US4604295A
Expired / Lapsed
US
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Visible light absorbing peroxy-esters
Assignee: Henkel Loctite Corp
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Filing: 1983-12-22
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Granted: 1986-08-05
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Expires: 2003-12-22
Abstract
Abstract Compounds represented by the formula: <IMAGE> wherein R1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl, carboxyalkyl or carboxyaryl; R2 is any group which does not cause spontaneous decomposition of the peroxy group; and x and y are integers between 0 and 4 with x+y great than or equal to 1, are disclosed. The inventive compounds are useful as visible and UV photoinitiators and as thermal or chemical initiators for curing compositions of ethylenically unsaturated monomers and prepolymers.
Inventors
- 👤 Robert W. R. Humphreys
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 01:45
CPC Classifications
C; C08; C08F; C08F4/00; C08F4/28; C08F4/32; C08F4/36; C07; C07C; C07C409/00; C07C409/38; C07C409/40; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/18
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
52 words
A peroxy compound having the general formula: ##STR3## where R 1 is alkyl, aralkyl, alkoxalkyl, alkenyl, alkynyl or carboxyalkyl; R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x+y is greater than or equal to 1.
Claim 2
Dependent Claim
52 words
A peroxy compound having the general formula: ##STR3## where R 1 is alkyl, aralkyl, alkoxalkyl, alkenyl, alkynyl or carboxyalkyl; R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x+y is greater than or equal to 1.
Claim 3
Dependent Claim
30 words
A compound as in claim 1 where R 2 is H, alkyl, alkoxy, carboalkoxyl, silyl, nitro, alkenyl, alkynyl, halo, or when R 1 is not carboxyalkyl, amino, alkylamino or dialkylamino.
Claim 4
Dependent Claim
14 words
A compound as in claim 1 where x equals 1 and y equals 0.
Claim 5
Dependent Claim
14 words
A compound as in claim 1 wherein x equals 1 and y equals 1.
Claim 6
Dependent Claim
17 words
A compound as in claim 3 wherein the R 2 groups include at least one nitro group.
Claim 7
Dependent Claim
18 words
A compound as in claim 3 wherein the peroxy group is located in the 1,2, or 4 position.
Claim 8
Dependent Claim
11 words
A compound as in claim 1 wherein R 1 is t-butyl.
Claim 9
Dependent Claim
33 words
A compound as in claim 1 comprising a polymeric backbone having at least one group defined by the general formula of claim 1 attached thereto through an R 1 or R 2 group.
Claim 10
Dependent Claim
20 words
A compound as in claim 1 decomposable into free radicals upon exposure to light of greater than 400 nm wavelength.
Claim 11
Dependent Claim
77 words
A compound as in claim 1 selected from the t-butyl peroxy esters of: (a) fluorenone-1-carboxylic acid; (b) fluorenone-2-carboxylic acid; (c) fluorenone-4-carboxylic acid; (d) fluorenone-2,5-dicarboxylic acid; (e) fluorenone-2,7-dicarboxylic acid; (f) fluorenone-2,6-dicarboxylic acid; (g) 7-nitrofluorenone-2-carboxylic acid; (h) 7-methoxyfluorenone-2-carboxylic acid; (i) 7-acetylfluorenone-2-carboxylic acid; (j) 7-chlorofluorenone-2-carboxylic acid; (k) 7-bromofluorenone-2-carboxylic acid; (l) 7-cyanofluorenone-2-carboxylic acid; (m) 7-ethylfluorenone-2-carboxylic acid; (n) 7-butylfluorenone-2-carboxylic acid; (o) 7-butoxycarbonylfluorenone-2-carboxylic acid; (p) 7-propoxycarbonylfluorenone-2-carboxylic acid; (q) N,N-dialkyl-7-aminofluorenone-2-carboxylic acid; (r) 4,5,7-trinitrofluorenone-2-carboxylic acid; (s) 4,5-dinitrofluorenone-2,7-dicarboxylic acid; (t) 2,5,7-trinitrofluorenone-4-carboxylic acid; and (u) 7-nitrofluorenone-4-carboxylic acid.
Claim 12
Dependent Claim
67 words
In a free radical curable composition, a cure catalyst comprising a peroxy ester compound as defined by the general formula ##STR4## wherein R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl or carboxyalkyl R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1.
Claim 13
Dependent Claim
67 words
In a free radical curable composition, a cure catalyst comprising a peroxy ester compound as defined by the general formula ##STR4## wherein R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl or carboxyalkyl R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1.
Claim 14
Dependent Claim
20 words
A composition as in claim 11 where the free radical curable composition comprises at least acrylic functional monomer or prepolymer.
Claim 15
Dependent Claim
20 words
A composition as in claim 12 further comprising an activator of the decomposition of said peroxy compound into free radicals.
Claim 16
Dependent Claim
25 words
A composition as in claim 11 wherein said peroxy ester structure is linked to a polymeric backbone through an R 1 or R 2 group.
Claim 17
Dependent Claim
24 words
A composition as in claim 11 wherein said peroxy compound decomposable into free radicals upon exposure to light of greater than 400 nm wavelength.
Claim 18
Independent Claim
25 words
A method of preparing a visible light active photoinitiator comprising reacting an unsubstituted or substituted fluorenone carboxylic or dicarboxylic acid chloride with an organic hydroperoxide.
Claim 19
Independent Claim
25 words
A method of preparing a visible light active photoinitiator comprising reacting an unsubstituted or substituted fluorenone carboxylic or dicarboxylic acid chloride with an organic hydroperoxide.
Claim 20
Independent Claim
125 words
A method of providing a cured coating on a substrate having shadow areas not accessible by direct radiation, the method comprising applying a coating of a free radical curable composition to the substrate, the curable composition including: (a) a peroxy initiator of the general formula ##STR5## where R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl or carboxalkyl; R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1, and (b) a peroxide activator, exposing the substrate to UV or visible light to rapidly cure the light accessible areas and curing the light inaccessible areas by chemical activation of said peroxy initiator.
Claim 21
Independent Claim
125 words
A method of providing a cured coating on a substrate having shadow areas not accessible by direct radiation, the method comprising applying a coating of a free radical curable composition to the substrate, the curable composition including: (a) a peroxy initiator of the general formula ##STR5## where R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl or carboxalkyl; R 2 is any group which does not cause spontaneous decomposition of the peroxy group; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1, and (b) a peroxide activator, exposing the substrate to UV or visible light to rapidly cure the light accessible areas and curing the light inaccessible areas by chemical activation of said peroxy initiator.
Claim 22
Dependent Claim
16 words
A method as in claim 17 wherein said light inaccessible areas are cured at ambient temperature.
Claim 23
Independent Claim
84 words
A method of curing a free radically polymerizable formulation comprising an olefinically unsaturated compound and a compound of the formula: ##STR6## wherein R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl, carboxyalkyl, or carboxaryl; R 2 is any group which does not cause spontaneous decomposition of the peroxy groups; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1, the method comprising exposing the formulation to visible light for sufficient time to cure the formulation.
Claim 24
Independent Claim
84 words
A method of curing a free radically polymerizable formulation comprising an olefinically unsaturated compound and a compound of the formula: ##STR6## wherein R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl, carboxyalkyl, or carboxaryl; R 2 is any group which does not cause spontaneous decomposition of the peroxy groups; x and y are integers between 0 and 4 and x plus y is greater than or equal to 1, the method comprising exposing the formulation to visible light for sufficient time to cure the formulation.
Claim 25
Dependent Claim
17 words
A method as in claim 19 where R 1 is alkyl, aralkyl, alkoxyalkyl, alkenyl, alkynyl or carboxyalkyl.
Claim 26
Dependent Claim
11 words
A method as in claim 20 where R 1 is alkyl.
Claim 27
Dependent Claim
15 words
A method as in claim 19 where R 2 includes at least one nitro group.
Claim 28
Dependent Claim
15 words
A method as in claim 21 where the unsaturated compound is an acrylic functional compound.
Claim 29
Dependent Claim
12 words
A peroxy compound as in claim 1 wherein R 1 is alkyl.
References Cited (Backward Citations)
US2698863A
Cited
US3637798A
Cited
US3987088A
Cited
US4071424A
Cited
US4071424B1
Cited
US3864126A
Cited
US4110184A
Cited
US4315998A
Cited
US4013623A
Cited
US4050934A
Cited
US4131529A
Cited
US4222835A
Cited
US4457818A
Cited
US4351853A
Cited
US4416826A
Cited
US4459193A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-04 | 1990-02-03 | 1990-08-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-04 | 1994-02-03 | 1994-08-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-04 | 1998-02-03 | 1998-08-05 | $7700.00 | Window Closed / Lapsed |