EP1098877A4 - Polymeres derivatises d'alkyl-semi-ester d'anhydride alpha-olefine-maleique ou de l'acide total - Google Patents

Polymeres derivatises d'alkyl-semi-ester d'anhydride alpha-olefine-maleique ou de l'acide total

Info

Publication number
EP1098877A4
EP1098877A4 EP99920192A EP99920192A EP1098877A4 EP 1098877 A4 EP1098877 A4 EP 1098877A4 EP 99920192 A EP99920192 A EP 99920192A EP 99920192 A EP99920192 A EP 99920192A EP 1098877 A4 EP1098877 A4 EP 1098877A4
Authority
EP
European Patent Office
Prior art keywords
polymer
mole
hours
maleic anhydride
ester
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.)
Withdrawn
Application number
EP99920192A
Other languages
German (de)
English (en)
Other versions
EP1098877A1 (fr
Inventor
Herbert W Ulmer
Timothy Gillece
John A Katirgis
Linda C Foltis
April Blaine
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.)
ISP Investments LLC
Original Assignee
ISP Investments LLC
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
Priority claimed from US09/103,386 external-priority patent/US5886194A/en
Priority claimed from US09/104,309 external-priority patent/US5959122A/en
Priority claimed from US09/103,856 external-priority patent/US6025501A/en
Application filed by ISP Investments LLC filed Critical ISP Investments LLC
Publication of EP1098877A1 publication Critical patent/EP1098877A1/fr
Publication of EP1098877A4 publication Critical patent/EP1098877A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—Compositions of homopolymers or 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, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines

Definitions

  • This invention relates to polymers of maleic anhydride, and, more particularly, to polymers of ⁇ -olefin-maleic anhydride alkyl half-ester or full acid, optionally with repeat units of maleamic acid and/or its maleimide, and to hair spray compositions which include these polymers as fixatives .
  • Hair spray compositions usually contain film-forming polymers as fixatives in a suitable delivery system.
  • Particularly desirable are polymers which can be formulated as one-phase hair spray compositions and which dry down to form continuous, clear and defectless ilms.
  • polymers of ⁇ -olefin- maleic anhydride alkyl half-ester or full acid optionally with repeat units of maleamic acid and/or its corresponding maleimide therein.
  • These polymers are particularly useful as fixatives in hair spray compositions, particularly as one-phase, 55-80% VOC ormulations in both pump and aerosol applications , in anhydrous or aqueous-alcoholic formulations, and in high hydrocarbon tolerant formulations. In use, these compositions dry down to form continuous , clear and defectless films.
  • the polymers of the invention contain repeat units of an ⁇ -olefin-maleic anhydride alkyl half-ester or full acid, optionally with repeat units of maleamic acid and/or maleimide.
  • Their general formula is given below:
  • a and A' are independently H or C 1 -C 4 alkyl ;
  • R is H or Cx-Ca alkyl and R' is an ⁇ -unsubstituted primary amine or hydroxy-containing ⁇ -unsubstituted primary amine having one or more of the following groups therein; hydrogen, silyl, amino, olefinic, carboxy and haloge ; and x is 0.01-1; y is 0-0.95; and z is 0-0.99.
  • the derivatized polymers of the invention are made by reacting an ⁇ -olefin-maleic anhydride copolymer or ⁇ - olefin-maleic anhydride alkyl half-ester copolymer, having the formula :
  • ROH aqueous, alcohol or aqueous-alcoholic solution
  • RNH 2 an ⁇ -unsubstituted primary amine
  • Ammonia or a silated primary amine, fluorinated primary amine , halogenated primary amine , unsaturated amine , cyanoamine , alcohol amines and amphoteric amines, also may be used.
  • the reaction is carried out at a reaction temperature of about 80-150°C, preferably about 100-130° C, for about 1-25 hours, preferably 2-10 hours.
  • a polymer having no amide repeat unit, i.e. all amide has been converted to the cyclic imide form can be obtained by carrying out the process at 115° C. for 5 hours or longer.
  • the resultant polymer thus includes only half-ester and cyclic imide repeat units therein. Higher reaction temperatures and longer reaction times enhance the conversion of amide into the corresponding cyclic imide repeating unit by loss of a water molecule .
  • the ⁇ -olefin-maleic anhydride or ⁇ -olefin-maleic anhydride alkyl half-ester copolymers used as starting materials in the process of the invention are made by a suspension polymerization method in a hydrocarbon solvent.
  • the suspending agent and a free radical polymerization initiator are charged to a reactor and purged with nitrogen gas .
  • the reactor is heated to 60°C and a predetermined amount of molten maleic anhydride is introduced into the reactor vessel.
  • the reactor is heated to 80°C and isobutylene is fed in continuously over a predetermined amount of time.
  • the resultant feed rate is based on the efficiency of removal of heat from the system which is evolved during the polymerization reaction.
  • a white suspension of the polymer in the solvent is obtained which can be dried to provide a free- flowing, white powder of the desired copolymer.
  • the suspension can be pumped into a reactor and sparged with heated ethanol or water to remove the lower boiling hydrocarbon solvent and effect conversion of the anhydride polymer to its corresponding ethyl half-ester or diacid derivative.
  • suspension polymerization is carried out under these conditions :
  • the reactant solids are maintained at about 20 to 50%, preferably about 30%;
  • the suspending agent is a hydrocarbon soluble resin, preferably containing maleic anhydride, e.g. p (octadecylvinylether-co-maleic anhydride) or p (octadecylene-co-maleic anhydride) ;
  • the suspending agent is present in an amount of about 0.25 to 3 wt. % solids;
  • the initiator is an azo or peroxide initiator, with a half-life of at least 10 hours at a reaction temperature between about 60° and 90° C, preferably, a peroxide initiator;
  • reaction temperature is at least 80° C.
  • the hydrocarbon solvent is pentane or hexane.
  • the starting polymers of FORMULA I may be made by precipitation polymerization in a solvent such as isopropyl acetate.
  • the resultant film is a continuous , clear, defectless film.
  • EXAMPLE 2 Into a high pressure reactor was added: 75.4 g (0.490 mole) P (isobutylene-MAn) powder, 19.8 g octadecylamine (0.0735 mole) and 222.1 g ethanol . The reaction mixture was then purged with N 2 gas and the temperature was raised to 50°C and held there for 1 hour. Then the temperature was increased to 75°C, held for 2 hours, and thereafter to 100°C for 3 hours. Upon cooling the resultant product had a slightly green color and a slight haze. The dried polymer had an acid of 225 mg KOH/g polymer and contained about 2 wt. % free amine.
  • the resultant reaction slurry was stirred, sealed and purged with N 2 gas .
  • the temperature was raised to and kept at 75°C for 2 hours and then raised to and kept at 100°C for 5 hours.
  • the reaction product was a clear slightly yellow solution.
  • the resultant polymer had an Acid No. of 202 mg KOH/g polymer and 0.142 meq. free amine/g of product.
  • EXAMPLE 7 To a 2-liter, high pressure reactor was added: 64.7 g (0.420 mole) p (isobutylene-maleic anhydride), 8.14 g (0.0630 mole) 2-ethylhaxylamine and 16.97 g (0.0630 mole) octadecylamine and 200 g ethanol. The reactor was purged with N 2 gas . The reactor was heated to 75°C and held for 2 hours and then heated to 100°C and held for 5 hours . The resultant material possessed an acid number of 205 mg KOH/g polymer.
  • EXAMPLE 8 To a 2-liter, high pressure reactor was added: 73.4 g (0.477 mole) p (isobutylene-maleic anhydride), 10.45 g (0.143 mole) n-butylamine and 12.83 g (0.0476 mole) octadecylamine and 171 g ethanol. The reactor was purged with N 2 gas. The reactor was heated to 75°C and held for 2 hours and then heated to 100 °C and held for 5 hours . The resultant material possessed an acid number of 195 mg KOH/g polymer.
  • EXAMPLE 9 To a 2-liter, high pressure reactor was added: 66.0 g p (isobutylene-maleic anhydride and 198 g ethanol. The reactor was purged with N 2 gas . The reactor was heated to 130°C and held for 8 hours. The resultant material possessed an acid number of 265 mg KOH/g polymer .
  • EXAMPLE 10 To a 2-liter, high pressure reactor was added: 66.0 g (0.429 mole) p (isobutylene-maleic anhydride, 5.80 g (0.129 mole) ethylamine, 9.40 g (0.129 mole) n-butylamine and 198 g ethanol. The reactor was purged with N 2 gas. The reactor was heated to 100°C and held for 3 hours and then the reactor was heated to 130°C and held for 5 hours. The resultant material possessed an acid number of 120 mg KOH/g polymer.
  • EXAMPLE 11 Into a high pressure reactor was added: 22.8 g (0.148 mole) p(IB-MAn), 3.33 g ethylamine (0.0517 mole) (70%), 2.96 g water and 45.62 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 100°C over 1 hour. Upon reaching 100°C, 5.44 g (0.0891 mole) ethanolamine dissolved in 19.85 g water was added to the reaction mixture . The reaction was held at 100°C for 1 hour and then raised to 130°C over 1 hour and held for an additional 8 hours . Cooling provided a clear yellow solution. The dried polymer had an acid number of only about 25 mg KOH/g polymer, indicating substantially all maleimide repeat units in the polymer.
  • EXAMPLE 12 Into a high pressure reactor was added: 154.0 g (1.00 mole) p(IB-MAn), 9.02 g ((0.140 mole) ethylamine (70%), 10.97 g (0.150 mole) butylamine and 316 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130°C over 2 hours and held for 3 hours . The reaction mixture was cooled to which was added 36.65 g (0.600 mole) of ethanolamine dissolved in 176 g of water. The reactor was gradually reheated to 130°C over 3 hours and held for 8 hours. A clear yellow solution provided a polymer having an acid number of about 65 mg KOH/g polymer.
  • EXAMPLE 13 Into a high pressure reactor was added: 60.0 g (0.390 mole) p(IB-MAn) powder (acid # 280 in ethanol), 14.5 g (0.198 mole) n-butylamine and 175 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130°C over 3 hours and held for 5 hours to provide the p(IB-MAn) half acid/ester. The reaction mixture then was cooled to 30°C and 11.9 g (0.195 mole) of ethanolamine dissolved in 25 g water was added slowly to the reaction mixture. The reactor was gradually reheated to 130°C over 3 hours and held for 5 hours. Upon cooling, a clear yellow solution was obtained. The dried polymer had an acid number of only about 35 mg KOH/g polymer. The reduced acid number indicating the predominance of the maleimide repeat unit therein over the maleamic acid unit.
  • EXAMPLE 14 Into a high pressure reactor was added: 154.0 g (1.00 mole) p(IB-MAn) and 326 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130 °C over 2 hours and held or 3 hours . The reaction mixture was cooled to which was added 28.5 g (0.379 mole) 3-amino-l-propanol and 34.82 g (0.570 mole) of ethanolamine dissolved in 181 g water. The reactor was gradually reheated to 130 °C over 3 hours and held for 8 hours. Upon cooling, a clear yellow solution was obtained.
  • the dried polymer had an acid number of about 125 mg KOH/g polymer, indicating the presence of both maleamic acid and maleimide repeat units in the polymer.
  • EXAMPLE 15 Into a high pressure reactor was added: 154.0 g (1.00 mole) p(IB-MAn) and 320 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130°C over 2 hours and held for 3 hours . The reaction mixture was cooled to which was added 7.51 g (0.100 mole) 3-amino-l-propanol and 51.92 g (0.850 mole) of ethanolamine dissolved in 178 g of water. The reactor was gradually reheated to 130°C over 3 hours and held for 8 hours . The resultant product was a clear yellow solution. The dried polymer had an acid number of about 75 mg KOH/g polymer.
  • EXAMPLE 16 Into a high pressure reactor was added: 123 g (0.615 mole) onoethyl half ester of p(IB-MAn), 35.6 g (0.583 mole) ethanolamine, 88 g water and 199 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130°C over 2 hours and held for 8 hours. The resultant product was a clear yellow solution. The dried polymer had an acid number of about 70 mg KOH/g polymer.
  • EXAMPLE 17 Into a high pressure reactor was added: 22.8 g (0.148 mole) p(IB-MAn), 3.33 g ethylamine (0.0517 mole) (70%), 2.96 g water and 45.62 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 100°C over 1 hour. Upon reaching 100°C, 5.44 g (0.0891 mole) ethanolamine dissolved in 19.85 g water was added to the reaction mixture. The reaction was held at 100°C for 1 hour and then raised to 130°C over 1 hour and held for an additional 8 hours . Cooling provided a clear yellow solution. The dried polymer had an acid number of only about 25 mg KOH/g polymer, indicating substantially all maleimide repeat units in the polymer .
  • EXAMPLE 18 Into a high pressure reactor was added: 154.0 g (1.00 mole) p(IB-MAn), 9.02 g (0.140 mole) ethylamine (70%), 10.97 g (0.150 mole) butylamine and 316 g ethanol. The reaction was purged with N 2 gas and the temperature raised to 130°C over 2 hours and held for 3 hours. The reaction mixture was cooled to which was added 36.65 g (0.600 mole) of ethanolamine dissolved in 176 g of water. The reactor was gradually reheated to 130 °C over 3 hours and held for 8 hours . A clear yellow solution provided a polymer having an acid number of about 65 mg KOH/g polymer .
  • EXAMPLE 19 Into a high pressure reactor was added: 100 g (0.500 mole) monoethyl half ester of p(IB-MAn), 24.40 g (0.399 mole) ethanolamine, 3.66 g (0.0500 mole) butylamine, 4.63 g (0.0250 mole) dodecylamine, 84 g water and 150 g ethanol . The reaction was purged with N 2 gas and the temperature raised to 130°C over 2 hours and held for 8 hours . Upon cooling the resultant product was a clear yellow solution. The dried polymer had an acid number of about 65 mg KOH/g polymer.
  • EXAMPLE 20 Into a high pressure reactor was added: 60.0 g (0.390 mole) p(IB-MAn) powder, 6.26 g (0.0972 mole) ethylamine (70%), 7.13 g (0.0975 mole) butylamine and 175 g ethanol . The reaction was purged with N 2 gas and the temperature raised to 130°C over 3 hours and held for 5 hours. The reaction mixture was cooled to 30 °C and 11.91 g (0.195 mole) of ethanolamine dissolved in 20 g water and 30 g ethanol was added slowly to the reaction mixture. The reactor was gradually reheated to 130°C over 3 hours and held for 5 hours . Upon cooling the resultant product was a clear yellow solution . The dried polymer had an acid number of about 45 mg KOH/g polymer.
  • EXAMPLE 21 60 g (0.390 mole) of a p (isobutylene-co-maleic anhydride) prepolymer and 150 g of water was charged into a 1-liter pressure reactor and purged with nitrogen. The reactor was gradually heated to 100°C and held for 1-hour. Then the reactor was heated to 130°C over a 1-hour period while 22.13 g (0.362 mole) ethanolamine was gradually added to the reaction mixture . Upon reaching 130° C, the reaction mixture was held for 8 hours and cooled. The product was a slight hazy, orange solution.
  • the polymers of the invention is formulated into a hydroalcoholic pump hair spray system containing as little as 3.5% water and a maximum of 91% water
  • Imidized IB/MA Copolymer 12.50 (40% solids, 27% H 2 0, 33% EtOH)
  • EXAMPLE 22B The polymers of the invention is formulated into a single phase hydroalcoholic aerosol hair spray system having a VOC content of 35% to 95%, with dimethyl ether as the propellant.
  • Formula III
  • Imidized IB/MA Copolymer 12.50 (40% solids, 27% H 2 0, 33% EtOH)
  • Imidized IB/MA Copolymer 12.50 (40% solids, 27% H 2 0, 33% EtOH)
  • Imidized IB/MA Copolymer 12.50 (40% solids, 27% H 2 0, 33% EtOH)

