GB816019A - Improvements in polymerization of alkyd resin systems - Google Patents
Improvements in polymerization of alkyd resin systemsInfo
- Publication number
- GB816019A GB816019A GB3421/57A GB342157A GB816019A GB 816019 A GB816019 A GB 816019A GB 3421/57 A GB3421/57 A GB 3421/57A GB 342157 A GB342157 A GB 342157A GB 816019 A GB816019 A GB 816019A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thioacetamide
- ketone peroxide
- methyl
- peroxide
- specified
- 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
- 238000006116 polymerization reaction Methods 0.000 title abstract 3
- 229920000180 alkyd Polymers 0.000 title 1
- -1 N-thioacetmorpholide Chemical compound 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- RGOHHVIGLIMRES-UHFFFAOYSA-N n,n-dibutylethanethioamide Chemical compound CCCCN(C(C)=S)CCCC RGOHHVIGLIMRES-UHFFFAOYSA-N 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 229920006305 unsaturated polyester Polymers 0.000 abstract 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 abstract 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 abstract 1
- OAXSBIJZTFSWRG-UHFFFAOYSA-N 2-(2-sulfanylidenepyrrolidin-1-yl)acetamide Chemical compound NC(=O)CN1CCCC1=S OAXSBIJZTFSWRG-UHFFFAOYSA-N 0.000 abstract 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- WWCPTCKAPNINCA-UHFFFAOYSA-N N-(2-cyanoethyl)pentanethioamide Chemical compound C(CCCC)(=S)NCCC#N WWCPTCKAPNINCA-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- LKNQXZAHNDFIQY-UHFFFAOYSA-N n,n-dimethylethanethioamide Chemical compound CN(C)C(C)=S LKNQXZAHNDFIQY-UHFFFAOYSA-N 0.000 abstract 1
- NXRZBVQXCLWNFY-UHFFFAOYSA-N n-(4-chlorophenyl)propanethioamide Chemical compound CCC(=S)NC1=CC=C(Cl)C=C1 NXRZBVQXCLWNFY-UHFFFAOYSA-N 0.000 abstract 1
- LYBQMHBPMXDCGC-UHFFFAOYSA-N n-(4-nitrophenyl)ethanethioamide Chemical compound CC(=S)NC1=CC=C([N+]([O-])=O)C=C1 LYBQMHBPMXDCGC-UHFFFAOYSA-N 0.000 abstract 1
- HXDOQOJZRQVNEP-UHFFFAOYSA-N n-cyclohexylethanethioamide Chemical compound CC(=S)NC1CCCCC1 HXDOQOJZRQVNEP-UHFFFAOYSA-N 0.000 abstract 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N n-hexyl methyl ketone Natural products CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 abstract 1
- DYJGTTLKCKCABS-UHFFFAOYSA-N n-hexylethanethioamide Chemical compound CCCCCCNC(C)=S DYJGTTLKCKCABS-UHFFFAOYSA-N 0.000 abstract 1
- BNLLHLUAOXAUNQ-UHFFFAOYSA-N n-methylethanethioamide Chemical compound CNC(C)=S BNLLHLUAOXAUNQ-UHFFFAOYSA-N 0.000 abstract 1
- BOQKCADLPNLYCZ-UHFFFAOYSA-N n-phenylbenzenecarbothioamide Chemical compound C=1C=CC=CC=1C(=S)NC1=CC=CC=C1 BOQKCADLPNLYCZ-UHFFFAOYSA-N 0.000 abstract 1
- MWCGLTCRJJFXKR-UHFFFAOYSA-N n-phenylethanethioamide Chemical compound CC(=S)NC1=CC=CC=C1 MWCGLTCRJJFXKR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- IHRLABACBKPYLT-UHFFFAOYSA-N prop-2-enethioamide Chemical compound NC(=S)C=C IHRLABACBKPYLT-UHFFFAOYSA-N 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Catalytic polymerization of a mixture of an unsaturated polyester and an ethylenic monomer copolymerizable therewith is effected in the presence of from 0.01 to 1 per cent by weight of a thioamide of the formula <FORM:0816019/IV (a)/1> where R is alkyl, alkenyl, aryl or substituted aryl, R1 and R2 are as for R or hydrogen, cycloalkyl or substituted alkyl, as a promoter, and, as the catalyst, a peroxide of a ketone of the formula <FORM:0816019/IV (a)/2> where R and R1 are each lower alkyl radicals having from 1 to 6 carbon atoms, or, together with the carbonyl group form a 5-6 membered carbon ring. Specified unsaturated polyesters are those prepared from polyhydric alcohols and alpha, beta-ethylenic acids with or without modifying agents. Specified ethylenic monomers are styrene, vinyl toluene, methyl methacrylate, vinyl acetate and diallyl phthalate. Specified thioamides are thiopropionamide, thiovaleramide, thiocaprylamide, thioacrylamide, N,N-dibutyl thioacetamide, N-hexyl thioacetamide, N,N-dibutyl thioacetamide, N-cyanoethyl thiovaleramide, N-thioacetmorpholide, N-cyclohexyl thioacetamide, N-p-chlorophenyl thiopropionamide and thioacet-toluidide. Catalysts specified are methyl ethyl ketone peroxide, methyl hexyl ketone peroxide, diethyl ketone peroxide, dibutyl ketone peroxide, methyl isobutyl ketone peroxide, methylamyl ketone peroxide and cyclohexanone peroxide. The examples describe the polymerization of a hydroquinone stabilized mixture of styrene and a polyester derived from phthalic anhydride, maleic anhydride and propylene glycol using catalysts and promoters selected from (1) catalysts:-methyl ethyl ketone peroxide and methyl amyl ketone peroxide; (2) promoters:-thioacetamide, thioacetanilide, N-methyl thioacetamide, N,N-dimethyl thioacetamide, p-nitro thioacetanilide, p-thioacetoaniside, N,N1-di(thioacet) - m - phenylene diamine, thiobenzamide, and thiobenzanilide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US816019XA | 1956-05-14 | 1956-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816019A true GB816019A (en) | 1959-07-08 |
Family
ID=22165178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3421/57A Expired GB816019A (en) | 1956-05-14 | 1957-01-31 | Improvements in polymerization of alkyd resin systems |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1036519B (en) |
| FR (1) | FR1172737A (en) |
| GB (1) | GB816019A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106458878B (en) * | 2014-03-18 | 2018-08-31 | 艾格埃克斯制药有限公司 | 2- cyano -3- cyclopropyl -3- hydroxy-ns-thio the acrylamide derivative of aryl - |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2466800A (en) * | 1944-04-28 | 1949-04-12 | Us Rubber Co | Oil phase polymerization of resins |
-
1957
- 1957-01-31 GB GB3421/57A patent/GB816019A/en not_active Expired
- 1957-02-18 DE DEU4375A patent/DE1036519B/en active Pending
- 1957-02-26 FR FR1172737D patent/FR1172737A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106458878B (en) * | 2014-03-18 | 2018-08-31 | 艾格埃克斯制药有限公司 | 2- cyano -3- cyclopropyl -3- hydroxy-ns-thio the acrylamide derivative of aryl - |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1172737A (en) | 1959-02-13 |
| DE1036519B (en) | 1958-08-14 |
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