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Patent · US5690856A · A · US

Solid diacyl organic peroxide dispersions

(11) Publication number
US5690856A
(21) Application number
US-40014695-A
(22) Filing date
1995-03-07
(30) Priority date
1995-03-07
(43) Publication date
1997-11-25
(45) Date of grant
1997-11-25
(52) CPC
  • C07C Acyclic or carbocyclic compounds: 407/006, 409/00
  • C08F Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds: 2/40, 4/34
(73) Assignee
AKZO NOBEL NV
(54) Title
Solid diacyl organic peroxide dispersions
(57) Abstract

The present invention generally relates to solid diacyl organic peroxide formulations in liquid or paste form having improved thermal stability. The formulations generally comprise solid diacyl organic peroxide, a dispersing plasticizer having a solid organic peroxide solubility of from about 3-10%, a phlegmatizer vehicle having minimal or no solid organic peroxide solubility, and optional ingredients such as surfactants, thixotropic agents, mixtures thereof and the like.

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Claims (26)

  1. A stabilized dispersion in paste form with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle having minimal or no solid peroxide solubility, wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of about 7.1:1 to about 12:1.
  2. The paste of claim 1 wherein said diacyl peroxide is of the general formula: ##STR2## wherein R is an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radical.
  3. The paste of claim 2 wherein said diacyl peroxide is selected from the group consisting of di-(p-chlorobenzoyl) peroxide, di-(2,4-dichlorobenzoyl) peroxide, acetyl benzoyl peroxide, lauroyl peroxide, dibenzoyl peroxide and mixtures thereof.
  4. The paste of claim 1 wherein said dispersing plasticizer is selected from the group consisting of acetate, adipate, azelate, benzoate, butyrate, citrate, fumarate, hexanoate, maleate, oleate, phthalate, phosphate, sebacate or tallate esters, alkyl benzyl phthalates and mixtures thereof.
  5. The paste of claim 4 wherein said dispersing plasticizer is selected from the group consisting of n-butyl benzoate, methylbenzoate, ethylbenzoate, hexyl benzoate, isobutyl benzoate, isodecyl benzoate, propylene glycol dibenzoate, 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, tributylethyl phosphate, tributyl phosphate, dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, butyl benzyl phthalate, dioctyl phthalate, diisooctyl phthalate, polygylcol phthalate, dibutyl phthalate, di-1-nonyl phthalate, di-isodecyl phthalate and mixtures thereof.
  6. The paste of claim 5 wherein said diacyl peroxide is selected the group consisting of di-(2,4-dichlorobenzoyl) peroxide, dibenzoyl peroxide and mixtures thereof, and said dispersing plasticizer is selected from the group consisting of 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, isodecyl benzoate, propylene glycol dibenzoate, C 7-9 alkyl benzyl phthalates, diisobutyl phthalate, butyl benzyl phthalate, alkyl benzoates mixtures thereof.
  7. The paste of claim 1 wherein said phlegmatizing vehicle is water, an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates and mixtures thereof.
  8. The paste of claim 7 wherein said phlegmatizing vehicle is selected from the group consisting of light napthenic hydrotreated distillates, C 15 n-paraffin, water and mixtures thereof.
  9. The paste of claim 1 which additionally comprises nonionic surfactants, anionic surfactants and mixtures thereof.
  10. The paste of claim 1 which additionally comprises at least one thixotropic agent.
  11. The paste of claim 1 wherein the ratio of diacyl peroxide dispersing plasticizer is from about 7.3:1 to about 11:1.
  12. The paste of claim 11 wherein the diacyl peroxide is dibenzoyl peroxide and said dispersing plasticizer is isodecyl benzoate.
  13. The paste of claim 11 which comprises 48-57% by weight dibenzoyl peroxide, 4-8% by weight isodecyl benzoate, 0-10% by weight of at least one surfactant, 0-10% by weight of at least one thixotropic agent, and 20-48% by weight of a phlegmatizing vehicle.
