US4028378A
Expired / Lapsed
US
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Fatty and benzoic acid esters of ethoxylated hydantoins substituted or not in the 5-position
Assignee: Glyco Inc
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Filing: 1975-11-17
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Granted: 1977-06-07
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Expires: 1995-11-17
Abstract
Abstract Esters of 1,3-dihydroxyethyl group-containing-hydantoins having the structural formula ##STR1## wherein each of R 3 and R 4 separately is hydrogen, lower alkyl, cycloalkyl, or alkoxy and when either or each of R 3 and R 4 is alkyl, cycloalkyl or alkoxy, they jointly have at most 7 carbons, or R 3 and R 4 jointly are the divalent tetramethylene or pentamethylene chain; either one of R 1 and R 2 is hydrogen, and the other one or each of them is acetoyl, benzoyl, isostearoyl, oleoyl, linoleoyl, linolenoyl, or saturated fatty acyl having from 2 to about 22 carbons or a mixture of saturated fatty acyl groups having from 8 to about 22 carbons or a mixture of any of said saturated fatty acyl groups with any of oleoyl, linoleoyl and linolenoyl, palmitoleoyl and myristoleoyl; and each of x and y varies from each of them being 1 to their sum averaging from 2 to about 100; and mixtures of any of said esters.
Inventors
- 👤 Donald Edward MacFadyen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 05:14
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C08G; C08G65/00; C08G65/02; C08G65/26; C08G65/2618; C08G65/2621; C08G65/263; C08G65/32; C08G65/329; C08G65/331; C08G65/332; C08G65/3322; C08L; C08L101/00; Y; Y10; Y10S; Y10S524/00; Y10S524/91
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
162 words
Esters of 1,3-dihydroxyethyl group-containing-hydantoins having the structural formula ##STR3## wherein each of R 3 and R 4 separately is hydrogen, lower alkyl, cycloalkyl, or alkoxy and when either or each of R 3 and R 4 is alkyl, cycloalkyl or alkoxy, they jointly have at most 7 carbons, or R 3 and R 4 jointly are the divalent tetramethylene or pentamethylene chain; either one of R 1 and R 2 is hydrogen, and the other one or each of them is benzoyl, isostearoyl, oleoyl, linoleoyl, linolenoyl, or saturated fatty acyl having from 2 to about 22 carbons or a mixture of saturated fatty acyl groups having from 8 to about 22 carbons or a mixture of any of said saturated fatty acyl groups with any of oleoyl, linoleoyl and linolenoyl, palmitoleoyl and myristoleoyl; and each of x and y varies from each of them being 1 to their sum averaging from 2 to about 100; and mixtures of any of said esters.
Claim 2
Dependent Claim
162 words
Esters of 1,3-dihydroxyethyl group-containing-hydantoins having the structural formula ##STR3## wherein each of R 3 and R 4 separately is hydrogen, lower alkyl, cycloalkyl, or alkoxy and when either or each of R 3 and R 4 is alkyl, cycloalkyl or alkoxy, they jointly have at most 7 carbons, or R 3 and R 4 jointly are the divalent tetramethylene or pentamethylene chain; either one of R 1 and R 2 is hydrogen, and the other one or each of them is benzoyl, isostearoyl, oleoyl, linoleoyl, linolenoyl, or saturated fatty acyl having from 2 to about 22 carbons or a mixture of saturated fatty acyl groups having from 8 to about 22 carbons or a mixture of any of said saturated fatty acyl groups with any of oleoyl, linoleoyl and linolenoyl, palmitoleoyl and myristoleoyl; and each of x and y varies from each of them being 1 to their sum averaging from 2 to about 100; and mixtures of any of said esters.
Claim 3
Dependent Claim
43 words
The esters or mixtures of them as claimed in claim 1, wherein each of R 3 and R 4 is methyl and each of x and y varies from each of them being 1 to their sum averaging from 2 to about 20.
Claim 4
Dependent Claim
29 words
The esters or mixtures of them as claimed in claim 2, wherein each of R 3 and R 4 is methyl and each of x and y is 1.
Claim 5
Dependent Claim
38 words
A mixture of esters as claimed in claim 3, wherein each of R 1 and R 2 is a mixture of the acyl groups of the fatty acids contained in the commercial white oil grade of oleic acid.
Claim 6
Dependent Claim
57 words
A mixture of esters as claimed in claim 4, wherein from about 80 to about 88.5 percent of the acyl groups R 1 and R 2 are those of the total "oleic" acids of that commercial oleic acid and the remainder of the acyl groups are those of the saturated fatty acids of that commercial oleic acid.
Claim 7
Dependent Claim
67 words
A mixture of esters as claimed in claim 5, wherein the commercial white oil grade of oleic acid consists essentially of about 72.5% of 9-cis-octadecenoic acid, about 8.6% of linoleic acid, about 5.7% of palmitoleic acid, about 1.4% of myristoleic acid, about 0.9% of stearic acid, about 2.1% of heptadecanoic acid, about 5% of palmitic acid, about 3.2% of myristic acid and about 0.5% of lauric acid.
Claim 8
Dependent Claim
25 words
The esters or mixtures of them as claimed in claim 2, wherein the sum of x and y averages from about 5 to about 20.
Claim 9
Dependent Claim
56 words
A mixture of esters as claimed in claim 7, wherein each of R 1 and R 2 is a mixture of the acyl groups of the fatty acids contained in one of (a) the commercial grade hydrogenated coconut oil fatty acids, (b) the commercial grade stearic acid, or (c) commercial white oil grade of oleic acid.
