CA1083281A - Substances aqueuses contenant des resines phenoliques et des agents de reticulation croisee - Google Patents

Substances aqueuses contenant des resines phenoliques et des agents de reticulation croisee

Info

Publication number: CA1083281A
Authority: CA; Canada
Prior art keywords: water; novolak; composition according; phenolic; phenol
Prior art date: 1976-06-14
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

CA280,018A

Other languages

English (en)

Inventor

Peter J. Jazenski

John S. Sadowski

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.)

Lord Corp

Original Assignee

Lord Corp

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.)

1976-06-14

Filing date

1977-06-07

Publication date

1980-08-05

1977-06-07 Application filed by Lord Corp filed Critical Lord Corp

1980-08-05 Application granted granted Critical

1980-08-05 Publication of CA1083281A publication Critical patent/CA1083281A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 62
229920001568 phenolic resin Polymers 0.000 title claims abstract description 12
239000005011 phenolic resin Substances 0.000 title claims abstract description 11
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 9
239000003431 cross linking reagent Substances 0.000 title abstract description 6
239000000853 adhesive Substances 0.000 claims abstract description 105
230000001070 adhesive effect Effects 0.000 claims abstract description 105
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 80
229920005989 resin Polymers 0.000 claims abstract description 73
239000011347 resin Substances 0.000 claims abstract description 73
229920003986 novolac Polymers 0.000 claims abstract description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 56
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 44
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 41
244000226021 Anacardium occidentale Species 0.000 claims description 13
235000020226 cashew nut Nutrition 0.000 claims description 13
229920006324 polyoxymethylene Polymers 0.000 claims description 13
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 11
239000007787 solid Substances 0.000 claims description 11
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 10
239000002243 precursor Substances 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229920001577 copolymer Polymers 0.000 claims description 8
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 8
-1 methylene amino Chemical group 0.000 claims description 8
229920003987 resole Polymers 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
229920001519 homopolymer Polymers 0.000 claims description 7
150000008442 polyphenolic compounds Polymers 0.000 claims description 7
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
150000001241 acetals Chemical class 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 claims 1
239000000758 substrate Substances 0.000 abstract description 14
229910052751 metal Inorganic materials 0.000 abstract description 11
239000002184 metal Substances 0.000 abstract description 11
239000000654 additive Substances 0.000 abstract description 2
239000000945 filler Substances 0.000 abstract description 2
229920000642 polymer Polymers 0.000 abstract 2
239000000025 natural resin Substances 0.000 abstract 1
229920003002 synthetic resin Polymers 0.000 abstract 1
239000000057 synthetic resin Substances 0.000 abstract 1
229960004279 formaldehyde Drugs 0.000 description 25
235000019256 formaldehyde Nutrition 0.000 description 22
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 18
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
229920001971 elastomer Polymers 0.000 description 15
239000000839 emulsion Substances 0.000 description 14
229910000831 Steel Inorganic materials 0.000 description 13
238000000034 method Methods 0.000 description 13
239000010959 steel Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
229920000459 Nitrile rubber Polymers 0.000 description 11
230000007613 environmental effect Effects 0.000 description 11
239000003921 oil Substances 0.000 description 10
150000002989 phenols Chemical class 0.000 description 10
235000010299 hexamethylene tetramine Nutrition 0.000 description 9
239000004312 hexamethylene tetramine Substances 0.000 description 9
229960004011 methenamine Drugs 0.000 description 9
239000000806 elastomer Substances 0.000 description 8
102000011632 Caseins Human genes 0.000 description 7
108010076119 Caseins Proteins 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
239000005060 rubber Substances 0.000 description 7
229940080237 sodium caseinate Drugs 0.000 description 7
229930040373 Paraformaldehyde Natural products 0.000 description 6
229920003052 natural elastomer Polymers 0.000 description 6
229920001194 natural rubber Polymers 0.000 description 6
229920003051 synthetic elastomer Polymers 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
229920002866 paraformaldehyde Polymers 0.000 description 4
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000005061 synthetic rubber Substances 0.000 description 3
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
241000051981 Allolepis Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229920013683 Celanese Polymers 0.000 description 2
229920005123 Celcon® Polymers 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
239000004677 Nylon Substances 0.000 description 2
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000000712 assembly Effects 0.000 description 2
238000000429 assembly Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
239000010960 cold rolled steel Substances 0.000 description 2
230000002950 deficient Effects 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
239000000446 fuel Substances 0.000 description 2
238000001879 gelation Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000007654 immersion Methods 0.000 description 2
239000012784 inorganic fiber Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229920001778 nylon Polymers 0.000 description 2
OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 2
229960001553 phloroglucinol Drugs 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
229940079877 pyrogallol Drugs 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
XOUAQPDUNFWPEM-UHFFFAOYSA-N 2,3,4-tris(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1CO XOUAQPDUNFWPEM-UHFFFAOYSA-N 0.000 description 1
XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 1
DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 1
ITHKENCTUWNIHF-UHFFFAOYSA-N 2-(methylideneamino)prop-2-enenitrile Chemical compound C=NC(C#N)=C ITHKENCTUWNIHF-UHFFFAOYSA-N 0.000 description 1
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
KFVIYKFKUYBKTP-UHFFFAOYSA-N 2-n-(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCNC1=NC(N)=NC(N)=N1 KFVIYKFKUYBKTP-UHFFFAOYSA-N 0.000 description 1
MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-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
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
206010059837 Adhesion Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
KWVOQVCDRQQEHI-UHFFFAOYSA-N CP(=O)N1CC1 Chemical compound CP(=O)N1CC1 KWVOQVCDRQQEHI-UHFFFAOYSA-N 0.000 description 1
229920004943 Delrin® Polymers 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000590428 Panacea Species 0.000 description 1
229930182556 Polyacetal Natural products 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000002313 adhesive film Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
QUEICCDHEFTIQD-UHFFFAOYSA-N buta-1,3-diene;2-ethenylpyridine;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=N1 QUEICCDHEFTIQD-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
238000003490 calendering Methods 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004581 coalescence Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
SZNYYWIUQFZLLT-UHFFFAOYSA-N isopropylmethyl ether Natural products CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 1
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229920000126 latex Polymers 0.000 description 1
DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
WNUPGDZWJCHVAF-UHFFFAOYSA-N n-(hydroxymethyl)-n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)N(CO)C(=O)C=C WNUPGDZWJCHVAF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000037452 priming Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
229950001353 tretamine Drugs 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- 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
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/02—Polyacetals containing polyoxymethylene sequences only
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- 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
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/16—Addition or condensation polymers of aldehydes or ketones according to C08L59/00 - C08L61/00; Derivatives thereof
- 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
- C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts
- 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
- C08L2666/54—Inorganic substances

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Adhesives Or Adhesive Processes (AREA)
Phenolic Resins Or Amino Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA280,018A 1976-06-14 1977-06-07 Substances aqueuses contenant des resines phenoliques et des agents de reticulation croisee Expired CA1083281A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US69570576A	1976-06-14	1976-06-14
US695,705		1976-06-14

Publications (1)

Publication Number	Publication Date
CA1083281A true CA1083281A (fr)	1980-08-05

Family

ID=24794158

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA280,018A Expired CA1083281A (fr)	1976-06-14	1977-06-07	Substances aqueuses contenant des resines phenoliques et des agents de reticulation croisee

Country Status (10)

Country	Link
JP (1)	JPS5817515B2 (fr)
AU (1)	AU517339B2 (fr)
CA (1)	CA1083281A (fr)
DE (1)	DE2726423C2 (fr)
FR (1)	FR2355054A1 (fr)
GB (1)	GB1564235A (fr)
IT (1)	IT1080874B (fr)
SE (1)	SE439321B (fr)
SU (1)	SU906386A3 (fr)
ZA (1)	ZA773430B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5827227B2 (ja) *	1979-07-25	1983-06-08	リグナイト株式会社	耐火物
JPS59137216U (ja) *	1983-03-07	1984-09-13	昭和電工建材株式会社	未硬化成形品の移し換え装置
JPS59137218U (ja) *	1983-03-07	1984-09-13	昭和電工建材株式会社	未硬化成形品の移し換え装置
GB2140347B (en) *	1983-05-23	1986-09-24	British Steel Corp	Improvements in and relating to containers
JPS61186407U (fr) *	1985-05-15	1986-11-20
DE3639233A1 (de) *	1986-11-20	1988-05-26	Huettenes Albertus	Kalthaertendes formstoff-bindemittel und dessen verwendung
JPS6434705A (en) *	1987-06-26	1989-02-06	Inax Corp	Apparatus for stacking tile
US5030692A (en) *	1988-08-10	1991-07-09	Indspec Chemical Corporation	Rubber compounding resorcinolic resins and process for making the same
JP3413897B2 (ja) *	1992-12-17	2003-06-09	住友化学工業株式会社	共縮合物およびそれを含有するゴム組成物
EP1699838B1 (fr) *	2003-11-20	2013-09-04	SI Group, Inc.	Resines novolaques et compositions de caoutchouc les contenant
CN101065445B (zh)	2004-12-27	2011-05-11	住友电木株式会社	热固性树脂组合物、热固性树脂成型材料及其固化物
RU2474629C2 (ru) *	2007-12-19	2013-02-10	Дайнеа Ой	Смола для получения неорганического волокнистого материала
CN103289619B (zh) *	2013-06-04	2015-05-27	南通鸿图橡塑有限公司	复合改性环保型水性酚醛树脂胶黏剂
US20190048120A1 (en) *	2017-08-11	2019-02-14	Sumitomo Bakelite Europe N. V.	Resorcinol resins and compositions derived thereform
CN112852361B (zh) *	2021-03-26	2023-04-11	广西南宁市完美木业有限公司	一种防腐易脱模建筑模板面胶及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3210309A (en) *	1960-06-21	1965-10-05	Borden Co	Curing phenolic resins with alphapolyoxymethylene

1977
- 1977-06-07 CA CA280,018A patent/CA1083281A/fr not_active Expired
- 1977-06-07 ZA ZA00773430A patent/ZA773430B/xx unknown
- 1977-06-08 SE SE7706694A patent/SE439321B/xx not_active IP Right Cessation
- 1977-06-09 GB GB24200/77A patent/GB1564235A/en not_active Expired
- 1977-06-11 DE DE2726423A patent/DE2726423C2/de not_active Expired
- 1977-06-13 SU SU772494667A patent/SU906386A3/ru active
- 1977-06-14 FR FR7718149A patent/FR2355054A1/fr active Granted
- 1977-06-14 JP JP52070426A patent/JPS5817515B2/ja not_active Expired
- 1977-06-14 IT IT24664/77A patent/IT1080874B/it active
- 1977-06-14 AU AU26059/77A patent/AU517339B2/en not_active Expired

Also Published As

Publication number	Publication date
JPS5313647A (en)	1978-02-07
SE7706694L (sv)	1977-12-15
FR2355054A1 (fr)	1978-01-13
SE439321B (sv)	1985-06-10
AU517339B2 (en)	1981-07-23
GB1564235A (en)	1980-04-02
AU2605977A (en)	1978-12-21
DE2726423A1 (de)	1977-12-29
ZA773430B (en)	1978-04-26
DE2726423C2 (de)	1987-02-19
SU906386A3 (ru)	1982-02-15
FR2355054B1 (fr)	1983-07-18
IT1080874B (it)	1985-05-16
JPS5817515B2 (ja)	1983-04-07

Legal Events

Date	Code	Title	Description
1997-08-05	MKEX	Expiry

Publication	Publication Date	Title
US4167500A (en)	1979-09-11	Aqueous compositions comprising phenolic resin and crosslinking agent
US5162156A (en)	1992-11-10	Phenolic resin adhesion promoters and adhesive compositions, and bonding method employing same
GB1564235A (en)	1980-04-02	Aqueous compositions comprising phenolic resin and cross linking agent
US5385979A (en)	1995-01-31	Primer and adhesive compositions based on chlorinated polyolefins having high chlorine contents
US3226276A (en)	1965-12-28	Method of bonding cord to rubber with a phenol-aldehyde blocked polyisocyanate
EP0624184B1 (fr)	1998-09-09	Compositions adhesives aqueuses contenant des resines phenoliques stabilisees
CA1110797A (fr)	1981-10-13	Emulsions aqueuses de resine de polyurethane- formaldehyde phenolique, employees comme adhesifs, produits d'amorce et revetements de surface
EP1144535B1 (fr)	2004-11-03	Adhesif a depot automatique
US3784516A (en)	1974-01-08	Rapid curing resin compositions employing a phenol-aldehyde condensation polymer reacted with a bis-aryl amine
US3697310A (en)	1972-10-10	Method of bonding polyester synthetic fibrous material to rubber compound
US3476706A (en)	1969-11-04	Curing resorcinol-aldehyde resol resins employing aniline or aniline salts
CA1152688A (fr)	1983-08-23	Methode de preparation de vulcanisats de caoutchouc arme, et emploi du produit connexe
US4238379A (en)	1980-12-09	Water based oligomeric primers for aluminum and aluminum alloys
US2430053A (en)	1947-11-04	Polyvinyl butyral-resorcinol-formaldehyde adhesive
US3880694A (en)	1975-04-29	Method of bonding using rapid curing resin compositions comprising the reaction product of an aldehyde condensation polymer with a primary aromatic amine further reacted with a curing agent
CA2202642C (fr)	2003-04-08	Adhesif monocouche destine a lier des urethannes coulables a un metal
US4350800A (en)	1982-09-21	Process for the preparation of synthetic resins based on resorcinol compounds
EP0788522B1 (fr)	1999-11-10	Derives acetal de composes de resol
US4263190A (en)	1981-04-21	Adhesion of textile cords to rubber using a butadiene-styrene vinylpyridine rubber latex and an aldehyde condensate-glyoxal reaction products mixture
CA2351748A1 (fr)	2002-01-14	Produits en caoutchouc avec faible accumulation de chaleur due a des efforts mecaniques
US5374678A (en)	1994-12-20	Adhesive
WO1993008223A1 (fr)	1993-04-29	Colles thermofusibles autoadhesives stables en stockage
JPH10512618A (ja)	1998-12-02	可とう化したフェノール樹脂、その製造方法および使用
US2538753A (en)	1951-01-23	Aldehyde condensation resins
AU684495B2 (en)	1997-12-18	Resins