CA1124439A - Resin salts - Google Patents
Resin saltsInfo
- Publication number
- CA1124439A CA1124439A CA309,420A CA309420A CA1124439A CA 1124439 A CA1124439 A CA 1124439A CA 309420 A CA309420 A CA 309420A CA 1124439 A CA1124439 A CA 1124439A
- Authority
- CA
- Canada
- Prior art keywords
- salts
- parts
- alkanolamine
- resorcinol
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- 239000011347 resin Substances 0.000 title description 6
- 229920005989 resin Polymers 0.000 title description 6
- 229920001971 elastomer Polymers 0.000 claims abstract description 18
- 229920000728 polyester Polymers 0.000 claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 31
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 16
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920000126 latex Polymers 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 3
- 150000001923 cyclic compounds Chemical class 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000004816 latex Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- -1 alkyl monohydroxybenzene Chemical compound 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 4
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007859 condensation product Substances 0.000 abstract description 21
- 229910021529 ammonia Inorganic materials 0.000 abstract description 6
- 150000003863 ammonium salts Chemical class 0.000 abstract description 3
- 239000003517 fume Substances 0.000 abstract description 3
- JFPQTPXIKIOBGI-UHFFFAOYSA-N benzene-1,2-diol;formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1.OC1=CC=CC=C1O JFPQTPXIKIOBGI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 1
- CCYWQSKYRLIWLA-UHFFFAOYSA-N 2-aminocyclohexane-1-thione Chemical compound NC1CCCCC1=S CCYWQSKYRLIWLA-UHFFFAOYSA-N 0.000 description 1
- XFIQVAWHIIPESL-UHFFFAOYSA-N 2-aminoethanol;2-[bis(2-hydroxyethyl)amino]ethanol;2-(2-hydroxyethylamino)ethanol Chemical compound NCCO.OCCNCCO.OCCN(CCO)CCO XFIQVAWHIIPESL-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- YMGFTDKNIWPMGF-QHCPKHFHSA-N Salvianolic acid A Natural products OC(=O)[C@H](Cc1ccc(O)c(O)c1)OC(=O)C=Cc2ccc(O)c(O)c2C=Cc3ccc(O)c(O)c3 YMGFTDKNIWPMGF-QHCPKHFHSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229950004864 olamine Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- NGWSFRIPKNWYAO-UHFFFAOYSA-N salinosporamide A Natural products N1C(=O)C(CCCl)C2(C)OC(=O)C21C(O)C1CCCC=C1 NGWSFRIPKNWYAO-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10S156/91—Bonding tire cord and elastomer: improved adhesive system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Reinforced Plastic Materials (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34902/77 | 1977-08-19 | ||
| GB3490277 | 1977-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124439A true CA1124439A (en) | 1982-05-25 |
Family
ID=10371322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,420A Expired CA1124439A (en) | 1977-08-19 | 1978-08-15 | Resin salts |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4957846A (en) * | 1988-12-27 | 1990-09-18 | Olin Hunt Specialty Products Inc. | Radiation sensitive compound and mixtures with trinuclear novolak oligomer with o-naphthoquinone diazide sulfonyl group |
| AR068501A1 (es) * | 2007-09-21 | 2009-11-18 | Saint Gobain Abrasives Inc | Formulacion de resina fenolica y recubrimientos para productos abrasivos |
| DE102022131398A1 (de) | 2022-11-28 | 2024-05-29 | Jenoptik Industrial Metrology Germany Gmbh | Bohrungsinspektionsvorrichtung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878198A (en) * | 1954-06-28 | 1959-03-17 | Koppers Co Inc | Quick-drying oleoresinous coating compositions containing resorcinol-p-alkylphenol-aldehyde resins and a process of preparing these resins |
| US3069374A (en) * | 1958-05-07 | 1962-12-18 | Exxon Research Engineering Co | Process for preparing butyl rubber latex containing phenol-aldehyde resin and an ammonium alkyl sulfate |
| GB1140528A (en) * | 1965-10-18 | 1969-01-22 | Ici Ltd | Substances for use in improving the bondability to rubber or shaped articles of polyester |
| US4035435A (en) * | 1968-02-26 | 1977-07-12 | Compagnie Generale Des Etablissements Michelin, Raison Sociale Michelin & Cie | Adherence of textile fibers to unsaturated polymers |
| DE2063838A1 (de) * | 1969-12-29 | 1971-07-01 | Unitika K K , Amagasaki, Hyogoken (Japan) | Klebemittel zum Verkleben von Gummi und Kunststoffen, insbesondere Polyestern |
| US3834934A (en) * | 1971-03-22 | 1974-09-10 | American Cyanamid Co | Adhesion of fibrous material to rubber |
| US3855168A (en) * | 1971-08-03 | 1974-12-17 | Mitsubishi Rayon Co | Adhesive composition for bonding polyester fiber to rubber |
| US3888813A (en) * | 1973-06-25 | 1975-06-10 | Koppers Co Inc | Tire cord dip for polyester fibers |
| US3981760A (en) * | 1974-11-13 | 1976-09-21 | The General Tire & Rubber Company | Adhesion of glass fibers to rubber with adhesive layer comprising a cresol-formaldehyde-resorcinol resin |
-
1978
- 1978-08-15 CA CA309,420A patent/CA1124439A/en not_active Expired
- 1978-08-15 DE DE7878300251T patent/DE2860859D1/de not_active Expired
- 1978-08-15 EP EP78300251A patent/EP0001321B1/en not_active Expired
- 1978-08-16 IT IT26791/78A patent/IT1098043B/it active
- 1978-08-18 NZ NZ188186A patent/NZ188186A/xx unknown
- 1978-08-18 AU AU39083/78A patent/AU518820B2/en not_active Expired
- 1978-08-18 BR BR7805327A patent/BR7805327A/pt unknown
- 1978-08-18 JP JP10084378A patent/JPS5441853A/ja active Granted
- 1978-08-20 IL IL55391A patent/IL55391A/xx unknown
- 1978-08-21 US US05/935,612 patent/US4151028A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1098043B (it) | 1985-08-31 |
| IL55391A0 (en) | 1978-10-31 |
| JPS6313978B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-29 |
| AU3908378A (en) | 1980-02-21 |
| DE2860859D1 (en) | 1981-10-29 |
| IT7826791A0 (it) | 1978-08-16 |
| US4151028A (en) | 1979-04-24 |
| BR7805327A (pt) | 1979-04-17 |
| AU518820B2 (en) | 1981-10-22 |
| NZ188186A (en) | 1980-10-24 |
| IL55391A (en) | 1981-11-30 |
| EP0001321B1 (en) | 1981-07-22 |
| EP0001321A1 (en) | 1979-04-04 |
| JPS5441853A (en) | 1979-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |