US4009150A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Time-lapse free-radical polymerizable composition
Assignee: EIDP Inc
•
Filing: 1975-04-02
•
Granted: 1977-02-22
•
Expires: 1995-04-02
Abstract
Abstract A time-lapse free-radical polymerizable composition which comprises (1) a free-radical polymerizable compound such as an ethylenically unsaturated monomer or a reactive polymer; (2) a soluble polymerization initiator such as a diacyl peroxide, a ketone peroxide; an alkyl peroxy ester, a dialkyl peroxide, or an inorganic persulfate; (3) a soluble, reducible metal chelate such as an iron or copper chelate in which the chelating agent is a β-dicarbonyl compound having an enol content of at least 4 percent and a dicarbonyl angle of not greater than 120°, or a β-hydroxy nitrogen-heterocyclic fused aromatic in which the hydroxyl group is attached to a carbon beta to the nitrogen in an adjacent ring; (4) a soluble organic reducing agent which is capable of reducing ferric ions to ferrous ions or cupric ions to cuprous ions; and (5) excess chelating agent in the amount of 10 - 4 to 2.5 moles of excess chelating agent per mole of reducible metal chelate. The length of the time-lapse before onset of polymerization can be controlled by the amount of excess chelating agent present without affecting the rate of polymerization once polymerization is initiated.
Inventors
- 👤 Parry McWhinnie Norling
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:09
CPC Classifications
C; C08; C08F; C08F4/00; C08F4/40; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31855
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
66 words
A polymerization medium which comprises 1. free-radical polymerizable compound which is an ethylenically unsaturated monomers; 2. polymerization initiator soluble in the polymerization medium selected from the group consisting of a. diacyl peroxides, b. ketone peroxides, c. alkyl peroxy esters, d. dialkyl peroxides, and e. inorganic persulfates in the amount of 10.sup. -4 to 10.sup. -1 mole of polymerization initiator per mole of free radical polymerizable compound;
Claim 2
Dependent Claim
66 words
A polymerization medium which comprises 1. free-radical polymerizable compound which is an ethylenically unsaturated monomers; 2. polymerization initiator soluble in the polymerization medium selected from the group consisting of a. diacyl peroxides, b. ketone peroxides, c. alkyl peroxy esters, d. dialkyl peroxides, and e. inorganic persulfates in the amount of 10.sup. -4 to 10.sup. -1 mole of polymerization initiator per mole of free radical polymerizable compound;
Claim 3
Dependent Claim
217 words
reducible metal chelate soluble in the polymerization medium selected from the group consisting of iron and copper chelates in which the chelating agent is selected from the group consisting of a. βdicarbonyl compounds having an enol content of at least 4 percent and a dicarbonyl angle of not greater than 120° , and b. β-hydroxy nitrogen-heterocyclic fused aromatics in which the hydroxyl group is attached to a carbon beta to the nitrogen in an adjacent ring in the amount of 10.sup. -4 fo 10.sup. -1 mole of reducible metal chelate per mole of free radical polymerizable compound; 4. organic reducing agent soluble in the polymerization medium which is capable of reducing ferric ions to ferrous ions or cupric ions to cuprous ions in the amount of 10.sup. -3 to 10 3 moles of reducing agent per mole of reducible metal chelate, and 5. excess chelating agent selected from the group consisting of a. β-dicarbonyl compounds having an enol content of at least 4 percent and a dicarbonyl angle of not greater than 120° , and b. β-hydroxy nitrogen-heterocyclic fused aromatics in which the hydroxyl group is attached to a carbon beta to the nitrogen in an adjacent ring, in the amount of 10.sup. -4 to 2.5 moles of excess chelating agent per mole of reducible metal chelate.
Claim 4
Dependent Claim
217 words
reducible metal chelate soluble in the polymerization medium selected from the group consisting of iron and copper chelates in which the chelating agent is selected from the group consisting of a. βdicarbonyl compounds having an enol content of at least 4 percent and a dicarbonyl angle of not greater than 120° , and b. β-hydroxy nitrogen-heterocyclic fused aromatics in which the hydroxyl group is attached to a carbon beta to the nitrogen in an adjacent ring in the amount of 10.sup. -4 fo 10.sup. -1 mole of reducible metal chelate per mole of free radical polymerizable compound; 4. organic reducing agent soluble in the polymerization medium which is capable of reducing ferric ions to ferrous ions or cupric ions to cuprous ions in the amount of 10.sup. -3 to 10 3 moles of reducing agent per mole of reducible metal chelate, and 5. excess chelating agent selected from the group consisting of a. β-dicarbonyl compounds having an enol content of at least 4 percent and a dicarbonyl angle of not greater than 120° , and b. β-hydroxy nitrogen-heterocyclic fused aromatics in which the hydroxyl group is attached to a carbon beta to the nitrogen in an adjacent ring, in the amount of 10.sup. -4 to 2.5 moles of excess chelating agent per mole of reducible metal chelate.
Claim 5
Dependent Claim
28 words
the polymerization medium of claim 1 in which the reducible metal chelate is present in the amount of 10.sup. -3 to 10.sup. -2 mole per mole of monomer.
Claim 6
Dependent Claim
28 words
The polymerization medium of claim 2 in which the reducing agent is present in the amount of 10.sup. -2 to 10 moles per mole of reducible metal chelate.
Claim 7
Dependent Claim
28 words
The polymerization medium of claim 3 in which the polymerization initiator is present in the amount of 10.sup. -3 to 10.sup. -2 mole per mole of polymerizable compound.
Claim 8
Dependent Claim
22 words
The polymerization medium of claim 4 in which the reducible metal chelate is ferric acetylacetonate and the excess chelating agent is 2,4-pentanedione.
Claim 9
Dependent Claim
14 words
The polymerization medium of claim 1 in which the polymerization initiator is benzoyl peroxide.
Claim 10
Dependent Claim
14 words
The polymerization medium of claim 1 in which the polymerization initiator is potassium persulfate.
Claim 11
Dependent Claim
15 words
The polymerization medium of claim 6 in which the soluble organic reducing agent is benzoin.
Claim 12
Dependent Claim
15 words
The polymerization medium of claim 1 in which the polymerization initiator is tertiary butyl perbenzoate.
Claim 13
Dependent Claim
58 words
The polymerization medium of claim 1 in which free radical polymerizable compound which is an ethylenically unsaturated monomer is selected from the class consisting of olefins, vinyl esters of lower aliphatic carboxylic acids, unsaturated lower aliphatic mono- and dicarboxylic acids, alkyl esters of unsaturated lower aliphatic mono- and dicarboxylic acids, styrene, acrylonitrile, methacrylamide, acrylamide and methyl vinyl ketone.
References Cited (Backward Citations)
US2610965A
Cited
US2612490A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-22 | 1980-08-23 | 1981-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-22 | 1984-08-23 | 1985-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-22 | 1988-08-23 | 1989-02-22 | $7700.00 | Window Closed / Lapsed |