JPS6225121A - ポリグリコリドまたはポリラクチドの製造方法 - Google Patents
ポリグリコリドまたはポリラクチドの製造方法Info
- Publication number
- JPS6225121A JPS6225121A JP16465585A JP16465585A JPS6225121A JP S6225121 A JPS6225121 A JP S6225121A JP 16465585 A JP16465585 A JP 16465585A JP 16465585 A JP16465585 A JP 16465585A JP S6225121 A JPS6225121 A JP S6225121A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- molecular weight
- polycondensate
- reaction
- compound
- 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.)
- Granted
Links
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229920000954 Polyglycolide Polymers 0.000 title claims description 18
- 229920000747 poly(lactic acid) Polymers 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 16
- 150000003606 tin compounds Chemical class 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 phosphoric acid (phosphorous acid) compound Chemical class 0.000 claims abstract description 10
- 229940005657 pyrophosphoric acid Drugs 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 33
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 17
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 9
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 24
- 239000004310 lactic acid Substances 0.000 abstract description 12
- 235000014655 lactic acid Nutrition 0.000 abstract description 12
- 238000013268 sustained release Methods 0.000 abstract description 7
- 239000012730 sustained-release form Substances 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000002689 soil Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003094 microcapsule Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000011159 matrix material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 16
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 239000001119 stannous chloride Substances 0.000 description 5
- 235000011150 stannous chloride Nutrition 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- YXTDAZMTQFUZHK-ZVGUSBNCSA-L (2r,3r)-2,3-dihydroxybutanedioate;tin(2+) Chemical compound [Sn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O YXTDAZMTQFUZHK-ZVGUSBNCSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 239000012567 medical material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 229940048084 pyrophosphate Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RCIVOBGSMSSVTR-UHFFFAOYSA-L stannous sulfate Chemical compound [SnH2+2].[O-]S([O-])(=O)=O RCIVOBGSMSSVTR-UHFFFAOYSA-L 0.000 description 2
- 229940007163 stannous tartrate Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910000375 tin(II) sulfate Inorganic materials 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- FEPMHVLSLDOMQC-UHFFFAOYSA-N virginiamycin-S1 Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O FEPMHVLSLDOMQC-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16465585A JPS6225121A (ja) | 1985-07-24 | 1985-07-24 | ポリグリコリドまたはポリラクチドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16465585A JPS6225121A (ja) | 1985-07-24 | 1985-07-24 | ポリグリコリドまたはポリラクチドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6225121A true JPS6225121A (ja) | 1987-02-03 |
| JPH0513963B2 JPH0513963B2 (https=) | 1993-02-23 |
Family
ID=15797299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16465585A Granted JPS6225121A (ja) | 1985-07-24 | 1985-07-24 | ポリグリコリドまたはポリラクチドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6225121A (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496923A (en) * | 1993-09-20 | 1996-03-05 | Mitsui Toatsu Chemicals, Inc. | Purification process of aliphatic polyester |
| EP0765913A1 (en) * | 1995-09-29 | 1997-04-02 | Dainippon Ink And Chemicals, Inc. | Process for the preparation of lactic acid-based polyester compositions |
| WO2007094352A1 (ja) | 2006-02-16 | 2007-08-23 | Toray Industries, Inc. | ポリエーテル-ポリ乳酸組成物およびそれを含んだポリ乳酸系フィルム |
| JP2007211197A (ja) * | 2006-02-13 | 2007-08-23 | Toray Ind Inc | ポリ乳酸可塑剤およびその製造方法 |
| JP2024523456A (ja) * | 2021-07-05 | 2024-06-28 | エルジー・ケム・リミテッド | ポリ乳酸重合体の製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4862899A (https=) * | 1971-11-22 | 1973-09-01 | ||
| JPS5161595A (ja) * | 1974-11-26 | 1976-05-28 | Adeka Argus Chemical Co Ltd | Horiesuterukeikasozaino seizohoho |
-
1985
- 1985-07-24 JP JP16465585A patent/JPS6225121A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4862899A (https=) * | 1971-11-22 | 1973-09-01 | ||
| JPS5161595A (ja) * | 1974-11-26 | 1976-05-28 | Adeka Argus Chemical Co Ltd | Horiesuterukeikasozaino seizohoho |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496923A (en) * | 1993-09-20 | 1996-03-05 | Mitsui Toatsu Chemicals, Inc. | Purification process of aliphatic polyester |
| US5679767A (en) * | 1993-09-20 | 1997-10-21 | Mitsui Toatsu Chemicals, Inc. | Purification process of aliphatic polyester |
| EP0765913A1 (en) * | 1995-09-29 | 1997-04-02 | Dainippon Ink And Chemicals, Inc. | Process for the preparation of lactic acid-based polyester compositions |
| JP2007211197A (ja) * | 2006-02-13 | 2007-08-23 | Toray Ind Inc | ポリ乳酸可塑剤およびその製造方法 |
| WO2007094352A1 (ja) | 2006-02-16 | 2007-08-23 | Toray Industries, Inc. | ポリエーテル-ポリ乳酸組成物およびそれを含んだポリ乳酸系フィルム |
| JP5239336B2 (ja) * | 2006-02-16 | 2013-07-17 | 東レ株式会社 | ポリエーテル−ポリ乳酸組成物およびそれを含んだポリ乳酸系フィルム |
| JP2024523456A (ja) * | 2021-07-05 | 2024-06-28 | エルジー・ケム・リミテッド | ポリ乳酸重合体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0513963B2 (https=) | 1993-02-23 |
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