DE1694550B2 - Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau - Google Patents
Stabilisierung linearer Polyester oder Copolyester gegen WärmeabbauInfo
- Publication number
- DE1694550B2 DE1694550B2 DE1694550A DEK0064097A DE1694550B2 DE 1694550 B2 DE1694550 B2 DE 1694550B2 DE 1694550 A DE1694550 A DE 1694550A DE K0064097 A DEK0064097 A DE K0064097A DE 1694550 B2 DE1694550 B2 DE 1694550B2
- Authority
- DE
- Germany
- Prior art keywords
- polyester
- copolyesters
- acid
- against heat
- stabilization
- 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.)
- Ceased
Links
- 229920000728 polyester Polymers 0.000 title claims description 22
- 229920001634 Copolyester Polymers 0.000 title claims description 9
- 230000015556 catabolic process Effects 0.000 title claims description 3
- 238000006731 degradation reaction Methods 0.000 title claims description 3
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000003381 stabilizer Substances 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 10
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 8
- 239000001639 calcium acetate Substances 0.000 claims description 8
- 235000011092 calcium acetate Nutrition 0.000 claims description 8
- 229960005147 calcium acetate Drugs 0.000 claims description 8
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 12
- -1 threads Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-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
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- QXKPLZDCTKREIA-UHFFFAOYSA-N diphenoxy(phenyl)phosphane Chemical compound C=1C=CC=CC=1OP(C=1C=CC=CC=1)OC1=CC=CC=C1 QXKPLZDCTKREIA-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000012447 hatching Effects 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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 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
- 239000002994 raw material 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000009044 synergistic interaction Effects 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1694550A DE1694550B2 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
| NL6816729A NL6816729A (enExample) | 1967-12-04 | 1968-11-22 | |
| US780571A US3595835A (en) | 1967-12-04 | 1968-12-02 | Thermostabilized linear polyesters or copolyesters |
| BE724857D BE724857A (enExample) | 1967-12-04 | 1968-12-03 | |
| GB57353/68A GB1248769A (en) | 1967-12-04 | 1968-12-03 | Improvements in and relating to thermostabilized linear polyesters and copolyesters |
| LU57458D LU57458A1 (enExample) | 1967-12-04 | 1968-12-04 | |
| FR1594012D FR1594012A (enExample) | 1967-12-04 | 1968-12-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1694550A DE1694550B2 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1694550A1 DE1694550A1 (de) | 1971-07-15 |
| DE1694550B2 true DE1694550B2 (de) | 1979-06-07 |
Family
ID=7231452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1694550A Ceased DE1694550B2 (de) | 1967-12-04 | 1967-12-04 | Stabilisierung linearer Polyester oder Copolyester gegen Wärmeabbau |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3595835A (enExample) |
| BE (1) | BE724857A (enExample) |
| DE (1) | DE1694550B2 (enExample) |
| FR (1) | FR1594012A (enExample) |
| GB (1) | GB1248769A (enExample) |
| LU (1) | LU57458A1 (enExample) |
| NL (1) | NL6816729A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2253207C2 (de) * | 1971-11-01 | 1982-10-28 | General Electric Co., Schenectady, N.Y. | Flammhemmende thermoplastische Polyesterformmassen |
| JPS5123564A (ja) * | 1974-08-21 | 1976-02-25 | Sumitomo Chemical Co | Netsuanteiseihoriariirenesuterusoseibutsu |
| US4098741A (en) * | 1976-09-30 | 1978-07-04 | Basf Wyandotte Corporation | Phosphorus-containing polyester and size compositions |
| US4250281A (en) * | 1979-03-21 | 1981-02-10 | Eastman Kodak Company | Melt process for preparing copolyesters using triarylphosphine catalysts |
| US4619007A (en) * | 1982-09-29 | 1986-10-28 | Echevarria Angel M | Cellular waterbed component and method of manufacture |
| US8791223B2 (en) * | 2010-10-08 | 2014-07-29 | Ppg Industries Ohio, Inc. | Curable compositions and methods of catalyzing chemical reactions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437046A (en) * | 1943-10-15 | 1948-03-02 | Resinous Prod & Chemical Co | Stabilization of polyesters |
| BE552781A (enExample) * | 1955-11-23 | |||
| NL279733A (enExample) * | 1961-06-21 | |||
| US3300440A (en) * | 1964-03-02 | 1967-01-24 | Goodyear Tire & Rubber | Polyester resins stabilized with thiophosphate esters |
| US3361846A (en) * | 1964-07-09 | 1968-01-02 | Goodyear Tire & Rubber | Phenolic phosphate and phosphite esters as stabilizers for saturated polyester resins |
-
1967
- 1967-12-04 DE DE1694550A patent/DE1694550B2/de not_active Ceased
-
1968
- 1968-11-22 NL NL6816729A patent/NL6816729A/xx unknown
- 1968-12-02 US US780571A patent/US3595835A/en not_active Expired - Lifetime
- 1968-12-03 GB GB57353/68A patent/GB1248769A/en not_active Expired
- 1968-12-03 BE BE724857D patent/BE724857A/xx not_active IP Right Cessation
- 1968-12-04 FR FR1594012D patent/FR1594012A/fr not_active Expired
- 1968-12-04 LU LU57458D patent/LU57458A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1248769A (en) | 1971-10-06 |
| LU57458A1 (enExample) | 1970-06-04 |
| BE724857A (enExample) | 1969-06-03 |
| NL6816729A (enExample) | 1969-06-06 |
| FR1594012A (enExample) | 1970-06-01 |
| US3595835A (en) | 1971-07-27 |
| DE1694550A1 (de) | 1971-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |