DE1520189A1 - Klebstofftauchbad fuer Reifencord,sowie Verfahren zur Herstellung bestimmter Resorcin-Aldehyd-Harze - Google Patents
Klebstofftauchbad fuer Reifencord,sowie Verfahren zur Herstellung bestimmter Resorcin-Aldehyd-HarzeInfo
- Publication number
- DE1520189A1 DE1520189A1 DE19641520189 DE1520189A DE1520189A1 DE 1520189 A1 DE1520189 A1 DE 1520189A1 DE 19641520189 DE19641520189 DE 19641520189 DE 1520189 A DE1520189 A DE 1520189A DE 1520189 A1 DE1520189 A1 DE 1520189A1
- Authority
- DE
- Germany
- Prior art keywords
- resorcinol
- aldehyde
- resin
- mol
- amount
- 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.)
- Pending
Links
- 229920005989 resin Polymers 0.000 title claims description 69
- 239000011347 resin Substances 0.000 title claims description 69
- 239000000853 adhesive Substances 0.000 title claims description 34
- 230000001070 adhesive effect Effects 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 title claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 63
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 38
- 150000001299 aldehydes Chemical class 0.000 claims description 29
- 229920005549 butyl rubber Polymers 0.000 claims description 29
- 229920000126 latex Polymers 0.000 claims description 27
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims description 26
- 229960003868 paraldehyde Drugs 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 22
- 239000004816 latex Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 229920001971 elastomer Polymers 0.000 claims description 14
- 239000005060 rubber Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000007654 immersion Methods 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 230000003068 static effect Effects 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920003052 natural elastomer Polymers 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000007598 dipping method Methods 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000005061 synthetic rubber Substances 0.000 description 3
- JGEGJYXHCFUMJF-UHFFFAOYSA-N 4-methylpentanal Chemical compound CC(C)CCC=O JGEGJYXHCFUMJF-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WDMOXLRWVGEXJV-UHFFFAOYSA-N 8-methylnonanal Chemical compound CC(C)CCCCCCC=O WDMOXLRWVGEXJV-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 210000000544 articulatio talocruralis Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- -1 bromobutyl Chemical group 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
-
- 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
- C08G8/22—Resorcinol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
-
- 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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31826—Of natural rubber
- Y10T428/31833—Next to aldehyde or ketone condensation product or addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25255963 US3242118A (en) | 1963-01-21 | 1963-01-21 | Resorcinol-aldehyde resin and tire cord adhesive made therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1520189A1 true DE1520189A1 (de) | 1970-01-22 |
Family
ID=22956522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641520189 Pending DE1520189A1 (de) | 1963-01-21 | 1964-01-18 | Klebstofftauchbad fuer Reifencord,sowie Verfahren zur Herstellung bestimmter Resorcin-Aldehyd-Harze |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3242118A (enExample) |
| DE (1) | DE1520189A1 (enExample) |
| GB (1) | GB1051262A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3405754A (en) * | 1964-04-27 | 1968-10-15 | Firestone Tire & Rubber Co | Tires containing ethylene-propylene-diene rubber and process of manufacture |
| US3443986A (en) * | 1964-08-24 | 1969-05-13 | Nippon Rayon Kk | Process for improving the adhesion of fibrous materials to rubber |
| US3330794A (en) * | 1965-02-03 | 1967-07-11 | Du Pont | Copolymer of an epoxidized olefin and a non-conjugated diene |
| US3437610A (en) * | 1965-12-27 | 1969-04-08 | Koppers Co Inc | Resorcinol-aldehyde resin and polyester tire cord adhesive made therefrom |
| US3367976A (en) * | 1966-08-22 | 1968-02-06 | Koppers Co Inc | Substituted resorcinol compound and method of making same |
| US3431241A (en) * | 1967-05-15 | 1969-03-04 | Koppers Co Inc | Monoisocyanate condensed resorcinol-aldehyde resins |
| US3609108A (en) * | 1969-01-31 | 1971-09-28 | Alfred J Kolka | Rubber modified with tris-substituted resorcinol compounds |
| US4314050A (en) * | 1978-10-30 | 1982-02-02 | Ppg Industries, Inc. | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers |
| US4393189A (en) * | 1978-10-30 | 1983-07-12 | Ppg Industries, Inc. | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers |
| US4278659A (en) * | 1978-12-22 | 1981-07-14 | The Gillette Company | Hair setting and bodying composition and method |
| JPS55155013A (en) * | 1979-05-21 | 1980-12-03 | Sumitomo Bakelite Co Ltd | Preparation of quick-curing phenol resin |
| US4338295A (en) * | 1980-11-12 | 1982-07-06 | The Gillette Company | Hair setting and bodying composition and method |
| US4476191A (en) * | 1981-11-16 | 1984-10-09 | Ppg Industries, Inc. | Resorcinol-aldehyde resin composition for an adhesive system to be applied to glass fibers |
| US6054527A (en) * | 1996-12-27 | 2000-04-25 | Voss; Gary D. | High adhesion of a variety of rubber compounds to fabric using a single resorcinol-formaldehyde latex composition |
| WO2007127065A2 (en) * | 2006-04-21 | 2007-11-08 | Living Proof, Inc. | In situ polymerization for hair treatment |
| CN116376487A (zh) * | 2023-05-25 | 2023-07-04 | 兰溪市克莱森助剂有限公司 | 一种橡胶粘合剂re的无废水制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1598546A (en) * | 1919-12-19 | 1926-08-31 | Bakelite Corp | Resinous bodies derived from acetaldehyde and process of making the same |
| US3116164A (en) * | 1960-04-11 | 1963-12-31 | Exxon Research Engineering Co | Non-woven fabric bonded with butyl rubber phenol-formaldehyde resol |
-
0
- GB GB1051262D patent/GB1051262A/en not_active Expired
-
1963
- 1963-01-21 US US25255963 patent/US3242118A/en not_active Expired - Lifetime
-
1964
- 1964-01-18 DE DE19641520189 patent/DE1520189A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3242118A (en) | 1966-03-22 |
| GB1051262A (enExample) | 1900-01-01 |
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