CA1107294A - Fatty halo alkanoate quaternaries of dialkylaminopropylamides - Google Patents
Fatty halo alkanoate quaternaries of dialkylaminopropylamidesInfo
- Publication number
- CA1107294A CA1107294A CA271,557A CA271557A CA1107294A CA 1107294 A CA1107294 A CA 1107294A CA 271557 A CA271557 A CA 271557A CA 1107294 A CA1107294 A CA 1107294A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- water
- ester
- chloride
- fatty
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001475 halogen functional group Chemical group 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 239000003974 emollient agent Substances 0.000 claims abstract description 6
- -1 hair conditioning Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 241000772415 Neovison vison Species 0.000 claims description 7
- 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 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 5
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 5
- 239000000174 gluconic acid Substances 0.000 claims description 5
- 235000012208 gluconic acid Nutrition 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 3
- 244000020518 Carthamus tinctorius Species 0.000 claims description 3
- 230000003750 conditioning effect Effects 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 26
- 239000003676 hair preparation Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 26
- 239000000463 material Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 238000007127 saponification reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 229940089960 chloroacetate Drugs 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229940106681 chloroacetic acid Drugs 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 3
- 235000012209 glucono delta-lactone Nutrition 0.000 description 3
- 239000000182 glucono-delta-lactone Substances 0.000 description 3
- 229960003681 gluconolactone Drugs 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RHKPJTFLRQNNGJ-UHFFFAOYSA-N 1,3-benzothiazole-2-carbaldehyde Chemical compound C1=CC=C2SC(C=O)=NC2=C1 RHKPJTFLRQNNGJ-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102100039845 Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-8 Human genes 0.000 description 1
- 101710112841 Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-8 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SKCKOFZKJLZSFA-UHFFFAOYSA-N L-Gulomethylit Natural products CC(O)C(O)C(O)C(O)CO SKCKOFZKJLZSFA-UHFFFAOYSA-N 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical class [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical class C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KUZUNHDCZIJWAO-UHFFFAOYSA-N tetradecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCl KUZUNHDCZIJWAO-UHFFFAOYSA-N 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- 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
- A61Q5/12—Preparations containing hair conditioners
Abstract
ABSTRACT
Novel compositions of matter consisting of fatty halo alkanoate quaternaries of dialkylaminopropyl-amides have been found to be excellent emollients having surprisingly good anti-tangle and anti-static properties in hair preparations. They are prepared by reacting the dialkylaminopropylamides with fatty halo alkanoate esters.
Novel compositions of matter consisting of fatty halo alkanoate quaternaries of dialkylaminopropyl-amides have been found to be excellent emollients having surprisingly good anti-tangle and anti-static properties in hair preparations. They are prepared by reacting the dialkylaminopropylamides with fatty halo alkanoate esters.
Description
11~7~9~
There is an ever-lncreasing need for improved emollients, particularly those having superior hair condition-ing properties in view of the increased emphasis on hair styl~
ing for fashion purposes. This invention provides novel synthetic emollients having outstanding properties for the purposes mentioned.
` Many emollients employed in hair conditioning either left the hair over fatted or static prone. They also presented formulation problems.
As part of the continuing attempt to prepare quater-nary halides of various amides which could overcome these problems, e.g. gluconamide, it was found that reaction with higher alkyl chlorides, e.g. 2-ethyl, hexyl or decyl resulted in the decomposition of the gluconamide at the temperatures (120-140C) necessary to bring about quaternary formation.
This severely limited the synthetic possibilities.
It has now been found that fatty halo alkanoate quaternaries of dialkyl amino propyl amides, corresponding to the following formula:
O R~ O
~R - C - NH - (CH2)x~l (CH2)y R~
wherein the RCO moiety is selected from the group consisting of gluconic acid, and C7-C21 fatty acids, Rt is an alkyl group having from 1 to 2 carbon atoms' x is an integer of from 2 to 3, y is an integer of from 1 to 3, R" is selected from the group consisting of alkyl of 8 to 22 carbons and the radical remaining after removal of OH from sorbitol, and X is halogen, are extremely effective emmolients imparting excellent anti-tangle and C
1~07Z94 1 and anti-static propertiesJ the latter even after dry combing. This is indeed surprising considering properties 3 of the prior art materials. The compositions of this 4 invention furthermore are relatively non-irritating and -- 5 easy to formulate requiring no salt or acid.
6 The novel products of this invention can be 7 prepared as follows: The corresponding oil, or acid, 8 is reacted, e.g. with either gamma dimethylamino or gamma 9 diethylaminopropylamine, at between about 140-160C
using an alkaline catalyst and a nitrogen atmosphere 11 which inhibits oxidation of unsaturated fatty acids.
12 It has been found that an alkaline catalyst such as 13 sodium hydroxide, potassium hydroxide and sodium methylate 14 or ethylate work equally well.
The amide is then quaternized by reaction with 16 the fatty halo alkanoate ester at ~emperatures in the 17 range of about 100 to 110C., utilizing glycols, e.g.
18 propylene glycol, as a solvent.
19 Sources of the R are exemplified by gluconic acid, mink oil fatty acids, safflower fatty acids, 21 hydrogenated tallow triglycerides, corn oil fatty acids, 22 stearic, palmitic, myristic and lauric acids. The 23 sources can be saturated or unsaturated, in the latter 24 case can have up to 3 double bonds conjugated or unconjugated.
26 Especially p~eferred halides are chlorides and 27 bromides.
28 Examples of chloro esters utilized are myristyl;
29 cetyl; and sorbitol chloro acetates; and decyl propionate.
Thus, particularly effective compositions are .
ll~L .
1 those in which the RCO is the moiety from gluconic acid,
There is an ever-lncreasing need for improved emollients, particularly those having superior hair condition-ing properties in view of the increased emphasis on hair styl~
ing for fashion purposes. This invention provides novel synthetic emollients having outstanding properties for the purposes mentioned.
` Many emollients employed in hair conditioning either left the hair over fatted or static prone. They also presented formulation problems.
As part of the continuing attempt to prepare quater-nary halides of various amides which could overcome these problems, e.g. gluconamide, it was found that reaction with higher alkyl chlorides, e.g. 2-ethyl, hexyl or decyl resulted in the decomposition of the gluconamide at the temperatures (120-140C) necessary to bring about quaternary formation.
This severely limited the synthetic possibilities.
It has now been found that fatty halo alkanoate quaternaries of dialkyl amino propyl amides, corresponding to the following formula:
O R~ O
~R - C - NH - (CH2)x~l (CH2)y R~
wherein the RCO moiety is selected from the group consisting of gluconic acid, and C7-C21 fatty acids, Rt is an alkyl group having from 1 to 2 carbon atoms' x is an integer of from 2 to 3, y is an integer of from 1 to 3, R" is selected from the group consisting of alkyl of 8 to 22 carbons and the radical remaining after removal of OH from sorbitol, and X is halogen, are extremely effective emmolients imparting excellent anti-tangle and C
1~07Z94 1 and anti-static propertiesJ the latter even after dry combing. This is indeed surprising considering properties 3 of the prior art materials. The compositions of this 4 invention furthermore are relatively non-irritating and -- 5 easy to formulate requiring no salt or acid.
6 The novel products of this invention can be 7 prepared as follows: The corresponding oil, or acid, 8 is reacted, e.g. with either gamma dimethylamino or gamma 9 diethylaminopropylamine, at between about 140-160C
using an alkaline catalyst and a nitrogen atmosphere 11 which inhibits oxidation of unsaturated fatty acids.
12 It has been found that an alkaline catalyst such as 13 sodium hydroxide, potassium hydroxide and sodium methylate 14 or ethylate work equally well.
The amide is then quaternized by reaction with 16 the fatty halo alkanoate ester at ~emperatures in the 17 range of about 100 to 110C., utilizing glycols, e.g.
18 propylene glycol, as a solvent.
19 Sources of the R are exemplified by gluconic acid, mink oil fatty acids, safflower fatty acids, 21 hydrogenated tallow triglycerides, corn oil fatty acids, 22 stearic, palmitic, myristic and lauric acids. The 23 sources can be saturated or unsaturated, in the latter 24 case can have up to 3 double bonds conjugated or unconjugated.
26 Especially p~eferred halides are chlorides and 27 bromides.
28 Examples of chloro esters utilized are myristyl;
29 cetyl; and sorbitol chloro acetates; and decyl propionate.
Thus, particularly effective compositions are .
ll~L .
1 those in which the RCO is the moiety from gluconic acid,
2 safflower fatty acids, and hydrogenated tallow trigly-
3 cerides; R' is CH3; x is 3; y is 1; R" is (CH2)13; and
4 X is Cl.
This invention, product workup and properties 6 of these novel materials will be better understood by 7 reference to the following examples.
8 EXAMPLE 1 - MYRISTYL 3-CHLOROPROPION~TE OF 3-DIMETHYL-9 AMINOP~OPYL MINK OIL _ATTY ACID AMIDE
170-3g Mink 3-dimethylaminopropylamide 11 152g Myristyl 3-chloropropionate 12 215g propylene glycol 13 After heating the above materials for 4 hours 14 at 110C, the theoretical chloride (2.9%) was obtained.
Analyses: % Ionic Chloride = 2.9%
16 V/~ Solids = 60~/o 17 ~/0 Propylene glycol = 40/0 ~ -18 EXAMPLE 2 - SORBITOL CHLORO ACETATE QUATERNARY OF ~-19 DIMETHYLAMINOPROPYLAMIDE OF MI~ OIL FATTY
ACIDS
21 193g Mink oil amide 22 137g Sorbitol chloro acetate 23 220g propylene glycol 24 The above materials were heated at 110C for 2 hours in order to obtain the theoretical 3.2% ionic 26 chloride. Product is a light amber viscous liquid at 27 room temperature.
28 Analyses: % Ionic Chloride = 3.2%
i 29 % Solids = 60%
% Propylene glycol = 40%
33 Part A: [Amide ~ormation]
34 Mink oil, a mixture of triglyceride containing .
9~
1 myristic, palmitic, palmitoleic, stearic, oleic and 2 linoleic acids, is reacted with 3-dimethylaminopropyl-3 amide using potassium hydroxide as the transamidation 4 catalyst.
164g Mink oil 6 74g Diethylaminopropylamine 7 2g KOH
8 The above materials were heated, with agitation 9 in a flask, at 140-150C for 6 hrs. under a nitrogen atmosphere. An alkali number of 152 was obtained.
11 Part Bl: [Quaternary formation]
12 After cooling the above material to 50C, -13 201g of water and 201g propylene glycol were added.
14 The mixture was agitated until homogeneous, then 162g of myristyl chloro acetate was added. The required ionic 16 chloride of 2.5 was obtained after refluxing at 105C
17 for 10-12 hrs.
18 Analyses: /O Ionic chloride = 2~5~/o 19 % Solids = 50/O
~/D Water = 25%
21 % Propylene glycol = 25%
22 Part B2: [Quaternary formation]
23 192.5g Mink amide 24 159.5g Myristyl chloro acetate 234.5g Propylene glycol 2~ The theoretical chloride of 3% was obtained 27 by heating the above materials at 110C. for 2% hrs.
28 Analyses: % Ionic chloride = 3~/O
29 % Solids = 60%
% Propylene glycol = 4G%
31 This material has the advantage over the 32 product described in Bl in that it is a liquid with the ~ 10~29 ~
1 viscosity of glycerol at room temperature, the other 2 material is a gel when cooled to room temperature.
.
Part A: [3-dimethylaminopropyl gluconamide]
6 178g Glucono delta lactone 7 102g Dimethylaminopropylamine 8 571g Isopropanol ~
9 An acid value of 0. 3 was obtained after refluxing the above materials at 87C for 1 hr.
11 Part B: [Quaternary formation]
12 After cooling the above solution to 50~/O~ 2~1g 13 of myristyl chloro acetate was added. The ionic chloride 14 reached a maximum value of 2~9% [3~1~/o is theoretical~
after refluxing at 86C ~or 5 hrs. Upon cooling to 16 room temperature, the solution solidified into a so~t 17 solid.
18 Analyses: a/o Ionic chloride - 2 ~ 9%
19 % Solids = 50%
% Isopropanol = 50~/O
21 2~/o Solution in ethanol ~ insoluble 22 2% Solution in water - dispersible 23 EXAMPLE 5 DODECYL CHLORO ACET~TE QU~TE~NARY OF 3-24 DIMETHYLAMINOPROPYL GLUCON~IDE
25 Part A: ~3-dimethylaminopropyl gluconamide]
26 178g Glucono delta lactone 27 102g Dimethylaminopropylamine 28 543g Isopropanol 29 After heating the above mixture under reflux at 87 C for 1 hr. an acid value 0. 2 was obtained. The 31 mixture was cooled to 50C.
32 Part B: [Quaternary formation]
33 To the above solution 263g lauryl chloro acetate 11`~7294 1 was added. An ionic chloride of 3.3% ~theoretical]
2 was ob~ained after a 5 hr. reflux. Product solution 3 cooled to 50C and transferred to a jar, where, upon 4 cooling to room temperature, it became a soft solid.
This invention, product workup and properties 6 of these novel materials will be better understood by 7 reference to the following examples.
8 EXAMPLE 1 - MYRISTYL 3-CHLOROPROPION~TE OF 3-DIMETHYL-9 AMINOP~OPYL MINK OIL _ATTY ACID AMIDE
170-3g Mink 3-dimethylaminopropylamide 11 152g Myristyl 3-chloropropionate 12 215g propylene glycol 13 After heating the above materials for 4 hours 14 at 110C, the theoretical chloride (2.9%) was obtained.
Analyses: % Ionic Chloride = 2.9%
16 V/~ Solids = 60~/o 17 ~/0 Propylene glycol = 40/0 ~ -18 EXAMPLE 2 - SORBITOL CHLORO ACETATE QUATERNARY OF ~-19 DIMETHYLAMINOPROPYLAMIDE OF MI~ OIL FATTY
ACIDS
21 193g Mink oil amide 22 137g Sorbitol chloro acetate 23 220g propylene glycol 24 The above materials were heated at 110C for 2 hours in order to obtain the theoretical 3.2% ionic 26 chloride. Product is a light amber viscous liquid at 27 room temperature.
28 Analyses: % Ionic Chloride = 3.2%
i 29 % Solids = 60%
% Propylene glycol = 40%
33 Part A: [Amide ~ormation]
34 Mink oil, a mixture of triglyceride containing .
9~
1 myristic, palmitic, palmitoleic, stearic, oleic and 2 linoleic acids, is reacted with 3-dimethylaminopropyl-3 amide using potassium hydroxide as the transamidation 4 catalyst.
164g Mink oil 6 74g Diethylaminopropylamine 7 2g KOH
8 The above materials were heated, with agitation 9 in a flask, at 140-150C for 6 hrs. under a nitrogen atmosphere. An alkali number of 152 was obtained.
11 Part Bl: [Quaternary formation]
12 After cooling the above material to 50C, -13 201g of water and 201g propylene glycol were added.
14 The mixture was agitated until homogeneous, then 162g of myristyl chloro acetate was added. The required ionic 16 chloride of 2.5 was obtained after refluxing at 105C
17 for 10-12 hrs.
18 Analyses: /O Ionic chloride = 2~5~/o 19 % Solids = 50/O
~/D Water = 25%
21 % Propylene glycol = 25%
22 Part B2: [Quaternary formation]
23 192.5g Mink amide 24 159.5g Myristyl chloro acetate 234.5g Propylene glycol 2~ The theoretical chloride of 3% was obtained 27 by heating the above materials at 110C. for 2% hrs.
28 Analyses: % Ionic chloride = 3~/O
29 % Solids = 60%
% Propylene glycol = 4G%
31 This material has the advantage over the 32 product described in Bl in that it is a liquid with the ~ 10~29 ~
1 viscosity of glycerol at room temperature, the other 2 material is a gel when cooled to room temperature.
.
Part A: [3-dimethylaminopropyl gluconamide]
6 178g Glucono delta lactone 7 102g Dimethylaminopropylamine 8 571g Isopropanol ~
9 An acid value of 0. 3 was obtained after refluxing the above materials at 87C for 1 hr.
11 Part B: [Quaternary formation]
12 After cooling the above solution to 50~/O~ 2~1g 13 of myristyl chloro acetate was added. The ionic chloride 14 reached a maximum value of 2~9% [3~1~/o is theoretical~
after refluxing at 86C ~or 5 hrs. Upon cooling to 16 room temperature, the solution solidified into a so~t 17 solid.
18 Analyses: a/o Ionic chloride - 2 ~ 9%
19 % Solids = 50%
% Isopropanol = 50~/O
21 2~/o Solution in ethanol ~ insoluble 22 2% Solution in water - dispersible 23 EXAMPLE 5 DODECYL CHLORO ACET~TE QU~TE~NARY OF 3-24 DIMETHYLAMINOPROPYL GLUCON~IDE
25 Part A: ~3-dimethylaminopropyl gluconamide]
26 178g Glucono delta lactone 27 102g Dimethylaminopropylamine 28 543g Isopropanol 29 After heating the above mixture under reflux at 87 C for 1 hr. an acid value 0. 2 was obtained. The 31 mixture was cooled to 50C.
32 Part B: [Quaternary formation]
33 To the above solution 263g lauryl chloro acetate 11`~7294 1 was added. An ionic chloride of 3.3% ~theoretical]
2 was ob~ained after a 5 hr. reflux. Product solution 3 cooled to 50C and transferred to a jar, where, upon 4 cooling to room temperature, it became a soft solid.
5 Analyses: % Ionic chloride = 3.3%
6 % Solids = 50%
7 ~/O Isopropanol = 50a/O
8 2~/o Solution in ethanol = insoluble
9 2~/o Solution in water = dispersible
10 EXAMPLE 6 - DECYL CHLORO ACETATE QUATERNARY OF 3-
11 _ DIMETHYLAMINOPROPYL GLUCONAMIDE
12 Part A: [3-dimethylaminopropyl gluconamide]
13 178g Glucono delta lactone
14 102g Dimethylaminopropylamine 515g Isopropanol 16 The above materials were heated under reflux 17 in a 2 liter flask equipped with a thermometer, stirrer 18 and reflux condenser, for 1 hour. An acid value of 0.2 19 indicates complete reaction.
Part B: ~Quaternary formation]
21 After cooling to about 60C, 235g of decylchloro 22 acetate was added. An ionic chloride of 3.4% [3.4% is 23 theoretical] was obtained after a 5 hour reflux at 86C.
24 After cooling to 50C, the liquid was poured into a jar, where upon coollng to room temperature, the material 26 became a soft solid.
27 Analyses: Ionic chloride - 3.4%
28 % Solids = 50%
i 29 % Isopropanol = 50%
2% Solution in ethanol - insoluble 31 2~/~ Solution in water - dispersible 33 Charge: 520g Sorbitol (70% solution) 34 189g Chloro acetic acid 150g Toluene ..
~ 7~29 ~
1 The above materials were heated under reflux 2 in a 2 liter flask fitted with a thermometer, stirrer 3 and water trap. Most of the water [188g] was removed 4 at or below 90C. An acid value of 18.4 was obtained at this point. Heating at 110C for an additicnal hour 6 yielded an additional 18g of water; the acid value was 7 reduced to 3.8% where it remained.
8 Upon cooling a clear very viscous liquid was 9 obtained.
10 Analyses: Acid value = 3~ 8~/o 11 Saponification value = 453.5 12 % Chloride = 13.9%
13 EXAMPLE 8 ~ OCTADECYL MONOCHLORO ACETATE
14 Charge; 540g Octadecyl alcohol (stearyl) l99g Chloro acetic acid 16 200 ml toluene 17 36g water to be removed 18 The above material was refluxed in a 2 liter 19 flask equipped with a thermometer, stirrer, water separator, to a maximum temperature of 139C. After 21 1~ hrs. all the water ~36g] was removed.
22 After neutralizing with 5~/O sodium carbonate 23 and water, toluene was removed under water jet vacuum 24 in a pot temperature of 129C. High vacuum distillation of the crude gave the following results:
26 Fr.#l 198-201C/3 min. 58g 27 Fr.#2 124C/3 min. 400g 28 Fr.#3 125C/3 min. 194g 29 nal~ses of Fractions:
1st fraction ~cid value = 1.8 31 Saponification = 307.6 32 % Chloride = 9.7~/~
33 % Ester = 94.5%
34 % alcohol = 5.5%
llU7294 1 2nd fraction Acid value = 0.7 2 Saponification value - 321.2 3 /O Chloride - 10. l~/o 4 % Ester = 99%
% Alcohol = 1%
6 3rd fraction Acid value = 0.5 7 Saponification value = 320.4 8 % Chloride =! 10 ~ O
g r/O Ester = 98.8%
% Alcohol = 1.2%
11 Total weight of ester = 642.4g 12 Yield of ester - 92~7~/o of theory 14 Charge: l90g Chloro acetic acid 428g Tetradecyl alcohol (myristyl) 16 250 ml toluene 17 lg para toluene sulfonic acid 18 36g of water to be removed 19 After re~luxing the above materials in a 2 liter flaskl equipped with a thermometer, stirrer, and 21 water separator~ for 1~ hrs, the required amount of 22 water was collected. The maximum temperature reached 23 during this reflux period was 141C.
24 The ester solution was neutralized with 5%
sodium carbonate and washed free of excess alkali with 26 water.
27 Toluene was removed under water jet vacuum 28 [max. temp. 140C] and the crude distilled under high 29 vacuum.
Fr.~l 150-160C/1 min. 106g 31 Fr.$2 160-169C/1 miA. 450g - _ g _ ,.
1 Analyses of_Fractions:
2 1st fraction Acid value = 0.50 3 Saponfication value - 160.2 4 % Chloride = 10.1%
% Ester = 83~
6 % Alcohol = 17~/o 7 2nd fraction Acid value = 0.13 -8 Saponification value = 181 9 % Chloride - 11.5% ~:
% Ester = 94%
11 % Alcohol = 6%
12 Total ester content - 511g 13 Yield of ester = 88% of theory
Part B: ~Quaternary formation]
21 After cooling to about 60C, 235g of decylchloro 22 acetate was added. An ionic chloride of 3.4% [3.4% is 23 theoretical] was obtained after a 5 hour reflux at 86C.
24 After cooling to 50C, the liquid was poured into a jar, where upon coollng to room temperature, the material 26 became a soft solid.
27 Analyses: Ionic chloride - 3.4%
28 % Solids = 50%
i 29 % Isopropanol = 50%
2% Solution in ethanol - insoluble 31 2~/~ Solution in water - dispersible 33 Charge: 520g Sorbitol (70% solution) 34 189g Chloro acetic acid 150g Toluene ..
~ 7~29 ~
1 The above materials were heated under reflux 2 in a 2 liter flask fitted with a thermometer, stirrer 3 and water trap. Most of the water [188g] was removed 4 at or below 90C. An acid value of 18.4 was obtained at this point. Heating at 110C for an additicnal hour 6 yielded an additional 18g of water; the acid value was 7 reduced to 3.8% where it remained.
8 Upon cooling a clear very viscous liquid was 9 obtained.
10 Analyses: Acid value = 3~ 8~/o 11 Saponification value = 453.5 12 % Chloride = 13.9%
13 EXAMPLE 8 ~ OCTADECYL MONOCHLORO ACETATE
14 Charge; 540g Octadecyl alcohol (stearyl) l99g Chloro acetic acid 16 200 ml toluene 17 36g water to be removed 18 The above material was refluxed in a 2 liter 19 flask equipped with a thermometer, stirrer, water separator, to a maximum temperature of 139C. After 21 1~ hrs. all the water ~36g] was removed.
22 After neutralizing with 5~/O sodium carbonate 23 and water, toluene was removed under water jet vacuum 24 in a pot temperature of 129C. High vacuum distillation of the crude gave the following results:
26 Fr.#l 198-201C/3 min. 58g 27 Fr.#2 124C/3 min. 400g 28 Fr.#3 125C/3 min. 194g 29 nal~ses of Fractions:
1st fraction ~cid value = 1.8 31 Saponification = 307.6 32 % Chloride = 9.7~/~
33 % Ester = 94.5%
34 % alcohol = 5.5%
llU7294 1 2nd fraction Acid value = 0.7 2 Saponification value - 321.2 3 /O Chloride - 10. l~/o 4 % Ester = 99%
% Alcohol = 1%
6 3rd fraction Acid value = 0.5 7 Saponification value = 320.4 8 % Chloride =! 10 ~ O
g r/O Ester = 98.8%
% Alcohol = 1.2%
11 Total weight of ester = 642.4g 12 Yield of ester - 92~7~/o of theory 14 Charge: l90g Chloro acetic acid 428g Tetradecyl alcohol (myristyl) 16 250 ml toluene 17 lg para toluene sulfonic acid 18 36g of water to be removed 19 After re~luxing the above materials in a 2 liter flaskl equipped with a thermometer, stirrer, and 21 water separator~ for 1~ hrs, the required amount of 22 water was collected. The maximum temperature reached 23 during this reflux period was 141C.
24 The ester solution was neutralized with 5%
sodium carbonate and washed free of excess alkali with 26 water.
27 Toluene was removed under water jet vacuum 28 [max. temp. 140C] and the crude distilled under high 29 vacuum.
Fr.~l 150-160C/1 min. 106g 31 Fr.$2 160-169C/1 miA. 450g - _ g _ ,.
1 Analyses of_Fractions:
2 1st fraction Acid value = 0.50 3 Saponfication value - 160.2 4 % Chloride = 10.1%
% Ester = 83~
6 % Alcohol = 17~/o 7 2nd fraction Acid value = 0.13 -8 Saponification value = 181 9 % Chloride - 11.5% ~:
% Ester = 94%
11 % Alcohol = 6%
12 Total ester content - 511g 13 Yield of ester = 88% of theory
15 Charge: 372g Dodecyl alcohol (lauryl)
16 209g Chloro acetic acid
17 250 ml toluene
18 36g water to be removed
19 The required amount of water (36g) was removed after refluxing the above materials, in a 2 liter flask 21 fitted with a thermometer, stirrer and water trap, for an 22 hour to a maximum temperature of 138C.
23 After neutraliza~ion of the cooled ester 24 solution with 5% sodium bicarbonate and water, the the toluene was removed under water jet vacuum to a 26 pot temperature of 135C. A high vacuum distillation 27 of the crude ester gave the following results:
28 Fr.~l 130-135C/3 min. 89g 29 Fr.~2 135-152C/3 min. 419g Analyses of Fractions:
31 1st fraction Acid value = 0.56 32 Saponification value = 109 33 % Chloride = 6.9%
34 % Ester = 53%
% ~lcohol = 47%
1 1~7~Z9 1 2nd fraction Acid value ~ 0.25 2 Saponification value = 205 3 % Chloride = 13~/o 4 ~/4 Ester = 100%
Total ester content = 461g 6 Yield = 84.6V/~ theory 7 EXAMPLE 11 - DEC~L MONOC~LORO ACETATE
8 Charge: 316g Decyl alcohol 9 208g Monochloro acetic acid lg Para toluene sulfonic acid 11 250 ml Toluene 12 36g water to be removed 13 The above materials were refluxed in a 2 liter 14 flask equipped with a thermometer, stirrer and water trap which was fitted with a reflux condenser. The 16 required 36g of water was collected after refluxing, at .i --17 a maximum temperature of 137C, for 1~ hrs.
18 Upon cooling the crude ester solution was 19 washed neutral with 5% sodium bicarbonate followed with r water.
21 Toluene was removed under water jet vacuum to 22 a pot temperature of 135C; crude ester was distilled 23 under high vacuum.
24 Fr.#l 113-127C/3 min. 123g Fr.#2 128-130Ct3 min. 325g 26 Analyses of Fractions:
27 1st fraction Acid value = 0.3 28 Saponification value = 189 ?
29 % Chloride = 11.8%
% Ester = 79%
31 % Decanol = 21%
32 2nd fraction Acid value = 0.15 33 Saponification value = 239 34 % Chloride = 15%
% Ester = 100%
, 1 Total ester content = 422.2g 2 Yield = 90% of theory 3 EX~'LE 12 - TETRaDECYL 3-CHLORO PROPIONATE
, ~ 4 Charge: 100g 3-chloro propionic acid - 5 197g Tetradecyl (myristyl) alcohol 6 lO0g Toluene 7 17.9g water to be removed 8 After refluxing the above material, in a 9 1 liter flask fitted with a stirrer, thermometer and ; lO water trap~ for four hours (maximum temp. 148 C) the 11 required amount of water was removed. The resulting 12 ester solution was neutralized with 5% sodium bicarbonate 13 solution, then washed free of alkali with water.
14 Toluene was removed under water jet vacuum to a pot temperature of 125C~ The crude ester was distilled 16 under high vacuum.
17 Fr-#l 165-195C/1 min. 42g 18 Fr.1~2 195C/1 min. 205g 19 Analyses of_Fractions:
1st fraction Acid value = 1.2 21 Saponification value = 22~1 22 % Chloride = 1.4%
23 % Ester - 12%
24 % Alcohol = 88%
2nd fraction Acid value = 0.3 26 Saponification value = 162 27 % Chloride = 10.3 28 % Ester = 88%
29 % Alcohol = 12~/o Wt. of ester = 185~4g ~ 31 Yield = 89~1o of theory : 32 The materials of this invention can be formulated 33 in a variety of manners, e.g. oil in water lotions, or ' ..
29~
1 aqueous solutions as a final rinse, as will be readily 2 apparent to the skilled in the art. Typically, the 3 active component is utilized in a concentration of 0.05 4 wt.V/o - 5 wt.V/o; preferably 0.1 - 3 wt.V/o. Good results have been obtained within these ranges.
6 The advantages of this invention will be 7 appatent to the skilled in the art. Novel, non-8 irritating emollients of superior properties are 9 provided from readily available sources.
23 After neutraliza~ion of the cooled ester 24 solution with 5% sodium bicarbonate and water, the the toluene was removed under water jet vacuum to a 26 pot temperature of 135C. A high vacuum distillation 27 of the crude ester gave the following results:
28 Fr.~l 130-135C/3 min. 89g 29 Fr.~2 135-152C/3 min. 419g Analyses of Fractions:
31 1st fraction Acid value = 0.56 32 Saponification value = 109 33 % Chloride = 6.9%
34 % Ester = 53%
% ~lcohol = 47%
1 1~7~Z9 1 2nd fraction Acid value ~ 0.25 2 Saponification value = 205 3 % Chloride = 13~/o 4 ~/4 Ester = 100%
Total ester content = 461g 6 Yield = 84.6V/~ theory 7 EXAMPLE 11 - DEC~L MONOC~LORO ACETATE
8 Charge: 316g Decyl alcohol 9 208g Monochloro acetic acid lg Para toluene sulfonic acid 11 250 ml Toluene 12 36g water to be removed 13 The above materials were refluxed in a 2 liter 14 flask equipped with a thermometer, stirrer and water trap which was fitted with a reflux condenser. The 16 required 36g of water was collected after refluxing, at .i --17 a maximum temperature of 137C, for 1~ hrs.
18 Upon cooling the crude ester solution was 19 washed neutral with 5% sodium bicarbonate followed with r water.
21 Toluene was removed under water jet vacuum to 22 a pot temperature of 135C; crude ester was distilled 23 under high vacuum.
24 Fr.#l 113-127C/3 min. 123g Fr.#2 128-130Ct3 min. 325g 26 Analyses of Fractions:
27 1st fraction Acid value = 0.3 28 Saponification value = 189 ?
29 % Chloride = 11.8%
% Ester = 79%
31 % Decanol = 21%
32 2nd fraction Acid value = 0.15 33 Saponification value = 239 34 % Chloride = 15%
% Ester = 100%
, 1 Total ester content = 422.2g 2 Yield = 90% of theory 3 EX~'LE 12 - TETRaDECYL 3-CHLORO PROPIONATE
, ~ 4 Charge: 100g 3-chloro propionic acid - 5 197g Tetradecyl (myristyl) alcohol 6 lO0g Toluene 7 17.9g water to be removed 8 After refluxing the above material, in a 9 1 liter flask fitted with a stirrer, thermometer and ; lO water trap~ for four hours (maximum temp. 148 C) the 11 required amount of water was removed. The resulting 12 ester solution was neutralized with 5% sodium bicarbonate 13 solution, then washed free of alkali with water.
14 Toluene was removed under water jet vacuum to a pot temperature of 125C~ The crude ester was distilled 16 under high vacuum.
17 Fr-#l 165-195C/1 min. 42g 18 Fr.1~2 195C/1 min. 205g 19 Analyses of_Fractions:
1st fraction Acid value = 1.2 21 Saponification value = 22~1 22 % Chloride = 1.4%
23 % Ester - 12%
24 % Alcohol = 88%
2nd fraction Acid value = 0.3 26 Saponification value = 162 27 % Chloride = 10.3 28 % Ester = 88%
29 % Alcohol = 12~/o Wt. of ester = 185~4g ~ 31 Yield = 89~1o of theory : 32 The materials of this invention can be formulated 33 in a variety of manners, e.g. oil in water lotions, or ' ..
29~
1 aqueous solutions as a final rinse, as will be readily 2 apparent to the skilled in the art. Typically, the 3 active component is utilized in a concentration of 0.05 4 wt.V/o - 5 wt.V/o; preferably 0.1 - 3 wt.V/o. Good results have been obtained within these ranges.
6 The advantages of this invention will be 7 appatent to the skilled in the art. Novel, non-8 irritating emollients of superior properties are 9 provided from readily available sources.
Claims (6)
1. As a novel emollient, hair conditioning, composition of matter a fatty halo alkanoate quaternary of dialkyl amino propyl amides, corresponding to the formula wherein the RCO moiety is selected from the group consisting of gluconic acid, and C7-C21 fatty acids, R' is an alkyl group having from 1 to 2 carbon atoms; x is an integer of from 2 to 3;
y is an integer of from 1 to 3; R" is selected from the group consisting of alkyl of 8 to 22 carbons and the radical remain-ing after removal of OH from sorbitol, and X is halogen.
y is an integer of from 1 to 3; R" is selected from the group consisting of alkyl of 8 to 22 carbons and the radical remain-ing after removal of OH from sorbitol, and X is halogen.
2. The composition of claim 1 in which R' is CH3; x is 3, y is 1; R" is (CH2)13; and X is C1.
3. The composition of claim 2 in which the RCO moiety is gluconic acid.
4. The composition of claim 2 in which the RCO moiety is safflower fatty acids.
5. The composition of claim 2 in which the RCO moiety is hydrogenated tallow triglycerides.
6. The composition of claim 2 in which the RCO moiety is mink oil fatty acids.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/676,416 US4038294A (en) | 1976-04-13 | 1976-04-13 | Fatty halo alkanoate quaternaries of dialkylaminopropylamides |
| US676,416 | 1976-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1107294A true CA1107294A (en) | 1981-08-18 |
Family
ID=24714420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA271,557A Expired CA1107294A (en) | 1976-04-13 | 1977-02-11 | Fatty halo alkanoate quaternaries of dialkylaminopropylamides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4038294A (en) |
| JP (1) | JPS52125123A (en) |
| AU (1) | AU508299B2 (en) |
| CA (1) | CA1107294A (en) |
| DE (1) | DE2708823C2 (en) |
| FR (1) | FR2348190A1 (en) |
| GB (1) | GB1516496A (en) |
| IT (1) | IT1073241B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507280A (en) * | 1979-07-02 | 1985-03-26 | Clairol Incorporated | Hair conditioning composition and method for use |
| US4663158A (en) * | 1979-07-02 | 1987-05-05 | Clairol Incorporated | Hair conditioning composition containing cationic polymer and amphoteric surfactant and method for use |
| US4370272A (en) * | 1980-01-14 | 1983-01-25 | Stepan Chemical Company | Alkoxylated quaternary ammonium surfactants |