  14. A stabilized liquid dispersion with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle which comprises water and from about 10% to about 90% by weight of an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates or mixtures therefore, and optionally, at least one surfactant and at least one thixotropic agent, wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of 3.4:1 to 12:1.
  15. The dispersion of claim 14 wherein said diacyl peroxide is selected from the group consisting of di-(p-chlorobenzoyl) peroxide, di-2,4-dichlorobenzoyl) peroxide, acetyl benzoyl peroxide, lauroyl peroxide, dibenzoyl peroxide and mixtures thereof.
  16. The dispersion of claim 14 wherein said dispersing plasticizer is selected from the group consisting of acetate, adipate, azelate, benzoate, butyrate, citrate, fumarate, hexanoate, maleate, oleate, phthalate, phosphate, sebacate, alkyl benzyl phthalates, tallate esters and mixtures thereof.
  17. The dispersion of claim 14 wherein said diacyl peroxide is selected from the group consisting of di-(2,4-dichlorobenzoyl) peroxide, dibenzoyl peroxide and mixtures thereof, and said dispersing plasticizer is selected from the group consisting of 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, diisobutyl phthalate, butyl benzyl phthalate, isodecyl benzoate, propylene glycol dibenzoate, C 7-9 alkyl benzyl phthalates and mixtures thereof.
  18. The dispersion of claim 14 wherein said phlegmatizing vehicle is from the group consisting of light napthenic hydrotreated distillates, C 15 n-paraffin, water, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof.
  19. The dispersion of claim 14 which comprises from about 38% to 42% weight diacyl peroxide, from about 3% to about 9% by weight dispersing plasticizer, from about 29% to about 59% by weight phlegmatizing vehicle, 0-10% by weight of at least one surfactant, and 0-10% by weight of at least one thixotropic agent, wherein said phlegmatizing vehicle comprises water and from about 10% to about 90% by weight of an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater about 212° F., adipates, oleates, phthalates and mixtures thereof.
  20. The dispersion of claim 19 wherein said phlegmatizing vehicle comprises water and 10-90% by weight of aromatic or aliphatic hydrocarbons comprising light napthenic hydrotreated distillates C 15 n-paraffins and mixtures thereof.
  21. The dispersion of claim 20 wherein said diacyl peroxide is dibenzoyl peroxide, said dispersing plasticizer comprises a C 8 -C 12 alkyl benzoate ester, and said phlegmatizing vehicle comprises water and from about 10% to about 90% Jayflex® 210, Jayflex® 215 and mixtures thereof.
  22. The dispersion of claim 14 wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of about 7.1:1 to about 12:1.
  23. The dispersion of claim 22 wherein said dispersing plasticizer comprises a C 8 -C 12 alkyl benzoate ester, and said phlegmatizing vehicle is selected from the group consisting water, light napthenic hydrotreated distillates, C 15 n-paraffin, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof.
  24. The stabilized dispersion of claim 14 which comprises from about 38-52% by weight dibenzoyl peroxide; from about 2-15% by weight dispersing plasticizer which comprises isodecyl benzoate; from about 0-10% by weight of at least one surfactant, from about 0-10% by weight of at least one thixotropic agent, and from about 29-59% by weight of at least one phlegmatizing vehicle.
  25. A stabilized, non-aqueous liquid dispersion with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle having minimal or no solid peroxide solubility selected from the group consisting of aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates and mixtures thereof.
  26. The dispersion of claim 25 wherein said diacyl peroxide is dibenzoyl peroxide and said phlegmatizing vehicle is selected from the group consisting of light napthenic hydrotreated distillates C 15 n-paraffin, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof.

