KR20200107765A - 생물원성 탄소를 함유하는 베타-프로피오락톤 기반 공중합체, 이의 제조 방법 및 이의 용도 - Google Patents
생물원성 탄소를 함유하는 베타-프로피오락톤 기반 공중합체, 이의 제조 방법 및 이의 용도 Download PDFInfo
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- KR20200107765A KR20200107765A KR1020197019455A KR20197019455A KR20200107765A KR 20200107765 A KR20200107765 A KR 20200107765A KR 1020197019455 A KR1020197019455 A KR 1020197019455A KR 20197019455 A KR20197019455 A KR 20197019455A KR 20200107765 A KR20200107765 A KR 20200107765A
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- South Korea
- Prior art keywords
- copolymer
- beta
- bio
- bpl
- propiolactone
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- 229960000380 propiolactone Drugs 0.000 title claims abstract description 125
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 title claims abstract description 117
- 238000000034 method Methods 0.000 title claims abstract description 31
- 229920001577 copolymer Polymers 0.000 title claims description 87
- 229910052799 carbon Inorganic materials 0.000 title description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 30
- 230000000975 bioactive effect Effects 0.000 title description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- -1 cyclic anhydride Chemical class 0.000 claims description 45
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 40
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 40
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 38
- 238000005810 carbonylation reaction Methods 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 38
- 239000012620 biological material Substances 0.000 claims description 32
- 230000006315 carbonylation Effects 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003180 beta-lactone group Chemical group 0.000 claims description 17
- 125000000129 anionic group Chemical group 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 9
- 239000012038 nucleophile Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 150000002892 organic cations Chemical class 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- AKOCEYFZOKYBJF-UHFFFAOYSA-N (4-oxooxetan-2-yl)methyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CC(=O)O1 AKOCEYFZOKYBJF-UHFFFAOYSA-N 0.000 claims description 3
- WGNAUWVQWMSSEV-UHFFFAOYSA-N 3-pentyloxiran-2-one Chemical compound CCCCCC1OC1=O WGNAUWVQWMSSEV-UHFFFAOYSA-N 0.000 claims description 3
- YCHZSCVAUUOEPV-UHFFFAOYSA-N 3-undecyloxiran-2-one Chemical compound CCCCCCCCCCCC1OC1=O YCHZSCVAUUOEPV-UHFFFAOYSA-N 0.000 claims description 3
- TVKAZUMAUBFYLC-UHFFFAOYSA-N 4-(butoxymethyl)oxetan-2-one Chemical compound CCCCOCC1CC(=O)O1 TVKAZUMAUBFYLC-UHFFFAOYSA-N 0.000 claims description 3
- LJGWCBXPHFKHGC-UHFFFAOYSA-N 4-(prop-2-enoxymethyl)oxetan-2-one Chemical compound C=CCOCC1CC(=O)O1 LJGWCBXPHFKHGC-UHFFFAOYSA-N 0.000 claims description 3
- ILZULEZGLISUPE-UHFFFAOYSA-N 4-[[tert-butyl(dimethyl)silyl]oxymethyl]oxetan-2-one Chemical compound CC(C)(C)[Si](C)(C)OCC1CC(=O)O1 ILZULEZGLISUPE-UHFFFAOYSA-N 0.000 claims description 3
- QTWLQDVFHKLZRA-UHFFFAOYSA-N 4-ethyloxetan-2-one Chemical compound CCC1CC(=O)O1 QTWLQDVFHKLZRA-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical group CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- FQIKTQAWBZYCKD-UHFFFAOYSA-N 2-heptadecylpropane-1,2,3-triol Chemical compound CCCCCCCCCCCCCCCCCC(O)(CO)CO FQIKTQAWBZYCKD-UHFFFAOYSA-N 0.000 claims description 2
- AAIKVJNVKVXSKJ-UHFFFAOYSA-N 4-but-3-enyloxetan-2-one Chemical compound C=CCCC1CC(=O)O1 AAIKVJNVKVXSKJ-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 229920005684 linear copolymer Polymers 0.000 claims 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 description 35
- 239000000047 product Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 239000003505 polymerization initiator Substances 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 125000000623 heterocyclic group Chemical group 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000002685 polymerization catalyst Substances 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 8
- 150000002596 lactones Chemical class 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 239000002028 Biomass Substances 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 6
- 229920001169 thermoplastic Polymers 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229940048053 acrylate Drugs 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010977 unit operation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 230000000035 biogenic effect Effects 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
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- 238000004806 packaging method and process Methods 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- DGUTXSBBNRQOKD-UHFFFAOYSA-M prop-2-enoate trimethyl(phenyl)azanium Chemical compound [O-]C(=O)C=C.C[N+](C)(C)c1ccccc1 DGUTXSBBNRQOKD-UHFFFAOYSA-M 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- DLSULYIQRAZOPW-UHFFFAOYSA-M trimethyl(phenyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C1=CC=CC=C1 DLSULYIQRAZOPW-UHFFFAOYSA-M 0.000 description 3
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical group CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6882—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
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| PCT/US2018/016853 WO2018144998A1 (en) | 2016-12-05 | 2018-02-05 | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
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| KR20200107765A true KR20200107765A (ko) | 2020-09-16 |
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| WO2015184289A1 (en) | 2014-05-30 | 2015-12-03 | Novomer Inc. | Integrated methods for chemical synthesis |
| JP6670011B2 (ja) | 2014-07-25 | 2020-03-18 | ノボマー， インコーポレイテッド | 金属錯体の合成およびその使用 |
| US20180029005A1 (en) | 2015-02-13 | 2018-02-01 | Novomer, Inc. | Flexible chemical production platform |
| MA41514A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédés intégrés de synthèse chimique |
| MA41507A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production de polymères |
| EP3256441B1 (en) | 2015-02-13 | 2020-04-08 | Novomer, Inc. | Continuous carbonylation processes |
| MA41510A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Procédé de production d'acide acrylique |
| MA41508A (fr) | 2015-02-13 | 2017-12-19 | Novomer Inc | Systèmes et procédés de production d'acide polyacrylique |
| BR112018002143A2 (pt) | 2015-07-31 | 2018-09-18 | Novomer Inc | sistema de produção/processo de produção para ácido acrílico e precursores do mesmo |
| AU2017236914A1 (en) | 2016-03-21 | 2018-11-08 | Novomer, Inc. | Improved acrylic acid production process |
| MA46720A (fr) | 2016-11-02 | 2019-09-11 | Novomer Inc | Polymères absorbants, procédés et systèmes de production et utilisations correspondantes |
| US10144802B2 (en) | 2016-12-05 | 2018-12-04 | Novomer, Inc. | Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof |
| US10500104B2 (en) | 2016-12-06 | 2019-12-10 | Novomer, Inc. | Biodegradable sanitary articles with higher biobased content |
| US10065914B1 (en) | 2017-04-24 | 2018-09-04 | Novomer, Inc. | Thermolysis of polypropiolactone to produce acrylic acid |
| US10676426B2 (en) | 2017-06-30 | 2020-06-09 | Novomer, Inc. | Acrylonitrile derivatives from epoxide and carbon monoxide reagents |
| US10590099B1 (en) | 2017-08-10 | 2020-03-17 | Novomer, Inc. | Processes for producing beta-lactone with heterogenous catalysts |
| JP7676023B2 (ja) | 2018-07-13 | 2025-05-14 | ノボマー， インコーポレイテッド | ポリラクトン発泡体及びその製造方法 |
| US11498894B2 (en) | 2019-03-08 | 2022-11-15 | Novomer, Inc. | Integrated methods and systems for producing amide and nitrile compounds |
| CN115989254A (zh) | 2020-08-17 | 2023-04-18 | 诺沃梅尔公司 | β丙内酯和官能化β丙内酯系聚合物体系 |
| EP4323425A1 (en) * | 2021-04-16 | 2024-02-21 | Novomer, Inc. | Polypropiolactones and methods of preparation |
| WO2023275619A1 (en) * | 2021-06-29 | 2023-01-05 | Bostik Sa | Poly (3 -hydroxyacid) polymers from long-chain epoxides and their uses related to hot melt adhesives |
| WO2023003890A1 (en) * | 2021-07-21 | 2023-01-26 | Novomer, Inc. | Methods for beta-lactone copolymerization |
| WO2024141770A1 (en) * | 2022-12-28 | 2024-07-04 | Bostik Sa | Poly(3-hydroxyacid) polymers from long-chain epoxides and their uses related to hot melt adhesives |
| CN116444715A (zh) * | 2023-03-08 | 2023-07-18 | 浙江卫星新材料科技有限公司 | 一种可完全生物降解高吸收性树脂的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3169945A (en) | 1956-04-13 | 1965-02-16 | Union Carbide Corp | Lactone polyesters |
| BE639062A (enExample) * | 1962-10-25 | |||
| US3607841A (en) * | 1967-03-22 | 1971-09-21 | Kanegafuchi Spinning Co Ltd | Production of poly-2,2-disubstituted-beta-propiolactones |
| GB1182376A (en) * | 1968-07-01 | 1970-02-25 | Shell Int Research | Process for the Polymerization or Copolymerization of Beta-Propiolactones |
| US3678069A (en) | 1968-12-04 | 1972-07-18 | Phillips Petroleum Co | Lactone polymerization with a dicarboxylic acid-water initiator |
| JPS5986621A (ja) * | 1982-11-10 | 1984-05-18 | Daicel Chem Ind Ltd | 新規なグラフト重合体の製造方法 |
| PL160092B1 (pl) * | 1989-05-15 | 1993-02-26 | Sposób wytwarzania makromonomerów poliestrowych PL | |
| US5032671A (en) * | 1990-09-04 | 1991-07-16 | Arco Chemical Technology, Inc. | Preparation of lactone polymers using double metal cyanide catalysts |
| US5310948A (en) | 1992-06-29 | 1994-05-10 | Shell Oil Company | Carbonylation of epoxides |
| US5349046A (en) * | 1992-12-01 | 1994-09-20 | Shell Oil Company | Polymerization of β-lactones under rim conditions |
| AU703280B2 (en) | 1994-01-28 | 1999-03-25 | Procter & Gamble Company, The | Polymerization of beta-substituted-beta-propiolactones initiated by alkylzinc alkoxides |
| US6133402A (en) | 1998-08-04 | 2000-10-17 | Cornell Research Foundation, Inc. | Polycarbonates made using high activity catalysts |
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| EP3548538A1 (en) | 2019-10-09 |
| US20180155491A1 (en) | 2018-06-07 |
| US10669373B2 (en) | 2020-06-02 |
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| BR112019011536A2 (pt) | 2019-10-08 |
| MA46978A (fr) | 2019-10-09 |
| US11655333B2 (en) | 2023-05-23 |
| CO2019005773A2 (es) | 2019-06-19 |
| US20190071538A1 (en) | 2019-03-07 |
| WO2018144998A1 (en) | 2018-08-09 |
| AU2018215539A1 (en) | 2019-06-20 |
| CA3046104A1 (en) | 2018-08-09 |
| EP3548538B1 (en) | 2022-07-27 |
| JP2021506987A (ja) | 2021-02-22 |
| US20200262973A1 (en) | 2020-08-20 |
| CN110352209A (zh) | 2019-10-18 |
| MX2019006524A (es) | 2019-10-22 |
| US10144802B2 (en) | 2018-12-04 |
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