USRE16648E - And stanley krall - Google Patents
And stanley krall Download PDFInfo
- Publication number
- USRE16648E USRE16648E US16648DE USRE16648E US RE16648 E USRE16648 E US RE16648E US 16648D E US16648D E US 16648DE US RE16648 E USRE16648 E US RE16648E
- Authority
- US
- United States
- Prior art keywords
- rubber
- krall
- stanley
- triazine
- vulcanization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000008164 mustard oil Substances 0.000 description 6
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 5
- 239000004636 vulcanized rubber Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- CBNXGQUIJRGZRX-UHFFFAOYSA-N 5-[4-fluoro-3-(trifluoromethyl)phenyl]furan-2-carbaldehyde Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=CC=C(C=O)O1 CBNXGQUIJRGZRX-UHFFFAOYSA-N 0.000 description 1
- 241000896693 Disa Species 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Definitions
- the process of producing vulcanized rubber which comprises incorporating with the a or 6-difi-triazine and heatproduct with a vulcanizing derivative of Z-thiocarhonyl-l metl1yl-llexuhydro-l, 3, ing the resulting agent.
- vulcanized rubber which comprises incorporating with rubber a small amount ofa homologue the rubber a small amount of l-phenyl-2- thiocarbonyl, fi-dimethyl-hexahydro-1, 3, S-triazine, and heating the resulting product with a vulcanizing agent.
- A. vulcanized rubber having incorporated therein a small amount of the reaction product of an aldehyde-ainmonia with a mustard oil.
- a vulcanized rubber having incorpo rated therein a small amount of a homologue or derivative of Q-thiocarbouyld, 6- dimerhyl-hexahydro-l, 3, fi-triazine.
- a vulcanized rubber having inc0rp0- rated therein a small amount of l-phenyh 3thimaarlroxjryl-i, (i-diniet'hyl-l1e ;ah ydr01,3, Z-triazine.
Description
F fncture,
Reissued June 7, 1927.
NORMAN A. SHEPARD, OI AKRON, OHIO, MASSACHUSETTS, ASSIGNOBB TO THE Original 10. 1,516,072, dated No, muse This invention relates to the process of vulcanizing rubber and particularly to a new and improved method of combining rubber with vulcanizing agents to produce 5 improved results in operation.
It relates specifically to a new and useful method of accelerating ,the vulcanization of rubber by the addition of certain organic substances, as accelerators which are in- 10 tended to'quicken the process of vulcanization and to im rove the qualitiesof the cured or vulcanized rubber.
known and studied for many years, but all 15 of said substances are not suitable for use in obtaining stocks possessing certain characteristics and others, while possessing marked acceleratin properties, have had a limited commerciaf application owing to difiiculties attendant upon their use. Certain of said accelerators are-too volatile and loss occurs in the milling and calendaring. The fumes given ofi are objectionable and sometimes toxic so as to be dangerous to 25 use and requiring special ventilating equipment. Other disa vantages are present in certain known accelerators which render them unsuitable for various reasons. I It is the purpose of the present invention to make use of certain substanceswhich have heretofore been unused in the vulcanization of rubber, which substances do not have anyof the disadvantages which have been described,
can be worked into rubber compounds without disagreeable results and which will mix well in the compounds with out loss due to the excessive volatilit The substances which have been eveloped by us are formed by the condensation of aldehyde-ammonias with mustard oils or thiourea, which are then incorporated in the rubber mix in the usual manner.
The reaction product of amataldehvdeammonia with phenyl mustard oil has been PfiOCESB OF VULCANIZIHG RUBBER AND COMPOUH Rubber accelerators, so called, have been are easy and cheap to menu-- a Re, 15,648
-UNITED STATES PATENT OFFICE.
AND STANLEY KRALL, 0F LONGMEADQW, FIRESTQHE TIRE AND RUBBEB COMIANY,
O1? AKRON, OHIO, A CORPORATION OF OHIO.
n RESULTING 'rrmnnrmm,
No Drawing. .Orlginal application filed June 20, 1923, Serial No. 846,702, Renewed August 4, i925, larch 9, 1928. Application for reissue filed January 15, 192?, serial ascribed the following formula by Dixon This compound is l-phenyl-Q-thiocarbonyl- 4, 6-dimethyl--hexahy( ro-l, 3,
from objectionable odor, and for use as an accelerator of of rubber,
fi-triazine. It
- is non-volatile, well crystallized and is free is well suited vulcanization Similar products'may be obtained by the reaction of other mustard oils (isothiocyanates) Th us upon other aldehyde-ammonia. from allyl mustard oil and acetaldehyde-ammonia is obtained 1-allyl-2-thiocar bonylA, B-dimethyl-hexahydro-l, 3, b-triazine; while from bu raldehyde is car onyl-4,
henyl mustard oil and I o tained I-phenyI-Q'thim -6-di-butyl-hexahydro-1, U 5- triazine; and all of these reaction products are within the broad scope of the present.
invention, being rapid, easily handled and superior accelerators.
An example of the activity erators of vulcanization is as follows:
l-93.5 parts of these accelparts of zinc oxide and 1 part of 1-phenyl-2-thiocarbonyl-4, fi-dimethyl-hexahydrml, 3, IS-trinzine and heated in a vulcanizer for fortyfive minutes at 290 F. The
roduct is well cured and vulcanization so taken place in one-fifth of the time of heating required to produce similar physical prop 'erties without the addition of the accelerator.
It will be appreciated that the formula;
given above are not restrictive oi the invention and that as far as known to us we are the first to make use 0 f the 7 reaction I ll of smoked sheet are mixed products of aldehyde-aminonias with mustard oils or thiourea for acceleration of rubber vulcanization.
\Vhat We claim is:
1. The process of vulcanizing rubber which Comprises incorporating with rubber -a small amount of av reaction product of an aldehyde-ammonia with a mustard oil,
and heating the resultant product with a vulcanizing agent, I
The process of producing vulcanized rubber which comprises incorporating with the a or 6-difi-triazine and heatproduct with a vulcanizing derivative of Z-thiocarhonyl-l metl1yl-llexuhydro-l, 3, ing the resulting agent. a
3. The process. of producing vulcanized rubber which comprises incorporating with rubber a small amount ofa homologue the rubber a small amount of l-phenyl-2- thiocarbonyl, fi-dimethyl-hexahydro-1, 3, S-triazine, and heating the resulting product with a vulcanizing agent.
4. A. vulcanized rubber having incorporated therein a small amount of the reaction product of an aldehyde-ainmonia with a mustard oil.
5. A vulcanized rubber having incorpo rated therein a small amount of a homologue or derivative of Q-thiocarbouyld, 6- dimerhyl-hexahydro-l, 3, fi-triazine.
6. A vulcanized rubber having inc0rp0- rated therein a small amount of l-phenyh 3thimaarlroxjryl-i, (i-diniet'hyl-l1e ;ah ydr01,3, Z-triazine.
NORMAN A. SHEPARD. STANLEY KRALL.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US646702A US1576072A (en) | 1923-06-20 | 1923-06-20 | Process of vulcanizing rubber and compound resulting therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE16648E true USRE16648E (en) | 1927-06-07 |
Family
ID=24594120
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16648D Expired USRE16648E (en) | 1923-06-20 | And stanley krall | |
US646702A Expired - Lifetime US1576072A (en) | 1923-06-20 | 1923-06-20 | Process of vulcanizing rubber and compound resulting therefrom |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US646702A Expired - Lifetime US1576072A (en) | 1923-06-20 | 1923-06-20 | Process of vulcanizing rubber and compound resulting therefrom |
Country Status (1)
Country | Link |
---|---|
US (2) | US1576072A (en) |
-
0
- US US16648D patent/USRE16648E/en not_active Expired
-
1923
- 1923-06-20 US US646702A patent/US1576072A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US1576072A (en) | 1926-03-09 |
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