GB930668A - Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams - Google Patents

Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams

Info

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
Application number
GB28348/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB930668A publication Critical patent/GB930668A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/18Heterocyclic 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
    • C07D207/22Heterocyclic 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • C07D207/2632-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/272-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
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers 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
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • C08F20/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415Five-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,
GB28348/59A 1958-08-28 1959-08-19 Acrylic esters of n-hydroxyalkyl and n-hydroxyalk-(oxyalkyl) lactams Expired GB930668A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (30)

* Cited by examiner, † Cited by third party
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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