Citations (40)

  • BE743092A
  • DD128808A1
  • DE1618726A1
  • EP0038988A1
  • EP0133514A1
  • JPH04288368A
  • JPS61130372A
  • US2454254A
  • US3181991A
  • US3182026A
  • US3324040A
  • US3507800A
  • US3538011A
  • US3649546A
  • US3723336A
  • US3795630A
  • US3929704A
  • US4016328A
  • US4039475A
  • US4151106A
  • US4155956A
  • US4255277A
  • US4255278A
  • US4350681A
  • US4360446A
  • US4376218A
  • US4387044A
  • US4387107A
  • US4440885A
  • US4440889A
  • US4465755A
  • US4560495A
  • US4842765A
  • US4892854A
  • US4917816A
  • US5110495A
  • US5276202A
  • US5334326A
  • USRE28818E
  • WO8900173A2
Record as JSON
{
  "publication_number": "US5690856A",
  "country": "US",
  "kind": "A",
  "title": "Solid diacyl organic peroxide dispersions",
  "abstract": "The present invention generally relates to solid diacyl organic peroxide formulations in liquid or paste form having improved thermal stability. The formulations generally comprise solid diacyl organic peroxide, a dispersing plasticizer having a solid organic peroxide solubility of from about 3-10%, a phlegmatizer vehicle having minimal or no solid organic peroxide solubility, and optional ingredients such as surfactants, thixotropic agents, mixtures thereof and the like.",
  "claims": [
    "1. A stabilized dispersion in paste form with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle having minimal or no solid peroxide solubility, wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of about 7.1:1 to about 12:1.",
    "2. The paste of claim 1 wherein said diacyl peroxide is of the general formula: ##STR2## wherein R is an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radical.",
    "3. The paste of claim 2 wherein said diacyl peroxide is selected from the group consisting of di-(p-chlorobenzoyl) peroxide, di-(2,4-dichlorobenzoyl) peroxide, acetyl benzoyl peroxide, lauroyl peroxide, dibenzoyl peroxide and mixtures thereof.",
    "4. The paste of claim 1 wherein said dispersing plasticizer is selected from the group consisting of acetate, adipate, azelate, benzoate, butyrate, citrate, fumarate, hexanoate, maleate, oleate, phthalate, phosphate, sebacate or tallate esters, alkyl benzyl phthalates and mixtures thereof.",
    "5. The paste of claim 4 wherein said dispersing plasticizer is selected from the group consisting of n-butyl benzoate, methylbenzoate, ethylbenzoate, hexyl benzoate, isobutyl benzoate, isodecyl benzoate, propylene glycol dibenzoate, 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, tributylethyl phosphate, tributyl phosphate, dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, butyl benzyl phthalate, dioctyl phthalate, diisooctyl phthalate, polygylcol phthalate, dibutyl phthalate, di-1-nonyl phthalate, di-isodecyl phthalate and mixtures thereof.",
    "6. The paste of claim 5 wherein said diacyl peroxide is selected the group consisting of di-(2,4-dichlorobenzoyl) peroxide, dibenzoyl peroxide and mixtures thereof, and said dispersing plasticizer is selected from the group consisting of 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, isodecyl benzoate, propylene glycol dibenzoate, C 7-9 alkyl benzyl phthalates, diisobutyl phthalate, butyl benzyl phthalate, alkyl benzoates mixtures thereof.",
    "7. The paste of claim 1 wherein said phlegmatizing vehicle is water, an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates and mixtures thereof.",
    "8. The paste of claim 7 wherein said phlegmatizing vehicle is selected from the group consisting of light napthenic hydrotreated distillates, C 15 n-paraffin, water and mixtures thereof.",
    "9. The paste of claim 1 which additionally comprises nonionic surfactants, anionic surfactants and mixtures thereof.",
    "10. The paste of claim 1 which additionally comprises at least one thixotropic agent.",
    "11. The paste of claim 1 wherein the ratio of diacyl peroxide dispersing plasticizer is from about 7.3:1 to about 11:1.",
    "12. The paste of claim 11 wherein the diacyl peroxide is dibenzoyl peroxide and said dispersing plasticizer is isodecyl benzoate.",
    "13. The paste of claim 11 which comprises 48-57% by weight dibenzoyl peroxide, 4-8% by weight isodecyl benzoate, 0-10% by weight of at least one surfactant, 0-10% by weight of at least one thixotropic agent, and 20-48% by weight of a phlegmatizing vehicle.",
    "14. A stabilized liquid dispersion with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle which comprises water and from about 10% to about 90% by weight of an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates or mixtures therefore, and optionally, at least one surfactant and at least one thixotropic agent, wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of 3.4:1 to 12:1.",
    "15. The dispersion of claim 14 wherein said diacyl peroxide is selected from the group consisting of di-(p-chlorobenzoyl) peroxide, di-2,4-dichlorobenzoyl) peroxide, acetyl benzoyl peroxide, lauroyl peroxide, dibenzoyl peroxide and mixtures thereof.",
    "16. The dispersion of claim 14 wherein said dispersing plasticizer is selected from the group consisting of acetate, adipate, azelate, benzoate, butyrate, citrate, fumarate, hexanoate, maleate, oleate, phthalate, phosphate, sebacate, alkyl benzyl phthalates, tallate esters and mixtures thereof.",
    "17. The dispersion of claim 14 wherein said diacyl peroxide is selected from the group consisting of di-(2,4-dichlorobenzoyl) peroxide, dibenzoyl peroxide and mixtures thereof, and said dispersing plasticizer is selected from the group consisting of 2-ethylhexyl diphenyl phosphate, isodecyl diphenyl phosphate, diisobutyl phthalate, butyl benzyl phthalate, isodecyl benzoate, propylene glycol dibenzoate, C 7-9 alkyl benzyl phthalates and mixtures thereof.",
    "18. The dispersion of claim 14 wherein said phlegmatizing vehicle is from the group consisting of light napthenic hydrotreated distillates, C 15 n-paraffin, water, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof.",
    "19. The dispersion of claim 14 which comprises from about 38% to 42% weight diacyl peroxide, from about 3% to about 9% by weight dispersing plasticizer, from about 29% to about 59% by weight phlegmatizing vehicle, 0-10% by weight of at least one surfactant, and 0-10% by weight of at least one thixotropic agent, wherein said phlegmatizing vehicle comprises water and from about 10% to about 90% by weight of an aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater about 212° F., adipates, oleates, phthalates and mixtures thereof.",
    "20. The dispersion of claim 19 wherein said phlegmatizing vehicle comprises water and 10-90% by weight of aromatic or aliphatic hydrocarbons comprising light napthenic hydrotreated distillates C 15 n-paraffins and mixtures thereof.",
    "21. The dispersion of claim 20 wherein said diacyl peroxide is dibenzoyl peroxide, said dispersing plasticizer comprises a C 8 -C 12 alkyl benzoate ester, and said phlegmatizing vehicle comprises water and from about 10% to about 90% Jayflex® 210, Jayflex® 215 and mixtures thereof.",
    "22. The dispersion of claim 14 wherein the ratio of diacyl peroxide to dispersing plasticizer is in the range of about 7.1:1 to about 12:1.",
    "23. The dispersion of claim 22 wherein said dispersing plasticizer comprises a C 8 -C 12 alkyl benzoate ester, and said phlegmatizing vehicle is selected from the group consisting water, light napthenic hydrotreated distillates, C 15 n-paraffin, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof.",
    "24. The stabilized dispersion of claim 14 which comprises from about 38-52% by weight dibenzoyl peroxide; from about 2-15% by weight dispersing plasticizer which comprises isodecyl benzoate; from about 0-10% by weight of at least one surfactant, from about 0-10% by weight of at least one thixotropic agent, and from about 29-59% by weight of at least one phlegmatizing vehicle.",
    "25. A stabilized, non-aqueous liquid dispersion with increased thermal stability which comprises: (1) diacyl peroxide, (2) at least one dispersing plasticizer, and (3) at least one phlegmatizing vehicle having minimal or no solid peroxide solubility selected from the group consisting of aliphatic or aromatic hydrocarbon with a flash point of greater than about 100° F., a melting point of less than about 68° F. and a boiling point of greater than about 212° F., adipates, oleates, phthalates and mixtures thereof.",
    "26. The dispersion of claim 25 wherein said diacyl peroxide is dibenzoyl peroxide and said phlegmatizing vehicle is selected from the group consisting of light napthenic hydrotreated distillates C 15 n-paraffin, di-2-ethylhexyl azelate, dialkyl (C 7 -C 9) adipate, diisodecyl adipate, n-butyl oleate, dioctyl terephthalate and mixtures thereof."
  ],
  "cpc": [
    "C07C 407/006",
    "C07C 409/00",
    "C08F 2/40",
    "C08F 4/34"
  ],
  "assignees": [
    "AKZO NOBEL NV"
  ],
  "filing_date": "1995-03-07",
  "publication_date": "1997-11-25",
  "grant_date": "1997-11-25",
  "priority_date": "1995-03-07",
  "application_number": "US-40014695-A",
  "family_id": "23582407",
  "citations": [
    "BE743092A",
    "DD128808A1",
    "DE1618726A1",
    "EP0038988A1",
    "EP0133514A1",
    "JPH04288368A",
    "JPS61130372A",
    "US2454254A",
    "US3181991A",
    "US3182026A",
    "US3324040A",
    "US3507800A",
    "US3538011A",
    "US3649546A",
    "US3723336A",
    "US3795630A",
    "US3929704A",
    "US4016328A",
    "US4039475A",
    "US4151106A",
    "US4155956A",
    "US4255277A",
    "US4255278A",
    "US4350681A",
    "US4360446A",
    "US4376218A",
    "US4387044A",
    "US4387107A",
    "US4440885A",
    "US4440889A",
    "US4465755A",
    "US4560495A",
    "US4842765A",
    "US4892854A",
    "US4917816A",
    "US5110495A",
    "US5276202A",
    "US5334326A",
    "USRE28818E",
    "WO8900173A2"
  ]
}

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