DE3213340C2 - - Google Patents
Info
- Publication number
- DE3213340C2 DE3213340C2 DE3213340A DE3213340A DE3213340C2 DE 3213340 C2 DE3213340 C2 DE 3213340C2 DE 3213340 A DE3213340 A DE 3213340A DE 3213340 A DE3213340 A DE 3213340A DE 3213340 C2 DE3213340 C2 DE 3213340C2
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- formaldehyde
- acid
- resorcinol
- mixture
- 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 - Lifetime
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 117
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 14
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 229920003987 resole Polymers 0.000 claims description 7
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- FRNQLQRBNSSJBK-UHFFFAOYSA-N divarinol Chemical compound CCCC1=CC(O)=CC(O)=C1 FRNQLQRBNSSJBK-UHFFFAOYSA-N 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- JOZMGUQZTOWLAS-UHFFFAOYSA-N 5-butylbenzene-1,3-diol Chemical compound CCCCC1=CC(O)=CC(O)=C1 JOZMGUQZTOWLAS-UHFFFAOYSA-N 0.000 claims description 2
- RKCBNCOFPKXLIQ-UHFFFAOYSA-N 5-propan-2-ylbenzene-1,3-diol Chemical compound CC(C)C1=CC(O)=CC(O)=C1 RKCBNCOFPKXLIQ-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- OPUXJCNMHZSXFM-UHFFFAOYSA-N benzene-1,3-diol 5-methylbenzene-1,3-diol Chemical class CC=1C=C(C=C(O)C1)O.C1(O)=CC(O)=CC=C1 OPUXJCNMHZSXFM-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 229960001755 resorcinol Drugs 0.000 description 29
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 26
- 239000000853 adhesive Substances 0.000 description 25
- 230000001070 adhesive effect Effects 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000835 fiber Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- 229920000126 latex Polymers 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- -1 m-substituted Phenols Chemical class 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- RCNCKKACINZDOI-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-diol Chemical compound CC1=CC(O)=CC(O)=C1C RCNCKKACINZDOI-UHFFFAOYSA-N 0.000 description 2
- MSFGJICDOLGZQK-UHFFFAOYSA-N 5-ethylbenzene-1,3-diol Chemical compound CCC1=CC(O)=CC(O)=C1 MSFGJICDOLGZQK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GHVHDYYKJYXFGU-UHFFFAOYSA-N Beta-Orcinol Chemical compound CC1=CC(O)=C(C)C(O)=C1 GHVHDYYKJYXFGU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000004886 process control Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 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
- 229930188104 Alkylresorcinol Natural products 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001026509 Kata Species 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
- 235000010678 Paulownia tomentosa Nutrition 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
- 244000153888 Tung Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920006173 natural rubber latex 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
- 239000004058 oil shale Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 238000010998 test method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000004636 vulcanized rubber 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
- C08G8/24—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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
-
- 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]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
- Y10T428/31794—Of cross-linked polyester
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5302481A JPS6051490B2 (ja) | 1981-04-10 | 1981-04-10 | レゾルシン系共重合体の製造方法 |
| JP5302581A JPS57167313A (en) | 1981-04-10 | 1981-04-10 | Production of alkylresorcinol copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3213340A1 DE3213340A1 (de) | 1983-05-05 |
| DE3213340C2 true DE3213340C2 (en:Method) | 1991-10-24 |
Family
ID=26393726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3213340A Granted DE3213340A1 (de) | 1981-04-10 | 1982-04-08 | Resorcin-mischpolymerisate und verfahren zu ihrer herstellung |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4376854A (en:Method) |
| DE (1) | DE3213340A1 (en:Method) |
| GB (1) | GB2101618B (en:Method) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2053739T3 (es) * | 1987-07-06 | 1994-08-01 | Bridgestone Corp | Composicion adhesiva para materiales fibrosos y procedimiento para su preparacion. |
| US4970287A (en) * | 1987-11-23 | 1990-11-13 | Olin Hunt Specialty Products Inc. | Thermally stable phenolic resin compositions with ortho, ortho methylene linkage |
| US5024921A (en) * | 1987-11-23 | 1991-06-18 | Ocg Microelectronic Materials, Inc. | Thermally stable light-sensitive compositions with o-quinone diazide and phenolic resin used in a method of forming a positive photoresist image |
| US4837121A (en) * | 1987-11-23 | 1989-06-06 | Olin Hunt Specialty Products Inc. | Thermally stable light-sensitive compositions with o-quinone diazide and phenolic resin |
| DE69621221T2 (de) * | 1995-10-13 | 2003-02-06 | Bridgestone Corp., Tokio/Tokyo | Klebstoffzusammensetzung und luftreifen |
| US5847058A (en) * | 1996-04-05 | 1998-12-08 | Masonite Corporation | Alkylresorcinol modified phenol-aldehyde resol resin and binder system, and method of making same |
| GB2350616B (en) * | 1999-05-04 | 2003-07-30 | Swan Thomas & Co Ltd | Novolak resins used as bonding agents |
| US7196156B2 (en) * | 2002-12-13 | 2007-03-27 | Indspec Chemical Corporation | Flexibilized resorcinolic novolak resins and method of making same |
| KR101087348B1 (ko) * | 2003-10-07 | 2011-11-25 | 호도가야 가가쿠 고교 가부시키가이샤 | 레조르시놀-포르말린 수지의 제조 방법 |
| PL1842864T3 (pl) * | 2005-01-25 | 2013-12-31 | Hodogaya Chemical Co Ltd | Żywica rezorcynowo-formaldehydowa modyfikowana ketonem |
| WO2007114228A1 (ja) * | 2006-03-31 | 2007-10-11 | Central Glass Company, Limited | ガラス繊維被覆用塗布液およびそれを用いたゴム補強用ガラス繊維 |
| US20080073615A1 (en) * | 2006-07-24 | 2008-03-27 | Sumitomo Chemical Company, Limited | Method for producing resorcin/formaldehyde resin |
| WO2008038742A1 (en) * | 2006-09-29 | 2008-04-03 | Hodogaya Chemical Co., Ltd. | Process for producing mek-modified resorcin/formalin resin parallelly carrying out recovery and reuse of specified raw material |
| EA200970362A1 (ru) * | 2006-10-13 | 2009-10-30 | Индспек Кемикал Корпорейшн | Модифицированные алкилрезорциновые смолы и их использование |
| BR112013022759A2 (pt) | 2011-03-09 | 2019-09-24 | Georgia Pacific Chemicals Llc | composições ligantes de duas fases e métodos para fabricação e uso das mesmas |
| EP3519481B1 (en) * | 2016-09-28 | 2023-04-19 | SHPP Global Technologies B.V. | Phenylene ether copolymer and compositions comprising same |
| CN112592447B (zh) * | 2020-12-15 | 2022-02-11 | 北京彤程创展科技有限公司 | 一种混合烷基间苯二酚改性粘合树脂及其制备方法、橡胶组合物和橡胶制品 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2477641A (en) * | 1946-01-05 | 1949-08-02 | Westinghouse Electric Corp | Polyhydroxy benzene-formaldehyde resinous compositions and method of preparing the same |
| US2614096A (en) * | 1949-06-16 | 1952-10-14 | Borden Co | Condensation products of phenol, formaldehyde, and unsubstituted mononuclear dihydric phenols |
| 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 |
| US3437610A (en) * | 1965-12-27 | 1969-04-08 | Koppers Co Inc | Resorcinol-aldehyde resin and polyester tire cord adhesive made therefrom |
| US3422068A (en) * | 1966-02-25 | 1969-01-14 | Weyerhaeuser Co | Method of producing an ortho-directed phenolic resin by condensing phenol and hcho in the presence of a bivalent metal ion and then adding resorcinol,and the resultant product |
| US3835082A (en) * | 1970-07-30 | 1974-09-10 | Monsanto Co | Aqueous alkaline solution of an aldehyde conjoint condensate of resorcinol and saturated resorcinol polymer |
| US4009304A (en) * | 1971-09-30 | 1977-02-22 | Air Products And Chemicals, Inc. | Fluorinated polyester tire reinforcement materials |
| US4112160A (en) * | 1972-01-11 | 1978-09-05 | Sumitomo Durez Company, Ltd. | Solid adherend substrates bonded with rubber cement compositions |
| JPS5226275B2 (en:Method) * | 1973-03-27 | 1977-07-13 | ||
| CA1050182A (en) * | 1974-03-11 | 1979-03-06 | Maurice F. Gillern | Phenol-formaldehyde-resorcinol resins and adhesives |
| GB1593933A (en) * | 1977-01-24 | 1981-07-22 | Sumitomo Chemical Co | Resin for use in rubber compounding |
-
1982
- 1982-04-05 US US06/365,790 patent/US4376854A/en not_active Expired - Fee Related
- 1982-04-08 GB GB8210489A patent/GB2101618B/en not_active Expired
- 1982-04-08 DE DE3213340A patent/DE3213340A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3213340A1 (de) | 1983-05-05 |
| GB2101618A (en) | 1983-01-19 |
| US4376854A (en) | 1983-03-15 |
| GB2101618B (en) | 1984-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |