GB968849A - Mixed esters of naphthenic and acyclic carboxylic acids - Google Patents
Mixed esters of naphthenic and acyclic carboxylic acidsInfo
- Publication number
- GB968849A GB968849A GB3677160A GB3677160A GB968849A GB 968849 A GB968849 A GB 968849A GB 3677160 A GB3677160 A GB 3677160A GB 3677160 A GB3677160 A GB 3677160A GB 968849 A GB968849 A GB 968849A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- naphthenate
- esters
- naphthenic
- acyclic
- 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
- 150000002148 esters Chemical class 0.000 title abstract 13
- -1 acyclic carboxylic acids Chemical class 0.000 title abstract 7
- 239000002253 acid Substances 0.000 abstract 8
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 abstract 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 229920001577 copolymer Polymers 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 125000005608 naphthenic acid group Chemical group 0.000 abstract 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 239000005642 Oleic acid Substances 0.000 abstract 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000002015 acyclic group Chemical group 0.000 abstract 3
- 230000032050 esterification Effects 0.000 abstract 3
- 238000005886 esterification reaction Methods 0.000 abstract 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 3
- 125000005609 naphthenate group Chemical group 0.000 abstract 3
- 229920001291 polyvinyl halide Polymers 0.000 abstract 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 3
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 abstract 2
- IMYZYCNQZDBZBQ-UHFFFAOYSA-M 9,10-epoxyoctadecanoate Chemical compound CCCCCCCCC1OC1CCCCCCCC([O-])=O IMYZYCNQZDBZBQ-UHFFFAOYSA-M 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 2
- 229920001519 homopolymer Polymers 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- 229940043375 1,5-pentanediol Drugs 0.000 abstract 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- BHHYHSUAOQUXJK-UHFFFAOYSA-L Zinc fluoride Inorganic materials F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 abstract 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 abstract 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 150000002238 fumaric acids Chemical class 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical class CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 abstract 1
- 235000020778 linoleic acid Nutrition 0.000 abstract 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 abstract 1
- 229940049964 oleate Drugs 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 abstract 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
-
- 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
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention comprises mixed esters of formula: <FORM:0968849/C1/1> in which X is hydrogen or an -OR3 group, G is a residue of a polyhydric alcohol having 2 hydroxyl groups when X is hydrogen and 3 hydroxyl groups when X is -OR3, and R1 and R2 and R3 are each residues of a naphthenic acid or an acyclic aliphatic monocarboxylic acid, at least one of R1, R2 and R3 being a naphthenic acid residue and at least one an acyclic aliphatic monocarboxylic acid residue. A mixture of esters may be prepared in which 20 to 80% of the R1, R2 and R3 residues are naphthenic acid residues and the balance is composed of acyclic aliphatic carboxylic acid residues. The acyclic acid residues each contain more than 4 carbon atoms, or, when a mixture of acids is used in the esterification, an average of more than 4 carbon atoms. The esters are prepared by esterification of the polyhydric alcohol, naphthenic acid and acyclic acid at 100 DEG to 300 DEG C. in the presence of a catalyst e.g. toluene sulphonic acid, benzene sulphonic acid, alkanesulphonic acid, alkali metal hydrogen sulphate, hydrochloric acid, sulphuric acid, zinc chloride, metallic zinc and boron fluoride, and a solvent, e.g. toluene, xylene, heptane, octane, kerosene and mineral oil. Esters in which unsaturated acid residues are present may be epoxidized by contact at 25 DEG to 50 DEG C. with a peracid e.g. perbenzoic or peracetic acid in a solvent; or with hydrogen peroxide in acetic acid. The mixed esters may be used to plasticize polyvinyl halide homopolymers and copolymers. In examples 4-(2-methylvaleroxy) butyl naphthenate is prepared from tetramethylene glycol, naphthenic acid and 2-methylpentanoic acid; 4-isovaleroxylbutyl naphthenate is prepared from tetramethylene glycol and naphthenic and isovaleric acids; 3-caproyloxypropyl naphthenate is prepared from trimethylene glycol and naphthenic and caprylic acids; 2-naphthenoxymethyl - 2 - heptanoyloxymethyl propyloleate is prepared from oleic acid, naphthenic acid, heptanoic acid and