Claims
- 1. A process of preparing a nitrogen-containing telomer containing a high molecular weight hydrocarbon group, of average molecular weight between 400 and 3,000, nitrogen content of from 0.1 to 10 wt %, soluble in fuel oils and lubricating oils, which consists of subjecting to a radical telomerization reaction in the presence of a radical initiator at a temperature of 150.degree. C.-200.degree. C. a mixture of 1 mole of: (1) at least one nitrogen-containing compound as a telogen which is an alkanolamine or a cycloalkanolamine of formula ##STR13## in which R.sub.10 represents an alkanol group having at least one hydroxyl group and having from 1 to 45 carbon atoms, R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom, an alkyl group having from 1 to 45 carbon atoms or an alkanol group having at least one hydroxyl group and having from 1 to 45 carbon atoms, or R.sub.10 and R.sub.11 join to form a five- to seven-members saturated ring having at least one hydroxyl group, the ring being unsubstituted or substituted by 1-3 alkyl substituents each having from 1 to 6 carbon atoms, and (2) 0.1 to 20 moles of an alpha-olefin as a taxogen of the general formula R.sub.5 --CH.dbd.CH.sub.2, in which R.sub.5 is alkyl having from 1 to 28 carbon atoms whereby said taxogen becomes attached to the carbon atom in the .alpha.-position to the nitrogen atom of said telogen.
- 2. A process of preparing a nitrogen-containing telomer containing a high molecular weight hydrocarbon group, of average molecular weight between 400 to 3,000, nitrogen content of from 0.1 to 10 wt %, soluble in fuel oils and lubricating oils, which consists of subjecting to a radical telomerization reaction in the presence of a radical initiator at a temperature of 150.degree. C.-200.degree. C. a mixture of 1 mole of: (1) a nitrogen-containing compound as a telogen which is a heterocyclic amine of formula: ##STR14## in which R.sub.14, R.sub.15, R.sub.16 and R.sub.17 independently are a hydrogen atom or alkyl having from 1 to 6 carbon atoms, R.sub.18 is a hydrogen atom, an alkyl having from 1 to 6 carbon atoms, an aminoalkyl group having from 1 to 2 amino groups and from 1 to 6 carbon atoms or a hydroxyalkyl having from 1 to 2 hydroxyl groups and from 1 to 6 carbon atoms, and A is an oxygen atom or a group of the general formula ##STR15## in which R.sub.20 is (a) H, (b) alkyl of 1-6 carbon atoms, (c) aminoalkyl of 1-2 amino groups and 1-6 carbon atoms, or (d) hydroxyalkyl of 1-2 hydroxyl group and 1-6 carbon atoms and (2) 0.1 to 20 moles of an alpha-olefin as a taxogen of the general formula, R.sub.5 --CH.dbd.CH.sub.2, in which R.sub.5 represents a hydrogen atom or an alkyl group having from 1 to 28 carbon atoms whereby said taxogen becomes attached to the carbon atom in the .alpha.-position to the nitrogen atom of said telogen.
- 3. A process of preparing a nitrogen-containing telomer containing a high molecular weight hydrocarbon group, of average molecular weight between 400 and 3,000, nitrogen content of from 0.1 to 10 wt %, soluble in fuel oils and lubricating oils, which consists of subjecting to a radical telomerization reaction in the presence of a radical initiator at a temperature of 150.degree. C.-200.degree. C. a mixture of 1 mole of: (1) a nitrogen-containing compound as a telogen which is a diamine of formula ##STR16## in which R.sub.21 represents a divalent hydrocarbon group having from 1 to 45 carbon atoms, R.sub.22, R.sub.23 and R.sub.24 independently represent a hydrogen atom or alkyl having from 1 to 45 carbon atoms or R.sub.21 and R.sub.22 join to form a five- to seven-membered saturated aliphatic ring which is unsubstituted or substituted by 1 to 3 alkyl substituents each having from 1 to 6 carbon atoms and (2) 0.1 to 20 moles of an alpha-olefin as a taxogen of the general formula R.sub.5 --CH.dbd.CH.sub.2, in which R.sub.5 is alkyl having from 1 to 28 carbon atoms whereby said taxogen becomes attached to the carbon atom in the .alpha.-position to the nitrogen atom of said telogen.
- 4. A process of preparing a nitrogen-containing telomer containing a high molecular weight hydrocarbon group, of average molecular weight between 400 and 3,000, nitrogen content of from 0.1 to 10 wt %, soluble in fuel oils and lubricating oils, which consists of subjecting to a radical telomerization reaction in the presence of a radical initiator at a temperature of 150.degree. C.-200.degree. C. a mixture of 1 mole of (1) a telogen which is a nitrogen-containing compound which is a polyamine of formula
- H.sub.2 --N(R.sub.29 --NH).sub.n --H
- in which R.sub.29 is an ethylene group, a propylene group, or a trimethylene group, and n is an integer of from 2 to 11, and (2) 0.1 to 20 moles of an alpha-olefin as a taxogen of the general formula R.sub.5 --CH.dbd.CH.sub.2, in which R.sub.5 is alkyl having from 1 to 28 carbon atoms whereby said taxogen becomes attached to the carbon atom in the .alpha.-position to the nitrogen atom of said telogen.
- 5. A process according to claims 1, 2, 3 or 4 wherein said radical initiator is a peroxide.
- 6. A process according to claims 1, 2, 3 or 4 wherein said peroxide is used in an amount of from 0.005 to 0.3 moles per mole of said taxogen.
- 7. A process according to claims 1, 2, 3 or 4 wherein said radical telomerization reaction is effected by application of actinic light having a wavelength not higher than 300 nm.
- 8. A process according to claims 1, 2, 3 or 4 wherein said radical telomerization is effected in the presence of a radical initiator while applying actinic light having a wavelength not higher than 300 nm.
- 9. The process according to claims 1, 2, 3 or 4, further comprising reacting said nitrogen-containing telomer with a boron compound which is at least one member selected from the group consisting of boron acids, boron oxides, boron halides, borates and low alkyl esters of boron acid at a temperature of from 50.degree. to 250.degree. C., thereby obtaining an oil-soluble nitrogen and boron-containing compound having an average molecular weight not less than 300, a nitrogen content of from 0.1 to 10 wt % and a boron content of from 0.05 to 7.0 wt %.
- 10. The process according to claims 1, 2, 3 or 4, further comprising reacting said nitrogen-containing telomer with a boron compound which is at least one member selected from the group consisting of boron acids, boron oxides, boron halides, borates and low alkyl esters of boron acid at a temperature of from 50.degree. to 250.degree. C., thereby obtaining an oil-soluble nitrogen and boron-containing compound having an average molecular weight not less than 300, a nitrogen content of from 0.1 to 10 wt % and a boron content of from 0.05 to 7.0 wt % wherein the ratio in number of the nitrogen atoms to the boron atoms in said nitrogen and boron-containing compound is in the range of 1:0.05 to 5.
- 11. The process according to claims 1, 2, 3 or 4, further comprising reacting said nitrogen-containing telomer with a boron compound which is at least one member selected from the group consisting of boron acids, boron oxides, boron halides, borates and low alkyl esters of boron acid at a temperature of from 50.degree. to 250.degree. C., thereby obtaining an oil-soluble nitrogen and boron-containing compound having an average molecular weight not less than 300, a nitrogen content of from 0.1 to 10 wt % and a boron content of from 0.05 to 7.0 wt % wherein the ratio in number of the nitrogen atoms to the boron atoms in said nitrogen and boron-containing compound is in the range of 1:0.05 to 5 and said boron atoms are coordinated at the nitrogen atom.
- 12. A process according to claim 1 wherein said telogen is an alkanolamine in which at least R.sub.11 and R.sub.12 independently represent a hydrogen atom.
- 13. A process according to claim 1 wherein said telogen is a cycloalkanolamine in which R.sub.10 and R.sub.11 join to form a five- to seven-membered saturated aliphatic ring and at least R.sub.12 is a hydrogen atom.
- 14. The process according to claim 5 wherein in said diamine at least R.sub.22 and R.sub.23 independently represent a hydrogen atom.
- 15. The process according to claim 3 wherein in said diamine R.sub.21 and R.sub.22 join to form a ring and at least R.sub.23 represents a hydrogen atom.
Priority Claims (2)
Number |
Date |
Country |
Kind |
60-223827 |
Oct 1985 |
JPX |
|
61-132789 |
Jun 1986 |
JPX |
|
Parent Case Info
This is a continuation of application Ser. No. 914,467, filed Oct. 2, 1986 now abandoned.
US Referenced Citations (5)
Continuations (1)
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Number |
Date |
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Parent |
914467 |
Oct 1986 |
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