The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C≡C(CH.sub.2).sub.aOCH.sub.2OCH.sub.2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C≡C(CH.sub.2).sub.aOH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH.sub.2OCH.sub.2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH.sub.3(CH.sub.2).sub.b][CH.sub.3(CH.sub.2).sub.c]NC.sub.6H.sub.5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.

The present application relates to branched acetal compounds. The branched acetal compounds have utility as additives in paint and coating compositions. The branched acetal compounds exhibit reduced Volatile Organic Content (VOC). When added to a paint or coating composition, the branched acetal compositions of the present application provide satisfactory coating coalescing activity and reduced VOC content.

The present application relates to branched acetal compounds. The branched acetal compounds have utility as additives in paint and coating compositions. The branched acetal compounds exhibit reduced Volatile Organic Content (VOC). When added to a paint or coating composition, the branched acetal compositions of the present application provide satisfactory coating coalescing activity and reduced VOC content.

A process for preparing 4-penten-2-ynal of the following formula (2):

CH.sub.2CHCCCHO(2)

the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1):

CH.sub.2CHCCCH(OR.sup.1)(OR.sup.2)(1)

wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms,
to obtain 4-penten-2-ynal (2).

##STR00001##

A process for preparing 4-penten-2-ynal of the following formula (2):

CH.sub.2CHCCCHO(2)

the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1):

CH.sub.2CHCCCH(OR.sup.1)(OR.sup.2)(1)

wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms,
to obtain 4-penten-2-ynal (2).

##STR00001##

A process for preparing a dienynal compound of the following general formula (2): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCHO (2), wherein n represents an integer of 0 to 11, the process comprising a step of hydrolyzing a dialkoxyalkadienyne compound of the following general formula (1): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCH(OR.sup.1)(OR.sup.2) (1) wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, mere preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

##STR00001##

A process for preparing a dienynal compound of the following general formula (2): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCHO (2), wherein n represents an integer of 0 to 11, the process comprising a step of hydrolyzing a dialkoxyalkadienyne compound of the following general formula (1): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCH(OR.sup.1)(OR.sup.2) (1) wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, mere preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

##STR00001##

A composition containing a polyphenol compound (B), wherein the polyphenol compound (B) is one or more selected from the group consisting of a compound represented by the following formula (1) and a resin having a structure represented by the following formula (2):

##STR00001##

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).

##STR00001##

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which X.sup.1 represents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which M.sup.2 represents Li or MgZ.sup.2, wherein Z.sup.2 represents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which X.sup.3 and X.sup.4 may be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which M.sup.1 represents Li or MgZ.sup.1, wherein Z.sup.1 represents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).

##STR00001##