CA1050182A - Phenol-formaldehyde-resorcinol resins and adhesives - Google Patents
Phenol-formaldehyde-resorcinol resins and adhesivesInfo
- Publication number
- CA1050182A CA1050182A CA216,936A CA216936A CA1050182A CA 1050182 A CA1050182 A CA 1050182A CA 216936 A CA216936 A CA 216936A CA 1050182 A CA1050182 A CA 1050182A
- Authority
- CA
- Canada
- Prior art keywords
- adhesive
- formaldehyde
- composition
- phenol
- resorcinol
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 108
- 239000011347 resin Substances 0.000 title claims abstract description 108
- 239000000853 adhesive Substances 0.000 title claims abstract description 84
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 84
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 199
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 101
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000004840 adhesive resin Substances 0.000 claims abstract description 40
- 229920006223 adhesive resin Polymers 0.000 claims abstract description 40
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000012670 alkaline solution Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 230000008569 process Effects 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 23
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 13
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 12
- 229920001568 phenolic resin Polymers 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000011342 resin composition Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 235000020354 squash Nutrition 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 abstract description 61
- 239000002023 wood Substances 0.000 abstract description 19
- 238000010030 laminating Methods 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 238000012986 modification Methods 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- 229960004279 formaldehyde Drugs 0.000 description 53
- 235000019256 formaldehyde Nutrition 0.000 description 48
- 239000002585 base Substances 0.000 description 24
- 235000011121 sodium hydroxide Nutrition 0.000 description 23
- 239000000499 gel Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 229930040373 Paraformaldehyde Natural products 0.000 description 13
- 229920002866 paraformaldehyde Polymers 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000003518 caustics Substances 0.000 description 9
- 210000001145 finger joint Anatomy 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000003292 glue Substances 0.000 description 7
- 238000010411 cooking Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 229910021485 fumed silica Inorganic materials 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 235000014466 Douglas bleu Nutrition 0.000 description 4
- 241000758789 Juglans Species 0.000 description 4
- 235000009496 Juglans regia Nutrition 0.000 description 4
- 240000001416 Pseudotsuga menziesii Species 0.000 description 4
- 235000005386 Pseudotsuga menziesii var menziesii Nutrition 0.000 description 4
- 241000220010 Rhode Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004026 adhesive bonding Methods 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 229960000892 attapulgite Drugs 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910001410 inorganic ion Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229910052625 palygorskite Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 235000020234 walnut Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000019397 Pinus jeffreyi Species 0.000 description 3
- 235000013267 Pinus ponderosa Nutrition 0.000 description 3
- 235000013269 Pinus ponderosa var ponderosa Nutrition 0.000 description 3
- 235000013268 Pinus ponderosa var scopulorum Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 2
- ABAFKQHGFDZEJO-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptane-4-carbaldehyde Chemical compound C1C2C(C)(C)C1CCC2(C)C=O ABAFKQHGFDZEJO-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000186704 Pinales Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 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
- 241001024304 Mino Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910000831 Steel Inorganic materials 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000000506 liquid--solid chromatography Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical class OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012607 strong cation exchange resin Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 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
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31957—Wood
-
- 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
- Y10T428/4935—Impregnated naturally solid product [e.g., leather, stone, etc.]
- Y10T428/662—Wood timber product [e.g., piling, post, veneer, etc.]
