CA1044399A - Crosslinking method - Google Patents
Crosslinking methodInfo
- Publication number
- CA1044399A CA1044399A CA201,213A CA201213A CA1044399A CA 1044399 A CA1044399 A CA 1044399A CA 201213 A CA201213 A CA 201213A CA 1044399 A CA1044399 A CA 1044399A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- hydroxy
- polyaldehyde
- mercaptan
- composition
- 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
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000004132 cross linking Methods 0.000 title claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 106
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 51
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229920001744 Polyaldehyde Polymers 0.000 claims abstract description 23
- 239000000047 product Substances 0.000 claims description 28
- -1 dimethoxy formylmethyl Chemical group 0.000 claims description 21
- 238000001816 cooling Methods 0.000 claims description 20
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 claims description 15
- 229920001971 elastomer Polymers 0.000 claims description 13
- 239000005060 rubber Substances 0.000 claims description 12
- 125000003172 aldehyde group Chemical group 0.000 claims description 9
- ODRKIKHWTZCVCM-UHFFFAOYSA-N 2-[4-(4-oxaldehydoylphenyl)phenyl]-2-oxoacetaldehyde Chemical group C1=CC(C(=O)C=O)=CC=C1C1=CC=C(C(=O)C=O)C=C1 ODRKIKHWTZCVCM-UHFFFAOYSA-N 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 7
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229920006037 cross link polymer Polymers 0.000 claims description 5
- 229920001021 polysulfide Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- DTCYNRIBBFRFNN-UHFFFAOYSA-N 2-(4-oxaldehydoylphenyl)-2-oxoacetaldehyde Chemical compound O=CC(=O)C1=CC=C(C(=O)C=O)C=C1 DTCYNRIBBFRFNN-UHFFFAOYSA-N 0.000 claims description 3
- HCQDYRFOJYEGLM-UHFFFAOYSA-N 3,3-dimethyl-2,4-dioxopentanedial Chemical compound O=CC(=O)C(C)(C)C(=O)C=O HCQDYRFOJYEGLM-UHFFFAOYSA-N 0.000 claims description 3
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 238000007493 shaping process Methods 0.000 claims description 3
- 150000002334 glycols Chemical class 0.000 claims description 2
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 2
- PQINGTUBZFNZFI-UHFFFAOYSA-N 2-(3,5-dioxaldehydoylphenyl)-2-oxoacetaldehyde Chemical compound O=CC(=O)C1=CC(C(=O)C=O)=CC(C(=O)C=O)=C1 PQINGTUBZFNZFI-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 238000013329 compounding Methods 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 8
- 150000004683 dihydrates Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YSTSBXDVNKYPTR-UHFFFAOYSA-N 1-[4-(4-acetylphenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=C(C(C)=O)C=C1 YSTSBXDVNKYPTR-UHFFFAOYSA-N 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000019241 carbon black Nutrition 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000011243 crosslinked material Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- YMALVMXXWVJKRP-UHFFFAOYSA-N benzene;dihydrate Chemical compound O.O.C1=CC=CC=C1 YMALVMXXWVJKRP-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000003303 reheating Methods 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- XRBVCEFESMZSAP-UHFFFAOYSA-N 2-(3,5-dioxaldehydoylphenyl)-2-oxoacetaldehyde trihydrate Chemical compound O.O.O.C(C=O)(=O)C1=CC(=CC(=C1)C(C=O)=O)C(C=O)=O XRBVCEFESMZSAP-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- VUVRCHXWMYGACH-UHFFFAOYSA-N buta-1,3-diene;2-hydroxyethyl prop-2-enoate;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.OCCOC(=O)C=C VUVRCHXWMYGACH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- DPILEEJHBAJIGN-UHFFFAOYSA-N ethyl prop-2-enoate;2-hydroxyethyl prop-2-enoate Chemical compound CCOC(=O)C=C.OCCOC(=O)C=C DPILEEJHBAJIGN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000013038 hand mixing Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000005267 main chain polymer Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 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 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- PFGNWCAJHHSYBF-UHFFFAOYSA-N phenoxybenzene dihydrate Chemical compound O.O.C1(=CC=CC=C1)OC1=CC=CC=C1 PFGNWCAJHHSYBF-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- MWLSEHWAEUWZJL-UHFFFAOYSA-N propane;dihydrate Chemical compound O.O.CCC MWLSEHWAEUWZJL-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 238000010074 rubber mixing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940105296 zinc peroxide Drugs 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
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA201,213A CA1044399A (en) | 1974-05-30 | 1974-05-30 | Crosslinking method |
| US05/568,381 US4100137A (en) | 1974-05-30 | 1975-04-15 | Crosslinking of hydroxyl-containing polymers with polyaldehyde compounds |
| FR7515946A FR2273033B1 (cg-RX-API-DMAC7.html) | 1974-05-30 | 1975-05-22 | |
| AU81486/75A AU493156B2 (en) | 1974-05-30 | 1975-05-23 | Crosslinking method |
| GB2255175A GB1467090A (en) | 1974-05-30 | 1975-05-23 | Crosslinking method |
| SE7505955A SE403482B (sv) | 1974-05-30 | 1975-05-26 | Forfarande for tverbindning av polymerer der polymeren blandas med en polyaldehydforening |
| BE156717A BE829495A (fr) | 1974-05-30 | 1975-05-26 | Procede de retitulation de polymeres contenant des radicaux hydroxyles ou mercaptan, et compositions obtenues |
| NL7506147A NL7506147A (nl) | 1974-05-30 | 1975-05-26 | Werkwijze voor het verknopen van polymeren en gevormde voortbrengselen, die geheel of ten dele uit de aldus verknoopte polymeren bestaan. |
| IT68365/75A IT1032989B (it) | 1974-05-30 | 1975-05-27 | Procedimento per la reticolazione di polimeri particolarmente di polimeri elastomerici |
| JP50063976A JPS515346A (en) | 1974-05-30 | 1975-05-28 | Jugotaino kakyohoho |
| SU7502140006A SU578895A3 (ru) | 1974-05-30 | 1975-05-29 | Способ модификации полимера |
| DE19752524117 DE2524117A1 (de) | 1974-05-30 | 1975-05-30 | Vernetzungsverfahren |
| US05/890,507 US4197395A (en) | 1974-05-30 | 1978-03-27 | Crosslinking of mercaptan containing polymers with polyaldehyde compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA201,213A CA1044399A (en) | 1974-05-30 | 1974-05-30 | Crosslinking method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044399A true CA1044399A (en) | 1978-12-12 |
Family
ID=4100238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA201,213A Expired CA1044399A (en) | 1974-05-30 | 1974-05-30 | Crosslinking method |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4100137A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS515346A (cg-RX-API-DMAC7.html) |
| BE (1) | BE829495A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1044399A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2524117A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2273033B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1467090A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1032989B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7506147A (cg-RX-API-DMAC7.html) |
| SE (1) | SE403482B (cg-RX-API-DMAC7.html) |
| SU (1) | SU578895A3 (cg-RX-API-DMAC7.html) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4451610A (en) * | 1979-06-11 | 1984-05-29 | Premix, Inc. | Preparation of curable solid polyester resin pellets and powders |
| US4661604A (en) * | 1981-06-16 | 1987-04-28 | Trw, Inc. | Monofunctional crosslinking imidophenols |
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US4584364A (en) * | 1984-02-06 | 1986-04-22 | The Boeing Company | Phenolic-capped imide sulfone resins |
| US5506060A (en) * | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US4536559A (en) * | 1983-06-17 | 1985-08-20 | The Boeing Company | Thermally stable polyimide polysulfone compositions for composite structures |
| US5516876A (en) * | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| JPS58142901A (ja) * | 1982-02-19 | 1983-08-25 | Nippon Zeon Co Ltd | ゴムの変性方法 |
| US4547553A (en) * | 1982-07-29 | 1985-10-15 | The Boeing Company | Polybutadiene modified polyester compositions |
| US4412031A (en) * | 1983-02-18 | 1983-10-25 | Nippon Zeon Co., Ltd. | Modified rubber composition employing a compound containing a carboxyl and an aldehyde group |
| US4871475A (en) * | 1985-10-07 | 1989-10-03 | The Boeing Company | Polysulfone and polyethersulfone oligomers |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US4695606A (en) * | 1986-09-22 | 1987-09-22 | Sun Chemical Corporation | Coating binder additive |
| US4837087A (en) * | 1986-09-22 | 1989-06-06 | Sequa Chemicals Inc. | Coating binder additive |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5102954A (en) * | 1990-11-09 | 1992-04-07 | Baukema Paul R | Low formaldehyde polyacetal containing coating |
| US5155170A (en) * | 1990-11-09 | 1992-10-13 | Akzo Coatings, Inc. | Process for preparing low formaldehyde polyacetal containing coating |
| CA2085784A1 (en) * | 1992-03-27 | 1993-09-28 | Borden, Inc. | Dialdehyde modified, phenolic foundry sand core binder resins, processes for making same, and process for preparing foundry cores and molds employing same |
| DE102006030557A1 (de) * | 2006-07-03 | 2008-01-10 | Celanese Emulsions Gmbh | Verfahren zur Herstellung wässriger Vinylester-Dispersionen |
| DE102007012247A1 (de) * | 2007-03-14 | 2008-09-25 | Celanese Emulsions Gmbh | Vernetzbare Polymerdispersionen, Verfahren zu deren Herstellung und Verwendung |
| DE102007033596A1 (de) * | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Beschichtungsmittel mit hoher Bewitterungsbeständigkeit, Verfahren zu deren Herstellung und deren Verwendung |
| DE102007033595A1 (de) * | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Polyvinylesterdispersionen, Verfahren zu deren Herstellung und deren Verwendung |
| FR2950064B1 (fr) * | 2009-09-14 | 2011-10-14 | Michelin Soc Tech | Composition de caoutchouc comprenant une resine phenolique |
| EP3058024B1 (en) * | 2013-10-16 | 2021-09-15 | ARLANXEO Deutschland GmbH | Functionalized polymer composition |
| EP3114164B1 (en) * | 2014-01-12 | 2025-07-02 | King Industries, Inc. | Lower temperature cure coating compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597313A (en) * | 1968-09-23 | 1971-08-03 | American Cyanamid Co | Polyaldehyde crosslinked aliphatic alcohol resins and a process of making temporary wet strength paper and paper made therefrom |
| JPS5421312B2 (cg-RX-API-DMAC7.html) * | 1972-04-08 | 1979-07-30 |
-
1974
- 1974-05-30 CA CA201,213A patent/CA1044399A/en not_active Expired
-
1975
- 1975-04-15 US US05/568,381 patent/US4100137A/en not_active Expired - Lifetime
- 1975-05-22 FR FR7515946A patent/FR2273033B1/fr not_active Expired
- 1975-05-23 GB GB2255175A patent/GB1467090A/en not_active Expired
- 1975-05-26 BE BE156717A patent/BE829495A/xx not_active IP Right Cessation
- 1975-05-26 NL NL7506147A patent/NL7506147A/xx unknown
- 1975-05-26 SE SE7505955A patent/SE403482B/xx unknown
- 1975-05-27 IT IT68365/75A patent/IT1032989B/it active
- 1975-05-28 JP JP50063976A patent/JPS515346A/ja active Pending
- 1975-05-29 SU SU7502140006A patent/SU578895A3/ru active
- 1975-05-30 DE DE19752524117 patent/DE2524117A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE829495A (fr) | 1975-11-26 |
| GB1467090A (en) | 1977-03-16 |
| DE2524117A1 (de) | 1975-12-18 |
| NL7506147A (nl) | 1975-12-02 |
| SE7505955L (sv) | 1975-12-01 |
| SE403482B (sv) | 1978-08-21 |
| SU578895A3 (ru) | 1977-10-30 |
| JPS515346A (en) | 1976-01-17 |
| FR2273033A1 (cg-RX-API-DMAC7.html) | 1975-12-26 |
| US4100137A (en) | 1978-07-11 |
| FR2273033B1 (cg-RX-API-DMAC7.html) | 1979-03-23 |
| AU8148675A (en) | 1976-11-25 |
| IT1032989B (it) | 1979-06-20 |
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