| US4529586A (en) * | 1980-07-11 | 1985-07-16 | Clairol Incorporated | Hair conditioning composition and process |
| DE3505269A1 (en) * | 1985-02-15 | 1986-08-21 | Hoechst Ag, 6230 Frankfurt | QUARTERNAERE ALKYLAMIDOBETAINESTER, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN SOFT SOFTEN DETERGENTS |
| US4738787A (en) * | 1987-05-26 | 1988-04-19 | Alkaril Chemicals Inc. | Cationic soil release polymers |
| US4804483A (en) * | 1987-05-26 | 1989-02-14 | Gaf Corporation | Cationic soil release polymers |
| US5139784A (en) * | 1990-03-13 | 1992-08-18 | Revlon, Inc. | Alkyl diamides and cosmetic treating compositions therewith |
| SE9001862D0 (en) * | 1990-05-23 | 1990-05-23 | Berol Nobel Ab | NEW NUCLEAR CONTAINING SOCIETIES, PROCEDURES FOR THEIR PREPARATION AND USE OF SOCIETIES |
| DE4205880A1 (en) * | 1992-02-26 | 1993-09-02 | Goldschmidt Ag Th | PROCESS FOR THE PRODUCTION OF BETAINES |
| US5521293A (en) * | 1992-11-25 | 1996-05-28 | Lever Brothers Company, Division Of Conopco, Inc. | Heteroatom containing alkyl aldonamide compounds as superior foaming, more soluble nonionic surfactants and a process for their manufacture |
| ES2080655B1 (en) * | 1993-07-15 | 1996-10-16 | Lorente Hidalgo Antonio | NEW POLYFUNCTIONAL CATIONIC SURFACTANTS, COMPOSITIONS BASED ON THEM, PROCEDURE FOR THEIR PREPARATION AND APPLICATIONS. |
| JP3357453B2 (en) * | 1993-09-10 | 2002-12-16 | 花王株式会社 | Liquid soft finish composition, novel quaternary ammonium salt and method for producing the salt |
| US5525261A (en) * | 1994-10-18 | 1996-06-11 | Henkel Corporation | Anti-static composition and method of making the same |
| US5641480A (en) * | 1994-12-08 | 1997-06-24 | Lever Brothers Company, Division Of Conopco, Inc. | Hair care compositions comprising heteroatom containing alkyl aldonamide compounds |
| US5653970A (en) * | 1994-12-08 | 1997-08-05 | Lever Brothers Company, Division Of Conopco, Inc. | Personal product compositions comprising heteroatom containing alkyl aldonamide compounds |
| US6107498A (en) * | 1997-04-22 | 2000-08-22 | Akzo Nobel N.V. | Process for making carboxylic amides |
| JP3853549B2 (en) * | 1999-11-10 | 2006-12-06 | 花王株式会社 | Functional alcohol release material |
| CN1225235C (en) * | 2000-07-03 | 2005-11-02 | 花王株式会社 | Deodorant compositions |
| JP2005516045A (en) | 2002-01-31 | 2005-06-02 | クローダ，インコーポレイテッド | Additives and products containing oligoesters |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686795A (en) * | 1950-11-20 | 1954-08-17 | Lankro Chem Ltd | Carboxylic acid amido-alkyl-amino ester salts |
| US2777872A (en) * | 1953-11-02 | 1957-01-15 | Du Pont | Unsaturated organic compounds |
| US2710876A (en) * | 1953-12-09 | 1955-06-14 | Ernst T Krebs | Nu-substituted glycine esters of gluconic acid |
| US3225074A (en) * | 1959-12-28 | 1965-12-21 | American Cyanamid Co | Betaines |
| FR1339123A (en) * | 1961-11-06 | 1963-10-04 | Ciba Geigy | New quaternary ammonium compounds and process for their preparation |
| US3492324A (en) * | 1963-04-26 | 1970-01-27 | I C I Organics Inc | Quaternary salts of tertiary amines |
| US3751451A (en) * | 1970-05-26 | 1973-08-07 | Kendall & Co | Monomeric emulsion stabilizers derived from alkyl/alkenyl succinic anhydride |
| US3855290A (en) * | 1971-03-03 | 1974-12-17 | Dyk & Co Inc Van | Quaternary halides of gluconamides |
| US3959461A (en) * | 1974-05-28 | 1976-05-25 | The United States Of America As Represented By The Secretary Of Agriculture | Hair cream rinse formulations containing quaternary ammonium salts |
-
1976
- 1976-04-13 US US05/676,416 patent/US4038294A/en not_active Expired - Lifetime
-
1977
- 1977-02-11 CA CA271,557A patent/CA1107294A/en not_active Expired
- 1977-02-21 AU AU22477/77A patent/AU508299B2/en not_active Expired
- 1977-03-01 DE DE2708823A patent/DE2708823C2/en not_active Expired
- 1977-03-04 GB GB9265/77A patent/GB1516496A/en not_active Expired
- 1977-03-31 FR FR7709743A patent/FR2348190A1/en active Granted
- 1977-04-05 IT IT48833/77A patent/IT1073241B/en active
- 1977-04-12 JP JP4247977A patent/JPS52125123A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2708823C2 (en) | 1986-11-20 |
| JPS6135968B2 (en) | 1986-08-15 |
| IT1073241B (en) | 1985-04-13 |
| FR2348190B1 (en) | 1980-12-26 |
| US4038294A (en) | 1977-07-26 |
| AU2247777A (en) | 1978-08-31 |
| AU508299B2 (en) | 1980-03-13 |
| GB1516496A (en) | 1978-07-05 |
| JPS52125123A (en) | 1977-10-20 |
| DE2708823A1 (en) | 1977-11-03 |
| FR2348190A1 (en) | 1977-11-10 |
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