US3929847A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Ether diester derivatives of p-dioxanone
Assignee: Eastman Kodak Co
•
Filing: 1974-09-25
•
Granted: 1975-12-30
•
Expires: 1994-09-25
Abstract
Abstract This invention relates to a new series of ether-diester derivatives of p-dioxanone having the formula wherein R'' is alkyl of from 1 to 7 carbon atoms or the phenyl moiety and R is alkyl of from 1 to 8 carbon atoms. These novel compounds are produced by reacting p-dioxanone with an aliphatic alcohol having from 1 to 8 carbon atoms and esterifying the reaction product with an aliphatic carboxylic acid having from 2 to 8 carbon atoms or a corresponding acid anhydride. Benzoic acid or its anhydride yields the phenyl moiety in the ether-diester derivatives. The ether-diesters are particularly useful as plasticizers for polyvinyl chloride.
Inventors
- 👤 Jr Thomas C Snapp
- 👤 Alden E Blood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:40
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/10; C08K5/101; C08K5/11
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
5 words
A COMPOUND HAVING THE FORMULA
Claim 2
Dependent Claim
5 words
A COMPOUND HAVING THE FORMULA
Claim 3
Dependent Claim
13 words
The ether-diester in claim 1 wherein R is CH3 and R'' is -C4H9.
Claim 4
Dependent Claim
12 words
The ether-diester in claim 1 wherein both R and R'' are -C4H9.
Claim 5
Dependent Claim
13 words
The ether-diester in claim 1 wherein R is -C4H9 and R'' is -C7H15.
Claim 6
Dependent Claim
13 words
The ether-diester in claim 1 wherein R is C8H17 and R'' is C7H15.
Claim 7
Dependent Claim
13 words
The ether-diester in claim 1 wherein R is -C4H9 and R'' is phenyl.
Claim 8
Dependent Claim
10 words
A process for the production of ether-diesters having the formula
Claim 9
Dependent Claim
10 words
A process for the production of ether-diesters having the formula
Claim 10
Dependent Claim
30 words
A process according to claim 7 wherein the alcohol is selected from the group consisting of methanol, ethanol, propanol, n-butanol, isobutanol, 2-methylpentanol-1, n-hexanol, 2-ethylhexanol-1, n-octanol, allyl alcohol, and crotonyl alcohol.
Claim 11
Dependent Claim
22 words
A process according to claim 7 wherein the reaction of the p-dioxanone and alcohol is conducted in the presence of a catalyst.
Claim 12
Dependent Claim
33 words
A reaction according to claim 9 wherein the acid or base catalyst is selected from the group consisting of sulfuric acid, p-toluenesulfonic, organotin compounds, alkali metal hydroxides, pyridine, aliphatic tertiary amines, or N,N-dialkylanilines.
Claim 13
Dependent Claim
31 words
A reaction according to claim 9 wherein the catalyst is present in a concentration of from about 0.01 percent to about 2.0 percent based upon the total weight of the reactant.
Claim 14
Dependent Claim
23 words
A process according to claim 7 wherein the reaction of p-dioxanone and alcohol is conducted at a temperature from about 50*C. to 150*C.
Claim 15
Dependent Claim
22 words
A process according to claim 7 wherein the mole ratio of alcohol to p-dioxanone is from about 1:1 to about 15:1, respectively.
Claim 16
Dependent Claim
22 words
A process according to claim 13 wherein the mole ratio of alcohol to p-dioxanone is from about 2:1 to about 7:1, respectively.
Claim 17
Dependent Claim
31 words
A process according to claim 7 wherein the esterification reaction is conducted with a carboxylic acid selected from the group consisting of acetic, butyric, 2-methylpentanoic, hexanoic, 2-ethylhexanoic, octanoic, and benzoic acid.
Claim 18
Dependent Claim
30 words
A process according to claim 15 wherein the esterification is conducted in the presence of a catalyst selected from the group consisting of methanesulfonic, toluenesulfonic, sulfuric, phosphoric, or hydrochloric acid.
Claim 19
Dependent Claim
34 words
A process according to claim 16 wherein an esterification catalyst is present in an amount of from about 0.01 weight percent to about 1.0 weight percent based upon the total weight of the reactants.
Claim 20
Dependent Claim
31 words
A process according to claim 7 wherein the esterification reaction is conducted with an acid anhydride selected from the group consisting of acetic, butyric, 2-methylpentanoic, hexanoic, 2-ethylhexanoic, octanoic and benzoic anhydride.
Claim 21
Dependent Claim
21 words
A process according to claim 18 wherein the esterification is conducted at a temperature of from about 50*C. to about 150*C.
Claim 22
Dependent Claim
22 words
A process according to claim 15 wherein the esterification reaction is conducted at a temperature of from about 75*C. to about 200*C.
Claim 23
Dependent Claim
25 words
A process according to claim 7 wherein the mole ratio of intermediate hydroxylated ester to acid moiety is from about 1:1 to about 1:3.0, respectively.
References Cited (Backward Citations)
US2962455A
Cited
US3086044A
Cited
US3565946A
Cited
US3499028A
Cited
US3689531A
Cited
US3776766A
Cited
US3767627A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-29 | 1979-06-30 | 1979-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-29 | 1983-06-30 | 1983-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-29 | 1987-06-30 | 1987-12-30 | $7700.00 | Window Closed / Lapsed |