GB2120263A - A process for curing acid-curable abrasive compositions - Google Patents
A process for curing acid-curable abrasive compositions Download PDFInfo
- Publication number
- GB2120263A GB2120263A GB08313057A GB8313057A GB2120263A GB 2120263 A GB2120263 A GB 2120263A GB 08313057 A GB08313057 A GB 08313057A GB 8313057 A GB8313057 A GB 8313057A GB 2120263 A GB2120263 A GB 2120263A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- substituted
- unsubstituted
- curing
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 239000011230 binding agent Substances 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- 239000003082 abrasive agent Substances 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 5
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 3
- -1 C1-Clz-alkyl Chemical group 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 229920001568 phenolic resin Polymers 0.000 claims description 14
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical group [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229920003987 resole Polymers 0.000 claims description 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 5
- 239000012876 carrier material Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 229920003180 amino resin Polymers 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 6
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000010431 corundum Substances 0.000 description 9
- 229910052593 corundum Inorganic materials 0.000 description 9
- 239000006061 abrasive grain Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000945 filler Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000004411 aluminium Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 238000004873 anchoring Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QWQOVDZSKARFDU-UHFFFAOYSA-N (2-oxo-4-phenyl-1,3,2-dioxathiolan-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(OS(OC1)=O)C1=CC=CC=C1 QWQOVDZSKARFDU-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052580 B4C Inorganic materials 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- INAHAJYZKVIDIZ-UHFFFAOYSA-N boron carbide Chemical compound B12B3B4C32B41 INAHAJYZKVIDIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 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
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229910001610 cryolite Inorganic materials 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
- B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
- B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
- B24D3/20—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent and being essentially organic
- B24D3/28—Resins or natural or synthetic macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B24—GRINDING; POLISHING
- B24D—TOOLS FOR GRINDING, BUFFING OR SHARPENING
- B24D3/00—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents
- B24D3/02—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent
- B24D3/20—Physical features of abrasive bodies, or sheets, e.g. abrasive surfaces of special nature; Abrasive bodies or sheets characterised by their constituents the constituent being used as bonding agent and being essentially organic
- B24D3/28—Resins or natural or synthetic macromolecular compounds
- B24D3/285—Reaction products obtained from aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
A process for curing abrasive compositions containing an acid- curable binder and, as curing catalyst, an organic sulfonic acid releasable by the action of light, and also additives customarily used in abrasives technology, in which process the abrasive compositions after drying are exposed to the action of light rays and thus cured. Of particular interest as masked curing catalysts are organic compounds of the formulae I and II <IMAGE> wherein n and R1 to R8 have the meanings given in Claim 4.g
Description
SPECIFICATION
A process for curing acid-curable abrasive compositions
The present invention relates to a process for curing acid-curable abrasive compositions based on an acid-curable resin containing a masked curing catalyst.
By a grinding tool is meant in general the combination of a hard granular abrasive, optionally also of a carrier element or reinforcement, with a binder to form a closed composite material.
Grinding tools can be classified, according to typical structural features, under two main groups, namely, grinding wheels or disks, such as abrasive wheels, rings or points, and flexible abrasives on flat or sheetiike carrier materials.
In the case of flexible abrasives on flat carrier materials, there are used as binders the most varied synthetic resins, including however to the greater extent the pheno- and aminoplasts, and also the alkyd-melamine resins.
To produce these abrasives, the carrier material is coated with a thin film of a liquid base binder and the abrasive grain; the binder is then dried, and subsequently cured by heat treatment to such a degree that the abrasive grain is sufficiently anchored so as not to become displaced or turned over during further treatment. A final covering binder layer, which is usually filled with calcium carbonate, is afterwards applied, and is likewise cured by being subjected to a a heat treatment, the two operations taking several hours to perform.The reason for this considerable amount of drying and curing time being required is in particular the fact that the binders used are in most cases in the form of aqueous dispersions, so that firstly the dispersion water has to be removed in the drying operation, and that, especially with the use of phenol-formaldehyde resins as binders, a further amount of water is released on curing, and consequently this also has to be removed. Furthermore, high temperatures are necessary for curing.
The use of acid curing catalysts to accelerate the curing of acid-curable resins is indeed known, including for example organic acids such as p-toluenesulfonic acid (cp. in this connection Houben-Weyl, Methoden der organischen Chemie (Methods in organic Chemistry), Vol. 14/2, 4th Edition (1963), p.238, or German Patent
Specification No. 2,406,992). For the production of abrasive compositions based on acid-curable binders, the use of such acids as catalysts to accelerate the curing stage is however not possible, since acids of this type effect already during the drying phase premature curing of the resin. This leads to undesirable bubble formation which is caused by the water or condensation product entrapped by the resin.
To accelerate the drying and curing process, there has also been suggested, in the German
Offenlegungsschrift No. 2,444,525, a process for producing abrasive compositions, in which phenol-resol binders in polar organic solvents are used in place of the customary aqueous binders. This process does not however satisfy in all respects the demands made.
It has now been found that with specific, so-called masked catalysts, which as a result of exposure to light rays during the curing stage are rapidly degraded with the formation of free sulfonic acids, the curing process can be considerably accelerated and shortened. Curing can moreover be carried out at a lower temperature.
The essential advantage of curing catalysts of the said type is that, as inactive compounds during the drying stage, they effect no undesirable premature curing of the binder. By virtue of this factor, the use of acid catalysis for the curing of abrasive compositions is for the first time rendered possible.
Subject matter of the present invention is accordingly a process for curing abrasive compositions containing an acid-curable binder and, as curing catalyst, an organic sulfonic acid releasable by the action of light, in which process the abrasive compositions after drying are exposed to the action of light rays and thus cured.
