CA1055643A - Systeme augmentant les caracteristiques adhesives a base du produit de reaction de l'oxirane et de derives alkylphenol de novolac - Google Patents

Systeme augmentant les caracteristiques adhesives a base du produit de reaction de l'oxirane et de derives alkylphenol de novolac

Info

Publication number: CA1055643A
Authority: CA; Canada
Prior art keywords: admixture; resin; alkyl; composition; oxirane
Prior art date: 1975-01-28
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

Application number

CA228,372A

Other languages

English (en)

Other versions

CA228372S (en

Inventor

Thomas M. Galkiewicz

Kenneth C. Petersen

John L. Sullivan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SI Group Inc

Original Assignee

Schenectady Chemicals Inc

Priority date (The priority date 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 date listed.)

1975-01-28

Filing date

1975-06-03

Publication date

1979-05-29

1975-01-28 Priority claimed from US05/544,772 external-priority patent/US4073776A/en

1975-06-03 Application filed by Schenectady Chemicals Inc filed Critical Schenectady Chemicals Inc

1979-05-29 Application granted granted Critical

1979-05-29 Publication of CA1055643A publication Critical patent/CA1055643A/fr

Status Expired legal-status Critical Current

Links

229920003986 novolac Polymers 0.000 title claims abstract description 37
239000007795 chemical reaction product Substances 0.000 title claims abstract description 19
-1 alkyl phenol Chemical compound 0.000 claims abstract description 68
229920001971 elastomer Polymers 0.000 claims abstract description 51
239000000806 elastomer Substances 0.000 claims abstract description 50
239000000463 material Substances 0.000 claims abstract description 41
125000000466 oxiranyl group Chemical group 0.000 claims abstract description 26
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
239000011593 sulfur Substances 0.000 claims abstract description 11
239000004711 α-olefin Substances 0.000 claims abstract description 7
229920005989 resin Polymers 0.000 claims description 75
239000011347 resin Substances 0.000 claims description 75
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 38
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 33
229960004279 formaldehyde Drugs 0.000 claims description 27
229920000647 polyepoxide Polymers 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
239000003822 epoxy resin Substances 0.000 claims description 19
239000005060 rubber Substances 0.000 claims description 17
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 14
229930195733 hydrocarbon Natural products 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 11
229920001577 copolymer Polymers 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 10
150000001993 dienes Chemical class 0.000 claims description 9
229920005549 butyl rubber Polymers 0.000 claims description 8
229920005556 chlorobutyl Polymers 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
229920003052 natural elastomer Polymers 0.000 claims description 8
229920001194 natural rubber Polymers 0.000 claims description 8
229920001897 terpolymer Polymers 0.000 claims description 8
244000043261 Hevea brasiliensis Species 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
235000011187 glycerol Nutrition 0.000 claims description 6
150000005826 halohydrocarbons Chemical class 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical group C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 5
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 4
229940091173 hydantoin Drugs 0.000 claims description 4
150000004291 polyenes Chemical class 0.000 claims description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
229930185605 Bisphenol Natural products 0.000 claims description 3
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
229920000459 Nitrile rubber Polymers 0.000 claims description 3
KIKYOFDZBWIHTF-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-3-ene-1,2-dicarboxylate Chemical compound C1CC=CC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KIKYOFDZBWIHTF-UHFFFAOYSA-N 0.000 claims description 3
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
229920001084 poly(chloroprene) Polymers 0.000 claims description 3
229920002857 polybutadiene Polymers 0.000 claims description 3
239000005062 Polybutadiene Substances 0.000 claims description 2
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 2
150000002118 epoxides Chemical class 0.000 claims description 2
SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 claims description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
229920001169 thermoplastic Polymers 0.000 claims description 2
239000004416 thermosoftening plastic Substances 0.000 claims description 2
235000019256 formaldehyde Nutrition 0.000 claims 4
229920005555 halobutyl Polymers 0.000 claims 3
125000004968 halobutyl group Chemical group 0.000 claims 3
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 1
229920000089 Cyclic olefin copolymer Polymers 0.000 claims 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 1
150000001935 cyclohexenes Chemical class 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims 1
229920001195 polyisoprene Polymers 0.000 claims 1
229920005992 thermoplastic resin Polymers 0.000 claims 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims 1
229920000098 polyolefin Polymers 0.000 abstract description 8
238000000926 separation method Methods 0.000 description 26
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000008096 xylene Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 17
239000004593 Epoxy Substances 0.000 description 14
239000000047 product Substances 0.000 description 14
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
229920002943 EPDM rubber Polymers 0.000 description 11
239000000155 melt Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000004615 ingredient Substances 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 8
150000002989 phenols Chemical class 0.000 description 8
229940083608 sodium hydroxide Drugs 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
239000000126 substance Substances 0.000 description 8
ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 7
229920003319 Araldite® Polymers 0.000 description 7
230000032683 aging Effects 0.000 description 7
239000007859 condensation product Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
229940095050 propylene Drugs 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
239000002904 solvent Substances 0.000 description 7
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 6
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
239000005977 Ethylene Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
201000006747 infectious mononucleosis Diseases 0.000 description 6
150000002924 oxiranes Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229920003048 styrene butadiene rubber Polymers 0.000 description 6
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 5
241000694440 Colpidium aqueous Species 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000002174 Styrene-butadiene Substances 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
239000006229 carbon black Substances 0.000 description 4
239000004568 cement Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical group CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
235000013824 polyphenols Nutrition 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
238000010276 construction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
229910044991 metal oxide Inorganic materials 0.000 description 3
150000004706 metal oxides Chemical class 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 3
MMMNTDFSPSQXJP-UHFFFAOYSA-N orphenadrine citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 MMMNTDFSPSQXJP-UHFFFAOYSA-N 0.000 description 3
229920001568 phenolic resin Polymers 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000001294 propane Substances 0.000 description 3
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000008117 stearic acid Substances 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
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RZJKZTPKSRPUFJ-UHFFFAOYSA-N 5,5-dimethyl-1,3-bis(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound O=C1N(CC2OC2)C(=O)C(C)(C)N1CC1CO1 RZJKZTPKSRPUFJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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230000005484 gravity Effects 0.000 description 2
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239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
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239000011787 zinc oxide Substances 0.000 description 2
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RDAFFINKUCJOJK-UYIJSCIWSA-N (1z,5e)-cyclodeca-1,5-diene Chemical compound C1CC\C=C/CC\C=C\C1 RDAFFINKUCJOJK-UYIJSCIWSA-N 0.000 description 1
HOEFIGOFJSMARD-FUOWLQLWSA-N (1z,5z)-1-methylcycloocta-1,5-diene Chemical compound C\C1=C\CC\C=C/CC1 HOEFIGOFJSMARD-FUOWLQLWSA-N 0.000 description 1
KEMUGHMYINTXKW-NQOXHWNZSA-N (1z,5z)-cyclododeca-1,5-diene Chemical compound C1CCC\C=C/CC\C=C/CC1 KEMUGHMYINTXKW-NQOXHWNZSA-N 0.000 description 1
GWCMUONZBWHLRN-REXUQAFDSA-N (1z,6z)-cyclodeca-1,6-diene Chemical compound C1C\C=C/CCC\C=C/C1 GWCMUONZBWHLRN-REXUQAFDSA-N 0.000 description 1
PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
KMDLDWBXGMDTSA-ISLYRVAYSA-N (9e)-octadeca-1,9-diene Chemical compound CCCCCCCC\C=C\CCCCCCC=C KMDLDWBXGMDTSA-ISLYRVAYSA-N 0.000 description 1
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
239000004912 1,5-cyclooctadiene Substances 0.000 description 1
BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
GPEJOYPHWFOWNM-UHFFFAOYSA-N 2-dodecylphenol;formaldehyde Chemical compound O=C.CCCCCCCCCCCCC1=CC=CC=C1O GPEJOYPHWFOWNM-UHFFFAOYSA-N 0.000 description 1
SLQMKNPIYMOEGB-UHFFFAOYSA-N 2-methylhexa-1,5-diene Chemical compound CC(=C)CCC=C SLQMKNPIYMOEGB-UHFFFAOYSA-N 0.000 description 1
OWRACTVEYJLPRK-UHFFFAOYSA-N 3,3-dimethylhexa-1,5-diene Chemical compound C=CC(C)(C)CC=C OWRACTVEYJLPRK-UHFFFAOYSA-N 0.000 description 1
PPUYTKKLEAZCCW-UHFFFAOYSA-N 3-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC(O)=C1 PPUYTKKLEAZCCW-UHFFFAOYSA-N 0.000 description 1
OGJJVYFQXFXJKU-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hepta-2,5-diene Chemical compound C1C2C(C)=CC1C=C2 OGJJVYFQXFXJKU-UHFFFAOYSA-N 0.000 description 1
RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
MHCHQNXRVNQPHJ-UHFFFAOYSA-N 4-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=C(O)C=C1 MHCHQNXRVNQPHJ-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
UCKITPBQPGXDHV-UHFFFAOYSA-N 7-methylocta-1,6-diene Chemical compound CC(C)=CCCCC=C UCKITPBQPGXDHV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
241001441571 Hiodontidae Species 0.000 description 1
VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical class CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000004594 Masterbatch (MB) Substances 0.000 description 1
KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZAMASTWUZBWLNH-UHFFFAOYSA-N [S].CCCCCCCCCCCCCCCCCC(O)=O Chemical compound [S].CCCCCCCCCCCCCCCCCC(O)=O ZAMASTWUZBWLNH-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 description 1
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical compound C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229960004337 hydroquinone Drugs 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
BAPROVDXKNPHAM-UHFFFAOYSA-N n-(2-aminoethyl)-3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(=O)NCCN)=CC(C(C)(C)C)=C1O BAPROVDXKNPHAM-UHFFFAOYSA-N 0.000 description 1
150000002846 norbornadienes Chemical class 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
238000007670 refining Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910001388 sodium aluminate Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
239000012815 thermoplastic material Substances 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
IYQYZZHQSZMZIG-UHFFFAOYSA-N tricyclo[5.2.1.0(2.6)]deca-3,8-diene, 4.9-dimethyl Chemical compound C1C2C3C=C(C)CC3C1C=C2C IYQYZZHQSZMZIG-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

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)
Adhesives Or Adhesive Processes (AREA)
Phenolic Resins Or Amino Resins (AREA)

CA228,372A 1975-01-28 1975-06-03 Systeme augmentant les caracteristiques adhesives a base du produit de reaction de l'oxirane et de derives alkylphenol de novolac Expired CA1055643A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/544,772 US4073776A (en)	1975-01-28	1975-01-28	Tackifiers for elastomers
US05/574,625 US4073826A (en)	1975-01-28	1975-05-05	Tackifiers for elastomers

Publications (1)

Publication Number	Publication Date
CA1055643A true CA1055643A (fr)	1979-05-29

Family

ID=27067730

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA228,372A Expired CA1055643A (fr)	1975-01-28	1975-06-03	Systeme augmentant les caracteristiques adhesives a base du produit de reaction de l'oxirane et de derives alkylphenol de novolac

Country Status (7)

Country	Link
JP (1)	JPS5922745B2 (fr)
BR (1)	BR7505453A (fr)
CA (1)	CA1055643A (fr)
DE (1)	DE2537718C2 (fr)
FR (1)	FR2299359A1 (fr)
GB (1)	GB1497203A (fr)
MX (1)	MX148877A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4342843A (en) *	1979-03-01	1982-08-03	National Starch And Chemical Corp.	Neoprene latex contact adhesives
US4463110A (en) *	1981-02-24	1984-07-31	National Starch And Chemical Corporation	Neoprene latex contact adhesives
JPS60261706A (ja) *	1984-06-11	1985-12-25	Bridgestone Corp	耐久性の改良された重荷重バイアスタイヤ
US4608406A (en) *	1985-04-18	1986-08-26	Celanese Corporation	Stable aqueous epoxy resin dispersions
JP3447015B2 (ja) *	1993-04-23	2003-09-16	三井化学株式会社	エポキシ樹脂組成物
GB9314577D0 (en) *	1993-07-14	1993-08-25	Zeneca Ltd	Adhesion process
DE102006007108B4 (de) *	2006-02-16	2020-09-17	Lohmann Gmbh & Co. Kg	Reaktive Harzmischung und Verfahren zu deren Herstellung
EP3862376A1 (fr) *	2020-02-07	2021-08-11	Rain Carbon Germany GmbH	Agent poisseux pour composés élastomères
CN111484588A (zh) *	2020-06-10	2020-08-04	山东阳谷华泰化工股份有限公司	一种环氧油酸酯改性烷基苯酚-甲醛树脂橡胶增粘剂及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2723249A (en) *	1952-11-19	1955-11-08	Petrolite Corp	Phenol-aldehyde resins reacted with phenyl glycidyl ether
GB1092086A (en) *	1963-11-14	1967-11-22	Hooker Chemical Corp	Elastomeric compositions including a phenolic resin tackifier

1975
- 1975-06-03 CA CA228,372A patent/CA1055643A/fr not_active Expired
- 1975-06-25 FR FR7519873A patent/FR2299359A1/fr active Granted
- 1975-06-25 MX MX159234A patent/MX148877A/es unknown
- 1975-08-25 DE DE2537718A patent/DE2537718C2/de not_active Expired
- 1975-08-26 BR BR5453/75A patent/BR7505453A/pt unknown
1976
- 1976-01-01 JP JP51000732A patent/JPS5922745B2/ja not_active Expired
- 1976-01-16 GB GB1671/76A patent/GB1497203A/en not_active Expired

Also Published As

Publication number	Publication date
FR2299359A1 (fr)	1976-08-27
AU1037676A (en)	1977-08-11
JPS5922745B2 (ja)	1984-05-29
FR2299359B1 (fr)	1981-02-27
DE2537718C2 (de)	1984-09-20
GB1497203A (en)	1978-01-05
JPS5193944A (fr)	1976-08-18
MX148877A (es)	1983-06-29
BR7505453A (pt)	1976-11-30
DE2537718A1 (de)	1976-07-29

Publication	Publication Date	Title
US4073826A (en)	1978-02-14	Tackifiers for elastomers
US3287440A (en)	1966-11-22	Process for the cross-linking of unsaturated copolymers and ethylene-propylene terpolymers
EP0191299B1 (fr)	1992-08-26	Composition réticulante pour des mélanges de caoutchouc butyl ou caoutchouc butyl halogéné et de caoutchouc d'épihalohydrine
KR100587880B1 (ko)	2006-09-28	비 휘발성 레조르시놀 수지 및 그 제조 및 사용방법
US4699832A (en)	1987-10-13	Reinforced rubber mixtures, a process for their preparation and their use
KR101522162B1 (ko)	2015-05-21	점착제로서 사용하기 위한 변성 히드로카르빌페놀-알데히드 수지 및 이를 함유하는 고무 조성물
KR101092931B1 (ko)	2011-12-12	변성 레조르시놀 수지 및 그의 응용 방법
KR20170008782A (ko)	2017-01-24	변성 페놀 수지와, 상기 수지의 제조 방법 및 상기 수지를 강화 수지로서 사용하는 방법
CA1055643A (fr)	1979-05-29	Systeme augmentant les caracteristiques adhesives a base du produit de reaction de l'oxirane et de derives alkylphenol de novolac
CN105705541B (zh)	2018-08-24	通过水杨酸稳定的改性烷基苯酚-醛树脂
CA1283989C (fr)	1991-05-07	Vulcanisation d'une resine
CN111825818B (zh)	2023-11-21	原位烷基苯酚-醛树脂
EP0292701A2 (fr)	1988-11-30	Résine de gayule traitée par une résine phénolique et un polyéther et compositions de caoutchouc la contenant
WO2022140641A1 (fr)	2022-06-30	Résines phénoliques auto-polymérisables
US3455851A (en)	1969-07-15	Rubber reinforcing compositions comprising phenol/sulfur resins
US7135539B2 (en)	2006-11-14	Novolac resins, process for preparing them and uses thereof
US4073757A (en)	1978-02-14	Hardenable, boron-containing reinforcing resins for rubber
JPH0739518B2 (ja)	1995-05-01	接着性に優れた塩素化ポリエチレン組成物
JP7354459B2 (ja)	2023-10-02	エラストマー化合物用新規タッキファイヤー
US3050479A (en)	1962-08-21	Process comprising heat-treating halogenated butyl rubber in the presence of a novolac resin and thereafter curing, and product obtained thereby
JPH0611821B2 (ja)	1994-02-16	ゴム組成物