DE2242840A1 - Multifunktionale peroxycarbonatester und verfahren zu deren herstellung - Google Patents
Multifunktionale peroxycarbonatester und verfahren zu deren herstellungInfo
- Publication number
- DE2242840A1 DE2242840A1 DE2242840A DE2242840A DE2242840A1 DE 2242840 A1 DE2242840 A1 DE 2242840A1 DE 2242840 A DE2242840 A DE 2242840A DE 2242840 A DE2242840 A DE 2242840A DE 2242840 A1 DE2242840 A1 DE 2242840A1
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- peroxycarbonate
- salt
- multifunctional
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 61
- 230000008569 process Effects 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- -1 alkyl radical Chemical class 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 47
- 229920001577 copolymer Polymers 0.000 claims description 46
- 238000006116 polymerization reaction Methods 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 33
- 150000003254 radicals Chemical group 0.000 claims description 31
- 229920005684 linear copolymer Polymers 0.000 claims description 23
- 239000012429 reaction media Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000004978 peroxycarbonates Chemical class 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 229910014033 C-OH Inorganic materials 0.000 claims description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 14
- 229910014570 C—OH Inorganic materials 0.000 claims description 14
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 11
- 230000000977 initiatory effect Effects 0.000 claims description 10
- 230000001590 oxidative effect Effects 0.000 claims description 9
- 230000001687 destabilization Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 5
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000002081 peroxide group Chemical group 0.000 claims description 5
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 4
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 229920006226 ethylene-acrylic acid Polymers 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000003999 initiator Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- ZBEBOOQVKXZARN-UHFFFAOYSA-N carbonochloridic acid;ethene Chemical compound C=C.OC(Cl)=O ZBEBOOQVKXZARN-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- DQJJMWZRDSGUJP-UHFFFAOYSA-N ethenoxyethene;furan-2,5-dione Chemical compound C=COC=C.O=C1OC(=O)C=C1 DQJJMWZRDSGUJP-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 238000010952 in-situ formation Methods 0.000 description 2
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical group [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 1
- FEIQOMCWGDNMHM-UHFFFAOYSA-N 5-phenylpenta-2,4-dienoic acid Chemical compound OC(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/10—Acylation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17711571A | 1971-09-01 | 1971-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2242840A1 true DE2242840A1 (de) | 1973-03-08 |
Family
ID=22647255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2242840A Pending DE2242840A1 (de) | 1971-09-01 | 1972-08-31 | Multifunktionale peroxycarbonatester und verfahren zu deren herstellung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4834994A (enExample) |
| BE (1) | BE788226A (enExample) |
| CA (1) | CA984403A (enExample) |
| DE (1) | DE2242840A1 (enExample) |
| FR (1) | FR2151062B1 (enExample) |
| GB (1) | GB1408413A (enExample) |
| IT (1) | IT962311B (enExample) |
| NL (1) | NL7211833A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0581449A1 (en) * | 1992-07-28 | 1994-02-02 | Nof Corporation | Organic peroxide and use thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5427229A (en) * | 1977-08-02 | 1979-03-01 | San Ando Shii Konsarutanto Kk | Method of melting deposited snow |
| JPS6272857A (ja) * | 1985-09-25 | 1987-04-03 | カルイ工業株式会社 | 屋根消雪方法 |
-
1972
- 1972-08-25 CA CA150,178A patent/CA984403A/en not_active Expired
- 1972-08-30 NL NL7211833A patent/NL7211833A/xx not_active Application Discontinuation
- 1972-08-31 BE BE788226D patent/BE788226A/xx unknown
- 1972-08-31 FR FR7231018A patent/FR2151062B1/fr not_active Expired
- 1972-08-31 DE DE2242840A patent/DE2242840A1/de active Pending
- 1972-08-31 IT IT52469/72A patent/IT962311B/it active
- 1972-08-31 GB GB4035672A patent/GB1408413A/en not_active Expired
- 1972-09-01 JP JP47087229A patent/JPS4834994A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0581449A1 (en) * | 1992-07-28 | 1994-02-02 | Nof Corporation | Organic peroxide and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| IT962311B (it) | 1973-12-20 |
| JPS4834994A (enExample) | 1973-05-23 |
| NL7211833A (enExample) | 1973-03-05 |
| CA984403A (en) | 1976-02-24 |
| FR2151062B1 (enExample) | 1976-03-12 |
| FR2151062A1 (enExample) | 1973-04-13 |
| GB1408413A (en) | 1975-10-01 |
| BE788226A (fr) | 1973-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |