JP5198263B2 - 高比粘度の無水マレイン酸及びアルキルビニルエーテルの共重合体を製造する方法 - Google Patents
高比粘度の無水マレイン酸及びアルキルビニルエーテルの共重合体を製造する方法 Download PDFInfo
- Publication number
- JP5198263B2 JP5198263B2 JP2008518240A JP2008518240A JP5198263B2 JP 5198263 B2 JP5198263 B2 JP 5198263B2 JP 2008518240 A JP2008518240 A JP 2008518240A JP 2008518240 A JP2008518240 A JP 2008518240A JP 5198263 B2 JP5198263 B2 JP 5198263B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl ether
- solvent
- alkyl vinyl
- acetylene
- maleic anhydride
- 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 - Fee Related
Links
- 229920001577 copolymer Polymers 0.000 title claims description 24
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 31
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 25
- -1 alkyl vinyl ether Chemical compound 0.000 claims description 24
- 239000003999 initiator Substances 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 11
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 10
- 229940011051 isopropyl acetate Drugs 0.000 claims description 10
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical group CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000011282 treatment Methods 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 6
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- 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
- 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/16—Monomers containing no hetero atoms other than the ether oxygen
- C08F216/18—Acyclic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/916—Interpolymer from at least three ethylenically unsaturated monoolefinic hydrocarbon monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
(発明の概要)
(発明の詳細な記載)
(対照(無アセチレン))
例1の処理を、1.684%の添加アセチレンを用いて繰返した。SVは16.08であった。
例1の処理を、1.17%の添加アセチレンを用いて繰返した。共重合体のSVは29.84であった。収率117g。
例1の処理を、1.48%の添加アセチレンを用いて繰返した。MA/MVE共重合体は33.012のSVを持った。
例1の処理を、1.784%の添加アセチレンを用いて繰返した。SVは50.867であった。
Claims (16)
- 無水マレイン酸及びアルキルビニルエーテルの高比粘度共重合体を製造する方法であり、無水マレイン酸及び前記アルキルビニルエーテルを、添加アセチレンの存在下に共重合する工程を備える、方法。
- 溶媒中で遂行される、請求項1記載の方法。
- アセチレンが前記溶媒において溶解する、請求項2記載の方法。
- アセチレンが前記アルキルビニルエーテルにおいて溶解する、請求項1記載の方法。
- 前記溶媒が、酢酸イソプロピル、シクロヘキサン、酢酸エチル、ベンゼン、そしてその混合物である、請求項2記載の方法。
- 40-90℃で遂行される、請求項1記載の方法。
- 前記アセチレンが少なくとも7の比粘度(SV)(1%重量/容量のメチルエチルケトン(MEK)25℃において)を持つ共重合体が生成されるのに十分な量において存在する、請求項1記載の方法。
- 溶媒としての酢酸イソプロピルに前記無水マレイン酸を添加する、請求項1記載の方法。
- 前記アルキルビニルエーテル(AVE)の1部分及び溶媒を予備付加する、請求項1記載の方法。
- 遊離基開始剤が合計単量体に基づく重量によって0.01-0.5%の量において存在する、請求項1記載の方法。
- 前記比粘度(SV)が少なくとも10である、請求項7記載の方法。
- 前記アルキルビニルエーテルがメチルビニルエーテルである、請求項1記載の方法。
- 溶媒及び遊離基開始剤の1部分を、アルキルビニルエーテルを含めて、予備付加する工程、
アルキルビニルエーテル及び無水マレイン酸を、前記溶媒において供給する工程、
アセチレンを、前記予備付加する工程により得られる予備付加物中に、又は前記予備付加する工程及び前記供給する工程により得られる反応混合物中に添加する工程、並びに
単量体を、前記反応混合物中に開始剤の部分を連続的に含めながら、アセチレンの存在下で共重合させ、予め定める分子量の前記単量体の共重合体を生成させる工程を備える、請求項1記載の方法。 - 溶媒が酢酸イソプロピルであり、遊離基開始剤が合計単量体に基づく重量によって0.01-0.5%の量において存在する、請求項13記載の方法。
- 12-60重量%の固形分を持つ、請求項1記載の方法の反応生成物。
- 請求項1の方法に従って製造される溶液。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/158,126 US7396886B2 (en) | 2005-06-21 | 2005-06-21 | Process for making copolymers of maleic anhydride and alkyl vinyl ether of high specific viscosity |
US11/158,126 | 2005-06-21 | ||
