US3234098A - Phthalic acid hair spray - Google Patents
Phthalic acid hair spray Download PDFInfo
- Publication number
- US3234098A US3234098A US284349A US28434963A US3234098A US 3234098 A US3234098 A US 3234098A US 284349 A US284349 A US 284349A US 28434963 A US28434963 A US 28434963A US 3234098 A US3234098 A US 3234098A
- Authority
- US
- United States
- Prior art keywords
- hair
- acid
- alcohol
- synthetic resin
- hair spray
- 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 - Lifetime
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 title claims description 13
- 239000008266 hair spray Substances 0.000 title description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 229920003002 synthetic resin Polymers 0.000 claims description 19
- 239000000057 synthetic resin Substances 0.000 claims description 19
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 239000003380 propellant Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 description 26
- 210000004209 hair Anatomy 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- -1 alkane diol Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 229940039717 lanolin Drugs 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920006186 water-soluble synthetic resin Polymers 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010019049 Hair texture abnormal Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004341 Octafluorocyclobutane Substances 0.000 description 1
- 241000791876 Selene Species 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
-
- 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- 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
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/01—Aerosol hair preparation
Definitions
- This invention is concerned with improvements in or relating to hair sprays.
- water-soluble synthetic resins e.g. half esters of copolymers of maleic anhydride, condensation products of formaldehyde with hydantoin substituted in the -position, N-vinyl-Z-oxazolidone polymcrs, polymers of N-vinylpyrrolidone or its copolymers with vinyl acetate, polyvinylimidazole and panthenol in aerosol hair sprays.
- polyester resins do not have these disadvantages and may be used to yield hair sprays which absorb grease excellently. Since they also forman even surface on the single hairs, even with very greasy hair, they impart a very good gloss to the treated hair. Due to their good fat solubility and fat compatibility it is also possible to use fatty substances in the hair sprays and thus produce very suitable hair sprays for dry hair. Moreover, the resins are odorless, clear and physiologically inert.
- composition suitable for use as a hair spray comprising a synthetic resin of a melting point about 40 C. functioning as a hair setting compound, said synthetic resin being an esterification product of a phthalic acid (or an anhydride where such exists) and a dihydric alcohol, and a propellant and/or a perfume.
- the said dihydric alcohol is an alkane diol of 2 to 6 carbon atoms, an ether of a polyhydrie alcohol having 3 to 6 hydroxy groups, in which the hydroxy groups in excess of two are ctherified by alkyl groups of l to 3 carbon atoms, 4,4-clihydroxydicyclohexylpropane or a mixture of any one of the aforementioned alcohol components with less than an equivalent amount with respect to the latter of a polyhydric alcohol containing at least 3 and at most 6 hydroxy groups.
- the propellant is preferably a fiuorohydrocarbon or a chlorofiuorohydrocarbon in which even all of the hydrogen atoms may be substituted by halogen atoms, particularly the variou chlorofiuoromethanes.
- propellant there is also suitable octafluorocyclobutane, if desired in admixture with isobutane, the proportion of which in the mixture may be between and 33%.
- the synthetic resin may be produced by reaction of the above-mentioned acids with the above-mentioned dihydric alcohols, for example in an equivalent ratio from 1:09 to 1:1.4, preferably from 1:1 to 1:1.25.
- esterification is preferably carried out until the resin has an acid value from so to 150, mtvtu'itageously from 90 to 120.
- Such resins should be hard and non-tacky; thus they should have a melting point above 40 C., preferably above C.
- they are distinguished by a good solubility in halogen-containing, especially chlorine-containing hydrocarbons, such as methylene chloride, and generally also in lower and higherhlcohols.
- the dihydric alcohol component of the resin preferably contains at least three carbon atoms bound to each other by carbon to carbon bonds.
- the alcohol component may be, for example, ethylene glycol, propanodiol-l,2 or -l,3, butanediol-l,3 or butancdiol-1,4, hexanediol-2,5, hcxcnediol-1,6 or a mixture of such alcohols, but preferably it is 2,2-dimethyl propanediol-1,3 or 4,4-dihydroxy-dicyclohexylpropane. Homologues of this last-mentioned substance may also be used.
- aleohol component there may also be used ethers of polyhydric alcohols in which the hydroxy groups in excess of 2 are etherified by shortchaincd aliphatic radicals such as methyl, ethyl, propyl or isopropyl but which others still contain 2 free hydroxy groups.
