RU2120454C1 - Адгезивная композиция - Google Patents
Адгезивная композиция Download PDFInfo
- Publication number
- RU2120454C1 RU2120454C1 RU93058138A RU93058138A RU2120454C1 RU 2120454 C1 RU2120454 C1 RU 2120454C1 RU 93058138 A RU93058138 A RU 93058138A RU 93058138 A RU93058138 A RU 93058138A RU 2120454 C1 RU2120454 C1 RU 2120454C1
- Authority
- RU
- Russia
- Prior art keywords
- polyalkadiene
- group
- composition according
- formaldehyde
- diels
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 239000000853 adhesive Substances 0.000 title claims abstract description 62
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 62
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 55
- -1 perhalogenated cyclic diene Chemical class 0.000 claims abstract description 35
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 17
- 238000005698 Diels-Alder reaction Methods 0.000 claims abstract description 16
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 15
- 239000000047 product Substances 0.000 claims abstract description 15
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000005011 phenolic resin Substances 0.000 claims abstract description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 10
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 9
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims abstract description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000011787 zinc oxide Substances 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 5
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims abstract description 4
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 claims abstract description 4
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims abstract description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 4
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940079877 pyrogallol Drugs 0.000 claims abstract description 4
- NUYUCYZVFLZIPX-UHFFFAOYSA-N 1,2,3,4,5,5-hexabromocyclopenta-1,3-diene Chemical compound BrC1=C(Br)C(Br)(Br)C(Br)=C1Br NUYUCYZVFLZIPX-UHFFFAOYSA-N 0.000 claims abstract description 3
- BDTKCOREDQRWGK-UHFFFAOYSA-N 1,2,3,4,5,5-hexafluorocyclopenta-1,3-diene Chemical compound FC1=C(F)C(F)(F)C(F)=C1F BDTKCOREDQRWGK-UHFFFAOYSA-N 0.000 claims abstract description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims abstract description 3
- UHPAQHYFAGMQFC-UHFFFAOYSA-N 5,5-dibromo-1,2,3,4-tetrachlorocyclopenta-1,3-diene Chemical compound ClC1=C(Cl)C(Br)(Br)C(Cl)=C1Cl UHPAQHYFAGMQFC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000007859 condensation product Substances 0.000 claims abstract description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 229910052714 tellurium Inorganic materials 0.000 claims abstract description 3
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims abstract description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract 3
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 claims abstract 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 2
- 150000004059 quinone derivatives Chemical class 0.000 claims abstract 2
- 239000011669 selenium Substances 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 claims description 7
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000005487 catechin Nutrition 0.000 claims description 2
- 229950001002 cianidanol Drugs 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 239000002861 polymer material Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 235000013824 polyphenols Nutrition 0.000 claims 2
- NEECIJLRKOZOFM-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,5-difluorocyclopenta-1,3-diene Chemical compound FC1(F)C(Cl)=C(Cl)C(Cl)=C1Cl NEECIJLRKOZOFM-UHFFFAOYSA-N 0.000 claims 1
- 229960004337 hydroquinone Drugs 0.000 claims 1
- 239000004071 soot Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 11
- 239000000758 substrate Substances 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000006229 carbon black Substances 0.000 abstract description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003595 mist Substances 0.000 abstract description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 238000004512 die casting Methods 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 abstract 1
- 230000001939 inductive effect Effects 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 28
- 239000005060 rubber Substances 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 21
- 239000002184 metal Substances 0.000 description 21
- 238000001746 injection moulding Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000013011 mating Effects 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
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- 238000005304 joining Methods 0.000 description 2
- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
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- SOEDEYVDCDYMMH-UHFFFAOYSA-N robinetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 SOEDEYVDCDYMMH-UHFFFAOYSA-N 0.000 description 2
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- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
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- 239000004636 vulcanized rubber Substances 0.000 description 2
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
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- 238000007259 addition reaction Methods 0.000 description 1
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- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 150000001412 amines Chemical group 0.000 description 1
- GTAOOVIZEGFIDJ-UHFFFAOYSA-N aminooxycarbamic acid Chemical compound NONC(O)=O GTAOOVIZEGFIDJ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- AHKDJQYHVWSRLT-UHFFFAOYSA-N anthragallol Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2O AHKDJQYHVWSRLT-UHFFFAOYSA-N 0.000 description 1
- KHFQPAMXJRRXJD-UHFFFAOYSA-N anthragallol Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(OC)C(OC)=C2O KHFQPAMXJRRXJD-UHFFFAOYSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J115/00—Adhesives based on rubber derivatives
- C09J115/02—Rubber derivatives containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/12—Incorporating halogen atoms into the molecule
- C08C19/18—Incorporating halogen atoms into the molecule by reaction with hydrocarbons substituted by halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/04—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/683,219 US5128403A (en) | 1991-04-10 | 1991-04-10 | High-temperature adhesive compositions |
| US683.219 | 1991-04-10 | ||
| PCT/US1992/002400 WO1992018566A1 (en) | 1991-04-10 | 1992-03-25 | High-temperature adhesive compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU93058138A RU93058138A (ru) | 1996-07-20 |
| RU2120454C1 true RU2120454C1 (ru) | 1998-10-20 |
Family
ID=24743061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93058138A RU2120454C1 (ru) | 1991-04-10 | 1992-03-25 | Адгезивная композиция |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5128403A (enExample) |
| EP (2) | EP0508650A3 (enExample) |
| JP (1) | JP2784610B2 (enExample) |
| CN (1) | CN1051105C (enExample) |
| BG (1) | BG61309B1 (enExample) |
| CA (1) | CA2107101C (enExample) |
| CZ (1) | CZ208993A3 (enExample) |
| HU (1) | HUT65893A (enExample) |
| IE (1) | IE921139A1 (enExample) |
| PL (1) | PL168234B1 (enExample) |
| RO (1) | RO112361B1 (enExample) |
| RU (1) | RU2120454C1 (enExample) |
| SK (1) | SK283624B6 (enExample) |
| TR (1) | TR26034A (enExample) |
| WO (1) | WO1992018566A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2266943C1 (ru) * | 2004-09-21 | 2005-12-27 | Открытое акционерное общество "Балаковорезинотехника" | Клеевая композиция для крепления резин к металлу при вулканизации |
| EA010268B1 (ru) * | 2007-05-21 | 2008-06-30 | Вейнгарт, Валентин Павлович | Способ изготовления термоструктурных панелей и оборудование для его осуществления |
| RU2545297C2 (ru) * | 2010-12-30 | 2015-03-27 | Зм Инновейтив Пропертиз Компани | Виниловая лента для механической и антикоррозионной защиты |
| US12473454B2 (en) | 2019-02-21 | 2025-11-18 | Henkel Ag & Co. Kgaa | Water-based extrusion primer for polyethylene |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7037385B2 (en) | 1998-01-27 | 2006-05-02 | Lord Corporation | Aqueous metal treatment composition |
| WO2001026768A2 (en) * | 1999-10-12 | 2001-04-19 | Pitts M Michael Jr | Electrostatic enhancement for membrane-separation systems |
| US6902766B1 (en) | 2000-07-27 | 2005-06-07 | Lord Corporation | Two-part aqueous metal protection treatment |
| EP1529827B1 (en) * | 2003-11-06 | 2007-12-12 | Rohm and Haas Company | Materials for bonding elastomer |
| US20060105178A1 (en) * | 2004-11-12 | 2006-05-18 | Roitman Lipa L | Materials for bonding elastomer |
| JP2008266355A (ja) * | 2007-04-16 | 2008-11-06 | Nok Corp | 加硫接着剤組成物 |
| CN102329585B (zh) * | 2010-07-12 | 2013-10-23 | 上海海鹰粘接科技有限公司 | 一种堵漏用胶料及其制备方法 |
| CN103980752B (zh) * | 2014-05-16 | 2016-03-30 | 吴江市英力达塑料包装有限公司 | 一种管道涂料及其制备方法 |
| JP2018522954A (ja) | 2015-05-01 | 2018-08-16 | ロード コーポレイション | ゴム接合用接着剤 |
| RU2637239C1 (ru) * | 2016-08-08 | 2017-12-01 | федеральное государственное унитарное предприятие "Федеральный научно-производственный центр "Прогресс" (ФГУП "ФНПЦ "Прогресс") | Клеевой подслой для крепления резин к металлу при вулканизации |
| CN111978895A (zh) * | 2020-07-31 | 2020-11-24 | 上海普力通新材料科技有限公司 | 一种单涂型金属和橡胶热硫化粘合剂及其制备方法 |
| CN112778865B (zh) * | 2020-12-31 | 2022-04-15 | 宁波普力通化学有限公司 | 一种全卤二烯烃改性聚合物防腐涂料 |
| WO2025090402A1 (en) * | 2023-10-23 | 2025-05-01 | Geisys Ventures, LLC | Debondable adhesive |
| WO2025240130A1 (en) * | 2024-05-15 | 2025-11-20 | Ddp Specialty Electronic Materials Us, Llc | Water based rubber to metal bonding agent with improved prebake resistance |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795778A (en) * | 1986-10-16 | 1989-01-03 | Bond Karen M | Adhesive halogenated cyclic conjugated diene and 1,2 polybutadiene |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258389A (en) * | 1962-08-31 | 1966-06-28 | Lord Corp | Adhesive composition for bonding rubber to metal |
| US3258388A (en) * | 1962-08-31 | 1966-06-28 | Lord Corp | Adhesive composition for bonding rubber to metal |
| LU53123A1 (enExample) * | 1966-03-08 | 1967-05-03 | ||
| US3640941A (en) * | 1970-05-08 | 1972-02-08 | Whittaker Corp | Adhesive composition |
| GB1332230A (en) * | 1971-11-12 | 1973-10-03 | Whittaker Corp | Adhesive composition |
| DE3003934C2 (de) * | 1980-02-04 | 1986-01-30 | Degussa Ag, 6000 Frankfurt | Resorcin/Füllstoff-Präparation, Verfahren zur Herstellung und Verwendung derselben |
| DE3538975C1 (de) * | 1985-11-02 | 1986-08-14 | Continental Gummi-Werke Ag, 3000 Hannover | Kautschukhaftmischung zur Direktbindung an metallischen Koerpern oder Glas |
| CA1303278C (en) * | 1986-10-16 | 1992-06-09 | Karen Marie Bond | Adhesive compositions based on diel-alder adducts |
-
1991
- 1991-04-10 US US07/683,219 patent/US5128403A/en not_active Expired - Lifetime
-
1992
- 1992-03-25 EP EP19920302572 patent/EP0508650A3/en active Pending
- 1992-03-25 CZ CS932089A patent/CZ208993A3/cs unknown
- 1992-03-25 WO PCT/US1992/002400 patent/WO1992018566A1/en not_active Ceased
- 1992-03-25 EP EP92909532A patent/EP0582623A1/en active Pending
- 1992-03-25 RO RO94-00320A patent/RO112361B1/ro unknown
- 1992-03-25 HU HU9302846A patent/HUT65893A/hu unknown
- 1992-03-25 CA CA002107101A patent/CA2107101C/en not_active Expired - Fee Related
- 1992-03-25 RU RU93058138A patent/RU2120454C1/ru active
- 1992-03-25 SK SK1089-93A patent/SK283624B6/sk unknown
- 1992-03-25 JP JP4509593A patent/JP2784610B2/ja not_active Expired - Fee Related
- 1992-03-25 PL PL92300999A patent/PL168234B1/pl unknown
- 1992-04-09 IE IE113992A patent/IE921139A1/en unknown
- 1992-04-10 TR TR92/0284A patent/TR26034A/xx unknown
- 1992-04-10 CN CN92102610A patent/CN1051105C/zh not_active Expired - Fee Related
-
1993
- 1993-11-08 BG BG98204A patent/BG61309B1/bg unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795778A (en) * | 1986-10-16 | 1989-01-03 | Bond Karen M | Adhesive halogenated cyclic conjugated diene and 1,2 polybutadiene |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2266943C1 (ru) * | 2004-09-21 | 2005-12-27 | Открытое акционерное общество "Балаковорезинотехника" | Клеевая композиция для крепления резин к металлу при вулканизации |
| EA010268B1 (ru) * | 2007-05-21 | 2008-06-30 | Вейнгарт, Валентин Павлович | Способ изготовления термоструктурных панелей и оборудование для его осуществления |
| RU2545297C2 (ru) * | 2010-12-30 | 2015-03-27 | Зм Инновейтив Пропертиз Компани | Виниловая лента для механической и антикоррозионной защиты |
| US12473454B2 (en) | 2019-02-21 | 2025-11-18 | Henkel Ag & Co. Kgaa | Water-based extrusion primer for polyethylene |
Also Published As
| Publication number | Publication date |
|---|---|
| PL168234B1 (pl) | 1996-01-31 |
| US5128403A (en) | 1992-07-07 |
| SK283624B6 (sk) | 2003-10-07 |
| BG98204A (bg) | 1995-01-31 |
| JPH06509594A (ja) | 1994-10-27 |
| HUT65893A (en) | 1994-07-28 |
| RO112361B1 (ro) | 1997-08-29 |
| CZ208993A3 (en) | 1994-03-16 |
| TR26034A (tr) | 1993-11-01 |
| CA2107101A1 (en) | 1992-10-11 |
| EP0508650A3 (en) | 1992-11-25 |
| IE921139A1 (en) | 1992-10-21 |
| WO1992018566A1 (en) | 1992-10-29 |
| CN1065672A (zh) | 1992-10-28 |
| JP2784610B2 (ja) | 1998-08-06 |
| EP0508650A2 (en) | 1992-10-14 |
| HU9302846D0 (en) | 1994-01-28 |
| CN1051105C (zh) | 2000-04-05 |
| CA2107101C (en) | 1998-09-15 |
| EP0582623A1 (en) | 1994-02-16 |
| BG61309B1 (en) | 1997-05-30 |
| SK108993A3 (en) | 1994-05-11 |
| EP0582623A4 (enExample) | 1994-04-20 |
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