylfulvene - diallyl phosphite adduct; (13) N-benzyldimethylamine and a maleic anhydride adduct of a dimethylfulvene-di-n-butyl phosphite adduct; and (16) N-benzyldimethylamine and an itaconic anhydride adduct of a dimethylfulvene-dimethyl phosphite adduct.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1081464A GB1031369A (en) | 1964-03-13 | 1964-03-13 | New diels-alder derivatives of phosphorus-containing fulvene derivatives |
| FR8965A FR1440677A (en) | 1964-03-13 | 1965-03-12 | New compounds containing phosphorus, processes for their preparation and uses |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1081464A GB1031369A (en) | 1964-03-13 | 1964-03-13 | New diels-alder derivatives of phosphorus-containing fulvene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1031369A true GB1031369A (en) | 1966-06-02 |
Family
ID=9974774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1081464A Expired GB1031369A (en) | 1964-03-13 | 1964-03-13 | New diels-alder derivatives of phosphorus-containing fulvene derivatives |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1440677A (en) |
| GB (1) | GB1031369A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0799850A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Phosphorus modified epoxy resins and a method for their preparation |
| EP0799849A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Process for the preparation of phosphorus modified epoxy resins |
| EP0799847A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Phosphorus modified epoxy resin compositions based on epoxy resins, phosphor containing compounds and a curing agent |
-
1964
- 1964-03-13 GB GB1081464A patent/GB1031369A/en not_active Expired
-
1965
- 1965-03-12 FR FR8965A patent/FR1440677A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0799850A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Phosphorus modified epoxy resins and a method for their preparation |
| EP0799849A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Process for the preparation of phosphorus modified epoxy resins |
| EP0799847A1 (en) * | 1996-04-01 | 1997-10-08 | Hoechst Aktiengesellschaft | Phosphorus modified epoxy resin compositions based on epoxy resins, phosphor containing compounds and a curing agent |
| US5854361A (en) * | 1996-04-01 | 1998-12-29 | Hoechst Aktiengesellschaft | Process for preparing phosphorus-modified epoxy resins |
| US5880247A (en) * | 1996-04-01 | 1999-03-09 | Hoechst Aktiengesellschaft | Phosphorus-containing dicarboxylic acid (anhydride)-modified epoxy resin |
| US5959043A (en) * | 1996-04-01 | 1999-09-28 | Clariant Gmbh | Phosphorus-containing dicarboxylic reaction product of epoxy resins and phosphorus acid (anhydride) with hardener |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1440677A (en) | 1966-06-03 |
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