CA2404121C - Pyrimidine derivatives as hardness stabilizers - Google Patents
Pyrimidine derivatives as hardness stabilizers Download PDFInfo
- Publication number
- CA2404121C CA2404121C CA002404121A CA2404121A CA2404121C CA 2404121 C CA2404121 C CA 2404121C CA 002404121 A CA002404121 A CA 002404121A CA 2404121 A CA2404121 A CA 2404121A CA 2404121 C CA2404121 C CA 2404121C
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- CA
- Canada
- Prior art keywords
- composition
- phr
- rubber
- agent
- group
- 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 - Fee Related
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- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 26
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 7
- 239000003381 stabilizer Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims abstract description 80
- 229920001971 elastomer Polymers 0.000 claims abstract description 60
- 239000005060 rubber Substances 0.000 claims abstract description 59
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- 238000004073 vulcanization Methods 0.000 claims abstract description 40
- 230000006641 stabilisation Effects 0.000 claims abstract description 37
- 238000011105 stabilization Methods 0.000 claims abstract description 37
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000011593 sulfur Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- AQHBWWRHIPVRBT-UHFFFAOYSA-N s-(1,3-thiazol-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CS1 AQHBWWRHIPVRBT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000000470 constituent Substances 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 14
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 claims description 6
- WITDFSFZHZYQHB-UHFFFAOYSA-N dibenzylcarbamothioylsulfanyl n,n-dibenzylcarbamodithioate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=S)SSC(=S)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WITDFSFZHZYQHB-UHFFFAOYSA-N 0.000 claims description 6
- -1 2-benzothiazolyl Chemical group 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LNKLKFJAYIFKRJ-UHFFFAOYSA-N n-(4,6-dimethylpyrimidin-2-yl)sulfanylcyclohexanamine Chemical compound CC1=CC(C)=NC(SNC2CCCCC2)=N1 LNKLKFJAYIFKRJ-UHFFFAOYSA-N 0.000 claims description 4
- RJDBTOSSFOEORB-UHFFFAOYSA-N s-pyrimidin-2-ylthiohydroxylamine Chemical compound NSC1=NC=CC=N1 RJDBTOSSFOEORB-UHFFFAOYSA-N 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 claims description 2
- LCTFBIYMAQKHDI-UHFFFAOYSA-N 2-[(4,6-dimethylpyrimidin-2-yl)disulfanyl]-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(SSC=2N=C(C)C=C(C)N=2)=N1 LCTFBIYMAQKHDI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000012990 dithiocarbamate Substances 0.000 claims description 2
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000012991 xanthate Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003579 thiophosphoric acid derivatives Chemical class 0.000 claims 1
- 244000043261 Hevea brasiliensis Species 0.000 abstract description 16
- 229920003052 natural elastomer Polymers 0.000 abstract description 16
- 229920001194 natural rubber Polymers 0.000 abstract description 16
- 229920003048 styrene butadiene rubber Polymers 0.000 description 15
- 239000002174 Styrene-butadiene Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000004594 Masterbatch (MB) Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 3
- 229920003244 diene elastomer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CPYRTJSGQXZFEL-UHFFFAOYSA-N 4,6-dimethyl-2-(4-methylphenyl)sulfonylsulfanylpyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)SC1=NC(C)=CC(C)=N1 CPYRTJSGQXZFEL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000003679 aging effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000010059 sulfur vulcanization Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012936 vulcanization activator Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- REAIQQYMBVQGRM-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)sulfanylphthalazine Chemical compound CC1=CC(C)=NC(SC=2C3=CC=CC=C3C=NN=2)=N1 REAIQQYMBVQGRM-UHFFFAOYSA-N 0.000 description 1
- LGBYJXBCVZKJBL-UHFFFAOYSA-N 1-[(2-oxoazepan-1-yl)disulfanyl]azepan-2-one Chemical compound O=C1CCCCCN1SSN1C(=O)CCCCC1 LGBYJXBCVZKJBL-UHFFFAOYSA-N 0.000 description 1
- UQAZNERBRJNJEJ-UHFFFAOYSA-N 1-oxido-2-(pyridin-2-yldisulfanyl)pyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1SSC1=CC=CC=N1 UQAZNERBRJNJEJ-UHFFFAOYSA-N 0.000 description 1
- OFSZHKPAHQEJNP-UHFFFAOYSA-N 1-pyrimidin-2-ylsulfanylphthalazine Chemical class N=1N=CC2=CC=CC=C2C=1SC1=NC=CC=N1 OFSZHKPAHQEJNP-UHFFFAOYSA-N 0.000 description 1
- HKAVADYDPYUPRD-UHFFFAOYSA-N 1h-pyrazine-2-thione Chemical compound SC1=CN=CC=N1 HKAVADYDPYUPRD-UHFFFAOYSA-N 0.000 description 1
- PFXGHLAKCNMIEH-UHFFFAOYSA-N 2-[(4,6-dimethylpyrimidin-2-yl)disulfanyl]-1,3-benzothiazole Chemical compound CC1=CC(C)=NC(SSC=2SC3=CC=CC=C3N=2)=N1 PFXGHLAKCNMIEH-UHFFFAOYSA-N 0.000 description 1
- IPLXLVVPMIIYER-UHFFFAOYSA-N 2-[2-[[2-(1,3-benzothiazol-2-yl)-4,6-dimethyl-1h-pyrimidin-2-yl]disulfanyl]-4,6-dimethyl-1h-pyrimidin-2-yl]-1,3-benzothiazole Chemical compound N1C(C)=CC(C)=NC1(C=1SC2=CC=CC=C2N=1)SSC1(C=2SC3=CC=CC=C3N=2)N=C(C)C=C(C)N1 IPLXLVVPMIIYER-UHFFFAOYSA-N 0.000 description 1
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 description 1
- RAFAYWADRVMWFA-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidine-2-thione Chemical compound CC1=CC(C)=NC(S)=N1 RAFAYWADRVMWFA-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- 241000985973 Castilla ulei Species 0.000 description 1
- 102100024452 DNA-directed RNA polymerase III subunit RPC1 Human genes 0.000 description 1
- 241000893313 Helochara delta Species 0.000 description 1
- 101000689002 Homo sapiens DNA-directed RNA polymerase III subunit RPC1 Proteins 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- SSBBQNOCGGHKJQ-UHFFFAOYSA-N hydroxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound CC1=CC=C(S(S)(=O)=O)C=C1 SSBBQNOCGGHKJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PQZZBHDMFFSDSR-UHFFFAOYSA-N n-cyclohexyl-n-(4,6-dimethylpyrimidin-2-yl)sulfanylcyclohexanamine Chemical compound CC1=CC(C)=NC(SN(C2CCCCC2)C2CCCCC2)=N1 PQZZBHDMFFSDSR-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/44—Sulfenamides
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
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)
- Plural Heterocyclic Compounds (AREA)
- Wire Bonding (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19105400P | 2000-03-21 | 2000-03-21 | |
| US60/191,054 | 2000-03-21 | ||
| PCT/US2001/009156 WO2001070870A2 (en) | 2000-03-21 | 2001-03-21 | Pyrimidine derivatives as hardness stabilizers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2404121A1 CA2404121A1 (en) | 2001-09-27 |
| CA2404121C true CA2404121C (en) | 2009-10-06 |
Family
ID=22703945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002404121A Expired - Fee Related CA2404121C (en) | 2000-03-21 | 2001-03-21 | Pyrimidine derivatives as hardness stabilizers |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6646029B1 (enExample) |
| EP (1) | EP1319039B1 (enExample) |
| JP (1) | JP2004500471A (enExample) |
| KR (1) | KR100706415B1 (enExample) |
| CN (1) | CN1215110C (enExample) |
| AT (1) | ATE328033T1 (enExample) |
| AU (1) | AU2001245931A1 (enExample) |
| BR (1) | BR0109388A (enExample) |
| CA (1) | CA2404121C (enExample) |
| DE (1) | DE60120200T2 (enExample) |
| ES (1) | ES2266180T3 (enExample) |
| MX (1) | MXPA02009259A (enExample) |
| RU (1) | RU2265626C2 (enExample) |
| WO (1) | WO2001070870A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003070820A1 (en) * | 2002-02-22 | 2003-08-28 | Flexsys B.V. | Steel cord adhesion promoting accelerators |
| JP5905112B2 (ja) | 2011-10-24 | 2016-04-20 | ブリヂストン アメリカズ タイヤ オペレイションズ エルエルシー | シリカ充填ゴム組成物およびその製造方法 |
| JP7023812B2 (ja) * | 2017-09-14 | 2022-02-22 | 住友化学株式会社 | ゴム組成物 |
| WO2019054290A1 (ja) | 2017-09-14 | 2019-03-21 | 住友化学株式会社 | ゴム組成物 |
| WO2019102747A1 (ja) * | 2017-11-24 | 2019-05-31 | Nok株式会社 | ゴム積層金属用ｎｂｒ組成物 |
| JP6972995B2 (ja) * | 2017-12-06 | 2021-11-24 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| JP6969336B2 (ja) * | 2017-12-06 | 2021-11-24 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| US20220119623A1 (en) * | 2019-02-27 | 2022-04-21 | Sumitomo Chemical Company, Limited | Vulcanized rubber composition |
