DE967963C - Verfahren zur Herstellung von Mischpolymeren aus Styrol und trocknenden OElen - Google Patents
Verfahren zur Herstellung von Mischpolymeren aus Styrol und trocknenden OElenInfo
- Publication number
- DE967963C DE967963C DEN5430A DEN0005430A DE967963C DE 967963 C DE967963 C DE 967963C DE N5430 A DEN5430 A DE N5430A DE N0005430 A DEN0005430 A DE N0005430A DE 967963 C DE967963 C DE 967963C
- Authority
- DE
- Germany
- Prior art keywords
- styrene
- clear
- oil
- same
- linseed oil
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 167
- 239000003921 oil Substances 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 12
- 229920001577 copolymer Polymers 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000001035 drying Methods 0.000 title description 8
- 235000019198 oils Nutrition 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 41
- 239000003054 catalyst Substances 0.000 claims description 37
- 239000000944 linseed oil Substances 0.000 claims description 30
- 235000021388 linseed oil Nutrition 0.000 claims description 30
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
- 239000011630 iodine Substances 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000003973 paint Substances 0.000 claims description 11
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 8
- 239000004922 lacquer Substances 0.000 claims description 7
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 claims description 4
- 238000010586 diagram Methods 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- ZAKVZVDDGSFVRG-UHFFFAOYSA-N prop-1-en-2-ylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C1=CC=CC=C1 ZAKVZVDDGSFVRG-UHFFFAOYSA-N 0.000 claims 1
- 239000011253 protective coating Substances 0.000 claims 1
- 239000002966 varnish Substances 0.000 description 15
- 239000004342 Benzoyl peroxide Substances 0.000 description 13
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 13
- 235000019400 benzoyl peroxide Nutrition 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- CGQJDFJVDYLLLN-UHFFFAOYSA-N [diphenyl(tritylperoxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CGQJDFJVDYLLLN-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- 229920006328 Styrofoam Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000008261 styrofoam Substances 0.000 description 3
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 2
- -1 benzoyl peroxide Chemical class 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C08F242/00—Copolymers of drying oils with other monomers
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D125/00—Coating compositions based on homopolymers or 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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL313563X | 1951-04-26 | ||
| NL2761850X | 1952-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE967963C true DE967963C (de) | 1958-01-02 |
Family
ID=32301942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN5430A Expired DE967963C (de) | 1951-04-26 | 1952-04-25 | Verfahren zur Herstellung von Mischpolymeren aus Styrol und trocknenden OElen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2761850A (en, 2012) |
| BE (2) | BE517528A (en, 2012) |
| CH (2) | CH313563A (en, 2012) |
| DE (1) | DE967963C (en, 2012) |
| FR (2) | FR1055208A (en, 2012) |
| GB (2) | GB721308A (en, 2012) |
| NL (3) | NL167360B (en, 2012) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE495577A (en, 2012) * | 1949-05-06 | |||
| US2468748A (en) * | 1944-09-26 | 1949-05-03 | Dow Chemical Co | Drying oil-styrene interpolymers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2152642A (en) * | 1939-04-04 | Treatment of teng oil | ||
| US2165530A (en) * | 1934-09-05 | 1939-07-11 | Ind Exploitatie Mij Nv | Fat-hardening process |
| FR961844A (en, 2012) * | 1942-07-28 | 1950-05-23 |
-
0
- NL NL75341D patent/NL75341C/xx active
- BE BE510979D patent/BE510979A/xx unknown
- NL NL7210366.A patent/NL160798B/xx unknown
- NL NL7009819.A patent/NL167360B/xx unknown
- BE BE517528D patent/BE517528A/xx unknown
-
1952
- 1952-04-24 GB GB10368/52A patent/GB721308A/en not_active Expired
- 1952-04-25 DE DEN5430A patent/DE967963C/de not_active Expired
- 1952-04-26 CH CH313563D patent/CH313563A/de unknown
- 1952-04-26 FR FR1055208D patent/FR1055208A/fr not_active Expired
-
1953
- 1953-01-28 US US333835A patent/US2761850A/en not_active Expired - Lifetime
- 1953-02-03 GB GB3054/53A patent/GB725951A/en not_active Expired
- 1953-02-11 CH CH322259D patent/CH322259A/de unknown
- 1953-02-11 FR FR1070783D patent/FR1070783A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468748A (en) * | 1944-09-26 | 1949-05-03 | Dow Chemical Co | Drying oil-styrene interpolymers |
| BE495577A (en, 2012) * | 1949-05-06 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL160798B (nl) | |
| NL167360B (nl) | |
| NL75341C (en, 2012) | |
| GB721308A (en) | 1955-01-05 |
| BE517528A (en, 2012) | |
| FR1070783A (fr) | 1954-08-12 |
| CH322259A (de) | 1957-06-15 |
| FR1055208A (fr) | 1954-02-17 |
| GB725951A (en) | 1955-03-16 |
| BE510979A (en, 2012) | |
| US2761850A (en) | 1956-09-04 |
| CH313563A (de) | 1956-04-30 |
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