trimethylolethane and is epoxidized to naphthenoxymethyl-2-heptanoyloxymethyl-propyl 9, 10-epoxystearate, and substituting linoleic acid for oleic acid 2 - naphthenoxymethyl - 2 - heptanoyloxymethylpropyl 7, 8, 10, 11-diepoxystearate is obtained; naphthenoxypentyl oleate is obtained from oleic acid, naphthenic acid and 1, 5-pentanediol and epoxidized to naphthenoxypentyl 9, 10-epoxystearate. Other esters mentioned are 3-stearyloxypropyl naphthenate, 2(2-methylbutyroxymethyl)-2-methylpropyl naphthenate, 3-isobutyroxyethoxyethyl naphthenate and 2, 2-diethyl-3-valeroxypropyl naphthenate. Lists of suitable dihydric and trihydric alcohols and of acyclic monocarboxylic acids are given.ALSO:Plasticizers for polyvinyl halide polymers and copolymers comprise esters of formula: <FORM:0968849/C3/1> in which X is hydrogen or an -OR3 group, G is a residue of a polyhydric alcohol having 2 hydroxyl groups when X is hydrogen and 3 hydroxyl groups when X is -OR3, and R1 and R2 and R3 are each residue of a naphthenic acid or an acyclic aliphatic monocarboxylic acid, at least one of R1, R2 and R3 being a naphthenic acid residue and at least one an acyclic aliphatic monocarboxylic acid residues. A mixture of esters may be used in which 20 to 80% of the R1, R2 and R3 residues are naphthenic acid residues and the balance is composed of acyclic aliphatic carboxylic acid residues. The acyclic acid residues each contain more than 4 carbon atoms, or, when a mixture of acids is used in the esterification, an average of more than 4 carbon atoms. Esters prepared from unsaturated acids may be epoxidized. The mixed esters are used to plasticize polyvinyl halide homopolymers and copolymers in amounts of 5 to 100 parts by weight of polymer. The ester is mixed with powdered resin and then heated at 150 DEG to 200 DEG C. In examples 4-(2-methyl-valeroxy) butyl naphthenate, 4-isovaleroxylbutyl naphthenate, 3-caproyloxypropyl naphthenate, 2-naphthenoxymethyl-2-heptanoyloxymethyl-propyl 9, 10-epoxystearate, 2-naphthenoxymethyl-2-heptanoyloxymethyl-propyl 7, 8, 10, 11-diepoxystearate, and naphthenoxypentyl 9, 10-epoxystearate are used to plasticize polyvinyl chloride and polyvinyl chloride-polyvinyl acetate copolymers. Other esters mentioned are 3-stearyloxypropyl naphthenate, 2(2-methylbutyroxymethyl)-2-methyl-propyl naphthenate, 3-isobutyroxy-ethoxyethyl naphthenate and 2, 2-diethyl-3-valeroxypropyl naphthenate. Other copolymers mentioned are prepared from vinyl chloride with vinylidene chloride, methyl acrylate, vinyl isobutyl ether, vinyl propionate, vinyl butyrate, vinyl benzoate, ethyl acrylate, propyl acrylate, butyl acrylate, acrylamide, acrylonitrile, styrene, chlorostyrene, ethyl styrene, vinyl naphthalene, alkyl esters of maleic, crotonic, itaconic and fumaric acids, vinyl alkyl ketones, vinyl pyridine, and isobutylene. Lists of suitable dihydric and trihydric alcohols and of acyclic monocarboxylic acids are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84914959A | 1959-10-28 | 1959-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB968849A true GB968849A (en) | 1964-09-02 |
Family
ID=25305178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3677160A Expired GB968849A (en) | 1959-10-28 | 1960-10-26 | Mixed esters of naphthenic and acyclic carboxylic acids |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE596534A (en) |
| GB (1) | GB968849A (en) |
| NL (1) | NL257307A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021113365A1 (en) * | 2019-12-06 | 2021-06-10 | Guide Therapeutics, Inc. | Nanomaterials |
| US12268753B2 (en) | 2021-01-20 | 2025-04-08 | Beam Therapeutics Inc. | Nanomaterials comprising a biodegradable feature |
| US12296053B2 (en) | 2022-07-20 | 2025-05-13 | Beam Therapeutics Inc. | Nanomaterials comprising triols |
| US12435035B2 (en) | 2020-01-09 | 2025-10-07 | Guide Therapeutics, Llc | Nanomaterials |
-
0
- NL NL257307D patent/NL257307A/xx unknown
-
1960
- 1960-10-26 GB GB3677160A patent/GB968849A/en not_active Expired
- 1960-10-28 BE BE596534A patent/BE596534A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021113365A1 (en) * | 2019-12-06 | 2021-06-10 | Guide Therapeutics, Inc. | Nanomaterials |
| JP2023505316A (en) * | 2019-12-06 | 2023-02-08 | ガイド セラピューティクス，エルエルシー | nanomaterials |
| US12435035B2 (en) | 2020-01-09 | 2025-10-07 | Guide Therapeutics, Llc | Nanomaterials |
| US12268753B2 (en) | 2021-01-20 | 2025-04-08 | Beam Therapeutics Inc. | Nanomaterials comprising a biodegradable feature |
| US12296053B2 (en) | 2022-07-20 | 2025-05-13 | Beam Therapeutics Inc. | Nanomaterials comprising triols |
Also Published As
| Publication number | Publication date |
|---|---|
| NL257307A (en) | |
| BE596534A (en) | 1961-04-28 |
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