Of particular interest as masked curing catalysts are organic compounds of the formulae I and II
wherein n is 1 or2, R1 is phenyl or naphthyl which is unsubstituted or substituted for example by 1,2 or 3 radicals: -Cl, -Br,
-CN, - NO2, C1-C12-alkyl, C1-C4-alkoxy, phenyloxy, tolyloxy, phenylthio, tolylthio, C1-C8-alkylthio, -SCH2CH2OH, C1-C4-alkylsulfonyl, phenylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C4
dialkylamino, phenyl-CONH- or C1-C4-alkyl-CONH-, or by benzoyl, or
R1 is anthryl, phenanthryl, thienyl, pyridyl, furyl, indolyl or tetrahydronaphthyl, and
R2 and Rg independently of one another are each hydrogen, or C1-C8-alkyl which is unsubstituted or
substituted for example by -OH, -Cl, C1-C4-alkoxy, -CN, C2-C5-alkoxcarbonyl, phenyl, chlorophenyl,
C7-C10-alkylphenyl or C7-C10-alkoxyphenyl, or they are benzoyl, in addition
R3 is phenyl which is unsubstituted or substituted for example by -Cl, C1-C4-alkyl, C1-C4-alkoxy or
C1-C4-alkylthio, or it is C2-C8-alkoxycarbonyl, -CN, C1-C4-alkyl-NH-CO-, phenyl-NH-CO-or-CONH2, or
R2 and R3 together with the carbon atom to which they are bound form a C4-C6-cycloalkyl ring,
R4 is, when n = 1, C1-C18-alkyl, phenyl which is unsubstituted or substituted for example by halogen,
C1-C12-alkyl, C1-C4-alkoxy, C1-C4-alkyl-CONH-, phenyl-CONH-, -NO2 or benzoyl, or it is naphthyl which
is unsubstituted or substituted for example by halogen, C1-C12-alkyl or C1-C4-alkoxy, or it is
C5-C6-cycloalkyl, C7-C9-aralkyl, campheryl, -CF3, -CCI3, -F or -NH2, and
R4 is, when n = 2, a -(CH2)m group, wherein m is 2 to 8, or phenylene or naphthylene each unsubstituted
or substituted for example by C1-C12-alkyl, B5 is phenyl or naphthyl which are each unsubstituted or substituted by 1,2 or 3 radicals: -Cl, -Br, C1-C12-alkyl, phenyl, C1-C4-alkoxy, phenyloxy, benzyloxy, C1-C8-alkylthio, phenylthio, -SCH2CH2OH,
C1-C4-alkyl-CONH-, benzoylamino or dimethylamino, or by benzoyl, or B5 is anthryi or phenanthryl,
R6 is hydrogen, -OH, C1-C4-alkoxy, -OSi(CH3)3, -OCOCH3, or C1-C8-alkyl which is unsubstituted or
substituted by phenyl,
R7 is hydrogen, or C1-C8-alkyl which is unsubstituted or substituted by phenyl, or R7 is -CN, benzoyl,
C1-C4-alkylcarbonyl, C2-C5-alkoxycarbonyl or phenyl, B8 is hydrogen, C1-C8-alkyl which is unsubstituted or substituted by -OH, -Cl or phenyl, or it is phenyl
which is unsubstituted or substituted by -OH, -Cl, C1-C4-alkyl or C1-C4-alkoxy, or B8 is C2-C6-alkenyl, C8-Cg-phenylalkenyl, furyl, thienyl or -CCI3, or saturated or unsaturated C5-C6-cycloalkyl, and
moreover B5 with R7, R7 with B8 or B6 with R7, together with the carbon structure to which they are bound, form a 5
or 6-membered ring which contains 1 to 5: -CH2-, -CH(CH3)-, -C(CH3)2-, -0--S-, -SO-,
-SO2-, -CO-, -N(CO-C1-C4-alkyl)- or -N(COC6H5)- groups.
When phenyl and naphthyl, as B, and R5, are substituted by C1-C12-alkyl, they are straight-chain or branched-chain substituents, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or dodecyl, especially however methyl. If phenyl and naphthyl, as R1 and R5, are substituted by C1-C4-alkoxy, they are for example methoxy, ethoxy, propoxy or tert-butoxy.
When phenyl and naphthyl, as R1 and R5, are substituted by C1-C8-alkylthio,they are straight-chain or branched-chain substituents, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl,tert-butyl, pentyl, hexyl, heptyl or octyl, particularly methylthio.
If R1 is a phenyl or naphthyl substituted by C1-C4-alkylamino or CrC4-dialkylamino, it is for example a methyl-, ethyl-, propyl- or n-butylamino group, or a do methyl or diethylamino substitution group.
When phenyl or naphthyl as R1 is substituted by C1-C4-alkylsulfonyl, it is for example methyl-, ethyl-, propyl-, butyl- ortert-butylsulfonyl.
When phenyl or naphthyl denoted by R1 is substituted by C1-C4-alkyl-CONH-, the substituents are for example methyl-, ethyl-, propyl- or n-butyl-CONH-. If phenyl as R4 contains C1-C4-alkyl-CONH-, the
substituents are for example methyl-, ethyl-, propyl- or n-butyl-CONH-.
Where R1 is thienyl, pyridyl, furyl, indolyl or tetrahydronaphthyl, all position isomers come into
consideration. Preferred position isomers are however: 2-thienyl, 3-pyridyl, 2-furyl, 3-indolyl or 1,2,3,4
tetrahydro-6-naphthyl.
As C-C8-alkyl, R2, R3, B6 and R8 are straight-chain or branched-chain alkyl groups, preferably however straight-chain C1-C4-alkyl groups, for example methyl, ethyl, n-propyl or n-butyl.
When C1-C8-alkyl in the case of B2 and R3, and phenyl or naphthyl in the case of R4, are substituted by C,-C4-alkoxy, and if B6 is C1-C4-alkoxy, they are for example methoxy, ethoxy, propoxy or tert-butoxy substituents.
When C1-C8-alkyl, as R2 and R3, is substituted by C7-C10-alkylphenyl or C7-C0-alkoxyphenyl, the substituents are for example methyl-, methoxy-, ethyl-, ethoxy-, tert-butyl- ortert-butoxyphenyl.
If alkyl as B3 is substituted by C1-C4-alkylthio, the substituents are for example methyl-, ethyl-, propyl- and tert-butylthio.
When R2 and B3 together with the C atom to which they are bound form a C4-C6-cycloalkyl ring, it is for example a cyclopentane, cyclohexane or cycloheptane ring, in particular however a cyclohexane ring.
When R4, if n = 1, is C1-C18-alkyl, it is a straight-chain or branched-chain group, such as: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, 2-ethylhexyl, undecyl, dodecyl, tert-dodecyl, tridecyl, tetradecyl, hexadecyl or octadecyl.
When phenyl or naphthyl as R4 is substituted by C1-C12-alkyl, it is a straight-chain or branched-chain alkyl group.
Where R4 is C5-C8-cycloalkyl, it is cyclopentyl and cyclohexyl.
If R4 is C7-Cg-aralkyl, it is for example 1 -phenylethyl, 2-phenylethyl or benzyl.
Where R4 is campheryl, it is 10-campheryl.
When R4 if n = 2, is a -(CH2)m- group, it is for example ethylene, propylene, butylene, pentylene or
hexamethylene.
When phenylene and naphthylene are substituted by C1-C12-alkyl, they are straight-chain or branched
chain alkyl groups.
If the various phenyl groups in the radicals R1, R3-R4, R5 and R8 are substituted by radicals other than hydrogen atoms, this substitution occurs in the ortho-, meta- or para-position, especially in the para-position.