PCT/US2006/023132 WO2007001858A2 (en) | 2005-06-21 | 2006-06-14 | Process for making copolymers of maleic anhydride and alkyl vinyl ether of high specific viscosity |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009501805A JP2009501805A (ja) | 2009-01-22 |
JP2009501805A5 JP2009501805A5 (ja) | 2009-07-30 |
JP5198263B2 true JP5198263B2 (ja) | 2013-05-15 |
Family
ID=37574290
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008518240A Expired - Fee Related JP5198263B2 (ja) | 2005-06-21 | 2006-06-14 | 高比粘度の無水マレイン酸及びアルキルビニルエーテルの共重合体を製造する方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7396886B2 (ja) |
JP (1) | JP5198263B2 (ja) |
CN (1) | CN101495524B (ja) |
DE (1) | DE112006001609T5 (ja) |
WO (1) | WO2007001858A2 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8025709B2 (en) | 2009-01-09 | 2011-09-27 | Specialty Feritlizer Products, LLC | Quick drying polymeric coating |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3736996A1 (de) * | 1987-10-31 | 1989-05-11 | Basf Ag | Verfahren zur herstellung von copolymerisaten aus ethylenisch ungesaettigten dicarbonsaeureanhydriden und alkylvinylethern |
JP3323565B2 (ja) * | 1992-07-17 | 2002-09-09 | キヤノン株式会社 | インクジェット記録方法、インクセット、インクジェット記録ユニット、インクジェット記録用インクカートリッジ及びインクジェット記録装置 |
US5539039A (en) * | 1994-12-19 | 1996-07-23 | Isp Investments Inc. | Process for the preparation of stable water based stock solutions of crosslinked lower alkyl vinyl ether and maleic anhydride copolymers and hydrogel product of the process |
US5661221A (en) * | 1996-12-18 | 1997-08-26 | Colgate-Palmolive Company | Process for the preparation of cross-linked maleic anhydride copolymers |
US6184325B1 (en) * | 1999-03-16 | 2001-02-06 | Isp Investments Inc. | Solvent-free, fine white powders of high molecular weight copolymers of maleic anhydride and a C1-C4 alky vinyl ether without odor or taste |
US6624271B1 (en) * | 2002-11-26 | 2003-09-23 | Isp Investments Inc. | Process for making a solution of copolymers of maleic anhydride and alkyl vinyl ether in isopropyl acetate of high specific viscosity and at a high solids level |
ES2246695B1 (es) * | 2004-04-29 | 2007-05-01 | Instituto Cientifico Y Tecnologico De Navarra, S.A. | Composicion estimuladora de la respuesta inmunitaria que comprende nanoparticulas a base de un copolimero de metil vinil eter y anhidrido maleico. |
-
2005
- 2005-06-21 US US11/158,126 patent/US7396886B2/en active Active
-
2006
- 2006-06-14 CN CN200680022342.7A patent/CN101495524B/zh not_active Expired - Fee Related
- 2006-06-14 JP JP2008518240A patent/JP5198263B2/ja not_active Expired - Fee Related
- 2006-06-14 DE DE112006001609T patent/DE112006001609T5/de not_active Withdrawn
- 2006-06-14 WO PCT/US2006/023132 patent/WO2007001858A2/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
US7396886B2 (en) | 2008-07-08 |
WO2007001858A2 (en) | 2007-01-04 |
CN101495524A (zh) | 2009-07-29 |
CN101495524B (zh) | 2013-03-13 |
JP2009501805A (ja) | 2009-01-22 |
WO2007001858A3 (en) | 2009-04-23 |
US20060287452A1 (en) | 2006-12-21 |
DE112006001609T5 (de) | 2008-04-30 |
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