Claim 10
Dependent Claim
67 words
A mixture of esters as claimed in claim 8, wherein each of R 1 and R 2 is a mixture of the acyl groups contained in the commercial grade of the hydrogenated coconut oil fatty acids containing about 55% lauric acid, about 15% myristic acid, about 8% each of stearic acid and palmitic acid, about 7% caprylic acid, about 6% capric acid, and about 1% oleic acid.
Claim 11
Dependent Claim
21 words
A mixture of esters claimed in claim 9, wherein the sum of x and y averages from about 19 to 22.
Claim 12
Dependent Claim
125 words
A mixture of esters as claimed in claim 8, wherein each of R 1 and R 2 is a mixture of the acyl groups of the fatty acids of the commercial white oil grade of oleic acid, and the ester content has (a) as its major portion the two mono-esters (i) the one wherein R 2 is hydrogen and (ii) the one wherein R 1 is hydrogen, and (b) as its minor portion the di-ester having these acyl groups as each of R 1 and R 2 and, when the molar ratio of the total of the acyl groups of the mono-ester and the di-ester to that of the hydantoin moiety is less than one, then together with the correspondingly small residual unreacted starting hydantoin.
Claim 13
Dependent Claim
35 words
A mixture of esters as claimed in claim 11, wherein the sum of x and y averages from about 4 to 7, and the minor portion of the ester content consists essentially of said di-ester.
Claim 14
Dependent Claim
35 words
A mixture of esters as claimed in claim 11, wherein the sum of x and y averages from about 9 to 12, and the minor portion of the ester content consists essentially of said di-ester.
Claim 15
Dependent Claim
35 words
A mixture of esters as claimed in claim 11, wherein the sum of x and y averages from about 14 to 17, and the minor portion of the ester content consists essentially of said di-ester.
Claim 16
Dependent Claim
57 words
A mixture of esters as claimed in claim 8, wherein from about 80 to about 88.5 percent of the acyl groups R 1 and R 2 are those of the total "oleic" acids of that commercial oleic acid and the remainder of the acyl groups are those of the saturated fatty acids of that commercial oleic acid.
Claim 17
Dependent Claim
67 words
A mixture of esters as claimed in claim 15, wherein the commercial white oil grade of oleic acid consists essentially of about 72.5% of 9-cis-octadecenoic acid, about 8.6% of linoleic acid, about 5.7% of palmitoleic acid, about 1.4% of myristoleic acid, about 0.9% of stearic acid, about 2.1% of heptadecanoic acid, about 5% of palmitic acid, about 3.2% of myristic acid and about 0.5% of lauric acid.
Claim 18
Dependent Claim
35 words
A mixture of esters as claimed in claim 3, wherein each of R 1 and R 2 is a mixture of the acyl groups contained in a commercial grade of hydrogenated coconut oil fatty acids.
Claim 19
Dependent Claim
47 words
A mixture of esters as claimed in claim 17, wherein said mixture of said acyl groups contains about 55% lauric acid, about 15% myristic acid, about 8% each of stearic acid and palmitic acid, about 7% caprylic acid, about 6% capric acid, and about 1% oleic acid.
Claim 20
Dependent Claim
28 words
A mixture of esters as claimed in claim 8, wherein said mixture of acyl groups is that of the fatty acids of a commercial grade of stearic acid.
Claim 21
Dependent Claim
23 words
A mixture of esters as claimed in claim 19, wherein the sum of x and y averages from about 8 to about 12.
Claim 22
Dependent Claim
19 words
A mixture of esters as claimed in claim 20, wherein the sum of x and y averages about 11.5.
Claim 23
Dependent Claim
23 words
A mixture of esters as claimed in claim 21, wherein said commercial grade of stearic acid is the so-called 70% commercial stearic acid.
Claim 24
Dependent Claim
41 words
A mixture of esters as claimed in claim 22, wherein said 70% commercial stearic acid contains about 68% of stearic acid, 2% of margaric acid, 26.5% of palmitic acid, 0.5% pentadecanoic acid, 2% of myristic acid, and 1% of oleic acid.
Claim 25
Dependent Claim
51 words
A mixture of esters as claimed in claim 4, wherein said acyl groups are those of the fatty acids of a commercial white oil grade of oleic acid and the molar ratio of the total of the acyl groups to that of the ethoxylated hydantoin moiety is about 2 to 1.
Claim 26
Dependent Claim
33 words
A mixture of esters as claimed in claim 24, wherein from about 80 to about 88.5 percent of said acyl groups are those of the total "oleic" acids of said commercial oleic acid.
Claim 27
Dependent Claim
44 words
A mixture of esters as claimed in claim 11, wherein the molar ratio of the total of the acyl groups to that of the ethoxylated hydantoin moiety is from about 1 to about 2 moles of acyl groups per mol of said hydantoin moiety.
Claim 28
Dependent Claim
22 words
A mixture of esters as claimed in claim 26, wherein the sum of x and y averages from about 4 to 7.
Claim 29
Dependent Claim
19 words
A mixture of esters as claimed in claim 27, wherein the sum of x and y averages about 6.6.
Claim 30
Dependent Claim
22 words
A mixture of esters as claimed in claim 26, wherein the sum of x and y averages from about 9 to 19.
Claim 31
Dependent Claim
19 words
A mixture of esters as claimed in claim 29, wherein the sum of x and y averages about 11.8.
Claim 32
Dependent Claim
22 words
A mixture of esters as claimed in claim 26, wherein the sum of x and y averages from about 14 to 17.
Claim 33
Dependent Claim
19 words
A mixture of esters as claimed in claim 31, wherein the sum of x and y averages about 16.2.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-06 | 1980-12-06 | 1981-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-06 | 1984-12-06 | 1985-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-06 | 1988-12-06 | 1989-06-07 | $7700.00 | Window Closed / Lapsed |