# US 4,395,498 A · High temperature phenolic resins and friction elements prepared therefrom > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,395,498 A - Document ID: US4395498A - Status: Granted - Kind: A - Application number: 06/303,554 - Filed: 1981-09-18 - Granted: 1983-07-26 - Earliest claimed: 1981-09-18 - Assignees: Minnesota Mining and Manufacturing Company - Inventors: Judith L. Benham - Web page: https://patentgrep.com/patent/US4395498A ## CPC - F16D 69/026: {containing fibres} - C08G 14/04: with phenols - C08L 61/34: Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20 - F16D 69/025: {Compositions based on an organic binder} - F16D: COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract High temperature phenolic resins suited for use for example in an automotive or similar brake or in a clutch, are provided by a blend of the reaction product of a phenolic compound, naphthalenic compound, and formaldehyde with selected prior art resins. The mole ratio range of naphthalenic compound: phenolic compound: formaldehyde is about 1: 1:0.8-5:1-10. Friction particles and friction elements can be prepared from said reaction product optionally being blended with said selected prior art resins. An improved method of making friction elements is also provided which uses such binder. ## Claims ### Claim 1 A composition of matter heat stable to at least 371.degree. C. comprising a physical blend of a. 10 to 95 weight percent, based on resin solids, of a curable resin which is the acid-catalyzed reaction product of (1) at least one phenolic compound having the formula ##STR8## wherein each R independently represents an aliphatic group of 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, g is 1, 2, or 3, and z is 0, 1, or 2; (2) at least one naphthalenic compound having the formula ##STR9## wherein each R.sup.1 independently is a halo or an aliphatic group of 1 to 15 carbon atoms, and v is 0, 1, 2, and 3; and (3) formaldehyde; the mole ratio of naphthalenic compound:phenolic compound:formaldehyde in said composition being in the range of 1:0.8-5:1-10, b. 5 to 90 weight percent, based on curable binder resin solids, of prior art resins selected from bodied cashew nut shell liquid resin, bodied linseed oil resin, oil-modified phenolic resins, and mixtures thereof. ### Claim 2 (depends on 1) The composition of matter according to claim 1 wherein said ratio of naphthalenic compound to phenolic compound to formaldehyde is 1:1-3:1-5. ### Claim 3 (depends on 1) The composition of matter according to claim 1 wherein said ratio of naphthalenic compound to phenolic compound to formaldehyde is 1:2-2:1-4. ### Claim 4 (depends on 1) The composition of matter according to claim 1 wherein R of said phenolic compound is an aliphatic group having 4 to 15 carbon atoms. ### Claim 5 (depends on 1) The composition of matter according to claim 1 wherein said phenolic compound is selected from unsubstituted phenol, tert-butylphenol, tert-amylphenol, tert-octylphenol, nonylphenol, dodecylphenol, and cashew nut shell liquid. ### Claim 6 (depends on 1) The composition of matter according to claim 1 wherein z of said phenolic compound is equal to zero. ### Claim 7 (depends on 1) The composition of matter according to claim 1 wherein q of said phenolic compound is equal to 1 and z is equal to 0. ### Claim 8 (depends on 1) The composition of matter according to claim 1 wherein said phenolic compound comprises a mixture of unsubstituted phenol and cashew nut shell liquid. ### Claim 9 (depends on 1) The composition of matter according to claim 1 wherein said phenolic compound comprises a mixture of unsubstituted phenol and nonylphenol. ### Claim 10 (depends on 1) The composition of matter according to claim 1 wherein said phenolic compound comprises a mixture of unsubstituted phenol and dodecylphenol. ### Claim 11 (depends on 1) The composition of matter according to claim 1 wherein R.sup.1 of said naphthalenic compound is an aliphatic group having 1 to 12 carbon atoms. ### Claim 12 (depends on 1) The composition of matter according to claim 1 wherein v of said naphthalenic compound is equal to zero. ### Claim 13 (depends on 1) The composition of matter according to claim 1 wherein said prior art resin of said physical blend comprises bodied cashew nut shell liquid resin. ### Claim 14 (depends on 1) The composition of matter according to claim 1 wherein the prior art resin of said physical blend comprises bodied linseed oil resin. ### Claim 15 A friction element having a cured organic thermosettable binder resin with filler dispersed and bonded therein, said binder resin comprising: a physical blend of a. 10 to 100 weight percent, based on resin solids, of a curable resin which is the acid-catalyzed reaction product of (1) at least one phenolic compound having the formula ##STR10## wherein each R independently represents an aliphatic group of 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, q is 1, 2, or 3, and z is 0, 1, or 2; (2) at least one naphthalenic compound having the formula ##STR11## wherein each R.sup.1 independently is a halo or an aliphatic group of 1 to 15 carbon atoms, and v is 0, 1, 2, or 3; and (3) formaldehyde; the mole ratio of naphthalenic compound:phenolic compound:formaldehyde in said composition being in the range of 1:0.8-5:1-10, b. 0 to 90 weight percent, based on curable binder resin solids, of prior art resins selected from cashew nut shell liquid binder resin, bodied linseed oil, oil-modified phenolic resins, and mixtures thereof, and c. 5 to 10 weight percent, based on curable binder resin solids of formaldehyde donor compounds. ### Claim 16 A friction particle having a cured organic thermosettable binder resin and optionally having filler dispersed and bonded therein, said binder resin comprising: a physical blend of a. 10 to 100 weight percent, based on resin solids, of a curable resin which is the acid-catalyzed reaction product of (1) at least one phenolic compound having the formula ##STR12## wherein each R independently represents an aliphatic group of 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, q is 1, 2, or 3, and z is 0, 1, or 2; (2) at least one naphthalenic compound having the formula ##STR13## wherein each R.sup.1 independently is a halo or an aliphatic group of 1 to 15 carbon atoms, and v is 0, 1, 2, or 3; and (3) formaldehyde; the mole ratio of naphthalenic compound:phenolic compound:formaldehyde in said composition being in the range of 1:0.8-5:1-10, b. 0 to 90 weight percent, based on curable binder resin solids, of prior art resins selected from cashew nut shell liquid binder resin, bodied linseed oil, oil-modified phenolic resins, and mixtures thereof, and c. 5 to 10 weight percent, based on curable binder resin solids of formaldehyde donor compounds. ### Claim 17 A method of preparing a friction element comprising the steps of: a. admixing (1) a curable organic thermosettable binder resin, said resin comprising a physical blend of (a) 10 to 100 weight percent, based on resin solids, of the curable acid-catalyzed reaction product of (i) at least one phenolic compound having the formula ##STR14## wherein each R independently represents an aliphatic group of 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, q is 1, 2, or 3, and z is 0, 1, or 2; (ii) at least one naphthalenic compound having the formula ##STR15## wherein each R.sup.1 independently is a halo or an aliphatic group of 1 to 15 carbon atoms, and v is 0, 1, 2, or 3; and (iii) formaldehyde the mole ratio of naphthalenic compound:phenolic compound:formaldehyde in the resin being in the range of 1:0.8-5:1-10, (b) 0 to 90 weight percent, based on curable binder resin solids, of prior art resins selected from bodied cashew nut shell liquid resin, bodied linseed oil, oil-modified phenolic resins, and mixtures thereof, and (c) 5 to 10 weight percent, based on curable binder resin solids, of formaldehyde donor compounds, and (2) a filler material, and b. forming the mixture into the desired shape, and c. curing said binder resin. ### Claim 18 A composition of matter comprising a physical blend of a. 10 to 95 weight percent, based on resin solids, of a curable resin which is the acid-catalyzed reaction product of (1) at least one phenolic compound having the formula ##STR16## wherein each R independently represents an aliphatic group of 1 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms, q is 1, 2, or 3, and z is 0, 1, or 2; (2) at least one naphthalenic compound having the formula ##STR17## wherein each R.sup.1 independently is a halo or an aliphatic group of 1 to 15 carbon atoms, and v is 0, 1, 2, or 3; and (3) formaldehyde; the mole ratio of naphthalenic compound:phenolic compound:formaldehyde in said composition being in the range of 1:0.8-5:1-10; said resin being a polymeric structure of randomly aligned units having the structure: ##STR18## wherein a, b, c, d, and e are integers having a value of 0 to 1000; q, v, and z are as defined above, with the proviso that (d+e) is greater than zero; and b. 5 to 90 weight percent, based on curable binder resin solids, of prior art resins selected from bodied cashew nut shell liquid resin, bodied linseed oil resin, and mixtures thereof.