CA1083163A - Method for producing a liquid resin - Google Patents

Method for producing a liquid resin

Info

Publication number: CA1083163A
Authority: CA; Canada
Prior art keywords: furan; contacting; formaldehyde; takes place; reaction
Prior art date: 1976-01-02
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

CA266,735A

Other languages

English (en)

French (fr)

Inventor

Andrew P. Dunlop

Rudy F. Macander

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.)

Quaker Oats Co

Original Assignee

Quaker Oats Co

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.)

1976-01-02

Filing date

1976-11-29

Publication date

1980-08-05

1976-11-29 Application filed by Quaker Oats Co filed Critical Quaker Oats Co

1980-08-05 Application granted granted Critical

1980-08-05 Publication of CA1083163A publication Critical patent/CA1083163A/en

Status Expired legal-status Critical Current

Links

239000007788 liquid Substances 0.000 title claims abstract description 19
238000004519 manufacturing process Methods 0.000 title claims abstract description 13
239000011347 resin Substances 0.000 title claims description 37
229920005989 resin Polymers 0.000 title claims description 37
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 143
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 88
238000000034 method Methods 0.000 claims abstract description 31
239000003377 acid catalyst Substances 0.000 claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims description 51
239000011541 reaction mixture Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 4
125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 3
239000012260 resinous material Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
125000004181 carboxyalkyl group Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical class 0.000 claims description 2
239000007859 condensation product Substances 0.000 abstract description 9
239000002131 composite material Substances 0.000 abstract description 5
239000011230 binding agent Substances 0.000 abstract description 4
239000003607 modifier Substances 0.000 abstract 1
229960004279 formaldehyde Drugs 0.000 description 41
235000019256 formaldehyde Nutrition 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 30
239000003054 catalyst Substances 0.000 description 27
239000004615 ingredient Substances 0.000 description 18
239000002253 acid Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 11
229940073584 methylene chloride Drugs 0.000 description 11
239000000203 mixture Substances 0.000 description 11
235000006408 oxalic acid Nutrition 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
150000007513 acids Chemical class 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
-1 for example Chemical class 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 6
239000000376 reactant Substances 0.000 description 6
229920002866 paraformaldehyde Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
238000006482 condensation reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002240 furans Chemical class 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VQKFNUFAXTZWDK-UHFFFAOYSA-N alpha-methylfuran Natural products CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
239000004576 sand Substances 0.000 description 3
241000894007 species Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
NUAMBIFNOYDDRT-UHFFFAOYSA-N 3,4-dipropylfuran Chemical class CCCC1=COC=C1CCC NUAMBIFNOYDDRT-UHFFFAOYSA-N 0.000 description 2
RPCHNECSJGMRGP-UHFFFAOYSA-N 3-Ethylfuran Chemical compound CCC=1C=COC=1 RPCHNECSJGMRGP-UHFFFAOYSA-N 0.000 description 2
BNANPEQZOWHZKY-UHFFFAOYSA-N 3-phenylfuran Chemical compound O1C=CC(C=2C=CC=CC=2)=C1 BNANPEQZOWHZKY-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
241000193803 Therea Species 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
UPSIAUXDGWYOFJ-UHFFFAOYSA-N formaldehyde;furan Chemical compound O=C.C=1C=COC=1 UPSIAUXDGWYOFJ-UHFFFAOYSA-N 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
AFOPCURQYRRFRQ-UHFFFAOYSA-N 2-(Propan-2-yl)furan Chemical compound CC(C)C1=CC=CO1 AFOPCURQYRRFRQ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
DQFQVZMTFWQXDN-UHFFFAOYSA-N 3,4-di(propan-2-yl)furan Chemical compound CC(C)C1=COC=C1C(C)C DQFQVZMTFWQXDN-UHFFFAOYSA-N 0.000 description 1
HYZRWEIHMXDIMR-UHFFFAOYSA-N 3-(4-chlorophenyl)furan Chemical compound C1=CC(Cl)=CC=C1C1=COC=C1 HYZRWEIHMXDIMR-UHFFFAOYSA-N 0.000 description 1
PCWCERNFIYTAIK-UHFFFAOYSA-N 3-(4-methylphenyl)furan Chemical compound C1=CC(C)=CC=C1C1=COC=C1 PCWCERNFIYTAIK-UHFFFAOYSA-N 0.000 description 1
CSKLZCCRTYMTMN-UHFFFAOYSA-N 3-(4-nonylphenyl)furan Chemical compound C1=CC(CCCCCCCCC)=CC=C1C1=COC=C1 CSKLZCCRTYMTMN-UHFFFAOYSA-N 0.000 description 1
STBHXKUUJQCHCR-UHFFFAOYSA-N 3-butyl-4-methylfuran Chemical class CCCCC1=COC=C1C STBHXKUUJQCHCR-UHFFFAOYSA-N 0.000 description 1
JPPBBGANXNRTBE-UHFFFAOYSA-N 3-chlorofuran Chemical compound ClC=1C=COC=1 JPPBBGANXNRTBE-UHFFFAOYSA-N 0.000 description 1
BNTHOWSSXWKNQM-UHFFFAOYSA-N 3-decylfuran Chemical compound CCCCCCCCCCC=1C=COC=1 BNTHOWSSXWKNQM-UHFFFAOYSA-N 0.000 description 1
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 1
DBEUDJPCVGLVKG-UHFFFAOYSA-N 3-hexylfuran Chemical compound CCCCCCC=1C=COC=1 DBEUDJPCVGLVKG-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000861718 Chloris <Aves> Species 0.000 description 1
YHGNXEIQSHICNK-UHFFFAOYSA-N Di-2-furanylmethane Chemical compound C=1C=COC=1CC1=CC=CO1 YHGNXEIQSHICNK-UHFFFAOYSA-N 0.000 description 1
229910015400 FeC13 Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
239000000306 component Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
239000007849 furan resin Substances 0.000 description 1
STJIISDMSMJQQK-UHFFFAOYSA-N furan-3-ylmethanol Chemical compound OCC=1C=COC=1 STJIISDMSMJQQK-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ZCXOSDRICFIHTA-UHFFFAOYSA-N n-methylaniline;hydrochloride Chemical compound [Cl-].C[NH2+]C1=CC=CC=C1 ZCXOSDRICFIHTA-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920013730 reactive polymer Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000009736 wetting Methods 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0256—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing oxygen in the ring

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Phenolic Resins Or Amino Resins (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pens And Brushes (AREA)

CA266,735A 1976-01-02 1976-11-29 Method for producing a liquid resin Expired CA1083163A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US646,193		1976-01-02
US05/646,193 US4017461A (en)	1976-01-02	1976-01-02	Method for manufacturing liquid resinous furan-formaldehyde condensation products

Publications (1)

Publication Number	Publication Date
CA1083163A true CA1083163A (en)	1980-08-05

Family

ID=24592141

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA266,735A Expired CA1083163A (en)	1976-01-02	1976-11-29	Method for producing a liquid resin

Country Status (12)

Country	Link
US (1)	US4017461A (2)
JP (1)	JPS5285291A (2)
BE (1)	BE849322A (2)
CA (1)	CA1083163A (2)
DE (1)	DE2658015A1 (2)
DK (1)	DK568776A (2)
ES (1)	ES454216A1 (2)
FR (1)	FR2337151A1 (2)
GB (1)	GB1529906A (2)
NL (1)	NL7614172A (2)
NO (1)	NO764137L (2)
SE (1)	SE7613763L (2)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4083817A (en) *	1977-06-15	1978-04-11	The Quaker Oats Company	Blends of furan-aldehyde resins with phenolic resins and molded articles produced therefrom
US4178429A (en) *	1978-11-17	1979-12-11	Scheffer Karl D	Catalyst for curing resins
US4316935A (en) *	1979-03-12	1982-02-23	The Celotex Corporation	Polyisocyanurate foam and laminates thereof and process for producing them
US4516996A (en) *	1983-04-07	1985-05-14	Owens-Corning Fiberglas Corporation	Formation of molded glass fiber parts from glass fiber blankets and product
US4791022A (en) *	1983-11-07	1988-12-13	Owens-Corning Fiberglas Corporation	Decorative panels
US6077883A (en) *	1992-05-19	2000-06-20	Johns Manville International, Inc.	Emulsified furan resin based glass fiber binding compositions, process of binding glass fibers, and glass fiber compositions
US5534612A (en) *	1992-05-19	1996-07-09	Schuller International, Inc.	Glass fiber binding compositions, process of making glass fiber binding compositions, process of binding glass fibers, and glass fiber compositions
JPH07506604A (ja) *	1992-05-19	1995-07-20	シュラー　インターナショナル　インコーポレーテッド	ガラス繊維結合組成物，ガラス繊維の結合方法，並びにガラス繊維組成物
US5459183A (en) *	1993-05-19	1995-10-17	Schuller International, Inc.	Low VOC furan resins and method of reducing VOCS in furan resins
US5491180A (en) *	1994-08-17	1996-02-13	Kao Corporation	Binder composition for mold making, binder/curing agent composition for mold making, sand composition for mold making, and process of making mold
DE69535397T2 (de) *	1994-08-19	2007-10-31	Kao Corp.	Binderzusammensetzung und herstellungsverfahren für formen
JP5986457B2 (ja) *	2011-08-31	2016-09-06	花王株式会社	自硬性鋳型造型用粘結剤組成物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2306924A (en) *	1938-02-17	1942-12-29	Gen Aniline & Film Corp	Hard infusible resinous condensation products
US2343972A (en) *	1943-02-24	1944-03-14	Harvel Res Corp	Novel furfuryl alcohol-formaldehyde acid condensation resinous product and method for preparing the same
US2450108A (en) *	1944-12-11	1948-09-28	Ici Ltd	Production of heterocyclic compounds
US2486392A (en) *	1945-10-10	1949-11-01	Quaker Oats Co	Alkylfuran resins and method of making same
US2601497A (en) *	1950-01-14	1952-06-24	Quaker Oats Co	Furfuryl alcohol resins
US2830971A (en) *	1953-07-29	1958-04-15	Quaker Oats Co	Artificial resin from furfuryl alcohol, formaldehyde, and boric acid, and process ofmaking the same

1976
- 1976-01-02 US US05/646,193 patent/US4017461A/en not_active Expired - Lifetime
- 1976-11-23 GB GB48837/76A patent/GB1529906A/en not_active Expired
- 1976-11-29 CA CA266,735A patent/CA1083163A/en not_active Expired
- 1976-12-03 NO NO764137A patent/NO764137L/no unknown
- 1976-12-07 SE SE7613763A patent/SE7613763L/xx unknown
- 1976-12-10 FR FR7637292A patent/FR2337151A1/fr active Granted
- 1976-12-10 BE BE1007816A patent/BE849322A/xx not_active IP Right Cessation
- 1976-12-14 ES ES454216A patent/ES454216A1/es not_active Expired
- 1976-12-17 DE DE19762658015 patent/DE2658015A1/de not_active Ceased
- 1976-12-17 DK DK568776A patent/DK568776A/da unknown
- 1976-12-20 NL NL7614172A patent/NL7614172A/xx not_active Application Discontinuation
- 1976-12-20 JP JP15328076A patent/JPS5285291A/ja active Pending

Also Published As

Publication number	Publication date
ES454216A1 (es)	1977-11-16
NO764137L (no)	1977-07-05
DE2658015A1 (de)	1977-07-14
FR2337151B1 (2)	1981-07-03
DK568776A (da)	1977-07-03
FR2337151A1 (fr)	1977-07-29
NL7614172A (nl)	1977-07-05
GB1529906A (en)	1978-10-25
JPS5285291A (en)	1977-07-15
BE849322A (fr)	1977-06-10
US4017461A (en)	1977-04-12
SE7613763L (sv)	1977-07-03

Legal Events

Date	Code	Title	Description
1997-08-05	MKEX	Expiry

Publication	Publication Date	Title
CA1083163A (en)	1980-08-05	Method for producing a liquid resin
DE1720204C3 (de)	1983-11-24	Verfahren zur Herstellung von Phenol-Formaldehyd-Kondensaten und ihre Verwendung als Bindemittel und in Formmassen
EP0480687B1 (en)	1996-05-08	Phenolic resin alkoxylates
US3332911A (en)	1967-07-25	Production of fast-curing phenol-aldehyde novolac resins employing a boric acid or borate salt catalyst
US4140845A (en)	1979-02-20	Control of procedures for formation of water-immiscible thermosetting phenol-formaldehyde resins
IL108362A (en)	1998-12-27	Liquid resinous binder compositions of furfuryl alcohol and formaldehyde and their preparation
US4634723A (en)	1987-01-06	Furfuryl alcohol binders, methods for their production and use
EP0539098B1 (en)	1998-07-01	Process for hardening phenolic resins
DE2010532C3 (de)	1979-07-19	Verfahren zur Herstellung von Furfurylalkohol-Formaldehyd-VorpoIykondensaten und ihre Verwendung
DE1570958B2 (de)	1979-01-04	Latent härtbare Harzmasse
DE3028974A1 (de)	1981-04-23	Verfahren zur herstellung von phenol-formaldehyd-furfurylalkohol-terpolymerisaten
US4297473A (en)	1981-10-27	Quick-curing phenolic resin and process for preparing same
US4055528A (en)	1977-10-25	Phenol-formaldehyde resin for foundry applications
DE2738417C2 (de)	1983-01-13	Sulfonsäuremodifizierte Phenol-Aldehyd-Kondensate
US4132699A (en)	1979-01-02	Phenol formaldehyde resins, their manufacture and use
US5849858A (en)	1998-12-15	Resinous binder compositions
DE2356703C2 (de)	1984-10-31	Bindemittel und ihre Verwendung zur Herstellung von Giessereiformen und -kernen
US4299947A (en)	1981-11-10	Process for producing quick-curing phenolic resin
EP0780418A2 (de)	1997-06-25	Triamine und ein Verfahren zu ihrer Herstellung
JPS63101038A (ja)	1988-05-06	シエルモ−ルド用樹脂被覆砂粒の製造方法
SU696013A1 (ru)	1979-11-05	Способ получени -замещенных цианакрилатов
US2617832A (en)	1952-11-11	Method for preparing diphenylol methane
DE1720825C3 (de)	1975-10-02	Einstufenverfahren zur Herstellung von hitzehärtenden harzartigen Einstufen-Kondensationsprodukten aus Aldehyd und Polyphenol/Phenol
US4184032A (en)	1980-01-15	Control of procedures for formation of water-immiscible thermosetting phenol-formaldehyde resins
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