When R6, R7 and R8 are C,-C8-alkyl substituted by phenyl, they are for example benzyl or phenylethyl groups.
If R7 is C1-C4-alkylcarbonyl, the substituents are for example methyl-, ethyl propyl- or tert-butyl-carbonyl.
If R7 is C2-C5-aikoxycarbonyl, substituents are e.g. methoxy-, ethoxy-, isopropoxy-, butoxy- or tert-butoxy carbon.
When phenyl as R8 is substituted by C1-C4-alkyl or C1-C4-alkoxy, the substituents are methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl, or methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or tert-butoxy.
When R8 is C2-C6-alkenyl, it is for example vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-butenyl, isobutenyl, 2-pentenyl, 2-hexenyl or 5-hexenyl, particularly however vinyl, isobutenyl or 1 -propenyl.
When R8 is C8-C > -phenylalkenyl, substituents are styryl or 3-phenylpropenyl, especially however styryl.
If R8 is furyl or thienyl, all position isomers come into consideration. Preferred position isomers are however 2-furyl and 2-thienyl.
If R8 is unsaturated C5-C5-cycloalkyl, it is for example 2-cyclopenten-1-yl, 1-cyclohexen-1-yl or 3 cyclohexen-1 -yl.
Particularly preferred curing catalysts of the formulae land II are those wherein n = 1, and R1 is phenyl which is unsubstituted or substituted for example by: chlorine, methyl, methoxy, methylthio, phenylthio, -SCH2CH2OH or benzoyl, R2 is hydrogen or C1-C4-alkyl, R3 is hydrogen or C1-C4-alkyl, or R2 and R3 together with the carbon atom to which they are bound form a cyclohexane ring, R4 is C1-C18-alkyl, phenyl or naphthyl each unsubstituted or substituted by C1-C12-alkyl, or it is campheryl, R5 is phenyl which is unsubstituted or substituted by: -Cl, C1-C4-alkyl, C1-C4-alkoxy, -SCH3 or phenyl, R8 is -OH or C1-C4-alkyl, R7 is C1-C4-alkyl or phenyl, and R8 is -H, C1-C4-alkyl, furyl or -CCI3, or R7 with R8 together with the carbon atom to which they are bound form a cyclohexane ring.
More especially preferred are curing catalysts of the formulae land II wherein n = 1, R1 and R5 are each phenyl, p-tolyl or p-methylthiophenyl, R2 is hydrogen, R3 is methyl, isopropyl, n-decyl or benzyl, R4 is phenyl, p-tolyl or p-n-dodecylphenyl, R6 is -OH, R7 is -CH3 or phenyl, and R8 is -H.
The compounds of the formula I are known and can be produced by known processes, for example by reaction of the corresponding hydroxyl compounds of the formula (A)
with one or half an equivalent of the corresponding mono- or di-sulfonic acid chlorides of the formula (B) R4(SO2CI)n (B), in the presence of a base (cp. in this connection: Journal of the Chemical Society Perkin l, 1981, p. 263); or by reaction of the corresponding bromine derivatives of the formula (C)
with one or half an equivalent of the silver salts of the corresponding mono- or disulfonic acid derivatives of the formula (D) (AgO3S + R4 (D), as for example according to the process given in the Journal of Organic Chemistry of the UdSSR, Vol.8, p.2166(1972).In the formulae (A), (B), (C) and (D), the symbols R1 to R4 and n have the meanings defined in the foregoing.
The intermediates of the formulae (A), (B), (C) and (D) are known compounds which can be produced by known processes, for example by those which are described in Houben-Weyl, Methoden der Organischen
Chemie: Vol. V/4, pp. 171-189, for the compounds of the formula (C); Vol. IX, p.411 or 563, for the compounds of the formula (B); and for the compounds of the formula (A): the references A. 526,143,164 (1936), Am. Soc. 76,4402(1954) orZ. obsc. Chim. 34,3165(1964).
The compounds of the formula (II) are known and can be produced by known processes, for example by reaction of the corresponding epoxy compound of the formula (E)
with one equivalent of the corresponding monosulfonic acid derivative of the formula (F), or with half an equivalent of the disulfonic acid derivative of the formula (G)
R4 - SO3H (F) HO3S-R4-SO3H (G), for example by the processes described in Ber. Deutsch. Chem. Ges. 69,2753(1936), and in J. Chem. Soc.
1949,315; or by reaction of a corresponding hydroxyl compound of the formula
with a mono- or disulfonic acid chloride of the formulae R4-SO2CI and Cl02S-R4-SO2CL, respectively, according to the process given in the German Offenlegungsschrift 1,919,678. In the formulae (E), (F) and (G), the symbols R5, R6, R7, R8 and R4 have the meanings defined in the foregoing.
The required epoxy compounds of the formula (E) can be produced by known processes, for example by chlorination of the corresponding compound of the formula (H)
to the corresponding chlorine derivative of the formula (K)
which is reacted by subsequent condensation with the corresponding aldehyde of the formula (L)
to the corresponding epoxy compound of the formula (E) [cp. in this respect: Chem. Soc. 75,2042 (1953)]; or by an aldol condensation of the corresponding compound of the formula (H) with the corresponding aldehyde of the formula (L) to give the corresponding compound of the formula (M)
which is subsequently reacted for example by means of hydrogen peroxide to the corresponding epoxy compound of the formula (E) [cp. in this connection: J. Chem. Soc., 79,928 (1901)] and Org. Syntheses 60, 88 (1981), for the aldol condensation, and J. Org. Chem. 28,250(1963) or Org. Syntheses 55, (1967),forthe formation of the epoxy derivatives].
In the formulae (H), (K), (L) and (M), the symbols R5, R7 and R8 are as defined in the foregoing.
The compounds of the formulae (F) and (G) can be produced by known processes, for example by those which are described in Houben-Weyl, Methoden der Organischen Chemie, Vol. IX, p.p. 347 and 435.
Further masked curing catalysts can be used in the present process. Examples of these are a-methylolbenzoinsulfonic acid esters, which are described in the German Offenlegungsschrift No.
1,919,678; 4-benzoyl-4-phenyl-2-oxo-1 ,3,2-dioxathiolane (according to German Offenlegungsschrift No.
2,842,002); and N-sulfonyloxyimides, which are described for example in the European Patent Application
No. 58638.
The curing catalysts which are usable according to the invention are added to the resins in an amount sufficient for curing. The required amount depends not only on the type of resin, but also on the intended curing temperature and curing time. The amount used in general is 0.1 to 10% by weight, preferably 0.5 to 5 % by weight, of curing catalyst, relative to the solvent-free resin. Also mixtures of such cu ring catalysts can be used.
Suitable as acid-curable binders for abrasives are the resins of which the curing can be accelerated by acid catalysts. They are in particular pheno-and aminoplasts, for example the condensation products of formaldehyde with phenol, resorcin, cresol, xylenol, and mixtures thereof, urea, anilines or melamine. Other aldehydes, such as acetaldehyde, furfurol and acrolein, can be used in place of formaldehyde.
The acid-curable phenol resins and aminoplasts are described in detail in "Methoden der Organischen
Chemie", Houben-Weyl, Vol. 14/2,4th Edition (1963), p.p. 193-302 and 319-400.
Further acid-curable resins can be modified melamine resins, including etherified, esterified and otherwise modified melamine resins, for example alkydmelamine resins, as well as acrylic esters or polyesters, or alkyd resins. The binders can moreover consist of several identical or different acid-curable resins. Mixtures of various phenol resins, which are described for example in the European Patent Application No. 12409, can also be used.
The phenol-formaldehyde resins are particularly preferred, especially the aqueous-liquid, weakly alkaline to neutral phenol-formaldehyde condensation products of the resol type, which have greatly gained in importance. It is advantageous with the use of aqueous-liquid alkaline resins to neutralise resins of this type before the addition of the curing catalyst.
More especially of interest are aqueous phenol-formaldehyde resins (the so-called resol types) which have been made neutral to weakly acid (pH 4-6).
The binders can be solutions or dispersions of the resin in an organic solvent, preferably in aliphatic alcohols, or in water. They can contain, in addition to the abrasive and the curing catalyst, also fillers and additives, such as those customarily used in the abrasives industry, for example: agents improving the viscosity index, thickeners, dispersing agents, additives for improving the mechanical and thermal properties of the abrasives, and also adhesion promoters.
As abrasives or abrasive grain, there are used substances having a very great hardness and different particle sizes, the actual chipping or cutting work being done by these substances. Corundum and silicon carbide are mainly used. Further known abrasive grains are zirconium oxide, boron carbide, boron nitride, quartz, granate, or glass, and various metal powders, such as Si, Cu, Ag or Ni, as well as metal alloys.
Examples of fillers and additives are: graphite, molybdenum disulfide, iron pyrite, potassium sulfate, barium sulfate, cryolite, iron sulfide, sodium chloride, magnesia, calcium oxide, calcium fluoride, calcium carbonate, kaolin, glass fibres and also various plastics, for example vinyl chloride/vinylidene chloride copolymers, polyvinylidene chloride and PVC, or various halides, sulfates orsulfites, or mixtures thereof, or other fillers known in the abrasives industry.
The binders can also contain smallish amounts of special additives, for example co-initiators, as well as spectroscopic sensitisers. Examples of these are benzoin and derivatives thereof, benzil and derivatives thereof, and (x-di- and trisubstituted acetophenones, derivatives of anthracene orthioxanthone, and also organic dyes.
The mentioned resins and binders, abrasives, fillers and additives constitute no limitation of scope: they are given merely by way of example of an embodiment of the invention.
Preferred abrasive compositions are as follows:for the covering binder:
A) 30 - 70 % by weight of a filler,
70 - 30 % by weight of resol (80 % by weight in water),
1 - 5 % by weight of water, and
0.2 - 2% by weight of a curing catalyst; and for the base binder:
B) 2-20 % by weight of filler(s),
80 - 98 % by weight of resol (80 % by weight in water),
1 - 5 % by weight of water, and
1 - 4% byweightofcatalyst: with the proviso that the sum of the four components of the composition amounts always to 100% by weight.
As already mentioned, the process for producing flexible abrasives passes through two phases, namely, the drying phase for the abrasive composition and the subsequent curing phase.
In the drying phase, the employed soivent or water is partially to completely evaporated off.
In the subsequent curing phase, the binder is cross-linked to the extent that the abrasive grain is adequately anchored during further treatment and can thus be no longer moved. This anchoring is of decisive importance for the quality of the finished product. The preliminary curing is usually performed at relatively high temperature, for example at 130"C and above, and for one to several hours.
With the use of the masked catalysts which are applicable according to the present invention, the curing process can however be performed at relatively low temperatures and with shortened curing times, thus for example at temperatures of below 100"C, preferably at between 60 and 90"C, and within 1 to 200 minutes.
These relatively low curing temperatures and shortened curing times in the process according to the invention are of considerable technical importance; thus for example in the case where water-containing substrates are used a subsequent tempering in a humidity chamber in order to recover flexibility is rendered unnecessary by virture of these advantages. A further factor is the resulting saving in energy costs.
Afurther advantage of the process according to the invention is that the storage stability of the abrasive compositions is not impaired, even though they contain a curing catalyst. Furthermore, the curing catalyst becomes active not in the drying phase but subsequently in the irradiation phase, effecting not until then the curing of the binder with formation of free sulfonic acid.
The exposure of the resin to light rays is performed preferably with UV light, for which purpose there is available today a variety of suitable commercial devices. These incorporate medium pressure, high pressure or low pressure mercury vapour lamps, as well as fluorescent tubes, the emission maxima of which are at 250 to 400 nm. The exposure times necessary depend on the layer thickness of the resin, on the filling of the abrasive composition, on the light intensity of the lamps and on the distance between the lamps and the material being exposed. An abrasive composition at the customary layer thickness requires in the usual UV radiation aparatus an exposure time of several seconds to minutes. In this time, the latent catalyst has become photochemically transformed with the formation of free sulfonic acid.
When photosensitisers are added to the resin, the irradiation can be carried out also with daylight lamps.
Examples of known photosensitisers are condensed aromatic compounds, for example perylene, aromatic amines (such as are described for example in the U.S. Patent Specification No. 4,069,054), or cationic and basic dyes (such as are described for example in the U.S. Patent Specification No. 4,026,705).
The curing catalysts which are applicable according to the invention can be used also in the subsequent treatment, in which a covering binder layer, usually filled with fillers such as calcium carbonate, is applied, and then cured by exposure to light and heat treatment, in consequence of which the curing of the covering binder is accelerated and the curing time shortened.
Atempering treatment in a humidity chamber can if required by performed following the curing operation.
The further processing steps in the production of the abrasives are carried out in the manner customary in practice.
The process according to the invention is suitable in particular for producing flexible abrasives on flat (sheetlike) carrier material, for example on fibres, such as vulcanised fibres, abrasive fabrics or abrasive paper, as well as on combinations of paper and textile fabrics. The process is suitable moreover for the production of abrasive disks, such as abrasive elements, rings, points, segments, cylinders or heads.
The following Examples further illustrate the process of the invention on the basis of specific compositions according to the invention. The term 'parts' denotes parts by weight, and percentages are per cent by weight.
EXAMPLE 1
Testing of the anchoring of the abrasive grain, and also of the curing of the base binder in the presence of curing catalysts applicable according to the invention
30 % by weight (relative to the solid content of the phenolformaldehyde resin) of a 10 % (by weight) catalyst solution (in methylpentyl ketone) is mixed up in an aqueous phenol-formaldehyde resin MS 7215(*).
The phenolformaldehyde resin solution thus obtained is applied with a 200 W coaxing knife to an aluminium sheet (dry-film thickness about 40-50 ), and subsequently coated with corundum. For this purpose, the corundum is placed into a longish V-shaped funnel, the slit-shaped opening of which is covered with a metal sieve, and the funnel is secured to a vibrator. For applying the corundum coating, the vibrator is switched on, whereupon the aluminium sheet coated with resin is passed art a uniform rate under the funnel (amount applied per m2: 400-600 g of corundum). For removal of the water, the aluminium sheet thus coated is afterwards transferred for 35 minutes to a circulating-air chamber at 90"C, and is then exposed at a distance of 15cm to light rays from fluorescent tubes (Philips TLK0' 40/09) for 5, 10 and 15 minutes, in the course of which there is liberated from the catalyst applicable according to the invention an organic acid which catalyses the curing of the binder. The specimens are tested after subsequent curing for 20 minutes at 90"C.
The anchoring of the abrasive grain (corundum) in the preliminarily cured phenol-formaldehyde resin is qualitatively tested by the surface of the specimens being touched, and assessed according to the following system of classification:
A = can be moved with the finger
B = is firmly anchored, and can no longer be moved with the finger.
The degree of curing of the binder is measured on a binder film without corundum according to the
Knoop-measuring method (ASTM D 1474). The results are shown in Table 1.
(*) phenol-formaldehyde resin MS 7215 (Ciba-Geigy): 77 % by weight of solid substance; aqueous solution; pH = 4.5; viscosity = 2.5 - 3 Pas at 25 C; molar ratio phenol: formaldehyde = 1:1.2.
TABIE 1
Ex.No. Curing catalyst of the formula Exposure time Hardness Anchoring of the in minutes ASTM D 1474 abrasive grain
0 * A 5 37 B 10 34 B 15 32 B 0 * A 5 34 B 10 34 B 15 34 B 0 * A 5 34 B 10 32 B 15 35 B 0 * A 5 32 B 10 32 B 15 37 B
0 * A 5 32 B 10 35 B 15 30 B 0 * A 5 34 B 10 34 B 15 30 B 0 * A 5 * A 10 * A 15 * A G without catalyst * not measurable (still soft and sticky) The results show that the catalysts applicable according to the invention effect no preliminary curing during the drying phase (the unexposed coatings are still soft and sticky, the corundum is not firmly anchored).Not until exposure to light rays does the catalyst become degraded with the formation of active sulfonic acids, which render possible a rapid preliminary curing of the binder at low temperatures, in consequence of which the curing process is simultaneously shortened. An adequate preliminary curing of the binder has occurred after 20 minutes at 90"C, whereas the corresponding specimen without catalyst is still soft and sticky after the same curing time. The abrasive is already well anchored after an exposure time of 5 minutes, in comparison to which the unexposed specimens and freely movable.
EXAMPLE 2
Testing of the curing of the covering binder
The phenolformaldehyde resin MS 7215 described in Example 1 is mixed with 30 % by weight (relative to the solid content of the phenol resin) of a 10 % (by weight) catalyst solution (in methylpentyl ketone), and then filled with chalk [ratio of resin (100% solid substance) to chalk is 2 to 1]. The mixture obtained is applied, by the process given in Example 1, to an aluminium sheet. For removal of the water, the coated aluminium sheet is placed for 35 minutes into the oven at 90"C; it is then exposed for 5, 10 and 15 minutes, at a distance of 15cm, to the light from fluorescent tubes (Philips TLK z 40/09).After subsequent curing of these test specimens for 20 minutes at 90"C, the degree of cu ring of these specimens is determined according to the
Knoop measuring method (ASTM D 1474).
The results are summarised in Table 2.
TABLE 2
Catalyst of the formula Exposure time Hardness
in minutes ASTM D
1474
o * 5 14 10 14 15 17 * measurement not possible; specimen sticky and soft.
The results show that the exposed specimens have a sufficient hardness already after 5 minutes' exposure time and a curing time of 20 minutes at 900C, whereas the unexposed specimen is still soft and sticky after a curing time of 20 minutes.
EXAMPLE 3:
30 % by weight (relative to the solid content of the phenol-formaldehyde resin) of a 10 % (by weight) catalyst solution (in methylpentyl ketone) is mixed up in an aqueous phenol-formaldehyde resin MS 7216 (*).
The solution thus obtained is applied onto an aluminium sheet by the method described in Example 1, and thereupon coated with corundum; it is afterwards placed into an air-circulating oven at 90C for 35 minutes, and then exposed for 5, 10 and 15 minutes under fluorescent tubes. After subsequent curing for 20 minutes at 90"C, the specimens are tested as in Example 1 The results are summarised in Table III.
TABLE Ill
Catalyst of the formula Exposure Hardness Anchoring of
time in ASTM D the abrasive
minutes 1474 grain
0 * A
5 31 B 10 35 B 15 29 B * measurement not possible; specimen sticky and soft;
A. B: see classification in Example 1.
(*) phenol-formaldehyde resin MS 7216 (Ciba-Geigy): 79% by weight of solid substance; aqueous
solution; pH = 4.5; viscosity 2.5 - 3.0 Pas at 25"C; molar ratio phenol :formaldehyde = 1:1.8.
Claims (16)
1. A process for curing abrasive compositions containing an acid-curable binder and, as curing catalyst, an organic sulfonic acid releasable by the action of light, in which process the abrasive compositions after drying are exposed to the action of light rays and thus cured.
2. A process according to Claim 1, wherein the curing is performed at temperatures of between 60 and 100"C.
3. A process according to Claim 1, wherein the exposure is performed with UV light.
4. A process according to Claim 1, wherein there are used, as curing catalysts, organic compounds of the formulae I and II
wherein n is 1 or2, R, is phenyl or naphthyl which is unsubstituted or substituted or
R1 is anthryl, phenanthryl, thienyl, pyridyl, furyl, indolyl or tetrahydronaphthyl, and
R2 and R3 independently of one another are each hydrogen, or C,-C8-alkyl which is unsubstituted or
substituted or they are benzoyl, in addition
R3 is phenyl which is unsubstituted or substituted or it it is C2-C8-alkoxycarbonyl, -CN, C,-C4-alkyl-NH- CO-, phenyl-NH-CO- or -CONH2, C1-C4-alkyl-NH-CO, phenyl-NH-CO- or -CON H2, or
R2 and R3 together with the carbon atom to which they are bound form a C4-C6-cycloalkyl ring, R4 is, when n = 1, C1-C18-alkyl, phenyl which is unsubstituted or substituted or it is naphthyl which is
unsubstituted or substituted or it is C5-C6-cycloalkyl, C7-Cg-aralkyl, campheryl, -CF3, -CCI3, -F or
-NH2, and
R4 is, when n = 2, a -(CH2)m group, wherein m is 2 to 8, or phenylene or naphthylene each unsubstituted
or substituted R5 is phenyl or naphthyl which are each unsubstituted or substituted by 1,2 or 3 radicals; -Cl, -Br, C1-Clz-alkyl, phenyl, C1-C4-alkoxy, phenyloxy, benzyloxy, C1-C8-alkylthio, phenylthio, -SCH2CH2OH,
C1-C4-alkyl-CONH-, benzoylamino or dimethylamino, or by benzoyl, or R5 is anthryl or phenanthryl,
R6 is hydrogen, -OH, C1-C4-alkoxy, -OSi(CH3)3, -OCOCH3 or C1-C8-aIkvI which is unsubstituted or
substituted by phenyl,
R7 is hydrogen, or C1-C8-alkyl which is unsubstituted or substituted by phenyl, or R7 is -CN, benzoyl,
C1-C4-alkylcarbonyl, C2-C5-alkoxycarbonyl or phenyl,
R8 is hydrogen, C1-C8-alkyl which is unsubstituted or substituted by -OH, -Cl or phenyl, or it is phenyl
which is unsubstituted or substituted by -OH, -Cl, C1-C4-alkyl or C1-C4-alkoxy, or R8 is C2-C6-alkenyl, C8-Cg-phenylalkenyl, furyl, thienyl or -CCl3, or saturated or unsaturated C5-C6-cycloalkyl, and
moreover
R5 with R7, R7 with R8 or Re with R7, together with the carbon structure to which they are bound, form a 5
or 6-membered ring which contains 1 to 5: -CH2-, -CH(CH3)-, -C(CH3)2-, -0-, -S-, -50-, -SO2-, -CO-, -N(CO-C1-C4-alkyl)- or -N(COC6H5)- groups.
5. Process according to claim 4 wherein in the formulae I and II nisl or2,
R1 is phenyl or naphthyl which is unsubstituted or substituted by 1,2 or 3 radicals :-CI, -Br, -CN, - NO2, C1-C12-alkyl, C1-C4-alkoxy, phenyloxy, tolyloxy, phenylthio, tolylthio, C1-C8-alkylthio, -SCH2CH2OH,
C1-C4-alkylsulfonyl, phenylsulfonyl, C2-C4-alkoxycarbonyl, C1-C4-alkylamino, C2-C4-dialkylamino,
phenyl-CONH- or C1-C4-alkyl-CONH- or by benzoyl, or
R1 is anthryl, phenanthryl, thienyl, pyridyl, furyl, indolyl or tetrahydronaphthyl, and
R2 and R3, independently of one another, are each hydrogen, or C1-C8-alkyl which is unsubstituted or
substituted by -OH, -Cl, C1-C4-alkoxy, -CN, -C2-C5-alkoxycarbonyl, phenyl, chlorophenyl, C7-C10
alkylphenyl or C7-C1O-alkoxyphenyl or they are benzoyl, in addition
R3 is phenyl which is unsubstituted or substituted by -Cl, C1-C4-alkyl, C1-C4-alkoxy, or C1-C4-alkylthio or it
is C2-C8-alkoxycarbonyl, -CN, C1-C4-alkyl-NH- CO-, phenyl-NH-CO-, or -CONH2, or
R2 and R3, together with the carbon atom to which they are bound, form a C4-C6-cycloalkyl ring, R4 when n = 1, is C1-Cl8-alkyl, phenyl which is unsubstituted or substituted by halogen, C1-C12-alkyl, C1-C4-alkoxy, C1-C4-alkyl-CONH-, phenyl-CONH-, -NO2 or benzoyl, or it is napthyl which is
unsubstituted or substituted by halogen, C1-C12 alkyl or C1 -C4 alkoxy, or it is C5-C6-cycloalkyl, C7-Cg-aralkyl, campheryl, CF3, -CCI3, -F or -NH2, and
R4 is, when A = Z, a -(CH2)m group wherein m is 2 to 8, or phenylene or naphthylene each unsubstituted
or substituted by C1-C12 alkyl, and R5, R6, R7 and R8 are as defined in claim 4.
6. A process according to Claim 5, wherein in the formulae I and II n iso, R1 is phenyl which is unsubstituted or substituted by chlorine, methyl, methoxy, methylthio, phenylthio,
-SCH2CH2OH or benzoyl,
R2 is hydrogen or C1-C4-alkyl, Rs is hydrogen or C1-C4-alkyl, or
R2 and R3 together with the carbon atom to which they are bound form a cyclohexane ring, R4 is C1-C18-alkyl, phenyl or naphthyl each unsubstituted or substituted by C1-C13-alkyl, or it is campheryl,
R5 is phenyl which is unsubstituted or substituted by: -Cl, C1-C4-alkyl, C1-C4-alkoxy, -SCH3 or phenyl, Re is -OH or C1-C4-alkyl,
R7 is C1-C4-alkyl or phenyl, and
R8 is -H, C1-C4-alkyl, furyl or -CCI3, or
R7 with R8 together with the carbon atom to which they are bound form a cyclohexane ring.
7. A process according to Claim 6, wherein in the formulae I and II n is 1, R1 and R8 are each phenyl, p-tolyl or p-methylthiophenyl, R2 is hydrogen, R3 is methyl, isopropyl, n-decyl or benzyl, R4 is phenyl, p-tolyl or p-n-dodecylphenyl, R8 is -OH, R7 is -CH3 or phenyl, and R8 is -H.
8. A process according to Claim 1, wherein the acid-curable binder is a pheno- or aminoplast, or a mixture thereof.
9. A process according to Claim 8, wherein the acid-curable binder is a phenol-formaldehyde resin.
10. A process according to Claim 8, wherein the acid-curable binder is a resol.
11. A process according to Claim 1, wherein the acid-curable binder contains 0.1 to 10% by weight, relative to the solvent-free binder, of the curing catalyst.
12. A process according to Claim 1, wherein the binder is the base binder.
13. A process according to Claim 1, wherein the binder is the covering binder.
14. A process according to Claim 1 for producing flexible abrasives on flat or sheetlike carrier materials.
15. A process for curing abrasive compositions substantially as described with reference to any of the
Examples.
16. Abrasive compositions when cured by a process claimed in any of the preceding claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH305182 | 1982-05-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8313057D0 GB8313057D0 (en) | 1983-06-15 |
| GB2120263A true GB2120263A (en) | 1983-11-30 |
| GB2120263B GB2120263B (en) | 1985-07-31 |
Family
ID=4247509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08313057A Expired GB2120263B (en) | 1982-05-17 | 1983-05-12 | A process for curing acid-curable abrasive compositions |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS58213079A (en) |
| CA (1) | CA1216816A (en) |
| DE (1) | DE3317570A1 (en) |
| FR (1) | FR2526801B1 (en) |
| GB (1) | GB2120263B (en) |
| NO (1) | NO831755L (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4618564A (en) * | 1984-05-25 | 1986-10-21 | Ciba-Geigy Corporation | Process for production of positive images using sulfonic acid precursors |
| US4737426A (en) * | 1985-05-15 | 1988-04-12 | Ciba-Geigy Corporation | Cyclic acetals or ketals of beta-keto esters or amides |
| US4957988A (en) * | 1985-05-22 | 1990-09-18 | Ciba-Geigy Corporation | Process and polymers for the production of images |
| US4997717A (en) * | 1987-03-27 | 1991-03-05 | Ciba-Geigy Corporation | Photocurable abrasives |
| US5378252A (en) * | 1993-09-03 | 1995-01-03 | Minnesota Mining And Manufacturing Company | Abrasive articles |
| EP0709410A2 (en) | 1994-10-26 | 1996-05-01 | OCG Microelectronic Materials, Inc. | Polymers |
| US5585218A (en) * | 1993-06-02 | 1996-12-17 | Sumitomo Chemical Company, Limited | Photoresist composition containing alkyletherified polyvinylphenol |
| US5650262A (en) * | 1992-10-29 | 1997-07-22 | Muenzel; Norbert | High-resolution negative photoresist with wide process latitude |
| WO1998023713A1 (en) * | 1996-11-26 | 1998-06-04 | Haisten Eugene Keith Jr | Waterless and solvent hand and skin cleaner |
| US7759515B2 (en) | 2001-09-28 | 2010-07-20 | Daicel Chemical Industries, Ltd. | Catalyst comprising N-substituted cyclic imide compound and process for producing organic compounds using the catalyst |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3418477A1 (en) * | 1984-05-18 | 1985-11-21 | Rütgerswerke AG, 6000 Frankfurt | RADIATION-HARDENING BINDING AGENT AND METHOD FOR THE PRODUCTION OF FLAT AREAS |
| US4828583A (en) * | 1987-04-02 | 1989-05-09 | Minnesota Mining And Manufacturing Company | Coated abrasive binder containing ternary photoinitiator system |
| JPS63295680A (en) * | 1987-05-27 | 1988-12-02 | Nippon Paint Co Ltd | Thermosetting water-based coating composition |
| US4802896A (en) * | 1987-12-08 | 1989-02-07 | Minnesota Mining And Manufacturing Company | Modified resins and abrasive articles made with the same as a bond system |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB572986A (en) * | 1941-05-17 | 1945-11-01 | Bakelite Ltd | Improvements in or relating to phenol-aldehyde resins |
| GB907762A (en) * | 1959-03-02 | 1962-10-10 | Norton Co | Curable aminoplast adhesive compositions and products |
| GB964806A (en) * | 1960-08-24 | 1964-07-22 | Norton Co | Method of making a grinding wheel |
| DE1919678A1 (en) * | 1969-04-18 | 1970-11-05 | Bayer Ag | Alpha-methylol-benzoin-sulfonic acid ester |
| GB1290344A (en) * | 1968-12-19 | 1972-09-27 | ||
| GB1298401A (en) * | 1969-03-14 | 1972-12-06 | Minnesota Mining & Mfg | Curing cationic sensitive monomers with latent bis(fluoroalkylsulphonyl)methane catalysts |
| GB1431676A (en) * | 1972-03-27 | 1976-04-14 | Rex Chainbelt Inc | Applying an abrasive-resistant coating to a surface |
| GB1535492A (en) * | 1976-07-14 | 1978-12-13 | Gen Electric | Curable compositions and method for curing such compositions |
| DE2842002A1 (en) * | 1978-09-27 | 1980-04-10 | Bayer Ag | Benzoyl phenyl oxo-dioxathiolane cpds. useful as photoinitiators - for acid-hardenable resins and their prodn. from alpha:hydroxy-alkyl-benzoic cpds. |
| GB1566890A (en) * | 1975-12-22 | 1980-05-08 | Hoechst Ag | Binder compositions |
| GB2045264A (en) * | 1979-03-06 | 1980-10-29 | Fuji Photo Film Co Ltd | Photopolymerizable compositions containing ethylenic monomer |
| GB1587349A (en) * | 1977-03-29 | 1981-04-01 | Bayer Ag | Photopolymerisable coatings |
| EP0037152A1 (en) * | 1980-03-31 | 1981-10-07 | Akzo N.V. | Initiator system for radiation curable compositions, radiation curable compositions containing such an initiator system, a process for curing said compositions and products covered therewith |
| EP0058638A2 (en) * | 1981-02-13 | 1982-08-25 | Ciba-Geigy Ag | Curable compositions containing an acid-curable resin, and process for curing them |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR37152E (en) * | 1928-11-07 | 1930-10-25 | Method for collecting fruit falling from a tree, in particular for collecting apples or cider fruit and nuts | |
| EP0009519B1 (en) * | 1978-10-09 | 1984-12-12 | Hoechst Aktiengesellschaft | Application of resin binders to the manufacture of abrasive articles, and the manufactured abrasive articles |
| US4510290A (en) * | 1982-01-11 | 1985-04-09 | Ciba Geigy Corporation | Acid-curable composition containing a masked curing catalyst, and a process for the curing thereof |
| EP0899822A3 (en) * | 1997-08-11 | 1999-11-03 | Framatome Connectors International | Plug-in connector arrangement |
-
1983
- 1983-05-12 GB GB08313057A patent/GB2120263B/en not_active Expired
- 1983-05-13 DE DE19833317570 patent/DE3317570A1/en not_active Withdrawn
- 1983-05-13 CA CA000428111A patent/CA1216816A/en not_active Expired
- 1983-05-16 FR FR8308043A patent/FR2526801B1/en not_active Expired
- 1983-05-16 NO NO831755A patent/NO831755L/en unknown
- 1983-05-17 JP JP58086488A patent/JPS58213079A/en active Pending
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB572986A (en) * | 1941-05-17 | 1945-11-01 | Bakelite Ltd | Improvements in or relating to phenol-aldehyde resins |
| GB907762A (en) * | 1959-03-02 | 1962-10-10 | Norton Co | Curable aminoplast adhesive compositions and products |
| GB964806A (en) * | 1960-08-24 | 1964-07-22 | Norton Co | Method of making a grinding wheel |
| GB1290344A (en) * | 1968-12-19 | 1972-09-27 | ||
| GB1298401A (en) * | 1969-03-14 | 1972-12-06 | Minnesota Mining & Mfg | Curing cationic sensitive monomers with latent bis(fluoroalkylsulphonyl)methane catalysts |
| DE1919678A1 (en) * | 1969-04-18 | 1970-11-05 | Bayer Ag | Alpha-methylol-benzoin-sulfonic acid ester |
| GB1265604A (en) * | 1969-04-18 | 1972-03-01 | ||
| GB1431676A (en) * | 1972-03-27 | 1976-04-14 | Rex Chainbelt Inc | Applying an abrasive-resistant coating to a surface |
| GB1566890A (en) * | 1975-12-22 | 1980-05-08 | Hoechst Ag | Binder compositions |
| GB1535492A (en) * | 1976-07-14 | 1978-12-13 | Gen Electric | Curable compositions and method for curing such compositions |
| GB1587349A (en) * | 1977-03-29 | 1981-04-01 | Bayer Ag | Photopolymerisable coatings |
| DE2842002A1 (en) * | 1978-09-27 | 1980-04-10 | Bayer Ag | Benzoyl phenyl oxo-dioxathiolane cpds. useful as photoinitiators - for acid-hardenable resins and their prodn. from alpha:hydroxy-alkyl-benzoic cpds. |
| GB2045264A (en) * | 1979-03-06 | 1980-10-29 | Fuji Photo Film Co Ltd | Photopolymerizable compositions containing ethylenic monomer |
| EP0037152A1 (en) * | 1980-03-31 | 1981-10-07 | Akzo N.V. | Initiator system for radiation curable compositions, radiation curable compositions containing such an initiator system, a process for curing said compositions and products covered therewith |
| EP0058638A2 (en) * | 1981-02-13 | 1982-08-25 | Ciba-Geigy Ag | Curable compositions containing an acid-curable resin, and process for curing them |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4618564A (en) * | 1984-05-25 | 1986-10-21 | Ciba-Geigy Corporation | Process for production of positive images using sulfonic acid precursors |
| EP0166682A3 (en) * | 1984-05-25 | 1987-03-04 | Ciba-Geigy Ag | Process for obtaining positive images |
| US4737426A (en) * | 1985-05-15 | 1988-04-12 | Ciba-Geigy Corporation | Cyclic acetals or ketals of beta-keto esters or amides |
| US4957988A (en) * | 1985-05-22 | 1990-09-18 | Ciba-Geigy Corporation | Process and polymers for the production of images |
| US4997717A (en) * | 1987-03-27 | 1991-03-05 | Ciba-Geigy Corporation | Photocurable abrasives |
| US5650262A (en) * | 1992-10-29 | 1997-07-22 | Muenzel; Norbert | High-resolution negative photoresist with wide process latitude |
| US5585218A (en) * | 1993-06-02 | 1996-12-17 | Sumitomo Chemical Company, Limited | Photoresist composition containing alkyletherified polyvinylphenol |
| US5378252A (en) * | 1993-09-03 | 1995-01-03 | Minnesota Mining And Manufacturing Company | Abrasive articles |
| EP0709410A2 (en) | 1994-10-26 | 1996-05-01 | OCG Microelectronic Materials, Inc. | Polymers |
| WO1998023713A1 (en) * | 1996-11-26 | 1998-06-04 | Haisten Eugene Keith Jr | Waterless and solvent hand and skin cleaner |
| US7759515B2 (en) | 2001-09-28 | 2010-07-20 | Daicel Chemical Industries, Ltd. | Catalyst comprising N-substituted cyclic imide compound and process for producing organic compounds using the catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2120263B (en) | 1985-07-31 |
| JPS58213079A (en) | 1983-12-10 |
| CA1216816A (en) | 1987-01-20 |
| GB8313057D0 (en) | 1983-06-15 |
| FR2526801A1 (en) | 1983-11-18 |
| FR2526801B1 (en) | 1987-01-30 |
| DE3317570A1 (en) | 1983-11-17 |
| NO831755L (en) | 1983-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4636575A (en) | Masked curing catalyst for acid-curable compositions | |
| GB2120263A (en) | A process for curing acid-curable abrasive compositions | |
| US4431774A (en) | Process for the curing of stoving lacquers | |
| US4504372A (en) | Acid-curable composition containing a masked curing catalyst, and a process for its preparation | |
| CA1204547A (en) | Curable composition based on an acid-curable resin, and process for curing this resin | |
| EP0166682B1 (en) | Process for obtaining positive images | |
| CA1241930A (en) | Radiation and heat curing acid-curable finishes in the presence of oxime sulfonate | |
| US3689565A (en) | {60 -methylolbenzoin ethers | |
| US3849392A (en) | Process for the production of polycondensation products of aromatic diazonium compounds | |
| KR0150440B1 (en) | Radiation sensitive compounds, radiation sensitive mixtures and radiatives prepared therefrom | |
| CN109651534B (en) | Polyketoxime ester photoinitiator and preparation method and application thereof | |
| JPH04103612A (en) | Method of manufacturing high-tg novolac resin for high-resolution photoresist | |
| CN117865866B (en) | Polythienium salt single-molecule resin photoresist based on triptycene and preparation method thereof | |
| US2422637A (en) | Resinous condensation product of phenol and styrene oxide | |
| US4396756A (en) | Aldehyde condensate tackifiers for rubber | |
| JPH05241342A (en) | Negative photoresist composition | |
| US2228837A (en) | Process for producing resistant varnish coatings on wood | |
| CA1204545A (en) | Curing stoving lacquers using a quinolinium sulfonate as latent curing catalyst | |
| JPH0456026B2 (en) | ||
| US3327018A (en) | Fluorescent aldehyde-triazinyl stilbino condensation products | |
| US2576735A (en) | Nitrogenous resins from ketonealdehyde-nitrogenous base and phenol-aldehyde | |
| JPS58168635A (en) | Hardenable resin composition, manufacture and method | |
| US2120547A (en) | Vulcanization of rubber | |
| US2857346A (en) | Synthetic resin tanning agents containing alkali pretreated sulfite waste liquor and process of preparing same | |
| RU2095378C1 (en) | Adhesion activator |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |