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US4604295A Expired / Lapsed US ⏱️ 0.0 years remaining

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
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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.

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

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