EP3612589A2 - Dérivé de glycérol pour applications polymères - Google Patents
Dérivé de glycérol pour applications polymèresInfo
- Publication number
- EP3612589A2 EP3612589A2 EP18787413.6A EP18787413A EP3612589A2 EP 3612589 A2 EP3612589 A2 EP 3612589A2 EP 18787413 A EP18787413 A EP 18787413A EP 3612589 A2 EP3612589 A2 EP 3612589A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- thermoplastic elastomer
- compound
- formula
- sealant
- acyl group
- 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
- 150000002314 glycerols Chemical class 0.000 title claims abstract description 11
- 229920000642 polymer Polymers 0.000 title claims description 13
- 229920002725 thermoplastic elastomer Polymers 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000001924 fatty-acyl group Chemical group 0.000 claims abstract description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 16
- 239000000565 sealant Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 7
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical group C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000654 additive Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- -1 glycerin ester Chemical class 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KZVIUXKOLXVBPC-UHFFFAOYSA-N 16-methylheptadecanamide Chemical compound CC(C)CCCCCCCCCCCCCCC(N)=O KZVIUXKOLXVBPC-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000012206 bottled water Nutrition 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- TWXPKKOLCJDQBY-UHFFFAOYSA-N 6-octadecanoyloxyhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCOC(=O)CCCCCCCCCCCCCCCCC TWXPKKOLCJDQBY-UHFFFAOYSA-N 0.000 description 1
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical group CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 1
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 101000693847 Homo sapiens Peroxisome biogenesis factor 2 Proteins 0.000 description 1
- 102100025516 Peroxisome biogenesis factor 2 Human genes 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- JUYLAWDTPWXGNH-UHFFFAOYSA-N butanedioic acid hexane-1,1-diol Chemical compound C(CCC(=O)O)(=O)O.C(CCC(=O)O)(=O)O.C(CCCCC)(O)O JUYLAWDTPWXGNH-UHFFFAOYSA-N 0.000 description 1
- LFURZEMGYHMXPJ-UHFFFAOYSA-N butanedioic acid;octadecanoic acid Chemical compound OC(=O)CCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O LFURZEMGYHMXPJ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical group CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
Definitions
- thermoplastic polymer compositions comprising a compound with formula
- R 1 , R 2 and R 3 is a branched chain acyl group consisting of a saturated chain having 10 to 20 carbon atoms and a hydrophilic branch group; wherein the compound of the invention is used as a plasticizer and the thermoplastic polymer is or comprises a vinyl chloride polymer or a vinyl chloride copolymer and a copolymer prepared by grafting vinyl chloride onto ethylene/vinyl acetate copolymer and mixtures thereof.
- the '466 publication does not disclose the glycerol derivative or a polyglycerol of the present invention and its polymer applications.
- 2016/058927 (referred to herein as '927 publication, assigned to M/s DuPont Nutrition Biosciences) claims a polymer composition comprising polyethylene terphthalate) and polyglycerol fatty acid ester as an internal additive wherein the composition enables reduced torque during processing and reduced surface friction during its use as a packaging material.
- the '927 publication does not disclose use of the polyglycerol fatty acid ester in thermoplastic elastomers.
- the object of the present invention is to provide thermoplastic elastomer compositions which enable reduced opening torque.
- R 1 , R 2 and R 3 represent each an acyl group or a hydrogen atom, said acyl group comprises at least one with 2 carbon atoms and one with more than 12 carbon atoms.
- thermoplastic elastomer comprising 0.1 to 0.596 of a polyglycerol, compound of formula II,
- R 1 , R 2 and R 3 represent each a fatty acyl group, said fatty acyl group comprises at least 12 carbon atoms.
- thermoplastic elastomers sometimes referred to as thermoplastic rubbers have been created as an alternative to natural rubber are a class of copolymers or a physical mixture of polymers (usually a plastic and a rubber) which consists of materials with both thermoplastic and elastomeric properties.
- Thermoplastic elastomers have the properties and performance of rubber but are processed like plastic.
- TPEs are flexible materials with varied applications such as in sealants, molded flexible parts and adhesives for use in automobile manufacturing, food packaging and allied . industries.
- thermoplastic elastomers Various additives are added to thermoplastic elastomers to improve its performance such as plasticizers, colorants, flavours, torque reducing agents, coefficient of friction reducing agents etc.
- thermoplastic elastomers with torque reducing agent compound of formula I, which is a glycerol derivative.
- thermoplastic elastomer comprising a glycerol derivative, compound of formula I,
- R 1 , R 2 and R 3 represent each an acyl group or a hydrogen atom, said acyl group comprises at least one with 2 carbon atoms and one with more than 12 carbon atoms.
- the compound of formula I may be used in about 0.1 to 196, preferably 0.1 to 0.5%, most preferred being about 0.2596 by weight of the polymer.
- thermoelastic elastomer of the present invention may be ethylene vinyl acetate.
- the thermoelastic elastomer of the present invention may be used as a sealant for liquid containers.
- the glycerol derivative of the present invention enables the opening torque of the sealant for liquid containers to be reduced by at least 5096.
- the glycerol derivative of the present invention also retains the organoleptic properties of the liquid.
- the glycerol derivative of the present invention does not scuff the seal during opening of the liquid container.
- a Thermoplastic elastomer comprising a polyglycerol, compound of formula II,
- R 1 R 2 and R 3 represent each a fatty acyl group, said fatty acyl -group comprises at least 12 carbon atoms.
- the compound of formula II may be used in about 0.1 to 196, preferably 0.1 to 0.596, most preferred being about 0.2596 by weight of the polymer.
- thermoplastic elastomer of the present invention may be used as a sealant for liquid containers.
- the polyglycerol of the present invention enables the opening torque of the sealant for liquid containers to be reduced by at least 50%.
- the polyglycerol of the present invention does not scuff the seal during opening of the liquid container.
- torque release is the moment of a force tending to cause rotation of an appropriate closure in a direction opposite to that of closing, causing the closure to be unsecured from its position on the neck finish of an appropriate container.
- Coefficient of friction is the ratio of the force required to move one surface over another to the total force applied normal to those surfaces.
- Finawax-B is behenamide
- Finaslip - EZY is mixture of linear saturated fatty amide(s) and glycerol monostearate
- Finaslip - PEX2 is an ester additive prepared from a 1,3-propanediol and succinic acid
- EV-4 is hexanediol disuccinate
- EV-5 is hexanediol mixed ester of stearate-succinate
- EV-6 is hexanediol distearate
- EV-7 is polyglycerol fatty acid ester
- EV-8 is acetyl ester of monoglycerin fatty acid ester
- EV-9 is Polyglycerol Stearate
- Release or opening torque Measurement Firmly position the bottle in the holder. Fix the fixer containing test cap to the bottle (avoid contact with bottle). Position the torque meter with needle to left hand side & rotate clockwise slowly, at constant rate, until the desired/predetermined constant torque (called as closing torque) is indicated on the needle. Keeping the torque meter in its place, bring the needle to the right hand side and rotate anticlockwise, slowly avoiding contact with the container. The torque indicated by needle is release or opening torque of the closure.
- Film to Metal measurement Position the test film or sheet specimen to the platform (stainless steel plane). Smoothen the film specimen, gently with your fingers, to eliminate wrinkles. Attach the filament to the sled & lightly place the sled in position on the test specimen. Start the test & calculate the CoF with the help of attached software.
- test specimens at 23 ⁇ 2" C and 50 ⁇ 5 % relative humidity.
- Example 1 Torque. Coefficient of Friction
- Dosage level 2000 ppm.
- Compression Molding at 105'C, thickness 0.7mm (water cooling).
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)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN201721013879 | 2017-04-19 | ||
PCT/IN2018/000023 WO2018193462A2 (fr) | 2017-04-19 | 2018-04-19 | Dérivé de glycérol pour applications polymères |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3612589A2 true EP3612589A2 (fr) | 2020-02-26 |
EP3612589A4 EP3612589A4 (fr) | 2021-01-13 |
Family
ID=63855630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18787413.6A Pending EP3612589A4 (fr) | 2017-04-19 | 2018-04-19 | Dérivé de glycérol pour applications polymères |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP3612589A4 (fr) |
WO (1) | WO2018193462A2 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10557025B2 (en) | 2015-05-07 | 2020-02-11 | Fine Organics Industries Pvt Ltd. | Polypropylene cap or film composition |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5832647A (ja) * | 1981-08-21 | 1983-02-25 | Riken Vitamin Co Ltd | 熱可塑性樹脂組成物 |
US6147148A (en) * | 1997-09-02 | 2000-11-14 | Ajinomoto Co., Inc. | Thermal-aging resistant thermoplastic resin composition comprising a dibasic acid erythritol ester, and resin molded article obtained therefrom |
JP2001151969A (ja) * | 1999-11-24 | 2001-06-05 | Riken Vinyl Industry Co Ltd | ゾル用塩化ビニル系樹脂組成物 |
JP5344742B2 (ja) * | 2008-08-01 | 2013-11-20 | 株式会社Adeka | 難燃性熱可塑性樹脂組成物 |
GB201418452D0 (en) * | 2014-10-17 | 2014-12-03 | Dupont Nutrition Biosci Aps | Additive |
US10370516B2 (en) * | 2015-02-19 | 2019-08-06 | Fine Organics Industries Pvt Ltd. | Bio based plasticizer with improved properties and processing characteristics of polymer |
US10557025B2 (en) * | 2015-05-07 | 2020-02-11 | Fine Organics Industries Pvt Ltd. | Polypropylene cap or film composition |
EP3245864A1 (fr) * | 2016-05-20 | 2017-11-22 | Akzo Nobel Chemicals International B.V. | Agent antibuée |
-
2018
- 2018-04-19 EP EP18787413.6A patent/EP3612589A4/fr active Pending
- 2018-04-19 WO PCT/IN2018/000023 patent/WO2018193462A2/fr unknown
Also Published As
Publication number | Publication date |
---|---|
WO2018193462A2 (fr) | 2018-10-25 |
WO2018193462A3 (fr) | 2018-12-06 |
EP3612589A4 (fr) | 2021-01-13 |
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Ipc: C08K 5/103 20060101AFI20201207BHEP Ipc: C08K 5/00 20060101ALI20201207BHEP Ipc: C08L 23/08 20060101ALI20201207BHEP Ipc: F16J 15/00 20060101ALI20201207BHEP |
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