GB1100963A - Stabilized polyalkylene oxides and process for preparing them - Google Patents
Stabilized polyalkylene oxides and process for preparing themInfo
- Publication number
- GB1100963A GB1100963A GB16557/65A GB1655765A GB1100963A GB 1100963 A GB1100963 A GB 1100963A GB 16557/65 A GB16557/65 A GB 16557/65A GB 1655765 A GB1655765 A GB 1655765A GB 1100963 A GB1100963 A GB 1100963A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- alkyl
- epoxides
- compounds
- 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.)
- Expired
Links
- 229920000233 poly(alkylene oxides) Polymers 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 4
- 150000002924 oxiranes Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- -1 epichlorohydrin Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 abstract 1
- HKYYJZABVBDWJU-UHFFFAOYSA-N 1-(octadecyltrisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSCCCCCCCCCCCCCCCCCC HKYYJZABVBDWJU-UHFFFAOYSA-N 0.000 abstract 1
- UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 abstract 1
- RJJARELFCSRLSV-UHFFFAOYSA-N 2,5-ditert-butyl-4-(2,5-ditert-butyl-4-hydroxyphenyl)sulfanylphenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(SC=2C(=CC(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C RJJARELFCSRLSV-UHFFFAOYSA-N 0.000 abstract 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 abstract 1
- CBPMAFPTGJZUSN-UHFFFAOYSA-N 2-tert-butyl-4-[(5-tert-butyl-4-hydroxy-2-methylphenyl)methyl]-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1CC1=CC(C(C)(C)C)=C(O)C=C1C CBPMAFPTGJZUSN-UHFFFAOYSA-N 0.000 abstract 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
- 230000008961 swelling Effects 0.000 abstract 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 abstract 1
- 229960002447 thiram Drugs 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Polyalkylene oxides are stabilized by a mixture of the following compounds <FORM:1100963/C3/1> <FORM:1100963/C3/2> and (c) R4SnR5, in which K is a substituted, or unsubstituted benzene or naphthalene radical, R is a hydrogen atom or an alkyl, aryl or heterocyclic radical, R1 is an alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, A is -CH2- or -S-, R2 and R3 are alkyl radicals of 1 to 4 carbon atoms, n is 1 to 4 and R4, R5 are alkyl radicals or -(CH2)mCOOR6, in which R6 is an alkyl radical and m is 1 to 4. Suitable polyalkylene oxides are those obtained by polymerizing saturated alkylene oxides, halo-substituted epoxides, including epichlorohydrin, cycloaliphatic epoxides or epoxyethers, including glycidyl ethers, or by copolymerizing saturated epoxides with unsaturated epoxides, e.g. glycidyl acrylate. Typical examples of compound (a) have K as a benzene ring, R is methyl on the carbonyl group and hydrogen on the nitrogen, and R1 is the heptadecyl, benzthiazole, 1,2,4-triazole, benzotriazoles or imidazole radical. Typical examples of compounds (b) are bis (4 - hydroxy - 2 - methyl - 5 - t - butyl - phenyl)methane, and bis (4-hydroxy-2,5-di-t-butyl-phenyl)sulphide. Typical examples of compounds (c) are di(dodecyl)sulphide, di(octadecyl)trisulphide, and trisulphide (diacetic acid octadecyl ester). The stabilizer may be added as a solid or in a solution. The stabilized polymers may be dissolved or caused to swell, and may be cross-linked. Swelling agents or solvents include: -dimethyl formamide, tetramethylene sulphone, dioxan, methanol, benzene, and chlorinated hydrocarbons. Soots, fillers, dyes or pigments, extender oils or lubricants may also be added. The example describes the stabilization of a methanolic solution of a propylene oxide-allyl glycidyl ether copolymer, thiourea, silicic acid, zinc oxide, dipentamethylene thiuram tetrasulphide, 2-mercaptobenzothiazole, and titanium dioxide with a mixture of 2% the compounds (a) which have K as benzene, R on the carbonyl is methyl, R on the nitrogen is hydrogen, and R1 is heptadecyl or benzothiazole, 0.5% of bis(4-hydroxy-5 - t - butyl - 2 - methyl - phenyl) sulphide and 0.5% of di(octadecyl) disulphide, the percentages being based on the weight of copolymer. The resulting copolymer was spun and the filaments cross-linked.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42644A DE1210559B (en) | 1964-04-18 | 1964-04-18 | Stabilizer mixtures for homo- or copolymers of alkylene oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1100963A true GB1100963A (en) | 1968-01-31 |
Family
ID=7099185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16557/65A Expired GB1100963A (en) | 1964-04-18 | 1965-04-20 | Stabilized polyalkylene oxides and process for preparing them |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT253217B (en) |
| CH (1) | CH481969A (en) |
| DE (1) | DE1210559B (en) |
| GB (1) | GB1100963A (en) |
| NL (1) | NL6504770A (en) |
| SE (1) | SE218827C1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1101016B (en) * | 1956-07-16 | 1961-03-02 | Dr Med Marcus Diamant | Protective cover for clinical thermometer |
-
1964
- 1964-04-18 DE DEF42644A patent/DE1210559B/en active Pending
-
1965
- 1965-04-14 NL NL6504770A patent/NL6504770A/xx unknown
- 1965-04-15 CH CH532265A patent/CH481969A/en not_active IP Right Cessation
- 1965-04-15 SE SE501565A patent/SE218827C1/sl unknown
- 1965-04-16 AT AT353765A patent/AT253217B/en active
- 1965-04-20 GB GB16557/65A patent/GB1100963A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH481969A (en) | 1969-11-30 |
| NL6504770A (en) | 1965-10-19 |
| SE218827C1 (en) | 1968-02-13 |
| DE1210559B (en) | 1966-02-10 |
| AT253217B (en) | 1967-03-28 |
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