- the synthetic resins may be modified inasmuch as the alcohol component used is a mixture of a dihydric alcohol with less than an equivalent portion with respect to the latter of a polyhydric alcohol containing at least 3 hydroxyl groups e.g. glycerol, trimethylolethane, trimethylolpropane, pentaerythritol, sorbitol or mannitol.
- the polyhydric alcohol may be used in such modified polyester resins, for example in an amount up to 80 equivalent percent, preferably between and equivalent percent, calculated on the dihydric alcohol.
- the hair sprays according to the invention may also contain additives such as solvents and diluents.
- Example 1 A fat-free hair spray can be obtained by mixing the following raw materials to form a base:
- B compound said synthetic resin being an cstcrification S h Paris product of an unsubstituted phthalic acid and a dihydric I (sec Example?) alcohol selected from the group consisting of (1) an s'oprfipylmynsmte alkane diol of 2 to 6 carbon atoms, (2) ethers of oly '5 hydric alcohols having 3 to 6 hydroxy groups and in NE" Which the hydroxy groups in excess of two are etherified I chlondc 30-00 by alkyl radicals of 1 to 3 carbon atoms, (3) 4,4'-clil1y Sopropanol 64-70 droxydicyelohexyl; in and (4) mixtures of any one of components 1 to j l less than an equivalent amount; mO'OO with respect to the hitter of a polyhyclric alcohol con (1 contents f l; Part5 tarning at least 3 and at most 6 hydroxy groups, the: B 30 acid
- Example 3 2. A composition as claimed in claim 1, wherein thepolyhydric alcohol is pentaerythritol. in a similar manner to Examples 1 and 2 other polyesters 3. A composition as claimed in claim 1, wherein said also can be used which have been prepared from: polyhydric alcohol component is used in the resin in an (a) parts of phthalic acid, amount in the range from 50-7 equivalent percent a calculated on the amount of drhydric alcohol. ([2) parts of pcntacrythrnol, and
- a composition suitable for use as a hair spray com- 40 parts of ethylene g1; col, or 0 prising a synthetic resin of a melting point above 4-0 C. (02) parts of propanediol 1,2, or r g f a l u d (C3) parts of butancdiomg or 20 up to 8 3 C. uncttontn as aaair so mg compo n san synthetic resin being an estertficatlon product of at least (04) 157 parts of 4,4'-dihydroxydicyclohexylpropane. l
- polyester resins have the following characteristic one 161d Component Selene? from l p 1 1; v lu of phthalic acid and phthahc anhydride with 4,4'-dihy- Melting ran c C. 40/51 52/58 5 /5 /83. Aci lvulucfuinui -105 -110 3 9 -125.
- esterification product containing the acid Resins cl and c4 were, for example, manufactured according to the following formulations.
- the lanolin re- 2 to 6 carbon atoms, (2) ethers of polyhydric alcoholsfinery product was a solid, slightly yellowish wax-like material of the dropping point 59-70 C., which only con- V H v J tained lanolin fraction-s soluble in cold ethanol, did not hfwmg to 6 groups i m whlch the hymmy ha e m un le'lsant Odor and had a saponification groups in excess of two are ctherificd by alkyl radicals of p 1 to 3 carbon atoms, and (3) 4,4-dihydroxydicyclohcx- 05210 ylpropane, and (4) mixtures of any one of components
- the mixture (b) was filled into aerosol containers in p the manner described in Example 1 resin being an esterification product of at least one acid
- a composition suitable for use as a hair spray comalcohol selected from the group consisting of (1) an alkanc (liol of 2 to 6 carbon atoms, (2) others of polyhydric alcohols having 3 to 6 hydroxy groups and in which the hydroxy groups in excess of two are etherificd by alkyl radicals of 1 to 3 carbon atoms, (3) 4,4dihydroxydicyclohexylpropanc, and (4) mixtures of any one of componcnts l to 3 with less than an equivalent amount with respect to the latter of a polyhydric alcohol containing at least 3 and at most 6 hydroxy groups, the acid and the alcohol components being contained in the synthetic resin in an equivalent ratio between 1:1 and 1:125 and the synthetic resin having an acid number between 90 and 120.
- a composition suitable for use as a hair spray comprising a synthetic resin with a melting point above 40 C. up to about 83 C. functioning as a hair setting compound, said synthetic resin being an esterification prodnet of at least one acid component selected from the group consisting of phthalic acid and phthalic anhydridc with 2,2-dimethyl-1,3-propanediol and to equivalent perccnt, calculated on the amount of dihydric alcohol, of pcntacrythritol, said estcrification product containing the acid and the alcohol component in an equivalent ratio between 1:1 and 121.25 and having an acid number between and 120. and said hair spray composition also containing a perfume and a propellant.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC27231A DE1158214B (de) | 1962-06-01 | 1962-06-01 | Haarspray mit einem Gehalt an harzartigen Haarverfestigern |
| DEC28675A DE1256356B (de) | 1962-12-15 | 1962-12-15 | Haarspray mit einem Gehalt an harzartigen Haarverfestigern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3234098A true US3234098A (en) | 1966-02-08 |
Family
ID=25969547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US284349A Expired - Lifetime US3234098A (en) | 1962-06-01 | 1963-05-31 | Phthalic acid hair spray |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3234098A (nl) |
| AT (1) | AT249271B (nl) |
| BE (1) | BE632886A (nl) |
| CH (1) | CH456047A (nl) |
| DE (1) | DE1158214B (nl) |
| FI (1) | FI42986C (nl) |
| FR (1) | FR1359493A (nl) |
| GB (1) | GB995175A (nl) |
| NL (2) | NL291611A (nl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4300580A (en) * | 1977-01-07 | 1981-11-17 | Eastman Kodak Company | Hair grooming method using linear polyesters |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4974627A (en) * | 1989-08-11 | 1990-12-04 | The Specialty Mfg. Co. | Garden hose reel caddy |
| GB9109965D0 (en) * | 1991-05-07 | 1991-07-03 | Unilever Plc | Cosmetic composition |
| US5919440A (en) * | 1997-05-05 | 1999-07-06 | Procter & Gamble Company | Personal care compositions containing an odor masking base |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2465319A (en) * | 1941-07-29 | 1949-03-22 | Du Pont | Polymeric linear terephthalic esters |
| US2752320A (en) * | 1954-12-27 | 1956-06-26 | Chemstrand Corp | Polyester compositions |
| US2957838A (en) * | 1957-06-10 | 1960-10-25 | Monsanto Chemicals | Hair spray composition containing lower alkyl half ester of an ethylenemaleic anhydride copolymer, alcohol and propellant and process for making |
-
0
- NL NL130408D patent/NL130408C/xx active
- BE BE632886D patent/BE632886A/xx unknown
- NL NL291611D patent/NL291611A/xx unknown
-
1962
- 1962-06-01 DE DEC27231A patent/DE1158214B/de active Pending
-
1963
- 1963-05-07 GB GB17991/63A patent/GB995175A/en not_active Expired
- 1963-05-21 AT AT411463A patent/AT249271B/de active
- 1963-05-21 FR FR935466A patent/FR1359493A/fr not_active Expired
- 1963-05-28 CH CH668163A patent/CH456047A/de unknown
- 1963-05-31 US US284349A patent/US3234098A/en not_active Expired - Lifetime
- 1963-05-31 FI FI631122A patent/FI42986C/fi active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2465319A (en) * | 1941-07-29 | 1949-03-22 | Du Pont | Polymeric linear terephthalic esters |
| US2752320A (en) * | 1954-12-27 | 1956-06-26 | Chemstrand Corp | Polyester compositions |
| US2957838A (en) * | 1957-06-10 | 1960-10-25 | Monsanto Chemicals | Hair spray composition containing lower alkyl half ester of an ethylenemaleic anhydride copolymer, alcohol and propellant and process for making |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4300580A (en) * | 1977-01-07 | 1981-11-17 | Eastman Kodak Company | Hair grooming method using linear polyesters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1359493A (fr) | 1964-04-24 |
| BE632886A (nl) | |
| DE1158214B (de) | 1963-11-28 |
| NL291611A (nl) | |
| CH456047A (de) | 1968-05-15 |
| FI42986B (nl) | 1970-09-02 |
| GB995175A (en) | 1965-06-16 |
| FI42986C (fi) | 1970-12-10 |
| AT249271B (de) | 1966-09-12 |
| NL130408C (nl) |
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