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US3963673A Expired / Lapsed US ⏱️ 0.0 years remaining

Polymer crosslinking with coupled peroxides

Assignee: Arkema Inc
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Filing: 1974-06-25
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Granted: 1976-06-15
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Expires: 1994-06-25
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Abstract

Abstract A new class of compounds: R-W-R' where R and R' are identical oxy radicals containing peroxide functions such as dialkyl or diaralkyl peroxide, proxyketal, peroxyester, or monoperoxycarbonate, and W is a carbonyl group, or carbonyl containing group, or an alkylidene or aralkylidene group, or a phosphorous containing group. Examples: Di[1,3-dimethyl-3-(t-butylperoxy)butyl]carbonate; Di[1,3-dimethyl-3-(n-butoxycarbonylperoxy)butyl]carbonate; 2,2-Bis[3,3-di(t-butylperoxy)butyoxy]propane; Di[1,3-dimethyl3-(t-butylperoxy)butyl]ethyl phosphate. They are free radical affording compounds useful in crosslinking of polyolefins and unsaturated polymers, and for the polymerization of vinyl monomers and diolefinic monomers.

Inventors

  • 👤 Antonio Joseph D'Angelo
  • 👤 Orville Leonard Mageli
  • 👤 Chester Stephen Sheppard

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 20:58
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/14; C07; C07C; C07C407/00; C07C409/00; C07C409/16; C07C409/40; C08F; C08F283/00; C08F283/01; C08F4/00; C08F4/28; C08F4/32; C08F4/38; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/86; C08K5/0008; C08K5/0025

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 364 words
In the process of crosslinking elastomers capable of being crosslinked by free radicals using as the crosslinking agent a free radical affording compound, the improvement which comprises using as said agent a peroxide of the formula R--W--R' where: a. W is selected from --C(=O)--, --C(=O)R 4 C(=O)--, --C(=O)C(=O)--, ##EQU20## b. R and R' are identical and are selected from R 3 OO--C(R 1 )(R 2 )--R 3 O--, (R 3 OO) 2 C(R 4 )--R 2 O--, R 3 OOC(=O)R 3 O--, R 3 OOC(=O)OR 3 O--, R 1 OC(=O)OO--C(R 1 )(R 2 )--R 2 O--, and R 1 C(=O)OO--C(R 1 )(R 2 )--R 2 O--; c. R 1 and R 2 are aliphatic having 1-12 carbon atoms, cycloaliphatic having 3-12 carbon atoms, or aromatic having 6-12 carbon atoms; d. R 3 is aliphatic or cycloaliphatic, each having 4-10 carbon atoms and the carbon atom joined to the peroxy oxygen atom is a tertiary carbon atom; e. R 4 is aliphatic having 1-10 carbon atoms or cycloaliphatic having 3-12 carbon atoms; f. R 5 is lower alkyl, cycloalkyl, aryl, alkoxy, cycloalkoxy, aralkoxy, or aryloxy; g. R 6 is H or lower alkyl; h. Y is the diradical O, S, or N--R 6 ; j. R 2 is an aliphatic diradical having 1-10 carbon atoms or a cycloaliphatic diradical having 3-12 carbon atoms; k. R 3 is an aliphatic diradical having 1-10 carbon atoms, cycloaliphatic diradical having 3-12 carbon atoms, aromatic diradical having 6-12 carbon atoms, or araliphatic diradical having 7-16 carbon atoms; l. R 4 is selected from R 3 , YR 3 Y, R 3 C(=O)YR 3 YC(=O)R 3 , YR 3 YC(=O)YR 3 YC(=O)YR 3 Y, YR 3 YC(=O)R 3 C(=O)YR 3 Y, YR 3 C(=O)YR 3 C(=O)YR 3 Y, YR 3 C(=O)YR 3 YC(=O)R 3 Y, YR 3 YC(=O)YR 3 Y, YR 3 YC(=O)R 3 Y and YR 3 YR 3 Y; and m. R 7 and R 8 are selected from H, alkyl of 1-10 carbons and cycloalkyl of 3-12 carbons and, when R 7 is H, R 8 can also be aryl of 6-12 carbons, and R 7 and R 8 when taken together form alkylene of 2-11 carbons.
Claim 2
Dependent Claim 364 words
In the process of crosslinking elastomers capable of being crosslinked by free radicals using as the crosslinking agent a free radical affording compound, the improvement which comprises using as said agent a peroxide of the formula R--W--R' where: a. W is selected from --C(=O)--, --C(=O)R 4 C(=O)--, --C(=O)C(=O)--, ##EQU20## b. R and R' are identical and are selected from R 3 OO--C(R 1 )(R 2 )--R 3 O--, (R 3 OO) 2 C(R 4 )--R 2 O--, R 3 OOC(=O)R 3 O--, R 3 OOC(=O)OR 3 O--, R 1 OC(=O)OO--C(R 1 )(R 2 )--R 2 O--, and R 1 C(=O)OO--C(R 1 )(R 2 )--R 2 O--; c. R 1 and R 2 are aliphatic having 1-12 carbon atoms, cycloaliphatic having 3-12 carbon atoms, or aromatic having 6-12 carbon atoms; d. R 3 is aliphatic or cycloaliphatic, each having 4-10 carbon atoms and the carbon atom joined to the peroxy oxygen atom is a tertiary carbon atom; e. R 4 is aliphatic having 1-10 carbon atoms or cycloaliphatic having 3-12 carbon atoms; f. R 5 is lower alkyl, cycloalkyl, aryl, alkoxy, cycloalkoxy, aralkoxy, or aryloxy; g. R 6 is H or lower alkyl; h. Y is the diradical O, S, or N--R 6 ; j. R 2 is an aliphatic diradical having 1-10 carbon atoms or a cycloaliphatic diradical having 3-12 carbon atoms; k. R 3 is an aliphatic diradical having 1-10 carbon atoms, cycloaliphatic diradical having 3-12 carbon atoms, aromatic diradical having 6-12 carbon atoms, or araliphatic diradical having 7-16 carbon atoms; l. R 4 is selected from R 3 , YR 3 Y, R 3 C(=O)YR 3 YC(=O)R 3 , YR 3 YC(=O)YR 3 YC(=O)YR 3 Y, YR 3 YC(=O)R 3 C(=O)YR 3 Y, YR 3 C(=O)YR 3 C(=O)YR 3 Y, YR 3 C(=O)YR 3 YC(=O)R 3 Y, YR 3 YC(=O)YR 3 Y, YR 3 YC(=O)R 3 Y and YR 3 YR 3 Y; and m. R 7 and R 8 are selected from H, alkyl of 1-10 carbons and cycloalkyl of 3-12 carbons and, when R 7 is H, R 8 can also be aryl of 6-12 carbons, and R 7 and R 8 when taken together form alkylene of 2-11 carbons.
Claim 3
Dependent Claim 12 words
A process as in claim 1 wherein the elastomer is polyurethane rubber.
Claim 4
Dependent Claim 11 words
A process as in claim 2 wherein the peroxide is di(1,3-dimethyl-3-(t-butylperoxy)butyl)carbonate.
Claim 5
Dependent Claim 11 words
A process as in claim 2 wherein the peroxide is di(1,3-dimethyl-3-(t-butylperoxy)butyl)succinate.
Claim 6
Dependent Claim 13 words
A process as in claim 2 wherein the peroxide is ethylene bis(1,3-dimethyl-3-(t-butylperoxy)butyl carbonate).
Claim 7
Dependent Claim 12 words
A process as in claim 1 wherein the elastomer is ethylene-propylene rubber.
Claim 8
Dependent Claim 11 words
A process as in claim 6 wherein the peroxide is di(1,3-dimethyl-3-(t-butylperoxy)butyl)carbonate.
Claim 9
Dependent Claim 11 words
A process as in claim 6 wherein the peroxide is di(1,3-dimethyl-3-(t-butylperoxy)butyl)succinate.
Claim 10
Dependent Claim 13 words
A process as in claim 6 wherein the peroxide is ethylene bis(1,3-dimethyl-3-(t-butylperoxy)butyl carbonate).
Claim 11
Dependent Claim 12 words
A process as in claim 1 wherein the elastomer is silicone rubber.
Claim 12
Dependent Claim 11 words
A process as in claim 10 wherein the peroxide is di(1,3-dimethyl-3-(t-butylperoxy)butyl)carbonate.

References Cited (Backward Citations)

US3658914A Cited
US3681316A Cited
US3678014A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-15 1979-12-15 1980-06-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-15 1983-12-15 1984-06-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-15 1987-12-15 1988-06-15 $7700.00 Window Closed / Lapsed

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