| WO2020246527A1 (ja) * | 2019-06-07 | 2020-12-10 | 住友化学株式会社 | トリスルフィド化合物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574213A (en) * | 1965-12-13 | 1971-04-06 | Monsanto Co | 4,6-di(lower alkyl) pyrimidin-2-yl phthalazine |
| US3565894A (en) * | 1967-05-15 | 1971-02-23 | Monsanto Co | Pyrimidinyl esters of dithiocarbamic acids |
| US3839303A (en) * | 1971-01-18 | 1974-10-01 | Monsanto Co | Inhibiting premature vulcanization with aminothiopyrimidines |
| JPS544379B1 (enExample) * | 1971-01-18 | 1979-03-06 | ||
| JPS4713909A (enExample) * | 1971-12-03 | 1972-07-06 | ||
| US4085093A (en) * | 1976-07-23 | 1978-04-18 | The Goodyear Tire & Rubber Company | Sulfilimines as premature vulcanization inhibitors |
| US4482663A (en) | 1982-07-12 | 1984-11-13 | Phillips Petroleum Company | Rubber compositions comprising a siliceous filler in combination with an organosulfur substituted pyridine promotor |
| US4906706A (en) | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
| US5068271A (en) * | 1988-09-21 | 1991-11-26 | Uniroyal Chemical Company, Inc. | Arylenediamine substituted pyrimidines compositions |
| US4946956A (en) * | 1988-09-21 | 1990-08-07 | Uniroyal Chemical Company, Inc. | Arylenediamine substituted pyrimidines |
| US5079305A (en) * | 1989-09-05 | 1992-01-07 | Monsanto Company | Rubber compositions comprising sulfenimide accelerators |
| DE59008849D1 (de) * | 1989-12-13 | 1995-05-11 | Huels Chemische Werke Ag | Reifenseitenwände mit erhöhter Stabilität und Verfahren zu ihrer Herstellung. |
| JPH06234880A (ja) * | 1993-02-09 | 1994-08-23 | Takashi Watanabe | ゴム用素練促進剤 |
| JPH0912782A (ja) * | 1995-06-30 | 1997-01-14 | Bridgestone Corp | 低発熱性ゴム組成物 |
| DE19641154A1 (de) | 1996-10-07 | 1998-04-16 | Bayer Ag | Polymercompounds und ihre Verwendung für die Vulkanisation halogenierter Butylkautschuke mit geringem Halogengehalt |
| WO2001016226A1 (en) * | 1999-08-31 | 2001-03-08 | Flexsys B.V. | Hardness stabilization by mercaptopyridines |
| US6465604B2 (en) * | 2000-03-21 | 2002-10-15 | Flexsys America L.P. | Pyrimidine derivatives as hardness stabilizers |
-
2001
- 2001-03-21 DE DE60120200T patent/DE60120200T2/de not_active Expired - Fee Related
- 2001-03-21 EP EP01918913A patent/EP1319039B1/en not_active Expired - Lifetime
- 2001-03-21 AT AT01918913T patent/ATE328033T1/de not_active IP Right Cessation
- 2001-03-21 CA CA002404121A patent/CA2404121C/en not_active Expired - Fee Related
- 2001-03-21 US US09/814,342 patent/US6646029B1/en not_active Expired - Fee Related
- 2001-03-21 MX MXPA02009259A patent/MXPA02009259A/es active IP Right Grant
- 2001-03-21 AU AU2001245931A patent/AU2001245931A1/en not_active Abandoned
- 2001-03-21 ES ES01918913T patent/ES2266180T3/es not_active Expired - Lifetime
- 2001-03-21 KR KR1020027012399A patent/KR100706415B1/ko not_active Expired - Fee Related
- 2001-03-21 WO PCT/US2001/009156 patent/WO2001070870A2/en not_active Ceased
- 2001-03-21 CN CNB018069541A patent/CN1215110C/zh not_active Expired - Fee Related
- 2001-03-21 RU RU2002128008/04A patent/RU2265626C2/ru active
- 2001-03-21 JP JP2001569061A patent/JP2004500471A/ja active Pending
- 2001-03-21 BR BR0109388-6A patent/BR0109388A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1319039B1 (en) | 2006-05-31 |
| WO2001070870A3 (en) | 2002-01-03 |
| AU2001245931A1 (en) | 2001-10-03 |
| CN1215110C (zh) | 2005-08-17 |
| RU2265626C2 (ru) | 2005-12-10 |
| MXPA02009259A (es) | 2003-03-12 |
| KR100706415B1 (ko) | 2007-04-10 |
| JP2004500471A (ja) | 2004-01-08 |
| US6646029B1 (en) | 2003-11-11 |
| EP1319039A2 (en) | 2003-06-18 |
| WO2001070870A2 (en) | 2001-09-27 |
| CA2404121A1 (en) | 2001-09-27 |
| KR20020084227A (ko) | 2002-11-04 |
| ATE328033T1 (de) | 2006-06-15 |
| ES2266180T3 (es) | 2007-03-01 |
| CN1420908A (zh) | 2003-05-28 |
| DE60120200D1 (de) | 2006-07-06 |
| DE60120200T2 (de) | 2007-04-12 |
| BR0109388A (pt) | 2004-07-06 |
| RU2002128008A (ru) | 2004-03-10 |
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