GB1319367A - Process for stabilising homo-or copolymeric polyolefins with diacyl dihydrazides - Google Patents
Process for stabilising homo-or copolymeric polyolefins with diacyl dihydrazidesInfo
- Publication number
- GB1319367A GB1319367A GB1555871*[A GB1555871A GB1319367A GB 1319367 A GB1319367 A GB 1319367A GB 1555871 A GB1555871 A GB 1555871A GB 1319367 A GB1319367 A GB 1319367A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- dihydrazide
- chlorides
- hydrazide
- chloride
- 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
- 229920000098 polyolefin Polymers 0.000 title abstract 2
- 229920001577 copolymer Polymers 0.000 title 1
- 229920001519 homopolymer Polymers 0.000 title 1
- 230000003019 stabilising effect Effects 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 abstract 5
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 3
- -1 monocarboxylic acid chlorides Chemical class 0.000 abstract 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 abstract 2
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical class ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 abstract 2
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 abstract 2
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 abstract 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 2
- BDFXCSNFIZEINQ-UHFFFAOYSA-N 2,2,3-trimethylhexanedihydrazide Chemical compound NNC(=O)C(C)(C)C(C)CCC(=O)NN BDFXCSNFIZEINQ-UHFFFAOYSA-N 0.000 abstract 1
- WODNPPQTZHQXTN-UHFFFAOYSA-N 2,2,3-trimethylhexanedioyl dichloride Chemical class ClC(=O)C(C)(C)C(C)CCC(Cl)=O WODNPPQTZHQXTN-UHFFFAOYSA-N 0.000 abstract 1
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 abstract 1
- WOTFFLFEMKUWOF-UHFFFAOYSA-N 2-ethylhexanehydrazide Chemical compound CCCCC(CC)C(=O)NN WOTFFLFEMKUWOF-UHFFFAOYSA-N 0.000 abstract 1
- MNRANHOFCOLOSG-UHFFFAOYSA-N 2-n-benzoylethanedihydrazide Chemical compound NNC(=O)C(=O)N(N)C(=O)C1=CC=CC=C1 MNRANHOFCOLOSG-UHFFFAOYSA-N 0.000 abstract 1
- AIPCSKRJJOUNEM-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoyl chloride Chemical compound CC(C)(C)C1=CC(C(Cl)=O)=CC(C(C)(C)C)=C1O AIPCSKRJJOUNEM-UHFFFAOYSA-N 0.000 abstract 1
- KMWIPXLIKIAZMT-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanehydrazide Chemical compound CC(C)(C)C1=CC(CCC(=O)NN)=CC(C(C)(C)C)=C1O KMWIPXLIKIAZMT-UHFFFAOYSA-N 0.000 abstract 1
- QQWPLVSLXJSGMO-UHFFFAOYSA-N 4-octoxybenzohydrazide Chemical compound CCCCCCCCOC1=CC=C(C(=O)NN)C=C1 QQWPLVSLXJSGMO-UHFFFAOYSA-N 0.000 abstract 1
- YXBOJGHBKKAPOG-UHFFFAOYSA-N 4-octoxybenzoyl chloride Chemical class CCCCCCCCOC1=CC=C(C(Cl)=O)C=C1 YXBOJGHBKKAPOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000005643 Pelargonic acid Substances 0.000 abstract 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 abstract 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical class COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 abstract 1
- ALHNLFMSAXZKRC-UHFFFAOYSA-N benzene-1,4-dicarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C=C1 ALHNLFMSAXZKRC-UHFFFAOYSA-N 0.000 abstract 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 abstract 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004188 dichlorophenyl group Chemical group 0.000 abstract 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical class CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 abstract 1
- GNHGCDCAOUNOCA-UHFFFAOYSA-N naphthalene-2,6-dicarbohydrazide Chemical compound C1=C(C(=O)NN)C=CC2=CC(C(=O)NN)=CC=C21 GNHGCDCAOUNOCA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004957 naphthylene group Chemical group 0.000 abstract 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical class CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine
- C08K5/25—Carboxylic acid hydrazides
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH737170A CH529803A (de) | 1970-05-19 | 1970-05-19 | Verwendung von Diacyldihydraziden als Stabilisatoren für Polyolefine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1319367A true GB1319367A (en) | 1973-06-06 |
Family
ID=4324077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1555871*[A Expired GB1319367A (en) | 1970-05-19 | 1971-05-18 | Process for stabilising homo-or copolymeric polyolefins with diacyl dihydrazides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3734885A (enExample) |
