CA1330604C - Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement - Google Patents

Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement

Info

Publication number: CA1330604C
Authority: CA; Canada
Prior art keywords: curing agent; binder composition; resin solution; resin; phenol
Prior art date: 1987-09-30
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 - Fee Related

Application number

CA 567126

Other languages

English (en)

Inventor

Richard D. Stratton

David A. Perry

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.)

Hexion Inc

Original Assignee

Perkins Industries Inc

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.)

1987-09-30

Filing date

1988-05-18

Publication date

1994-07-05

1988-05-18 Application filed by Perkins Industries Inc filed Critical Perkins Industries Inc

1994-07-05 Application granted granted Critical

1994-07-05 Publication of CA1330604C publication Critical patent/CA1330604C/fr

2011-07-05 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 157
239000011230 binding agent Substances 0.000 title claims abstract description 96
239000003795 chemical substances by application Substances 0.000 title claims abstract description 94
230000002708 enhancing effect Effects 0.000 title abstract description 6
238000000034 method Methods 0.000 claims abstract description 52
238000001879 gelation Methods 0.000 claims abstract description 12
238000013019 agitation Methods 0.000 claims abstract description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 109
239000000243 solution Substances 0.000 claims description 74
229920001568 phenolic resin Polymers 0.000 claims description 66
229920005989 resin Polymers 0.000 claims description 65
239000011347 resin Substances 0.000 claims description 65
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 61
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 49
239000005011 phenolic resin Substances 0.000 claims description 43
239000007787 solid Substances 0.000 claims description 43
239000007788 liquid Substances 0.000 claims description 37
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 32
239000002023 wood Substances 0.000 claims description 28
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
239000000499 gel Substances 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 21
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 20
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 20
239000011120 plywood Substances 0.000 claims description 18
239000012978 lignocellulosic material Substances 0.000 claims description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
230000015572 biosynthetic process Effects 0.000 claims description 11
239000000084 colloidal system Substances 0.000 claims description 11
150000002148 esters Chemical group 0.000 claims description 9
239000001087 glyceryl triacetate Substances 0.000 claims description 9
235000013773 glyceryl triacetate Nutrition 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 9
229960002622 triacetin Drugs 0.000 claims description 9
150000002596 lactones Chemical class 0.000 claims description 8
239000004576 sand Substances 0.000 claims description 8
230000009257 reactivity Effects 0.000 claims description 7
239000011819 refractory material Substances 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
150000005677 organic carbonates Chemical class 0.000 claims description 4
239000002245 particle Substances 0.000 claims description 4
229910052845 zircon Inorganic materials 0.000 claims description 4
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 claims description 4
229920002522 Wood fibre Polymers 0.000 claims description 3
150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
238000003786 synthesis reaction Methods 0.000 claims description 3
239000002025 wood fiber Substances 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000000395 magnesium oxide Substances 0.000 claims description 2
229910052609 olivine Inorganic materials 0.000 claims description 2
239000010450 olivine Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000010453 quartz Substances 0.000 claims description 2
239000000377 silicon dioxide Substances 0.000 claims description 2
238000002347 injection Methods 0.000 claims 8
239000007924 injection Substances 0.000 claims 8
239000003513 alkali Substances 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 2
239000007859 condensation product Substances 0.000 claims 1
239000007858 starting material Substances 0.000 abstract description 3
239000006185 dispersion Substances 0.000 abstract description 2
235000011121 sodium hydroxide Nutrition 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 19
239000000853 adhesive Substances 0.000 description 16
230000001070 adhesive effect Effects 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
230000005484 gravity Effects 0.000 description 12
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
239000004202 carbamide Substances 0.000 description 10
238000003860 storage Methods 0.000 description 9
239000003292 glue Substances 0.000 description 8
230000000717 retained effect Effects 0.000 description 8
238000001816 cooling Methods 0.000 description 7
229920002261 Corn starch Polymers 0.000 description 6
239000004606 Fillers/Extenders Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
229940099112 cornstarch Drugs 0.000 description 6
239000000463 material Substances 0.000 description 5
235000011118 potassium hydroxide Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000835 fiber Substances 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000004026 adhesive bonding Methods 0.000 description 3
239000000919 ceramic Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000011094 fiberboard Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
-1 particleboard Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920003987 resole Polymers 0.000 description 3
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000006260 foam Substances 0.000 description 2
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
239000013505 freshwater Substances 0.000 description 2
238000007731 hot pressing Methods 0.000 description 2
230000007774 longterm Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000843 powder Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
235000012431 wafers Nutrition 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
229940035437 1,3-propanediol Drugs 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
NYBXFCLDEATPCM-UHFFFAOYSA-N 3-methyloxetan-2-one Chemical compound CC1COC1=O NYBXFCLDEATPCM-UHFFFAOYSA-N 0.000 description 1
JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-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
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 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
150000007513 acids Chemical class 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
WZRZKFUVOSDSBQ-UHFFFAOYSA-N butane-1,2-diol;carbonic acid Chemical compound OC(O)=O.CCC(O)CO WZRZKFUVOSDSBQ-UHFFFAOYSA-N 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
ANQJWUKLNGHYIP-UHFFFAOYSA-N butane-1,3-diol;carbonic acid Chemical compound OC(O)=O.CC(O)CCO ANQJWUKLNGHYIP-UHFFFAOYSA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
CHYOCNJYMLMTNE-UHFFFAOYSA-N carbonic acid;pentane-1,2-diol Chemical compound OC(O)=O.CCCC(O)CO CHYOCNJYMLMTNE-UHFFFAOYSA-N 0.000 description 1
MEYBCCDNSNEEGP-UHFFFAOYSA-N carbonic acid;pentane-1,3-diol Chemical compound OC(O)=O.CCC(O)CCO MEYBCCDNSNEEGP-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000306 component Substances 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
235000012254 magnesium hydroxide Nutrition 0.000 description 1
RSDDIXBRSNNUJI-WPMUBMLPSA-N methyl 2-methyl-2-[[(2s)-4-methyl-2-[[(2s)-2-[[(2s)-3-methyl-2-[[2-methyl-2-[[(2s)-4-methyl-2-[[(2s)-2-[[(2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]propanoyl]amino]pentanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]p Chemical compound COC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)(C)C RSDDIXBRSNNUJI-WPMUBMLPSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000000123 paper Substances 0.000 description 1
RKHQZMOCQHXUBC-UHFFFAOYSA-N phenol;potassium Chemical compound [K].OC1=CC=CC=C1 RKHQZMOCQHXUBC-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
239000002964 rayon Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
108010056596 t-butyloxycarbonyl-valyl-alanyl-leucyl-2-aminoisobutyryl-valyl-alanyl-leucyl-2-aminoisobutyryl methyl ester Proteins 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)
Phenolic Resins Or Amino Resins (AREA)

CA 567126 1987-09-30 1988-05-18 Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement Expired - Fee Related CA1330604C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US102,665		1979-12-12
US10266587A	1987-09-30	1987-09-30

Publications (1)

Publication Number	Publication Date
CA1330604C true CA1330604C (fr)	1994-07-05

Family

ID=22291026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 567126 Expired - Fee Related CA1330604C (fr)	1987-09-30	1988-05-18	Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement

Country Status (4)

Country	Link
JP (1)	JP2785912B2 (fr)
AU (1)	AU600601B2 (fr)
CA (1)	CA1330604C (fr)
PH (1)	PH26826A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1037314C2 (nl) *	2009-09-23	2011-03-28	Jakob Gerrit Hendrik Pannekoek	Olivijn coating.
CN119566216A (zh) *	2024-11-19	2025-03-07	沈阳工业大学	无机粘结剂砂硬化工艺方法及应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19854207A1 (de)	1998-11-24	2000-05-25	Wacker Chemie Gmbh	Verfahren zur Herstellung von schnellhärtenden, mit Phenolharz gebundenen Formkörpern

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU553707B2 (en) *	1982-04-27	1986-07-24	Borden (Uk) Limited	Impregnated filter paper
EP0259042A3 (fr) *	1986-09-03	1989-01-25	Borden, Inc.	Procédé pour lier des matériaux lignocellulosiques
US4758478A (en) *	1986-09-30	1988-07-19	Daisy Nick K	Fast curing phenolic resins and bonding methods employing same

1988
- 1988-05-18 CA CA 567126 patent/CA1330604C/fr not_active Expired - Fee Related
- 1988-07-04 PH PH37170A patent/PH26826A/en unknown
- 1988-09-29 JP JP63242623A patent/JP2785912B2/ja not_active Expired - Lifetime
- 1988-09-29 AU AU22974/88A patent/AU600601B2/en not_active Ceased

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1037314C2 (nl) *	2009-09-23	2011-03-28	Jakob Gerrit Hendrik Pannekoek	Olivijn coating.
CN119566216A (zh) *	2024-11-19	2025-03-07	沈阳工业大学	无机粘结剂砂硬化工艺方法及应用

Also Published As

Publication number	Publication date
AU600601B2 (en)	1990-08-16
AU2297488A (en)	1989-04-06
PH26826A (en)	1992-11-05
JP2785912B2 (ja)	1998-08-13
JPH01132650A (ja)	1989-05-25

Legal Events

Date	Code	Title	Description
2004-07-05	MKLA	Lapsed

Publication	Publication Date	Title
El Mansouri et al.	2007	Lignin-based wood panel adhesives without formaldehyde
CA1301040C (fr)	1992-05-19	Resines phenoliques a cuisson rapide
CA2439362C (fr)	2009-04-28	Composition adhesive d'alcool furfurylique et de lignine
US4098770A (en)	1978-07-04	Spray-dried phenolic adhesives
US5684114A (en)	1997-11-04	Cross-catalyzed phenol-resorcinol adhesive
AU605504B2 (en)	1991-01-17	Process for the preparation of urea-formaldehyde resins
US6297313B1 (en)	2001-10-02	Adhesive systems and products formed using same and methods for producing said adhesive systems and products
CA3036131A1 (fr)	2018-03-15	Compositions de lignine glyoxalee
AU2011243020B2 (en)	2014-11-27	Bonding wood composites with resin solids-fortified phenol-formaldehyde resin
US5364902A (en)	1994-11-15	Resorcinol-glutaraldehyde resin as an accelerator for curing phenol-formaldehyde resins
US4082903A (en)	1978-04-04	Tree foliage extenders and fillers for wood adhesives
US4968773A (en)	1990-11-06	Process for the preparation of urea-formaldehyde resins
US3793113A (en)	1974-02-19	Adhesive compositions and method of making plywood
WO1990015834A1 (fr)	1990-12-27	Composition liante pour materiaux fibreux et/ou du type agglomeres
CA1330604C (fr)	1994-07-05	Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement
US5763559A (en)	1998-06-09	Phenol-formaldehyde resins modified with guanidine salts
AU631722B2 (en)	1992-12-03	Glutaraldehyde resin binding system for manufacture of wood products
EP0259042A2 (fr)	1988-03-09	Procédé pour lier des matériaux lignocellulosiques
US3681168A (en)	1972-08-01	Bonding with vinyl acetate polymer modified resorcinol-base adhesive
RU1775436C (ru)	1992-11-15	Полимерное св зующее дл древесно-стружечных плит
CN101517023A (zh)	2009-08-26	用于树脂系木胶的组合物及方法

CA1330604C - Compositions de liant pouvant etre durcies, contenant des adjuvants de durcissement - Google Patents

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