CA1072240A - Epoxide thermal stabilization additive for polypyrrolidone - Google Patents
Epoxide thermal stabilization additive for polypyrrolidoneInfo
- Publication number
- CA1072240A CA1072240A CA289,609A CA289609A CA1072240A CA 1072240 A CA1072240 A CA 1072240A CA 289609 A CA289609 A CA 289609A CA 1072240 A CA1072240 A CA 1072240A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- composition
- epoxyalkyl
- weight
- epoxide
- 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
- 229920001007 Nylon 4 Polymers 0.000 title claims abstract description 10
- 230000006641 stabilisation Effects 0.000 title abstract description 4
- 238000011105 stabilization Methods 0.000 title abstract description 4
- 239000000654 additive Substances 0.000 title abstract 2
- 230000000996 additive effect Effects 0.000 title 1
- 150000002118 epoxides Chemical class 0.000 title 1
- -1 Alkyl epoxides Chemical class 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 235000020778 linoleic acid Nutrition 0.000 claims 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 2
- 235000021313 oleic acid Nutrition 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 238000001125 extrusion Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- IMYZYCNQZDBZBQ-SJORKVTESA-N (9S,10R)-epoxyoctadecanoic acid Chemical compound CCCCCCCC[C@H]1O[C@H]1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-SJORKVTESA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 101150049479 CCNC gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VUSHVKUNOXWQTG-KHPPLWFESA-N methyl (Z)-2-oxooctadec-9-enoate Chemical compound O=C(C(=O)OC)CCCCCC\C=C/CCCCCCCC VUSHVKUNOXWQTG-KHPPLWFESA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IIGMITQLXAGZTL-UHFFFAOYSA-N octyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCC IIGMITQLXAGZTL-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- 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
- C08K5/04—Oxygen-containing compounds
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- G—PHYSICS
- G07—CHECKING-DEVICES
- G07D—HANDLING OF COINS OR VALUABLE PAPERS, e.g. TESTING, SORTING BY DENOMINATIONS, COUNTING, DISPENSING, CHANGING OR DEPOSITING
- G07D11/00—Devices accepting coins; Devices accepting, dispensing, sorting or counting valuable papers
- G07D11/10—Mechanical details
- G07D11/12—Containers for valuable papers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Artificial Filaments (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/752,502 US4071486A (en) | 1976-12-20 | 1976-12-20 | Epoxide thermal stabilization additive for polypyrrolidone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072240A true CA1072240A (en) | 1980-02-19 |
Family
ID=25026578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,609A Expired CA1072240A (en) | 1976-12-20 | 1977-10-26 | Epoxide thermal stabilization additive for polypyrrolidone |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4071486A (https=) |
| JP (1) | JPS5378254A (https=) |
| AU (1) | AU508999B2 (https=) |
| BE (1) | BE860448A (https=) |
| CA (1) | CA1072240A (https=) |
| DE (1) | DE2755188C3 (https=) |
| ES (1) | ES465253A1 (https=) |
| FR (1) | FR2374380A1 (https=) |
| GB (1) | GB1577588A (https=) |
| IT (1) | IT1089415B (https=) |
| MX (1) | MX5480E (https=) |
| NL (1) | NL7714135A (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261881A (en) * | 1979-05-07 | 1981-04-14 | Chevron Research Company | Poly-2-pyrrolidone composition having improved stability and method of extruding |
| US4383065A (en) * | 1980-12-29 | 1983-05-10 | Chevron Research Company | Stabilized polypyrrolidone composition |
| DE3508531A1 (de) * | 1985-03-09 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Hydrophobierte, leichtfliessende thermoplastische polyamide |
| CH665424A5 (de) * | 1985-05-15 | 1988-05-13 | Inventa Ag | Thermoplastische polyamidformmassen mit verminderter wasseraufnahme. |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2996474A (en) * | 1955-04-27 | 1961-08-15 | Onderzoekings Inst Res | Process of molding a mixture of at least two fiber forming linear condensation products, at least one of which products contains a high temperature thickening agent |
| US3052654A (en) * | 1957-11-08 | 1962-09-04 | Minnesota Mining & Mfg | Stabilized polypyrrolidone |
| US3017393A (en) * | 1958-01-27 | 1962-01-16 | Minnesota Mining & Mfg | Stabilization of polymers of pyrrolidone |
| DE1271286C2 (de) * | 1962-02-09 | 1973-03-01 | Metallgesellschaft Ag | Pulverfoermiges Kunststoffueberzugsmittel |
| DE1495714A1 (de) * | 1963-04-03 | 1969-07-03 | Bayer Ag | Verfahren zum Herstellen von Schmelzen hochmolekularer Polyamide mit besonders hoher Standfestigkeit |
| US3406140A (en) * | 1964-01-09 | 1968-10-15 | Celanese Corp | Polyurethane composition containing an epoxy compound as a stabilizer |
| FR1450977A (fr) * | 1964-10-31 | 1966-06-24 | Bayer Ag | Procédé de préparation de polyamides réticulées à haut poids moléculaire |
| GB1251377A (https=) * | 1968-04-16 | 1971-10-27 | ||
| US3721652A (en) * | 1970-09-03 | 1973-03-20 | Radiation Res Corp | Polymers of 2-pyrrolidone |
| US3948832A (en) * | 1974-09-25 | 1976-04-06 | Atlantic Richfield Company | Stabilized ethylene-carbon monoxide copolymers containing an epoxy compound |
-
1976
- 1976-12-20 US US05/752,502 patent/US4071486A/en not_active Expired - Lifetime
-
1977
- 1977-10-10 AU AU29526/77A patent/AU508999B2/en not_active Expired
- 1977-10-26 CA CA289,609A patent/CA1072240A/en not_active Expired
- 1977-11-03 BE BE182325A patent/BE860448A/xx not_active IP Right Cessation
- 1977-12-07 GB GB51036/77A patent/GB1577588A/en not_active Expired
- 1977-12-10 DE DE2755188A patent/DE2755188C3/de not_active Expired
- 1977-12-13 FR FR7737548A patent/FR2374380A1/fr active Granted
- 1977-12-14 JP JP15042277A patent/JPS5378254A/ja active Granted
- 1977-12-19 IT IT30893/77A patent/IT1089415B/it active
- 1977-12-20 ES ES465253A patent/ES465253A1/es not_active Expired
- 1977-12-20 NL NL7714135A patent/NL7714135A/xx not_active Application Discontinuation
-
1978
- 1978-01-02 MX MX786749U patent/MX5480E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5378254A (en) | 1978-07-11 |
| ES465253A1 (es) | 1978-09-16 |
| IT1089415B (it) | 1985-06-18 |
| MX5480E (es) | 1983-08-19 |
| AU508999B2 (en) | 1980-04-17 |
| BE860448A (fr) | 1978-03-01 |
| FR2374380B1 (https=) | 1981-10-02 |
| AU2952677A (en) | 1979-04-26 |
| GB1577588A (en) | 1980-10-29 |
| JPS5546668B2 (https=) | 1980-11-25 |
| FR2374380A1 (fr) | 1978-07-13 |
| DE2755188C3 (de) | 1980-09-04 |
| DE2755188B2 (de) | 1980-01-10 |
| NL7714135A (nl) | 1978-06-22 |
| DE2755188A1 (de) | 1978-06-22 |
| US4071486A (en) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |