GB598322A - Improvements in or relating to the stabilization of synthetic rubber latices - Google Patents
Improvements in or relating to the stabilization of synthetic rubber laticesInfo
- Publication number
- GB598322A GB598322A GB1574445A GB1574445A GB598322A GB 598322 A GB598322 A GB 598322A GB 1574445 A GB1574445 A GB 1574445A GB 1574445 A GB1574445 A GB 1574445A GB 598322 A GB598322 A GB 598322A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- styrene
- phenol
- ditertiary
- latices
- 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
- 229920000126 Latex Polymers 0.000 title abstract 7
- 229920003051 synthetic elastomer Polymers 0.000 title abstract 3
- 239000005061 synthetic rubber Substances 0.000 title abstract 3
- 238000011105 stabilization Methods 0.000 title 1
- -1 alkyl phenol Chemical compound 0.000 abstract 8
- 239000003381 stabilizer Substances 0.000 abstract 7
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical class 0.000 abstract 3
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 3
- 239000000084 colloidal system Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000000344 soap Substances 0.000 abstract 3
- 239000011780 sodium chloride Substances 0.000 abstract 3
- SASYHUDIOGGZCN-ONEGZZNKSA-L (E)-2-ethylbut-2-enedioate Chemical compound CC\C(C([O-])=O)=C/C([O-])=O SASYHUDIOGGZCN-ONEGZZNKSA-L 0.000 abstract 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 abstract 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N 2-cyanopropene-1 Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 abstract 2
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 abstract 2
- MHRFIEZKKQESCC-UHFFFAOYSA-N C(C(C)C)C=1C2(C(C=CC1)(O)S2)CC(C)C Chemical compound C(C(C)C)C=1C2(C(C=CC1)(O)S2)CC(C)C MHRFIEZKKQESCC-UHFFFAOYSA-N 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N M-Cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N Methyl vinyl ketone Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N Piperylene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 2
- SBYMUDUGTIKLCR-VOTSOKGWSA-N [(E)-2-chloroethenyl]benzene Chemical compound Cl\C=C\C1=CC=CC=C1 SBYMUDUGTIKLCR-VOTSOKGWSA-N 0.000 abstract 2
- YMOONIIMQBGTDU-SREVYHEPSA-N [(Z)-2-bromoethenyl]benzene Chemical compound Br\C=C/C1=CC=CC=C1 YMOONIIMQBGTDU-SREVYHEPSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical group CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002237 fumaric acid derivatives Chemical class 0.000 abstract 2
- 239000003292 glue Substances 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000002335 preservative Effects 0.000 abstract 2
- 239000003755 preservative agent Substances 0.000 abstract 2
- 230000001681 protective Effects 0.000 abstract 2
- 150000003440 styrenes Chemical class 0.000 abstract 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 2
- KPGABFJTMYCRHJ-YZOKENDUSA-N Ammonium alginate Chemical compound [NH4+].[NH4+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O KPGABFJTMYCRHJ-YZOKENDUSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N Benzyl mercaptan Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 abstract 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N DECANE-1-THIOL Chemical group CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 235000010407 ammonium alginate Nutrition 0.000 abstract 1
- 239000000728 ammonium alginate Substances 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 230000001804 emulsifying Effects 0.000 abstract 1
- VPIAKHNXCOTPAY-UHFFFAOYSA-N heptane-1-thiol Chemical group CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004816 latex Substances 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical group CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 abstract 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical class CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Synthetic rubber latices are stabilized by the addition of a ditertiary alkyl phenol. The preferred stabilizers are the ditertiary butyl and ditertiary amyl derivatives of o-, m- and p-cresol. The latices may be those obtained by the copolymerization in aqueous emulsion of butadiene-1,3; isoprene; piperylene; dimethyl butadiene; and methyl pentadiene; in admixture with styrene; alpha methyl styrene; para methyl styrene; alpha methyl para methyl styrene; halogenated styrenes such as chloro- or bromo-styrene; acrylonitrile; methacrylonitrile; acrylic acid and methacrylic acid esters such as methyl acrylate and methyl methacrylate; fumaric acid esters such as ethyl fumarate; and unsaturated ketones such as methyl vinyl ketone, and methyl isopropenyl ketone. The latices may be prepared by emulsifying the reactants in water in the presence of a water-soluble soap such as alkali metal or ammonium oleates, stearates or palmitates; and surface active agents such as salts of alkylated naphthalene sulphonic acids, fatty alcohol sulphates, salts of aliphatic and olefinic sulphonic acids and acid addition salts of high molecular alkyl amines; and polymerization catalysts such as benzoyl peroxide, hydrogen peroxide, and alkali metal or ammonium perborates or persulphates; and a polymerization modifier such as a dialkyl xanthogen disulphide, or an aliphatic mercaptan containing at least 7 carbon atoms in an aliphatic linkage, such as heptyl, octyl, decyl, dodecyl, lauryl or benzyl mercaptan. The stabilizer is preferably employed in the form of a dispersion obtained by grinding the phenol in the presence of a soap or aromatic sulphonate and a protective colloid such as glue with or without a preservative such as that known as "Collatone." Alternatively, the stabilizers may be dissolved in an aromatic solvent or an alcohol with at least 4 carbon atoms. Diisobutyl phenol sulphide may also be added.ALSO:Synthetic rubber latices are stabilized by the addition of a ditertiary alkyl phenol. The preferred stabilizers are the ditertiary butyl and ditertiary amyl derivatives of o-, m-, and p-cresol. The latices may be thus obtained by the polymerisation in aqueous emulsion of butadiene 1, 3; isoprene; piperylene; dimethyl butadiene; and methyl pentadiene; either singly or in admixture with styrene; alpha methyl styrene; para methyl styrene; alpha methyl para methyl styrene; halogenated styrenes such as chloro-, or bromo-styrene; acrylonitrile; methacrylonitrile; acrylic acid and methacrylic acid esters such as methyl acrylate and methyl methacrylate; fumaric acid esters such as ethyl fumarate; and unsaturated ketones such as methyl vinyl ketone, and methyl isopropenyl ketone. Up to 7 per cent., though usually from 0.1 to 2.0 per cent. of the stabilizer, is employed, preferably in the form of a dispersion obtained by grinding the phenol in a ball or colloid mill in the presence of a dispersing agent such as soap or aromatic sulphonates, and a protective colloid such as glue with or without a preservative such as that known as "Collatone." Alternatively the stabilizer may be dissolved in a solvent such as an aromatic hydrocarbon or an alcohol with at least 4 carbon atoms. Di-isobutyl phenol sulphide may also be added as an auxiliary stabilizer. The stabilized latex may be concentrated by adding ammonium chloride, warming to 60 DEG C, adjusting the pH to 9.5 and then creaming with ammonium alginate.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB598322A true GB598322A (en) | 1948-02-16 |
Family
ID=1731752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1574445A Expired GB598322A (en) | 1945-06-20 | Improvements in or relating to the stabilization of synthetic rubber latices |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB598322A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560044A (en) * | 1950-05-10 | 1951-07-10 | Firestone Tire & Rubber Co | Halo-alkylphenol stabilizers for synthetic rubber |
| GB2206120A (en) * | 1987-06-22 | 1988-12-29 | Firestone Tire & Rubber Co | Stabilization of guayule-type rubbers |
-
1945
- 1945-06-20 GB GB1574445A patent/GB598322A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2560044A (en) * | 1950-05-10 | 1951-07-10 | Firestone Tire & Rubber Co | Halo-alkylphenol stabilizers for synthetic rubber |
| GB2206120A (en) * | 1987-06-22 | 1988-12-29 | Firestone Tire & Rubber Co | Stabilization of guayule-type rubbers |
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