JPH0615522B2 - メルカプトアルキルアセトアセテート - Google Patents
メルカプトアルキルアセトアセテートInfo
- Publication number
- JPH0615522B2 JPH0615522B2 JP1278772A JP27877289A JPH0615522B2 JP H0615522 B2 JPH0615522 B2 JP H0615522B2 JP 1278772 A JP1278772 A JP 1278772A JP 27877289 A JP27877289 A JP 27877289A JP H0615522 B2 JPH0615522 B2 JP H0615522B2
- Authority
- JP
- Japan
- Prior art keywords
- mercaptoalkyl
- acetoacetate
- tkd
- reaction
- diketene
- 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 - Lifetime
Links
- -1 Mercaptoalkyl acetoacetate Chemical compound 0.000 title abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- QXUCUVZHYIRQTP-UHFFFAOYSA-N 2-sulfanylethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCS QXUCUVZHYIRQTP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical group CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 1
- MJQWABQELVFQJL-UHFFFAOYSA-N 3-Mercapto-2-butanol Chemical compound CC(O)C(C)S MJQWABQELVFQJL-UHFFFAOYSA-N 0.000 description 1
- SBNPUFFNNRYIBL-UHFFFAOYSA-N 4-(4-hydroxyphenyl)-3-oxobutanethioic S-acid Chemical compound OC1=CC=C(CC(=O)CC(S)=O)C=C1 SBNPUFFNNRYIBL-UHFFFAOYSA-N 0.000 description 1
- LLPNBWNKPILNSX-UHFFFAOYSA-N 4-methylideneoxetan-2-one propan-2-one Chemical compound CC(C)=O.C=C1CC(=O)O1 LLPNBWNKPILNSX-UHFFFAOYSA-N 0.000 description 1
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical group 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZEYMDLYHRCTNEE-UHFFFAOYSA-N ethenyl 3-oxobutanoate Chemical group CC(=O)CC(=O)OC=C ZEYMDLYHRCTNEE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/265,185 US4960924A (en) | 1988-10-31 | 1988-10-31 | Mercaptoalkyl acetoacetates |
| US265185 | 1999-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02172965A JPH02172965A (ja) | 1990-07-04 |
| JPH0615522B2 true JPH0615522B2 (ja) | 1994-03-02 |
Family
ID=23009376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1278772A Expired - Lifetime JPH0615522B2 (ja) | 1988-10-31 | 1989-10-27 | メルカプトアルキルアセトアセテート |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4960924A (en, 2012) |
| EP (1) | EP0367508B1 (en, 2012) |
| JP (1) | JPH0615522B2 (en, 2012) |
| AT (1) | ATE78464T1 (en, 2012) |
| AU (1) | AU616810B2 (en, 2012) |
| BR (1) | BR8905471A (en, 2012) |
| DE (1) | DE68902219T2 (en, 2012) |
| ES (1) | ES2052022T3 (en, 2012) |
| GR (1) | GR3005257T3 (en, 2012) |
| MX (1) | MX165352B (en, 2012) |
| NZ (1) | NZ231105A (en, 2012) |
| SG (1) | SG117392G (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4935482A (en) * | 1989-01-03 | 1990-06-19 | Dow Corning Corporation | Polysiloxane-polyurea block copolymers |
| US5767199A (en) * | 1992-07-29 | 1998-06-16 | Rohm And Hass Company | Shelf stable compositions containing acetoacetate functional polymer and polyformal |
| US5516453A (en) * | 1993-02-19 | 1996-05-14 | Rohm And Haas Company | Stable ambient-curing composition |
| US5525662A (en) * | 1993-07-14 | 1996-06-11 | Rohm And Haas Company | Functionalization of polymers via enamine of acetoacetate |
| US5426142A (en) * | 1993-08-25 | 1995-06-20 | Rohm And Haas Company | Single package ambient curing polymers |
| US5428107A (en) * | 1993-10-29 | 1995-06-27 | Rohm And Haas Company | Silane-modified floor finish vehicles |
| US5414041A (en) * | 1994-04-08 | 1995-05-09 | Rohm And Haas Company | Waterborne coating composition |
| AU720104B2 (en) | 1995-12-04 | 2000-05-25 | Rohm And Haas Company | Waterborne crosslinkable coating compositions |
| JP4525250B2 (ja) * | 2004-08-27 | 2010-08-18 | Ｊｓｒ株式会社 | 感放射線性樹脂組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2351366A (en) * | 1939-07-03 | 1944-06-13 | Pohl Franz Josef | Process of preparing acetoacetic esters |
| DE1568494A1 (de) * | 1966-02-26 | 1970-03-05 | Hoechst Ag | Verfahren zur Herstellung von Mono- und Polycetessigsaeureestern |
| US3424855A (en) * | 1966-09-27 | 1969-01-28 | Us Navy | Electrical conductor attachment means |
| US3689568A (en) * | 1969-08-13 | 1972-09-05 | Richard J Eletto | Preparation of primary mercaptans |
| GB1392851A (en) * | 1972-04-06 | 1975-04-30 | Beheer Bv Pfw | Mercapto alcohols and esters |
| US4396552A (en) * | 1980-02-08 | 1983-08-02 | Ciba-Geigy Corporation | Novel metal mercaptides of esters of β-mercaptoalkanols |
-
1988
- 1988-10-31 US US07/265,185 patent/US4960924A/en not_active Expired - Fee Related
-
1989
- 1989-10-24 NZ NZ231105A patent/NZ231105A/xx unknown
- 1989-10-26 MX MX018114A patent/MX165352B/es unknown
- 1989-10-26 BR BR898905471A patent/BR8905471A/pt not_active Application Discontinuation
- 1989-10-27 EP EP89311095A patent/EP0367508B1/en not_active Expired - Lifetime
- 1989-10-27 ES ES89311095T patent/ES2052022T3/es not_active Expired - Lifetime
- 1989-10-27 AT AT89311095T patent/ATE78464T1/de not_active IP Right Cessation
- 1989-10-27 DE DE8989311095T patent/DE68902219T2/de not_active Expired - Fee Related
- 1989-10-27 JP JP1278772A patent/JPH0615522B2/ja not_active Expired - Lifetime
- 1989-10-30 AU AU43858/89A patent/AU616810B2/en not_active Ceased
-
1992
- 1992-07-23 GR GR920401549T patent/GR3005257T3/el unknown
- 1992-11-06 SG SG1173/92A patent/SG117392G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE78464T1 (de) | 1992-08-15 |
| GR3005257T3 (en, 2012) | 1993-05-24 |
| DE68902219D1 (de) | 1992-08-27 |
| BR8905471A (pt) | 1990-05-29 |
| MX165352B (es) | 1992-11-04 |
| US4960924A (en) | 1990-10-02 |
| AU4385889A (en) | 1990-05-03 |
| NZ231105A (en) | 1991-10-25 |
| EP0367508A1 (en) | 1990-05-09 |
| AU616810B2 (en) | 1991-11-07 |
| ES2052022T3 (es) | 1994-07-01 |
| DE68902219T2 (de) | 1993-03-11 |
| JPH02172965A (ja) | 1990-07-04 |
| SG117392G (en) | 1993-02-19 |
| EP0367508B1 (en) | 1992-07-22 |
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