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne des polymères dérivatisés d'alkyl-semi-ester d'anhydride alpha-oléfine-maléique ou de l'acide total, de préférence du composé isobutylène, renfermant éventuellement des unités répétées d'acide maléamique et/ou du maléimide correspondant. Ces polymères sont utiles comme fixateurs dans les produits d'hygiène personnelle, tels que les compositions de laque capillaire, notamment comme phase unique; les formulations à faible teneur en contaminants organiques volatils, telles que celles utilisées dans les systèmes d'aérosols; et les formulations de solvants anhydres, alcooliques, aqueuses-alcooliques et très tolérantes aux hydrocarbures. En utilisation, ces compositions de laque capillaire sèchent en formant des films transparents, continus et sans défaut.
EP99920192A 1998-06-24 1999-04-29 Polymeres derivatises d'alkyl-semi-ester d'anhydride alpha-olefine-maleique ou de l'acide total Withdrawn EP1098877A4 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US104309 1998-06-24
US09/103,386 US5886194A (en) 1998-03-04 1998-06-24 Hydroxyamino-derivatized polymers of olefin-maleic anhydride in the form of their maleimide maleamic acid and α- olefin-maleic anhydride half-acid/half ester or full acid repeat units process for making same
US103856 1998-06-24
US103386 1998-06-24
US09/104,309 US5959122A (en) 1997-04-25 1998-06-24 Process for making derivatized polymers of maleic anhydride
US09/103,856 US6025501A (en) 1997-04-25 1998-06-24 Derivatized polymers of α-olefin-maleic anhydride alkyl half-ester or full acid
PCT/US1999/009430 WO1999067216A1 (fr) 1998-06-24 1999-04-29 Polymeres derivatises d'alkyl-semi-ester d'anhydride alpha-olefine-maleique ou de l'acide total

Publications (2)

Publication Number Publication Date
EP1098877A1 EP1098877A1 (fr) 2001-05-16
EP1098877A4 true EP1098877A4 (fr) 2005-01-12

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EP99920192A Withdrawn EP1098877A4 (fr) 1998-06-24 1999-04-29 Polymeres derivatises d'alkyl-semi-ester d'anhydride alpha-olefine-maleique ou de l'acide total

Country Status (5)

Country Link
EP (1) EP1098877A4 (fr)
JP (1) JP2002518554A (fr)
AU (1) AU3774999A (fr)
CA (1) CA2334307A1 (fr)
WO (1) WO1999067216A1 (fr)

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DE10055935A1 (de) 2000-11-10 2002-05-29 Wella Ag Volumengebendes und gezielt den Haaransatz festigendes Haarbehandungsprudukt
US6824650B2 (en) 2001-12-18 2004-11-30 Kimberly-Clark Worldwide, Inc. Fibrous materials treated with a polyvinylamine polymer
MXPA05001961A (es) * 2002-08-30 2005-04-28 Isp Investments Inc Polimeros de sensacion natural.
US7994079B2 (en) 2002-12-17 2011-08-09 Kimberly-Clark Worldwide, Inc. Meltblown scrubbing product
US20060159642A1 (en) * 2004-12-22 2006-07-20 Avon Products, Inc. Mascara composition and method of using
DE102005056160A1 (de) * 2005-11-23 2007-05-24 Henkel Kgaa Haarfestigungsmittel mit derivatisiertem Maleinsäureanhydrid-Polymer und amphoterem filmbildendem Polymer
ITMI20060326A1 (it) * 2006-02-23 2007-08-24 Intercos Italiana Composizione cosmetica comprendente polimeri funzionalizzati
CN101541295B (zh) * 2006-09-12 2011-09-14 因特科有限公司 包含多官能化的α-烯烃/马来酸酐共聚物的化妆品组合物
EP2407145A1 (fr) * 2010-07-13 2012-01-18 The Procter & Gamble Company Produit de laque aérosol pour la mise en forme des cheveux
EP2407144A1 (fr) * 2010-07-13 2012-01-18 The Procter & Gamble Company Produit de laque aérosol pour styliser et/ou mettre en place les cheveux
EP2570190A1 (fr) 2011-09-15 2013-03-20 Braun GmbH Buse de pulvérisation pour distribuer un fluide et pulvérisateur comportant une telle buse de pulvérisation
US9986809B2 (en) 2013-06-28 2018-06-05 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
MX368467B (es) 2015-06-01 2019-10-03 Procter & Gamble Producto de laca en aerosol para el cabello que comprende un dispositivo de rociado.
WO2019194949A1 (fr) * 2018-04-06 2019-10-10 Dow Global Technologies Llc Composition de nettoyage pour soins personnels
WO2021021978A1 (fr) 2019-07-31 2021-02-04 L'oreal Compositions contenant un copolymère de vinylpyrrolidone et d'acide acrylique et agent de formation de film

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2416117A1 (de) * 1974-04-03 1975-10-30 Texaco Development Corp Verfahren zur herstellung von imid- und estergruppenhaltigen aethylen-maleinsaeureanhydrid-copolymerisaten und ihre verwendung
DE3319014A1 (de) * 1983-05-26 1984-11-29 Bayer Ag, 5090 Leverkusen Copolymere und ihre verwendung als leimungsmittel
EP0154177A2 (fr) * 1984-02-17 1985-09-11 Bayer Ag Copolymères à base d'anhydride maléique et de composés alpha,bêta insaturés, leur procédé de fabrication et leur application comme inhibiteurs de paraffines
DE3644656A1 (de) * 1985-12-25 1987-07-02 Ube Industries Verfahren zur herstellung von n-(hydroxyphenyl)-maleimid-copolymeren
EP0654486A2 (fr) * 1993-11-19 1995-05-24 Tosoh Corporation Procédé de fabrication de copolymères
US5886194A (en) * 1998-03-04 1999-03-23 Isp Investments Inc. Hydroxyamino-derivatized polymers of olefin-maleic anhydride in the form of their maleimide maleamic acid and α- olefin-maleic anhydride half-acid/half ester or full acid repeat units process for making same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2416117A1 (de) * 1974-04-03 1975-10-30 Texaco Development Corp Verfahren zur herstellung von imid- und estergruppenhaltigen aethylen-maleinsaeureanhydrid-copolymerisaten und ihre verwendung
DE3319014A1 (de) * 1983-05-26 1984-11-29 Bayer Ag, 5090 Leverkusen Copolymere und ihre verwendung als leimungsmittel
EP0154177A2 (fr) * 1984-02-17 1985-09-11 Bayer Ag Copolymères à base d'anhydride maléique et de composés alpha,bêta insaturés, leur procédé de fabrication et leur application comme inhibiteurs de paraffines
DE3644656A1 (de) * 1985-12-25 1987-07-02 Ube Industries Verfahren zur herstellung von n-(hydroxyphenyl)-maleimid-copolymeren
EP0654486A2 (fr) * 1993-11-19 1995-05-24 Tosoh Corporation Procédé de fabrication de copolymères
US5886194A (en) * 1998-03-04 1999-03-23 Isp Investments Inc. Hydroxyamino-derivatized polymers of olefin-maleic anhydride in the form of their maleimide maleamic acid and α- olefin-maleic anhydride half-acid/half ester or full acid repeat units process for making same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9967216A1 *

Also Published As

Publication number Publication date
WO1999067216A1 (fr) 1999-12-29
AU3774999A (en) 2000-01-10
EP1098877A1 (fr) 2001-05-16
CA2334307A1 (fr) 1999-12-29
JP2002518554A (ja) 2002-06-25

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