DE1188802B - Herstellen von Formteilen aus halogenhaltigen Polyester-Formmassen - Google Patents
Herstellen von Formteilen aus halogenhaltigen Polyester-FormmassenInfo
- Publication number
- DE1188802B DE1188802B DEC25678A DEC0025678A DE1188802B DE 1188802 B DE1188802 B DE 1188802B DE C25678 A DEC25678 A DE C25678A DE C0025678 A DEC0025678 A DE C0025678A DE 1188802 B DE1188802 B DE 1188802B
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- unsaturated
- molded parts
- compounds
- molding compounds
- 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.)
- Pending
Links
- 229910052736 halogen Inorganic materials 0.000 title claims description 25
- 150000002367 halogens Chemical class 0.000 title claims description 25
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 238000000465 moulding Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229920000728 polyester Polymers 0.000 title description 12
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 12
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229920006305 unsaturated polyester Polymers 0.000 description 4
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- -1 tetrachlorophthalic acid diallyl ester Chemical class 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- LQZDDWKUQKQXGC-UHFFFAOYSA-N 2-(2-methylprop-2-enoxymethyl)oxirane Chemical compound CC(=C)COCC1CO1 LQZDDWKUQKQXGC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-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
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VGBCZZOFIFDLBS-UHFFFAOYSA-N (1,2,3-trichloro-1-chlorooxy-3-hydroxy-1-phenylpropan-2-yl) hypochlorite Chemical compound ClC(C(C(OCl)(C1=CC=CC=C1)Cl)(OCl)Cl)O VGBCZZOFIFDLBS-UHFFFAOYSA-N 0.000 description 1
- PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 description 1
- BJQFWAQRPATHTR-UHFFFAOYSA-N 1,2-dichloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1Cl BJQFWAQRPATHTR-UHFFFAOYSA-N 0.000 description 1
- IZMZREOTRMMCCB-UHFFFAOYSA-N 1,4-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=C(Cl)C(C=C)=C1 IZMZREOTRMMCCB-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 description 1
- UNQWKAVGUZNMJZ-UHFFFAOYSA-N 2,3-dibromoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(Br)=C1Br UNQWKAVGUZNMJZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- INZKZPADNLPBRW-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalaldehyde Chemical compound ClC1=C(Cl)C(Cl)=C(C=O)C(C=O)=C1Cl INZKZPADNLPBRW-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- YUDBKSANIWMLCU-UHFFFAOYSA-N 3,4-dichlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1C(O)=O YUDBKSANIWMLCU-UHFFFAOYSA-N 0.000 description 1
- LANDRZNMJOEVQO-UHFFFAOYSA-N 3-ethenoxypropane-1,2-diol Chemical compound OCC(O)COC=C LANDRZNMJOEVQO-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- UDCSURCKPULYEL-UHFFFAOYSA-N 4,6-dibromobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(Br)C=C1Br UDCSURCKPULYEL-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 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 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229950003761 loprodiol Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6828—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE625698D BE625698A (instruction) | 1961-12-06 | ||
| DEC25678A DE1188802B (de) | 1961-12-06 | 1961-12-06 | Herstellen von Formteilen aus halogenhaltigen Polyester-Formmassen |
| GB44621/62A GB960556A (en) | 1961-12-06 | 1962-11-26 | Flame-resistant unsaturated polyester resins |
| US241543A US3236916A (en) | 1961-12-06 | 1962-12-03 | Flame resistant unsaturated polyesters of the diels-alder adduct of hexachlorocyclopentadiene and an unsaturated glycidyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC25678A DE1188802B (de) | 1961-12-06 | 1961-12-06 | Herstellen von Formteilen aus halogenhaltigen Polyester-Formmassen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1188802B true DE1188802B (de) | 1965-03-11 |
Family
ID=7017945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC25678A Pending DE1188802B (de) | 1961-12-06 | 1961-12-06 | Herstellen von Formteilen aus halogenhaltigen Polyester-Formmassen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3236916A (instruction) |
| BE (1) | BE625698A (instruction) |
| DE (1) | DE1188802B (instruction) |
| GB (1) | GB960556A (instruction) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH569759A5 (instruction) * | 1972-07-04 | 1975-11-28 | Ciba Geigy Ag | |
| US4029848A (en) * | 1976-01-21 | 1977-06-14 | The Dow Chemical Company | Unsaturated polyester resins containing a dicyclopentadiene concentrate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1135621A (fr) * | 1955-11-17 | 1957-05-02 | Bayer Ag | Procédé de production de matières plastiques incombustibles ou difficilement inflammables |
| DE1012458B (de) * | 1952-09-10 | 1957-07-18 | Hooker Electrochemical Co | Zu einem Harz mit verminderter Entflammbarkeit durch Erhitzen oder katalytisch haertbare Polyesterharzmasse |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA569634A (en) * | 1959-01-27 | C. Shokal Edward | Polyhydroxy-substituted polyesters, their preparations and compositions containing the same | |
| US2822340A (en) * | 1955-10-12 | 1958-02-04 | American Cyanamid Co | Flame resistant polyester resinous compositions containing combined halogens and phosphorous and certain alkaline earth metal salts and the process of preparing the same |
| US2890144A (en) * | 1957-01-24 | 1959-06-09 | Hooker Chemical Corp | Composition comprising a vinyl monomer and a polyester of a polyhydric alcohol, an unsaturated acid, a saturated acid and a hexahalocyclopentadiene adduct and laminated article containing same |
-
0
- BE BE625698D patent/BE625698A/xx unknown
-
1961
- 1961-12-06 DE DEC25678A patent/DE1188802B/de active Pending
-
1962
- 1962-11-26 GB GB44621/62A patent/GB960556A/en not_active Expired
- 1962-12-03 US US241543A patent/US3236916A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1012458B (de) * | 1952-09-10 | 1957-07-18 | Hooker Electrochemical Co | Zu einem Harz mit verminderter Entflammbarkeit durch Erhitzen oder katalytisch haertbare Polyesterharzmasse |
| FR1135621A (fr) * | 1955-11-17 | 1957-05-02 | Bayer Ag | Procédé de production de matières plastiques incombustibles ou difficilement inflammables |
Also Published As
| Publication number | Publication date |
|---|---|
| GB960556A (en) | 1964-06-10 |
| US3236916A (en) | 1966-02-22 |
| BE625698A (instruction) |
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