DE1595708C3 - Verfahren zur Herstellung von Mischpolymerisaten des Vinylchlorids mit Nsubstituierten Maleinimiden - Google Patents
Verfahren zur Herstellung von Mischpolymerisaten des Vinylchlorids mit Nsubstituierten MaleinimidenInfo
- Publication number
- DE1595708C3 DE1595708C3 DE1595708A DE1595708A DE1595708C3 DE 1595708 C3 DE1595708 C3 DE 1595708C3 DE 1595708 A DE1595708 A DE 1595708A DE 1595708 A DE1595708 A DE 1595708A DE 1595708 C3 DE1595708 C3 DE 1595708C3
- Authority
- DE
- Germany
- Prior art keywords
- polyvinyl chloride
- copolymers
- maleimides
- softening
- vinyl chloride
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 15
- 229920001577 copolymer Polymers 0.000 title claims description 12
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 N-substituted maleimides Chemical class 0.000 title claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 11
- 239000004800 polyvinyl chloride Substances 0.000 claims description 11
- 239000011888 foil Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 241000158147 Sator Species 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 230000000717 retained effect Effects 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003490 calendering Methods 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 238000002845 discoloration Methods 0.000 claims 1
- 238000001125 extrusion Methods 0.000 claims 1
- 230000009477 glass transition Effects 0.000 claims 1
- 238000000691 measurement method Methods 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 238000009702 powder compression Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000003672 processing method Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 238000010557 suspension polymerization reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- MXVZVCCKUVRGQC-UHFFFAOYSA-N 3-hexylpyrrole-2,5-dione Chemical compound CCCCCCC1=CC(=O)NC1=O MXVZVCCKUVRGQC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- VVAKDUKOVCNCJT-UHFFFAOYSA-N dioctyltin octyl 2-sulfanylacetate Chemical compound C(CCCCCCC)OC(CS)=O.C(CCCCCCC)[Sn]CCCCCCCC VVAKDUKOVCNCJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- GXBDUKNALWQPMX-UHFFFAOYSA-N hydron;pyrrole-2,5-dione;chloride Chemical compound Cl.O=C1NC(=O)C=C1 GXBDUKNALWQPMX-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/02—Monomers containing chlorine
- C08F214/04—Monomers containing two carbon atoms
- C08F214/06—Vinyl chloride
-
- 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
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/36—Amides or imides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046995 | 1965-08-26 | ||
| ES33021766 | 1966-08-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1595708A1 DE1595708A1 (de) | 1972-03-23 |
| DE1595708B2 DE1595708B2 (de) | 1973-05-24 |
| DE1595708C3 true DE1595708C3 (de) | 1974-01-24 |
Family
ID=61628527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1595708A Expired DE1595708C3 (de) | 1965-08-26 | 1966-12-21 | Verfahren zur Herstellung von Mischpolymerisaten des Vinylchlorids mit Nsubstituierten Maleinimiden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3756991A (enExample) |
| BE (1) | BE686019A (enExample) |
| CH (1) | CH468417A (enExample) |
| DE (1) | DE1595708C3 (enExample) |
| ES (1) | ES330217A1 (enExample) |
| FR (1) | FR1490363A (enExample) |
| GB (1) | GB1105798A (enExample) |
| NL (1) | NL146846B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795565A (fr) * | 1972-02-16 | 1973-08-16 | Hoechst Ag | Agents de conservation pour dispersions aqueses, notamment pour peintures |
| US3984368A (en) * | 1975-01-23 | 1976-10-05 | Cosden Technology, Inc. | Ethylene-difunctional olefin-alkyl vinyl terpolymer emulsions |
| DE2750285A1 (de) * | 1977-11-10 | 1979-05-17 | Bayer Ag | Elektronenstrahlvernetzbare polymere |
| JPS61255915A (ja) * | 1985-05-10 | 1986-11-13 | Shin Etsu Chem Co Ltd | プラスチツク製バルブ |
| JPS61278514A (ja) * | 1985-06-04 | 1986-12-09 | Shin Etsu Chem Co Ltd | 窓枠 |
| JPS61278513A (ja) * | 1985-06-04 | 1986-12-09 | Shin Etsu Chem Co Ltd | 自動車用部材 |
| JPS61278515A (ja) * | 1985-06-04 | 1986-12-09 | Shin Etsu Chem Co Ltd | 工業用板 |
| JPS61278517A (ja) * | 1985-06-04 | 1986-12-09 | Shin Etsu Chem Co Ltd | プラスチツク製パイプ |
| US4983669A (en) * | 1988-03-07 | 1991-01-08 | Aristech Chemical Corporation | Thermosetting composition from maleimide, olefinic monomer and unsaturated polyester |
| US5089575A (en) * | 1988-09-28 | 1992-02-18 | Shin-Etsu Chemical Co., Ltd. | Method for the preparation of a copolymer of vinyl chloride and an n-substituted maleimide compound |
| EP3760611A4 (en) * | 2018-02-28 | 2021-04-21 | Mitsubishi Gas Chemical Company, Inc. | COMPOUND, RESIN, COMPOSITION AND FILM FORMING MATERIAL FOR LITHOGRAPHY USING IT |
-
1966
- 1966-08-13 ES ES0330217A patent/ES330217A1/es not_active Expired
- 1966-08-23 CH CH1217366A patent/CH468417A/de unknown
- 1966-08-25 GB GB38125/66A patent/GB1105798A/en not_active Expired
- 1966-08-25 NL NL666611986A patent/NL146846B/xx not_active IP Right Cessation
- 1966-08-26 FR FR74315A patent/FR1490363A/fr not_active Expired
- 1966-08-26 BE BE686019D patent/BE686019A/xx unknown
- 1966-12-21 DE DE1595708A patent/DE1595708C3/de not_active Expired
-
1971
- 1971-01-27 US US00110269A patent/US3756991A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1570597B2 (de) | 1972-06-22 |
| US3756991A (en) | 1973-09-04 |
| ES330217A1 (es) | 1967-06-16 |
| DE1570597A1 (de) | 1970-04-09 |
| GB1105798A (en) | 1968-03-13 |
| NL6611986A (enExample) | 1967-02-27 |
| CH468417A (de) | 1969-02-15 |
| FR1490363A (fr) | 1967-07-28 |
| BE686019A (enExample) | 1967-02-27 |
| DE1595708A1 (de) | 1972-03-23 |
| NL146846B (nl) | 1975-08-15 |
| DE1595708B2 (de) | 1973-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |