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US4168981A Expired / Lapsed US ⏱️ 0.0 years remaining

Bis(substituted amino)sulfides as reversible inhibitor sources for photopolymerization

Assignee: EIDP Inc
•
Filing: 1977-04-14
•
Granted: 1979-09-25
•
Expires: 1997-04-14
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Abstract

Abstract Photopolymerizable coating compositions which contain an ethylenically unsaturated polymerizable compound and a radiation sensitive, free-radical generating system are thermally stabilized to inhibit polymerization at elevated temperature without affecting room temperature photopolymerization by adding to the composition a bis(substituted amino)monosulfide or bis(substituted amino)polysulfide.

Inventors

  • 👤 Dennis S. Donald
  • 👤 Peter K. Sysak

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 12:34
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/22; C07D295/26; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/118

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 185 words
A photopolymerizable coating composition containing a sufficient amount of photoactive components to effect photopolymerization of the composition, said photoactive components consisting essentially of (a) at least one normally nongaseous, ethylenically unsaturated compound capable of addition polymerization by free-radical initiated chain propagation, (b) 0.001 to 10 parts by weight, per part of ethylenically unsaturated compound, of an organic, radiation-sensitive, free-radical generating system, and (c) 0.01 to 5% by weight, based on the total composition, of bis(substituted amino) sulfide of the formula ##STR6## where x is an integer from 1 to 4 and R and R', alike or different, are hydrocarbyl radicals of 1-12 carbons which are free of ethylenic unsaturation, or R and R' are joined together to form a divalent group selected from the group consisting of saturated aliphatic hydrocarbyl chains of 3 to 10 carbons containing at least 3 backbone carbons, saturated aliphatic chains of 4 to 9 carbons having an ether oxygen not attached to the carbon alpha to the nitrogen, and saturated aliphatic chains of 4 to 9 carbons having a carbonyl oxygen not attached to the carbon alpha to the nitrogen.
Claim 2
Dependent Claim 185 words
A photopolymerizable coating composition containing a sufficient amount of photoactive components to effect photopolymerization of the composition, said photoactive components consisting essentially of (a) at least one normally nongaseous, ethylenically unsaturated compound capable of addition polymerization by free-radical initiated chain propagation, (b) 0.001 to 10 parts by weight, per part of ethylenically unsaturated compound, of an organic, radiation-sensitive, free-radical generating system, and (c) 0.01 to 5% by weight, based on the total composition, of bis(substituted amino) sulfide of the formula ##STR6## where x is an integer from 1 to 4 and R and R', alike or different, are hydrocarbyl radicals of 1-12 carbons which are free of ethylenic unsaturation, or R and R' are joined together to form a divalent group selected from the group consisting of saturated aliphatic hydrocarbyl chains of 3 to 10 carbons containing at least 3 backbone carbons, saturated aliphatic chains of 4 to 9 carbons having an ether oxygen not attached to the carbon alpha to the nitrogen, and saturated aliphatic chains of 4 to 9 carbons having a carbonyl oxygen not attached to the carbon alpha to the nitrogen.
Claim 3
Dependent Claim 13 words
The composition of claim 1 in which the sulfide is a bis(substituted amino)polysulfide.
Claim 4
Dependent Claim 24 words
The composition of claim 2 in which the free-radical generating system absorbs actinic radiation having wavelengths within the range of 200 to 800 nm.
Claim 5
Dependent Claim 23 words
The composition of claim 3 which also contains 10 to 80% by weight, based on the total solids content, of a polymeric binder.
Claim 6
Dependent Claim 22 words
The composition of claim 4 in which the ethylenically unsaturated compound is an ester of a polyol and acrylic or methacrylic acid.
Claim 7
Dependent Claim 29 words
The composition of claim 5 in which the free-radical generating system is present in the amount of 0.01 to 2 parts by weight per part of ethylenically unsaturated ester.
Claim 8
Dependent Claim 15 words
The composition of claim 6 in which the free-radical generating system is a 2,4,5-triarylimidazole dimer.
Claim 9
Dependent Claim 32 words
The composition of claim 7 in which the sulfide is a bis(substituted amino) disulfide and is present in the amount of 0.1 to 2% by weight based on the total coating composition.
Claim 10
Dependent Claim 22 words
The composition of claim 8 in which the polymeric binder is selected from the group consisting of polyacrylate esters and poly-α-alkylacrylate esters.
Claim 11
Dependent Claim 40 words
The composition of claim 9 in which the free-radical generating system has at least one component that has an active radiation absorption band with a molar extinction coefficient of at least 50 within the range of 400 to 600 nm.
Claim 12
Dependent Claim 11 words
The composition of claim 10 in which the sulfide is bis(2,2,6,6-tetramethylpiperidino)disulfide.
Claim 13
Dependent Claim 11 words
The composition of claim 10 in which the sulfide is bis(dicyclohexylamino)disulfide.
Claim 14
Dependent Claim 11 words
The composition of claim 10 in which the sulfide is bis(diphenylamino)disulfide.
Claim 15
Dependent Claim 11 words
The composition of claim 10 in which the sulfide is bis(piperidino)disulfide.
Claim 16
Dependent Claim 11 words
The composition of claim 10 in which the sulfide is bis(morpholino)disulfide.
Claim 17
Dependent Claim 11 words
The composition of claim 7 in which the sulfide is bis(piperidino)trisulfide.
Claim 18
Dependent Claim 11 words
The composition of claim 7 in which the sulfide is bis(4-oxo-2,2,6,6-tetramethylpiperidino)tetrasulfide.

References Cited (Backward Citations)

BE809915A Cited
US3847771A Cited
US3901705A Cited
US3900379A Cited
US3885964A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-09-24 1983-03-26 1983-09-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-09-24 1987-03-26 1987-09-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-09-24 1991-03-26 1991-09-25 $7700.00 Window Closed / Lapsed

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