EP1098877A1 - Polymerderivate der alpha-olefin-maleinsäure-anhydrid-halbester oder der vollen säure - Google Patents
Polymerderivate der alpha-olefin-maleinsäure-anhydrid-halbester oder der vollen säureInfo
- Publication number
- EP1098877A1 EP1098877A1 EP99920192A EP99920192A EP1098877A1 EP 1098877 A1 EP1098877 A1 EP 1098877A1 EP 99920192 A EP99920192 A EP 99920192A EP 99920192 A EP99920192 A EP 99920192A EP 1098877 A1 EP1098877 A1 EP 1098877A1
- 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- Withdrawn
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)
- Pyrrole Compounds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US104309 | 1993-08-09 | ||
US103856 | 1998-06-24 | ||
US09/103,856 US6025501A (en) | 1997-04-25 | 1998-06-24 | Derivatized polymers of α-olefin-maleic anhydride alkyl half-ester or full acid |
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 |
US09/104,309 US5959122A (en) | 1997-04-25 | 1998-06-24 | Process for making derivatized polymers of maleic anhydride |
US103386 | 1998-06-24 | ||
PCT/US1999/009430 WO1999067216A1 (en) | 1998-06-24 | 1999-04-29 | DERIVATIZED POLYMERS OF α-OLEFIN-MALEIC ANHYDRIDE ALKYL HALF-ESTER OR FULL ACID |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1098877A1 true EP1098877A1 (de) | 2001-05-16 |
EP1098877A4 EP1098877A4 (de) | 2005-01-12 |
Family
ID=27379532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99920192A Withdrawn EP1098877A4 (de) | 1998-06-24 | 1999-04-29 | Polymerderivate der alpha-olefin-maleinsäure-anhydrid-halbester oder der vollen säure |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1098877A4 (de) |
JP (1) | JP2002518554A (de) |
AU (1) | AU3774999A (de) |
CA (1) | CA2334307A1 (de) |
WO (1) | WO1999067216A1 (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP2063854A1 (de) * | 2006-09-12 | 2009-06-03 | Intercos S.p.A. | Kosmetische zusammensetzung mit multifunktionalisiertem poly(alpha-olefin-copolymer-maleinsäureanhydrid) |
EP2407144A1 (de) * | 2010-07-13 | 2012-01-18 | The Procter & Gamble Company | Aerosolhaarsprayprodukt zum Stylen und/oder Formen von Haar |
EP2407145A1 (de) * | 2010-07-13 | 2012-01-18 | The Procter & Gamble Company | Aerosolhaarsprayprodukt zum Stylen und/oder Formen von Haar |
EP2570190A1 (de) | 2011-09-15 | 2013-03-20 | Braun GmbH | Sprühdüse zum Abgeben einer Flüssigkeit und Sprüheinrichtung, die eine solche Sprühdüse umfasst |
CN104780895A (zh) | 2013-06-28 | 2015-07-15 | 宝洁公司 | 包括喷洒装置的气溶胶发胶产品 |
WO2016196589A1 (en) | 2015-06-01 | 2016-12-08 | The Procter & Gamble Company | Aerosol hairspray product comprising a spraying device |
WO2019194949A1 (en) * | 2018-04-06 | 2019-10-10 | Dow Global Technologies Llc | Personal care cleaning composition |
WO2021021978A1 (en) | 2019-07-31 | 2021-02-04 | L'oreal | Compositions containing copolymer of vinylpyrrolidone and acrylic acid and film forming agent |
Citations (6)
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 (de) * | 1984-02-17 | 1985-09-11 | Bayer Ag | Copolymere auf Basis von Maleinsäureanhydrid und alpha, beta-ungesättigten Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Paraffininhibitoren |
DE3644656A1 (de) * | 1985-12-25 | 1987-07-02 | Ube Industries | Verfahren zur herstellung von n-(hydroxyphenyl)-maleimid-copolymeren |
EP0654486A2 (de) * | 1993-11-19 | 1995-05-24 | Tosoh Corporation | Verfahren zur Herstellung von Copolymeren |
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 |
-
1999
- 1999-04-29 CA CA002334307A patent/CA2334307A1/en not_active Abandoned
- 1999-04-29 AU AU37749/99A patent/AU3774999A/en not_active Abandoned
- 1999-04-29 JP JP2000555870A patent/JP2002518554A/ja active Pending
- 1999-04-29 WO PCT/US1999/009430 patent/WO1999067216A1/en active Application Filing
- 1999-04-29 EP EP99920192A patent/EP1098877A4/de not_active Withdrawn
Patent Citations (6)
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 (de) * | 1984-02-17 | 1985-09-11 | Bayer Ag | Copolymere auf Basis von Maleinsäureanhydrid und alpha, beta-ungesättigten Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Paraffininhibitoren |
DE3644656A1 (de) * | 1985-12-25 | 1987-07-02 | Ube Industries | Verfahren zur herstellung von n-(hydroxyphenyl)-maleimid-copolymeren |
EP0654486A2 (de) * | 1993-11-19 | 1995-05-24 | Tosoh Corporation | Verfahren zur Herstellung von Copolymeren |
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)
Title |
---|
See also references of WO9967216A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP1098877A4 (de) | 2005-01-12 |
CA2334307A1 (en) | 1999-12-29 |
WO1999067216A1 (en) | 1999-12-29 |
AU3774999A (en) | 2000-01-10 |
JP2002518554A (ja) | 2002-06-25 |
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