GB930668A - Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams - Google Patents
Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactamsInfo
- Publication number
- GB930668A GB930668A GB28348/59A GB2834859A GB930668A GB 930668 A GB930668 A GB 930668A GB 28348/59 A GB28348/59 A GB 28348/59A GB 2834859 A GB2834859 A GB 2834859A GB 930668 A GB930668 A GB 930668A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- prepared
- formula
- pyrrolidinone
- integer
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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)
- Pyrrole Compounds (AREA)
Abstract
The invention comprises polymers and copolymers of compounds of formula <FORM:0930668/IV(a)/1> where A is C2-10 alkylene with 2 to 4 carbon atoms in the lactam ring, x is an integer from 1 to 4, n is an integer from 1 to 4 when x is 1 and from 2 to 4 when x is greater than 1, R0 is hydrogen or C1-6 alkyl and R is acryloyl or methacryloyl, the CnH2nO groups present when x is greater than 1 being the same or different. In In examples polymers are prepared from N-(methacryloxyethoxyethyl) pyrrolidinone and N-(methacryloxyethoxyethoxyethyl) - pyrrolidinone by heating with azodiisobutyronitrile. The addition of 2-10% of such a polymer or copolymer to a monomer such as methyl methacrylate or a mixture of methyl methacrylate and ethyl acrylate in an organic solvent, either before or after polymerization of said monomer improves adhesion to metals and may be used in lacquers. The monomers of Formula I may be used in polyvinyl chloride plastisol compositions, e.g. a composition containing polyvinyl chloride, dioctyl phthalate, methacryloxyethyl pyrrolidinone and t-butyl perbenzoate is prepared by mixing on rollers, and then moulded, fluxed at 350 DEG F. and cooled.ALSO:The invention comprises compounds of formula <FORM:0930668/IV(a)/1> where A is an alkylene group of 2 to 10 carbon atoms with 2 to 4 carbon atoms in the heterocyclic ring, x is an integer from 1-4, n is an integer from 1-4 when x is one and from 2-4 when x is greater than 1, R DEG is hydrogen or C1-6 alkyl, and R is acryloyl or methacryloyl, the CnH2nO groups present when x is greater than one being the same or different. They are prepared from the corresponding hydroxy compounds of formula <FORM:0930668/IV(a)/2> by (1) alcoholysis with an acrylic or methocrylic ester containing up to 10 carbon atoms or (2) reaction with an acryloyl or methacryloyl halide in the presence of a hydrogen halide acceptor. Catalysts for method (1) include alkali metal and quaternary ammonium alkoxides including alkali metal derivatives of compounds of formula II, aromatic and aliphatic sulphonic acids and tetralkyl titanates, amounts of catalyst of 0.1-5% of the weight of compound II being mentioned; reflux temperatures, e.g. 65-140 DEG C., are mentioned; reduced pressure may be used. For method (2), temperatures of 0 to about 60 DEG C. are mentioned; an organic solvent may be present. Polymerization inhibitors may be included in the reaction mixtures or added subsequently. The starting materials of formula II in which both n and x are 1 may be prepared by reacting the corresponding lactams with formaldehyde using an alkaline catalyst; N-methylol-E-caprolactam and -piperidinone are thus prepared in Example 8. Other compounds in which x is 1 may be prepared by heating lactones with aminoalkanols; specific compounds thus prepared are: N-(3-hydroxypropyl)-, N - (3-hydroxybutyl), N - 2 - (1-hydroxy-2-methylpropyl)-, and N-2-(hydroxybutyl)-pyrrolidinone. Alternatively the corresponding pyrollinones, obtained by the hydrolysis by heating with water of pyrrolines, may be hydrogenated. Compounds with other sizes of lactam ring may be prepared by analagous methods. The compounds in which x is greater than one may be obtained by reacting N-hydroxyalkylactams with one or more alkylene oxides in one or more stages. Specified compounds thus prepared areN-hydroxy-ethoxyethyl, N-hydroxyethoxyethoxyethyl and N-hydroxyethoxyethoxyethoxy-, ethyl pyrrolidinones and a mixture of N-hydroxy-ethoxyethyl- and N- hydroxyethoxyethoxyethyl-3-methyl-3, 5-diisobutylpyrrolidinones. Many other compounds of formula II are mentioned,
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US75770458A | 1958-08-28 | 1958-08-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB930668A true GB930668A (en) | 1963-07-10 |
Family
ID=25048872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28348/59A Expired GB930668A (en) | 1958-08-28 | 1959-08-19 | Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE582131A (en) |
DE (1) | DE1160439B (en) |
FR (1) | FR1234004A (en) |
GB (1) | GB930668A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04217905A (en) * | 1990-09-14 | 1992-08-07 | Terumo Corp | Dentinal bonding promoting compound, pretreating agent and bonding composition containing the same |
US5523152A (en) * | 1993-10-27 | 1996-06-04 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents, and binder precursor compositions including same |
US5580647A (en) * | 1993-12-20 | 1996-12-03 | Minnesota Mining And Manufacturing Company | Abrasive articles incorporating addition polymerizable resins and reactive diluents |
US5667842A (en) * | 1993-10-27 | 1997-09-16 | Minnesota Mining And Manufacturing Company | Abrasive articles incorporating addition polymerizable resins and reactive diluents, and methods of making said abrasive articles |
WO2007051738A1 (en) * | 2005-11-03 | 2007-05-10 | Basf Se | Hydrogen-catalysed process for preparing (meth)acrylates of n-hydroxyalkylated lactams |
WO2008098885A1 (en) * | 2007-02-15 | 2008-08-21 | Basf Se | Method for producing (meth)acrylic esters of n-hydroxyalkylated lactams |
WO2008098887A1 (en) | 2007-02-15 | 2008-08-21 | Basf Se | Catalytic method for producing (meth)acrylic acid esters of n-hydroxyalkylated lactams |
WO2010069848A2 (en) * | 2008-12-19 | 2010-06-24 | Basf Se | Agrochemical formulations containing pyrrolidone alkylene oxides |
AU2012200844B2 (en) * | 2007-03-15 | 2014-02-06 | Dsm Ip Assets B.V. | Novel PDMS-PVP block copolymers |
WO2017087645A1 (en) | 2015-11-20 | 2017-05-26 | Isp Investments Llc | On-aqueous compositions of polymers derived from monomers having acryloyl moiety and lactam moiety and applications thereof |
WO2017087941A1 (en) | 2015-11-20 | 2017-05-26 | Isp Investments Llc | Proliferous polymers comprising lactamic moieties |
-
1959
- 1959-08-19 GB GB28348/59A patent/GB930668A/en not_active Expired
- 1959-08-24 DE DER26225A patent/DE1160439B/en active Pending
- 1959-08-28 BE BE582131A patent/BE582131A/en unknown
- 1959-08-28 FR FR803829A patent/FR1234004A/en not_active Expired
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2695064B2 (en) | 1990-09-14 | 1997-12-24 | テルモ株式会社 | Pretreatment agent for tooth adhesion |
JPH04217905A (en) * | 1990-09-14 | 1992-08-07 | Terumo Corp | Dentinal bonding promoting compound, pretreating agent and bonding composition containing the same |
US5710281A (en) * | 1993-10-27 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents and binder precursor compositions including same |
US5667842A (en) * | 1993-10-27 | 1997-09-16 | Minnesota Mining And Manufacturing Company | Abrasive articles incorporating addition polymerizable resins and reactive diluents, and methods of making said abrasive articles |
US5709935A (en) * | 1993-10-27 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents, and binder precursor compositions including same |
US5523152A (en) * | 1993-10-27 | 1996-06-04 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents, and binder precursor compositions including same |
US5733648A (en) * | 1993-10-27 | 1998-03-31 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents, and binder precursor compositions including same |
US5736747A (en) * | 1993-10-27 | 1998-04-07 | Minnesota Mining And Manufacturing Company | Organic compounds suitable as reactive diluents, and binder precursor compositions including same |
US5580647A (en) * | 1993-12-20 | 1996-12-03 | Minnesota Mining And Manufacturing Company | Abrasive articles incorporating addition polymerizable resins and reactive diluents |
WO2007051738A1 (en) * | 2005-11-03 | 2007-05-10 | Basf Se | Hydrogen-catalysed process for preparing (meth)acrylates of n-hydroxyalkylated lactams |
KR101346481B1 (en) * | 2005-11-03 | 2014-01-02 | 바스프 에스이 | Hydrogen-catalysed process for preparing (meth)acrylates of n-hydroxyalkylated lactams |
CN101300220B (en) * | 2005-11-03 | 2013-02-20 | 巴斯夫欧洲公司 | Hydrogen-catalysed process for preparing (meth)acrylates of n-hydroxyalkylated lactams |
JP2009515835A (en) * | 2005-11-03 | 2009-04-16 | ビーエーエスエフ ソシエタス・ヨーロピア | Process by heterogeneous catalysis for producing (meth) acrylates of N-hydroxyalkylated lactams |
US7750100B2 (en) | 2005-11-03 | 2010-07-06 | Basf Aktiengesellschaft | Catalytic process for preparing (meth)acrylates from N-hydroxyalkylated lactams |
JP2010518178A (en) * | 2007-02-15 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | Catalytic production of (meth) acrylic acid esters of N-hydroxyalkylated lactams |
WO2008098885A1 (en) * | 2007-02-15 | 2008-08-21 | Basf Se | Method for producing (meth)acrylic esters of n-hydroxyalkylated lactams |
JP2010518177A (en) * | 2007-02-15 | 2010-05-27 | ビーエーエスエフ ソシエタス・ヨーロピア | Catalytic process for preparing N-hydroxyalkylated lactam (meth) acrylic esters |
KR101440654B1 (en) * | 2007-02-15 | 2014-09-19 | 바스프 에스이 | Catalytic method for producing (meth)acrylic acid esters of n-hydroxyalkylated lactams |
KR101440653B1 (en) * | 2007-02-15 | 2014-09-19 | 바스프 에스이 | Method for producing (meth)acrylic esters of n-hydroxyalkylated lactams |
CN101622228B (en) * | 2007-02-15 | 2013-01-09 | 巴斯夫欧洲公司 | Method for producing (meth)acrylic esters of n-hydroxyalkylated lactams |
CN101631760B (en) * | 2007-02-15 | 2013-01-30 | 巴斯夫欧洲公司 | Catalytic method for producing (meth) acrylic acid esters of N-hydroxyalkylated lactams |
US8367788B2 (en) | 2007-02-15 | 2013-02-05 | Basf Se | Catalytic process for preparing (meth)acrylic esters of N-hydroxyalkylated lactams |
WO2008098887A1 (en) | 2007-02-15 | 2008-08-21 | Basf Se | Catalytic method for producing (meth)acrylic acid esters of n-hydroxyalkylated lactams |
US8476387B2 (en) | 2007-02-15 | 2013-07-02 | Basf Se | Catalytic process for preparing (meth)acrylic esters of N-hydroxyalkylated lactams |
AU2012200844B2 (en) * | 2007-03-15 | 2014-02-06 | Dsm Ip Assets B.V. | Novel PDMS-PVP block copolymers |
WO2010069848A2 (en) * | 2008-12-19 | 2010-06-24 | Basf Se | Agrochemical formulations containing pyrrolidone alkylene oxides |
US8268339B2 (en) | 2008-12-19 | 2012-09-18 | Basf Se | Agrochemical formulations containing pyrrolidone alkylene oxides |
WO2010069848A3 (en) * | 2008-12-19 | 2011-03-24 | Basf Se | Agrochemical formulations containing pyrrolidone alkylene oxides |
WO2017087645A1 (en) | 2015-11-20 | 2017-05-26 | Isp Investments Llc | On-aqueous compositions of polymers derived from monomers having acryloyl moiety and lactam moiety and applications thereof |
WO2017087941A1 (en) | 2015-11-20 | 2017-05-26 | Isp Investments Llc | Proliferous polymers comprising lactamic moieties |
Also Published As
Publication number | Publication date |
---|---|
BE582131A (en) | 1960-02-29 |
DE1160439B (en) | 1964-01-02 |
FR1234004A (en) | 1960-10-14 |
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