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45012674A | 1974-03-11 | 1974-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050182A true CA1050182A (en) | 1979-03-06 |
Family
ID=23786869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,936A Expired CA1050182A (en) | 1974-03-11 | 1974-12-24 | Phenol-formaldehyde-resorcinol resins and adhesives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4061620A (enExample) |
| JP (1) | JPS50126729A (enExample) |
| CA (1) | CA1050182A (enExample) |
| DE (1) | DE2504326A1 (enExample) |
| FR (1) | FR2324704A1 (enExample) |
| GB (1) | GB1496703A (enExample) |
| IT (1) | IT1030104B (enExample) |
| NL (1) | NL7500965A (enExample) |
| SE (1) | SE7502663L (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070020A (en) * | 1976-07-07 | 1978-01-24 | Fansteel Inc. | Composite high strength to weight structure with fray resistance |
| SE415367B (sv) * | 1977-05-13 | 1980-09-29 | Casco Ab | Forfarande for limning med resorcinolhartslim med anvendning av en uppslamning av paraformaldehyd som herdare samt herdarkomposition for anvendning vid settet |
| DE2738267C3 (de) * | 1977-08-25 | 1986-04-17 | Hoechst Ag, 6230 Frankfurt | Verwendung von Kunstharzbindemitteln |
| US4133796A (en) * | 1977-11-17 | 1979-01-09 | Union Carbide Corporation | High temperature resistant hot melt sealant |
| US4201485A (en) * | 1978-02-21 | 1980-05-06 | Weyerhaeuser Company | Apparatus for proportioning and mixing powdered hardeners with liquid resins |
| US4376854A (en) * | 1981-04-10 | 1983-03-15 | Hodogaya Chemical Co., Ltd. | Process for preparing resorcinol copolymers |
| US4425178A (en) | 1981-11-16 | 1984-01-10 | Weyerhaeuser Company | Resin hardener and method for its use |
| SE453668B (sv) * | 1985-06-17 | 1988-02-22 | Casco Nobel Ab | Forfarande vid limning med herdande vattenbaserat lim samt for limningen avsedd hartskomponent |
| 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 |
| US4970287A (en) * | 1987-11-23 | 1990-11-13 | Olin Hunt Specialty Products Inc. | Thermally stable phenolic resin compositions with ortho, ortho methylene linkage |
| 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 |
| NL8901501A (nl) * | 1989-06-14 | 1991-01-02 | Stephanus Petrus Van Sterkenbu | Werkwijze en inrichting voor het aan elkaar lassen van uit houtachtig materiaal bestaande platen. |
| NZ260406A (en) * | 1990-12-21 | 1995-11-27 | Nz Secretary Forestry | Joining pieces of wood using a formaldehyde-based adhesive and a cure-promoter |
| US5641553A (en) * | 1993-03-24 | 1997-06-24 | Tingley; Daniel A. | Cellulose surface material adhered to a reinforcement panel for structural wood members |
| US5974760A (en) * | 1993-03-24 | 1999-11-02 | Tingley; Daniel A. | Wood I-beam with synthetic fiber reinforcement |
| US5756599A (en) * | 1993-08-17 | 1998-05-26 | Masonite Corporation | Binder resin, binder system, cellulosic composite articles, and method of making the same |
| CA2128912A1 (en) * | 1993-08-17 | 1995-02-18 | Zygmunt Teodorczyk | Modified phenol-aldehyde resin and binder system |
| US5461108A (en) * | 1993-08-31 | 1995-10-24 | Polymer Wood Processors, Inc. | Preservation of wood with phenol formaldehyde resorcinol resins |
| US5944938A (en) * | 1995-06-07 | 1999-08-31 | Weyerhaeuser Company | wood bonding method |
| US5626705A (en) * | 1995-06-07 | 1997-05-06 | Weyerhaeuser Company | Rapid setting adhesive and method of its use |
| EP0861275B1 (en) * | 1995-11-13 | 2003-02-12 | Borden Chemical, Inc. | Composition and method for curing a resorcinol resin |
| EP0889077A4 (en) * | 1996-03-22 | 2000-06-21 | Toho Rayon Kk | CARBON FIBER PREPREG FOR WOOD REINFORCEMENT, THEREFORE LAMINATED WOOD VENEER, CARBON FIBER AND WOOD VENEER CONTAINING REINFORCED WOOD COMPOSITE MATERIAL, AND WOOD REINFORCED WITH CARBON FIBER |
| US5847058A (en) * | 1996-04-05 | 1998-12-08 | Masonite Corporation | Alkylresorcinol modified phenol-aldehyde resol resin and binder system, and method of making same |
| US5912317A (en) * | 1997-04-02 | 1999-06-15 | Angus Chemical Company | Oxazolidine-based hardeners for the room temperature cure of resorcinol resins in the bonding of wood articles--II |
| EP0949309A1 (en) | 1998-04-06 | 1999-10-13 | Akzo Nobel N.V. | A method of joining surfaces |
| US6471897B1 (en) | 1998-11-04 | 2002-10-29 | Masonite Corporation | Composite article and method of making same |
| US20030024640A1 (en) * | 1999-04-30 | 2003-02-06 | Hill David A. | System and method for forming wood products |
| US8932632B2 (en) * | 2003-10-21 | 2015-01-13 | Ppg Industries Ohio, Inc. | Adhesives and sealants nanotechnology |
| US7001091B1 (en) | 2003-10-31 | 2006-02-21 | Knight Andrew F | Ink pen for dispensing ink having time-dependent characteristics |
| BRPI0817220A2 (pt) * | 2007-09-21 | 2016-05-03 | Saint Gobain Abrasifs Sa | método de formação de uma composição de resina fenólica modificada,composição de resina fenólica modificada, produto abrasivo e o método da fabricação do mesmo |
| WO2011156599A2 (en) * | 2010-06-09 | 2011-12-15 | Georgia-Pacific Chemicals Llc | Methods for producing precursor solutions and sol-gels for nano-engineered carbon materials and non-engineered carbon materials created therefrom |
| EP2397288A1 (en) * | 2010-06-14 | 2011-12-21 | Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO | A method for joining at least two elements |
| US9163169B2 (en) | 2012-03-13 | 2015-10-20 | Georgia-Pacific Chemicals Llc | Adhesive compositions having a reduced cure time and methods for making and using same |
| PL2989135T3 (pl) | 2013-04-24 | 2024-11-25 | Bakelite UK Holding Ltd. | Sposób wytwarzania żywicy typu zol-żel |
| KR101758547B1 (ko) | 2013-04-24 | 2017-07-26 | 헥시온 인코포레이티드 | 졸-겔 수지를 제조하는 방법 |
| US9683143B2 (en) * | 2014-12-24 | 2017-06-20 | United States Gypsum Company | Joint finishing adhesive |
| FR3031977B1 (fr) | 2015-01-22 | 2018-04-20 | Centre National De La Recherche Scientifique | Procede de fabrication d'une resine ablative |
| FR3031978B1 (fr) * | 2015-01-22 | 2018-04-20 | Centre National De La Recherche Scientifique | Procede de fabrication d'une resine ablative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2385373A (en) * | 1942-08-12 | 1945-09-25 | Pennsylvania Coal Products Com | Method of producing a resin and product derived therefrom |
| US2478943A (en) * | 1946-08-17 | 1949-08-16 | Koppers Co Inc | Copolymer phenolic adhesive containing the intercondensation product of a monohydric phenol and a polyhydric phenol, method of producing same, and utilization thereof |
| US2614096A (en) * | 1949-06-16 | 1952-10-14 | Borden Co | Condensation products of phenol, formaldehyde, and unsubstituted mononuclear dihydric phenols |
-
1974
- 1974-12-24 CA CA216,936A patent/CA1050182A/en not_active Expired
-
1975
- 1975-01-28 NL NL7500965A patent/NL7500965A/xx not_active Application Discontinuation
- 1975-02-03 DE DE19752504326 patent/DE2504326A1/de not_active Withdrawn
- 1975-02-07 IT IT67341/75A patent/IT1030104B/it active
- 1975-02-20 JP JP50021408A patent/JPS50126729A/ja active Pending
- 1975-03-07 FR FR7507185A patent/FR2324704A1/fr active Granted
- 1975-03-10 SE SE7502663A patent/SE7502663L/xx unknown
- 1975-03-11 GB GB10113/75A patent/GB1496703A/en not_active Expired
- 1975-09-22 US US05/615,215 patent/US4061620A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1030104B (it) | 1979-03-30 |
| FR2324704A1 (fr) | 1977-04-15 |
| JPS50126729A (enExample) | 1975-10-06 |
| GB1496703A (en) | 1977-12-30 |
| DE2504326A1 (de) | 1975-09-18 |
| SE7502663L (sv) | 1975-09-12 |
| NL7500965A (nl) | 1975-09-15 |
| US4061620A (en) | 1977-12-06 |
| FR2324704B1 (enExample) | 1979-08-24 |
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