| JP (1) | JPS508097B1 (enExample) |
| AT (1) | AT304875B (enExample) |
| CA (1) | CA970091A (enExample) |
| CH (1) | CH529803A (enExample) |
| DE (1) | DE2124641A1 (enExample) |
| ES (1) | ES391307A1 (enExample) |
| FR (1) | FR2091804A5 (enExample) |
| GB (1) | GB1319367A (enExample) |
| NL (1) | NL7106826A (enExample) |
| SU (1) | SU481161A3 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038247A (en) * | 1970-05-19 | 1977-07-26 | Ciba-Geigy Corporation | Stabilizing polyolefins with diacyl dihydrazides |
| US3894990A (en) * | 1971-05-06 | 1975-07-15 | Ciba Geigy Corp | Stabilization of homo-or copolymeric polyolefins with diacyl dihydrazides |
| US3907925A (en) * | 1973-10-10 | 1975-09-23 | Ciba Geigy Corp | Metal deactivators as adhesion promotors for vulcanizable elastomers to metals |
| US3994987A (en) * | 1973-10-10 | 1976-11-30 | Ciba-Geigy Corporation | Metal deactivators as adhesion promotors for vulcanizable elastomers to metals |
| US3888825A (en) * | 1973-10-19 | 1975-06-10 | American Cyanamid Co | Copper inhibitors for polyolefins |
| US4012360A (en) * | 1973-12-03 | 1977-03-15 | Ciba-Geigy Corporation | Bis-salicyloyl-dicarboxylic acid dihydrazides as stabilizers for polyolefines |
| JPS542226B2 (enExample) * | 1973-12-31 | 1979-02-03 | ||
| US3951911A (en) * | 1974-04-26 | 1976-04-20 | Dart Industries Inc. | Stabilized propylene-based polymer compositions |
| US3931103A (en) * | 1974-10-18 | 1976-01-06 | American Cyanamid Company | Copper inhibitors for polyolefins |
| US4035325A (en) * | 1975-06-16 | 1977-07-12 | Standard Oil Company (Indiana) | Use of organometallic salts and metal deactivators as flame retardants for polyolefins |
| US4077948A (en) * | 1975-07-30 | 1978-03-07 | Ciba-Geigy Corporation | Metal deactivators as adhesion promotors for vulcanizable elastomers to metals |
| US4061845A (en) * | 1976-11-04 | 1977-12-06 | The General Tire & Rubber Company | Copolymers of hydrazides and certain unsaturated esters |
| US4087405A (en) * | 1977-08-26 | 1978-05-02 | Eastman Kodak Company | Polyhydrazides as stabilizers for polyolefins |
| US4145556A (en) * | 1977-12-21 | 1979-03-20 | Monsanto Company | Oxamide stabilizers for organic materials |
| US4154723A (en) * | 1977-12-21 | 1979-05-15 | Monsanto Company | Stabilization of organic materials |
| DE2933870A1 (de) * | 1979-08-21 | 1981-03-12 | Siemens AG, 1000 Berlin und 8000 München | N.n'-bis-salicyloyl-hydrazin als metalldesaktivator. |
| US4874803A (en) * | 1987-09-21 | 1989-10-17 | Pennwalt Corporation | Dianhydride coupled polymer stabilizers |
| EP0333643A3 (de) * | 1988-02-12 | 1990-01-31 | Ciba-Geigy Ag | Stabilisierte Zusammensetzungen |
| JP5461952B2 (ja) * | 2009-10-23 | 2014-04-02 | 株式会社Ａｄｅｋａ | ポリオレフィン系樹脂組成物 |
| CN102976969B (zh) * | 2012-11-27 | 2015-04-29 | 山西省化工研究所 | 一种提高脂肪二羧酸二酰肼类成核剂收率的制备方法 |
| WO2016209663A1 (en) * | 2015-06-22 | 2016-12-29 | 3M Innovative Properties Company | Hydrazide compounds suitable for nucleating polylactic acid polymer |
| CN117106237B (zh) * | 2023-07-05 | 2024-03-26 | 湖南联塑科技实业有限公司 | 一种复合改性剂及其聚丙烯组合物 |
-
1970
- 1970-05-19 CH CH737170A patent/CH529803A/de not_active IP Right Cessation
-
1971
- 1971-05-06 US US00141027A patent/US3734885A/en not_active Expired - Lifetime
- 1971-05-17 SU SU1658619A patent/SU481161A3/ru active
- 1971-05-18 ES ES391307A patent/ES391307A1/es not_active Expired
- 1971-05-18 JP JP46033550A patent/JPS508097B1/ja active Pending
- 1971-05-18 CA CA113,252A patent/CA970091A/en not_active Expired
- 1971-05-18 NL NL7106826A patent/NL7106826A/xx unknown
- 1971-05-18 GB GB1555871*[A patent/GB1319367A/en not_active Expired
- 1971-05-18 DE DE19712124641 patent/DE2124641A1/de active Pending
- 1971-05-18 AT AT430371A patent/AT304875B/de active
- 1971-05-19 FR FR7118213A patent/FR2091804A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES391307A1 (es) | 1974-11-16 |
| CA970091A (en) | 1975-06-24 |
| SU481161A3 (ru) | 1975-08-15 |
| NL7106826A (enExample) | 1971-11-23 |
| AT304875B (de) | 1973-01-25 |
| CH529803A (de) | 1972-10-31 |
| FR2091804A5 (enExample) | 1972-01-14 |
| JPS508097B1 (enExample) | 1975-04-02 |
| US3734885A (en) | 1973-05-22 |
| DE2124641A1 (de) | 1971-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |